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Jan 15, 2016 · 24m · 20vc

20 VC FF 030: Gimlet Media's Matt Lieber on The Future of Podcasting and Life @ Gimlet

Matt Lieber · 15m spoken Harry Stebbings · 6m spoken
0:00 / 0:00

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 Matt Lieber, co-founder and president of Gimlet Media, to discuss the evolution of digital audio, Gimlet's narrative editorial strategy, venture capital fundraising, and podcast monetization models.

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 28% of the talking time here. How this is scored →

Harry as informed peer 3.4 Guest teaching 3.8 Guest disagreement 1.8 Harry pushing back 2.4
05100:0010:0020:001:48–6:26 · Harry as informed peer 2/10 Matt Lieber's Journey from Public Radio to Gimlet Media Harry asks standard background questions about Matt Lieber's transition from radio and consulting to founding Gimlet. Lieber explains the structural gatekeeping in traditional radio syndication that drove him toward digital podcasting. The conversation remains friendly and conversational with minor host follow-ups.6:26–11:15 · Harry as informed peer 3/10 Navigating Gimlet's Series A Fundraising and Creative Risk Harry references specific details from Gimlet's pitch episode regarding Series A funding constraints. Lieber reframes standard venture expectations by highlighting how Gimlet prioritized early advertising cash flow over pure user growth curves. He also details how capital allows Gimlet to take creative risks on novel audio formats.11:15–15:24 · Harry as informed peer 4/10 Preserving Company Culture and Partnering with Lead Investors Harry quotes co-founder Alex Blumberg's concerns about culture degrading as the team expands. Lieber outlines Gimlet's internal mentorship program, Gimlet Guides, designed to preserve company identity. He also discusses choosing strategic partner fit over maximizing valuation in their Series A.15:34–20:07 · Harry as informed peer 5/10 Podcasting Market Opportunities and Show Development Strategy Harry actively challenges the prevailing VC consensus that podcasting is an uninvestable sector, aligning with Lieber's market vision. Lieber outlines the market scale by contrasting mobile ad monetization with traditional radio revenue. The exchange displays host initiative in challenging broader industry skepticism.20:08–23:43 · Harry as informed peer 3/10 Quick Fire Round with Matt Lieber During the quick fire round, Harry offers Steve Jobs as his ideal founder, prompting a sharp reaction from Lieber. Lieber directly critiques Jobs's management style and monomaniacal behavior, refusing to adopt him as a model. Harry briefly defends his perspective before moving on through the remaining rapid-fire questions.1:48–6:26 · Guest teaching 3/10 Matt Lieber's Journey from Public Radio to Gimlet Media Harry asks standard background questions about Matt Lieber's transition from radio and consulting to founding Gimlet. Lieber explains the structural gatekeeping in traditional radio syndication that drove him toward digital podcasting. The conversation remains friendly and conversational with minor host follow-ups.6:26–11:15 · Guest teaching 4/10 Navigating Gimlet's Series A Fundraising and Creative Risk Harry references specific details from Gimlet's pitch episode regarding Series A funding constraints. Lieber reframes standard venture expectations by highlighting how Gimlet prioritized early advertising cash flow over pure user growth curves. He also details how capital allows Gimlet to take creative risks on novel audio formats.11:15–15:24 · Guest teaching 3/10 Preserving Company Culture and Partnering with Lead Investors Harry quotes co-founder Alex Blumberg's concerns about culture degrading as the team expands. Lieber outlines Gimlet's internal mentorship program, Gimlet Guides, designed to preserve company identity. He also discusses choosing strategic partner fit over maximizing valuation in their Series A.15:34–20:07 · Guest teaching 4/10 Podcasting Market Opportunities and Show Development Strategy Harry actively challenges the prevailing VC consensus that podcasting is an uninvestable sector, aligning with Lieber's market vision. Lieber outlines the market scale by contrasting mobile ad monetization with traditional radio revenue. The exchange displays host initiative in challenging broader industry skepticism.20:08–23:43 · Guest teaching 5/10 Quick