3 weird businesses doing $10M, $20M, $30M

3 weird businesses doing $10M, $20M, $30M

Autopilot lets retail investors copy Nancy Pelosi's stock trades — she's up 240% in 3 years vs the S&P's 30-40% — and the app now manages $1.8 billion.

Jun 30, 2026 1:10:39 Difficulty: Beginner Played

TL;DR

Three founders crash the My First Million studio to share their unconventional businesses: Alex Daniels runs Haven Lifestyles, a 40-market real estate magazine doing $10M revenue and $2.5M profit; Josh Weissenstein has acquired 16 family campgrounds through Team Outsider, generating $20M revenue on $60M raised; and Brian runs Autopilot, a copy-trading platform tracking politicians and hedge funds that manages $1.8B in assets and earns $30M in real ARR. The single most actionable takeaway: getting from $0 to $1M is the hardest part — from $1M to $30M was "a piece of cake."

#direct mail advertising #real estate magazines #campground acquisition #copy trading app #congressional stock disclosures #fintech marketplace #AI sales automation #hospitality culture #SBA loan real estate #two-sided marketplace #hiring frameworks #abundance mindset #guerrilla marketing #franchise campgrounds #retail investor tools #real estate magazine #direct mail #copy trading #Nancy Pelosi stocks #fintech #autopilot #Haven Lifestyles #Team Outsider #SBA loan #junk mail #hospitality business #AI automation #Lindy AI #weird businesses #entrepreneurship #Hampton community #hedge funds #politicians trading

Sam Parr and Shaan Puri host three Hampton founders in person in New York: Alex Daniels (Haven Lifestyles, $10M real estate magazines), Josh Weissenstein (Team Outsider, $20M campground acquisitions), and Brian (Autopilot, $30M copy-trading fintech managing $1.8B). Each founder explains their unconventional business, fields questions on scaling and adjacent opportunities, and gets advice on their burning question.

Chapter list
  • The episode opens with rapid-fire teaser clips from each of the three guests — revenues of $10M, $20M, and $30M — before cutting to Shaan and Sam catching up in person, riffing about New York bodegas as the purest expression of entrepreneurship ('We sell cereal now, right?'). Sam explains the premise: he Slacked the Hampton channel asking for founders in New York with genuinely weird businesses, specifically because MFM's audience loves discovering that there are countless unconventional paths to building something big. The format is set — each guest will lead with a number, explain what they do, field questions about adjacent opportunities, and share their burning question for the hosts.

  • The hosts immediately want to infect Alex with their 'sickness' for scale — why isn't this $100M yet? Alex pushes back gently: his real goal is to double profit (to $5M) within 11 months, not necessarily grow top line. Shaan introduces a tiering framework for customer relationships — Tier 1 (texting buddies who'd do you a favor), Tier 2 (email acquaintances), Tier 3 (transactional) — and challenges Alex to call his top 100 agents to understand the retention gap. The adjacent opportunity they're most excited about is home services, building informational content (like winter home prep tips) that pulls in service provider advertisers, similar to what neighborhood publication franchise Stroll has done at $100M+ in revenue. But the biggest surprise is Alex's AI setup: he uses Lindy to handle all inbound sales emails, follow-ups, and upsells autonomously, with human salespeople redeployed to customer experience — an implementation praised by the founder of Lindy himself as the most impressive he had seen.

  • Shaan asks why anyone would choose campgrounds over other real estate categories, and Josh rattles off the structural advantages: strong cash yields, very attractive depreciation on roads and infrastructure (similar to manufactured housing), limited land/building value making them tax-efficient, and operational complexity that keeps unsophisticated buyers away. He explains that two major manufactured-housing REITs have significant campground exposure, which gave the team early validation for the asset class. The biggest culture decision came early: after initially planning to outsource property management, Cody moved in on-site for a full year learning every detail, leading to the conclusion that culture cannot be outsourced and no competent third-party operators existed who could scale with them. The resulting in-house operating company is now 350 people strong. Josh closes with memorable anecdotes — a nine-bank robber quietly employed at one site, and team members selling fallen trees for cash on Facebook — that illustrate the colorful realities of managing dispersed hourly workforces.

