Dec 12, 2019 · 16m · how-i-built-this

Live From The HIBT Summit: Troy Carter

Troy Carter · 9m spoken Guy Raz · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Recorded live at the 2019 'How I Built This' Summit, host Guy Raz interviews music manager and venture capitalist Troy Carter about his journey from impoverished beginnings in West Philadelphia to breaking global pop star Lady Gaga and investing in top technology startups through resilience, calculated risk, and intellectual humility.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 35.4% of the talking time here. How this is scored →

Guy as informed peer 4.3 Guest teaching 2.3 Guest disagreement 0.7 Guy pushing back 0.3
05100:0010:001:18–3:23 · Guy as informed peer 5/10 Discovering Lady Gaga and the Early Hustle Guy Raz demonstrates strong background knowledge of Troy's early work with Lady Gaga, including specific details about making costumes by hand. Troy elaborates cooperatively with anecdotes about their early hustle.3:25–5:29 · Guy as informed peer 3/10 Navigating Personal Debt and Touring Realities Raz asks whether Troy worried about gambling immense time and sweat equity while unemployed. Troy reframes the gamble by explaining he had nothing else to lose and had complete conviction it was only a matter of timing.5:30–8:13 · Guy as informed peer 6/10 The Startup Model and Evolution of the Music Business Raz connects Troy's methods to startup business models and cites his experience interviewing Logic and Chris Zarou. Troy expands on the historical economics of the music business, explaining how record labels forced artists into touring and merchandise.8:13–11:19 · Guy as informed peer 4/10 West Philadelphia Roots and Financial PTSD Raz probes Troy's concept of financial PTSD and asks if he fears sudden collapse. Troy playfully calls out Raz's polite euphemism of 'financial insecurity,' giving a raw account of carrying kerosene heaters in West Philadelphia.11:19–15:06 · Guy as informed peer 5/10 Risk Tolerance and Mentorship from Will Smith Raz recites Troy's venture capital investments and asks about his risk profile and founder evaluation criteria. Troy reflects on lessons from Will Smith and illustrates his philosophy with a story about a resilient Detroit founder.15:06–16:02 · Guy as informed peer 3/10 The Value of Humility and Continuous Learning Raz asks Troy about the role of intellectual humility in his transition to investing. Troy warmly affirms that asking questions and remaining curious is his primary driving force.1:18–3:23 · Guest teaching 1/10 Discovering Lady Gaga and the Early Hustle Guy Raz demonstrates strong background knowledge of Troy's early work with Lady Gaga, including specific details about making costumes by hand. Troy elaborates cooperatively with anecdotes about their early hustle.3:25–5:29 · Guest teaching 1/10 Navigating Personal Debt and Touring Realities Raz asks whether Troy worried about gambling immense time and sweat equity while unemployed. Troy reframes the gamble by explaining he had nothing else to lose and had complete conviction it was only a matter of timing.5:30–8:13 · Guest teaching 4/10 The Startup Model and Evolution of the Music Business Raz connects Troy's methods to startup business models and cites his experience interviewing Logic and Chris Zarou. Troy expands on the historical economics of the music business, explaining how record labels forced artists into touring and merchandise.8:13–11:19 · Guest teaching 5/10 West Philadelphia Roots and Financial PTSD Raz probes Troy's concept of financial PTSD and asks if he fears sudden collapse. Troy playfully calls out Raz's polite euphemism of 'financial insecurity,' giving a raw account of carrying kerosene heaters in West Philadelphia.11:19–15:06 · Guest teaching 2/10 Risk Tolerance and Mentorship from Will Smith Raz recites Troy's venture capital investments and asks about his risk profile and founder evaluation criteria. Troy reflects on lessons