Apr 25, 2023 · 57m · my-first-million
How To Write Off $1,000,000 In Taxes (#447)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Shaan Puri and Sam Parr break down film tax write-off strategies, analyze the business models of Tiny and Harvard University, debrief controversial podcast interviews, and discuss viral app concepts alongside digital estate planning.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 99.5% of the talking time here. How this is scored →
The hosts as informed peer 5.6 Guest teaching 1.0 Guest disagreement 0.2 The hosts pushing back 1.8
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 13:00 Shaan attacks hyper-meticulous productivity culture
Shaan forcefully rejects the praise given to hyper-particular planning and productivity lifestyle figures, calling extreme perfectionism spoiled and snobbish.
Hardest push from the hosts ▶ 7:23 Sam calls Hollywood film depreciation strategy a racketSam pushes back against Shaan's glowing review of the tax loophole, arguing that branding it as standard Hollywood practice does not make it any less of a racket.
Biggest teaching moment ▶ 15:14 Shaan acknowledges valid journalistic shortcomings on Shkreli interviewShaan provides clear, candid analysis of why listeners were justified in being frustrated when hosts lacked domain expertise to challenge misleading healthcare claims.
The host holds their own ▶ 20:50 Sam details Tiny's financial mechanics from public filingsSam demonstrates strong analytical preparation by quoting specific revenue numbers, 40% net margins, and dividend distributions directly from Tiny's 300-page prospectus.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Film Production Tax Credits and Depreciation Strategies | 6 | 1 | 0 | 3 | Shaan outlines the mechanics of Section 26 film production tax depreciation and state film subsidies. Sam skeptically questions the scheme, calling it a racket and asking whether the underlying movies actually need to turn a profit. | |
| Debriefing Ramit Sethi and Addressing Martin Shkreli Criticism | 4 | 1 | 1 | 2 | The hosts debrief Sam's interview with Ramit Sethi and address listener backlash from hosting Martin Shkreli. Shaan concedes that legitimate criticism exists regarding their lack of domain expertise to challenge Shkreli's healthcare claims. | |
| Deconstructing Tiny's Public Listing and Andrew Wilkinson's Playbook | 7 | 1 | 0 | 1 | Sam shares findings from reading Tiny's 300-page public listing filing, detailing revenues, margins, and capital extraction. Shaan contributes additional context regarding their platform rollup strategy and early seed funding. | |
| HubSpot CRM Platform Advertisement | 7 | 1 | 0 | 1 | Shaan breaks down Harvard University's $5.8B revenue model across endowment gains, executive education, and publishing. Sam supplements with data regarding Harvard Business School's case study sales volume. | |
| The 'My Nine' App Concept and Post-Death Digital Asset Wills | 4 | 1 | 0 | 2 | Shaan pitches a viral social app concept based on top friend lists, which Sam immediately hijacks and repurposes into a digital estate planning and probate notification tool for angel investments and crypto. |
Statements from this episode (13)
Puri: Obama-era tax rules allow a 100% upfront write-off on film budgets
“So what Obama did was he changed the rules, I believe during his time. To say, you can write off a hundred percent of a film's cost before they even make the film, before the money's spent on that film, just on the budget.”
Puri: States like Georgia and Alabama offer up to 30% in film tax credits
“Georgia, Alabama, basically a bunch of states come and they say, Hey, if you got a million dollar movie,
We'll give you 30% of the films we'll give you 30, up to 30% in tax credits.”
Puri: Film investors must qualify as active to offset active income
“Just like with real estate, you got to be an active investor. So you have to be an active film investor in order to offset against your active income.”
Shaan Puri says Martin Shkreli is intelligent and worth learning from
“I think it's hard to deny that the guy's very intelligent and has a lot of interesting things to say. And I, you know, frankly, you can learn a lot from somebody who's highly intelligent, has interesting things to say.”
Parr: MetaLab generated $62.8M with 40-45% margins in 2021
“In 2021, it did 62.8 million dollars. And that's interesting because it actually has been growing not crazy fast. So it's been growing something like 23% a year. Or for the last handful of years, we can only see a couple years here, but it does a 45% or 40% ma…”
Parr: Tiny sold Mealtime for $25M with $13M profit
“Additionally, they had a company called Mealtime, which is like a meal prepping software that he sold for twenty-five million dollars, so he had a, and they gained, they profited thirteen million dollars off that.”
Puri: MetaLab and Dribbble generate the bulk of Tiny's revenue and EBITDA
“Okay, so you, if you look at where the bulk of the revenue and EBITDA comes from, it's two companies. So yes, he's got a portfolio of 30 companies, but it's MetaLab and it's Dribbble that are carrying the thing on its back.”
Shaan Puri: Holding company deal cadence is painfully slow for founders
“Having said that is probably the type of business where You make one good decision, one good deal a year or two good deals a year. And that was a great year. And that I think that speed is just very hard for most entrepreneurial people to go at.”
Puri: 80% of Harvard's 2021 revenue came from non-education sources
“Last year 5.8 billion in total revenue. Two billion of that comes from the profits of their endowment. Hell of a year for them. I actually, this wasn't last year. This was, I think, 20, 21. So two years ago. So 5.8 billion in total revenue, two billion from th…”
Puri: Harvard generates more annual revenue than Twitter and Snapchat
“The school earns more revenue than both Twitter and Snapchat. Twitter's at five billion, Snapchat's 4.6 billion. Harvard has more revenue than both of them.”
Puri: Harvard's endowment lost only 1.8% in 2022
“And in 20, 22, when my portfolio was down like 45%, they lost 1.8%. Well, they're doing it right, right? Goddamn Harvard geniuses. Somehow lost only less than two percent when the whole market has been terrible this year.”
Shaan Puri breaks down Harvard's exact endowment asset allocation
“Three percent cash. Okay. 32% into hedge funds. Which headphones, does it say? It doesn't say which ones, no. 44% into private equity plus venture capital, but most of it's private equity. So what do they buy? So that's the bulk of it. And then there's six per…”