Fire Round with Matt Lieber During the quick fire round, Harry offers Steve Jobs as his ideal founder, prompting a sharp reaction from Lieber. Lieber directly critiques Jobs's management style and monomaniacal behavior, refusing to adopt him as a model. Harry briefly defends his perspective before moving on through the remaining rapid-fire questions.1:48–6:26 · Guest disagreement 1/10 Matt Lieber's Journey from Public Radio to Gimlet Media Harry asks standard background questions about Matt Lieber's transition from radio and consulting to founding Gimlet. Lieber explains the structural gatekeeping in traditional radio syndication that drove him toward digital podcasting. The conversation remains friendly and conversational with minor host follow-ups.6:26–11:15 · Guest disagreement 2/10 Navigating Gimlet's Series A Fundraising and Creative Risk Harry references specific details from Gimlet's pitch episode regarding Series A funding constraints. Lieber reframes standard venture expectations by highlighting how Gimlet prioritized early advertising cash flow over pure user growth curves. He also details how capital allows Gimlet to take creative risks on novel audio formats.11:15–15:24 · Guest disagreement 1/10 Preserving Company Culture and Partnering with Lead Investors Harry quotes co-founder Alex Blumberg's concerns about culture degrading as the team expands. Lieber outlines Gimlet's internal mentorship program, Gimlet Guides, designed to preserve company identity. He also discusses choosing strategic partner fit over maximizing valuation in their Series A.15:34–20:07 · Guest disagreement 1/10 Podcasting Market Opportunities and Show Development Strategy Harry actively challenges the prevailing VC consensus that podcasting is an uninvestable sector, aligning with Lieber's market vision. Lieber outlines the market scale by contrasting mobile ad monetization with traditional radio revenue. The exchange displays host initiative in challenging broader industry skepticism.20:08–23:43 · Guest disagreement 4/10 Quick Fire Round with Matt Lieber During the quick fire round, Harry offers Steve Jobs as his ideal founder, prompting a sharp reaction from Lieber. Lieber directly critiques Jobs's management style and monomaniacal behavior, refusing to adopt him as a model. Harry briefly defends his perspective before moving on through the remaining rapid-fire questions.1:48–6:26 · Harry pushing back 2/10 Matt Lieber's Journey from Public Radio to Gimlet Media Harry asks standard background questions about Matt Lieber's transition from radio and consulting to founding Gimlet. Lieber explains the structural gatekeeping in traditional radio syndication that drove him toward digital podcasting. The conversation remains friendly and conversational with minor host follow-ups.6:26–11:15 · Harry pushing back 2/10 Navigating Gimlet's Series A Fundraising and Creative Risk Harry references specific details from Gimlet's pitch episode regarding Series A funding constraints. Lieber reframes standard venture expectations by highlighting how Gimlet prioritized early advertising cash flow over pure user growth curves. He also details how capital allows Gimlet to take creative risks on novel audio formats.11:15–15:24 · Harry pushing back 2/10 Preserving Company Culture and Partnering with Lead Investors Harry quotes co-founder Alex Blumberg's concerns about culture degrading as the team expands. Lieber outlines Gimlet's internal mentorship program, Gimlet Guides, designed to preserve company identity. He also discusses choosing strategic partner fit over maximizing valuation in their Series A.15:34–20:07 · Harry pushing back 3/10 Podcasting Market Opportunities and Show Development Strategy Harry actively challenges the prevailing VC consensus that podcasting is an uninvestable sector, aligning with Lieber's market vision. Lieber outlines the market scale by contrasting mobile ad monetization with traditional radio revenue. The exchange displays host initiative in challenging broader industry skepticism.20:08–23:43 · Harry pushing back 3/10 Quick Fire Round with Matt Lieber During the quick fire round, Harry offers Steve Jobs as his ideal founder, prompting a sharp reaction from Lieber. Lieber directly critiques Jobs's management style and monomaniacal behavior, refusing to adopt him as a model. Harry briefly defends his perspective before moving on through the remaining rapid-fire questions.

