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Aug 25, 2022 · 1h 11m · startup-ideas

Winning at Startups and the Future of Culture

Sahil Bloom · 28m spoken Tom McLeod · 23m spoken Greg Isenberg · 12m spoken
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Cohosts Sahil Bloom and Greg Isenberg discuss hard-earned startup principles and the power of real-world community building before welcoming serial entrepreneur Tom McLeod to explore founder resilience and his decentralized museum project, Arkive.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 20.5% of the talking time here. How this is scored →

Greg as informed peer 4.4 Guest teaching 1.8 Guest disagreement 0.6 Greg pushing back 1.0
05100:0015:0030:0045:001:00:000:40–3:23 · Greg as informed peer 2/10 Sahil's Viral NYC In-Person Meetup Greg playfully inquires about Sahil's recent illness stemming from his massive New York meetup. The tone is casual and warm as Sahil recaps how Sam Parr created the viral Eventbrite page without warning.3:23–8:12 · Greg as informed peer 3/10 Sponsor Break: AG1 by Athletic Greens Following an ad read, Sahil reflects on the intellectual chemistry of in-person events and community building. Greg adds perspective on consumer burnout with screens driving post-pandemic IRL demand.8:13–30:18 · Greg as informed peer 8/10 Deconstructing Greg's Startup Guide and Life Principles Sahil guides the conversation through Greg's viral startup principles thread. Greg demonstrates substantial entrepreneurial authority, recounting his experiences at WeWork, selling to StumbleUpon, and negotiation advice from Ram Shriram.30:19–39:47 · Greg as informed peer 4/10 Guest Introduction: Tom McLeod on Entrepreneurial Resilience Tom McLeod joins the episode and shares a boxing analogy for founder resilience against rejection. The hosts and guest reminisce about Greg's historical founder community house in Bayview.39:47–1:11:24 · Greg as informed peer 5/10 Sponsor Break: AG1 Mid-Roll Tom breaks down Arkive's model for decentralized physical art curation, while Greg frames the concept through gaming dynamics like Roblox and Fortnite. Tom details the curation phases, provenance tracking, and reward points.0:40–3:23 · Guest teaching 1/10 Sahil's Viral NYC In-Person Meetup Greg playfully inquires about Sahil's recent illness stemming from his massive New York meetup. The tone is casual and warm as Sahil recaps how Sam Parr created the viral Eventbrite page without warning.3:23–8:12 · Guest teaching 1/10 Sponsor Break: AG1 by Athletic Greens Following an ad read, Sahil reflects on the intellectual chemistry of in-person events and community building. Greg adds perspective on consumer burnout with screens driving post-pandemic IRL demand.8:13–30:18 · Guest teaching 1/10 Deconstructing Greg's Startup Guide and Life Principles Sahil guides the conversation through Greg's viral startup principles thread. Greg demonstrates substantial entrepreneurial authority, recounting his experiences at WeWork, selling to StumbleUpon, and negotiation advice from Ram Shriram.30:19–39:47 · Guest teaching 2/10 Guest Introduction: Tom McLeod on Entrepreneurial Resilience Tom McLeod joins the episode and shares a boxing analogy for founder resilience against rejection. The hosts and guest reminisce about Greg's historical founder community house in Bayview.39:47–1:11:24 · Guest teaching 4/10 Sponsor Break: AG1 Mid-Roll Tom breaks down Arkive's model for decentralized physical art curation, while Greg frames the concept through gaming dynamics like Roblox and Fortnite. Tom details the curation phases, provenance tracking, and reward points.0:40–3:23 · Guest disagreement 0/10 Sahil's Viral NYC In-Person Meetup Greg playfully inquires about Sahil's recent illness stemming from his massive New York meetup. The tone is casual and warm as Sahil recaps how Sam Parr created the viral Eventbrite page without warning.3:23–8:12 · Guest disagreement 0/10 Sponsor Break: AG1 by Athletic Greens Following an ad read, Sahil reflects on the intellectual chemistry of in-person events and community building. Greg adds perspective on consumer burnout with screens driving post-pandemic IRL demand.8:13–30:18 · Guest disagreement 1/10 Deconstructing Greg's Startup Guide and Life Principles Sahil guides the conversation through Greg's viral startup principles thread. Greg demonstrates substantial entrepreneurial authority, recounting his experiences at WeWork, selling to StumbleUpon, and negotiation advice from Ram Shriram.30:19–39:47 · Guest disagreement 1/10 Guest Introduction: Tom McLeod on Entrepreneurial Resilience Tom McLeod joins the episode and shares a boxing analogy for founder resilience against rejection. The hosts and guest reminisce about Greg's historical founder community house in Bayview.39:47–1:11:24 · Guest disagreement 1/10 Sponsor Break: AG1 Mid-Roll Tom breaks down Arkive's model for decentralized physical art curation, while Greg frames the concept through gaming dynamics like Roblox and Fortnite. Tom details the curation phases, provenance tracking, and reward points.0:40–3:23 · Greg pushing back 1/10 Sahil's Viral NYC In-Person Meetup Greg playfully inquires about Sahil's recent illness stemming from his massive New York meetup. The tone is casual and warm as Sahil recaps how Sam Parr created the viral Eventbrite page without warning.3:23–8:12 · Greg pushing back 0/10 Sponsor Break: AG1 by Athletic Greens Following an ad read, Sahil reflects on the intellectual chemistry of in-person events and community building. Greg adds perspective on consumer burnout with screens driving post-pandemic IRL demand.8:13–30:18 · Greg pushing back 1/10 Deconstructing Greg's Startup Guide and Life Principles Sahil guides the conversation through Greg's viral startup principles thread. Greg demonstrates substantial entrepreneurial authority, recounting his experiences at WeWork, selling to StumbleUpon, and negotiation advice from Ram Shriram.30:19–39:47 · Greg pushing back 1/10 Guest Introduction: Tom McLeod on Entrepreneurial Resilience Tom McLeod joins the episode and shares a boxing analogy for founder resilience against rejection. The hosts and guest reminisce about Greg's historical founder community house in Bayview.39:47–1:11:24 · Greg pushing back 2/10 Sponsor Break: AG1 Mid-Roll Tom breaks down Arkive's model for decentralized physical art curation, while Greg frames the concept through gaming dynamics like Roblox and Fortnite. Tom details the curation phases, provenance tracking, and reward points.

