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14 Ways To Be A Great Startup CEO

Posted by Jason Baptiste on Tue, Dec 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:, Friend me on Facebook:, Email Me:, or even call: 201.305.0552

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Get Help Starting Up: Win A Free Scholarship To StartupToDo

Posted by Jason Cohen on Wed, May 19, 2010

I've run three startups, and every time it felt more like stumbling around in the dark than confidently striding along a path.  Most everyone I meet feels the same way.

It's worse the first time around of course.  You read blogs and books, you take other business founders out to lunch, and you join entrepreneur support groups (I mean, meet-ups).

But still.  There's like 1,000 things to do, none of which you've ever done before or even seen before, and certainly nothing any school has prepared you for.  What about all that stuff?

Bob Walsh, author of several startup how-to books and the Micro-ISV blog and podcast, has all the answers at StartupToDo -- a combination web application, guidebook, and community for startup founders.

And better still, here at OnStartups we're giving away 10 scholarships, so you get all this love without paying a cent!  Even if you don't get the scholarship, however, check it out.

Here's how StartupToDo works.

First, there's already 50 guides walking through every aspect of a business from deciding on a name to selecting a web host to Google AdWords to creating your elevator pitch, .... you name it.

Second, as you progress through those guides -- in any order you please -- you can watch your progress exactly like a burn-up chart for software development:

Startup burn-up chart

This makes it easy to ensure you're making steady progress on important areas of business while you tend to the obvious fires and daily chaos.

Third, the guides aren't static -- it's more like a Wiki + comment system so you can also learn from everyone else on StartupToDo who has gone through that guide.  So it's a living, breathing lesson and checklist, not just some stale prose from 1994.

Fourth, there's amply opportunity to not just go through guides but to interact with other founders through things you've heard of (e.g. forums) and brand new things (e.g. "What do you think of my website" system).  Now you're not just guessing by yourself -- you're part of a thriving, intelligent community of people just like you, helping each other get through the pain and thrill of running your own company.

Ever need help answering questions like these?

1. Which online service should I use for what? Creating your online infrastructure - from Google Apps to finding the right service to monitor server uptime - there's a variety of online business services you need to put in place in order for your startup to succeed. Guides turns finding the right services into tasks that take minutes, not hours and days.

2. Does my web site work? With their Site Reviews, you tap the power of the community to get quantitate and qualitative confidential feedback on how well your site explains your product, connects to the visitor and influences their decision making.

OK ok, so now you're convinced it's really useful -- and worth paying for -- but it's even sweeter if OnStartups treats you to an account, right?

We're going to give away free 6-month subscriptions to (valued at $105).  To be eligible, you need to do just three simple things:

1) Visit OnStartups on Facebook

2) Hit the "Like" button (needed, so you can post a comment)

3) Leave a practical tip or ask a question about starting up.

Or, if you'd rather use Twitter than Facebook:

1) Provide a practical tip or ask a question about starting up and append @onstartups to the end so we can see it.

We'll be giving out a free, 6-month subscription a day for the next 20 days.

So, lets see those comments and questions.  Good luck!

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Startup Success: The Phenomenal Force Of Focus

Posted by on Wed, Nov 22, 2006

If you’ve been doing any amount of reading about startups (or for that matter, business strategy in general), you’ve probably heard at least a few times how important it is to focus.  I find it interesting that though there is general consensus among successful entrepreneurs on this topic (i.e. focus=good, lack of focus=bad), the advice to focus continues to be hard to follow.  I’ve struggled with this challenge myself, even though I know how important it is to focus.

This past week, the topic of focus came up again in discussions with a startup team that I’m involved with.  Brian Harrington and Josh Lesnick are the co-founders of a cool new startup here in the Boston:  I’m In (disclosure:  I’m an advisor to the company).  After months of development, the I’m In team launched their consumer product last week.  I encourage you to check it out.  Their offering allows for the creation and coordination of gender-based trips.  For example, you and a group of your guy buddies from grad school want to coordinate a ski outing.  Or, you and the gals want to coordinate a New Years party in Vegas.  The idea is interesting and the user experience is pretty slick.  Create your own group and try it out. 

