Charlie Kirk, the founder of Turning Point USA and host of “The Charlie Kirk Show,” has built a financial empire using an unconventional approach that prioritizes reinvestment over salary—and his investment philosophy during market downturns has proven remarkably profitable.
Speaking on the "The Iced Coffee Hour" podcast, Kirk revealed that he invests 75% to 80% of everything he makes, maintaining a highly diversified portfolio that spans private equity, mutual funds, index funds, real estate, and even emerging technologies. His disciplined approach to wealth building offers valuable insights for investors looking to maximize long-term returns.
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The Founder’s Sacrifice That Built an Empire
Kirk’s most striking financial decision was foregoing any salary from Turning Point USA for five years after founding the organization. “I believe a founder should reinvest all money back into the company during its early stages unless there are urgent family needs,” Kirk explained. “It’s a test of a founder—how much they pay themselves in the initial years.”
This reinvestment strategy paid dividends. Today, while Kirk takes a $300,000 annual salary from Turning Point USA, he donates $350,000 back to the organization, making it “basically a wash.” He explained on "The Iced Coffee Hour" podcast that his primary income now flows from The Charlie Kirk Show, which reaches an estimated 2 to 3 million people daily across multiple platforms including Rumble, YouTube, TikTok, and over 400 radio affiliates. Ask ChatGPT
The ‘Buy the Dip’ Strategy That Worked
Kirk’s most profitable investment move came during the COVID-19 pandemic when he aggressively purchased triple-leveraged Nasdaq ETFs. “I started buying triple-leveraged triple Q during the tariff stuff and COVID,” Kirk said on the podcast. “It was the easiest bet because I viewed the country’s shutdown as self-inflicted and reversible.”
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His contrarian approach proved prescient. While many investors fled the market during the March 2020 crash, Kirk saw opportunity. “I started buying when I saw signs of hope,” he said, demonstrating the classic “be greedy when others are fearful” mentality that has enriched savvy investors throughout history.
Macro Over Micro: A Diversified Approach
Unlike many retail investors who focus on individual stock picks, Kirk told "The Iced Coffee Hour" podcast that he emphasizes macro investment decisions over micro-level company analysis. His portfolio includes exposure to traditional assets like index funds and mutual funds, but also alternative investments including real estate flipping projects in Chicago and Arizona.
One particularly interesting holding is his investment in “Anagram,” which he describes as “the fundamental technology below crypto”—essentially betting on blockchain infrastructure rather than individual cryptocurrencies. “It’s like buying the plumbing of the crypto industry,” Kirk explained.
While Kirk did make a symbolic investment in Tesla Inc. TSLA due to his support for Elon Musk, CEO of Tesla, he generally avoids individual stock picking in favor of broader market exposure.
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The Wealth Management System
Kirk credits his success to surrounding himself with the right team, specifically mentioning Doug Degroot as his money manager. However, Kirk maintains control over major strategic decisions while delegating day-to-day management. “I make the macro decisions,” he noted, emphasizing that he receives significant “deal flow” but says no more often than yes.
The Philosophy Behind the Portfolio
For Kirk, wealth serves a specific purpose beyond accumulation. “The best thing about being wealthy is not being poor and not having to worry about money,” he said on "The Iced Coffee Hour" podcast. “The middle ground with good cash flow is ideal—having billions can lead to constant worry about lawsuits and identity issues.”
His primary driver remains purpose over profit. Kirk views money as a “nice reward” but emphasizes that his happiness comes from “impacting people’s lives, speaking truth, having purpose, and helping save civilization.”
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