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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

Mar 16, 2020

Toni Schneider, a Partner at True Ventures and former CEO of Automattic, shares his fascinating journey from leading WordPress to venture capital. He discusses how his CEO experience shapes his investment style and insights on the qualities of a successful modern CEO. Toni believes startups can be less stressful than often portrayed and emphasizes the importance of supportive investor-founder relationships during tough times. He also reflects on lessons from the remote work era at Automattic and shares exciting investment opportunities in innovative businesses.

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ANECDOTE

Founder to VC

Toni Schneider's venture capital journey began as a startup founder, raising money for Oddpost and Uplister.
This experience led him to co-found True Ventures, aiming to create a founder-friendly firm.

INSIGHT

Operator Advantage

While not a requirement, operational experience helps VCs connect with founders.
Having "walked a mile in their shoes" fosters understanding and empathy.

ADVICE

Ruthless Prioritization

Focus on a few key priorities, ruthlessly dropping others to minimize stress.
Toni Schneider's experience at Automattic showed that deep focus, not breadth, drives success.

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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

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