speaking balance: gold is Harry, purple is the guest (3 minute bins)

0:00 · Harry 61.8% · guest 38.2%0:00 · Harry 61.8% · guest 38.2%3:00 · Harry 18.9% · guest 81.1%3:00 · Harry 18.9% · guest 81.1%6:00 · Harry 12.6% · guest 87.4%6:00 · Harry 12.6% · guest 87.4%9:00 · Harry 26.1% · guest 73.9%9:00 · Harry 26.1% · guest 73.9%12:00 · Harry 13% · guest 87%12:00 · Harry 13% · guest 87%15:00 · Harry 16.8% · guest 83.2%15:00 · Harry 16.8% · guest 83.2%18:00 · Harry 34.3% · guest 65.7%18:00 · Harry 34.3% · guest 65.7%21:00 · Harry 31.7% · guest 68.3%21:00 · Harry 31.7% · guest 68.3%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 20:37 Matt's Rejection of the Steve Jobs Ideal

When Harry brings up Steve Jobs as his benchmark founder, Matt immediately interrupts with 'Oh my god' and openly rejects Jobs's management style, citing monomaniacal behaviors he wouldn't want to emulate.

 Hardest push from Harry ▶ 15:24 Harry Pushes Back on VC Podcast Skepticism

Harry explicitly rejects the common assertion from 90% of venture capitalists that podcasting is not an investable market, calling the view infuriating.

 Biggest teaching moment ▶ 6:49 Matt Explains Cash-Flow vs Silicon Valley Growth Models

Matt contrasts typical Silicon Valley VC logic—which urges ignoring revenue for rapid user growth—with Gimlet's strategy of treating ads as part of the core product to establish early self-sustainability.

 Harry holds his own ▶ 15:24 Harry Cites Industry Conversations to Defend Podcasting

Harry demonstrates sector knowledge by citing direct conversations with VCs about market size and monetization potential, arguing forcefully for the industry's upside.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Matt Lieber's Journey from Public Radio to Gimlet Media 2312 Harry asks standard background questions about Matt Lieber's transition from radio and consulting to founding Gimlet. Lieber explains the structural gatekeeping in traditional radio syndication that drove him toward digital podcasting. The conversation remains friendly and conversational with minor host follow-ups.
Navigating Gimlet's Series A Fundraising and Creative Risk 3422 Harry references specific details from Gimlet's pitch episode regarding Series A funding constraints. Lieber reframes standard venture expectations by highlighting how Gimlet prioritized early advertising cash flow over pure user growth curves. He also details how capital allows Gimlet to take creative risks on novel audio formats.
Preserving Company Culture and Partnering with Lead Investors 4312 Harry quotes co-founder Alex Blumberg's concerns about culture degrading as the team expands. Lieber outlines Gimlet's internal mentorship program, Gimlet Guides, designed to preserve company identity. He also discusses choosing strategic partner fit over maximizing valuation in their Series A.
Podcasting Market Opportunities and Show Development Strategy 5413 Harry actively challenges the prevailing VC consensus that podcasting is an uninvestable sector, aligning with Lieber's market vision. Lieber outlines the market scale by contrasting mobile ad monetization with traditional radio revenue. The exchange displays host initiative in challenging broader industry skepticism.
Quick Fire Round with Matt Lieber 3543 During the quick fire round, Harry offers Steve Jobs as his ideal founder, prompting a sharp reaction from Lieber. Lieber directly critiques Jobs's management style and monomaniacal behavior, refusing to adopt him as a model. Harry briefly defends his perspective before moving on through the remaining rapid-fire questions.

Statements from this episode (8)

Assertion Supported
Gimlet Media generated revenue from inception through podcast ad sales
“Unlike, I think, most sort of Silicon Valley startups that have started in the last year or two, we had revenue from the very beginning, because we were selling advertisements on our show.”
Matt Lieber Jan 15, 2016 ▶ 6:56
Disclosure
VCs told Gimlet Media to ignore revenue and focus on user growth
“We had conversations with some VCs who we would begin to talk about revenue, and they're like, we don't want to hear it. We're not actually interested in that. We want to see just a really steep user growth curve, and like, we know that if you get a large audi…”
Matt Lieber Jan 15, 2016 ▶ 7:13
Disclosure
Gimlet co-founders retained over 50% voting control after Series A
“It was really important to Alex and I that we both still controlled our own destiny, that we controlled more than 50% of the company, and we wanted to have a small board.”
Matt Lieber Jan 15, 2016 ▶ 15:03
Opinion
Podcasting is a hot sector with very few investable companies
“The round went very well, and there was a lot of interest in our company because podcasting is kind of a hot space, but there aren't A lot of investable companies in this space.”
Matt Lieber Jan 15, 2016 ▶ 15:12
Disclosure
Lieber: 80% of Gimlet Media's listening happens on mobile
“We're totally mobile media company. It's like 80% of our listening happens on mobile devices.”
Matt Lieber Jan 15, 2016 ▶ 16:57
Disclosure
Lieber: Mystery Show leads Gimlet Media in downloads per episode
“If you look at, like, downloads per episode, Mystery Show is is the biggest, and, but Reply All and Startup are not far behind.”
Matt Lieber Jan 15, 2016 ▶ 19:56
Opinion
Founders should not emulate Steve Jobs' monomaniacal management behaviors
“He is a revolutionary, and he's a visionary, and he created incredible products that changed the world, but he, I don't think people loved working for him, and I think that he also has, like, monomaniacal behaviors that I would not want to adopt, because that'…”
Matt Lieber Jan 15, 2016 ▶ 21:01
Prediction Not checkable as stated
Advertising and subscriptions hold Gimlet's greatest monetization potential
“I think the advertising business, and then down the road the subscription business has the biggest potential, together.”
Matt Lieber Jan 15, 2016 ▶ 23:10
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