14 Ways To Be A Great Startup CEO

//This post originally was published at Onstartups, where you can check out more of my writingEveryone thinks that being a startup CEO is a glamorous job or one that has to be a ton of fun. That’s what I now refer to as the “glamour brain” speaking aka the startup life you hear about from the press. You know the press articles I’m talking about… the ones that talk about how easy it is to raise money, how many users the company is getting, and how great it is to be CEO. Very rarely do you hear about what a bitch it is to be CEO and how it’s not for every founder that wants to be an entrepreneur. I’ve spent a lot of time recently thinking about what it takes to be a great Startup CEO that is also a founder. Here are some of the traits I’ve found.

Be A Keeper Of The Company Vision

The CEO is the keeper of the company’s overall vision. I’m not talking about the vision for the next few months, but the larger road ahead. The CEO needs to be able to keep things on course for the current quarter to make sure that the large overarching vision of the company can be achieved. The takeover the world vision of a startup usually can’t be achieved in one year or even in some cases, like Google, in a decade. It takes a great startup CEO to keep the company on track to achieve that vision. A great startup CEO will often judge upcoming initiatives to see if they fit in as a piece of the large puzzle for the bigger vision.

Absorb The Pain For The Team

A startup CEO needs to be the personal voodoo doll for a startup. They need to be able to take on a strong burden of stress, pain, and torture all while making level headed decisions. You can’t have the troops stressing and worrying about the difficult challenges at hand. A good startup CEO will absorb the stress, so the rest of the team can carry on. He also needs to be able to mask this pain and stress. Not that he should hide or lie to the team- I’m not encouraging that. Most of the day to day nuances+stresses of a startup aren’t worth having the entire team worry about and the CEO needs to bear that pain.

Find The Smartest People And Defer On Domain Expertise

A startup CEO has a great knack for finding talent. The key is finding people that are smarter than you on specific topics. It might be technical team members/leaders or it might be a new VP of Biz Dev. A startup CEO has to have the ability to find these people and make relatively fast decisions to hire them. They also have to be able to show the fire and passion to convince them to leave what is most likely a better paying and more secure job to join the company. The real key to hiring as a startup CEO comes after the hire. A great startup CEO will be able to trust the hires that they make and defer to them on areas of domain expertise. It’s hard to let go, but you have to learn to, especially when the company grows.

Be A Good Link Between The Company + Investors

Whether you want to believe it or not, you are not an investor’s only portfolio company. Even if you are a superstar, they have a handful of other companies to help and a ton of incoming potential portfolio companies. A good investor will pick 2-3 new companies per year to work with. A good startup CEO will be a good link between progress, issues, and areas where they need help with investors. A good portion of early stage startups that raise money will have a board comprised of 3 people: the CEO founder, the investor, and an independent board member. You are the lone representative for your cofounder and other employees.

Be A Good Link Between The Company + Product

I have this unwavering belief that the best companies are those that keep a founder as CEO for the long haul. Not because the founders have the right to be CEO, but because the CEO needs to be close to the product vision of the company. Founding CEOs understand this the best and can carry out that same unified vision over time. To fill in the management gaps a great COO, other board members, and heads of divisions will come along. It’s a strategy that Facebook has employed and why Apple has had a great resurgence with Steve Jobs at the helm. It’s all about keeping the CEO as close as possibly linked to the product.

Be Able To Learn On The Job

Most startup CEOs didn’t start out with an MBA or some background in growing a company from nothing to something. The best have an ability to learn along the way and embrace their failures to become a better leader. Zuck started when he was 19 and now 7 years later, runs the most powerful internet company. Don’t worry about whether “you’re qualified” as it’s hard to put typical qualifications on the job. You’ll learn the really core stuff along the way. The best startup CEOs will surround themselves with smart mentors to be a sounding board along the way.

No Experience Almost Preferred

It’s almost better to have a blank slate of zero experience as a startup CEO. If you come in with preconceived notions and block out the scrappy methods of a startup founder, it actually hurts you. Traditional education often trains you to be CEO or manager for a much larger company, not for a startup of under 50 people. It’s a different kind of leadership and company.

Have An Uncanny Ability To Say No

You will be inundated with a list of requests from potential partners, investors, employees, and more. They will all sound absolutely wonderful. As you grow, you will also have the resources to execute more of them. Don’t. It’s easy to say yes, but so very hard to say no. By having an uncanny ability to say no, you can keep your company on track with the large vision you maintain. It will also keep your team members (notice I don’t like to use the word “employees”) laser focused and feel more rewarded as they are able to focus on one thing for a good chunk of time. I’ve seen too many startups sink because the CEO keeps changing what the head of product and engineering should be doing.

Have Some Technical Knowledge And Skillset

A good startup CEO shouldn’t be afraid of a little bit of code and a text editor. They don’t need to be diving into the source code on a daily basis, but they need to understand the technical requirements. It’s easy to say “go build this”, but it’s a whole other ball game to understand how to build it. What seems simple may be a huge mountain of a technical feat that just isn’t feasible with the given resources and deadlines. It can also help lend some street cred with hiring early technical team members too.

Be Able To Break Things Down Into Sizable Chunks + Milestones

Remember that huge unwavering vision that you are the keeper of? Odds are it only makes sense to you and your cofounder. You will need to break it up into sizable chunks and milestones for the rest of the team to understand it. You also need to be able to pick when and where to conquer things strategically. What is the past of least resistance so you can gain traction? What can you do first with your given resources?

Have The Ability To Call An Audible

Nothing goes according to plan. Things fall through, people quit, shit happens, servers crash, and other random things go bump in the night. You’re going to have to deal with it and fast. This is a football term:

"Seen when the quarterback goes up to the line of scrimmage, sees a defensive alignment he wasn’t expecting, and adjusts by yelling out a new play."

You’re going to come up against things that you didn’t expect and just be able to call an audible. Launch faster, spend more money here, or even abandon a project.

Can Motivate The Team Through Despair

People love to talk in this business. People love to talk even more when you’re company isn’t fairing well. A great CEO will be able to take those moments of public despair and keep the company focused. They will be able to debunk the rumors or even approach them head on by keeping the members of the company focused on the bigger mission at hand. It can come in simple 5 minute talks or motivational emails. The worst thing you can do is avoid the situation and be passive aggressive. I repeat: DO NOT WUSS OUT.

Be A Great Communicator

You need to be able to portray the energy and passion that you feel into others…over and over and over and over and over and over again on a daily basis. As a startup founder you need to communicate the vision and hope for the future of your startup to the rest of the world. You need to be able to break down the overall vision of the company into something that mere mortals can understand. You can’t speak in crazy technical jargon or industry terms. It needs to be simple, clear, and compelling. You also need to be able to argue your point. Many will pick “fights” with you just to see how strong willed you are. Be respectful, but be very confident in your answer. Often wrong, but never in doubt my friend.

Don’t Be A “Fake CEO”

Mark Pincus, CEO of Zynga, makes a strong case for not being a fake ceo. In short, worry about things that produce results, not fame. If it’s between going to a conference/doing an interview or completing a deal, get the deal done. Don’t “leave it to someone else”. You need to get your hands dirty every single day.

By no means is this an exhaustive or definitive list. In some cases, the traits listed above might be counter-intuitive. What are some traits you’ve seen in great founding startup CEOs? Not the glamorous job you thought it was, eh?


March 14, 2012 VIEW POST

NYC Students: Want a Fast Track Into The Book Publishing Industry? Intern To Help Launch My Book With A Major Publisher.

You’re a junior or senior either majoring in english or PR and want to get a fast track into the publishing industry. My book, The Ultralight Startup , launches this spring. It’s published by Penguin Publishing, an imprint of Pearson, one of the world’s largest publishers in the world. This is a once in a lifetime opportunity to get fast tracked into the world of book publishing whether you are an aspiring editor, author, or publicist. More about the role and how to apply are below!

More About Myself And The Book…

Book Description From The Jacket

The Ultralight Startup is the book I wish I had when I was starting out five years ago. The Ultralight Startup offers a surefire plan for building an astoundingly successful tech startup for anyone with nothing more than a good idea and a lot of passion. It’s easier than ever before to launch a startup, but in a world where barriers to entry virtually nonexistent and everyone wants to be the next Facebook, competition is fierce. To win, you have to outsmart, outdo, and outshine everyone else. But if you’re just starting out and lack the money and clout to make an automatic splash, how do you differentiate yourself from all the rest?

My Bio

My Twitter


Time commitment: 1-2 days a week working out of the Onswipe NYC offices. We’re one of the fastest growing startups in NYC, so you will learn a lot about business as well.
  • Helping work with the media to promote the book.
  • Helping liaison with Penguin on book promotion.
  • Helping liaison with Penguin on any logistics of the book launch.
  • Helping coordinate an east coast college tour.
  • Helping schedule a launch event in New York City.
  • Helping work with influential authors, entrepreneurs, and VCs.
  • Managing social media and blog accounts for the book.
  • Helping run contests and promotion such as “meeting the VCs”.

What I’m Looking For

  • NYC Based.
  • An English or PR major that is outgoing and well spoken.
  • Very familiar with Twitter, Tumblr, and Facebook.
  • You are a blogger and writer yourself.
  • You are plugged into the NYC startup community in some fashion.
  • More of a hustler than anything else.

[wufoo username=”onswipe” formhash=”z7x0k1” autoresize=”true” height=”1089” header=”show” ssl=”true”]

December 26, 2011 VIEW POST

Why Onswipe Just Raised A $5,000,000 Series Awesome

We just announced that we raised a Series Awesome. Yes, the documents actually say that :). Most people are probably wondering what prompted us to do this such a short while after we closed our seed round literally 5 months ago from today. Here’s why:

Bigger Opportunity Than We Thought

Andy at Betaworks put it the best: “Onswipe is a lot like Aol in 1995 in terms of opportunity.” The Internet was just a year old and if someone was able to own the space, they could build a massive company. We feel the same holds true with the tablet market. It’s growing faster than we ever thought and we realize that there’s a unique once in a generation opportunity to define the way the world interacts with the web. What you’re seeing and what’s talked about today is a small small part of our overall vision. The sky is the limit. We get a chance to rewrite all the rules and change everything.

Going for the big win

We’re not doing something small and we’re not interested in selling the company. We’re lucky and realize the opportunity ahead and found people to back us that believe in the same. We have money from investors behind companies like Twitter, Tumblr, Groupon, Facebook, Foursquare, Google, and more. We love what we do and we know that a monstrous opportunity is ahead, so we’re going to need a lot of capital to take advantage of it.

Secret Sauce

It seems we’ve found a secret sauce about how to develop relationships with publishers and brands. There’s still a lot of work to be done, but we believe we can own the market by elveraging this. We have a distinct philosophy of partnering with publishers instead of becoming YAV “Yet Another Vendor”. Part of it is tech and part of it is good ole’ relationship building.

Ability to recruit top engineers

We’ve been really lucky that we have been able to build a killer engineering team. Talent is hard to come by and we have a specific skillset we need. With $5 million in cash, we can really scale up our engineering team to build what is the best Front-end HTML5 team in the world.

More demand than we ever imagined

Apps are bullshit and publishers don’t want to be beholden to them. Advertisers want something more like print and less like bottom of the barrel CPM or Google Adwords. Our landing page has been and still really is pretty vague. People sort of know what we do, but the notions behind it have gotten a lot of people excited.

All in the family

We’re lucky, we have a great group of investors. Alex at Spark has been like a cofounder+board member to the team and there with us along the way. The best companies are built upon relationships and we’re happy to continue our relationship for the long haul with Spark. Everyone else involved is a close knit group of individuals that have been there for us along the way. We’re proud to say that 100% of investors with pro-rata rights took their pro-rata. We’re also welcoming new investors in the round. Paul from Lightbank tweeted out a ballsy quote at demo day and we quickly connected as Paul and the team at lightbank know how to build monstrous companies. Lerer Ventures, Yuri Milner, and Thrive Capital are also participating as new investors that we’re thrilled to have on board.

