Frequently Asked Questions.
Straight Answers. Zero Spin.
At Upside, we believe transparency builds trust. Whether you're wondering how we invest, who qualifies, or what happens if we don't perform, this page is here to give you clear, honest answers. If you're asking the question, there's a good chance someone else already has too. And if you don’t find what you're looking for, we’re always just a call or email away.
1. What makes Upside different from traditional investment firms?
Most firms charge you a management fee regardless of performance. We don’t. At Upside, we only get paid when you do, through a performance-based model. If you don’t earn at least 1.17% in a given month (equal to 15% annually), we don’t make a dime. Period. And in over a decade of running this strategy, we’ve never missed.
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2. How do you invest the money?
We don’t chase trends or stay fully invested in volatile markets. Instead, we make a small number of high-conviction, short-duration trades throughout the year. That means your money is exposed to risk only when the probability of success is highest, which leads to fewer drawdowns and more consistency.
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3. What is the 15% cap and why does it exist?
To reduce risk and volatility, we cap annual returns at 15%. That allows us to focus on consistent gains without swinging for the fences. It also gives us the flexibility to spend long periods in cash, protecting your capital while waiting for better opportunities.
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4. What fees do I pay?
None, unless we make you money. Unlike traditional firms that charge annual management fees regardless of performance, Upside only earns a performance fee on gains above 1.17% per month (equivalent to a 15% annual return). You keep the first 1.17% each month, and we retain any gains above that. Some months there may be nothing for us, and that’s okay. We’re here to earn our keep, not take your money when the market doesn’t cooperate.​
5. Is this strategy proven?
Yes. Since 2014, this exact approach, capped at 15% per year, would’ve turned $1 million into over $4.5 million. Even with the cap, it still dramatically outperforms a typical advisor-managed S&P 500 portfolio, especially after inflation and fees., which would have grown to just $1.8 million.
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6. Can I take my money out?
Yes. You can withdraw annually with 30 days’ notice before year-end. You’ll receive your full balance (net of any applicable performance fees), typically within 10 business days of the new year.
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7. What kinds of investors do you work with?
Upside is designed for qualified investors with $5 million or more in total assets (including real estate). Many of our clients are business owners, professionals, or individuals with concentrated equity positions looking for a smarter, more consistent way to grow and preserve their wealth.
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8. How do I track performance?
We provide monthly performance reports, along with an annual statement and audited year-end financials. You’ll also receive a Schedule K-1 for tax reporting each March.
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9. Who manages the fund?
The strategy is run by seasoned investors with over two decades of experience managing portfolios for some of the nation’s wealthiest families. We left the traditional world behind to build a better model, one that actually rewards discipline, protects capital, and aligns completely with you.