Maynard Webb’s final Dear Founder column for Fast Company

The Fast Company Dear Founder column grew out of my book Dear Founder, published in 2018. While the book went to print, capping the letters of advice I wrote to founders to a limited number, the questions kept coming. How do I find a cofounder? What are the going rates for startup pay? Is 40 years old too old to succeed? I’m grateful that Fast Company gave me a platform to continue these conversations and an opportunity to share my advice—hard earned over 40 years in tech—more broadly.

Over time, the people who reached out to me evolved. We heard from founders as well as CEOs, executives, department heads, employees, angel investors, venture capitalists, board of director hopefuls, nonprofit leaders, and people leaving their careers and launching into the unknown. I’ve loved receiving and answering these questions over the last three years. It’s been an absolute privilege to be with people as they are navigating a crisis or contemplating a crossroads. I’ve been able to offer insight on complicated matters like accelerating the vesting schedule of a terminally ill employee or buying back an idea after selling a company. It has been an honor to help with of the most difficult situations: Dealing with brutal feedback, what to do when the board wants to replace you as CEO, how to know when to give up. Many of the questions reflected the zeitgeist and allowed us to engage in important discussions: How to fix a botched Black Lives Matter message, how to increase diversity during a hiring freeze, how to manage a changing culture. The past two years were marked by a new era, and I was asked questions such as how to fundraise in a pandemic, how to foresee future black swan events, and how to deal with the great resignation.

Most of all, the column has given me a window into seeing people trying to do the right thing. It has been humbling to interact with people looking for guidance on how to grow and improve. When I reflect on the last three years, I see the power of potential. I urge you to continue to push on it—because when you do, it expands in new directions and way beyond what you once thought possible.

I have deep gratitude to everyone who reached out to Dear Founder, and I think of your stories as I write my final Fast Company Dear Founder post. A sincere and heartfelt thank you to Stephanie Mehta for conceiving the column with me and producing it with enthusiasm week after week; it has been a great joy. I’ll miss this weekly dialogue, but I’m looking forward to contributing to Fast Company and exploring big themes in a different format. All the Dear Founder questions will be archived, so they can be easily accessed. I’ve been doing this long enough to know that building a business, creating something out of nothing, and managing people doesn’t get any easier. This is hard, sometimes gnarly, but mostly rewarding, work. I will continue to answer questions on LinkedIn, so please go to my page and keep the questions coming.

Wishing you all the best,


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