from Will Smith and illustrates his philosophy with a story about a resilient Detroit founder.15:06–16:02 · Guest teaching 1/10 The Value of Humility and Continuous Learning Raz asks Troy about the role of intellectual humility in his transition to investing. Troy warmly affirms that asking questions and remaining curious is his primary driving force.1:18–3:23 · Guest disagreement 0/10 Discovering Lady Gaga and the Early Hustle Guy Raz demonstrates strong background knowledge of Troy's early work with Lady Gaga, including specific details about making costumes by hand. Troy elaborates cooperatively with anecdotes about their early hustle.3:25–5:29 · Guest disagreement 1/10 Navigating Personal Debt and Touring Realities Raz asks whether Troy worried about gambling immense time and sweat equity while unemployed. Troy reframes the gamble by explaining he had nothing else to lose and had complete conviction it was only a matter of timing.5:30–8:13 · Guest disagreement 1/10 The Startup Model and Evolution of the Music Business Raz connects Troy's methods to startup business models and cites his experience interviewing Logic and Chris Zarou. Troy expands on the historical economics of the music business, explaining how record labels forced artists into touring and merchandise.8:13–11:19 · Guest disagreement 2/10 West Philadelphia Roots and Financial PTSD Raz probes Troy's concept of financial PTSD and asks if he fears sudden collapse. Troy playfully calls out Raz's polite euphemism of 'financial insecurity,' giving a raw account of carrying kerosene heaters in West Philadelphia.11:19–15:06 · Guest disagreement 0/10 Risk Tolerance and Mentorship from Will Smith Raz recites Troy's venture capital investments and asks about his risk profile and founder evaluation criteria. Troy reflects on lessons from Will Smith and illustrates his philosophy with a story about a resilient Detroit founder.15:06–16:02 · Guest disagreement 0/10 The Value of Humility and Continuous Learning Raz asks Troy about the role of intellectual humility in his transition to investing. Troy warmly affirms that asking questions and remaining curious is his primary driving force.1:18–3:23 · Guy pushing back 0/10 Discovering Lady Gaga and the Early Hustle Guy Raz demonstrates strong background knowledge of Troy's early work with Lady Gaga, including specific details about making costumes by hand. Troy elaborates cooperatively with anecdotes about their early hustle.3:25–5:29 · Guy pushing back 1/10 Navigating Personal Debt and Touring Realities Raz asks whether Troy worried about gambling immense time and sweat equity while unemployed. Troy reframes the gamble by explaining he had nothing else to lose and had complete conviction it was only a matter of timing.5:30–8:13 · Guy pushing back 0/10 The Startup Model and Evolution of the Music Business Raz connects Troy's methods to startup business models and cites his experience interviewing Logic and Chris Zarou. Troy expands on the historical economics of the music business, explaining how record labels forced artists into touring and merchandise.8:13–11:19 · Guy pushing back 1/10 West Philadelphia Roots and Financial PTSD Raz probes Troy's concept of financial PTSD and asks if he fears sudden collapse. Troy playfully calls out Raz's polite euphemism of 'financial insecurity,' giving a raw account of carrying kerosene heaters in West Philadelphia.11:19–15:06 · Guy pushing back 0/10 Risk Tolerance and Mentorship from Will Smith Raz recites Troy's venture capital investments and asks about his risk profile and founder evaluation criteria. Troy reflects on lessons from Will Smith and illustrates his philosophy with a story about a resilient Detroit founder.15:06–16:02 · Guy pushing back 0/10 The Value of Humility and Continuous Learning Raz asks Troy about the role of intellectual humility in his transition to investing. Troy warmly affirms that asking questions and remaining curious is his primary driving force.