The time is now and the time is ours. A lot of people may tell us congratulations, which is nice, but in reality we have a lot of work ahead. No retreat, no surrender. Thank you everyone for believing in us.

Jason L. BaptisteJune, 2011 

June 3, 2011 VIEW POST

13 Ways To Pull Off A Killer Demo Day Presentation

// This post originally appeared at Onstartups where I write about startup awesomeness with Dharmesh Shah.

There are over a hundred seed accelerators in the world and many more are popping up every year. In New York City, there are going to be 6 more this summer on top of TechStars NYC. The common thread amongst all of these programs is what is now known as “Demo Day”, which is a single day (sometimes days) where a number of investors are put in to a room to watch all of the participating companies present for 6-8 minutes. Recently, my company OnSwipe was a part of the inaugural Demo Day in NYC for TechStars. Everyone has been asking me how we prepared and put together our demo day presentation. Without further adieu, here’s how. You may want to watch the recording of my presentation below first: Actual Presentation

Put together slides with very few words

You should not have the audience focused on your slides, but your words during the presentation. Bullets are an absolute no-no throughout the presentation. My presentation had one sentence at most per slide with an accent color highlighting what was a really important word for the audience to understand. The slides should set the tone for what you are currently talking about to keep everyone on track. Stay away from transitions or overly flashy slides. They were cool when you were in junior high, but don’t add a lot when talking to a large crowd. Slide Deck (some things might be out of place due to 2 animations)

Make Sure There Is A Screen In Front Of You On Stage

The worst thing you will ever do is look back at the screen. This makes you seem unprepared, especially during demos. It also makes everyone think you didn’t prepare with the person, usually your cofounder, that is controlling the slides. You don’t want to look down at it too much, but it’s there in case shit happens. In a split second you could be on the wrong slide or miss a beat. Instead of turning around to look back confused at the screen, you can properly pause and guide the presentation back to order while looking ahead. It’s a small subtle, yet useful prop. Make sure it’s there.

Practice, Practice, Practice

I practiced religiously before going on stage. Dave Tisch and Dave Cohen probably wanted to murder me when I skipped the public pitch practices with all the teams, but I was secretly practicing at home or late at night. I look at a presentation a lot like product. It just needs to be broken and tweaked a lot. It isnt’ ready for public consumption or scrutiny until you’ve fine tuned it enough. Make sure you practice until no end. It’s what makes you comfortable and confident.

Be bold

This might just be my style, but you need to be bold…very bold. You are going to be presenting with 10+ other companies or even more that day. Investors and press get antsy very fast. When was the last time you could sit through 5 hours of pitches easily? By being bold, you can give a great refreshing jolt to the crowd and pique their interest. It’s also great to stand out with a ton of press in the crowd as they will want to do an interview with you afterwards. “Be so good they cannot ignore you.”

Speak in tweetable soundbites

People love to tweet live events and demo days are no different. Inside of the room, you will have a great group of influential people that can send your message out to the right people. The thing is, they can’t send out the entire presentation, they can only send out 140 characters at a time. In our case, we had 3 tweetable soundbites that became well known afterwards. These weren’t by happenstance, but planned well in advance:

Love it. @onswipe not raising a Series A, but raising a Series Awesome #techstarsless than a minute ago via TweetChat Favorite Retweet Reply

The “Three Acts”

The best way to do a demo day type presentation is to put the entire delivery into three different acts. Entrepreneurship and delivering a presentation is absolutely no different than theater. You should look at your delivery as a spectacle that enlightens those in the audience, not a typical slide deck pitch.

Act I - The Setup Setup the enemy for the entire presentation, the elevator pitch, and the big vision business. It should be under 90 seconds and even that is something I found difficulty with. The goal here is to give context, hook the audience in, and get to a killer demo.

Act II- The Demo This is what really matters. Too many companies approach demo day as investor day, instead of showing what they’ve built off in-depth. Screenshots are a no-no and sadly, pre-recorded videos seem to be the way to go due to Wifi. Show off a logical progression of what your product does. Nothing gets someone ready to write a check like a great demo.

Act III- The Execution This is where you talk about what you have accomplished and where you are going. I usually like to talk about a few things: Press, current investors, business development deals, and the team you have been able to attract. This shows where you have been and how you are able to execute as a team. You should also make sure that you talk about what’s next. When are you launching? are you raising money? what is the big credo and philosophy behind the company? Tell the world why you exist and why you are going to take over the world.

Get to the demo as fast as possible

This was the biggest lesson we learned through practice. The first version of the presentation took 2:30 to get to the demo. That was an absolute eternity. Even now, I could have shortened things by a good 30 seconds or so. Make sure you get to the demo as fast as you can. The other side of it is, making sure that you give enough context to the audience.

Have an “enemy”

We set out to say app store apps for content publications like the Wall Street Journal and Wired were just complete bullshit. We were very bold in this statement, but we backed it up with undeniable fact. If you are going to make an enemy, make sure you have the weapons to combat them. You have to seem sure when declaring ane enemy and have a logical argument.

Make sure the big long term vision is known

Too many investors and potential partners will think about the present since that is mostly what you are showing. Spend time talking about the big vision in terms of product and in terms of business model. Your product is often different than your business model. ie-  Google’s product is search, but it really makes money through advertising. Sometimes you may not know what this big vision is, but if you do, make sure that is known. Most people thought our big vision was: be a WordPress plugin that makes things pretty. We made it clear that our goal is to power the advertising in a world where content is consumed with tablets, not point+click devices.

Be fashionable

I’m an outlier here, but the pink shirt went over well. It made me hard to ignore and ended up color coordinating the presentation. Trivia: The onswipe pink colors come from that shirt, not the other way around. Make yourself memorable with appearance. People will remember your ability to command an audience and that can often be done through how you dress. Once again, demos and presentations are not pitches, but theater.

Have an “ask”

Most companies go into a demo day with an intention of raising money. It might be something direct with an exact dollar amount or it might just be an announcement that you’re playing around in the waters. Either way, make sure you have an ask that lets the world know your fundraising plans. The biggest problem in entrepreneurship is the fact, that most entrepreneurs just don’t ask. If you have existing fundraising commits, let the world know who is in and for how much if possible. My buddies at thinknear did this by letting the world know IA Ventures was in for 400k of a 1.2 million round.

Show Off Social Proof

Social proof is one of the best things that you can portray during a presentation. Do not be arrogant or cocky, but certainly be confident. Show the world who is behind you and what you have accomplished. Nothing gets an investor more excited than tangible traction, social proof from their peers, and the ability to execute.

Things that didn’t work along the way

  • We spent a lot of time getting to the demo. We originally had a lot of social proof and big vision talk before the demo. That got people antsy. Let the demo be your proving ground and then
  • Don’t try to practice in full run throughs at first. Go act by act, screwing up along the way.
  • Do not use anything from your investor slide deck. Even though we have never used a slide deck to raise money, we still sort of have one. I dusted it off from the Series Seed and tried to insert some slides. It just doesn’t work for demo day. Demo day pitches should be looked at a lot differently than your traditional investor pitch at the end of the day. Demo day pitches really appeal to three broad crowds, with some companies focusing in on one more than the other: press, investors, and potential partners.
In short, this was the most important day of my life and a huge success. The only downside, is that it meant TechStars is officially over. You should apply to the program , and if you get in, hopefully this post will be of use.

Have you presented at a “Demo Day” before?  Any tips of your own that you’d like to share?

May 24, 2011 VIEW POST

9 Reasons Why The Killer Tablet App Is The Browser

//This post originally appeared on Boston Innovation as a guest post.

The tablet market is exploding and exceeding everyone’s wildest dreams. Apple is in the lead, but the Android tablets along with many others are on their way. In an interview back in January, I stated that “apps are bullshit for content”. I thought it would be good to clarify that statement and explain my reasoning why the future of content on tablet devices is not going to be delivered through apps, but through one killer app: the browser.

Referral Traffic Is Lost With Apps

The majority of a content owner’s traffic comes from referral traffic such as search, share, and email. That traffic has and always will go back to the website itself. Even if a link is opened in the twitter app, it is still showing that content in a UI web view. It’s close to impossible to have that traffic open up in a native app, which would require a user has it installed already. Sure, it could prompt the reader to download the app, but that is a painful experience. A reader wants instant gratification, not a friction filled process with a long download.

If publishers create apps instead of focusing on the web they throw out half of their traffic .

Readers Are Already Going To The Site

Readers are already trained to go to a publication’s website. Why should they be funneled through a website, told to download an app, and then navigate to an article. Larger publications may have readers search within an app store, but that only applies to larger media brands, not the type of influencers that are dominating the web now. This very article you are reading now is appearing on the web and not an app.

HTML5 Is Capable To Deliver App Like Experiences

Problem: Publishers want to deliver a great experience that can take advantage of what’s possible on tablet devices.Solution (for the first 9 months): Create apps that are essentially glorified PDFs and cost a ton of moneySolution (now): Use HTML5 to provide the same type of experience and on the web.

HTML5 can’t do the crazy game enabled capabilities…yet (WebGL please?), but it certainly can do many of the fast + speedy content effects seen in native content apps. Transforms, fonts, and more make it possible that the web can be indistinguishable from native apps. It’s hard, don’t get me wrong, but it’s now possible.

Fixing The “Stuff To Do” Problem

When you buy a tablet, you’re given a new device and need “Stuff to do”. Apps clearly fill that void by allowing you to play games, consume content, and more. Sure you already browse the web, but you download apps because you know they are made for that device. Sadly, most of the web is not made for tablets…yet. By making the web tablet and touch friendly, it increases the value of tablets tremendously regardless whether it is iOs or Android based.

Scoble explains this well here . It’s simple, the iPad has a ton of stuff to do by having a lot of tablet apps. If Google and others focused on making the web a better place out the gate for tablet users, then they can strongly counter that argument.

Homescreen Fatigue

Readers will only keep so many apps on their homescreen at one given time. You’re also competing against apps that will never go away such as safari, youtube, mail, and more on a reader’s homescreen along with apps like angry birds+instagram, that aren’t even content apps. On the other hand, readers are used to navigating to your site or bookmark specific content within the browser.

Consistent Cross Device Experience

By focusing on the web, you can create a consistent cross device experience. It’s hard to create apps that will work across all touch devices, if not nearly impossible. By focusing on the web, you can know that a reader will have the same consistent experience whether they are on iPad, the Xoom, or a the PalmPad. The web is also a write once, deploy everywhere environment, where apps are not. Sure there are quirks for each browser+device, but they pale in comparison to developing native apps across all platforms.

The Web Was Meant For URLs

The web was meant to have each individual piece of content have a permanent place in history. With apps there is no foot in the ground for a piece of content. If you want to directly link to a piece of content inside of an app, how do you do that? You can’t. The web was built upon urls and people sharing+linking to them. If apps were to dominate the world, we’d lose that structure.

App Stores Don’t Provide Real Distribution

Publishers think that app stores are the holy grail for traffic and distribution, when they are in reality driving very little “new distribution”. App stores have horrible discovery. The best way to discover new content apps is through a pure search query. Odds are though, that if you love a media property enough to search for it in an app store, you already visit the site. You are not a new reader.

Exercise: if you and two friends started a publication tomorrow, put it in the app store, and could not use any existing brand leverage, how many downloads would you get? Very very few, if any. There is no magical customer acquisition bullet here.

Apps like the New York Times also receive so many downloads since they are a centuries old brand that can drive downloads. The number of users of the app are still some # < their overall web usage.

