Episode summary
Episode 370: From the oil rigs to speed skating to private credit - Brett Hickey of Star Mountain...
The Fiftyfaces Podcast
· · Guests: Brett Hickey
Summary
Brett Hickey traces his path from Edmonton, the oil rigs, and speed skating to finance, saying those experiences taught him work ethic, focus, and grit. He argues that supply and demand, not just skill, shape opportunity, and that early exposure to insurance and reinsurance helped him think in terms of probability, timing, and where the puck is going.
He explains that Star Mountain Capital was built around the US lower middle market because it offered structural tailwinds: aging business owners, banks moving upmarket, and valuation arbitrage from combining smaller businesses. Hickey says the firm aims to be an alpha specialist that adds portfolio diversification and, for taxable investors, tax advantages, rather than trying to be all things to all people.
A major theme is culture and leadership. Hickey says Star Mountain’s “star values” mean think like a shareholder, build trust, stay accountable, and show respect. He emphasizes broad equity ownership, aligned incentives, data-driven decision-making, and hiring people who are trustworthy and willing to work through stress together.
He also reflects on the uncertainty of starting a firm, including personal financial strain, and says the lesson was to plan carefully, surround yourself with strong people, and stay committed for the long term rather than jumping careers every few years.
Key takeaways
- Brett Hickey says Star Mountain focuses on the US lower middle market because supply-demand imbalance, aging owners, and valuation arbitrage create structural opportunity.
- Hickey argues that lower middle market lending can offer better covenants than larger-market credit because the work is more resource-intensive and less crowded.
- He says Star Mountain’s edge is not broad market beta but specialist alpha, diversification benefits, and, for taxable investors, tax advantages.
- Hickey ties the firm’s culture to broad equity ownership and “star values”: shareholder mindset, trust, accountability, and respect.
- He warns that the biggest investing mistake is ignoring where the puck is going and staying with trades after risk-reward deteriorates.
Notable quotes
“the one common denominator between oil drilling rigs, speed skating, and Star Mountain Capital is we're not afraid to work hard”
“I think that in insurance that's very probability driven, that helped form some of my mindset around how do we increase the probability of our desired results”
“the lower middle market has a lot of really thematic positive tailwinds”
“you can't do good business with bad people”
“I want to do what's selfishly in my best interest and give equity to everybody”
How the episode opens
One of the things that I think is critical in life is spending your time really thinking about the plan. Don't just rush into things. And and this, thankfully, I would say I generally got right, but I observe a lot of people not getting it right.
Right? So, we talk about the programs and I want to go in a learning environment. I want to be in a think tank to force myself to focus on my business, have people stress test it, poke holes, and so forth.
Let's get the business plan right. I see a lot of people just running into things and like, "Well, well, why? Well, I don't know.
I just want to do this. Yeah, but let's think, you know, in chess a few steps ahead, not just one move. The second thing is surround yourself with great people, talented, trustworthy people.
I think that's critical. It's again one of the aspects we look at investing in companies is looking at who we do business with. And we always have a saying at Starwood that you can't do good business with bad people.
I'm Ethan Devitt, and welcome to the 50 Faces podcast. A podcast committed to revealing the richness and diversity of the world of investment by focusing on its people and their stories.
This podcast series is kindly supported by Franklin Templeton and Alvine Capital. Franklin Templeton is a global investment firm that provides a broad range of investment solutions, including mutual funds, ETFs, alternative investments, wealth management, and technology-enabled financial services. Founded in 1947, the firm manages approximately 1.8 trillion in assets under management and serves individual and institutional investors across more than 150 countries.
Alvine Capital was founded in 2005. It's European-focused private capital advisory and placement agent that provides capital raising services to investment managers from offices in London and Stockholm.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- lower middle market investing
- private credit
- private equity
- tax advantage strategies
- leadership values
Companies and tickers mentioned
- C
- BEN
- Star Mountain Capital
- Citigroup Global Markets
- Franklin Templeton
- Alvine Capital
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Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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The Fiftyfaces Podcast, this episode and its artwork belong to Aoifinn Devitt. Octagon is not affiliated with the show; this page is an independent summary.