  • After the three guests depart, Shaan gets reflective. He traces a personal evolution: a decade before MFM, success felt like a needle in a haystack — one brilliant idea to find, one narrow path to walk. The podcast, San Francisco, and meeting people like today's founders shifted that to pure abundance: tens of thousands of ways to win, and the real question is just which fits you. Sam and Shaan riff on what they'd borrow from each guest — Alex's enviable emotional stability and calm contentment, Brian's audacity and marketing creativity, Josh's outdoorsy lifestyle appeal. Sam pushes back on the idea that small and big businesses are fundamentally different: 'I am equally impressed by a billion-dollar company versus a $5M company.' They close by quoting Jesse Itzler — 'root for everybody, because when you root for everybody, you can never lose' — and Sam teases tomorrow's Ray Dalio interview as an extension of the same lesson in a very different key.

NOI (Net Operating Income)
Revenue minus operating expenses, before debt service and taxes — the standard profitability metric in real estate used to value income-producing properties.
EDDM (Every Door Direct Mail)
A USPS program allowing businesses to mail marketing materials to every address on selected postal routes without needing individual addresses; Alex's Haven Lifestyles uses this model.
SBA Loan
A small business loan partially guaranteed by the U.S. Small Business Administration, allowing buyers to finance acquisitions with lower down payments — Team Outsider used one covering 80%+ of their first campground purchase.
13F Filing
A quarterly SEC disclosure required of investment managers with over $100M in assets, listing their U.S. equity holdings — Autopilot uses these to track hedge fund positions, with a 45-day lag.
Promote
In private equity real estate, the sponsor's disproportionate share of profits above a preferred return threshold — Josh Weissenstein's primary compensation mechanism at Team Outsider.
REIT (Real Estate Investment Trust)
A company that owns income-producing real estate and trades like a stock, required to distribute most profits as dividends; two large REITs hold significant manufactured housing and campground assets.
Copy trading
Automatically mirroring another investor's trades in your own brokerage account in real time — the core mechanic of Autopilot's platform.
ARR (Annual Recurring Revenue)
The annualized value of subscription contracts; Autopilot distinguishes between GMV-based revenue ($30M) and true ARR ($22M) to show the quality of its income.
GMV (Gross Merchandise Value)
Total transaction volume processed through a platform, which can be much larger than actual revenue; used in fintech to show platform scale separate from fees earned.
Series B
A later-stage venture capital funding round, typically for companies with proven revenue looking to scale significantly; Autopilot is preparing to raise one at a $300-400M valuation.
13F lag
The 45-day reporting delay between when a hedge fund makes a trade and when it appears in their SEC-mandated 13F filing, creating a tracking delay for platforms like Autopilot.
Pilot
Autopilot's term for a verified portfolio manager on its platform — a person whose trades followers can automatically copy for a subscription fee.
BlackRock Aladdin
BlackRock's portfolio management software used by institutions to access and manage diverse investment portfolios — Brian from Autopilot cites it as the institutional equivalent of what Autopilot is building for retail investors.
Opco
Short for 'operating company' — the entity that actually runs day-to-day operations, as distinct from a holding company; Team Outsider built an internal opco to manage its campgrounds.
Preferred return
In private equity, the minimum return investors must receive before the sponsor earns any profit share (promote); a standard structure in real estate fund deals.
Accredited investor
An individual or entity meeting SEC wealth/income thresholds (e.g., $1M net worth or $200K+ income) who is legally permitted to invest in unregistered securities offerings.
Situational Awareness
A white paper and hedge fund name by Leopold Aschenbrenner, a former OpenAI researcher, laying out bold predictions about AI's trajectory and its geopolitical implications — referenced as an investor manifesto.
Fragmentation
In market analysis, a high degree of fragmentation means no single player dominates — the campground and local real estate publishing markets are both highly fragmented, creating acquisition opportunities.
DTCC
Depository Trust & Clearing Corporation — the US financial market infrastructure that clears and settles securities transactions; referenced in the context of the capital requirements that nearly sank Robinhood during GameStop.
Lindy
An AI automation platform that can manage email workflows, sales processes, and follow-ups autonomously — used by Haven Lifestyles to run its entire inbound sales cycle without human salespeople.

Chapter 1 · 00:00

Intro

The episode opens with rapid-fire teaser clips from each of the three guests — revenues of $10M, $20M, and $30M — before cutting to Shaan and Sam catching up in person, riffing about New York bodegas as the purest expression of entrepreneurship ('We sell cereal now, right?'). Sam explains the premise: he Slacked the Hampton channel asking for founders in New York with genuinely weird businesses, specifically because MFM's audience loves discovering that there are countless unconventional paths to building something big. The format is set — each guest will lead with a number, explain what they do, field questions about adjacent opportunities, and share their burning question for the hosts.

