Moneywise – “Weird Side Bets That Made Founders Millions”

Episode Date: December 16, 2025
Host: Jackie Lamport (Producer/Host; standing in for Sam Parr and Harry Morton)

Episode Overview

This episode of Moneywise takes an entertaining and insightful dive into the unconventional, often risky, "side bets" that have fueled huge financial wins for tech founders and entrepreneurs. Rather than focusing on safe, traditional investments, host Jackie Lamport shares real stories of founders who have bet big – and won – in unexpected ways: angel investments, opportunistic real estate, geoarbitrage, early crypto, and even buying existing businesses. The tone is candid, practical, and peppered with personal anecdotes and direct advice.

Key Discussion Points & Insights

1. Angel Investing: Turning $10,000 into $1.2 Million

• [02:23] Jacqueline Johnson shares: Her first ever angel investment—$10,000 in Away Luggage—yielded a $1.2M buyout ~7 years later.
• Quote:

  “I wrote like a $10,000, I think check and did not have $10,000, nor was I an accredited investor at the time... Cut to... was able to be bought out of that investment for close to $1.2 million.” – Jacqueline Johnson [02:23]

• Risk and Reality: She acknowledges this level of return is rare. Out of 25 angel investments, 3 have exited profitably, most are in play, and a couple went to zero.
• Motivation: Many effective angel investors, including Johnson, are motivated by being "founder first" and supporting communities they care about (e.g., women founders).
• Andrew Wilkinson [04:22] adds: The energy comes from being actively involved, not just writing checks:

  “That’s like the most fun to me... actually being involved as like an angel who is like an operator is really fun.”

• Tips for Angel Investing [04:43]:
  • Cap allocation in your portfolio (consider it “play money”)
  • Stick to what you know (founders, markets, business models)
  • Be patient; returns take time, or may never come

2. Opportunistic & Lifestyle-Driven Real Estate

• [05:54] Ann Maloom narrates: She bought a Dominican Republic house for $3.6M, sold it 18 months later for $5.6M (+$2M, plus rental cashflow).
• Quote:

  “I bought a house... for $3.6 million. And then I sold that 18 months later to Albert Pujols for $5.6 million. And I rented that out along the way.” – Ann Maloom [05:54]

• Broader Strategy [06:32]: Real estate is ~20% of her portfolio, includes personal residences, gifts for family, and speculative investments like a $14M condo deposit.
• Alternative Asset Classes:
  • [09:15] Jeff: “The real estate that I own today is cash flowing real estate that brings in about 2 million a year, 2 1/2 million a year...”
  • [09:28] Rajeev Ganesha: Successfully bought a mobile home park years ago, still performing.
• Downsides [09:37]:
  • Illiquidity (hard to get out fast if needed)
  • Not always passive—requires attention and management

3. Geoarbitrage: 3x Wealth Overnight Just by Moving

• [10:18] Rob Hoffman’s Story: Moved from Canada to Medellin, Colombia; $1M net worth became $3.2M in local currency and living costs plummeted.
• Quote:

  “If I stay in Colombia, I can jump ahead in life financially, lifestyle wise, like 10 years.” – Rob Hoffman [10:18]

• Key Insights:
  • Not just about currency advantage—he immersed himself in the community and learned the language
  • Made $10,000 in savings last a year to fund his startup
  • Recommends it for post-exit founders or those with portable businesses

4. Crypto before Crypto Was Cool: Mining Bitcoin for a Million

• [12:53] Unnamed founder: Mined Bitcoin as a “subject matter enthusiast” in libertarian subreddits in 2013 and accidentally left the fortune on a hard drive.
• Quote:

  “I started mining bitcoin and that's actually where I made my first million.” – Guest Founder [12:53]

• Found the crypto haul years later when organizing old media storage; at the time of recalling, Bitcoin was at an all-time high.
• On Crypto as a Side Bet [14:20]:
  • Chris Cook: “It’s like playing at the casino.”
  • Rob Walling: Got “too much” crypto only because it ballooned, not because he allocated that much.
  • Lesson: The people happy with their crypto bets are those who actually sold high (“You got to know when to get out!” – [14:32]).

5. Buying Existing Businesses Instead of Starting from Scratch

• [16:45] Andrew Wilkinson: Modeled himself after Warren Buffett, buying and growing small tech companies, resulting in “tens of millions in profit” and eventually taking one public.
• Quote:

  “I basically copied Warren Buffett and started buying small tech companies and just growing them over time and holding them... [one was] worth hundreds of millions of dollars.” – Andrew Wilkinson [16:45]

• [17:30] Alex Hormozi: Used liquidity from an exit to buy “cash flow”—his words make clear it’s not an afterthought but a calculated move.
• [17:38] Corey Mitchell: Bought a demolition company in Iowa with $3M revenue, added services, grew it to $24M.
• Tips on Buying Businesses [18:03]:
  • Stick to business types you know—don’t jump industries blind
  • Buy simple, profitable businesses with predictable customers and margins
  • Have an active plan—don’t treat it as “passive” income

Notable Quotes & Memorable Moments

• “Angel investing is the best... but that is not normal!” – Jacqueline Johnson [03:04], on the away.com success.
• “I get to invest in these founders... actually being involved as like an angel who is like an operator is really fun.” – Andrew Wilkinson [04:22].
• “I bought a house... then I sold that 18 months later to Albert Pujols for $5.6 million.” – Ann Maloom [05:54].
• “If I stay in Colombia, I can jump ahead in life financially, lifestyle wise, like 10 years.” – Rob Hoffman [10:18].
• “I started mining bitcoin and that's actually where I made my first million.” – Guest Founder [12:53].
• “I basically copied Warren Buffett and started buying small tech companies...” - Andrew Wilkinson [16:45].
• “Buy what you know... buy simple, profitable businesses... don't think of it as passive.” – Jackie Lamport, summarizing [18:03].

Timestamps for Important Segments

| Timestamp | Segment | |-----------|---------| | 02:23 | Jacqueline Johnson on away.com angel investment | | 04:22 | Andrew Wilkinson: Angel investing as fun, active participation | | 05:54 | Ann Maloom's beach house flip in the Dominican | | 09:15 | Jeff on cash-flowing real estate | | 10:18 | Rob Hoffman on geoarbitrage in Colombia | | 12:53 | Founder: Accidental Bitcoin million-dollar find | | 14:20 | Rob Walling: The crypto portfolio “got too big” | | 16:45 | Andrew Wilkinson: Buying and holding tech companies | | 17:38 | Corey Mitchell: Scaling a demolition business | | 18:03 | Summary and actionable tips for buying businesses |

Recurring Themes

• Diversification doesn't mean being random: The best “weird bets” are those that founders understand and play to their strengths.
• Action and involvement matter: Passive checks rarely outperform active engagement.
• Healthy skepticism and discipline: Cap percentages, avoid overconcentration, honor your risk tolerance.
• Boring isn’t bad: Even the wildest portfolios rest on safe assets like index funds and ETFs.

Further Resources

• Specific episodes referenced on angel investing (Oren Hoffman), geoarbitrage (Rob Hoffman), and portfolio breakdowns are available in linked show notes (see podcast description).
• Hampton community: Private peer group for high-growth founders – more at joinhampton.com.

Summary prepared for listeners seeking actionable, transparent, and sometimes eccentric financial strategies from founders who've tried it all – and made millions along the way.