Startup Lessons


One of the vivid memories I have from being a startup CEO is the feeling that most people in your company have a look in their eyes that like they can do your job as well as you. How hard could it be? You just assign out tasks to all of us.

In the early days the CEO is the jack-of-all-trades, doer-of-all, famously the “chief janitor” or coffee maker. But if you level up, raise capital and grow customers, revenue and staff – life changes. Eventually you need a VP of Product to handle your product roadmap, a CTO for engineering leadership and VPs of sales, marketing & biz dev. Most companies that are scaling have CFOs, heads of HR or talent. The “span of control” for a growing tech startup is probably 6-9 people. The “doers” in your organization.

This is when your job function truly starts to match the definition of “leader” because that’s exactly what your role is. You set direction. You hire great people. You help them prioritize their objectives and review the results. You course correct. You motivate, cajole, reassign tasks, hire, fire and push the organization forward. CEOs who try to do everything themselves rather than lead are usually pretty ineffective – they can’t scale.

Leadership is actually quite difficult. You have this tension between on the one side being a micro-manager (by which great people won’t want to work with you) or being hands off (and having quality lapses or team alignment issues). Neither end of the spectrum is particularly effective. The best leaders are great at hiring in large part because they are inspirational.

If you hire truly talented people you end up definitionally with a lot of competitive peers who will inevitably jockey for resources and control. Extremely talented people are ultra competitive.

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I was at a dinner recently in Chicago and the table discussion was about building great companies outside of Silicon Valley. Of course this can be done and of course I am a big proponent of the rise of startup centers across the country as the Internet has moved from the “infrastructure phase” to the “application phase” dominated by the three C’s: content, communications and commerce. But the dinner discussion included too much denial for my liking.

I think startup communities being simple cheerleaders doesn’t help anyone. Those of us outside Silicon Valley need to make an effort to effect change not just wish for it.

At the dinner some of those arguing that Chicago has everything it needs now that it has built: GroupOn, Braintree, GrubHub and others and that it has “come along way” and “will never get the full respect it deserves just because it’s not Silicon Valley.” But I think this misses the point. I’m a very big fan of Chicago. I started my career at Andersen Consulting (now Accenture) so I went to Chicago many times a year for nearly 9 years.

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We all know that funding markets have changed for startups. The trends are well understood: more angels, more seed funds, more crowdsourcing and so forth. We all can intuit the benefits to founders of these trends so there’s little reason to elaborate. What is less understood are the consequences of these changes.

I have blogged about some of the downside consequences of the changes and the private information I have says the consequences are much worse than is reported in the press since few people publicly talk about

1. How founders get screwed on convertible notes
2. How party rounds can burn you if it takes time to find your groove

There’s another issue I can add to your list of things to be aware of – information rights. Generally speaking in venture capital financings the legal documents will specify that only “major investors” (a threshold set in the agreement – which can be $500,000 investor or more). There is a reason for this.

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Last week a company we enthusiastically backed, uBeam, led by a very special entrepreneur, 25-year-old Meredith Perry, announced a $10 million round of financing.  The press around the raise & company was fantastic and the promise of their technology – wireless charging that works as easily as WiFi – would positively affect many of our lives. What person hasn’t crouched at an airport to get 18% extra on one’s battery before boarding an airplane?

But then one person – who happens to be a physicist – wrote a back-of-the-envelop calculation of uBeam and said it’s not physically possible. His math was correct and I can hardly blame him for taking a guess at what uBeam does but every assumption that he used was wildly inaccurate. uBeam’s tech does work and I have safely seen it demo’d in the real life many times. Most of those that have been privileged enough to get a look at what they are actually doing have moved from skeptics to believers.

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This weekend I was reading the NY Times online and I came across this excellent piece about ADHD written by Richard Friedman, a professor of clinical psychiatry. In the article the author talks about the condition of the brain – which affects up to 11% of American children in which people with ADHD (or ADD, which doesn’t have hyperactivity) – in which people with ADD have a low tolerance for routine tasks and thus they seek out “novelty”.

The author believes this may have had an evolutionary advantage. He specifically notes the people with ADD

“are drawn to new and exciting experiences and get famously impatient and restless with the regimented structure that characterizes our modern world.”

The author talks about one of his patients who was bored and unsatisfied in his job and found his tasks too routine.

“he quit his job and threw himself into a start-up company, which has him on the road in constantly changing environments.

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I’m pretty on record as saying I don’t think many private-to-private tech mergers make sense. They are often done from a position of weakness. Something in both companies isn’t working, which is why they come together.

I often don’t believe in the therm M&A because in my experience mostly A works.

But of course there are always exceptions. And even when I remain skeptical sometimes opportunities present themselves that prove one should never be absolutist.

As many people know I funded a company called Moonfrye almost 2 years ago led by two amazing women – Kara Nortman & Soleil Moon Frye. Our goal from the outset was to build a great eCommerce experience that could compete with Michels on one side (for DIY / crafting) and Party City on the other (throwing events / parties / celebrations).

The thesis was simple. Mom’s struggle to plan events and activities for their kids. Most products out there suck so mom gets stuck with angst of wanting to have decorations, activities and chatzkies for other kids to take home. What should be an enjoyable experience turns into a time-suck obligation and angst-ridden day of self questioning.

Our product name is P.S.

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