Jason Baptiste


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14 Ways To Be A Great Startup CEO

By Jason Baptiste on December 28, 2010

great startup ceo mark zuckerberg resized 600Everyone 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?

You Should Follow me on Twitter: http://www.twitter.com/jasonlbaptiste, Friend me on Facebook: http://www.facebook.com/jasonlbaptiste, Email Me: jbaptiste@onstartups.com, or even call: 201.305.0552

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

By Jason Baptiste on December 6, 2010


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. michael jordan entrepreneur resized 600With 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.

Find Strength In Your Weaknesses

More and more, I'm finding out that my weaknesses are my strength. Weaknesses can be identified and attacked. If your company has a hole in its team, business model, or customer acquisition model, you can attack it head on. Find your weaknesses and figure out how to attack them in order to make your company stronger. It's simple: the less weaknesses you have, the stronger your startup becomes.

Be motivated by your pain

Some athletes hit their high points when they reach the area of most pain. The pureness of facing the most difficult parts of your journey should be the most rewarding as they allow you to level up. When Facebook first started in the college market, they didn't go after the schools where they could gain market share the easiest. Instead, Facebook actually went after universities where they would experience the most resistance and have the most pain ie- schools with existing social networks. If they could conquer this pain, they could easily conquer everything else.

Treat entrepreneurship like a privilege, not a right

I'm lucky to live in a country where entrepreneurship is something that anyone can get into. Many people often forget that other countries are not as lucky and have oppressive governments. We often talk about entrepreneurship as a way out of poverty, but this isn't even possible in some countries. Don't treat this as a lackadaisical experience. Many people would literally kill to be an entrepreneur, because it meant their survival. Be grateful for the opportunities you have and never take it for granted.

You must work for it every single of your day

Work/life balance is important, but there is no off switch for being an entrepreneur. You can't just turn it off and come back to it 3 weeks from now. If you really want to do this. If this is your destiny, which for many many people it just isn't, then it is something you have to keep at every single day of your life. Some are lucky enough that their first thing takes off. Your first, second, or even third thing might not take off. Stick with it and keep working at it every single day of your life.

Do not make excuses

Accomplishing something is a binary outcome. You either accomplished it or you did not. A lot of the times the end result will be the former, but don't sugercoat it. It happened for a reason and don't make excuses that act as scapegoats. Face success or failure head on. We often associate excuses with failure, but I think they can also be present in success as well. Though it's good to be humble, you shouldn't also make excuses for your success. Realize your what you did right and the hard work associated with it. Excuses are exactly just that- excuses. What other athletes and sports references have helped you become a better entrepreneurship? Instead of Michael Jordan, who might you pick and what has been their advice?

You Should Follow me on Twitter: http://www.twitter.com/jasonlbaptiste, Friend me on Facebook: http://www.facebook.com/jasonlbaptiste, Email Me: jbaptiste@onstartups.com, or even call: 201.305.0552

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