Invest Like a Billionaire

Aspen Funds

The insider’s guide to alternative investing. Each week, join Aspen Funds’ Bob and Ben Fraser to hear the latest insights from the world of alternative investing. We’ll give you an inside look at the portfolios of everyday millionaires who are making real returns and passive income through alternative investments in real estate, private equity, hedge funds, and more. And we’ll keep you up-to-date with market news, macroeconomics and investable megatrends so you can invest with confidence.

Find out more at https://www.thebillionairepodcast.com/ or join us at https://aspenfunds.us/

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20 episodes
Updated Tuesday

Episodes20

Newest first

Tuesday · 27 min
He Reviewed $8 Billion in Retirement Accounts. Here's What He Learned.
Most investors think retirement accounts are only for stocks and mutual funds. Adam Bergman, founder of IRA Financial, explains how wealthy investors use self-directed IRAs, Roth IRAs, and alternative investments like private equity and real estate to build long-term wealth. Learn the biggest retirement investing mistakes, key IRS rules, and strategies that can help you maximize your retirement portfolio. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
July 21 · 41 min
The Economic War Every Investor Should Understand
Tariffs are only part of the story. In this episode, Ellis Hammond sits down with Bob Fraser and Ben Fraser to break down the real economic battle between the U.S. and China. Learn how tariffs, industrial policy, semiconductors, AI, rare earth minerals, and free markets are shaping the future of the global economy and what every investor should understand to navigate the opportunities and risks ahead. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
July 14 · 34 min
Why Now Is the Time for Private Alternatives
The stock market is at record highs but does that mean it's time to rebalance? In this episode of Invest Like A Billionaire, Ellis Hammond sits down with Bob Fraser to discuss why today's market may be strengthening the case for private alternatives, where he's personally investing today, and how billionaire investors think about portfolio construction. They cover portfolio diversification, private credit, multifamily real estate, liquidity, taxes, cash flow, and the biggest mistakes investors make when moving beyond stocks. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
July 7 · 43 min
Why Your Index Fund Isn't as Safe as You Think
Are index funds still safe? As the AI boom reshapes the market, nearly 40% of the S&P 500 is now concentrated in just 10 companies. In this episode, Bob Fraser, Ben Fraser, and Ellis Hammond, break down what this historic concentration means for investors, what history can teach us about today's AI-driven market, and why great companies don't always make great investments. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
June 30 · 39 min
The Fed is About to Change Everything. Are You Ready?
A new Fed Chair could change investing for the next decade. Kevin Warsh is calling for a fundamental shift in how the Federal Reserve approaches interest rates, inflation, and economic policy. If he's successful, the investing playbook that's defined the past 20 years may no longer apply. In this episode, Bob Fraser, Ben Fraser, and Ellis Hammond break down what Warsh's vision could mean for stocks, bonds, real estate, inflation, the yield curve, and your portfolio. Learn how investors can prepare for a new era of higher rates, market-driven capitalism, and long-term investing. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
June 23 · 34 min
The Economy Absorbed a War, Tariffs, & a New Fed Chair. Here's Why It Didn't Break.
At the start of 2026, many economists expected growth to slow. Since then, we've had tariffs, inflation concerns, conflict in the Middle East, oil volatility, and a new Fed Chair. Yet the economy keeps growing. In this episode, Bob Fraser and Ellis Hammond sit down with Belinda Román, Associate Professor of Economics at St. Mary's University, to discuss what's changed, what's surprised her, and whether the economy is proving more resilient than investors expected. We cover tariffs, inflation, consumer spending, interest rates, AI-driven productivity, recession risks, and what investors should be watching in the second half of 2026. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
June 16 · 51 min
Don't Waste Your 30s or 40s: The Wealth Moves That Matter Most
Are your 30s and 40s the most important decades for building wealth? In this episode, Ben Fraser and Ellis Hammond share the wealth-building lessons they've learned the hard way, from investing mistakes and lifestyle creep to the power of compounding, skill development, and building a portfolio that can create long-term financial freedom. If you're serious about growing your wealth, this conversation will help you focus on what actually matters. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
June 9 · 46 min
Think You Don't Qualify for a Solo 401(k)? Think Again.
Most high-income earners assume the Solo 401(k) isn't for them. They're wrong. If you have a side hustle, a consulting gig, or a small investment LLC, you likely qualify, and you could be sheltering up to $144,000 per year in tax-free contributions. Bob Fraser and Ellis Hammond sit down with George Blower, co-founder of MySolo401k.net, to break down exactly how this works and why so few people are taking advantage of it. You'll learn: The two simple requirements to qualify How to run the Mega Backdoor Roth strategy inside a Solo 401(k) Why leveraged real estate here avoids UDFI taxes entirely How to get set up for as little as $650 Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
June 2 · 46 min
The 2026 Macro Reset: Oil, Inflation, and the Assets Poised to Win
Nobody predicted 2008. Nobody predicted COVID. And whatever causes the next market crisis probably won't be what investors expect. That's what makes today's environment so challenging. Just a few months ago, markets were expecting rate cuts and easing inflation. Now oil prices are surging, treasury yields are rising, and some analysts are drawing comparisons to the inflationary pressures of the 1970s. In this episode of Invest Like A Billionaire, Bob Fraser, Ben Fraser, and Ellis Hammond break down the biggest economic shifts happening right now, from energy markets and inflation to AI-driven productivity, real estate, private credit, and the opportunities they see emerging in an increasingly uncertain landscape. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
May 26 · 35 min
The Dirty Secret Behind Bourbon (And How to Profit From It)
Bourbon might be one of the most overlooked alternative investments in America. In this episode of Invest Like a Billionaire, Brian Rosen, founder of InvestBev, breaks down how his firm built a portfolio around bourbon barrels, beverage brands, and alcohol infrastructure and why family offices are paying attention. We cover: • Why bourbon barrels have historically produced strong returns • The “dirty secret” behind most liquor brands • How billionaires invest in beverage infrastructure • Why alcohol is considered a non-correlated asset • The macro trends reshaping the beverage industry Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