But, this article is not about I’m In the company, or its product.  It’s about focus.  I asked the co-founders what big lesson they have learned now that they have a product out there.  Their response can be paraphrased as follows:  “Focus!”.  But, if it stopped there, it wouldn’t be particularly interesting.  So, let’s take a look at why focus is important andwhy it’s just so hard sometimes to focus.

The Phenomenal Force Of Focus
  1. The Temptation Of The Big Market:  Because software is so malleable and we’re all so smart, we tend to think that our product can (and should) have a nice, big market to address.  For example:  In the case of I’m In, they could have easily tried to argue that the product is could be easily “reused” for organizing trips for small businesses.  Just a tweak hear and a tweak there and instead of limiting its market to gender-based social trips, it could expand the market considerably.  The same can be said for many software products.  There’s no technical reason to limit your software to a niche market.  Why not “go broad”?

  1. Figuring Out What The Customer Wants:  One of the biggest reasons not to “go broad” is that it becomes very difficult to figure out what to build.  For example, in the case of I’m In, small business group travel and social group travel have lots of overlap – but vary in some key ways. Businesses might care about things like rules and policies for travel – social travelers care more about fun, bonding and memories (like photos of the trip).  By trying to address the needs of two different customers (despite the fact that there are some needs they have in common), you end up compromising one or the other. 

  1. The True Cost Of Broad Products:  Lets stipulate for a moment that you and your team are smarter than average (just like all founding teams believe they are).  Despite your brilliance and the unquestioned ability of the team to create an exceptionally cool product that can address the needs of millions of users, the harsh truth is that broad, flexible, products that can address the needs of many types of users are almost always more expensive to build and maintain than products that only address the needs of a small group of people.  The larger the divergent needs of a group of users, the more complexity that has to be baked into the software to address the needs of these disparate users.  Even with our brilliant ability to deal in high-order abstractions, the very fact that we have to have lots of high-order abstractions makes the product harder to build and get right.  If you ever run into someone that tells you that they can build a really flexible product that can do lots of things (add an option here, set a configuration there…) at the same cost or lower than one that doesn’t have that much flexibility, run.  Certainly don’t send them my way and make me expend the effort to resist the temptation to smack them upside the head.

  1. It’s Not Always About The Product:  Lots of software people fall into the trap of believing that the primary cost factor is product development.  This is not always true.  The primary cost is often not building the right product, but getting it into the hands of the right customers.  This is where focus really starts to play a big role.  By focusing on the needs of a small subset of the potential market, lots of things become much, much easier.  A direct quote from Josh at I’m In:  “By focusing on a tight customer segment (gender-based travel), it has been much easier to write copy for the site, select photography, create tonality, and develop a list of targeted fulfillment partners.”  Though I don’t know what the heck tonality is, what I do know is that it is much easier to figure out what you’re going to say (your message) and get the word out there when you have a smaller, more focused audience that you’re trying to reach.  It’s really hard to believe how much of an impact this has until you actually experience it.  Literally overnight (the day you make your decision to tighten your focus), your discussions become clearer, your meetings more productive, your product roadmap more defined and you become immensely more attractive to members of the opposite sex.

  1. Restrictions Are Not Permanent:  Just because you start with a narrow niche and focused strategy does not mean you have to remain there for all eternity.  It’s simply a better way to start a company because it makes the early stuff so much easier.    As the company evolves and you learn more and more about the market, you can decide whether you want to go broad (i.e. tweak the product to meet the needs of another segment of customers) or go deep (build more products/features that serve the needs of the customers you already know).  The point is, don’t convince yourself that you have to widen your potential market now – because you don’t.  In most cases, you’re better off starting narrow and broadening later.

If you’re interested in this topic, I’d strongly recommend “Crossing The Chasm”.  It’s on my permanent list of recommended reading for entrepreneurs.  

I’ve had several startups in the past that I’ve been involved with that could have benefited from more focus.  What do you think?  Are there situations where an early-stage startup shouldn’t focus?  Would love to hear your thoughts.

Finally, my best wishes to my friends at I’m In.  Look forward to watching your progress.  If any of you end up setting up an entrepreneurial group trip to Las Vegas, I’m In!

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