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Mar 22, 2023 · 37m · american-optimist

Ep 50: Troy Carter on Discovering Lady Gaga, Future of Music, and Speaking Out on School Choice · Joe Lonsdale

Troy Carter · 28m spoken Joe Lonsdale · 6m spoken
0:00 / 0:00
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In this episode of American Optimist, host Joe Lonsdale interviews music mogul and tech investor Troy Carter about his journey from West Philadelphia to managing Lady Gaga and investing in Silicon Valley. Carter discusses empowering independent artists through his venture Venice Music, as well as his passionate advocacy for school choice and educational reform.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Joe holds 17.8% of the talking time here. How this is scored →

Joe as informed peer 2.8 Guest teaching 1.5 Guest disagreement 0.5 Joe pushing back 0.0
05100:0010:0020:0030:000:56–5:05 · Joe as informed peer 2/10 Venice Music and Empowering Independent Artists The conversation opens with a warm, biographical tone. Lonsdale asks about the founding vision behind Venice Music and Carter's upbringing in West Philadelphia during the crack epidemic, to which Carter provides thoughtful, reflective context.5:05–9:10 · Joe as informed peer 3/10 Early Hip-Hop Ambitions, Jazzy Jeff, and Bad Boy Entertainment Carter recounts his initial hip-hop aspirations, auditioning for Jazzy Jeff in the snow, and his transition into party promoting and interning for P Diddy. Lonsdale chimes in warmly with personal anecdotes about Wu-Tang Clan wearing Palantir apparel.9:10–12:57 · Joe as informed peer 2/10 Managing Eve, Erving Wonder, and Financial Crisis Carter shares the highs and sudden lows of managing Eve, selling Erving Wonder to a corporate entity, and facing financial devastation around 2007. The exchange is deeply sympathetic, with Lonsdale drawing parallels to tech startup volatility.12:57–18:49 · Joe as informed peer 2/10 Discovering Lady Gaga and Breaking Through Carter explains discovering Lady Gaga when both of their careers were at a low point and navigating the friction of introducing a non-traditional pop act to radio. Lonsdale facilitates the storytelling with supportive prompts.18:49–23:55 · Joe as informed peer 4/10 Transition to Silicon Valley and Early Angel Investing The dialogue shifts to Silicon Valley culture and angel investing, reminiscing about Carter attending Lonsdale's barbecue in 2010. They share mutual respect around spotting talent and early bets like ContextLogic/Wish.23:55–34:06 · Joe as informed peer 4/10 Modernizing Music Industry Infrastructure Carter and Lonsdale discuss music distribution bottlenecks before pivoting into education reform, school choice, and political accountability. Both speakers are in strong ideological agreement about challenging union influence and partisan complacency.0:56–5:05 · Guest teaching 1/10 Venice Music and Empowering Independent Artists The conversation opens with a warm, biographical tone. Lonsdale asks about the founding vision behind Venice Music and Carter's upbringing in West Philadelphia during the crack epidemic, to which Carter provides thoughtful, reflective context.5:05–9:10 · Guest teaching 1/10 Early Hip-Hop Ambitions, Jazzy Jeff, and Bad Boy Entertainment Carter recounts his initial hip-hop aspirations, auditioning for Jazzy Jeff in the snow, and his transition into party promoting and interning for P Diddy. Lonsdale chimes in warmly with personal anecdotes about Wu-Tang Clan wearing Palantir apparel.9:10–12:57 · Guest teaching 1/10 Managing Eve, Erving Wonder, and Financial Crisis Carter shares the highs and sudden lows of managing Eve, selling Erving Wonder to a corporate entity, and facing financial devastation around 2007. The exchange is deeply sympathetic, with Lonsdale drawing parallels to tech startup volatility.12:57–18:49 · Guest teaching 1/10 Discovering Lady Gaga and Breaking Through Carter explains discovering Lady Gaga when both of their careers were at a low point and navigating the friction of introducing a non-traditional pop act to radio. Lonsdale facilitates the storytelling with supportive prompts.18:49–23:55 · Guest teaching 2/10 Transition to Silicon Valley and Early Angel Investing The dialogue shifts to Silicon Valley culture and angel investing, reminiscing about Carter attending Lonsdale's barbecue in 2010. They share mutual respect around spotting talent and early bets like ContextLogic/Wish.23:55–34:06 · Guest teaching 3/10 Modernizing Music Industry Infrastructure Carter and Lonsdale discuss music distribution bottlenecks before pivoting into education reform, school choice, and political accountability. Both speakers are in strong ideological agreement about challenging union influence and partisan complacency.0:56–5:05 · Guest disagreement 0/10 Venice Music and Empowering Independent Artists The conversation opens with a warm, biographical tone. Lonsdale asks about the founding vision behind Venice Music and Carter's upbringing in West Philadelphia during the crack epidemic, to which Carter provides thoughtful, reflective context.5:05–9:10 · Guest disagreement 0/10 Early Hip-Hop Ambitions, Jazzy Jeff, and Bad Boy Entertainment Carter recounts his initial hip-hop aspirations, auditioning for Jazzy Jeff in the snow, and his transition into party promoting and interning for P Diddy. Lonsdale chimes in warmly with personal anecdotes about Wu-Tang Clan wearing Palantir apparel.9:10–12:57 · Guest disagreement 0/10 Managing Eve, Erving Wonder, and Financial Crisis Carter shares the highs and sudden lows of managing Eve, selling Erving Wonder to a corporate entity, and facing financial devastation around 2007. The exchange is deeply sympathetic, with Lonsdale drawing parallels to tech startup volatility.12:57–18:49 · Guest disagreement 0/10 Discovering Lady Gaga and Breaking Through Carter explains discovering Lady Gaga when both of their careers were at a low point and navigating the friction of introducing a non-traditional pop act to radio. Lonsdale facilitates the storytelling with supportive prompts.18:49–23:55 · Guest disagreement 1/10 Transition to Silicon Valley and Early Angel Investing The dialogue shifts to Silicon Valley culture and angel investing, reminiscing about Carter attending Lonsdale's barbecue in 2010. They share mutual respect around spotting talent and early bets like ContextLogic/Wish.23:55–34:06 · Guest disagreement 2/10 Modernizing Music Industry Infrastructure Carter and Lonsdale discuss music distribution bottlenecks before pivoting into education reform, school choice, and political accountability. Both speakers are in strong ideological agreement about challenging union influence and partisan complacency.0:56–5:05 · Joe pushing back 0/10 Venice Music and Empowering Independent Artists The conversation opens with a warm, biographical tone. Lonsdale asks about the founding vision behind Venice Music and Carter's upbringing in West Philadelphia during the crack epidemic, to which Carter provides thoughtful, reflective context.5:05–9:10 · Joe pushing back 0/10 Early Hip-Hop Ambitions, Jazzy Jeff, and Bad Boy Entertainment Carter recounts his initial hip-hop aspirations, auditioning for Jazzy Jeff in the snow, and his transition into party promoting and interning for P Diddy. Lonsdale chimes in warmly with personal anecdotes about Wu-Tang Clan wearing Palantir apparel.9:10–12:57 · Joe pushing back 0/10 Managing Eve, Erving Wonder, and Financial Crisis Carter shares the highs and sudden lows of managing Eve, selling Erving Wonder to a corporate entity, and facing financial devastation around 2007. The exchange is deeply sympathetic, with Lonsdale drawing parallels to tech startup volatility.12:57–18:49 · Joe pushing back 0/10 Discovering Lady Gaga and Breaking Through Carter explains discovering Lady Gaga when both of their careers were at a low point and navigating the friction of introducing a non-traditional pop act to radio. Lonsdale facilitates the storytelling with supportive prompts.18:49–23:55 · Joe pushing back 0/10 Transition to Silicon Valley and Early Angel Investing The dialogue shifts to Silicon Valley culture and angel investing, reminiscing about Carter attending Lonsdale's barbecue in 2010. They share mutual respect around spotting talent and early bets like ContextLogic/Wish.23:55–34:06 · Joe pushing back 0/10 Modernizing Music Industry Infrastructure Carter and Lonsdale discuss music distribution bottlenecks before pivoting into education reform, school choice, and political accountability. Both speakers are in strong ideological agreement about challenging union influence and partisan complacency.