What does provide real distribution? Social sharing and distribution. If sites take advantage of intelligent recommendations and build in sharing not as a bolt on to their application, they can

Follow The Money

Apps and the keepers of the platform ultimately decide what a publisher can or cannot do. How much can they take for subscriptions? What data can they collect? When can they push an update? Going through intermediary app stores puts the decisions they can make from a business perspective in the hands of others. Those decisions, especially around monetization are the lifeblood of any publisher. Putting that control in the hands of a select few is scary and literally gives away the power they have. The most alarming is Apple’s decision to take a 30% cut of all subscriptions and making that a mandatory option. On the web, publishers can choose the ads they want, display the content they want, and give up a much smaller peice of the pie.

So where do apps make sense in the tablet world? With applications that exist PRIMARILY as an app, not as a supplemental app to a website. Examples:

Flipboard and Angry Birds make total sense as apps. They take advantage of what can be done natively and don’t have web counterparts.

All content apps such as CNN, Huffington Post, and more are just extensions of a website, where there real traffic exists. They should not be apps. The same can be seen with SaaS apps such as basecamp and their recent HTML5 version of the site for touch devices.

It’s not a question of if after talking to publishers of all sizes, but a question of when.

March 22, 2011 VIEW POST

How To Become Legendary- 23 Things Michael Jordan Taught Me About Entrepreneurship

//This article originally appeared at OnStartups, where all my writing appears exclusively.

If you know me personally, or even digitally , then you know that I am a physical fitness and athletic enthusiast. I find that there is a certain level of determination that is built up by being physically fit and sticking to a regimen. Athletics and exercise are the purest physical expression of true mental discipline that one can find. As an entrepreneur, I don’t think I would be able to do what I do without the mental preparedness a daily workout routine brings. With so many parallels between athletics and entrepreneurship, I asked myself “Who is the Steve Jobs of athletics?” This question can certainly be debated, but at the end of the day I arrived with an answer of Michael Jordan. A recent ad campaign by Nike with Michael Jordan is focused on the phrase “Be Legendary.” and the quotes that come from them are absolutely golden. In truth, some of the best entrepreneurial advice I have ever received has come from Michael Jordan and this campaign. Here are 23 insights that I’ve learned from Michael Jordan:

It’s About Knowing Where You’re Going

You have to have a clear path as to where you want to go. As a startup, things change along the way. Your execution might make you pivot or implement a different solution. At the end of the day, you need to stick to a clear vision and problem that you’re trying to solve. If you’re lucky enough to succeed, the road to where you’re going may look a lot different than it did when you first started. Take a look at Google- make the world’s information freely available. That has been the goal from day one, and despite solutions consisting of email, maps, video, operating systems, and more, that is still their goal at the end of the day. Never forget where you are going as an entrepreneur with your company.

Don’t Forget Where You Started/Came From

This holds true for you as a person as much as it holds true for the company itself. Though we do it for more than the money, money can often change people to forget their humble beginnings. Many great entrepreneurs came from absolutely nothing - just an idea that might change the world one day. Don’t ever forget that child like desire you had the first day you started. If you harness that essence, no money or fame can ever change you. Never forget your family and your close friends that were there before you started upon this journey. The best thing a company can do is keep a list/wiki of company lore that will remind them of their adventures. The long flights, the growth in employees, the launches, the failures, and more from the early days. Andres and I have been traveling the country with PadPressed. We’ve encountered some victories and many failures along the way, but we’re keeping a record of it through writing, tweets, and pictures.

Have the courage to fail

Failure is a part of anything in life, but having the courage to face it head on is what makes you stronger. We hear so much talk about “it’s okay to fail”, but I don’t think there’s enough clarification. You shouldn’t let your startup as a whole fail, that’s not something you should easily let happen. Startups are really a compilation of many small instances of victories and failures. It’s embracing those small instances of failures that will let you learn and adapt better. Think of embracing failure as the entrepreneurial equivalent of an immune system. By embracing failure, you learn what went wrong, what’s bad, and how to prevent it from happening again. You build up a resistance to that specific instance of failure.

Don’t break when broken

What goes up, must come down. Starting a company is a roller-coaster ride like none other. YCombinator actually has a graph here about this exact subject . You will feel broken inside and figure it’s time to give it all up. That might be quitting yourself, selling the company, taking a weak deal, or even calling it quits on a smaller scale. DON’T. Emotions are fleeting and cloud your judgment. For the most part, something that makes you feel broken, should not break you. The true also holds same for the opposite.

Take everything given to you and make something better

Society is all about evolution, especially in technology and software. The greatest technologies take the fundamentals of what already exists in some form, but improves them with the new pieces that have evolved. I wrote about this earlier in a piece called “Build What Was Previously Not Possible." As an entrepreneur you will continually find new tools and innovations brought forth by other entrepreneurs. Take every single relevant thing you can find and bake it in to your product to make something better. For some that might be mobile, social, local,etc. Always ask yourself: "Am I using all the resources that are available and making something better?" We literally get nowhere with complacency, but get everywhere with advancement. Don’t change the game, evolve the game.

Work Before Glory

The best entrepreneurs are humble and don’t really care about the glory. One of the things that Dharmesh has taught me over the past few months is to keep a level head and be humble. Don’t worry about the next press article that comes out about your company. Eventually there will be too many of them that it won’t matter. It should be about the work you produce instead of the side benefit of glory. Your work will live on forever, but the glory will fade away when the next acquisition or rumor pops up. Legends are products of their work, NOT their glory.

Do what they say you can’t

The competitive nature of entrepreneurship is a fun one. Many people will tell you that it can’t be done or that it is too crazy. They will tell you that a better X can’t be built or you won’t be able to accomplish a small goal like fundraising or hiring. The people telling you this might not even be strangers, but close friends and family members. The only way to prove them wrong is to do it.

It’s not about the tech, it’s about what you do with it.

The tools and technology that is available to entrepeneurs just keeps on growing. Whether it’s social, HTML5, geolocation, node.js, cloud services, or whatever else, that’s not what this is about. Those tools by themselves are cool, but not that useful. The technology tools are like an artist’s paint brush or a baseball players bat. It’s about what you decide to create with those tools.

Be Scared Of What you won’t become.

As an entrepreneur, you probably have a very big long term vision that you want to accomplish. It can’t happen right now, but over time it eventually will. I always point out that Facebook started at one college, with one photo, no wall, and a mediocre design. Look at decisions as if they might compromise what you could become. If you take the easy route and make the wrong decision, you will not become what you should be. That should absolutely scare you. What if Zuck sold to Yahoo! many years ago? That has to be a scary thought as Facebook would not have become what it is today.

Make Others Scared Of What You Could Become

Entrepreneurs are often asked “So what if Google enters your market?” That’s a worthy question, but at the end of the day, your vision should be so mind numbingly amitious and huge, that it scares Google or someone else. Today you might be something small, but if you play your cards right, what you end up becoming is scary. The really smart entrepreneurs aren’t scared of the bigger guys as much as they are of the smaller, more nimble startups that COULD BECOME who they are now. At some point, everyone was no one.

Don’t finish where you began

Startups are all about momentum and forward moving progress. Every task, project, or new feature should be able to take you forward. It might even be okay if it took you backwards, as the journey backwards is still a journey. Spending a ton of time on something and just ending up where you began is something you should avoid as an entrepreneur.

Know what is within you, even if others can’t see it

Sadly, too many people in our industry disregard others that aren’t in the in crowd or very visible. They look at who an entrepreneur is now, but not at the true future potential of who that person will become. The same way a smart person knew that Facebook would be something big in 2004, is the same way a smart person knew that a 19 year old unknown kid from Harvard would change the world. Some people ask me why I put my phone number and other contact information out there publicly (fyi- it’s 201-305-0552). It’s simple- You never know who you might meet. They might not be somebody now, but over time they might become somebody legendary. If you can help them get there, it benefits everyone involved. By helping others, you eventually start to develop pattern recognition for finding great talent, which is a key component of being a leader.

Patience is more important than courage

We always want success now or even yesterday. It’s hard for us to realize that things won’t happen as fast as we want them to. Courage is certainly a very important trait, but more important is having the patience to see things through. When we look at the success of others, we only see the end result. Even if we see the journey along the way, it is still a small snapshot. Take in the whole picture and realize that there are no overnight successes.

Fulfill your destiny.

It takes a while to get to this point, but you eventually realize what your destiny is in life. You clearly know what you were meant to do with your life and what the end result will be. It takes a lot of trial by fire to get there, but once you do, you will become unstoppable. The real key to fulfilling your destiny is figuring out exactly what it is. Once you figure out what that specific destiny is, it’s a long journey, but the fire it generates inside, will put you on auto-pilot.

The press leads us to believe it is easier than it is

The press’ job is to write about stories that generate pageviews, since pageviews generate more advertising dollars. Failure and the grueling times don’t really get too many pageviews. Success, money, glory, and the end result of hard work certainly does get pageviews. This skews us to think that raising money, selling your company, or launching is just so easy. I’d wager a fair amount of money that you will almost never hear a story titled:”Startup X Fails To Raise $2,500,000 Dollars” unless there is some juicy gossip backstory attached to it. Get back to work and close the RSS reader.

The real work starts at the keyboard and with customers.

If you’re in a startup you’re either making something or selling something. If you haven’t made anything or sold anything, then I sincerely have no clue what you’re doing at a startup. Sure there are operational tasks that need to be handled, but all founders can bear that burden. As a whole, founders + early employees need to make sure their actions have a direct impact on something be made and/or something be sold.

Not every product or feature launch is a winner

Remember Beacon? Remember Google Buzz? Remember Yahoo! Live? Remember AppleTV V1? Well, you might, but not for good reasons. Not every feature or product launch is going to be a slam dunk. Even the giants in our industry like Apple can have products launch that don’t perform well. It’s impossible to shoot 100%, but what matters is that you take 100% of the shots that you should be taking.

Fire over flash

Pretty interface and nifty features are not the path to success. They are certainly a great advantage to have, but the product also has to have fire behind it. If you have a pretty application that provides no real “fire” aka utility to the user, then it won’t be used for long. Make sure you have fire before you have flash in your product.

Continue reading at OnStartups

February 28, 2011 VIEW POST

Thoughts On The @daily And My Challenge To Rupert Murdoch

//This originally appeared on the Onswipe company blog.I love the notions of the daily and what they are trying to achieve. I think at it’s core they truly want to do something risky, innovative, and something that was not possible before. There’s a lot to love, but there’s also a lot to dislike in the execution.

It’s against the real time nature of the web

Even delivering an “update” daily is just too slow for the way the web works. Setting any sort of defined delivery period is just silly. The web isn’t on a set time schedule, but an always-on network of flowing information. That’s the real special sauce of what’s happening in the media industry. The flow of information is no longer constrained by time, it is instantaneous and transcends time itself. By fighting against that, we’re taking a step backward.  Many people claim that the initial wait to download is too long and I agree, but the biggest problem is the day long wait for an update of any size.  It’s the time period, not just the size that is bothersome.

The Daily and apps in general are also against the real time nature of software. If the team at The Daily wants to update their software, it should be available instantly whenever anyone visits the site again. It should not go through the app model of sending an update to Apple and eventually all platforms, then requiring a delay and new download from the user.

Read The HIG

The human interface doesn’t feel like something meant for the iPad. It’s just awkward and uses button controls, especially on the bottom that are out of place. Each content app should be different, but it should feel like it’s within a consistent human interface. The fullscreen feel of The Daily is just weird too. I get the point, but it just feels out of place.  Flipboard did a good job of “effects”, but keeping things elegant.  The Daily should try to do the same.  Instead, things don’t feel readable, but more like an old school CD-Rom.