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

0:00 · Guy 62.2% · guest 37.8%0:00 · Guy 62.2% · guest 37.8%3:00 · Guy 33.5% · guest 66.5%3:00 · Guy 33.5% · guest 66.5%6:00 · Guy 45.1% · guest 54.9%6:00 · Guy 45.1% · guest 54.9%9:00 · Guy 3.7% · guest 96.3%9:00 · Guy 3.7% · guest 96.3%12:00 · Guy 19.8% · guest 80.2%12:00 · Guy 19.8% · guest 80.2%15:00 · Guy 62.4% · guest 37.6%15:00 · Guy 62.4% · guest 37.6%
Sharpest disagreement ▶ 9:09 Teasing Raz over euphemistic framing of poverty

Troy good-naturedly pushes back on Raz describing his childhood as 'financial insecurity,' correcting him bluntly that his family was completely broke and struggling for basic utilities.

Hardest push from Guy ▶ 4:37 Challenging the risk of working without income

Raz presses Troy on the severe personal risk and anxiety of investing unpaid sweat equity into an unproven artist while personal debts piled up.

Biggest teaching moment ▶ 7:23 Explaining the structural reality of artist revenue

Troy educates Raz on the long history of music revenue, explaining that touring and merchandise were never new side businesses but necessary survival mechanisms because record deals traditionally exploited artists.

Guy holds their own ▶ 5:30 Framing artist management through the startup lens

Raz demonstrates deep domain synthesis by comparing Troy's early career with Gaga to the methodical audience-building startup playbook used by Chris Zarou and Logic.

the scores for every segment, with the reasoning behind each
ChapterTopicGuy as informed peerGuest teachingGuest disagreementGuy pushing backWhy
Discovering Lady Gaga and the Early Hustle 5100 Guy Raz demonstrates strong background knowledge of Troy's early work with Lady Gaga, including specific details about making costumes by hand. Troy elaborates cooperatively with anecdotes about their early hustle.
Navigating Personal Debt and Touring Realities 3111 Raz asks whether Troy worried about gambling immense time and sweat equity while unemployed. Troy reframes the gamble by explaining he had nothing else to lose and had complete conviction it was only a matter of timing.
The Startup Model and Evolution of the Music Business 6410 Raz connects Troy's methods to startup business models and cites his experience interviewing Logic and Chris Zarou. Troy expands on the historical economics of the music business, explaining how record labels forced artists into touring and merchandise.
West Philadelphia Roots and Financial PTSD 4521 Raz probes Troy's concept of financial PTSD and asks if he fears sudden collapse. Troy playfully calls out Raz's polite euphemism of 'financial insecurity,' giving a raw account of carrying kerosene heaters in West Philadelphia.
Risk Tolerance and Mentorship from Will Smith 5200 Raz recites Troy's venture capital investments and asks about his risk profile and founder evaluation criteria. Troy reflects on lessons from Will Smith and illustrates his philosophy with a story about a resilient Detroit founder.
The Value of Humility and Continuous Learning 3100 Raz asks Troy about the role of intellectual humility in his transition to investing. Troy warmly affirms that asking questions and remaining curious is his primary driving force.

Statements from this episode (6)

Assertion Not checkable as stated
Carter: Industry told early Lady Gaga she needed a nose job
“I remember people telling her she was gonna have to get a nose job, you know, because, you know, her nose was too big to be a pop star, or she was gonna have to give these songs to the Pussycat Dolls because she wasn't famous enough. Or this record needed to g…”
Troy Carter Dec 12, 2019 ▶ 2:27
Opinion
Carter: Record labels have 'screwed over artists for generations'
“Record income traditionally has been your smallest piece of the pie because record labels have screwed over artists for generations. So you're always forced to go on the road and sell merchandise and do all of these other things to subsidize the income essenti…”
Troy Carter Dec 12, 2019 ▶ 7:23
Insight
Carter: Independent artists get better label terms by building audiences first
“We're starting to see a generation of independent artists now that have broken that barrier that are starting to make money off of music as well, because they're putting out this music. The record labels are discovering them because they've already blown up es…”
Troy Carter Dec 12, 2019 ▶ 7:46
Insight
Carter: Childhood poverty fundamentally changes an entrepreneur's relationship to risk
“I'll talk to some of my friends who, you know, are successful entrepreneurs or business owners and, But grew up, you know, middle class or whatever, right? So, it's a different set of worries when it comes to running a business, or being an entrepreneur, or ev…”
Troy Carter Dec 12, 2019 ▶ 9:00
Insight
Carter: Will Smith relied on his conservative manager to mitigate extreme risks
“Will had this thing where his manager, JL, is the most stable person I know, like just very, very conservative, so, and those two have been together for over thirty-something years, so Will had this thing where Will would jump out the window, and JL's figuring…”
Troy Carter Dec 12, 2019 ▶ 11:57
Assertion Not checkable as stated
Carter: Most founders in our portfolio lack prior industry experience
“Most of the entrepreneurs that we've invested in haven't done anything in that space that they're getting ready to go into.”
Troy Carter Dec 12, 2019 ▶ 13:10
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