20VC: How The Best Founders Approach Bet The Company Decisions, How to Put Your Board to Work & How To Optimise Strategic Thinking on Boards with Maynard Webb, Founder @ Webb Investment Network & Everwise
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 28 September 2018
⏱️ 33 minutes
🔗️ Recording | iTunes | RSS
🧾️ Download transcript
Summary
Maynard Webb is truly unique, he has worn 3 different hats and excelled in all of them. First, he is the Founder of The Webb Investment Network, the institutionalisation of his personal investing where he has invested in the likes of Zuora, GOAT, WePay, Okta, PagerDuty and many more incredible companies. He is also a Co-Founder and Board Member at Everwise, the startup that helps companies tailor, scale and run training at enterprise scale. Everwise has raised over $26m in funding from the likes of Sequoia Capital and Canvas Ventures. Finally, Maynard sits on the board of some of the biggest companies of our time including Salesforce and Visa. Previously Maynard was Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay.
In Today’s Episode You Will Learn:
1.) How Maynard made his way into the world of startups and came to invest in his first company, founded by Sequoia's Jim Goetz and how that led to eBay, LiveOps and more?
2.) Does Maynard believe we have an excess supply of capital in the market today? What does Maynard think of the mega $Bn+ funds being raised on a frequent basis? How does this distort pricing in the market? How does Maynard think about his own price sensitivity? What does this mean for his available reserve allocation?
3.) Does Maynard believe that the dominant role of CEO is management upscaling? How does Maynard advise on the transition from manager to inspirational leader? How do the vest best CEOs hire the very best execs? How does Maynard know when a stretch VP is a stretch too far? How should founders determine and approach "bet the company" decisions?
4.) When should a founder start installing their board? What does Maynard believe is the optimal board construction, both in characters and profiles? How has Maynard seen his own style of board membership changed over the years? What are the best board members talk to listen ratios? How can founders create alignment among their board?
5.) What is the right way for founders to deal with "s*** hit the fan moments"? What is the framework to approach this with? Where do many go wrong in their approach? How does one communicate this to the wider team, investors and board? What have been Maynard's biggest personal learnings here from eBay?
Items Mentioned In Today’s Show:
Maynard’s Fave Book: The Better Angels of Our Nature
As always you can follow Harry, The Twenty Minute VC and Maynard on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | You are listening to The 20 minute VC with me, Harry Stebbings. It would be really great to see you on Instagram, |
| 0:04.7 | mostly a combination of mehitos and workouts, but always love to connect with you there at H. Stebbings, |
| 0:09.5 | 1996 with two bees. Now, for the show today, and honestly, I have absolutely no idea how I'm going |
| 0:15.3 | to succinctly describe all the incredible achievements of our guests into a short intro, but wish me luck, |
| 0:20.4 | and here goes. |
| 0:21.4 | So Maynard Webb is truly unique. He's worn three different hats and excelled in all of them. |
| 0:26.3 | First, he's the founder of the Web Investment Network, the institutionalisation of his |
| 0:30.0 | personal investing, where he's invested in the likes of Zora, Goat, Weepay, Octa, Pager Duty and many more |
| 0:36.3 | incredible companies. |
| 0:41.9 | He's also a co-founder and board member at Everwise, the startup that helps companies tailor, |
| 0:44.4 | scale and run training at enterprise scale. |
| 0:49.5 | Everwise has raised over $26 million in funding from the lights of Sequoia Capital and Canvas Ventures. |
| 0:50.3 | And finally, Maynard sits on the board of some of the biggest companies of our time, including |
| 0:54.1 | Salesforce and Visa. |
| 0:55.9 | Previously, Maynard was chairman of the board of Yahoo. |
| 0:58.5 | He was the CEO of LiveOps and C-O-O of eBay. |
| 1:01.9 | Incredible career? |
| 1:02.9 | Well, Maynard has distilled these incredible learnings from the career into a brilliant, |
| 1:07.3 | brilliant book, Dear Founder, which we discuss in the episode, and you can find the link on our site. And I do have to say a huge thank you to Eddie Liu at Goat. For the |
| 1:14.6 | intro to Maynard today, I really am so grateful for that, Eddie. But before we welcome the man |
| 1:18.7 | himself, thanks to my friends at Weepa. Let's talk about another cool player in the space we love. |
| 1:23.3 | Team Snap. Team Snap is a sports team management app that makes communication and organization a breeze. |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from The Twenty Minute VC, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of The Twenty Minute VC and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2025.