Dec 17, 2021 · 1h 0m · startup-ideas
How to Become a Super Ball with Anthony Scaramucci | Where It Happens
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In this episode of Where It Happens, hosts Sahil Bloom and Greg Isenberg sit down with financier Anthony Scaramucci to discuss navigating viral social media backlash, executing large-scale events, and cultivating a resilient 'super ball' mindset in business and life.
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 17.4% of the talking time here. How this is scored →
Greg as informed peer 3.5 Guest teaching 4.0 Guest disagreement 2.1 Greg pushing back 1.2
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 44:18 Scaramucci rejects the premise that the younger generation is softer
Scaramucci firmly rejects Greg's question about youth being softer, explaining from his military support experience that they are tough but hindered by self-consciousness and posturing.
Hardest push from Greg ▶ 23:05 Greg pushes back on the traditional mega-scale launch approachGreg challenges the conventional capital-intensive model of event building by arguing that modern ventures must start with an MVP and covert digital community validation.
Biggest teaching moment ▶ 36:25 Scaramucci breaks down crypto de-layering against institutional skepticsScaramucci educates the room on how blockchain removes legacy financial intermediaries, citing how even skeptical titans like Dalio and Tudor Jones eventually buy in once they understand the tech.
Greg holds their own ▶ 19:01 Greg details lean tactical execution for physical eventsGreg demonstrates sharp startup product expertise by outlining a concrete tactical strategy to validate demand on Discord and no-code tools before pitching municipal governments.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Sahil Bloom's Viral Airport Meme Experience | 4 | 1 | 1 | 1 | Greg and Sahil engage in casual, friendly banter reviewing Sahil's viral TSA airport encounter and how he leaned into becoming a meme. | |
| Sponsor Spotlight: Four Sigmatic | 0 | 0 | 0 | 0 | Segment is a dual-sponsor ad break for Four Sigmatic and Eight Sleep with rehearsed dialogue. | |
| Greg Isenberg's Web3 Tweet and Online Trolling | 5 | 1 | 1 | 1 | Greg relates his own experience getting dunked on for an NFT tweet while Sahil agrees on the necessity of standing behind public beliefs. | |
| Pitching the Revival of the World's Fair | 6 | 2 | 2 | 2 | Greg and Sahil debate the feasibility of an ambitious World's Fair reboot pitch, with Greg proposing digital-first validation over heavy capital expenditure. | |
| Anthony Scaramucci on Event Building and Collaboration | 3 | 6 | 3 | 1 | Scaramucci enters and breaks down the immense logistical complexity of large-scale exhibitions, citing his playbook from launching the SALT conference in 2009. | |
| The Future of In-Person Conferences Post-Pandemic | 3 | 5 | 1 | 1 | Scaramucci explains why in-person conferences will surge post-pandemic, pointing to the primal need for physical contact over endless screen time. | |
| Crypto Adoption, Generational Mindsets, and Risk Taking | 4 | 7 | 3 | 1 | Scaramucci delivers an extended breakdown on crypto, challenging Charlie Munger's skepticism and urging the hosts' generation to embrace risk and be resilient super balls. | |
| Blue-Collar Lessons, Career Rejections, and Embracing Failure | 3 | 7 | 3 | 1 | Scaramucci shares blue-collar wisdom from his father and recounts how getting fired by Goldman Sachs and lampooned on SNL forged his comfort with failure. | |
| Generational Resilience, Authenticity, and Equal Opportunity | 3 | 6 | 4 | 2 | When Greg asks if the younger generation is softer, Scaramucci pushes back, redefining their flaw as self-consciousness rather than a lack of toughness. | |
| Scaramucci's Goldman Sachs Interview and Wardrobe Banter | 3 | 5 | 4 | 2 | Scaramucci tells a self-deprecating story about wearing flammable polyester to his Goldman interview, then humorously roasts the hosts for their casual Silicon Valley attire and hair styling. | |
| The Art of Karma Banking and Celebrating Friends | 3 | 6 | 2 | 1 | Scaramucci wraps up his life advice around nonlinear reciprocity, karma banking, and unreservedly celebrating friends' successes. | |
| Post-Interview Reflections on Resilience and Community | 5 | 2 | 1 | 1 | Greg and Sahil summarize their key takeaways from Scaramucci's interview, emphasizing resilience, bounce-back ability, and building collaborative communities. |
Statements from this episode (13)
Bloom: Creators Must Lean into Backlash Because the Internet Is Permanent
“The internet is just
Permanent, man. You can't, like, run and hide from stuff the way you might have used to be able to, where you can just say,
oh yeah, I'm just gonna delete it, walk away, whatever, and so I leaned into it.”
Bloom: Fyre Festival was a great concept despite failed execution
“Fyre Festival was a great idea. I would give him credit for it. He's a, like, fraudster and, you know, did a lot of things that are really bad, but the idea of it, if he had executed, it would have been dope.”
Isenberg: Event businesses should validate demand digital-first before physical buildout
“I wouldn't raise a lot of money. And like go and build a bunch of events from the get-go. I would think about how can I build it, like how can I do community first, internet first, validate the demand, and then build events.”
Bloom: The World's Fair revival will scale down to survive
“My prediction would be it gets boiled down to something more manageable and doable. And that, like, I think his ambition and his energy is amazing, and I never like to bet against people that have good energy. So, I would guess he ends up getting something spu…”
Sahil Bloom argues large-scale event companies are not venture-backable
“It's not a venture bet. Like, I just, I don't understand it as a venture investment, though.”
Bloom: Dubai World Expo is projected to generate $20B in revenue
“Dubai World Expo is supposed to generate, I saw some projection this morning when I was looking this up, like, twenty billion dollars for the Dubai government.”
Scaramucci: 2009 TARP scrutiny forced major banks to cancel Vegas conferences
“Every major investment bank was leaving Las Vegas because of the TARP money. And so what was that? The government gave all the banks money to help defend their balance sheets during the crisis. And so they all felt compelled to cancel any highfalutin conferenc…”
Scaramucci: In-person conferences will return bigger and better post-pandemic
“So I actually think the conferences are going to be bigger, And weirdly better, because it's like a concentrated dose of human personal contact.”
Scaramucci: Ray Dalio and Paul Tudor Jones flipped to buying Bitcoin
“Anybody that studies the blockchain, studies Bitcoin, cryptocurrencies, a guy like Ray Dalio, a brilliant guy, a Bitcoin skeptic, studies it, he buys Bitcoin. Paul Tudor Jones, a skeptic, studies it, buys Bitcoin.”
Bloom: Web3 drives a massive generational wealth transfer that incumbents oppose
“I mean, there's a massive generational transfer of wealth that's happening right now, and the incumbents don't like it. Insiders don't love the fact that anybody can get onto these on rails and operate in this system, but it's such a cool thing.”
Scaramucci: Being truly self-made is impossible in modern society
“You never do it on your own. You need mentors, and professors, and you need, ah, parents, and you need siblings. When somebody tells me they're self-made and I did it all on my own, I'm like, okay, not possible. Not in our society, right?”