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

0:00 · Joe 30.3% · guest 69.7%0:00 · Joe 30.3% · guest 69.7%3:00 · Joe 11.3% · guest 88.7%3:00 · Joe 11.3% · guest 88.7%6:00 · Joe 20% · guest 80%6:00 · Joe 20% · guest 80%9:00 · Joe 18.9% · guest 81.1%9:00 · Joe 18.9% · guest 81.1%12:00 · Joe 13.8% · guest 86.2%12:00 · Joe 13.8% · guest 86.2%15:00 · Joe 14% · guest 86%15:00 · Joe 14% · guest 86%18:00 · Joe 17.4% · guest 82.6%18:00 · Joe 17.4% · guest 82.6%21:00 · Joe 23% · guest 77%21:00 · Joe 23% · guest 77%24:00 · Joe 19.3% · guest 80.7%24:00 · Joe 19.3% · guest 80.7%27:00 · Joe 17.4% · guest 82.6%27:00 · Joe 17.4% · guest 82.6%30:00 · Joe 6.1% · guest 93.9%30:00 · Joe 6.1% · guest 93.9%33:00 · Joe 25.1% · guest 74.9%33:00 · Joe 25.1% · guest 74.9%36:00 · Joe 10.6% · guest 89.4%36:00 · Joe 10.6% · guest 89.4%
Sharpest disagreement ▶ 29:40 Demanding political accountability on school choice

Carter forcefully calls out Democratic politicians for taking minority votes for granted while blocking charter schools and avoiding reform due to teachers union donations.

 Hardest push from Joe ▶ 19:45 Playful banter on Silicon Valley vs music culture

In a completely non-adversarial episode, Lonsdale playfully remarks on tech cultural humility compared to major label executive perks Carter described.