Subscriptions Are The Solution To a Problem That No Longer Needs Solving

Subscriptions and paying for content are a solution to the old economic model of newspapers/content. It cost a lot to print and deliver content via traditional media methods. Every night a newspaper had to be printed and then physically delivered. In order to do this, it just cost a lot of money. In the digital world, delivery costs are minimal, eliminating the need to have subscriptions costs cover them. In short, the problem of covering the cost of physical delivery no longer exists, therefore its solution, paid subscriptions, no longer needs to exist.

Not Optimized For The Social Nature Of The Web

The Daily just isn’t optimized for the new nature of the web which is now all about social. Social is not a bolt on aka adding share buttons. The commenting included inside of the Daily is interesting, but I would take it another level to show the entire conversation around a piece of content and also add geolocation to it. It’s time to reinvent media completely, not slightly add something new.  Gawker has the right idea by keeping relevant/highly shared content surfaced over a chronological order of articles.  Social and the presentation of the daily should be one in the same.

Too Susceptible To Churn

The Daily has one main point of access, which is through the user’s home screen. If the daily fails to deliver, the app will get deleted off the home screen, and will never return. On the other hand, if it were web based it would be easy to navigate to a site directly later on. Going to the app store and re-downloading it? Very very difficult. Being 100% reliant upon the app model makes content providers highly susceptible to churn.

Images Of Text

The articles are designed for print first and the web as an afterthought. Essentially, the articles are exported from InDesign or something like it as images and put into a simple app builder. I don’t want intense interaction, but I want to feel like I’m doing more than interacting with a glorified PDF reader. The iPad and the shift we’re seeing in media isn’t about making incremental improvements, but rethinking the entire solution as a whole.

The Ads Are Its Best Example

The ads in the daily are absolutely awesome. They aren’t interruptive, have taste, and not “too interactive”. iAds are the world’s best Flash ads… done in HTML5. The Daily decided to not use iAds, which was really smart. They took the essence of print, but brought it to the web with something new.

May A Million Dailies Bloom

The Daily right now seems ahead of its time, but it will eventually be something we look back on as common place. Slate started out being forward thinking, but eventually the Slate model of content delivered over the web became a standard. The same thing will happen to the Daily. Delivering content and tailoring it primarily for tablet devices will become the standard, not something special.

My challenge to Rupert Murdoch and “The Daily”

Make a version of the daily that lives in the browser on tablet devices. Provide the same native like experience of an app and own your user.  See which version is the better business after 6 months. (I’m only suggesting tablet devices and their browsers, NOT the traditional desktop with browsers there such as Firefox).

Use the Onswipe platform to take care of all the digital aspects of The Daily in the browser- making it work, delivery, functionality, and everything. It will be browser based and work on all tablets + smart phones out of the box. This is what we do at Onswipe and the process works the same for publishers whether they are personal bloggers or ambitious enterprises like The Daily. It’s robust and fully customizable. All the Daily needs to do is produce awesome content, which it is already doing.

I’m not a huge favor of being a paid subscription only, but I’ll give you the benefit of the doubt. We’re toying around with subscriptions paywalls. Outside of the processing fees, go ahead and keep way more than Apple will give you. Most importantly, get actual subscriber data. In the physical print world, having the data of your subscriber is very important. You get zero subscriber data with Apple’s solution. With Onswipe, you can get more data than you ever imagined on a subscriber.

What about the ads? The ads in the daily now are pretty awesome and a step in the right direction. We’re doing something even better that readers will love, advertisers will lust after, and The Daily will profit with. Ads have traditionally sucked on the web, especially compared with the beauty+elegance of print. Let’s combine that beauty/elegance with slight interactivity from the web.

I have an early early prototype of a web version of the Daily sitting in my hands as we speak and it rocks…


I don’t know what the future holds for The Daily. This is just the first version and there’s a fair chance they will overcome its shortcomings. Rupert is a smart guy, the content team at the daily is top notch, and I would not count them out.

Jason L. BaptisteFebruary 2011 

February 10, 2011 VIEW POST

14 Reasons Why You Need To Start A Startup

//This article originally appeared at OnStartups, where all my writing appears exclusively.

This post has been ruminating with me for a while. It’s not a sudden “a-ha” moment that made it form, but a collective group of “a-has!” over the past few months. Consider this the uplifting post to counter last week’s "The 11 Harsh Realities Of Entrepreneurship". Just because it’s a harsh reality, doesn’t mean you shouldn’t be an entrepreneur. The best time to start a startup is not tomorrow, not next week, and certainly not next year. The time is right now, at this very second.  Here’s why:

You Will Have The Time Of Your Life

I put this first, because it’s the reason that will motivate you the most to start a startup. Doing this may be hell at times, but boy is it fun. It’s an adventure that you will remember for the rest of your life whether things go very well or things go poorly. They used to say that everyone should try to be a rockstar at least once in their lifetime. I’m going to add to that and say that in-between being a rockstar and something else, you should be an entrepreneur at some point just for the adventure. Writing this article makes me realize how much I truly love doing this - the uncertainty, the victory, the failure, the connections with customers, the press,etc. I couldn’t see myself doing anything else and if this is truly for you, you will eventually feel the same.

You Have The Power To Create Something From Nothing

Few professions have the power to create something from absolutely nothing whatsoever. Right now, you may have some crazy idea in your head to bring into the world. It exists on some napkins, photoshop files, etc. right now, but eventually it will become reality. There’s a good chance it’s something that will have an impact on a large number of people… millions of people around the world. That wasn’t something many could achieve, even 20 years ago. Now, it’s possible for anyone, anywhere. I rarely use absolutes, since I know what that means, but I truly believe the ability to start a startup can happen anywhere. It’s certainly more difficult in poor countries, but it’s still possible. Look at Kiva.org or posts like this on HN.

A World Of Knowledge Is Available

It used to be a very old boys club or dark art, when it came to entrepreneurship. It used to cost a ton of money to go to seminars and buy books full of snake oil. It still exists, but people are starting to learn better. The experiences of previously successful and/or failed entrepreneurs are everywhere. They are on this very site, they are posted hourly on hacker news, daily on Mixergy, and found through smart people on Twitter. The blueprint to go from zero to paying customers and all the knowledge in between to guide you is out there in the open… for free.

Cloud Computing And Web Apps Make It Cheap To Start

Ten years ago it used to cost a lot to get started in terms of software+hardware. If you planned on doing anything with scale, you needed what equated to a front loaded CapEX of 500k to buy the equipment YOU might need. Software for internal collaboration costed a lot, with very few choices available. Software for actual development was even more costly. Now we have mature open source frameworks/databases and cloud apps. Startup Weekends occur every weekend and are possible due to this advancement in software. I almost feel weird writing this because we’ve taken what’s in front of us for granted. Amazon EC2 scales well, but now it’s even free to test out initially for your project. Of course, your time isn’t free, but even that is reduced with libraries+frameworks like JQuery and Ruby On Rails. Odds are, if there is something you need, it’s out there and available for free. If it’s not, there is probably someone to talk to.

Location Isn’t Important At First

I still think certain geographical areas have their place once you reach certain scale along with what type of business you are building (lifestyle vs. venture backed). In today’s day and age, you can START your company anywhere in the world and get great visibility. I’m seeing more and more companies come from random spots in the US along with international waters. Take a look at Balsamiq, WooThemes, or where Backupify originted (Kentucky!). The ability to access customers is available globally and you can run a distributed team due to the previous point listed above (cloud apps). Face to face time is always a good thing, but it’s a whole lot easier to book a flight once every 8 weeks than to pick up and move to 94306 right out the gate. If location is a worry for you, then don’t worry anymore. Don’t be pressured to race to the valley right away. If another geography makes sense, you will know in due time. You can start getting the most important thing right now, where you are… NOT funding… CUSTOMERS.

You Can Get Press And Attention Overnight

Getting press used to require an overpriced PR firm to the tune of $10,000 a month when getting started. Now a great product with a well crafted story can blow up overnight and get the attention of mainstream media+the tech elite. Take a look at Chat Roulette. Though it’s not a shining example of a great business, it is a shining example of the attention that a company can get press overnight.

There Are More Customer Acquisition Channels Than Ever Before

Getting customers used to be a really hard thing. It used to take a lot of money to make money. At scale, it certainly takes a lot of money to optimize an efficient sales machine with CAC, LTV,etc., but to get started, you can use a variety of customer acquisition channels. Public relations, inbound marketing, search engine marketing, in person events, platform distribution, direct sales, affiliate programs, and a ton more currently exist. They can be strategically used with little capital. Why does this matter? It’s like having more lives in a video game. Many of the channels won’t work out, that’s just life. If there are more channels, then you have more opportunities for success.

It’s Possible To Make A Living From A Startup Fairly Fast

It used to be that businesses would take years and years of losses to get to the point of making enough money to pay for you to live. If you wanted to do one, you had to raise a significant amount of capital up front, usually in the form of credit cards + savings from your job. In today’s day and age, it’s just completely different. You can start charging for software, increase your customers with a certain level of profitable scale, and get to the point that your barebones living is paid for. We also live in a subscription economy, where revenues are recurring. With things like churn aside, customers are now that gift that keep on giving. It won’t bring you riches right away, but it’s fairly reasonable for a team to create software and make a living within a 6 months period. Building a venture backed company is usually different, but lifestyle ISVs can sometimes morph into one. 37 Signals chose to stay independent, but if they wanted to do the raise money + grow fast show, they could have quite a while ago.

The Capital To Grow Is Widely Available If You Need It

The capital raising world is going through an interesting transitionary period. Since entrepreneurs need less to get to certain milestones, a new class of investors have sprung up, leading smaller and smaller deals. It used to be do a larger angel round or Series A, after having a lot of traction to get started. Deals took a while and the terms varied a lot. Now the spectrum varies heavily. You can get funding from YCombinator or TechStars at a ~18k level for just the idea+being a smart team, a $250-500k seed round in multiple flavors, a traditional larger angel round of $1,000,000, or the full Series A. I actually haven’t seen the full Series A as the first round of financing in a while, now that I come to think of it. A word of caution: many people think they should raise money, just because they see it in the press. That’s the wrong way to go about. You should raise money for a specific reason. In the case of the small ~18k YC round, it usually entails getting the first working version of the product out to get initial customer validation. Anything above that should be strategic to hit certain customer + traction milestones. If you don’t know what those are, don’t raise money yet.

Continue reading this awesome article at OnStartups

February 8, 2011 VIEW POST

9 Reasons Why You Need To Work At Onswipe

//This originally appeared on the Onswipe company blogMost companies get asked: “So why should I join your startup?” It’s a very very valid question. I figured it would be good to take the time out to explain why Onswipe is a great startup to join and try to translate the exact reasons why I love leading this team.

You Get To ReWrite the Rules And Help Make The Web Beautiful

The web is inherently an ugly place. We’re getting there with design, but sites with great design are far and few between in the grand scheme of things. With tablets, we get to rewrite all of the rules for the first time in decades. Think about it: publishers and content owners know they can start from scratch with design. They know design can be a lot like what the world has grown up with print design - beautiful typography, photography, and a personal experience. We won’t have this chance again for a very long time. The work you do with us will define the way an entire generation experiences the news and content itself. Many startups talk about changing the world, but few do it. We are one of those rare examples.

The Technical And Design Challenges In Touch+HTML5 Are A Blast

Building for the touch web and tablets in the browser is new territory for most. New interfaces will be created, new code that people can actually touch, and more needs to be created. A year ago the technology we’re building could not have even been done. The iPad didn’t exist and HTML5 was still in its infancy. In reality it still is, but that’s the fun part. The web will be your playground and you will get to tackle the technical challenges of making it an awesome place again.

