Welcome
What running a startup is really like, minus the myths
As a general rule, I don’t read books or articles about business, which I think is unusual for someone in my line of work. But I have good reasons, or at least reasons that I’ve convinced myself are good.
In my experience, nearly all business-related books and articles are of two main types. Most frequently, they’re “how tos” that provide practical advice (e.g., how to do online marketing, or how to raise money from venture capitalists, or how to innovate, etc.) These can be helpful (sort of), but they usually have a one-size-fits-all quality and are seldom interesting.
Alternatively, they’re biographies or autobiographies about business leaders that focus on “the hero’s journey.” I like these even less because they tend to overstate the “hero’s” achievements and understate the role that luck played in their success. Said differently, they aren’t heroes at all, and so their “heroic” journey doesn’t resonate or ring true.
Consequently, when I started thinking about writing a book, I knew what I didn’t want it to be.
I hoped to share lessons based on my personal experiences, but I had no interest in writing a traditional “heroic” memoir. Nor did I have any interest in writing a traditional “how-to.” The one thing I (emphatically) knew was that if I was going to write a book, it needed to be original and unconventional. I feel the same way about this Substack.
So what am I trying to do? The short answer: tell autographically-based stories which highlight business (and life) lessons that I hope people will find interesting and unexpected. My overarching objective is to give readers a sense of what it really feels like — practically, ethically, and emotionally — to run a crazy, early-stage, venture-funded technology company.
And that requires spending as much time looking at failure as success.
Running startups is not for the faint of heart. It’s a psychological rollercoaster that goes down more than up — a metaphorical Omaha Beach on D-Day — a relentless exercise in self-delusion and masochism.
But, at times, it’s also a lot of fun.
My hope with this Substack is to bring all of that to life— the good, the bad, and the ugly of entrepreneurial endeavor.