@Gregory's Motivatr

Belief

I’ve come across a few stories recently about the importance of belief for entrepreneurs. What struck me most about all of the stories is that belief is both an essential companion and a fickle friend to anyone on an uncharted journey.

You can’t accomplish anything without belief, yet belief won’t always be there for you. Like a fair-weather friend, belief might abandon you precisely when you need it most. So what do you do?

Ben Huh, the founder of Cheezeburger, wrote a powerful post about his bout with depression and worse titled When Death Feels Like A Good Option. He recovered by, as he put it, leaving the room:

It wasn’t for several months that death no longer became an option, but leaving that room and dealing with reality was the best antidote to a make-belief world where life just wasn’t worth it. When I was fantasizing about death as the panacea, the harshness of reality actually helped — it presented me with problems that I could actually solve… 9 years after I left that room, I would call Brad Feld to invest $30 million in my odd-ball company… For those of you who struggle with this, I’d encourage you to keep walking out that door everyday.

Spencer Fry just posted Startups: Stress and Depression advocating having a cofounder as a way to share the burden:

I use to think that after having co-founded two successful startups I wouldn’t need a co-founder for my next one. I was wrong. You can be the most seasoned operator, but at the end of the day you need another shoulder to lean on… Without a co-founder to share the emotional side of running the startup, then, you’re left to bottle things up inside yourself. That’s not healthy and will negatively affect you as a person, which in turn will carry over to negatively affect your startup. You’ll take your stress out on your employees, the product, your loved ones, and your friends, all because you didn’t have a co-founder who could relate 100% with you about what’s going on. Don’t do this alone. 

Marten Mickos, the former CEO of MySQL, gave a Stanford talk emphasizing the need to have others who believe in you, because sometimes you’ll stop believing in yourself. For Mickos that believer was overtime his mother, mentor, investors and even subordinates:

What I’ve learned only in recent years was that I reflected over the fact that thirdly you must always have somebody who believes in you. And you must have somebody who believes in you more than you do, more than you can believe in yourself, because a human being wakes up every morning asking him or her herself, am I useful? Am I needed on this planet? Am I okay, am I doing okay? And we have this nagging doubt, self doubt that follows us throughout life. And when we are in a startup business or in the entrepreneurial world, we will face challenges, challenges that seem insurmountable, really bad situations. And then you have this double whammy that just when it is bad, it also feels bad. And you’re sitting there as the entrepreneur and realizing that you don’t really trust yourself. You are not sure you can make it through the day. You’re not sure you can solve the problem or the challenge you have. So, you have those moments of self doubt just when you cannot afford them. And that’s the moment where you need somebody else who believes in you and who reminds you that you are capable and who reminds you that you are a wonderful entrepreneur

I’d love to hear more people share their stories.

“Are you crazy? The fall will probably kill you.”

After Butch Cassidy and the Sundance Kid rob a railroad company one too many times, a team of experienced lawmen are commissioned to hunt them down. Butch and Sundance are cornered and outnumbered on a ledge (at least in the movie), with seemingly two bleak options: “fight or give [up]”.

Suddenly, Butch (Paul Newman) has a great idea: jump off the ledge hundreds of feet into the rapids of unknown depth. The following conversation ensues as he tries to convince his partner Sundance (Robert Redford) who seems set on the idea of shooting it out: 

Butch Cassidy: Alright. I’ll jump first. 
Sundance Kid: No. 
Butch Cassidy: Then you jump first. 
Sundance Kid: No, I said. 
Butch Cassidy: What’s the matter with you? 
Sundance Kid: I can’t swim. 
Butch Cassidy: Are you crazy? The fall will probably kill you. 

And they jump.

This should be familiar conversation to any entrepreneur.

At the very start of something new, there are an endless number of questions to consider anticipating the product is a success: Will you have the capacity and scalability to keep your service up with demand? Will your product be able to make a profit and be defensible from competitors? Are you violating any patents? How will you deal with people who want to use your system to spam? Will future innovations disrupt your hypothetical business model? What’s the exit strategy to provide liquidity to investors and shareholders? Can you swim?