We’re Going After a Big Long Term Vision

We’re in this for the long haul. When you get to meet us, you’ll here our vision and how mind numbingly huge it is. It’s going to take time and a lot of smart people like yourself. Money is the by-product of doing great things, so we’re not worried about smaller offers or building for a quick flip. We’re going to build great things and the money to build for the long haul will come. Reinventing the web and the media world is not a small mission. So many talented individuals join companies that may be successful, but the hunger and passion hits a ceiling. There’s nothing else in the world we could see ourselves doing for the next decade and beyond. Come help us reach those goals together, we can’t go it alone.

We’re Backed By The Best Funds In The Game

So what about money now? We’re backed by the best funds in the game with a deep domain expertise of media meeting technology.
  • Spark Capital, the original investors in Twitter, Tumblr, and Boxee.
  • Betaworks, who is behind bit.ly, chartbeat, and tweetdeck.
  • SV Angel, which is the fund where Ron Conway his investing. http://bhorowitz.com/2010/04/07/ron-conway-explained/
  • Morado Ventures, which is a fund started by Ash Patel and Mike Marquez. Ash literally built most of Yahoo! and was Chief Product Officer. Mike ran M&A for Yahoo! and later CBS Interactive. Their LPs are all early Yahoo!
  • ENIAC Ventures, which is a mobile focused fund. Nihal, their founding partner was an original angel in Admob, which sold to Google for 750 million
  • Jennifer Lum (through Apricot Capital), who was a very early employee at Quattro wireless. Quattro was acquired by Apple and is now iAd
  • Dharmesh Shah, the cofounder and CTO of hubspot. Dharmesh pioneered the use of content marketing and inbound marketing by
  • Roy Rodenstein, who sold going.com to Aol and has a deep understanding of the startup market. He is a close mentor and friend.
  • Wayne Chang, who cofounded i2hub, one of the world’s largest file sharing networks.
  • Waikit Lau, a former VC at General Catalyst partners, serial entrepreneur, and recently cofounder of Scanscout that merged with Tremor Media.
  • Techstars NYC, which took 11 out of 579 applications. That’s under 2%.
These smart folks gave us money so we could team up with smart people like yourself.

You Will Have The Time Of Your Life

We’re having the time of our lives. It’s a lot of hard work, but we love what we do everyday and do not take it for granted. We get to solve a fun new problem and have a great rapport. We work hard, but we also play hard. Working with us on a daily basis won’t really feel like work. We’re based in NYC, which is the city that never sleeps.

We’re An Experienced Team

There’s always a lot more to learn, but we’ve accomplished some cool stuff so far. Andres cofounded Grooveshark and I’m a professional author with the Penguin Group. We’ve also worked before on Cloudomatic, which was acquired. To be an entrepreneur, you have to love it and damn do we love this stuff. We’ve seen the early days of startup life before. We’re also surrounded by smart people that will help us along the way when we get stuck.

You Will Be Very Well Compensated in Cash and Equity

We are still a startup, but we know we need the smartest possible people in the game. People are the greatest investment a company can make. You will also have a long term vested interest in the company through equity. We’re building a large company and that equity will be worth something due to smart people like yourself. Also add in health benefits and Apple equipment you’ll need.

We Hope You Will Start Your Own Company One Day

The best companies in the world are those that foster entrepreneurship and create the next generation. PayPal is famous for the PayPal mafia. We hope that what you learn through working with us at OnSwipe will give you the knowledge and resources to start your own company afterwards. We have access to great people and we’re more than willing to share that with you. We sit next to you and we’re transparent. Our knowledge is your knowledge.

Help Shape A Great Culture

You will be one of the first ten at Onswipe. We are all going to shape a culture for the next thousand that join us over the coming years. We know it’s going to be a fun place and tackling great challenges, but in reality we need you to help shape it. You get to literally help build the place that you will be working at. Help us make a great environment, we can not do it alone.

Hiring is hard for startups right now and it’s clearly you who is in the position of power. I’m passionate about bringing in great people and writing is often the way for me to do it. Have more questions? Email me: j@onswipe.com or Call me: 772.801.1058


-Jason L. BaptisteCEO of Onswipe

January 28, 2011 VIEW POST

The 11 Harsh Realities Of Being An Entrepreneur

//This post originally appeared at OnStartups, where all my writing appears exclusively.

There’s always talk about the end game in the form of an acquisition, funding announcement, or eventual flame out. Hollywood has even made a movie about the founding of Facebook that glamorizes startup life instead of showing what it really is: a day in day out marathon of work with very little glamor. We rarely hear about the harsh realities that entrepreneurs face and the journey that this entails. This isn’t meant to be a downbeat and negative article, but actually quite the opposite. By knowing the harsh realities that lie ahead, you can be prepared when they come about so you can solider on. Here are some of the harsh realities that come with the territory of being an entrepreneur. roughroad

Your First Iteration of an Idea Will Be Wrong

The first iteration or implementation of your idea will often be wrong. That’s not because you’re not smart, not doing the right things, or some other reason to come down hard on yourself. As it turns out, this is actually a good sign. No idea survives its first interactions with its customers and requires you to synthesize feedback to adapt to the customer. You could be prideful, not listen to what your customers are telling you, and keep things the way they were. In the end, that just leaves you with no customers and a product you may not even use yourself. It’s okay if things change up a bit when it comes to your idea and its implementation.

Your Friends And Family Won’t Understand What You Do

"You’re an entrepreneur, so that means you’re un-employed?" or "Oh that’s nice." are some of the many reactions you will get from close friends, family members, and others over the course of starting your company. Even if you achieve milestones that are worthy of praise (customers, fundraising, new traffic levels, press,etc.) and denote success in the entrepreneurial world, people still won’t understand what you do. Unless you build one of the few consumer success stories that come around every few years, things probably won’t change here. The b2b space is even more difficult to explain as most people aren’t your customer, especially if it’s a niche workflow. This is okay and sometimes even a relief to know there is more outside in the world than just techies and entrepreneurs. Just because they don’t understand it, doesn’t mean you’re doing something wrong or unacceptable. I doubt Larry Ellison can have most of his family understand Oracle (that database company that stores information), but things turned out pretty well for him at the end of the day.

You Will Make Less Than Normal Wages For A While

If you got into entrepreneurship first and foremost for the money, then you are in the wrong business. Sure you may one day sell your company, but that day is probably far far away. Even then, there are usually earn out clauses, vesting still in tact, and a whole lot more. Even if you raise a good chunk of cash, your money is better spent on hiring the best talent than paying yourself a higher wage. There’s nothing wrong wanting to make money, but in the beginning it’s going to be rough. You will make less than most of your friends, especially the ones doing the “normal” paths of things like finance. It’s a litmus test in its finest form though. If you truly love what you’re doing, the capacity to have a large bank account takes a back burner to completing your mission. Sure you need some basic creature comforts, but luxury items almost seem silly as you will not have the time to truly enjoy them.

Everything Takes Twice As Long…If It Even Happens

Multiply everything by two, including the things inside of your control. When things take longer, you sometimes think that you’re doing it wrong or no one really cares. In reality, everyone else has multiple deals and responsibilities on the table. By factoring this into the expectations of your startup, it makes a lot easier to prepare for launching products, closing deals, and more. Also, be persistent and get the other party what they need as soon as possible. On the flipside, most deals just never work out. It may be an acquisition all the way down to a simple business development deal. There are always many moving parts and excitement that can just fade. That’s okay though. If you’re building your company upon one deal or a silver bullet (more on that below), then you need to re-evaluate things. Don’t be depressed when a deal falls through as that is just the nature of the beast.

Titles Mean Nothing. You Will Be a Janitor

Hey there Mr. CEO, Chairman, and Co-Founder! As a co-founder of a < 10 person company with a product that doesn’t have customers, titles really don’t mean much. Everyone will be doing a little bit of everything, including cleaning the toilets. Don’t try to mask the grind of being an entrepreneur with some superficial title. In reality, you should love and embrace the nitty gritty of those first days. Business cards are nice to hand out, but they really shouldn’t say more than co-founder or something else. Maybe someone inside the company plays more of the CEO role (speaking and being the face of the company), but that doesn’t really matter in the early days. You have to be humble and you have to be willing to do whatever it takes. You don’t have a staff of 50 to throw the task on to either. If you don’t do it, it won’t get done. Sure you could also try to optimize for efficiency, but that’s almost counter productive as the early days of a startup requiring doing so much, that it’s hard to just cut something out.

There Is No Silver Bullet

There shouldn’t be and usually never is a single deal that can make your company. Certain deals or customers can take you to another rung on the ladder, but there are still many more rungs to climb along the way. You shouldn’t look at a deal as the end game to the startup, but a means to a specific milestone that is in the near future. A deal can be taken away far faster than it can be given to you. By training yourself to diversify your risk and the milestones that advance your company, you control the destiny of your company, NOT one single partner. The success of a startup is the compilation of luck infused with many little wins along the way.

Customers Will Frustrate You

Having customers is a great thing, but dealing with support is a whole other ball game. If you’re in the consumer world, expect to deal with customers that don’t notice the obvious even with your fancy pants UI/UX in place. You will also get an influx of feedback that is often contradictory. One customer wants it in red, another wants it in blue, and a third wants it combined to become purple. The key to dealing with customers is to respond to everyone, but have a strong rule of authority. If you succumb to customers frustrating you and do everything you say, you quickly end up in a far worse position.

Continue reading this article at OnStartups…

January 24, 2011 VIEW POST

The Road Ahead: Why Tablet Publishing Is Transforming The Way We Consume Media

/* The following is a repost from the blog of my startup, OnSwipe. We recently raised a million dollars from great funds such as Spark Capital, Betaworks, ENIAC Ventures, Apricot Capital, Dharmesh Shah, Roy Rodenstein, and Wayne Chang.*/The title of this post is inspired by a book I read as a ten year old in 1995 by Bill Gates called “The Road Ahead”. It was a book filled with hope about a new frontier due to the large coming shift about to be caused by the Internet. Here we are 16 years later where another large fundamental shift is happening of even bigger proportions due to touch enabled devices. Here’s why we believe the way we create, consume, and share media is undergoing the largest shift since the creation of the printing press by Johannes Gutenberg in 1440.

Anyone can be a publisher

Publishing used to require a ton of capital and time. In today’s world, anyone with an internet connection can become a publisher. It doesn’t just mean blogging, but tools such as instragram, youtube, twitter, facebook, and more. It lets us give perspectives on a story that would not have been widely available before.

Publishing is way more than just articles in reverse chronological order

Blogging and publishing has often been about a reverse chronological list of articles. Time isn’t the deciding factor anymore, sharing and popularity is. Why should articles being shared thousands of times an article disappear off page due to a less important article?

Social is really a platform that was built for publishing

Social is a distribution channel that allows media and content to literally fly at the speed of light. One of the core philosophies of Facebook was information flow. Centuries ago it was measured in days, decades ago in hours, years ago in minutes, and today it is measured in seconds. The channels that exist due to Facebook and Twitter are the truly largest platform we have ever seen for publishing. We don’t need the paper delivery boy anymore, we have actual readers sharing and distributing content.

The new influencers

We look at the publishing market in three distinct slices. Personal publishing through Twitter or platforms of self expression like Tumblr, Large publishers such as the new york times, and most importantly a new breed of publishers - “The New Influencer”. They’re a group of individuals that are influencers on a specific topic tied to a valuable demographic. There is now a voice for every topic possible and it’s wonderful. It allows readers to engage with content specific to them, publishers to write on a topic they’re passionate about, and advertisers to target an audience that wants to hear from them. Our hypothesis is that we won’t see another large centralized news organization ever again, but a loosely coupled group of influencers across a broad range of topics. The next Hearst or New York Times will most likely look like the fusion of a media company with the heart of a well designed software company.

