Invest Like a Billionaire

Hosted by Aspen Funds

BusinessInterviews guests

Website RSS feed

Episodes

245

Latest episode

Jun 2026

Language

About the show

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/

Listen to episodes

60 recent

June 16, 202651 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, 202646 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 qualifyHow to run the Mega Backdoor Roth strategy inside a Solo 401(k)Why leveraged real estate here avoids UDFI taxes entirelyHow to get set up for as little as $650Have 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, 202646 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, 202635 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 industryHave 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, 202649 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, 202637 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, 202635 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, 202635 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 timeThe IRR trap most investors fall intoHow cash drag and taxes kill compoundingWhy wealthy investors focus on consistency, not home runsIf 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, 202642 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 nowThis 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, 202640 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 muchHave 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/