Jun 30, 2021 · 55m · my-first-million
A Discussion on Sam & Shaan's Recent Investments | My First Million #195
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of My First Million, Sam Parr and Shaan Puri break down their recent angel investments, startup pitches, and capital allocation frameworks across enterprise SaaS, global fintech, and ambitious moonshot ventures.
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 99.6% of the talking time here. How this is scored →
The hosts as informed peer 6.4 Guest teaching 4.0 Guest disagreement 2.3 The hosts pushing back 3.1
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 46:26 Debate over competing with nation-state scale events
Shaan argues that no capitalist entity competes with the Olympics or World Fairs, challenging Sam's premise that market saturation makes the project impossible.
Hardest push from the hosts ▶ 48:14 Sam dismantling live event venture unit economicsSam forcefully dismisses the commercial viability of a modern World's Fair, invoking the historical unprofitability of the Summit Series mountain project.
Biggest teaching moment ▶ 12:05 Shaan explains Indian micro-investing and UPI infrastructureShaan educates Sam on the regulatory structure around digital gold purchases in India and how government-mandated UPI rails unlocked frictionless recurring payments.
The host holds their own ▶ 38:10 Sam details private secondary transaction mathSam demonstrates strong financial acumen by walking through exact SaaS valuation metrics, ARR churn rates, and liquidity mechanisms for a $28M ARR private company.
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 |
|---|---|---|---|---|---|---|
| Abstract Ops: NetSuite for Early-Stage Startups | 6 | 3 | 2 | 3 | Sam pitches Abstract Ops as a back-office solution for startups, drawing on his personal administrative headaches scaling The Hustle. Shaan evaluates the copywriting and questions whether the product is scalable software or tech-enabled human services. | |
| Jar: The Acorns of India Gold Savings | 7 | 5 | 2 | 2 | Shaan breaks down the macro thesis for Jar, explaining Indian cultural affinity for gold, UPI payment infrastructure rails, and regulatory friction shortcuts. Sam engages with logistical questions regarding cross-border angel investing risks. | |
| RuUMR: Bringing the Auction Model to Real Estate | 6 | 4 | 2 | 3 | Sam introduces RuUMR by comparing it to Bring a Trailer applied to residential real estate auctions. Shaan inspects the live listings in real time, raising tactical questions about seller incentives and adoption hurdles for sight-unseen home purchases. | |
| 1Build: Real-Time Construction Cost Data and Pricing API | 7 | 4 | 1 | 2 | Shaan details 1Build's data moat in construction estimating, drawing an analogy to Climate Corporation standardizing unstructured data into APIs. Sam is highly receptive and probes into replication risks and syndicate participation. | |
| ConvertKit: Profitable SaaS Secondary Market Investment | 7 | 3 | 1 | 1 | Sam shares confidential metrics for ConvertKit's secondary share offering at a 7x ARR multiple. Both hosts strongly agree on the financial health and low-risk profile of the business compared to typical venture bets. | |
| The Audacious Moonshot: Recreating the World's Fair | 6 | 5 | 5 | 7 | Shaan outlines Cameron's proposal to revive the World's Fair with 50 million attendees, praising the audacity of the vision. Sam aggressively pushes back, calling the venture fundamentally flawed and citing the financial struggles of similar event businesses like Summit Series. | |
| Praxis: Investing in the Future of Startup Cities | 6 | 4 | 3 | 4 | Shaan describes his speculative check into Praxis, a startup city concept founded on sovereign land negotiations. Sam expresses cautious interest while questioning whether the leadership team has hard real estate execution capability. |
Statements from this episode (22)
Sam Parr invests $400K into Abstract Ops personally and via Hampton VC
“I ended up investing around 400,000 dollars. And I got a preface that saying that, I do my own money that comes straight out of my checking account. And then I also have this thing called HamptonVC. So HamptonVC.com or is it .com or .co? And you can it's where…”
Parr: Abstract Ops has close to seven figures in recurring revenue
“They have like close to seven figures in recurring revenue, but I think they're still even figuring out the product, which frankly is a reason why you shouldn't have, I shouldn't have invested is like, they're still kind of tinkering exactly what it's going to…”
Shaan Puri: Investing is easier when you are the target customer
“If you can be, if you are the customer, it's way easier to invest than things that you're guessing about.”
Shaan Puri invested $150K into Indian startup Jar at $12M valuation
“So I put in a 150 K
and it's got a twelve million dollar valuation and a 20% discount.”
Puri: Average Jar user saves $300 within two to three months
“And so like their average user after, I think like two or three months has saved 300 dollars already in the app, US dollars.”
Puri: First two Indian startup investments rank among his best deals
“Having said all that, the two Indian investments I've done so far are probably two of my best investments.”
Sam Parr predicts buying homes sight unseen will become normal
“In my mind, I still think that in 10, 20, 30 years, it will be normal actually to buy a house sight unseen, site on scene, even though a lot of people don't think that.”
Puri: Startup portfolios require bets on ideas that sound likely to fail
“You don't want all your bets to be logical, clear, good ideas, because that means your risk profile wasn't right with startup investment. You need a few ideas that, you know, sound like they're going to fail when you invest in them, and then you either, either…”
Puri: 1Build will eventually eliminate cost estimators as a profession
“But I think over time, my sense is that over time, it eliminates the need for cost estimators as a profession.”
Puri: Annual construction material costs exceed twice total e-commerce spending
“You know, the, just the material cost for construction is twice the amount annually of all of e-commerce.
So it's like,
Humongous market.
It's a multi, it's a trillion dollar plus market of just the of just material construction costs.”
Puri: 1Build had seven figures of ARR booked during Series A
“They have seven figures of ARR already booked.
And so I invested in this thing in their series A.”
Shaan Puri invested $100K in 1Build at a $50M-plus valuation
“So it was like at a,
Over fifty million dollars valuation.
so you know, so I put in a hundred K.”
Parr shares ConvertKit metrics: $28M ARR and 7x secondary round
“After surveying former and current teammates who hold stock options, we're putting together a secondary round at seven times ARR. And we're looking to raise 2.5 million in total with two point oh five. So two million already committed. ARR is twenty eight mill…”
Sam Parr allocates 95% to index funds and 5% to angel investing
“The way that I'm doing my net worth is one percentage of the vast majority, let's say, 95% is in index funds. Boring. Five percent is going to be in angel investing.”
Puri thinks ConvertKit could sell for 30% to 40% above $200M
“Today I think ConvertKit could sell for more than two hundred million. I think if he wanted to sell this business today, he could probably sell it for somewhere like 30 to 40% higher than that.”
Puri estimates ClickFunnels generates over $100M in annual revenue
“I think ClickFunnels does over a hundred million a year.”
Parr: Coachella generates $100 million in annual revenue
“Coachella makes a hundred million dollars a year, and they've been around for like third or no, 20 years now, or Lollapalooza, 20 years.”
Parr: A private World's Fair will never reach 50M attendees
“It will never, ever, ever happen at that scale.”
Shaan Puri invested $25,000 in startup city venture Praxis
“I put a very small amount, but 25 K into a which is like below what I would invest in any other startup into a guy trying to build a startup city.”