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

0:00 · Greg 6.8% · guest 93.2%0:00 · Greg 6.8% · guest 93.2%3:00 · Greg 10.1% · guest 89.9%3:00 · Greg 10.1% · guest 89.9%6:00 · Greg 18.5% · guest 81.5%6:00 · Greg 18.5% · guest 81.5%9:00 · Greg 41.5% · guest 58.5%9:00 · Greg 41.5% · guest 58.5%12:00 · Greg 56.9% · guest 43.1%12:00 · Greg 56.9% · guest 43.1%15:00 · Greg 42.5% · guest 57.5%15:00 · Greg 42.5% · guest 57.5%18:00 · Greg 48.1% · guest 51.9%18:00 · Greg 48.1% · guest 51.9%21:00 · Greg 35.2% · guest 64.8%21:00 · Greg 35.2% · guest 64.8%24:00 · Greg 67.4% · guest 32.6%24:00 · Greg 67.4% · guest 32.6%27:00 · Greg 60.3% · guest 39.7%27:00 · Greg 60.3% · guest 39.7%30:00 · Greg 0% · guest 100%30:00 · Greg 0% · guest 100%33:00 · Greg 34.7% · guest 65.3%33:00 · Greg 34.7% · guest 65.3%36:00 · Greg 0% · guest 100%36:00 · Greg 0% · guest 100%39:00 · Greg 0% · guest 100%39:00 · Greg 0% · guest 100%42:00 · Greg 16.7% · guest 83.3%42:00 · Greg 16.7% · guest 83.3%45:00 · Greg 0% · guest 100%45:00 · Greg 0% · guest 100%48:00 · Greg 0% · guest 100%48:00 · Greg 0% · guest 100%51:00 · Greg 0% · guest 100%51:00 · Greg 0% · guest 100%54:00 · Greg 0% · guest 100%54:00 · Greg 0% · guest 100%57:00 · Greg 34.4% · guest 65.6%57:00 · Greg 34.4% · guest 65.6%1:00:00 · Greg 0% · guest 100%1:00:00 · Greg 0% · guest 100%1:03:00 · Greg 4.9% · guest 95.1%1:03:00 · Greg 4.9% · guest 95.1%1:06:00 · Greg 6.6% · guest 93.4%1:06:00 · Greg 6.6% · guest 93.4%1:09:00 · Greg 7.6% · guest 92.4%1:09:00 · Greg 7.6% · guest 92.4%
Sharpest disagreement ▶ 43:58 Tom roleplays the cynical crypto skeptic take

Tom adopts the aggressive persona of Web3 detractors who view crypto museum projects as unnecessary financialization by outsiders.

 Hardest push from Greg ▶ 43:21 Greg challenges Tom to Steelman detractor arguments

Greg pushes Tom to frame both the extreme bear detractor and hyper-bull perspectives on Arkive's viability.

