When you publish a book of letters about running companies
Today marks the launch of Dear Founder, a project that started as a half-baked idea in early 2016, and quickly spiraled into one of the most rewarding and personal projects I’ve gotten to collaborate on in my eight years in venture.
First, some background. I work at the Webb Investment Network, a small venture fund with which I, not coincidentally, share a name. After college, I got an opportunity to help start WIN alongside my dad, Maynard Webb, and Michael Neril, a colleague of his from LiveOps. I didn’t know much about venture beyond what I’d picked up through some summer internships at startups, but I would get to meet people working on interesting ideas, I’d help set up a new company, and most importantly I’d have the chance to work with someone I admired and liked. I didn’t think I’d stay long, but we were coming off of the Great Recession, and it seemed like a fun (and prudent) way to spend a year or two.
In high school, my dad would indulge me in discussing business ideas and my feature requests for eBay, and I knew from our family’s moves and his increasing stature that something about how he operated made him stand out. I knew by heart the story of a kid with a single parent (a teacher!), who paid his way through college, who took a job as a security guard at IBM, and who angled for every difficult job he could on his path to where he was now.
His story, though, wasn’t mine, and to me his continued corporate rise was just an unquestioned natural law of my increasingly privileged universe. Throughout many of my formative years he was busy, and so was I. He was helping run an online e-commerce company, and I was taking every AP class and joining every extracurricular I could. I prided myself on charting my own course.
So it wasn’t until I had the chance to work with my dad that I started unpacking what had carried this person so far. We set up the fund unusually; instead of LPs, we have people called Affiliates, who are all past colleagues of his. They’re selected not because they have interesting roles (though they do), but because they were consistent contributors and more importantly, they treated people well.
As I grew into my role, I saw that Maynard was generous with his time, and was happy to share career advice with countless people who had crossed paths with him. In meetings with founders, he would always ask about the whole of them, how their families were, how they were feeling. We didn’t always hit the necessary transactional aspects of an investor pitch or update meeting, but Maynard would surface issues founders didn’t know they were ready to be discussing, let alone addressing.
He would sometimes give advice in the form of truisms, and if they weren’t so authentic to his experiences they could have come off as trite. Some classic Maynardisms (there are plenty more in the book):
“Don’t confuse action for traction.”
“Problems don’t get better with age.”
“You have to get voted onto the team every day.”
These may sound simple, but I promise living to them isn’t. Behind them are simple truths: do the right thing. Do the hard thing. Treat people well throughout.
As I was working with him, I lived through the dizzying, post-iPhone rise of this current venture ecosystem, where there are more funds than great ideas, more Medium sages than real experts (hi!), and more induced urgency than even a well-keeled brain can reasonably process. Against this noisy backdrop Maynard’s advice felt timeless and crucial, earned from years both operating and serving on boards.
Hence, the central idea of Dear Founder: advice for specific, predictable events managers and founders may encounter, presented in a friendly, nonjudgmental way. To an individual, crises and major events will appear as singular, stressful affairs. From a distance, though, patterns emerge, and issues of running companies truly boil down to human dilemmas that are as relevant today as they’d have been decades ago. Put this knowledge into a book of letters meant to be opened at specific times, and this quiet advice will be ready to consume when needed.
When I offhandedly suggested the concept at a restaurant in downtown Palo Alto in early 2016, Maynard and my normally more reserved colleague Jonathan Pines latched onto it. From there, the project took on a life of its own; Maynard began cranking out letters, and in typical Maynard fashion he challenged us to 1) write more than him (we didn’t), and 2) to have a completed, self-published book ready for our founders by Fall 2016 (we did).
This book is by no means perfect or complete, but it’s heartfelt. Maynard took ideas for letters from our founders, Affiliates, and our team, and would craft his own topics as he sorted through his thoughts about how best to help someone he knew facing a challenge. Carlye Adler, his amazing co-author, pulled more out of him than he expected to share, and each of us on the team (Jeremy, Jonathan, and Dena) read through and edited the whole of the book multiple times through.
Dear Founder is also an evolution; our self-published, shorter first edition, Letters to a Founder, went to 300 founders and friends almost two years ago. It was their encouragement that led us to publishing Dear Founder more broadly today, with the help of St. Martin’s Press.
I’m proud of this product and am deeply grateful for the opportunities and circumstances I’ve had that have let me be a part of it. Beyond wisdom, I hope it provides comfort to anyone who has to work with others to do the improbable.
