AI Summary
5 min readWe Lost Millions So You Don't Have To
Austin Hankwitz and Robert Croak, hosts of the Rich Habits Podcast, have combined lifetime investing losses of roughly $3 million between them. Croak, a 40-year entrepreneur with over $300 million in lifetime revenues, estimates he has personally lost about $2.5 million across real estate, consumer brands, venture capital, restaurants, and crypto. Hankwitz, a multimillionaire in his late twenties with a finance background, has lost around $350,000 to $400,000, primarily through venture capital bets. Both treat these losses as tuition—and this episode is them handing over the lessons for free.
The Founder Trap and the Framework Problem
Croak's first never-again investment is startup ventures run by inexperienced founders. He learned this the hard way after losing $200,000 in a restaurant startup in 2015, $300,000 in a video-based technology startup around 2017, and $50,000 in a bowling technology startup that had licensing deals with Brunswick but still went nowhere. The bowling app, he explains, was supposed to let people bowl against each other in national leagues through an app. "It looked so incredibly promising," he says. "We had all these licensing deals, everything was great, and it just never went anywhere."
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What you'll learn
- 1 (00:41) **Three Investments Robert Would Never Make Again** - Robert introduces the episode's theme of sharing their biggest losing investments to help listeners avoid the same mistakes.
- 2 (03:36) **Investment #1 (Austin): Overly Optimistic Venture Investing** - Austin explains his first mistake was saying yes to almost every startup deal that crossed his desk.
- 3 (04:13) **Investment #1 (Robert): Betting on Inexperienced Founders** - Robert agrees, stating his biggest mistake was investing in startups run by new or inexperienced founders who lacked tenacity.
- 4 (10:15) **Investment #2 (Robert): Alcohol & Energy Drink Brands** - Robert explains why he will never invest in these consumer product categories again.
- 5 (12:20) **Investment #2 (Austin): Penny Stocks** - Austin admits to losing $10,000 in his early twenties on a penny stock tip from a friend.
- 6 (17:29) **Investment #3 (Robert): Specific Types of Real Estate** - Robert details the two real estate sectors he will no longer invest in: storage facilities and office buildings.
- 7 (20:33) **Investment #3 (Austin): High-Cost Professional Services** - Austin explains he will no longer blindly hire expensive professionals for services like tax strategy, bookkeeping, and legal documents.
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Guests on this episode
Show Notes
In this week's episode of the Rich Habits Podcast, Robert Croak and Austin Hankwitz talk about the investments they'd never made again.
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