Becoming a CEO and the risk of 'me'.

In a recent comment on his blog, Fred Wilson mentioned ‘the founder and CEO needs to do three things well’:

  1. Raise capital
  2. Set the strategy and vision and articulate it
  3. Attract and retain talent.

What’s really interesting to me here is that there is no direct mention of attaining product-market fit, about sales or generating revenue, or about actually building a product or service and scaling it. Instead these are all things that are inferred by #2 and #3.

Yet if and when you go to actually pitch an investor, they are going to frame and focus on specifically these things.

Until recently, I honestly didn’t care about ever being the founder and CEO.

I just cared about building stuff people loved and actually used.

But, after finally getting started (after years of thinking about it) Coach Wizard has changed that for me. I believe in the mission, and the idea so much, that I actually do want to be the CEO.

The thought of being the guy to put the team together, to get this thing built the right way, and to scale it out to every coach and potential coach in the world gets me *really* excited!

So I’ve started thinking a lot about what it means to actually be a CEO and build a team and a company lately (hence my added interest in Fred’s comment).

And though, I’ve got lots of experience in building product and doing all the 'tech stuff’ as a founder and CTO, I wonder…do I have what it takes to be a really successful CEO?

If I evaluate myself based on Fred’s requirements, I’m pretty confident about #2 and #3 (because I think I’m already doing those on a small scale and will only get better over time)…but I have not yet started to really work on #1 so my real answer is, at best, incomplete.

So the big question remains, could I raise money?

Well, if I dive into it, I think raising money is largely about lowering risk for investors…and so the key question is really: What are the risks in backing me?

…and I think I can break that down into a four smaller, specific questions around a given investor’s assumptions and beliefs after meeting with me:

  1. Do you believe I can build a winning product?
  2. Do you believe I will stay focused on one mission for the long term?
  3. Do you believe I can set a winning strategy and vision, and that I will tirelessly and clearly articulate it?
  4. Do you believe I can build a killer team that will endlessly execute?

I think these generally outline the real 'risk’ if you’re interested in following or backing me as a CEO…so let’s quickly dig into some self-reflection and thoughts around each of these:

1. Do you believe I can build a winning product?

I believe my history in building great products that at least a small set of passionate users love speaks for itself. So I don’t think my 'technical’ ability brings much risk.

Have I done it at scale? Not on my own (the closest I’ve been on my own is in building Statsfeed LLC into a small six figure B2B service; and that was intentionally kept small and in the 'lifestyle’ category for various reasons).

Still, I’ve been around, and a part of, enough winning products and services to say with confidence that I feel comfortable recognizing it and steering the ship towards it.

2. Do you believe I will stay focused on one mission for the long term?

For casual fans of my personal brand, I expect to get this question or concern a lot because I’ve done a lot and been involved in a lot over the years. I recognize that this causes me to sometimes appear to have a fear of commitment; to lack focus.

What I can say here is just that, until now, my focus has been solely on building interesting things that people love and use; To be a part of an early, and important part of a team working towards a common mission (but not the leader).

With that frame, I think you can argue that I’ve actually been more focused and committed over the past 20 years than almost anyone else you would meet. The big difference right now is that my focus is on building and growing a company from the lead position, not just a product that people love and use.

3. Do you believe I can set a winning strategy and vision, and that I will tirelessly articulate it?

For this, I think you’ve simply got to buy into the 'why’ behind Coach Wizard. That is you’ve got to believe, like our team does, that great coaches have a positive life impact on those that they touch…and that developing more great coaches is a company and life mission worthy of pursuing.

If you believe in that, then I think 99% of the strategy and vision that I’ve been putting together will simply click with you…and my ability to articulate against that belief now and in the long term will probably not be in question at all (and will also only get better over time and through more experience).

4. Do you believe I can build a killer team that will endlessly execute?

I’m already making progress on this front, so there’s a little bit of progress to work with here already…and I’ve got at least a little bit of history as a CTO in helping to build tech. teams that, I think, were great.

But I’ll admit this is one area that just may require a bit of a leap-of-faith until hindsight can reveal the true answer. In the meantime, I’m focusing insanely on the 'why’ and using it to help identify and draw in the most talented team I can (and it’s been a lot of fun so far).

So there you have it…some quick, and random, ramblings around my quest to finally become a legit CEO and the initial risk questions I think anyone interested in following or backing me has to consider.

What do you think?  Agree, disagree, or have questions around any of this, I would love the opportunity to talk to you about it in more depth…so please do reach out!

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This is the personal blog of Kevin Marshall (a.k.a Falicon) where he often digs into side projects he's working on for digdownlabs.com and other random thoughts he's got on his mind.

Kevin has a day job as CTO of Veritonic and is spending nights & weekends hacking on Share Game Tape. You can also check out some of his open source code on GitHub or connect with him on Twitter @falicon or via email at kevin at falicon.com.

If you have comments, thoughts, or want to respond to something you see here I would encourage you to respond via a post on your own blog (and then let me know about the link via one of the routes mentioned above).