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M.R. Asks 3 Questions: Maynard Webb, Author ‘Dear Founder'

By January 23, 2019Article

Maynard Webb has a long list of credentials and accomplishments including, Founder of the Webb Investment Network, philanthropist, and Visa & Salesforce board member. In 2013, Maynard became a New York Times Bestselling author with his first book, Rebooting Work: Transform How You Work in the Age of Entrepreneurship and in September 2018, published his second book, Dear Founder. 

When asked, Maynard explained that Dear Founder, Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business is a collection of more than 80 letters written to founders to provide guidance during various inflection points they’ll face in the course of running a company. The letters aim to answer their questions and provide actionable advice when it comes to handling a business’s most gnarly problems. 

M.R. Rangaswami: Why did you write Dear Founder? What do you think this adds to what has already been written?

Maynard Webb: About two years ago, as a passion project, I started writing personal letters to the founders of companies in our investment portfolio, offering advice informed by my distinct business philosophy for the defining moments that all entrepreneurs face: “When your board is driving you crazy;” “When you have to fire your first employee;” “When you missed your quarter,” “When your company has outgrown you.”

I found that founders needed this kind of advice and they didn’t know where to turn. The letters were a way for me to have a 1:1 with them whenever they needed.

I was inspired by a great but fictional Medium story my son sent me about a dying father who leaves his son a box of letters to help him navigate various the rites of passage he will face throughout his lifetime. I really enjoyed writing the letters and my team at the Webb Investment Network put the letters into a book for to entrepreneurs seeking my guidance. They worked with a custom bookbinder in San Francisco and printed 300 copies as a gift for the founders in the WIN portfolio.

The feedback was incredible. People wanted to share the letters with their friends and asked how they could get more to give to their team or as holiday gifts. We ran out of books, so we created a downloadable private copy. But I found there were always new challenges to cover, so I continued writing letters.

We compiled more than 80 letters into a book, Dear Founder, which came out in September. It was a way to scale this project so we can reach more founders, including ones I never met!

The book has an original format—it’s a collection of letters on very specific topics that founders face. The book is divided into 4 parts (getting started, getting to relevance, getting to scale, and leaving a legacy) and subdivided into chapters within the parts so everything is organized and easy to find. Readers can read through (and the book follows the arc of a company lifecycle) or they can use the book more as a reference to find guidance when they arrive at certain inflection points: when they need to build a great board, when they miss their quarter, when they have to fire their first employee, when they get bad press, etc.

What I’ve found is that even though the book is done I continue to write letters. There are always new topics founders need guidance on! This month Fast Company is starting a weekly column where readers can ask me questions. Email me your thorniest questions at

There’s not really another book written in the format with a business advisor or coach providing letters to entrepreneurs who need guidance on the very specific building blocks of starting and scaling a company. Some of the most appropriate comps: The Hard Thing About Hard Things by Ben Horowitz, Zero to One by Peter Thiel and Blake Masters and the classic, What They Don’t Teach You at Harvard Business School by Mark MacCormack, also has a mix of unconventional and practical advice from someone who’s been in the trenches.

M.R.: If I only had time to read one letter in this book, what would you suggest? 

Maynard: I like to learn what others are going through so I can pick the right letter for each person, but I feel like, “When you need inspiration” offers perspective and advice that would be helpful to most people. In it, I share how inspiration often starts with frustration and include what I learned from Marc Benioff at Salesforce as well as my own experiences at eBay and when I started the Webb Investment Network (WIN).

I’m grateful to Mitch Kapor for what he taught me, and I hope sharing his wisdom helps others. I love hearing from readers who tell me what letters have impacted them. Recently someone told me he really needed to read “When you are dealt body blows.” “When you are afraid you might be a tweener” has helped founders navigate at a tricky crossroads.

M.R.: What was the hardest chapter to write?

Maynard: No question, the letters on diversity (“When you need to hire diverse candidates” and “When you need to create a workplace of inclusion”) were the most challenging. First, I know that embracing diversity is not only the right thing to do, but it’s the right thing to make your company stronger. However, I’m not an expert on this subject, and I am also a white male and someone who has not personally faced these very real challenges.

Second, it seemed like there were issues and allegations against companies in Silicon Valley (where I work and live) popping up every day. I love Silicon Valley for its commitment to innovation, but I also had to recognize that it’s an environment that could be vastly improved for a large part of the working population.

I knew there was room and reason for change but I needed help figuring out what steps needed to be taken. Therefore, I consulted several experts in this area. They were generous with their time and wise with their counsel. With their help I was able to write two letters, which are some of the most important in the book—and share actionable advice on things like how to remove subconscious bias from the hiring process, employing a diverse set of interviewers, and the necessity to reconsider how you define diversity.


M.R. Rangaswami is co-founder of Sand Hill Group and publisher of

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