Founders, Advisors, and Fools


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In business school, I had an entrepreneurship class where the professor classified all people who’ve started companies as fools, and entrepreneurs as successful fools. Honestly, I’m not sure there’s a difference between the two.  With that in mind, I’ve been a fool and advised fools/entrepreneurs for nearly 15 years.

I’ve always enjoyed the process of helping people take their best shot at the foolish life, having lived both the highs (assembling Ikea furniture for new employees, finding product market fit, raising funds) and the lows (bankruptcy, disassembling said Ikea furniture, saying goodbye to my team).  Here’s a short list of things I’ve learned in that process.

1. Call a spade a spade but don’t call it a f****** shovel

As an advisor, I’ve tended to be brutally honest with folks I’ve worked with, whether it’s a complete redo on the style and substance of a presentation, or explaining that a product isn’t ready for primetime. Being consistently honest builds trust quickly with entrepreneurs, and given the short timeframe for their success with limited capital, that time is critical. The faster they trust your advice and execute against it the better.

I also understand that the last thing an entrepreneur facing long odds needs is more negative feedback, so while brute honesty is important, I try and find ways to not only criticize but always suggest positive changes or alternatives to the task at hand. It’s easy to say something is wrong, but an advisor without a positive suggestion on how to improve it is just a critic. 

2. I am Morpheus.

“Neo, sooner or later you’re going to realize just as I did that there’s a difference between knowing the path and walking the path.”

One of the biggest obstacles to personal success is self-doubt.  Doesn’t matter whether it’s an entrepreneur or a line employee, career success is completely dependent on a person’s desire to set a target far above what seems plausible and to chase after it without reserve.  I classify most entrepreneurs as Neo from the Matrix, individuals who actually already are rockstars in just the mere act of starting something impossible, but just don’t believe it enough to assume it and succeed.  The job of a great advisor is to help a person find that uber version of themselves, a Morpheus to their Neo.

For me, this comes in a bunch of different ways, but the most critical is first realizing that my experiences and failures are a great tool. The constant s***-storms, politics, second-guessing and fail whales of a startup are a common, shared experience. Helping an entrepreneur realize that they’re not alone in that process helps remove some of their self-doubt. Self-deprecation and lessons learned from my own iterative failure are a massive help to an entrepreneur looking for advice and support when they need it most, when things aren’t going well.

In addition, once an entrepreneur has achieved a base level of success (initial traction, first funds raised), I consciously stay away and let them do their thing. Being Morpheus means letting go, until the next time you’re needed for good counsel. The most successful startups I’ve advised I helped heavily at the outset, and didn’t hear from them for 3-4 years, which was when the bankers called for a home address to send paperwork.

3.  “Stay hungry. Stay foolish”

I just read the Steve Jobs book by Walter Isaacson, and man was Steve off-putting. In many ways, his negative engagement with partners, employees and friends would drive most companies to abject failure. But one thing that drove his massive success was his unabashed desire to explore new things (drugs, philosophy, diet, technology).

I’ve advised a couple dozen startups to this point and worked at a half dozen. One thing I’ve gotten used to is constant change. Most folks hate it. Frankly, for a long time I wasn’t a huge fan of it either. If things were going well, I wanted things to continue going well and not have to constantly effort success. Yes that’s called laziness and it’s a common problem. It’s hard to tell someone to just work harder or smarter to deal with it. In fact that’s stupid advice. I prefer to repeat the Steve Job mantra instead.

“Learn to never be satisfied with the status quo, to constantly expand your understanding of users, audience, products or markets.”

Working with entrepreneurs to strive for that ideal helps them adapt to constant change. As an advisor, you should help an entrepreneur see that it’s something not only to expect and fear but to work towards and achieve for themselves. Driving their own constant change into an organization or market versus being the recipient of it can dramatically improve an entrepreneur’s outlook on a business, reduce their doubt and ultimately deliver success.

Being foolish and driving change may be the only way to truly succeed as an entrepreneur. Frankly, it’s impossible to be a great advisor if you haven’t been the fool yourself.

Roy Choy is the COO of BitTorrent. His experiences include:

  • Advising more than 20 companies.
  • Taking revenue from $300K to more than $30M over three years at RockYou.
  • Raising $3M based on concept for a natural language processing startup.

Schedule a call with Ro to talk about growth, operations, and advising.

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