Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything – all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. - Steve Jobs

When I was in my 20’s I worked at Convergent Technologies, a company that was proud to be known as the “Marine Corps of Silicon Valley.” It was a brawling “take no prisoners,” work hard, party hard, type of company. The founders coming out of the DEC (Digital Equipment Corporation) and Intel culture of the 1960’s and ‘70’s. As an early employee I worked all hours of the day, never hesitated to jump on a “red-eye” plane to see a customer at the drop of a hat, and did what was necessary to make the company a winner. I learned a lot at Convergent, going from product marketing manager in a small startup to VP of Marketing of the Unix Division as it became a public company. Two of my role models for my career were in this company. (And one would become my mentor and partner in later companies.) But this story is not about Convergent. It’s about entrepreneurship and family.

We Sleep Peaceably In Our Beds At Night Only Because Rough Men Stand Ready To Do Violence On Our Behalf.

Everyone has events that shape the rest of their lives. This was one of mine.

In 2023 China flying a “spy balloon” over the U.S. created an international incident. It turns out the U.S. did the same to the Soviet Union in the 1950’s.

Reducing Risk – Simulation versus Customer Development

If you remember the first part of this discussion, startups face two types of risk; invention risk and/or customer/market risk. In either type of startup you want to put in place processes in place to reduce risk.

I’ve screwed up a lot of startups on faith. One of the key tenets of entrepreneurship is that you start your company with insufficient resources and knowledge.

I wrote this “Going to Trade Shows Like it Matters” memo as a board member after I saw our company at a trade show. Part 1 of this post offered some suggestions on going to trade shows to generate awareness. This post offers suggestions if you are going to a trade show to generate leads.

I was having lunch with a friend who is a retired venture capitalist and we drifted into a discussion of the startups she funded. We agreed that all her founding CEOs seemed to have the same set of personality traits – tenacious, passionate, relentless, resilient, agile, and comfortable operating in chaos. I said, “well for me you’d have to add coming from a dysfunctional family.” Her response was surprising, “Steve, almost all my CEO’s came from very tough childhoods. It was one of the characteristics I specifically looked for. It’s why all of you operated so well in the unpredictable environment that all startups face.”

One day I was having lunch with a VC sharing what I learned from my students. “Steve,” he said, “you’re missing the most interesting part of vertical markets. Our firm has a portfolio of companies across a broad range of markets and the way we look at it is pretty simple – the deals fall into two types: those with customer/market risk and those with invention risk.”

In the past entrepreneurship was viewed (and taught) as a single process, with a single approach to creating a business plan and securing funding for a startup. The best entrepreneurship textbooks and blogs assume that advice to startups is generalizable. But as I learned from my students this “one-size-fits-all” approach does not work for all startups. Different market opportunities present radically different startup risks and costs.