May 19 · 49 min
The Skills That Built Your Wealth Can Destroy It featuring TIGER 21's Founder
Most entrepreneurs know how to build wealth. Very few know how to keep it. In this episode, Bob Fraser and Ellis Hammond sit down with Michael Sonnenfeldt, founder and chairman of TIGER 21, whose members collectively manage more than $280 billion in assets. They discuss why entrepreneurs often become bad investors after a big exit, the mindset shift from builder to allocator, how the ultra-wealthy are investing today, and why time eventually becomes more valuable than money. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
May 12 · 37 min
You Don't Have A Tax Strategy, You Have A Tax Return
Most entrepreneurs think they have a tax strategy. What they actually have is a tax return. In this episode, Patrick Lonergan of Vital Wealth breaks down the biggest tax mistakes high earners make, why most CPAs are reactive instead of strategic, and how wealthy entrepreneurs use tax planning, cash flow management, and alternative investments to build long-term wealth. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
May 5 · 35 min
The 5 Real Estate Rules Everyone Broke (And Lost Billions)
“Good” deals are losing money right now. So what went wrong? In this episode of Invest Like A Billionaire, Ben and Ellis break down the 5 rules most real estate investors ignored and how breaking them led to massive losses across the market. More importantly, we show you how to apply these rules to win in the next cycle. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
April 28 · 35 min
Why Billionaires Choose Funds Over Single-Asset Deals
Most investors think picking the right deal is how you win. It’s not. In this episode of Invest Like a Billionaire, we break down why investing deal by deal can quietly destroy your returns and what actually builds long-term wealth. We cover: Why “good” deals still lose money over time The IRR trap most investors fall into How cash drag and taxes kill compounding Why wealthy investors focus on consistency, not home runs If you’re investing in real estate or private markets, this will change how you think about building wealth. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
April 21 · 42 min
$1 Trillion in Real Estate Is Breaking (Here’s What Happens Next)
$1T in multifamily debt is coming due and most of it already doesn’t work. Is this a real estate crash or the next buying opportunity? We brought in Dugan Kelley, co-founder of Kelley Clarke Law and a leading real estate and SEC attorney, to break down what’s actually happening in the multifamily market. In this episode: -The multifamily “maturity wall” explained -Why 2020–2022 real estate deals are in trouble -How rising interest rates broke deal economics -What happens next: loan modifications, forced sales, or foreclosure -What real estate investors need to know now This isn’t 2008. It’s a valuation reset in commercial real estate. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
April 14 · 40 min
Roth Conversions: Why Waiting Is Costing You Millions
If you have a large IRA, there’s a good chance you’re playing the game exactly how the IRS wants, and it’s costing you millions. Most investors are told to defer taxes. That’s where they go wrong. In this episode, CFP and tax strategist Craig Wear explains why Roth conversions often make more sense sooner and more aggressively than most people think. We cover: • Why waiting can cost you • How RMDs increase your tax bill • The hidden tax trap for retirees • When to convert and how much Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
April 7 · 33 min
Why Serious Investors Never Invest in Their Own Name
Most investors focus on what to invest in. Wealthy investors focus on how they invest. In this episode, we break down one of the simplest (and most overlooked) strategies: using an LLC to structure your investments. Bob’s been doing this for years. Ben hasn’t. So… is this actually something you should be doing? We cover: • Why serious investors don’t invest in their own name • How this setup can reduce taxes and increase flexibility • The mindset shift of treating your investments like a business • How it unlocks strategies like Solo 401(k)s If you’re building wealth, this is a foundational move worth understanding. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
March 31 · 46 min
What 10,000 High-Net-Worth Investors Are Actually Doing Right Now w/Litan Yahav (Vyzer)
What are high-net-worth investors actually doing with their portfolios right now? In this episode, Bob and Ben sit down with Litan Yahav, co-founder of Vyzer, to break down insights from $30 billion in real investor data—not surveys, but actual portfolio behavior. The results are surprising. From a major shift out of private markets… to where capital is flowing instead… to how investors are rethinking due diligence—this episode gives you a clear look at how sophisticated investors are positioning today. In this episode: The shift from private to public markets Where capital is still flowing in private investments What investors may be getting wrong right now How AI is changing deal analysis and due diligence Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
March 24 · 25 min
Oil Just Spiked — Are We Headed for a Recession?
Is a recession coming? Oil prices, inflation, and Fed rate cuts explained. With oil prices rising and tensions in Iran escalating, many investors are asking: Will higher oil trigger a recession in 2026? In this episode, Ellis sits down with Bob & Ben to break down: -Oil prices and their impact on inflation -How energy costs affect the economy and markets -Fed interest rate cuts and recession risk -Consumer spending trends (70% of GDP) -What happens if oil hits $100–$120 -Real estate and investment outlook Key insight: Rising oil alone doesn’t cause a recession—but sustained high prices can. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/
March 17 · 31 min
PPMs That Scare the Sh*t Out of Me (Real Investing Horror Stories)
What should investors actually look for in a Private Placement Memorandum (PPM)? In this episode, Ellis Hammond sits down with Ben Fraser and Bob Fraser to break down real examples of PPMs that raised major red flags — including unlimited sponsor expenses, huge placement fees, and deal structures that shift risk entirely onto investors. They walk through what a private placement memorandum is designed to do, why experienced investors focus more on the risks than the upside, and the specific sections you should read before investing in a private deal. If you invest in real estate syndications, private equity, private credit, or alternative investments, learning how to evaluate a PPM can help you avoid costly mistakes. Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠ to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

