Mar 26, 2015 · 29m · 20vc
20 VC 022: Letting go of the life we planned and the Power of the Female Narrative with Matthew McCall
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In this episode of The 20 Minute VC, host Harry Stebbings interviews veteran venture capitalist Matthew McCall of Pritzker Group about evergreen capital structures, market cycle discipline, and the vital role of authentic storytelling and female leadership in building successful startups.
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 13.1% of the talking time here. How this is scored →
Harry as informed peer 1.6 Guest teaching 2.6 Guest disagreement 0.3 Harry pushing back 0.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:35 Critique of momentum investing
McCall pushes back against prevailing VC trends, criticizing momentum investing as pumping money blindly and predicting an influx of dead unicorns.
Hardest push from Harry ▶ 13:07 Challenging guest on tech bubble risksStebbings uses McCall's own blog writing and a Steve Jurvetson quote to directly challenge McCall on whether current market valuations constitute a tech bubble.
Biggest teaching moment ▶ 20:00 Disparities in female founder VC fundingMcCall educates Stebbings on industry statistics regarding female founders, noting that while industry-wide funding sits at 4-6%, half of Pritzker's SoCal portfolio is female-led.
Harry holds his own ▶ 13:07 Host cites Jurvetson quote from guest's blogStebbings demonstrates strong preparation by referencing McCall's blog post on 15-year cycles and quoting investor Steve Jurvetson to frame a sharp macroeconomic question.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Matthew McCall's Background and Entry into Venture Capital | 1 | 2 | 0 | 0 | Host asks an open-ended introductory question about McCall's background and interjects politely with minor questions like retro computer memory. McCall comfortably details his transition from athletics and Wall Street into venture capital. | |
| Pritzker Group's Capital Structure and Investment Strategy | 1 | 2 | 0 | 0 | Host asks standard interview questions regarding average investment size and target exit timelines. McCall explains Pritzker Group's unique $7 billion evergreen capital structure and long-term holding flexibility. | |
| Evolution of Investment Strategy and Core Founder Attributes | 1 | 3 | 1 | 0 | Host prompts McCall on how his investment strategy has evolved over the years. McCall offers a thoughtful critique of momentum investing and warns about market cycles and capital efficiency. | |
| Fostering Founder Relationships and the Principle of Karma | 3 | 2 | 0 | 0 | Host shows familiarity with the guest's background story and Dick Costolo's commencement speech. McCall outlines his philosophy that karma and random acts of kindness drive synchronicity in VC dealflow. | |
| Key Traits of Great Founders and Evolutionary Innovation | 4 | 3 | 1 | 0 | Host demonstrates solid research by quoting McCall's blog and Steve Jurvetson to ask about the tech bubble. McCall breaks down historical 15-year venture cycles and market excess indicators. | |
| The Hero's Journey and Storytelling in Entrepreneurship | 1 | 2 | 0 | 0 | Host asks for commencement speech recommendations. McCall elaborates on Joseph Campbell's Hero's Journey framework and its deep relevance to entrepreneurship. | |
| The Rise of Female Entrepreneurs and Purpose-Driven Businesses | 1 | 4 | 0 | 0 | Host asks a simple prompt question on female entrepreneurship. McCall educates the host with striking statistics on female VC funding and explains how storytelling drives viral organic growth for female-led brands. | |
| Lightning Round: Founder Reading List and Storytelling Resources | 1 | 3 | 0 | 0 | Host initiates the lightning round on book recommendations. McCall offers an unconventional reading list focused on storytelling and narrative craft rather than standard business books. |
Statements from this episode (21)
McCall: Pritzker Group manages a $7 billion evergreen capital pool
“So we have, the advantage we have is with the Pritzke Group, we have a seven billion dollar evergreen pool of capital to invest off of.”
McCall: Pritzker Group focuses on $4M–$10M Series A and B checks
“So our core investment focus is series A and B, and that's, you know, four to ten million dollars on the downstroke, but we have a very active seed program we use strategically. It you know, so that can be as little as two 50 or a 100,000, but really our core …”
McCall: Pritzker Group invested $60 million into SMS Assist
“So we've written up to sixty million dollars into a deal. One of my companies, SMS Assist we put fifteen million in. The company was doing well, needed another forty-five million, and we wrote the check.”
McCall: Pritzker Group held one company for 14 years
“So we've got one deal, we're 14 years in, and we're still the only person, we're the only investor writing checks still to support the company.”
McCall: Pritzker Group targets a three-to-five-year holding period
“But our real target is, you know, kind of traditionally a three to five year old.”
McCall: Capital-efficient startups historically outperform momentum-investing bets
“Right now we're in the middle of momentum investing, which is about pumping enormous amounts of money into companies with the hopes that someone else would pump even more money later on. But the strategy that has worked historically the best are those companie…”
McCall: Impending market downturn will result in a wave of dead unicorns
“And you're going to see that happen when the market downturns coming up here you're going to see a bunch of I think, what was it? Bill Gurley said, you're going to see a lot of dead unicorns floating around.”
McCall: Continuous random acts of kindness drive VC success and deal flow
“There's only one rule that I found and we've tried over 20 years, I've been in the business 20 years, we've tried everything under the sun to try and figure out what drives success and what doesn't you know, in terms of predicting, and it's, it really comes do…”
McCall: Every reference during FeedBurner diligence praised Dick Costolo
“And when we were doing our diligence on on FeedBurner with Dick Koslow, what was interesting is every single person I talked to used the same quote. I'm in the Dick Koslow fan club.”
McCall: Applying tech to ugly industries creates strong competitive barriers
“One is an ugly industry where someone is bringing technology in. It's a huge competitive advantage and barrier to entry because in those industries, you either have the domain expertise or you're a technologist, right? But very few people have both.”
McCall: Most innovations combine evolutionary ideas rather than revolutionary breakthroughs
“Very few things are revolutionary Most things are two evolutionary things coming together.”
McCall: Uber was evolutionary mobile-meets-taxis rather than revolutionary
“Uber is not revolutionary. It's evolutionary, right? It's mobile meets, you know, taxis at the end of the day, but it's how it was done.”
McCall: Mutual funds writing $400M tech checks signals late-stage market excess
“Mutual funds coming in and paying outrageous prices and putting four hundred million into companies. These are all signs that were late on the stage.”
McCall: Venture capital is among the first asset classes to lose liquidity
“Venture being a very high risk asset class will be one of the first to lose liquidity.”
McCall: Pritzker Group reduced check sizes to prepare for market correction
“So we've been actually kind of holding our dry powder. We've done some smaller checks in the last 18 months. We've done quite a number of deals, but smaller check sizes, but we're holding our dry powder because it's, it'll, there'll be some really exciting opp…”
McCall: Millennial and female entrepreneurship will define the next 15 years
“So if there's one thing that in my life I want to do from this point forward is is, you know, to talk about the hero's journey, to talk about whatever wisdoms I have, but more importantly is to encourage this incredible batch of entrepreneurs coming through ri…”
McCall: Only 4% to 6% of venture-funded deals have female founders
“I think it's something like four to six percent, which, you know, pretty small.”
McCall: Half of Pritzker Group's SoCal portfolio has female leadership
“I was looking at our Southern California portfolio. We opened up our West Coast office about three years ago. Half are deals. Half are either co-founded or led by female founders.”
McCall: The Honest Company grew from zero to several hundred million in three years
“Jessica Alba at the honest company, right? Which has gone from zero to several hundred million in three years.”