Founder Lessons: A Conversation with Maynard Webb

3 Lessons for Founders from a Conversation with Maynard Webb

Maynard Webb was the former COO of eBay, and now runs a successful venture capital firm, Webb Investment Network, as well as sits on the boards of several public companies including Visa and Salesforce. Maynard created his own success and now shares his best advice through his new book Dear Founder.

Below are the three lessons Maynard shared with founders during our recent Spero Ventures event where we hosted Maynard for a book signing and fireside chat.

Should I start a company?

If you are thinking about starting a company, Maynard presses that you should ask yourself the following three questions.

  1. Are you passionate enough about the company to make several personal sacrifices?
  2. Are you willing to work hard, take risks, and be told “NO” over 50 times a day?
  3. Are you ok with being lonely?

Being a founder is a very lonely job. In fact, probably the most lonely job. You need to be very sure if you are going to take the leap and start your own company. You need to believe in yourself and believe that the world needs what you are creating. If you answered yes to all these questions, it might be time to take the leap and start a company.

What if I fail?

Maynard is a big believer in failing. He knows that may sound funny, but Maynard believes we learn the most from our failures. If you put your all into something and still fail, that will be one of your greatest lessons. Never be ashamed if you dedicate your time and efforts to something that just doesn’t work out. You can always take a break then pick back up again, use what you learned and get to work.

He also emphasizes that we are our biggest roadblocks. We often are the ones who are holding ourselves back the most. Once you become ok with failing you will become far more successful. As a founder you must acknowledge that you will fail all the time, and if you believe in yourself and what you are doing, failures can’t hold you back.

How do I think about legacy?

When Maynard left his COO role at eBay, they dedicated the park benches in the courtyard to him with one of his quotes on each bench. He has reflected on sitting on one of those benches long after he was retired and wonders if people would say hello or turn and walk away. He wants to be one that others would come say hello to. Here are three things that he believes will help you build your legacy.

  1. Remember you are gaining and losing credibility every single day.
  2. Apologize often.
  3. Be human.

He stresses that being human is the most important. We are all living this life together side by side, so be kind and take time to invest in the people in your life. These people will become your greatest assets in both your professional and personal life.

If you are considering becoming a founder, read Maynard’s book, Dear Founder. It will leave you feeling like you are sitting on a park bench with Maynard getting some wonderful advice.

Watch the video of Maynard Webb’s fireside chat with our partner, Shripriya Mahesh