Dear Founder

Maynard Webb’s Dear Founder is a different kind of startup story, told through the letters an active investor might share with a founder struggling, failing, persisting, and triumphing in their quest to build a sustainable business. It isn’t a retrospective history of the latest tech IPO, nor fawning Silicon Valley hero-worship—just candid, objective insight into the moments that can make or break a fledgling venture.

The letters are each written for moments ranging from the good (“When you have a big payday”) to the bad (“When your board is driving you crazy”) and the likely terminal (“When your idea just isn’t working”). There are numbers to hit, of course, but also relationships to manage, crises to navigate, and emotions to mediate as things work out—or don’t.

Each letter contains thoughtful, clear, and appropriately generic suggestions, framing complex situations without prescribing solutions. Webb’s considerable experience as both a founder and investor is certainly on display, but with plenty of room left for the reader to tailor it to her own situation.

If the letters have a recurring theme, it’s the collective investment in a successful business. Webb clearly cares for his reader and their team, but the flinty executive is never far away. When tensions arise between star employees and the needs of the team, or between founders’ ideals and investors’ returns, it’s the business that ultimately matters. There are no villains: just finite resources, tough choices, and consequences that may or may not be as consequential as they first seem.

Nor are there heroes. Silicon Valley’s biggest names and fastest rocketships are notably absent. We meet a few of Webb’s colleagues, but the book’s real protagonist is the reader—not one of Webb’s golfing buddies, the founder of his brightest portfolio company, or even the author himself. It’s a humble departure from business-as-usual in startup nonfiction, but it certainly isn’t a change for the worse.

Dear Founder won’t be a book for everyone. Most of us won’t start our own companies or take venture money. But for those that do—or for family, friends, and employees trying to empathize with their journey—this is a worthwhile collection of sincere, uniquely-informed advice.

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