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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/
Find out more at https://www.thebillionairepodcast.com/ or join us at https://aspenfunds.us/
237 Episodes
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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/
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)sIf 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/
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 marketsWhere capital is still flowing in private investmentsWhat investors may be getting wrong right nowHow AI is changing deal analysis and due diligenceHave 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/
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 outlookKey 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/
1What 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/
Is private credit about to collapse?The $1.7 trillion private credit market has grown rapidly, but recent write-downs from major funds like BlackRock and KKR are raising concerns about a potential private credit crisis.In this episode, Ellis Hammond sits down with Ben Fraser, CIO of Aspen Funds, to explain what’s happening in private credit, why some funds are showing stress, and what investors should watch for before investing in private credit funds.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/
Recorded live at the Best Ever Conference 🎙️ What really changes when you go from making money → managing money?In this episode, Bob & Ben sit down with Christopher Nelson of WealthOps to break down how high-net-worth individuals structure, steward, and scale their wealth — without needing billions.We cover:• How to run a “micro family office”• How to give your wealth purpose beyond returns• How to build a portfolio that supports your lifestyle and long-term legacy• The mindset shift from income generator to family CEOIf you’ve built meaningful wealth and are asking, “Now what?” — this conversation is your next step.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/
Join Ben Fraser as he talks with Seth Bradley, Esq., Chief Legal Officer at Tribevest, about an opportunity hiding in plain sight: turning your network into a fund of funds.In this episode, you’ll learn:• How the fund-of-funds model works and why it’s gaining momentum• How professionals are leveraging their networks to raise capital• The steps to start your own fund of funds, the compliant wayIf you’ve ever wondered how to go from investor to fund manager, this episode breaks it down step by step.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/
Bob and Ben recap the biggest insights from our 2026 Economic Outlook and Macro Forecast presentations, featuring perspectives from Belinda Román, John Chang, and Jay Parsons. They cover GDP growth expectations, potential Fed rate cuts, housing market trends, and real estate investment signals — plus why investor sentiment may matter more than the data in the near term.A fast, data-driven snapshot of the 2026 economy, rates, and real estate outlook.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/
In this episode, Bob Fraser shares his presentation from our 2026 Macro Economic Outlook event, breaking down the investable megatrends shaping 2026. From AI and productivity to real assets and interest rates, learn how to invest with the tide and position your portfolio for what’s next.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/
California is pushing a wealth tax. Missouri just eliminated capital gains tax. What does that mean for investors?In this episode, Ellis Hammond sits down with Bob and Ben Fraser to break down the billionaire tax battle between CA vs. MO—and how high-net-worth investors adapt. Learn how the wealthy use LLCs, balance-sheet thinking, and smart tax strategy to legally protect and grow their wealth.If you want to pay less in taxes and keep more of your returns, this episode is for you.Don’t miss the 2026 Macro Economic Outlook—announced in the outro of this episode! Sign up here: https://aspenfunds.us/2026-macro-economic-outlook/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/
In this episode, Bob and Ben Fraser sit down with Dr. Peter Linneman, Wharton professor and real estate economist, to unpack the forces shaping today’s economy. He explains how capital flows influence property prices, examines AI’s impact on the labor market, and reviews housing trends—from multifamily demand to rent growth—revealing how economic shifts shape real estate and productivity. Essential insights for investors, economists, and housing professionals.Don’t miss the 2026 Macro Economic Outlook—announced in the outro of this episode! Sign up here: https://aspenfunds.us/2026-macro-economic-outlook/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/
Is infinite banking a smart wealth strategy or just well-marketed?In Part 2 of this two-part debate, Ben and Bob continue their conversation with Caleb Guilliams ( @BetterWealth ) and Jim Dew ( @DewWealth ) Together, they unpack the realities of infinite banking and whole life insurance. Ben shares his own experience implementing these strategies, while the group debates the math, tradeoffs, and why infinite banking is often oversold to investors.Thinking about adding infinite banking to your financial plan or wealth strategy? This episode is packed with expert insights and real-world lessons.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/
Everyone’s talking about Venezuela oil and global oil prices - but what does it really mean for investors in 2026?Venezuela has the world’s largest proven oil reserves, but output remains low due to sanctions, underinvestment, and outdated infrastructure. In this episode, Ellis, Bob & Ben cut through the headlines to explain the real impact of Venezuela on the global oil market.Discover: • Why Venezuela’s oil won’t move prices in the short term • Hidden forces shaping global oil supply • How Russia, Iran, and other key players could influence markets • What the headlines got right — and what they missedHave more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
Is whole life insurance a smart investment strategy or an expensive mistake?In Part 1 of this two-part deep dive, Ben and Bob sit down with financial experts Caleb Guilliams (Better Wealth) and Jim Dew (Dew Wealth Management) to break down the truth about whole life insurance and infinite banking.They explain whole life insurance, compare whole life vs term life insurance, reveal what makes a strong life insurance policy, highlight common mistakes, and show when these strategies benefit your wealth, and when they don’t.Investors and entrepreneurs: this two-part series gives you the clarity the financial world doesn’t.Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
Ben & Bob join Ellis Hammond to look back on a landmark year in which Aspen deployed approximately $140 million in capital. We walk you through our biggest verticals to see how oil & gas, debt & credit, and multifamily fared this year. And we share some strategies we’re bringing into 2026.Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
Spencer Levy, a Senior Economic Advisor at CBRE, has been watching this dynamic year in real estate closely. He joins Ben & Bob today to share his hot takes on where 2026 is going to take us: what cities he has his eyes on, market trends, interest rates, and the political landscape’s impact on real estate. We go through the four pillars of real estate: industrial, retail, multifamily and office. Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
David Neidig recently had a liquidity event, selling his family business. So suddenly, he’s shifted from a business owner mindset to an investor mindset. We dig into how he’s making that leap and why he’s going for alternatives. Plus, we get to hear about his unique sale: he sold the business via an ESOP (Employee Stock Ownership Plan). Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
Ever wondered how to review an underwriting file in 10 minutes or less? In this Part 2, Ben Fraser shares shortcuts and guidelines for evaluating multifamily opportunities.Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
Your essential guide to reviewing an underwriting file. Join Ben Fraser as he shares shortcuts and guidelines for evaluating multifamily opportunities.Have more questions, or want more resources like a tax calculator? Go to investlikeabillionaire.org to learn more about our community. Check out Ben & Bob’s company and invest along at https://aspenfunds.us/
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Great podcast. Participants have good chemistry. First time in quite a while I felt like the interviewer was reading my mind - asking exactly the questions I had.