Mar 12, 2020 · 52m · my-first-million
Nicotine Gum, Dating Apps for the Elderly & Vested Shares Tax | My First Million Podcast 03-03-2020
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Entrepreneurs Sam Parr and Shaan Puri break down the economic realities of startup equity, evaluate scalable business concepts across virtual events and senior companionship, and analyze multi-billion-dollar marketing funnels and high-growth tech valuations.
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 99.3% of the talking time here. How this is scored →
The hosts as informed peer 6.6 Guest teaching 3.0 Guest disagreement 1.6 The hosts pushing back 2.7
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 38:35 Shaan strongly rejects title and pay prioritization
Shaan forcefully rejects listener pushback about job titles and salary, arguing that taking a seat on a high-growth rocket ship outweighs early compensation.
Hardest push from the hosts ▶ 44:30 Sam challenges the Opendoor $100B thesisSam refuses Shaan's framing of Opendoor as a future $100B giant, citing the limited scale of established real estate platforms like Zillow and Trulia.
Biggest teaching moment ▶ 6:35 Shaan breaks down employee option exercise windowsShaan explains the financial trap of 90-day option exercise windows for startup employees who lack the liquidity to purchase their vested shares upon leaving.
The host holds their own ▶ 27:55 Sam reveals Agora's backend newsletter monetizationSam demonstrates comprehensive industry expertise by laying out the exact customer acquisition economics and backend newsletter funnels that drive Agora's billions.
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 |
|---|---|---|---|---|---|---|
| Podcast Experiments, Editing Cadence, and Self-Consciousness | 3 | 2 | 1 | 1 | The co-hosts engage in casual housekeeping banter regarding audio editing techniques, audience feedback on Instagram, and cutting conversational pauses. | |
| Bernie Sanders Tax Proposal, Paper Wealth, and Startup Equity | 7 | 4 | 2 | 3 | Sam and Shaan analyze startup equity taxation, breaking down 409A valuations, paper illiquidity, 90-day option exercise windows, and optimal employee equity pools. | |
| Digital Conferences and the Launch of Run the World | 6 | 3 | 2 | 4 | Shaan pitches digital event platform Run the World amidst pandemic cancellations, while Sam pushes back on the lack of serendipitous networking in virtual formats. | |
| The Lucrative Business Models Behind Book Clubs and Publishing | 8 | 4 | 1 | 2 | Sam demonstrates deep domain knowledge regarding publishing economics, Book of the Month club financials, romance novel consumption patterns, and IP rights acquisitions. | |
| Agora Financial, Direct-Response Marketing, and The Boron Letters | 9 | 3 | 1 | 2 | Sam breaks down Agora Financial's direct-response funnel mechanics, front-end loss leaders, $2,000 backend newsletter upsells, and Gary Halbert's copywriting rules. | |
| Just Talking and Companionship Platforms for Seniors | 6 | 2 | 1 | 2 | Shaan pitches 'Just Talking' as a companionship marketplace for isolated seniors, and Sam assesses the marketplace cold-start problem and seeding strategy. | |
| Finding the Next $100 Billion Tech Rocket Ships | 7 | 3 | 3 | 5 | Shaan and Sam evaluate which $1-5B tech startups could reach $100B, offering counterarguments against popular picks like Airtable, Carta, and Opendoor. |
Statements from this episode (17)
Parr: The Hustle generated $380,000 in revenue in its first year
“When we started the hustle, I saved up 25,000 dollars to start it. With that 25,000 dollars, I made 60 grand in profit in six weeks, which is pretty good. And the first year in business was roughly 380,000 dollars in revenue.”
Puri: Sanders' tax on vested options would disrupt the startup ecosystem
“This will really screw up the way the startups ecosystem works, but it can also adapt.”
Puri: Startups that stop sending investor updates are usually dying
“If you're one of your companies stop sending their updates for a bit that company is about to die or they're on their way to dying and they go into a shell”
Puri: Standard startup cap tables are too founder-greedy
“I think that the normal way that people give out equity is a little too founder greedy. So I wish I had given more equity to my team.”
Parr predicts SXSW 2020 will be canceled
“I predict South by Southwest, This episode will air in a couple days. I bet you they're gonna cancel.”
Parr: Book of the Month generates $10M–$15M ARR from 100K members
“And so book of the month club now has a 100,000 active paying customers, which means they're in the revenue range of 10 to fifteen million a year in recurring revenue.”
Parr: Wattpad has 400 employees and hundreds of millions in revenue
“Wattpad it's owned by a guy in Canada and they have 400 employees. It's a multiple hundred million dollar a year business.”
Parr: Tim Ferriss made 10x more from podcasting than books
“He told me that he, this is what he did tell me. He has made 10 times more money off the podcast than all of his books combined.”
Parr: Tai Lopez's MentorBox is 'incredibly scammy'
“And there's another company called mentor box that does this and Tai Lopez is one of the owners. So it's incredibly scammy. I mean, like you sign up for like 20 dollars and then it rolls into like a 400 dollar a month thing. It's like fucking stupid.”
Parr: Publishing conglomerate Agora makes an estimated $1.5B to $2B annually
“At this point it, you'll see it. It's the most popular one. No, up higher at this point. They make it's rumored. To be one and a half to two billion dollars a year.”
Parr: Copywriting matters more than visual design 100% of the time
“Copywriting over design, 100% any day.”
Puri: Seniors avoid online dating due to pressure of in-person meetups
“The reality is they don't do a lot of online dating because it's so scary and foreign. And it's not the online part that's scary. It's the expectation that you then need to go meet somebody.”
Puri invested in Tesla at a $5B to $8B valuation
“Like I think I invested in Tesla when it was at about this number five, five to eight billion.”
Puri: Airtable Cannot Reach $100B Without Replacing Excel
“So air table air table, it would have to basically replace Excel in the corporate world for it to do this. Otherwise it will not be a hundred billion dollar company.”
Puri: Autonomous winner will be Tesla or acquired by an incumbent
“If one of them becomes a success, a self, a successful self-driving car company, the market leader will be worth over a hundred billion. It's just more likely. I believe it's more likely to be Tesla or one of the incumbents rather they'll buy one of these comp…”
Puri: Buying FAANG stocks outperformed top VC returns over 10 years
“If you had just brought, bought the fang companies, so Facebook, Amazon, Apple, Google in the 10 years it outperformed all VCs or sorry, It outperformed even this sort of top like expected returns of venture capital. So the public market, if you just bought th…”