Serendipity as a recommendation engine

It’s not about articles that are similar, but articles that you may also enjoy. It’s about delivering an engine for content that provides that experience of bumping unexpectedly into content you’d enjoy, the same way you might find a great new cup of coffee while exploring New York City. You didn’t expect to get there, but you are sure happy you got there.

Design Is The Key To Winning

The key to winning on the web and content is beautiful design that is reminiscent of beautiful typography and design found in print magazines. The back-end is a commodity that the user will almost never see unless things fail. With touch enabled devices, the user experience and design is something we can touch. With great design, publishers can provide engagement levels that they’ve only dreamed about.

Touch Enabled Devices Are A Truly Personal Experience

We chose the name OnSwipe because the measure of interaction between computers and humans will no longer be measured by on click, but by on swipe. It’s just you and the device with a true one foot user experience. There are no barriers in the way such as a mouse or an extra two feet. The page itself responds to your emotion and excitement. The same bond that we’ve had with paper, we can have with our computing devices. It took us a while, but the “Personal Computer”, is actually personal.

Everything is mobile

Every device is connected and always on. Phones like the iPhone are connected everywhere and the 3G version of the iPad is outselling the wifi version. Our kids will grow up laughing at the fact we wouldn’t have Internet connectivity. What does this mean? It means there is zero delay in information flow. We can find out about news as it happens with zero delay and share that outwards. It also means content can be created from anywhere in the world. That is a double sided increase in the speed of information flow.

HTML5 Over Native For Content

Apps for content are a ponzi scheme, but they’re the only way right now to achieve beautiful design on tablet devices. The NY Times has so many app users because they’re using a centuries old brand to push traffic to multiple app stores. Why should publishers spend thousands upon thousands of dollars and time resources to develop across multiple platforms? It should just happen and with their existing traffic. With HTML5 and CSS3, we can deliver the beautiful experience of native apps using a publisher’s existing traffic. It’s time for publishers to have their cake and eat it too. This isn’t a geek argument of open platforms. It’s an argument of publishers being able to control their experience.

50 billion in media spend needs to shift

Mary Meeker estimates that 50 billion dollars of traditional media spend needs to shift online. Our belief is that it’s in a holding pattern and can’t. There’s a disconnect between award winning beautiful ads found in print and tasteless spam ads that litter the web. We think touch enabled devices can let this change by providing advertising people actually enjoy with the best of the web layered on- mobile, local, social, and more. The touch enabled web can let us create ads publishers want alongside their content, advertisers get returns for, and most importantly, that users will enjoy.

The rise of New York City as a collision point for media and technology

A lot has been happening in New York City over the past couple of years. There’s a great reason why we’re basing the company here and plan to be here for quite a while. Our belief is that design is the key to winning the web and the best design talent in the world is in NYC. It’s also an urban population with a ton of density where true use cases for mobile technology can be realized first. Ron Conway briefly hit on this with his belief in the urban entrepreneur. Lastly, the world of media is in this city and now colliding with the startup ecosystem. It’s a beautiful thing as media companies will start to absorb the innovation and fusion happening in this city. No city has to lose for the other to win. A city needs to find it’s specific strength and we think NYC has the strength of sitting at that huge intersection of media+technology.

The road ahead is a long one. One we’re dedicated to journey down over the next decade to transform the way publishers and advertisers deliver content to readers just like you. To help us along the way we’ve found great partners in Spark Capital, Betaworks, TechStars NYC, and a handful of angels that have been involved with companies like Quattro Wireless and AdMob since the beginning. It’s going to be a fun ride and one that we hope benefits everyone involved- publishers, advertisers, and readers.

Jason L.BaptisteJanuary, 2011 

January 14, 2011 VIEW POST

Why Every Entrepreneur Should Write and 9 Tips To Get Started

//This post originally appeared at OnStartups, where all my writing appears exclusively.

"The best part of blogging is the people you will meet"- Hugh MacLeod repeating wisdom from Loic Lemeur to me at the Big Pink at 2 am in South Beach after the Future of Web Apps 2008.

If you asked me to tell you a list of three of the best decisions in my life, I can certainly tell you that regularly writing is one of them. It’s the reason I’m an author here at OnStartups, made many new friends, had interesting opportunities cross my radar, and most importantly had the chance to share knowledge that has helped other entrepreneurs.

Why You Should Write

You Will Meet Other Smart People

Writing has allowed me to meet a slew of smart people. Some of these people are now virtual acquaintances and some are very close friends on a personal and professional level. Each article that you publish is a synthesized thought process that may click with other entrepreneurs instantly. Have you ever had a feeling when reading an article that “Wow, they are thinking exactly what I’m thinking”? By writing, you are likely to encounter a handful of people that experience the same thing. Occasionally one of those people will reach out to you via email or bump into you at an event. You might make a new acquaintance, a new co-founder for the future, potential investor, hire,etc. At the end of the day, being an entrepreneur is about finding other smart (hopefully smarter) people to collaborate with and writing frequently helps make this happen.

Example: I ended up becoming a writer here at OnStartups due to my own writing. A year ago, I put out an article called “Disruption and My Next Startup”. This is how I first met David Skok from Matrix Partners. David later introduced me to Dharmesh, who has become a good friend since moving to Boston. After talking about all things entrepreneurial, we realized we both had the same altruistic goals with writing: to meet other smart people and help share the lessons we’ve learned. Small piece of trivia: OnStartups was started in 2005 on Dharmesh’s birthday. I joined OnStartups on my birthday this year (September 8th).

Your Experiences Will Provide Insightful Knowledge To Other Entrepreneurs

Every entrepreneur has been through many of the same yet different experiences. We find co-founders, we all work at building a product/service, we all try to get customers, etc. Even though we’re doing the same thing at a high-level, we all have different experiences. We may have found great co-founders, built a great product, but fail to acquire customers. Each entrepreneur+startup mix is a unique permutation that varies from the rest of the world, hence providing a snowflake of experience. Through writing you can not only help share your successes, but also the pitfalls that lead to your failures. There’s no magic bullet to entrepreneurship, but the wealth of writing from experienced entrepreneurs out there such as Paul Graham, Dharmesh here at OnStartups, Jason Fried and Joel Spolsky have prevented young entrepreneurs from making mistakes that they might have made otherwise. Open source technology has helped entrepreneurs get started immediately with no capital while significantly reducing risk (you would have to raise a large amount of capital to launch anything with lines of code behind it a decade ago). I believe open source knowledge on entrepreneurship can help do the same when it comes to the business side of things. Getting as many entrepreneurs writing + sharing their insight is the very first start of this.

You Will Establish Domain Expertise

Every person is an expert in their own right at something. It might be user interface design, coding, leadership, raising money, investing, etc. By writing you get a chance to establish that domain expertise by sharing it with the world. Don’t worry about people stealing your secret sauce either. Famous chefs share their secrets and hints all the time without fear that it will cause their demise.

It Helps Build Dedication

Writing on a regular schedule takes a lot of discipline, just like going to the gym or practicing a new martial art. Nothing happens overnight, including building an audience and becoming a good writer. Like most things in life, writing takes time and strong dedication. Unwavering dedication is a valuable skill in startups that many seem to forget. If you keep yourself dedicated to writing on a consistent schedule, those important values will carry over to other facets of life including startups.

Your Communication Skills Will Get Exponentially Better

It takes a lot of work to become a great communicator as an entrepreneur. You have to break down complex problems, very technical solutions, and intricate details into soundbites that flow logically. By writing, you develop the ability to communicate more clearly to an audience of many, by providing a logical argument with a unique angle to your position. In some ways, you’ve been learning this skill your entire life through schooling, but writing as an entrepreneur in a public medium is something completely different. Through schooling you write for an audience of 1-2 people. Those people will usually judge you based not upon the content, but whether you agreed with their point of view. Writing as an entrepreneur in a public medium puts you in the spotlight of tens of thousands to millions of unique readers. If your writing isn’t cohesive, there are many that can call you out. I had some rough professors throughout my undergrad years, but no one will call you out like internet commenters, many of which may be trolls. By the third article, you start to subconsciously think “Is this cohesive/does it make sense?” as a gut reaction when writing in order to avoid negative feedback.

You Will Build An Audience That Will Give You Candid Feedback

If you’re really lucky, you will start to build an audience that isn’t full of trolls, but that consists of those that are genuine and honest. They may give you negative feedback, but it will be candid+honest. Don’t just look at the number of re-tweets on an article, look at the articles that get the audience to participate. You will eventually find a groove of what your audience enjoys and what they consider good writing. Try to reply to every comment as well, even if it is a simple “Thank you.”

It Is A Rapid Accelerator Of Serendipity

Startups are certainly impacted by luck, but I believe they are impacted just as much by serendipity. You never know who knows who or who you may run into at an event. By putting yourself out there and making yourself open to meeting as many people as possible, serendipity is much more likely to happen. Once you have even a minor audience, you are now likely to experience the effects of serendipity. One article might reach 500 or 50,000 people in a short span of time. Remember that we live in a world where content/information travels faster than ever before. Out of those 50,000 people, you never know who might be reading, who might reach out to you, or who might leave a comment. I can tell you this: The majority of good things that have happened to me in business can be traced back to my writing

9 Tips How To Get Started

Many think that writing is as simple as registering for a Wordpress/Tumblr/Posterous account and all of a sudden they’re the next Seth Godin. Just like anything in life, it takes time, practice, and finding the formula that works well for you. I started writing almost 2 years ago, but didn’t get into it seriously until approximately 3-4 months ago. Here’s a list of some of the things that I’ve learned along the way that will hopefully be useful food for thought.

Keep It Simple And Worry About The Aesthetics Later On

Sign-up for Posterous, Tumblr, or Wordpress. If you really want to customize things later on, host your own Wordpress install. Find a good, simple/basic theme, set up some basic settings + SEO, and get to the races with writing. Try to use your own name as the domain name. If you have a popular first+last name combo and can’t own your exact name, try to get something similar. Last, but not least, try to have a picture of yourself somewhere on the site. It’s good to put a face to your writing and this will help people identify with you when meeting up in person. Besides the simple stuff above, just start writing. Insightful content is king and that’s where you should be focusing your efforts.

Continue Reading at OnStartups

December 22, 2010 VIEW POST

11 Ways Your Startup Can Deliver Support That Will Increase Sales

//This post originally appeared at OnStartups, where all my writing appears exclusively.

upport is often an after thought for many startups in terms of the impact it has on your time, sanity, and development resources. It’s usually a tedious chore that is a second class citizen. Or…Maybe it’s not. Maybe your startup worships at the altar of Zappos. If you do, odds are the influx of support hits you from out of nowhere like a sucker punch. Here’s what I’ve learned about preparing for support, how it decreases churn, and increases sales.

Pre Sales Support Will Bring Up Patterns Of Lost Sales

Everyone seems to think that their funnel and their website copy is absolutely awesome. In reality, it comes down to not knowing what you don’t know. There are usage patterns that will cause confusion amongst potential purchasers of your product, that you could have never imagined. By implementing a strong pre-sales support system, you will start to gain pattern recognition into what is causing you to lose sales. The best way to catch these issues is to implement live chat systems like Olark, a phone system like Grasshopper, or a simple pre-sales FAQ.

Example: With PadPressed, many potential customers wanted to see a working demo on their iPad. We thought we had this clearly stated on the Demo page. As it turns out, we didn’t. After five requests in a day, we realized that we needed to heavily emphasize the working demo portion in the copy. We modified buttons on the homepage and we highlighted the links to the live demos on the Demo page. It worked. There have been more clicks and more requests about this.