 Biggest teaching moment ▶ 24:05 Carter explaining record label disintermediation

Carter provides an insider breakdown of how record labels structurally detached themselves from end consumers by relying entirely on third-party platforms like Spotify and Apple.

 Joe holds their own ▶ 22:58 Lonsdale on startup valuation cycles and discipline

Lonsdale demonstrates venture expertise when contextualizing the trajectory of Wish and the macroeconomic shift toward cash flow discipline in the 2020s.
the scores for every segment, with the reasoning behind each
ChapterTopicJoe as informed peerGuest teachingGuest disagreementJoe pushing backWhy
Venice Music and Empowering Independent Artists 2100 The conversation opens with a warm, biographical tone. Lonsdale asks about the founding vision behind Venice Music and Carter's upbringing in West Philadelphia during the crack epidemic, to which Carter provides thoughtful, reflective context.
Early Hip-Hop Ambitions, Jazzy Jeff, and Bad Boy Entertainment 3100 Carter recounts his initial hip-hop aspirations, auditioning for Jazzy Jeff in the snow, and his transition into party promoting and interning for P Diddy. Lonsdale chimes in warmly with personal anecdotes about Wu-Tang Clan wearing Palantir apparel.
Managing Eve, Erving Wonder, and Financial Crisis 2100 Carter shares the highs and sudden lows of managing Eve, selling Erving Wonder to a corporate entity, and facing financial devastation around 2007. The exchange is deeply sympathetic, with Lonsdale drawing parallels to tech startup volatility.
Discovering Lady Gaga and Breaking Through 2100 Carter explains discovering Lady Gaga when both of their careers were at a low point and navigating the friction of introducing a non-traditional pop act to radio. Lonsdale facilitates the storytelling with supportive prompts.
Transition to Silicon Valley and Early Angel Investing 4210 The dialogue shifts to Silicon Valley culture and angel investing, reminiscing about Carter attending Lonsdale's barbecue in 2010. They share mutual respect around spotting talent and early bets like ContextLogic/Wish.
Modernizing Music Industry Infrastructure 4320 Carter and Lonsdale discuss music distribution bottlenecks before pivoting into education reform, school choice, and political accountability. Both speakers are in strong ideological agreement about challenging union influence and partisan complacency.

Statements from this episode (9)

Assertion Not checkable as stated
Carter: Independent artists are music's fastest-growing but most underserved sector
“Independent artists, it's one of the fastest growing sectors in the music industry, but at the same time, it's a very underserved market in terms of technology, in terms of services”
Troy Carter Mar 22, 2023 ▶ 1:27
Assertion Partly supported
Carter: Top managers like Scooter Braun started as party promoters
“Like, Gayo Siri, who manages, like, Madonna Scooter Braun, who manages Bieber, myself, and a few other managers, we were all party promoters.”
Troy Carter Mar 22, 2023 ▶ 7:15
Opinion
Carter: Managing software engineers is identical to managing recording artists
“Dude, me, like working with engineers now, you know, with our new startup, I'm like, You know what? They are so close, it's as close as you can get to managing the artists by the way.”
Troy Carter Mar 22, 2023 ▶ 10:21
Insight
Carter: Talent Picking Is Key in Both Music Management and Early-Stage Investing
“I think my personal superpower is being able to pick people, and you know, because as an artist manager, it's like, I can't sign a million artists, you know, so it's like, if you pick, and because you don't make money right away, so it's like, you got to be go…”
Troy Carter Mar 22, 2023 ▶ 21:23
Disclosure
Carter invested blindly in ContextLogic and missed the Wish pivot
“And you said you were gonna invest, and you said Troy, you should put some money in. And, you know, I honestly, I had no idea what Peter was talking about. Like, I had, you know, a little inkling, but you trusted him so much, and I trusted you so much, I'm lik…”
Troy Carter Mar 22, 2023 ▶ 22:31
Assertion Partly supported
Lonsdale: Wish Rose from a $6M Valuation to $25B
“Because he went up 10,000 X, and then had trouble in China, but anyway, there was some genius there, because you can't go from six million valuation to twenty-five billion without knowing something, right?”
Joe Lonsdale Mar 22, 2023 ▶ 22:59
Assertion Not checkable as stated
Carter: Record labels still lack direct customer relationships due to streaming platforms
“All of the technology that's been introduced to the music industry is still one of the only businesses that doesn't have a direct relationship with its customer. So like, if you're a record label Spotify or Apple music or YouTube, they have the direct relation…”
Troy Carter Mar 22, 2023 ▶ 24:19
Assertion Contradicted
Carter: Philadelphia has not approved a single charter school in eight years
“Philadelphia hasn't approved one charter school in eight years since, since this mayor's been in office.”
Troy Carter Mar 22, 2023 ▶ 33:15
Disclosure
Carter forbids his children from using race as an excuse
“I don't allow my kids to use race as an excuse, and... Yeah, and I, it's not allowed in my house, and like, it's just something I firmly believe in”
Troy Carter Mar 22, 2023 ▶ 35:59
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