Mar 14, 2016 · 36m · 20vc
20VC: Lowercase's Matt Mazzeo on Being Chris Sacca's Partner and The 3 KPIs to Successful Investing
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In this episode of The 20 Minute VC, host Harry Stebbings interviews Matt Mazzeo, Managing Director at Lowercase Capital, to discuss his transition from CAA to venture capital, his partnership with Chris Sacca, and his operational framework for seed investing. Mazzeo shares key insights on venture KPIs, founder support tools, modern personal branding, and maintaining ethical integrity in early-stage investing.
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 24.9% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 3.4 Guest disagreement 1.4 Harry pushing back 1.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:20 Matt defends high meeting volume
Matt pushes back against Harry's premise that filling a calendar with meetings is unproductive, arguing that in-person connections are his most valuable analog brand-building tool.
Hardest push from Harry ▶ 17:17 Harry questions busywork vs productivityHarry directly challenges Matt's open-door strategy by asking if taking more meetings than anyone else creates a schedule that is busy rather than productive.
Biggest teaching moment ▶ 29:24 Matt redefines the concept of hustleMatt corrects conventional startup jargon around 'hustle', reframing it away from short-term transactional favors into selfless value creation without expecting immediate payback.
Harry holds his own ▶ 6:55 Harry cites Sacca's exact quoteHarry demonstrates strong preparation by pulling a specific quote from Chris Sacca about 'washing the suit off' Matt, surprising the guest with his deep research.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| How Matt Mazzeo Met Chris Sacca at SXSW | 2 | 2 | 1 | 1 | Harry sets up the interview by noting he listened to five hours of Matt's previous appearances. Matt warmly recounts meeting Chris Sacca over wine at South by Southwest and engaging in spirited debates with early tech founders. | |
| Transition from CAA to Lowercase & Sacca's Culture | 3 | 3 | 1 | 2 | Harry demonstrates deep prep by referencing Sacca's specific quote about wanting to 'wash the suit off' Matt after his CAA background. Matt explains the mindset shift from being a behind-the-scenes talent agent to a public-facing VC. | |
| Brand Transparency & Location Dynamics in VC | 3 | 4 | 2 | 2 | Matt outlines how VC is shifting away from Sand Hill Road addresses toward individual transparency and founder de-risking. Harry presses Matt on whether operating out of Los Angeles creates geographic disadvantages relative to Silicon Valley. | |
| Personal Branding, Media Channels, and In-Person Meetings | 3 | 3 | 2 | 3 | Harry offers pushback when Matt describes taking an abnormally high volume of in-person meetings, questioning if that is 'busy, but not productive.' Matt defends his approach as analog relationship building. | |
| Matt Mazzeo's 3 Investing KPIs: Site, Selection, and Service | 3 | 4 | 1 | 2 | Harry references Hunter Walk's framework to prompt Matt on his personal KPIs. Matt breaks down his three core pillars (Site, Selection, Service) and explains how hard it is to judge early-stage selection feedback loops. | |
| Evolving Decision-Making & Introducing Lowercase Alpha | 2 | 4 | 1 | 1 | Matt discusses how his decision-making process balances pattern matching with fighting personal biases. He introduces Lowercase Alpha, a product built to help early portfolio companies gather beta tester feedback. | |
| Quick Fire Round: Randomness, Personal Roots, and Hustle | 1 | 4 | 2 | 1 | During the quick fire round, Matt shares a personal story about his father getting sick and redefines 'hustle' as delivering value to others without expecting a transactional short-term return. | |
| Media Choices, Sacca's Influence, and the 'Icky Rule' | 2 | 3 | 1 | 2 | Matt discusses working with Chris Sacca and introduces their firm's 'Icky Rule' for walking away from morally questionable deals. Harry asks for specific details on what triggers the rule. |
Statements from this episode (15)
Matt Mazzeo manages over 40 investments at Lowercase Capital
“At Lowercase, Matt manages a portfolio of over 40 investments.”
Mazzeo: Venture capital is shifting toward public personality and thought leadership
“Increasingly, I think we're seeing, we've been talking a little bit about this, Harry, like that shift in venture towards being more of a personality and expressing yourself and not being you know, a wilting lily and sort of going out there. And being more fro…”
Mazzeo: Venture Capital Firms Can No Longer Rely Solely On Sand Hill Road
“I don't think the VC of today can hang behind a Sand Hill Road address anymore, and pretend like that brand will become, or maintain its supremacy In this ecosystem.”
Mazzeo: Y Combinator shares detailed background notes on investors with founders
“I think one of the fantastic things about YC and what Paul and Sam have built is that they, ah, they expose entrepreneurs to more information than ever before. That's not just the deal making terms. That's background on the investors that they're getting into …”
Mazzeo: Product Hunt Is a Critical Ecosystem for Seed VC
“Product Hunt is a community I've been a huge supporter of, like you, and sort of it's a, it's an ecosystem that I love, and it turned out to be a really important one for early stage venture, because that's where you find a bunch of really interesting companie…”
Mazzeo: Cheap capital has muddled follow-on funding as a startup success signal
“Follow on funding is something that today because of the fundraising environment and cheap and cheap access to capital, You're seeing perhaps a little too much exuberance in terms of like the fall on financing. So that, that signal has gotten a little bit mudd…”
Mazzeo: Lowercase's best deal flow comes from portfolio and passed founders
“That's where we see most of our high profile, our most successful deal flow comes from the existing portfolio and entrepreneurs that even entrepreneurs that we pass on that that send us deals.”
Mazzeo: Andreessen Horowitz modeled its VC platform team on CAA
“As you've seen firms build out and scale up, And hire a lot of people to sort of better help, largely based on the CAA model in Andreessen's case to better help service clients by surrounding them with experts in hiring and marketing and distribution and busin…”
Mazzeo: Lowercase will build software to source portfolio beta testers
“What you're going to see us try to do over the next few years is build out scalable versions of that, that help, help portfolio companies from like, how do we get a first few thousand beta testers on our platform playing with a product prior to release?”
Mazzeo: Lowercase launched text-based beta testing platform Lowercase Alpha
“The product called lowercase apple, which is just a text message group that anybody can subscribe to, and get products every week or two. That are still in early test flight mode that are generally alphas or betas of products.”
Mazzeo: Venture capital is a lonely career built on defending non-consensus deals
“This career is the venture career, even if you're part of a partnership, can be a lonely one. You're often standing out on a ledge defending investments when people still think they're crazy, and often the best ones are and you sort of have to defend that”
Mazzeo: Lowercase Capital operates without an office with three remote employees
“We don't have an office. I work from home. I had three people a foot away from me at CA, and today we have three people spread across you know, a few cities in in lowercase”
Mazzeo: Chris Sacca walked away from tens of millions over 'icky' deals
“Watched him walk away from tens of millions of dollars repeatedly because he didn't feel right about, and it felt icky to him in that investment. Actually, that's the only, like, that's the only red flag no black ball that we have is if an investment makes us …”
Mazzeo: Lowercase Capital evaluates pro-rata follow-ons as brand new deals
“Mob Crush, live streaming, mobile games. We did the seed there, but we followed on into another round of funding. We treat all of those following and pro rata opportunities. As a, as separate investments in, in terms of our thinking of whether to do them or no…”
Mazzeo in 2016: Interactive live streaming integrated with mobile games will explode
“I think people really underestimate layering video content in context around games and apps, and I think of those mobile games that people spend so much time in as the formats of the future, and so we really don't think about them as, like, as a format, but it…”