Mar 16, 2020 · 31m · 20vc
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
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Toni Schneider, partner at True Ventures and former CEO of Automattic, to discuss balancing venture investing with operational leadership, managing high-performing remote teams, and guiding early-stage founders through prioritization and culture building.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 38.4% of the talking time here. How this is scored →
Harry as informed peer 2.3 Guest teaching 4.4 Guest disagreement 0.9 Harry pushing back 2.6
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 10:34 Rejecting the compressed timeline premise
Tony politely disagrees with Harry's concern about compressed round timelines, stating he does not feel early-stage deals are actually that rushed.
Hardest push from Harry ▶ 21:59 Host challenges remote enterprise sales modelHarry directly counters Tony's remote work advocacy by citing a deal he turned down specifically because the enterprise sales team was fully distributed.
Biggest teaching moment ▶ 22:23 Explaining role-dependent geography in remote companiesTony educates Harry on how distributed companies handle geography, explaining that role-specific requirements like sales can be targeted geographically while keeping the core organization distributed.
Harry holds his own ▶ 21:59 Host brings VC deal thesis into debateHarry leverages his own experience as an investor to present a clear counter-argument regarding enterprise sales coverage.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Joining True Ventures and Automattic Simultaneously | 1 | 3 | 0 | 1 | Harry welcomes Tony and asks standard background questions about his simultaneous entry into True Ventures and Automattic. Tony explains the founder-friendly ethos behind True Ventures. | |
| Dual Mindset: Balancing Investor and CEO Roles | 2 | 3 | 1 | 2 | Harry asks directly whether operational experience is necessary for VCs, prompting Tony to explain why it helps him connect with founders while acknowledging it is not mandatory. | |
| Qualities of Great Founders and Balancing Ambition with Realism | 3 | 5 | 3 | 4 | Harry questions how investors can assess founder focus during compressed fundraising timelines. Tony counters Harry's premise, noting early-stage investing provides ample time before rapid growth. | |
| Ruthless Prioritization and Reducing Startup Stress | 3 | 4 | 0 | 3 | Harry asks probing follow-ups on operational stress and whether Automattic's ruthless prioritization strategy scales. Tony outlines their monthly priority trimming process. | |
| Performance Feedback, Founder Identity, and Personal Evolution | 1 | 6 | 0 | 0 | Harry turns the conversation into a personal mentorship session, asking how to manage founder feedback and separate personal identity from business struggles. Tony offers detailed executive coaching. | |
| Missed Investment Opportunities and the Distributed Work Model | 4 | 6 | 2 | 5 | Harry challenges Tony's pro-remote thesis by citing a deal he personally rejected due to a remote enterprise sales team. Tony educates Harry on differentiating role-based geography needs from overall company structure. | |
| Decentralization of Tech Hubs and Maintaining Human Connection | 2 | 4 | 0 | 3 | Tony highlights True's non-Silicon Valley investments, while Harry brings up the difficulty of evaluating founder chemistry over Zoom. Tony validates the challenge and stresses the need for periodic in-person meetups. |
Statements from this episode (16)
Schneider: Automattic experience represents only 25% of investment approach
“Even though my automatic experience is probably only a small part of my investment approach today, you know, maybe 25%, the rest is really based on being part of the team at True, and like I said before, we're a very collaborative group, and we're committed to…”
Schneider balanced VC partner and Automattic CEO roles for eight years
“It was actually eight years of doing both of those jobs.”
Schneider: James Freeman spent 10 years perfecting Blue Bottle's experience
“Take, for example, James Freeman from Blue Bottle Coffee. He went super deep into every detail of creating a great coffee experience. The origin of the coffee beans, the experience of walking into a cafe, the smell, the weight, the preparation of the drink, th…”
Schneider: True Ventures gets up to two years with early product-focused founders
“I don't really feel like it's that compressed, to be honest. I mean, it does, you know, when a startup takes off, it does move quickly, but I feel like we get involved so early. We actually have a good amount of time on that first year or two when it's just pe…”
Schneider: Automattic selected only 3-4 monthly priorities from 30+ potential tasks
“Matt and I always kept a running list of all the things we wanted to work on, or maybe should be working on at some point, and Usually had like dirty or 40 things on it, probably even more because there's a lot of growth and a lot of ideas everywhere. And then…”
Schneider: Single-list task prioritization scales up to 100 employees
“I think it definitely scales. I mean, you can get to, you know, maybe 50 to a hundred people, where you can almost keep that just one list approach, and then you scale it by spreading across your management team and different parts of your business and making …”
Schneider: True Ventures passed on Instagram before its pivot
“So for example, we looked at Instagram really early and it was literally a different product with a different name and we passed on it and then they later pivoted to Instagram. But by then it was too late for us to invest.”
Schneider: Predicting successful startup pivots is impossible
“So now a successful pivot is impossible to predict and, you know, be a lousy investment strategy.”
Schneider: Remote software development teams will outcompete centralized teams
“And I believe that if you work on something that can be done by a remote team, software development being a prime example, That team will win because you have access to a global talent pool, and you have people who are happy and empowered because they get to w…”
Schneider: Fully distributed organizations outperform centralized companies with remote teams
“They try to build a centralized company with some remote teams instead of going all in and building a fully distributed company, which I just think is a better approach, and I advise every company I work with to at least consider that model.”
Stebbings passed on enterprise software startup over remote sales structure
“I turned it down because of largely this reason. There were other reasons, but it was largely this reason.”
Schneider: True Ventures' three recent major exits were outside Silicon Valley
“If you look at the True Ventures portfolio, we had three very big exits over the last two years. Ring.com to Amazon, Duo Security to Cisco, and most recently, the Peloton IPO. Now, these three companies have one intriguing thing in common. They were all built …”
Schneider: True Ventures holds 75% of its investments outside Silicon Valley
“Right now, I would say about a quarter of our investments are in Silicon Valley, about half are in the rest of the U S US, and then another Quarter or so in the rest of the world, primarily Europe and Africa”
Schneider: Remote teams must meet in person at least twice yearly
“In automatic experience, I think once or twice a year for a team is enough to Get together, but you have to do that, and you can't slack off on it.”
Schneider: Conventional wisdom views decarbonization as a poor VC fit
“Right now, I'm learning or trying to learn about decarbonization to see if there's a seed stage investment opportunity in that space, and it's been challenging because it's a totally new area for me, and also the conventional wisdom is that it's not a good pla…”
Schneider praises Ellen Pao as a thoughtful, high-impact board member
“One example of a strong board member who has been a pleasure to work with for me is Ellen Pau from Project Include. I sit on a board with her in a diversity data analytics company called Typica, and Ellen has been very thoughtful and high impact, and she's som…”