20VC: True Ventures' Toni Schneider on How Being CEO @ Automattic (Wordpress) Made Him A Better Investor, The Biggest Lessons from Automattic on Running Successful Remote Teams and The Right Way For Investors To Show Founders They Have Their Support (Note
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC
4.4 • 637 Ratings
🗓️ 16 March 2020
⏱️ 32 minutes
🧾️ Download transcript
Summary
Toni Schneider is a Partner @ True Ventures, one of the valley's leading early-stage firms with a portfolio including the likes of Peloton, Hashicorp, Fitbit, Automattic (Wordpress) and Tray.io to name a few. As for Toni, he has spent 14 years as a Partner @ True but during that tenure, he was also the CEO of Automattic for 8 years where he helped WordPress.com become a top 10 global internet destination with close to a billion monthly visitors. Before that, he was a VP @ Yahoo post their acquisition of the company he was CEO of Oddpost, much of their work formed the basis for Yahoo mail.
(Note: Recorded Pre-Coronavirus)
In Today’s Episode You Will Learn:
1.) How Toni made his way into the world of venture following two turns in the seat of CEO and then joining Yahoo?
2.) Does Toni fundamentally believe it helps when investing to have been both an operator with Automattic and Partner @ True? How did being CEO @ Automattic shape how he thinks about investing today? How did Toni manage the balancing act of a being a CEO and Partner at a venture fund for 7 years? Having been a CEO and having worked with the best, what does Toni believe are the qualities that make the great CEO of today?
3.) Why does Toni believe that startups do not have to be as stressful as they are or are portrayed to be? How does Toni deal with the shit hit the fan moments? What can an investor do in times of high stress when the founder is not performing? What is the right way for them to express that the performance is not where it needs to be? On the flip side, what is the right way for investors to show their support to the founders?
4.) What are Toni's biggest learnings from the Wordpress days on what it takes to run a truly successful remote team? Where does Toni see many people going wrong today? What does Toni advise those considering going remote first? What does Toni believe are the biggest pros and cons of the model? What infrastructure does one need to have in place to make it seamless? Does it still make sense for companies to be in the valley?
Items Mentioned In Today’s Show:
Toni’s Fave Book: Their Eyes Were Watching God, Predictably Irrational: The Hidden Forces That Shape Our Decisions
Toni’s Most Recent Investment: Piavita
As always you can follow Harry, The Twenty Minute VC and Toni on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript
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| 0:00.0 | Welcome to the 20 Minervi with me, Harry Stebbingz. As always, you can see more from us and me |
| 0:03.9 | behind the scenes on Instagram at H. Stebbing's 1996 with two Bs. I really do always love to hear |
| 0:08.9 | your thoughts on the show there. However, to the show today, and what an investor slash operator |
| 0:13.2 | we have in the hot seat joining us. And so with that, I'm super excited to welcome Tony Schneider, |
| 0:17.8 | partner at True Ventures, one of the valleys leading early stage firms |
| 0:21.0 | with the portfolio, including the likes of Peloton, HashiCorp, Fitbit, Automatic, and Trade.io, |
| 0:26.9 | to name a few. As for Tony, he spent 14 years as a partner at True, but during that tenure, |
| 0:31.8 | he was also the CEO of Automatic for eight years, where he helped WordPress.com become a top |
| 0:36.5 | 10 global internet destination |
| 0:38.2 | with close to a billion monthly visitors. Before that, he was a VP at Yahoo! Post their |
| 0:42.6 | acquisition of the company he was CEO at, Odd Post. Much of their work formed the basis for |
| 0:47.1 | Yahoo Mail. Due to his many successes, he's also won numerous awards, including startup CEO |
| 0:51.7 | of the year at the Crunchies. And I'd also want to say huge thank you. |
| 0:54.5 | This really was a team effort. Sam Shank at Airbnb, Phil Black, Tony Conrad, John Callahan and |
| 0:59.8 | Nick Mater at Gainesite for some fantastic questions suggestions today. I really did so appreciate that. |
| 1:05.0 | Before we move into the show today, though, I wanted to take a moment to mention HelloSign, |
| 1:08.6 | a great example of a company that found success in building a product focused on user experience. HelloSign is an effortless e-signature |
| 1:15.5 | solution used by millions to securely send and request legally valid digital signatures and |
| 1:21.0 | agreements. They raised a total of $16 million in funding and recently got acquired by Dropbox |
| 1:25.7 | for an impressive $230 million. Check out |
| 1:28.6 | HelloSign.com forward slash 20VC to join the thousands of companies and founders, including |
| 1:34.0 | me, who value fast, secure and simple e-signatures. It really is a must. And speaking of amazing |
... |
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