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Maynard Webb.

From his early days as a security guard to launching startups and leading world-class tech giants, Maynard Webb has learned a lot about what it takes to grow and sustain a business.

Now he’s ready to share those lessons with the world. Webb, the former eBay COO and Yahoo chairman who sits on the boards of companies including Visa and Salesforce, this week released his second book, Dear Founder, to the masses.

Maynard was in Seattle on Thursday promoting the book and sharing leadership advice at an event with former Starbucks CEO Howard Schultz, who wrote the foreword for Dear Founder.

GeekWire sat down with Maynard to learn more about the book and his career, which included a seven-year stint at eBay where he helped grow the e-commerce platform into an internet behemoth worth billions.

Dear Founder is a collection of more than 70 “letters” from Webb that are designed to help founders at any age or stage, from picking a co-founder and setting the culture, all the way to scaling a business and managing a large workforce.

Much of the book focuses on overcoming challenges related to leadership and management.

“It all comes down to people at the end of the day,” Maynard told GeekWire. “Who do you have on your team? Are you able to recruit great talent and inspire them? Do they want to hang with you and do things most other people feel would be unable to be done?”

Maynard said he’d tell his younger-self to slow down, learn to be “even more humble faster,” and to not “run over your teams.”

“I was probably more command and control with my teams than I am now,” he said.

The idea for Dear Founder originally started within the Webb Investment Network, an investment group launched by Webb in 2010. A shorter version of the book was distributed to the group’s portfolio companies and affiliate network as a gift.

The following is an excerpt from Dear Founder, under the section “When you want to start a company.”

From DEAR FOUNDER by Maynard Webb. Copyright © 2018 by the author and reprinted with permission of St. Martin’s Press, LLC.

Dear Founder,


Why do you want to do this? I hope it’s not because it’s the cool thing to do . . . it’s easy to become an entrepreneur, but it’s way harder to become a successful entrepreneur!

These days it seems everyone wants to be an entrepreneur. People become enamored with the idea of pursuing their own passion and being in control of their own destinies. Yet that’s a romanticized notion of what really happens.

I hate to be the bearer of bad news, but most entrepreneurs fail. It’s not just the statistics that show us this; it’s also common sense. It’s very hard to turn an idea into reality, and even harder to turn that new reality into something of great significance.

Sure, we know the breakout stories — those A+ideas that took off from the beginning, like Facebook, Google, or eBay. Yet the fact is that these companies are very rare. Oftentimes, the world is not ready for a new idea and the majority of companies don’t get traction. Intrepid entrepreneurs go back to the drawing board and pivot, but that maneuver is not representative of the reality of startups. Most companies fall in a middle space—there’s some traction, but the flywheel isn’t spinning, and you’re not sure if the idea will scale. This uncomfortable middle place is what I call a “tweener” and it’s a dangerous place to be.

So, you’re still keen on starting something? A number of questions for you:

  • What are your motives? Are you in this for money or impact? You must know what you’re really chasing; otherwise, you’ll never find it.
  • Do you have an idea that you are deeply passionate about? This question is perhaps the most important one. If you pursue your idea, you will likely be waking up every morning of the next two to ten years touting its value not just to your employees, but also to your customers, to your friends, to your family, and to your significant others. Even if you are the first to realize the concept, large entities and new startups will be quick on your heels. There are thousands of opportunities for new businesses—pick one that’s right for you.
  • Do you have a co-founder who will join you? If not, open the letter “When you are selecting a co-founder” next.
  • Do you have the right team to take this on? Often, the best teams have spent much of their time working together before, through good times and bad, with each member bringing something distinctive to the table.
  • Are you comfortable with risk? If you need certainty, being an entrepreneur probably won’t make you very happy. At its core, starting a company is a high-risk/high-reward endeavor.
  • Can you afford to live on a small income for years in advance? You certainly won’t get paid handsomely in the beginning. For example, Eddy Lu (co-founder of one of our portfolio companies, Grubwithus, now called GOAT), slept in his car when he started his company.
  • Do you mind working way harder than ever before, and under conditions of much higher stress? You will wear more hats and have more responsibility than you’ve ever had. You will also be responsible for the well-being of your team, and the satisfaction of your customers.
  • Do you really want to go for years without great benefits, long vacations, work-life balance, etc.? There is no balance when starting a startup!
  • Do you need outside validation? If you need a pat on the back, you may not make a good entrepreneur. You need faith in yourself; you cannot rely on others to keep you going. Find strength in your passion for the idea and your interest in changing the world.
  • How do you deal with rejection and how much grit do you have to pick yourself up and make something out of nothing? Know that conviction is required. You’ll get nothing but pushback all day long, from everyone you encounter—investors, people who use the product or service, people who are testing it out. You cannot get depressed at hearing “no” or that your idea is “stupid.” Instead, you need to be inspired by it.

If you can get through all of my skepticism and doubt, and you still are game for trying, here’s my advice:

  • Go for it! There’s nothing more fun than creating something out of ether.
  • Keep your eyes wide open. Determine the amount of time and resources that you are willing to commit to this project. For example, “I’m going to self-fund up to $100,000 and spend six months testing out my idea,” or “I’m going to commit to this idea/company for the next five years without thinking about anything else.”
  • Make sure your family and friends are supportive of the risk you will take. There will be many sacrifices all around, and everyone needs to be on board and understand the road ahead. Otherwise, you may end up with more pain in your personal life than you desire.
  • Can you dip your toe in the water? Can you start trying to do this while you are still employed? I did this when I created WIN, and my early experience encouraged me to transition more quickly.
  • Once committed, don’t look back and wonder: put all of your energy into making this successful. Pledge total focus and commitment. Building a company is a long-term proposition. Knowing that you’re making a commitment for a decade will give you the perspective you need to make it through the tough moments.

Is it difficult to be an entrepreneur? Absolutely. But it’s also fun (and terrifying at same time). It’s just like caring for a baby. You are excited about the idea, but there are times when everything turns to poop and you’re constantly up in the middle of the night. You are going to be tired and frustrated, but also fulfilled beyond anything you could have imagined.

If that sounds right, you are ready to handle the ups and downs of being an entrepreneur. If not, it’s not your time to have a startup— after all, unlike with a baby, you can’t hire a nanny to do the work for you.

All the best,


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