By Ben McGregor | October 31, 2026
Harris Kupperman of Praetorian Capital told Undervalued Shares that outlier investment ideas drive multi-bagger returns. His fund is up roughly 9x net since 2019, including 129 percent in 2020 and 142 percent in 2021. The interview focuses on idea generation, networking, and cycles. Kupperman manages a hedge fund and publishes free investor letters at pracap.com. He also runs the KEDM newsletter.
How did Kupperman start generating outlier ideas?
Kupperman said he started trading in high school after a summer job cleaning pools. “I run the the Street.com trading. Actually, I got second place, but it's good enough when you're like 17 years old.” He is a history major with no formal finance training. “I've never really had any guidance. I'm a history major. Uh, one day there'll be a bull market in history and I can go back to my profession, but this pays better for now.” He looks for “weird unique angles and quirks in the market.” These statements are his personal history. His high-school trading result is his recollection.
What role have multi-baggers played in his results?
Kupperman said unique ideas have shaped his career despite volatility. “I like to say that I won't put anything on if I don't think it can 3x in three years or 5x in 5 years. And throughout my career, it's it's those multi-baggers, just those 5, 10, and 20x uh situations uh put on with a lot of capital and a big meaty position that have moved the needle.” He avoids small price targets. “I'm not the sort of guy that buys a stock at 20 cuz I think it's going to 25.” Verified net returns for Praetorian Capital Fund LLC show +129.49 percent in 2020 and +142.87 percent in 2021, with cumulative gains near 9x since January 2019 through September 2026. These are fund-reported figures after fees.
Where do the best ideas come from?
Kupperman said differentiated ideas often start with quirky friends outside mainstream finance. “I think a lot of being successful at this game is having unique quirky friends that are kind of a little on the periphery of uh finance as opposed to, you know, down the middle sitting in Manhattan.” He cited Sven’s dinosaur-bones idea as an example that was initially dismissed. Talking to smart friends who have conviction in a position that is down 30 or 40 percent is a strong starting point. “What does my friend have a big position in that it's not working for him and he has absolute conviction that he's still right? I'm going to get him at a 30 40% better cost basis.” These are Kupperman’s opinions on idea sourcing.
How does he find listed ways to express themes?
Kupperman noted that many interesting themes lack a clean public-market vehicle. Sven argued that with roughly 100,000 listed companies worldwide, a global investor can usually find at least one stock that fits an unusual idea. Kupperman agreed that for smaller portfolios this is often viable, citing past Venezuela exposure through Canadian listings. He also recalled looking at defaulted Lebanese bonds after Sven wrote about them. These are practical observations from both speakers. The existence of cross-listings is a market fact.
How does Kupperman organize and filter ideas?
Kupperman said he is not highly organized. “I actually use uh traditional notepads. Usually notepads that I get from some investment conference... I do about one notepad a year. I keep very terrible notes.” Ideas often crystallize in late-night conversations with market friends. “The later the night goes and the more we consume, the more likely it is that someone has a great idea. I just hope that someone remembers in the morning.” He focuses on cycles in commodities, refining, shipping, and other areas where up-cycles are explosive and down-cycles produce bankruptcies. Politicians’ decisions beyond election windows create opportunities in second-tier markets. These are his process descriptions.
Why is staying open to people and places important?
Kupperman said idea generation is a lifestyle of taking meetings and traveling. “Any city on this earth with more than 100,000 people, I have a follower and if I reach out and say I'm going to be in this place, they will come to me.” Meeting people in different countries provides differentiated views. He also reads free or delayed sources such as Value Investors Club, Seeking Alpha, Substack, and hedge-fund letters. “You fill or kill really fast. If it's a fill, it goes into my notepad.” Knowledge and networks compound over years. These are Kupperman’s practices and opinions.
How does he use limited partners and expert networks?
Kupperman said his investors are a valuable resource. “Our LPs are so smart, so successful, and they know so much.” For a bottle of wine, senior people with decades of industry cycles will share insights that paid expert networks often cannot. “A guy who really needs 500 bucks doesn't know anything.” This is his view on research quality.
What is the hard part after an idea is on?
Kupperman said the real skill is handling the two or three scary moments that occur during a three-to-five-year hold. “When that bad data point comes, you either say, ‘Okay, cycle's done. Let's get the hell out. If you're going to panic, make sure you panic first.’ Or you say, ‘This trend has tons of legs. Let's add on this pullback.’” Experience helps distinguish a temporary setback from a broken thesis. Cyclical industries can sometimes become quasi-secular and re-rate. “That's the rarest thing, but when it happens, it's just the biggest home run possible.” These are Kupperman’s observations from 25 years of investing.
Why does this matter to a retirement-age reader?
Outlier ideas that can multiply capital matter when traditional portfolios face higher inflation and rate pressure. Kupperman’s emphasis on cycles, second-order effects, and disciplined sizing after conviction is tested offers a framework for evaluating resource and commodity themes that mining readers often follow. His track record of large gains in concentrated positions is verified for the years cited, but past results do not predict future ones. The process requires time and network-building that compounds slowly.
What to watch next
- November 3, 2026: US midterm elections. Results can shift policy and risk appetite that affect cycle trades.
- November 6, 2026: US employment report. Labor data will influence rate expectations and growth outlooks.
- December 9, 2026: FOMC rate decision and Summary of Economic Projections.
- Company earnings and production updates in the resource sector that test whether cyclical themes are inflecting.
A dated risk from recent weeks is elevated market volatility in precious metals and related equities. Gold closed near $3,875 and silver near $49 on October 30 amid rising rate-hike odds. For inflection investors, such moves can create the scary data points Kupperman described, requiring a clear decision to exit or add.
This article is for educational purposes only and does not constitute investment advice, a recommendation, or an offer to buy or sell any security. Past performance is not indicative of future results. Readers should conduct their own research and consult a qualified financial advisor before making any investment decisions. Canadian Mining Report and its authors may hold positions in securities mentioned.
Sources
- Undervalued Shares interview with Harris Kupperman, published October 30, 2026: https://www.undervalued-shares.com/weekly-dispatches/how-to-generate-outlier-investment-ideas-interview-with-harris-kupperman/ (YouTube: https://www.youtube.com/watch?v=HBKaI4sQsp0)
- Praetorian Capital Fund performance tear sheets and letters at pracap.com (verified net returns for 2020, 2021, and cumulative since 2019)
- Forbes and Institutional Investor coverage of Kupperman’s returns and process