Invest Like a Billionaire

He Reviewed $8 Billion in Retirement Accounts. Here's What He Learned.

The Economic War Every Investor Should Understand

Why Now Is the Time for Private Alternatives

Why Your Index Fund Isn't as Safe as You Think

The Fed is About to Change Everything. Are You Ready?

The Economy Absorbed a War, Tariffs, & a New Fed Chair. Here's Why It Didn't Break.

Don't Waste Your 30s or 40s: The Wealth Moves That Matter Most

Think You Don't Qualify for a Solo 401(k)? Think Again.

The 2026 Macro Reset: Oil, Inflation, and the Assets Poised to Win

The Dirty Secret Behind Bourbon (And How to Profit From It)

The Skills That Built Your Wealth Can Destroy It featuring TIGER 21's Founder

You Don't Have A Tax Strategy, You Have A Tax Return

The 5 Real Estate Rules Everyone Broke (And Lost Billions)

Why Billionaires Choose Funds Over Single-Asset Deals

$1 Trillion in Real Estate Is Breaking (Here’s What Happens Next)

Roth Conversions: Why Waiting Is Costing You Millions

Why Serious Investors Never Invest in Their Own Name

What 10,000 High-Net-Worth Investors Are Actually Doing Right Now w/Litan Yahav (Vyzer)

Oil Just Spiked — Are We Headed for a Recession?

PPMs That Scare the Sh*t Out of Me (Real Investing Horror Stories)