Chapter 2 · 03:32

Alex Daniels, $10M real estate magazine

The hosts immediately want to infect Alex with their 'sickness' for scale — why isn't this $100M yet? Alex pushes back gently: his real goal is to double profit (to $5M) within 11 months, not necessarily grow top line. Shaan introduces a tiering framework for customer relationships — Tier 1 (texting buddies who'd do you a favor), Tier 2 (email acquaintances), Tier 3 (transactional) — and challenges Alex to call his top 100 agents to understand the retention gap. The adjacent opportunity they're most excited about is home services, building informational content (like winter home prep tips) that pulls in service provider advertisers, similar to what neighborhood publication franchise Stroll has done at $100M+ in revenue. But the biggest surprise is Alex's AI setup: he uses Lindy to handle all inbound sales emails, follow-ups, and upsells autonomously, with human salespeople redeployed to customer experience — an implementation praised by the founder of Lindy himself as the most impressive he had seen.

Claims made here

Haven Lifestyles generates $10M in revenue and approximately $2.5M in profit from 40 real estate advertising magazines across the US and Canada.

Alex Daniels no source cited

Haven Lifestyles mails approximately 500,000 physical magazines per year via USPS postal routes.

Alex Daniels no source cited

Stroll, a neighborhood publication franchise company, is valued at over $100M in revenue.

Alex Daniels no source cited

Haven Lifestyles works with over 10,000 real estate agents annually and has approximately 1,500 on year-long auto-debit contracts.

Alex Daniels no source cited

Business
Haven Lifestyles: $10M From 40 Real Estate Magazines

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Alex Daniels owns 40 real estate advertising magazines across the US and Canada, generating $10M in revenue and $2.5M in profit with just 20 employees. There are no subscribers — he mails 500,000 magazines a year to targeted households via USPS postal routes, funded by real estate agents paying to advertise their listings.

Technology
Why Haven Lifestyles Uses Lindy AI Instead of Salespeople

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Technology

Haven Lifestyles replaced its core inbound sales function with Lindy AI, which handles every incoming email, follow-ups, and upsells automatically. Human salespeople have been redeployed to focus on customer experience and retention instead — a radical operational shift praised as the most impressive AI setup one tech founder had ever seen.

Chapter 3 · 20:31

Josh Weissenstein, $20M camp ground business

Shaan asks why anyone would choose campgrounds over other real estate categories, and Josh rattles off the structural advantages: strong cash yields, very attractive depreciation on roads and infrastructure (similar to manufactured housing), limited land/building value making them tax-efficient, and operational complexity that keeps unsophisticated buyers away. He explains that two major manufactured-housing REITs have significant campground exposure, which gave the team early validation for the asset class. The biggest culture decision came early: after initially planning to outsource property management, Cody moved in on-site for a full year learning every detail, leading to the conclusion that culture cannot be outsourced and no competent third-party operators existed who could scale with them. The resulting in-house operating company is now 350 people strong. Josh closes with memorable anecdotes — a nine-bank robber quietly employed at one site, and team members selling fallen trees for cash on Facebook — that illustrate the colorful realities of managing dispersed hourly workforces.

Claims made here

Team Outsider owns 16 campgrounds across 10 states with approximately 4,000 sites and generates around $20M in annual revenue.

Josh Weissenstein no source cited

Team Outsider's first campground near Grand Teton generated $500K in revenue and $150K NOI at acquisition, which was doubled to ~$300K NOI before refinancing.

Josh Weissenstein no source cited

Team Outsider raised approximately $60M in capital and its portfolio is now worth north of $100M.

Josh Weissenstein no source cited

KOA (Kampgrounds of America) has approximately 550 campground locations across the country and owns about 50 themselves, with the rest being franchises.

Josh Weissenstein no source cited

Chipotle pays general managers $10,000 for every former employee they trained who later becomes a general manager, even after the employee leaves the company.

Shaan Puri no source cited

Business
Why Campgrounds Are Underrated Real Estate

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Campgrounds offer strong cash yields, very attractive depreciation characteristics similar to manufactured housing (roads and infrastructure are depreciable), and limited land/building value — making them tax-efficient. The operational complexity that scares most investors is actually the moat: it creates value-add opportunities that simpler real estate doesn't.

