‘Dear Founder’ Is the Business World’s ‘Dear Abby’ That Entrepreneurs Should Read

Whenever I’m motivated to take on a massive undertaking, be it a new adventure, traveling to another country, or anything work-related, I try not to take a half-ass approach to it, and this means educating myself on all possible avenues, obstacles, and angles. Whether talking to experts or extensively researching items online, I continue to dig through all the data I can find before determining that I’ve answered all my questions. This is a logical step that I’d imagine most, if not all, entrepreneurs will do as they start their businesses, but it seems that most of the information is largely distributed across sites and individuals.

A signature feature in newspapers is the advice column, with one of the most well-known titled “Dear Abby“. Each week, readers would have their pressing questions answered about life, be it about romance, family matters, work, society, relationships, finances, and more. In the business world, nothing like that really exists, especially coming from an expert. Don’t get me wrong: there are a lot of credible people in the industry, but when it comes to understanding entrepreneurs and CEOs, some helpful filtering of answers is needed.

Advice column for entrepreneurs

That’s where a new book titled “Dear Founder” plays a critical role in helping entrepreneurs build out their business. It doesn’t matter whether you’re in technology or not, this 352-page book provides sage and practical advice readers need to become leaders. And it’s not filled with pithy philosophical quips, but actionable advice and covers subjects you wouldn’t get from an entry-level book on entrepreneurship.

“Dear Founder: Letters of advice for anyone who leads, manages, or wants to start a business” is co-written by Maynard Webb, an individual with a storied history in Silicon Valley. He was the former president and chief operating officer at eBay before taking over the helm of LiveOps as CEO before becoming its chairman. Besides authoring books, Webb is the co-founder of workplace mentoring startup Everwise and the founder of Webb Investment Network, not to mention that he sits on the boards of Salesforce, Visa, and Yahoo.

Joining Webb is Carlye Adler who is an accomplished journalist and author, having contributed to books by Salesforce CEO Marc Benioff, Andreessen Horowitz partner Ben Horowitz, Zendesk CEO Mikkel Svane, and also Webb’s previous book “Rebooting Work.”

While organized in a way that guides you through the process of building out your business, following that linear path is not scripture. Each chapter is framed as a letter Webb or a guest author pens in response to an inquiry he’s received. As such, you should feel free to jump directly to the chapter of your choice and not risk missing out on the knowledge that might be buried in previous chapters, like other books. The structure reminds me “Ask GaryVee” in which Gary Vaynerchuk similarly responds to frequently asked questions about entrepreneurship.

40-years of entrepreneurial advice

Unlike Vaynerchuk’s book, “Dear Founder” addresses the CEO and founder directly — the person who has made a conscious decision to launch a business and wants to grow to become the next Mark Zuckerberg or Marissa Mayer. While some entrepreneurship books often scratch the surface, Webb provides anecdotes from his time in the trenches, offering advice on things founders will likely have to deal with either in the beginning or over time. Let’s take a look at some of the topics covered:

  • How to resolve co-founder disputes; when you need to recruit; hiring a rock star; setting your culture; dealing with diversity and inclusion; and onboarding executives.
  • What to do when no one will invest versus when everyone wants to; how to figure out your valuation; dealing with budgets and compensation; and what about philanthropy?
  • How to delegate as managers, dispensing responsibility, and establishing goals.
  • What should you do when your first hire leaves? How do you fire someone? What if no one is excited to work there? 
  • Overcoming personal challenges of leadership.
  • How should you handle new competitors, the press, and what if your idea isn’t working?
  • Improving the company operationally to deal with scale; running an effective board meeting; and avoiding nasty surprises.
  • Quarterly goals.
  • How do you build a company that lasts for the next 100 years.

Although primarily geared towards those in business, it doesn’t matter whether you’re a cook, janitor, architect, designer, developer, marketer, or a stay-at-home person. If you’re interested in becoming a leader or perhaps run your own business at some point, then “Dear Founder” is a good starting point to be aware of what you’re up against. Think of these letters as something that a father would pass down to their child, imparting wisdom so that they may see the same success as their parents have before them.

Webb’s perspective on entrepreneurship was refreshing as his vantage included both working for established Fortune 500 companies and also founding his own startup. Previous books I’ve reviewed offer a one-sided affair, that from the perspective of the founder. That’s not to say it’s bad, but the examples that Webb provides can further inform readers who have a desire to launch their own business. “Dear Founder” is a blend of Webb’s 40-year work history, time as a board member, the trials he endured while at Yahoo, and as an investor managing a portfolio of companies. It’s certain that he has amassed quite a bit of intelligence to share on the subject matter. 

“Dear Founder” is now available for sale on Amazon and at your nearby bookstore.