This interview is about finding overlooked money-making opportunities in private markets. Guest Jeremy Giffon says many companies are neglected because founders are old or venture capital (VC) messed them up—like a firm making $10M a year but overfunded, so nobody profits. He likes these 'ghostship' companies (cash-flowing but ignored) and cast-off assets from big firms. He warns against overhyped holding companies and says don't overthink learning—just make that call you've been avoiding.
Jeremy Giffon (co-founder of private equity firm Tiny) explores special situation investment opportunities in the private market. The core thesis is that misaligned incentives and coordination problems create low-risk, high-reward arbitrage opportunities—such as acquiring "ghostship companies" (agin
Jeremy Giffon (Co-founder and GP of private equity firm Tiny) explores special situation investment opportunities in private markets. The core thesis is that misaligned incentives and coordination problems create low-risk, high-return arbitrage opportunities, such as acquiring "ghostship companies" (internet businesses with aging founders, no succession plans, yet stable cash flows).
Jeremy Giffon believes that a perfect investment should feature low capital expenditure, high customer retention, and predictable cash flows.
He argues that the ideal investment is one where "you never actually have to talk to anyone or understand the business, just understand the context and the incentives of all parties involved." Using the acquisition of a software business as an example, he states: "If it's a business where people pay millions of dollars annually, it clearly works. The software runs. What more due diligence do you need?"
Giffon quotes Groucho Marx's famous line, "I don't want to belong to any club that would have me as a member," and extends this to investing: "If it lands on your doorstep, you are either the luckiest person in the world, or everyone else has already given up on it. It's likely the latter, unless you have a very good explanation."
Giffon points out that in the current market environment, overfunded VC-backed companies have created a wealth of special situation investment opportunities.
He describes a typical scenario: a company with $10 million in annual revenue but $300 million in prior funding, leaving the founder unable to profit even with a solid business. "VCs have no incentive to tell you to shut down because they are in the outlier business. And founders are afraid to tell investors they have failed."
Giffon's solution is to communicate directly with both parties in private to facilitate a deal. "Both sides breathe a sigh of relief. VCs complain about the audit liabilities of all the dead companies, and founders want to exit. It's like a bad relationship—if you start thinking about breaking up, it's already too late."
Key data: Giffon once saw a company with $15 million in annual revenue, whose board member said, "That's in the Uber fund, we don't really care about it." He concludes: "You can recapitalize for $1 million, give the founder $500,000 in personal compensation, compress the remaining equity to 10-20%, then cut costs to make the business highly profitable."
Giffon emphasizes that the best investment strategy is "lazy"—set an extremely high quality threshold and wait rather than chase.
He shares Tiny's experience: "We went two years without deploying any capital. That was very difficult, but I can't imagine six years." He cites Charlie Munger's "too hard" box: "If you've been debating for three weeks, the conclusion is not to buy. It's not obvious enough, it doesn't hit you in the face."
Giffon's benchmark is: "Is this deal better than the last one? If yes, get excited; if not, pass. You want every deal to be your last investment—a company that can carry you through to retirement."
Giffon proposes a unique classification framework: determining whether an individual has experienced a "fall"—a life event where they were completely broken down and then rebuilt.
He explains: "You can see it in a person's eyes—whether they have truly been deeply humbled by life. This has nothing to do with their background or upbringing; it seems random." He offers an example: "Veterans who have been through multiple combat deployments may not get overly upset when things go wrong, while someone who has never faced setbacks might be completely thrown off."
Giffon believes this is useful for investment screening: "It's about whether you can 'sleep well at night.' Some people have stronger skills, but another person makes you feel at ease. They are accustomed to things going wrong and won't panic—this is primarily about downside protection."
Giffon sharply criticizes the cultural tendency to overvalue knowledge accumulation while neglecting action.
He points out: "All advice cancels itself out. You can find a successful counterexample for every piece of advice." He cites the parable of Mozart: a 12-year-old asks how to write a symphony, Mozart says "go to music school," the child says "but you were writing symphonies at 12," and Mozart replies, "I didn't go around asking people how to write symphonies."
Giffon argues: "If you find yourself asking questions like 'how to start a company,' it means you're not serious—you're just procrastinating, consuming information that feels productive. It's a seductive scam: packaging entertainment as education."
| Position | Guest Stance | Key Data |
|---|---|---|
| Overfunded VC-backed companies (ghostship firms) | Bullish (special situation arbitrage) | Annual revenue of $10-15 million, $300 million raised; capital restructuring possible with $1 million |
| Assets divested after large tech acquisitions | Bullish (coordination problem arbitrage) | E.g., Fortune 500 company acquires for $500 million, then divests a $50 million asset |
| Startups with dual product lines | Bullish (divestiture opportunity) | One product line is viable but insufficient to become a multibillion-dollar outcome |
| Marketing/lead generation assets in bankrupt companies | Bullish | After the main business fails, ancillary assets may be more valuable |
| Canadian market overall | Bullish (valuation arbitrage) | 30-40% cheaper than the U.S. |
| Holding companies | Risk warning (soon to be overvalued) | "I talk to 2-3 people every week who want to start a profitable holding company" |
| Venture capital (VC) overall | Risk warning | "I haven't seen any good explanation or data showing that the number of great companies increases over time" |
1. "The perfect investment is one where you never have to talk to anyone, just understand the incentives and coordination problems." — Giffon believes that most private market opportunities arise from "deadlocks" caused by conflicting interests among parties, and you simply need to "untangle them" to reap the rewards.
2. "If you've been debating for three weeks, the answer is don't buy." — Giffon cites Munger's "too hard" pile, arguing that good investments should "hit you in the face" and require no complex analysis.
3. "VCs have no incentive to tell you to shut down because they're in the outlier business." — Giffon points out that the communication gap between VCs and founders creates arbitrage opportunities, especially when a company has stable cash flow but the financing structure prevents the founder from profiting.
4. "Post-fall people let you sleep well at night." — Giffon's "fall" framework holds that those who have been thoroughly broken by life are more reliable because they "are used to things going wrong and don't panic."
5. "All advice cancels itself out — you can find a counterexample for every piece of advice." — Giffon criticizes the "cult of learning," arguing that most "how-to" questions are just procrastination in disguise.
6. "That phone call" — everyone knows the call they should make, but they avoid it for 40-50 years. — Giffon's core insight from Landmark Forum: identify and execute the difficult conversation you've been avoiding, and the payoff is enormous.
7. "The Canadian market is 30-40% lower than the U.S. because culturally it lacks America's 'unbridled optimism'." — Giffon believes that Canadian and British cultures tend toward "holding on to what you have," while American culture encourages "give it a try, it'll work out."
8. "Never let resentment fester in long-term partnerships — not even the smallest thing." — A principle Giffon learned from Tiny co-founders Chris and Andrew: any unresolved minor dissatisfaction will "ferment and grow," ultimately destroying the partnership.