Business
Chipotle's Secret: Making Frontline Workers Think Like Owners

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Shaan Puri shared that Chipotle pays general managers $10,000 for every employee they ever trained who later becomes a GM — even after they leave the company. This one incentive structure creates a culture where frontline workers invest in each other and think like owners, which is the hardest and most valuable thing in hospitality.

Business
Autopilot: Copy-Trading Politicians and Hedge Funds at Scale

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Autopilot lets retail investors automatically copy the trades of politicians and hedge funds using publicly reported data — without giving custody of funds away. The platform grew to managing $1.8B in assets in just 3 years, faster than it took Bill Ackman or Ray Dalio to reach $1B. The Nancy Pelosi tracker, launched on Twitter, was the viral growth engine.

Chapter 4 · 38:36

The $1.8B App Copying Politicians & Hedge Funds

After the three guests depart, Shaan gets reflective. He traces a personal evolution: a decade before MFM, success felt like a needle in a haystack — one brilliant idea to find, one narrow path to walk. The podcast, San Francisco, and meeting people like today's founders shifted that to pure abundance: tens of thousands of ways to win, and the real question is just which fits you. Sam and Shaan riff on what they'd borrow from each guest — Alex's enviable emotional stability and calm contentment, Brian's audacity and marketing creativity, Josh's outdoorsy lifestyle appeal. Sam pushes back on the idea that small and big businesses are fundamentally different: 'I am equally impressed by a billion-dollar company versus a $5M company.' They close by quoting Jesse Itzler — 'root for everybody, because when you root for everybody, you can never lose' — and Sam teases tomorrow's Ray Dalio interview as an extension of the same lesson in a very different key.

Claims made here

Autopilot manages $1.8 billion in assets under management within 3 years of operation, faster than it took Bill Ackman and Ray Dalio (10-15 years) to reach $1 billion.

Brian no source cited

Nancy Pelosi's tracked stock portfolio is up approximately 240% over the last 3 years, compared to the S&P 500 which gained roughly 30-40% in the same period.

Brian no source cited

Autopilot has raised approximately $16M in total funding and is going out to raise a Series B at a valuation of $300-400M.

Brian no source cited

Top portfolio managers ('pilots') on Autopilot earn between $1M and $2M per year in subscription revenue from followers.

Brian no source cited

Bill Ackman took approximately 5 years to raise $60M early in his career, while a trader named Peter Wolf raised $220M on Autopilot within 1 year.

Brian no source cited

Autopilot's GMV revenue is $30M while true ARR is approximately $22M, and the company is targeting $100M in recurring revenue by March of the following year.

Brian no source cited

Robinhood raised approximately $4 billion in emergency funding during the GameStop crisis to meet DTCC capital requirements.

Brian no source cited

The average AUM fee that users pay on Autopilot is approximately 3-4% annually.

Brian no source cited

Autopilot spent $450,000 on a UFC ring sponsorship featuring a Nancy Pelosi lookalike intended to be seen on camera next to Donald Trump.

Brian no source cited

BlackRock's Aladdin portfolio management platform generates approximately $6 billion per year for BlackRock.

Brian no source cited

Leopold Aschenbrenner's hedge fund started with approximately $500M in fundraising and has grown to approximately $5 billion in AUM.

Shaan Puri no source cited

Business
Pelosi Up 240% — How Autopilot Solved the Chicken-and-Egg Problem

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Nancy Pelosi's tracked portfolio is up approximately 240% over 3 years versus the S&P 500's 30-40%. Autopilot bootstrapped its marketplace by manufacturing supply-side content from publicly available congressional trading disclosures and hedge fund 13F filings — solving the classic two-sided marketplace cold-start problem.

Business
The $450K UFC Stunt With a Fake Nancy Pelosi

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Autopilot spent $450,000 to sponsor a UFC ring and plant a Nancy Pelosi lookalike in a front-row seat next to where Trump was supposed to sit, with the slogan 'Invest Like a Politician' visible on camera. Trump skipped due to an assassination attempt, killing the earned media opportunity. Brian admitted the ROI was limited but the brand awareness was real.

Business
Leopold Aschenbrenner: The 25-Year-Old Running a $5B Fund

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Leopold Aschenbrenner, a former OpenAI researcher who published the 'Situational Awareness' AI white paper, launched a hedge fund at 22 and has grown it to approximately $5 billion. He found the overlooked AI trade — SSDs and infrastructure bottlenecks instead of GPUs — and attracted top investors including Daniel Gross and Nat Friedman.