Build As If You Have To Support It

I’m stealing this quote from Kevin Hale of Wufoo, but it’s truly one of the most important product focused quotes I’ve heard over the past year. Whenever you want to add a feature, especially the nifty ones that may be confusing or buggy, think about the impact that will have on support. Also think about a feature’s implementation and how it plays into cross platform compatibility. For every feature you plan on adding, expect more of the following:
  • Extra support ticket requests ie- Each feature will bring about way more support tickets that require more time, which is something you’re already strapped on.
  • More pre-launch documentation ie- You will have to spend more time on Q&A, writing documentation, doing tutorial videos, etc.
  • More complexity in your sales and/or fundraising pitch ie- Your cool new features have nothing to do with your simple problem/solution statement.

Triage Critical Requests Post Launch and Freeze New Dev

After every launch of PadPressed, there are usually one to two specific problems that are major issues. For our most recent launch, the timthumb library was being wonky with Wordpress MU + external images. Instead of adding some of the new things we had planned, we had to focus solely on releasing a major update for this issue. The adrenaline from a successful launch will lure you into wanting to do more “cool stuff” for customers. In reality, if you don’t double down on getting past the critical bugs, they won’t be customers for long.

The Knowledge Of The Customer Community Will Save You

If there’s a way to create a customer support forum, I strongly suggest it. It could be something like GetSatisfaction or it could be a private forum. Most problems that customers would normally open up a ticket with you for, will have been solved in the past and publicly available in the forums. I suggest that all tickets are made public and viewable by users. Another benefit of having a great community is the fact, that other customers will help out new customers and give suggestions. The math adds up over time. Here’s some math:
  1. Assume each support request takes an average of 15 minutes to deal with.
  2. You have a total of 400 support requests per month.
  3. 50% of those support requests could be solved by having past knowledge public. (200 total)
  4. That’s a total of 50 hours a month, which adds up to a lot of saved time, energy, and frustration.

Support Is A Reason To Charge

Support is a reason to charge, especially when dealing with a freemium model. As geeks, we may be able to do everything ourselves, but in the real world, most normals love to have their hand held or have someone on call to help them. You could charge for premium support or you can even bake it into your price. Apple’s genius bar and training programs seem free to customers, but they’re actually a good reason why Apple products command such a premium. Look at Zappos as well. They spend good money on providing a first class support experience and it’s why they’re able to do so well. Once again, THEY SELL SHOES. The support experience has allowed them to command a dominate spot in the market and differentiate themselves by selling shoes. Apple and Zappos’ models are indirect ways to charge for support. Many open source and freemium companies charge directly for support and make big bucks doing it. Some may say that this model doesn’t scale, but I say baloney. We’re a connected and distributed world where there is an infinite amount of labor on demand to help with support.

Escalate With Discretion

As a startup with strapped development resources, escalating issues to the development team requires a certain graceful balance. Certain critical issues and larger customers require you to bring issues to the attention of the core dev team. The problem is, attending to these issues can slow down new development and an already large onslaught of bug fixes. This is also another area where you can charge for a more advanced level of support.

Continue Reading at OnStartups

December 6, 2010 VIEW POST

How I Pitched @TechCrunch And 13 Ways To Get Press When You Launch Your Startup

I outlined 16 must have customer acquisitions techniques for startups in a post last month. One of the most important techniques comes in the form of Public Relations and I think it’s important enough to warrant its own article. PR is how you launch companies, build buzz, and get valuable attention that ranks well above the noise of buying advertising. For example Apple only aired the 1984 ad once, but received over five million dollars of free publicity due to everyone talking + airing the ad again on the news. Like anything worth striving for in life, getting attention from the press is hard, but if you attack it with the right approach, it becomes fairly easy to do. We’re launching a new version of Padpressed later this week and I thought I’d share some tips I’ve learned over the years.

A lot of entrepreneurs ask me how I got on TechCrunch with PadPressed, so I included the exact email I used to pitch and get on TechCrunch at the end of the article with some notes.

Tell a Story

The goal of a journalist and blogger is to engage readers and get more views/subscribers. Something boring certainly won’t entertain the readers, so why would they write about it? Journalists are also in a position of power. They have hundreds of startups pitching them everyday and vying for attention, so you need to stand out of the crowd. The best way to do this is to tell a story that will transfer from (a) your mouth to (b) the journalist’s keyboard to (c) the reader’s eyes. If you can tell a story that intrigues and grabs people, journalists are far more likely to write about you, as it will drive adoption of their product.

Be Prepared Technically

Things spread fast in this day and age. Even if you’re not actively pitching, once you’re out in the wild, anything can happen. Articles can’t be re-written and you only have one shot at first, so make sure your app can leave a good impression. Around the time of launch, allocate more resources than normal in terms of hardware. This is so much easier to do now vs. five years ago due to Rackspace and Amazon. Also be prepared the second you give the story to someone as embargoes will most likely be broken in this day and age. You don’t want major press coverage to give a negative impact to users.

Segment Your List

You need to segment your press list depending upon the exact angle and topic of the publication. For example, with PadPressed, we’re approaching all the following segments of publications

- Traditional Tech Blogs- Well known bloggers who could use the tech- Wordpress Publications/Blogs- Apple/iPad focused blogs- Media/Publishing Trade Specific- Traditional media looking for iPad stories

You also need to adapt the story you tell and the pitch that you give according to the outlet you pitch. A Wordpress blog should be approached much differently than a traditional media publication like the Miami Herald or San Jose Mercury News. It’s the same way pitching different companies and departments on a sale vary.

Give A Taste Of The Future

So when we pitched TechCrunch, we didn’t pitch it as a WordPress plugin company. That’s just not big news and though it’s a very cool, it doesn’t provide excitement. We gave a taste of the future of being available to All CMS’s, a hosted platform, and helping pave the way for the future of media via tablet publishing. Don’t talk too much about the future, since you’re not there yet, but give a glimpse into it. It also makes setting up future stories a whole lot easier. Once you reach those milestones, it gives the journalist something to refer back to and segway into the next article.

Be Brief

Keep your pitches short and make sure the basic gist fits into the first glance of a GMail subject line. Bloggers get way too many pitches on a daily basis and they need to get the gist of what you’re trying to do almost immediately. If THEY can’t get it in a few sentences, how are there readers ever going to understand what the product does?

Give All Links To Detailed Resources

Not being contradictory here, but complimentary. Keep the actual pitch email very short and to the point with a call to action. For more detailed information, link to it inside the email and make it apparent. ie- not thrown as a random obscure link.

Founders > PR Firm

It’s always better to have founders pitch a product than a PR firm. Yes, at some point, you may have a corporate com department, but for the most part, you are a small company whether or not you have a track record. Journalists also get a bit of an ego stroke when they deal directly with a founder (in a good way). It means a lot to them when an actual founder reaches out and takes the time to answer questions/deliver a pitch.

"Speaking of that and a heads up, some of the major Hackers & Founders meetups will be hosting the first in a series on how to get PR for your startup - with panelists from the founders who’ve done it, the reporters who cover them as well as the agencies who work with early stage companies. Shout out to Dave Ambrose on the Hackers & Founders Twitter handle for more updates when we do the event in November.”

Give direct Contact info and be quick

Most stories will go from pitch to print fairly fast in online media. Traditional print takes a bit longer, but even then, it can happen fast. When a journalist is on a deadline, they need to get the story done on time. If you can’t deliver fast enough, then you’re cut out. Give your direct contact info and during the launch period, make sure you are always around to answer questions. You should also give priority to whatever they need to get the article out - screenshots, giveaways, further facts,etc.

Ride a Wave

The best way to get press attention is to ride the wave of an already big trend being talked about. In some cases, you get an article solely featuring you or you may be part of a larger article on the topic. This often happens with iPad and iPhone apps or the trend of cloud computing. When I launched my first project to the press, we specifically aimed it at eBay raising their fees. The Associated Press picked up on it, resulting in coverage in USA Today. Here’s a throwback to my past days in the press.

Try to Make A Connection Beforehand

If you’re in the tech sector, especially in Silicon Valley, odds are you spend a good amount of time at events and conferences. Bloggers/journalists get paid to go to these events and are often there as well. Don’t go into a full on pitch, since you’re probably not ready for press coverage. Do try to make a personal connection beforehand just so the intro is warm when you are finally making a pitch.

Exclusives Can Help But Are Tricky

TechCrunch and other blogs often like to get exclusives, but it also hurts your chances with other blogs. Certain launches have certain goals. Is it to reach a specific audience? Is it to have the widest distribution and buzz? Is it to cause potential partners/acquirers to jump? Exclusives are like the super power up that you can only use once per level in a video game to kill a specific boss or opponent. Make sure you use it for the right purpose and at the right time.

Don’t Copy/Paste

For the love of God, do not mail/merge or copy/paste a pitch to a journalist. Yes, you can re-use some parts of the pitch such as what you do, but keep things at a personal level. You may have to type 100 emails, 50% of which don’t even get a response. That’s called having to hustle. You would think it’s hard to tell if something is copy/paste, but a good journalist can see right through it. No personalization, vague statements, etc.

Follow Up

First off, don’t pester journalists if they don’t want to cover you. It’s nothing personal and everyone makes bad judgment calls. There’s just not enough time to properly cover all the startups. If they DO show interest, make sure you’re on top of the ball. If they forget to followup, make sure you get them the info they need and get the article to press. Getting a piece of press coverage is A LOT like making a sale. Not following up on a warm sales lead is foolish and so is the same with a journalist.

Offer Something To Readers

If you look at many of the successful launches on TechCrunch, they often offer some NONMONETARY giveaway, usually in the form of early invites to the service or a limited number of free premium accounts. This isn’t bribing, this is adding utility to the readers of the publication. One goal of a writer is to provide utility to their readers. By offering access to an app that is hard to come by elsewhere, the story certainly provides utility.

Stunts Can Be The FireStarter

Stunts aren’t a sustainable way to do press, but they can certainly get the momentum going for a company. One of the most famous examples to this day is Half.com renaming Halfway,Oregon to Half.com. AirBnb happened to do the same thing by selling cereal during the presidential elections of 2008 (Obama O’s and Cap’n McCains). You need to find a way to rise above the crowd and be a proverbial Purple Cow. Once you have the spotlight on you with massive attention it makes it a lot easier to get attention in the future for more mundane things such as product launches.

Leverage Your Contacts

Odds are someone you know, knows someone at a press outlet and can give you an endorsement. Being backed by the right angel or VC can be insanely useful as well. YCombinator companies are able to get tons of press due to the sheer network and validation of being part of YCombinator. Doing partnerships with other companies is also another way to leverage your contacts and network. By doing a partnership with an already recognizable brand, you increase the likelihood that a press outlet will take a liking to your pitch.

Example PR Pitch Email To TechCrunch

This is the exact email I sent to TechCrunch when we launched.  Nothing was omitted, including my personal info.  Feel free to say hi :)


Subject: Exclusive for TC: Launching Padpressed- make any blog feel like a native iPad app

Hey Mike,

Launching PadPressed tomorrow at noon EST and TC gets free reign on an exclusive before then. PadPressed makes any blog look and behave like a native iPad app. We’re talking accelerometer aware column resizing, swipe to advance articles, touch navigation, home screen icon support, and more. We’ve built some pretty cool tech to make this happen smoothly, and it works with your existing layout (iPad layout only activated when the blog is accessed from an iPad). Okay, I’ll shut up now and you can check out the demo links/feature pages below, which are much more interesting than my pitch.

PS- Would also be happy to do giveaways to TC readers. Thanks again and feel free to reach out if you have anymore questions (skype,phone,etc. listed below).

