Sep 21, 2020 · 28m · 20vc
20VC: The Chainsmokers on Raising Their First $35M Fund and Entering The World of Venture, Dealing with Vulnerability and Insecurity Today & How Music and Venture Compare; The Similarities and Differences
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
On The 20 Minute VC, host Harry Stebbings interviews Drew Taggart and Alex Pall of The Chainsmokers about launching their $35 million fund, Mantis VC. The duo discusses their transition from music to technology investing, investment criteria, founder empathy, long-term empire building, and navigating mental health.
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 34.7% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 2.1 Guest disagreement 0.9 Harry pushing back 1.5
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 9:51 Drew rejects standard music tech expectations
Drew counters the host's assumption about where music stars invest by stating they are bearish on music tech and prefer broader consumer AI/fintech deals like LoanSnap.
Hardest push from Harry ▶ 13:06 Harry presses on allocation squeezesHarry refuses to accept that celebrity investors bypass deal competition, asking directly if they are still getting squeezed on allocations despite their name recognition.
Biggest teaching moment ▶ 11:00 Alex reframes superficial celebrity value addAlex educates the host on how simple social media promos are red flags, explaining how real value comes from structured LP networks and distribution channels.
Harry holds his own ▶ 10:35 Harry asserts venture market mechanics on CAC and distributionHarry displays domain knowledge by explaining how rising customer acquisition costs make distribution the dominant factor on cap tables.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Introducing The Chainsmokers and Their Launch of Mantis VC | 0 | 0 | 0 | 0 | Segment 1 is a solo host introduction and sponsor ad read block. There is no guest present or host-guest interaction. | |
| Grassroots Growth Hacking and Early Tech Investments | 2 | 3 | 1 | 1 | Drew explains how they growth-hacked their early music career by cold-emailing indie bloggers on Hype Machine. The conversation is friendly and collaborative with light host follow-ups. | |
| Transitioning to Venture Capital and Managing High Stakes | 4 | 2 | 1 | 2 | Alex notes that speaking to top VCs shows everyone contradicts themselves, to which Harry agrees by citing his own observation across 2500 episodes that no one really knows. | |
| Investment Strategy, Fan Base Synergy, and LP Value-Add | 5 | 3 | 1 | 2 | Harry demonstrates venture expertise by analyzing rising customer acquisition costs and the critical role of distribution, which Alex and Drew elaborate on using their LP network. | |
| Navigating Allocation Squeezes and Evaluating Founders | 4 | 2 | 1 | 3 | Harry pushes the guests on whether celebrity status truly protects them from allocation squeezes in competitive rounds, prompting Drew to clarify their co-investing strategy. | |
| Personal Drivers, Empathy in VC, and Complementary Superpowers | 4 | 3 | 1 | 2 | Alex shares a deeply personal story about his father passing away, while Harry contributes mentor wisdom that venture investing is fundamentally about how you make founders feel. | |
| Long-Term Vision for The Chainsmokers Empire | 3 | 2 | 1 | 1 | Harry conducts a quickfire round covering favorite books, managing pre-show nerves, and Alex wanting to shift tech culture outside of San Francisco. | |
| Vulnerability, Mental Health, and Future Aspirations | 3 | 2 | 1 | 1 | Harry models radical openness by discussing his struggle with bulimia, prompting Drew and Alex to candidly share their own experiences with depression and public scrutiny. |
Statements from this episode (14)
The Chainsmokers launch $35M Mantis VC fund with Conway, Cuban, and Raboy
“Now, Mantis is their first thirty-five million dollar venture fund, and so if you haven't guessed it already, I'm thrilled to welcome Alex Poole and Drew Taggart, founders of the Chainsmokers, and now Mantis, with the new vehicle they have backing from some of…”
Alex Pall: Ember was one of The Chainsmokers' first startup investments
“Ember was one of the first companies we actually invested in, if not the first, and they're actually doing terrific”
Alex Pall: None of The Chainsmokers' angel investments have gone to zero
“None of our investments have gone to zero yet, but it's just because we haven't been around long enough.”
Alex Pall: The Chainsmokers secured preferred terms in competitive startup deals
“We were seeing that we were getting preferred terms into deals that were hot that other people couldn't get into.”
Drew Taggart: Making Mantis VC succeed is live-or-die for The Chainsmokers
“This is a new space and there's a lot riding on this and it's very live or die for us to make this work.”
Alex Pall: Contradictory advice from top founders proves no one knows everything
“We've spoken to enough incredibly successful people over the last three months. That, like, everyone begins to contradict themselves. Funny way. You know, in the beginning, you're like, alright, alright, I'm thinking about this the right way, and then, like, t…”
Drew Taggart: Mantis VC is bearish on investing in music tech startups
“We actually are pretty bearish on investing in music tech companies, which I feel like we see probably most of them that are out there as of our profile, but we haven't made an investment in the music space yet.”
Alex Pall: Startups wanting only social media posts are a red flag
“So obviously there's the press element and things like that, but to us, it's a red flag when a company's like, hey, can you just like post us on social media?”
Drew Taggart: Mantis VC will not lead investment rounds
“Due to the size of our fund and the check size that we write, we're not leading rounds. Typically, we're not taking up the lion's share of a lot of these rounds.”
Drew Taggart: Alex Pall relentlessly hassles founders until they explicitly reject him
“Alex's superpower, too, is he's the world's greatest haggler, and he'll just hassle people. Like, if you say you're like, yeah, we're interested in having you in this round, you're not gonna not hear from Alex once or twice a day until you, like, officially pa…”
Alex Pall: Silicon Valley tech workers constantly complain about San Francisco
“I would probably, and this is on behalf of all of our friends we've spoken to in Silicon Valley, I feel like we want to remove them from Silicon Valley and move them somewhere else. Everyone just complains about San Francisco and the culture and everything the…”
Harry Stebbings: Struggling with bulimia has always been a major personal challenge
“A vulnerability that I have, like, super struggle with bulimia, always been a big problem for me.”