Society & Culture
Shaan's Mindset Shift: From Scarcity to Abundance

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Society & Culture

Before My First Million, Shaan Puri saw entrepreneurial success as a needle in a haystack — one brilliant idea to find. After a decade of the podcast, he realized opportunity is everywhere, with tens of thousands of ways to win. Today's session with three unconventional founders was a live demonstration of that abundance mindset.

No indexed bits in this chapter.

Show stoppers

Business
Pelosi Up 240% — How Autopilot Solved the Chicken-and-Egg Problem

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Business

Nancy Pelosi's tracked portfolio is up approximately 240% over 3 years versus the S&P 500's 30-40%. Autopilot bootstrapped its marketplace by manufacturing supply-side content from publicly available congressional trading disclosures and hedge fund 13F filings — solving the classic two-sided marketplace cold-start problem.

Society & Culture
Shaan's Mindset Shift: From Scarcity to Abundance

3 weird businesses doing $10M, $20M, $30M · Jun 30, 2026 Society & Culture

Before My First Million, Shaan Puri saw entrepreneurial success as a needle in a haystack — one brilliant idea to find. After a decade of the podcast, he realized opportunity is everywhere, with tens of thousands of ways to win. Today's session with three unconventional founders was a live demonstration of that abundance mindset.

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0 / 20 cited (0%)

Factual claims made this episode, and whether a source was named.

Haven Lifestyles generates $10M in revenue and approximately $2.5M in profit from 40 real estate advertising magazines across the US and Canada.

Alex Daniels no source cited

Haven Lifestyles mails approximately 500,000 physical magazines per year via USPS postal routes.

Alex Daniels no source cited

Haven Lifestyles works with over 10,000 real estate agents annually and has approximately 1,500 on year-long auto-debit contracts.

Alex Daniels no source cited

Team Outsider owns 16 campgrounds across 10 states with approximately 4,000 sites and generates around $20M in annual revenue.

Josh Weissenstein no source cited

Team Outsider raised approximately $60M in capital and its portfolio is now worth north of $100M.

Josh Weissenstein no source cited

Team Outsider's first campground near Grand Teton generated $500K in revenue and $150K NOI at acquisition, which was doubled to ~$300K NOI before refinancing.

Josh Weissenstein no source cited

KOA (Kampgrounds of America) has approximately 550 campground locations across the country and owns about 50 themselves, with the rest being franchises.

Josh Weissenstein no source cited

Autopilot manages $1.8 billion in assets under management within 3 years of operation, faster than it took Bill Ackman and Ray Dalio (10-15 years) to reach $1 billion.

Brian no source cited

Nancy Pelosi's tracked stock portfolio is up approximately 240% over the last 3 years, compared to the S&P 500 which gained roughly 30-40% in the same period.

Brian no source cited

Autopilot has raised approximately $16M in total funding and is going out to raise a Series B at a valuation of $300-400M.

Brian no source cited

Top portfolio managers ('pilots') on Autopilot earn between $1M and $2M per year in subscription revenue from followers.

Brian no source cited

Bill Ackman took approximately 5 years to raise $60M early in his career, while a trader named Peter Wolf raised $220M on Autopilot within 1 year.

Brian no source cited

Autopilot spent $450,000 on a UFC ring sponsorship featuring a Nancy Pelosi lookalike intended to be seen on camera next to Donald Trump.

Brian no source cited

Autopilot's GMV revenue is $30M while true ARR is approximately $22M, and the company is targeting $100M in recurring revenue by March of the following year.

Brian no source cited

Chipotle pays general managers $10,000 for every former employee they trained who later becomes a general manager, even after the employee leaves the company.

Shaan Puri no source cited

BlackRock's Aladdin portfolio management platform generates approximately $6 billion per year for BlackRock.

Brian no source cited

The average AUM fee that users pay on Autopilot is approximately 3-4% annually.

Brian no source cited

Robinhood raised approximately $4 billion in emergency funding during the GameStop crisis to meet DTCC capital requirements.

Brian no source cited

Stroll, a neighborhood publication franchise company, is valued at over $100M in revenue.

Alex Daniels no source cited

Leopold Aschenbrenner's hedge fund started with approximately $500M in fundraising and has grown to approximately $5 billion in AUM.

Shaan Puri no source cited