But none of that matters if the market doesn’t want what you’re making. You’re unlikely to drown in success because the fall will probably kill you. Think about the swim, but focus on the jump.

My five minute rule for evaluating advice

A friend of mine who is starting her first company asked me for some advice over coffee on how to structure her angel round. She found an investor who said he wants to invest a significant sum, but they haven’t talked about the terms of the deal yet. The question most pressing on her mind was how to structure the deal: convertible debt or equity.

This friend has a great network. She told me she’d already asked for advice from several successful entrepreneurs and was confused because the advice was conflicting. Different advisors made impassioned arguments for each structure to her (which is no surprise since smart people disagree on this issue).

Resisting the urge to weigh in I just started asking more questions about: the company, her expectations in the fundraising process, the prior conversations with the prospective investor and how much money she thought it would take to get the business off the ground. 

It quickly became clear she didn’t really understand exactly how either device works or even how the legal process for closing a deal works. The very experienced people she talked to before me just spouted off advice (i.e. what worked for them) without asking questions or getting a basic understanding of her situation.

Instead of waxing philosophic on what an ideal angel deal is, I just explained what each structure really means and the logistics of closing a deal. It was a huge relief to her because she now understood the choice at hand, and I never told her what to do (aside from get a good startup lawyer!).

It made me think back on the precious good advice and the plentiful bad advice I’ve received since becoming an entrepreneur. 

The good advice usually came only after the advisor took the time, even if only a few minutes, to understand my situation.

The bad advice came quickly, sounded good at the time, but often turned out not to be relevant or appropriate. 

My only unconditional advice to you is not to take advice seriously if the advisor doesn’t spend at least five minutes understanding your situation first.

Philosopher entrepreneur

So that whole philosopher king thing Plato envisioned in The Republic never quite panned out, but I think us philosophers* might have found a calling in starting and running tech companies.

During breakfast this morning with fellow philosopher entrepreneur Bostjan Spetic of Zemanta, we discussed all the people with philosophy backgrounds running tech companies.

I thought I’d try to crowd source a full list by soliciting your thoughts in the comments or over Twitter.

List of philosopher entrepreneurs in alphabetical order (in progress):

• Fred Benenson, Kickstarter
• Patrick Byrne, Overstock
• Chris Dixon, Hunch
• Greg Galant, Sawhorse Media
• Damon Horowitz, Aardvark
• Andrew Kortina, Venmo
• William Lohse, Pivot Conference
• Ken Reisman, Tlists
• Amol Sarva, Peek
• Bostjan Spetic, Zemanta

I’ve also started a Twitter list of of philosopher entrepreneurs.

*It’s debatable if someone can still be a philosopher while fully engaged in a real profession. Even many of the philosophy professors I had probably wouldn’t qualify as philosophers.

Do it like Facebook

When I was building my first business in the late-90s, a friend who I was working with on a large project gave me some sage advice: Do it like Amazon.

He explained that for any kind of decision on functionality or user interface, the default answer should be Amazon’s answer. In our case we were asking: Should we have people make usernames or just register/login with their email addresses? Amazon just does email addresses, so do that.

If you didn’t do what Amazon does, there had better be a compelling reason why not, because Amazon had the benefit of the most experienced engineers and one of the largest bases of users to test with.

Now, the web has changed a lot and Facebook is the company that’s pioneering internet innovation. Facebook has over 200 engineers — arguably the most experienced team in social-driven web platforms — and over 300 million users. Facebook’s testing many new changes to its site daily with large sample sizes of users, so most parts of Facebook are the way they are for a good reason.

When you’re making all the little decisions necessary at the beginning of your next web project, you might want to consider the default position: Do it like Facebook.

Now of course that doesn’t mean you shouldn’t break with Facebook’s way occasionally or even all the time. But you need to know the rules (and who’s making them) before you can break them.