Video Demo: http://vimeo.com/13487300 Live demo site (if you’re on an iPad): jasonlbaptiste.com Feature overviews: http://padpressed.com/features My contact info: j@jasonlbaptiste.com , Phone: 772.801.1058, Twitter: @jasonlbaptiste, Skype: jasonlbaptiste

-jlb772.801.1058You Should Check Out JasonLBaptiste.com


Some notes:
  • Gave TC the exclusive due to the goal of getting a large reach and seeing if there was enough demand to further the project.
  • Highlighted what it did in one sentence with key features following thereafter.
  • Highlighted the tech behind it so this seemed special.
  • Added in giveaways.
  • Most important part:  direct links to the exact resources they would need, including my phone number.  Mike emailed back soon thereafter and Alexia called an hour after.  The article went from pitch to being live in < 5 hours.
  • Update:  I added in the subject I used.  I literally spent close to an hour on it, email testing it.  I would send myself emails using the subject line to see how it would appear.
All of the above are important, but the one that will carry over to other aspects of your startup happens to be - “Tell A Story”. If your startup can tell a story, then you are far ahead of the curve. What PR tips have been the most effective for you over the years?

October 18, 2010 VIEW POST

Answering The “Should I Go To College/Drop Out?” Question For Young Entrepreneurs

There’s a common question brought up in the entrepreneurial community that goes something like this: “Should I go to college?” or “Should I drop out of college?” It’s even the subject of a good analysis by Vivek Wadhwa over at Techcrunch. . I’ve seen the question pop up often enough, it’s certainly an important one, and a question that I have a lot of personal experience with (I went to college, started a company, “stopped/dropped out”, and eventually went back to finish my undergraduate degree). By no means am I 100% right on this subject, but hopefully this serves as some guidance to those struggling with the question themselves.

Short answer: Yes, you should go to college. Here’s why and some tips on how to maximize the experience + prepare yourself for a startup.

Meet As Many Smart People As Possible

The great part of going to college comes in the form of all the people you will meet from different and diverse backgrounds. There are always “How do I find a co-founder?” posts on Hacker News and across the internet. Going to college can usually result in finding a co-founder for your company on the technical and/or business side of things. It’s where Tony from Zappos met his co-founder along with numerous others. You will also make friends that might later make it into the startup game, and be useful for you to connect with. On top of it, you get to interact with people who have absolutely nothing at all to do with technology, but can give you insights into experiences you never knew existed (different backgrounds, career paths, countries,etc.) Go to college and meet as many people as possible.

Study Subjects That Are New And/Or Challenging

I think the biggest reason I wanted to leave college to do a startup full time was due to the fact that I just wasn’t excited by the subjects and courses being presented to me. Yes, it can’t always be fun,but there should be SOME enjoyment in it. Even when I went back to finish by undergraduate degree in CIS at UMiami, I just didn’t enjoy the subject matter. The Comp Sci courses used dated technology and the business courses had no appeal to the startup world. What course did I end up enjoying the most? A Caribbean Literature class. If I could go back, I probably would have studied something such as Journalism or writing, with a minor in Comp Sci just to get the core fundamentals down. You get four years to go learn as much as you want. Go find something challenging, otherwise you will gravitate towards leaving school.

It Shows An Ability To Finish Something

There’s something to be said about those that finish what they started. It shows an ability to see something through to the end and finish something you may not fully enjoy. I think that’s one of the primary reasons I decided to finish: “I wanted to finish what I started and build some character through doing that.” Startups are a marathon race and a good portion of them fail, just because the founders decide to give up / not finish what they started. That’s with something they ENJOY. Showing that you were able to finish a four year degree shows some ability to complete tasks and “sticktoitness”.

Start Projects, Not Companies While In School

This will probably be the subject of another post, but there is a huge difference between a project and a company. A company requires hiring a good amount of people, a fairly big long term vision, and scaling to meet customer demand. With projects, they start out as hobbies, get tested with the market, and might eventually make some good money with product/market fit. They also tend to be smaller and can be run by 1-2 people. It’s possible to manage a project and take a full course load. Look at it like a very serious extracurricular. Best of all, you can try a bunch of different things and learn a whole lot along the way. You won’t have to raise any capital either. A full blown company? It’s just not humanly possible. Running a startup takes 12-14 hour days, an insane amount of stress, and putting the well being of employees into your hands. You can’t manage that AND do well in school. You will most likely end up half assing most.

If Something Takes Off, Seriously Consider Stopping Out

So what if one of your projects really start to take off to the point that it’s not possible to contain growth? Consider what the Facebook founders called “stopping out”. It’s the equivalent of taking a sabbatical to focus on the company to see it through to an exit or failure. After that point, you can go back to school and finish what you started. This way, you’re able to fully focus on your startup and not let your grades drop. Great schools will usually give you a few year window where you do not have to re-apply. This is what I did with my first real startup and I still think it was the right move. Sadly, things ended up failing, and I returned to school to finish what I started.  Peter Thiel might even give you up to 100k to do this.

Use The “I’m A College Student” Card As Much As Possible

Want to go to conferences for free, get important people to pay attention to you, discounted software, and a whole lot more? Use the “I’m a college student card.” It gives you the ability to save money and get access to some people that want to just help you out. In some ways you may feel that it undermines your credibility. I often felt that way, but looking back, that was just foolish pride. If you’re good, you’re good. Some people will be even more impressed that you’re that good and a young college student.

Don’t Waste Money On An Overpriced College

Unless it’s a school that’s great for what you’re trying to study, has a great faculty, or one of the few schools worth their name, don’t rack up debt on an overpriced school. In California, UC Berkeley is a great school with low tuition. The same can be said of University of Florida in Florida and numerous other areas. I read that Stanford gives a full ride to families that make < 100k. Olin College also gives half scholarships to everybody and makes sure that the rest gets taken care of somehow. That’s how college should be. 50k+ a year tuition/room+board being covered by student loans is no way to live.  It’s also a huge burden to bear when you need to have a low personal burn rate when out of school.

Try To Go To College In a Startup Hub

It’s funny, I didn’t get into Startup culture until I transferred to UMiami from Boston College after my freshman year. All the resources I needed in a startup hub were ironically already in Boston. If I could go back, I would have stayed in Boston (either at BC or a more engineering focused school in the area). Going to a school in NYC or the SF Bay Area is also desirable. You get to go to college AND start making a name for yourself in the community early on. You also get access to all of the events (at a lower price due to student status), network with everyone, and build connections.

Organize Events With Other Students

If you really love startups, you should start organizing student events for other hackers+founders at your University. We’re a rare breed and bringing them together while at college is a good way to make new friends. It’s also a way to get important people to pay attention to you. Try doing something like this: Organize some group/club/event for students at your school, get some decent following, then invite important people to do roundtables/speak. You will now have a personal connection to them and I doubt they will say no. People love helping students.

Read As Many Blogs As Possible

Ever since I got into the startup scene, I started reading as many blogs/books/publications as possible. Everything from industry news to tech/business analysis. You should also spend a lot of time with communities such as hacker news as well. Consider this reading like “another course”, just without the tests and crappy lectures. There is a wealth of information out there and people willing to share what they’ve learned. If you’re a student and reading this article right now, this is just one example.

Ignore Edge Cases And Sensationalist Success Stories

The flipside to reading to many blogs happens to be this: “Everything seems like it’s so easy and you wonder why the f**k you’re in college, when you could be worth $60 million.” Ignore the sensationalist stories and the success that seems like it came overnight. It’s all difficult whether you are in college or not. It takes a lot of hard work and there’s a chance you will fail. Use college as a way to start projects and learn as much as possible. If for some reason, something takes off, then consider going full time with it. Don’t start trying to use college as a scapegoat for not being on the cover of businessweek.

Learn As Much About Product AND Customer Development As Possible

After my first project failed, I learned I needed to know more about tech + product development, so I set out to learn that over the next few years. I finally learned what makes a good product, how to code at a rudimentary level, ui/ux skills, scaling architecture, etc. It took a long time, but was well worth it. THEN I did my first real startup - Publictivity. We failed not because the product was bad or that people didn’t want it, but that we hadn’t built any sales/marketing channels. By the time we were ready to launch, the recession hit, we ran out of money, and things went down fast. I realized I needed to learn about marketing/sales channels just like I learned about product development. So I went back to school and spent as much time as possible learning about distribution channels+customer acquisition. If you can come out of college understanding how to make a great product that people want and the channels to distribute that product to customers, you’re in good shape.

A CS/CIS Degree Will Build A Good Foundation

Once I got into entrepreneurship, I changed by business degree focus from Entrepreneurship to Computer Information Systems after realizing entrepreneurship was best learned from practice. I decided against a full blown CS major since I was so far into the business core at the time. The CIS program seemed like a good compromise. I knew some programming at the time, but I didn’t have the academic fundamentals. I learned a lot about the basics of computer science, programming, database design, and other things you might not get from building your own products. I’m sure I’d be okay without them, but I’m really glad I have them.

Be Wary of Business Programs

If you’re into the startup scene, you’re probably going to want to avoid the business courses at your school. They’re usually designed for physical businesses or large fortune 500 companies. Some of the basics such as accounting/law are good, but there are other more efficient ways to learn the basics you need for a startup. I found that I’d often be frustrated and start saying to myself: “Why am I learning this stuff? It doesn’t apply to my specific sector of business.” It’s the same way Steve Blank says an MBA isn’t really useful for entrepreneurship/early stages of a company. MBAs were built for a different stage of a company than the startup phase. A lot of the education in undergraduate business programs are built for the same phase. Really dig in deep to the exact curriculum. Case studies are also a good way to learn in my opinion. Each school varies and some are great.

Spend Senior Year Preparing For a Full Time Startup Once Graduating

Spend the last year of college really thinking about what problem you might want to solve with a startup, full-time once you graduate. If you’ve been doing projects along the way that have been profitable, start hoarding cash like none other so you can sustain yourself for 6 months+ after graduation. Start talking with all of the connections you’ve made and start doing customer development once you know the problem you want to solve. So to re-iterate, here’s how I would go about senior year if you know you want to do a startup full-time afterwards:

1) Start making a list of big problems that you want to solve and think need solving.2) Start narrowing them down by talking to smart people.3) Start doing an MVP + customer development around the idea.4) Make sure you’ve been hoarding cash from any consulting, jobs, projects,etc. that you have coming in. Prepare to live like a college student afterwards too. 6+ months is usually a good amount to have in the bank.5) Towards the spring, start applying to YCombinator and programs like it with the concept you’ve narrowed down to. It’s hard to get in, but if you do it helps. If not, continue onwards. If failing to get into one of these programs “stops you”, then you weren’t meant to be doing the startup in the first place. You will get rejected many many many many more times, so get used to it.6) Prepare to have a hard-working yet fun summer. Welcome to startup life.

Have Fun. You Won’t Realize What You Had Until It’s Gone

Life is so much easier as a college student. I wish I could go back and do it all again from the start, following a lot of the things I’ve outlined in this article. I jumped into startups at an early age and lost a lot of the “normal college social life” aspect too. When I went back to finish undergrad, I also had nothing, but the boring courses left. Go have fun, meet as many people as possible, learn new things, and prepare yourself to do a startup full time after you graduate. Just because you went to college doesn’t mean you won’t be Mark Zuckerberg. He just happened to start Facebook when he was in college. If he started it his senior year or a year out of school, he still might have done just as well.

Three years ago, I may have had a completely different perspective on this question. The education from mundane subjects and getting a piece of paper are the least important parts about college. It’s the combination of smaller, more important details that matter. At the end of the day, you can still be a successful entrepreneur without a college degree. There is zero doubt in my mind about that. It’s really about life chances and giving yourself as many advantages as possible. The college experience is one of them and you should at least give it a try. If you’re a current college student or thinking about whether you should go, feel free to email me . I would love to provide any help/advice/more insight that I can.

September 30, 2010 VIEW POST