 Biggest teaching moment ▶ 48:32 Tom outlines the imperialist history of traditional museums

Tom educates the hosts on how traditional museum collections frequently represent imperial soft power and why decentralized repatriation matters.

 Greg holds their own ▶ 25:05 Greg reveals lessons learned from StumbleUpon acquisition

Greg demonstrates deep operational and dealmaking expertise by explaining how active listening directly affects startup acquisition valuations.
the scores for every segment, with the reasoning behind each
ChapterTopicGreg as informed peerGuest teachingGuest disagreementGreg pushing backWhy
Sahil's Viral NYC In-Person Meetup 2101 Greg playfully inquires about Sahil's recent illness stemming from his massive New York meetup. The tone is casual and warm as Sahil recaps how Sam Parr created the viral Eventbrite page without warning.
Sponsor Break: AG1 by Athletic Greens 3100 Following an ad read, Sahil reflects on the intellectual chemistry of in-person events and community building. Greg adds perspective on consumer burnout with screens driving post-pandemic IRL demand.
Deconstructing Greg's Startup Guide and Life Principles 8111 Sahil guides the conversation through Greg's viral startup principles thread. Greg demonstrates substantial entrepreneurial authority, recounting his experiences at WeWork, selling to StumbleUpon, and negotiation advice from Ram Shriram.
Guest Introduction: Tom McLeod on Entrepreneurial Resilience 4211 Tom McLeod joins the episode and shares a boxing analogy for founder resilience against rejection. The hosts and guest reminisce about Greg's historical founder community house in Bayview.
Sponsor Break: AG1 Mid-Roll 5412 Tom breaks down Arkive's model for decentralized physical art curation, while Greg frames the concept through gaming dynamics like Roblox and Fortnite. Tom details the curation phases, provenance tracking, and reward points.

Statements from this episode (9)

Assertion Not checkable as stated
Bloom: 1,000 people attended NYC meetup organized via spontaneous tweets
“So in the end we ended up having this event, I think in the, in total, like 1400 people RSVP. Saying they were gonna come to it. These two guys, Andrew and Topps, like, basically volunteered themselves to coordinate the event, found this insane venue in Lower …”
Sahil Bloom Aug 25, 2022 ▶ 2:39
Opinion
Isenberg: IRL products are seeing early-2020 digital boom energy
“The same sort of like energy that we saw, like around digital products in early 2020, you're kind of seeing with IRL type products.”
Greg Isenberg Aug 25, 2022 ▶ 7:37
Prediction Not checkable as stated
McLeod: Mainstream users will ignore Web3 until it offers physical experiences
“I don't think the average person will care at all until it's tied to in person experiences, access, physical objects, things that they can touch, feel, do like involve themselves in, and it provides Actual reasons for being a part of a community or participati…”
Tom McLeod Aug 25, 2022 ▶ 50:26
Disclosure
McLeod: Web3 museum Arkive owns the patent for the ENIAC computer
“We have the patent for the ENIAC computer.”
Tom McLeod Aug 25, 2022 ▶ 53:28
Opinion
McLeod: The traditional art world is opaque and plagued by data miners
“The art world broadly is unbelievably obtuse and opaque. You can vary that people are building very building businesses, simply just trying to data mine. What is going on at any time? These are the values collections, why things are happening in this case, we'…”
Tom McLeod Aug 25, 2022 ▶ 56:17
Opinion
McLeod: Alongside's on-chain crypto index funds are a revolutionary Web3 product
“There's a company called Alongside that's doing like cross network giant index funds. I'm personally just a big index fund person. Like I don't think I'm, I have, I don't have the patience to pick a winner. Like I'm not a day trader, but the idea that you can …”
Tom McLeod Aug 25, 2022 ▶ 1:00:59
Assertion Not checkable as stated
McLeod: Arkive has a 2,000-person waitlist and admits 30 members weekly
“There's a kind of a crazy waiting list. I think we're over 2000 people right now and we're only letting in like 30 a week.”
Tom McLeod Aug 25, 2022 ▶ 1:07:59
Disclosure
McLeod: Arkive plans to launch a membership mint in Q1 2023
“Over the next six months, there'll be about four more cure, like curations on that first collection leading with most likely a mint for a membership in Q one, 20, 23.”
Tom McLeod Aug 25, 2022 ▶ 1:08:36
Opinion
Bloom: Web3 curation can dismantle imperialist gatekeeping of historical artifacts
“Like we can sort of remap that in a lot of ways and like, you know, kind of tear down some of the walls of like you know, colonialism and imperialism that I think have largely informed where some of these works exist.”
Sahil Bloom Aug 25, 2022 ▶ 1:09:45
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