Invest Like a Billionaire

Aspen Funds
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Jul 29, 2025 • 23min

How to build a Passive Alternative Portfolio: The Wealth Pyramid

How do you build a strategic alternative asset portfolio? Most investors just jump at the first deals presented to them from their network. But in this episode, Ben lays out a strategic plan when building an alt portfolio, optimizing for long term yield and growth. In this episode, Ben is joined by Ellis Hammond, Aspen Fund’s Vice President of Capital to dive into The Wealth Pyramid. Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ And check out Ben & Bob’s company and invest along at https://aspenfunds.us/
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Jul 22, 2025 • 27min

He 20x'd his net worth in 4 years

Bronson Hill had a quick come-up from a salary job to a full time passive investor and capital raiser. But it hasn’t all been smooth sailing, and he’s learned some really important lessons along the way about how to be strategic about your path and create a framework to vet deals. In this episode, Bronson opens up about his portfolio, which includes some surprising asset classes. Check it out. Check out Bronson’s first book, Fire Yourself https://bronsonequity.com/how-to-fire-yourself/Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ And check out Ben & Bob’s company and invest along at https://aspenfunds.us/
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Jul 15, 2025 • 27min

Financial Advisor turned Passive Investing Pioneer with Jim Pfeifer

Jim Pfeifer, a former financial advisor and the founder of Left Field Investors, transformed his career by diving into passive real estate investing. He discusses why traditional financial advisors often shy away from real estate. Jim shares insights on navigating syndication challenges, particularly in a fluctuating market, and emphasizes the importance of community for support and education. He also highlights the significance of balancing real estate with liquid investments and strategies for risk reduction through diversification.
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Jul 8, 2025 • 26min

The Hard-Won Lessons Behind Aspen Funds with Jim Maffuccio

Jim Maffuccio, a co-founder of Aspen Funds, has been through some seriously challenging cycles. On the podcast, he and Ben get into how he rebuilt after two catastrophic wipeouts – and what he’s learned so it won’t happen again. He shares his CSI-like strategies for vetting sponsors today, and how he decides which deals go forward, and which he’s now turning down.Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ And check out Ben & Bob’s company and invest along at https://aspenfunds.us/
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Jul 1, 2025 • 32min

Deals We Didn't Do: The Rise of Pref Equity and when to Run like Hell

Discover how investment leaders decide which deals to pursue and which to pass on. Learn about the critical red flags in private credit deals and the challenges of navigating high-interest rates. The discussion sheds light on the discrepancies between optimistic rent growth projections and harsh market realities. Explore the shifting dynamics of cap rates and potential opportunities in prime markets, along with the unique challenges in multifamily real estate. This insightful dialogue emphasizes the need for thorough analysis and cautious strategies.
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Jun 24, 2025 • 29min

Creating a passive portfolio from the air with pilot Tait Duryea

Tait Duryea, a commercial pilot and founder of Turbine Capital, combines his passions for aviation and financial freedom. He discusses how to evaluate investment opportunities and manage risk like a skilled pilot. Listeners learn the unique financial challenges pilots face and why diversifying income streams is vital. Duryea also shares early real estate experiences, from navigating syndications to facing unexpected project setbacks. He underscores the importance of networking and learning from experts to achieve ultimate financial independence.
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Jun 17, 2025 • 22min

Making alt investing a family affair with Darrell Gargala

Darrell Gargala, a retired Air Force veteran turned real estate investor, shares his inspiring journey to building a seven-figure portfolio. He discusses how he keeps his projects dynamic and the crucial role of involving his children in wealth creation. Darrell emphasizes the importance of family collaboration in real estate, explains strategies for leveraging equity, and highlights their goal of achieving a $20 million net worth through a family LLC. He aims to instill financial literacy in the next generation while fostering a passion for investing.
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Jun 10, 2025 • 32min

Lessons from 25 years of investing success with David Shaw

David Shaw has 25 years of massively successful investing and entrepreneurship behind him – but he wishes he started even earlier. From a decade of W2 slogging, he ditched the pay cheque in favour of big swings, and it worked in his favour. In this episode, he tells Ben why he opts for A-class properties, the value of time in compounding wealth, and the entrepreneur’s secret weapon: scalability.Check out David’s podcast https://burnyourboatswealth.com/ Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ And check out Ben & Bob’s company and invest along at https://aspenfunds.us/
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Jun 3, 2025 • 13min

Headlines: Should I dump or double down on Oil & Gas?

The podcast dives into the current state of the oil and gas market, discussing whether to hold or invest more amid recent price declines. Insights into the critical supply-demand balance reveal the declining investment in new production and its future implications. Historical contexts of price fluctuations suggest a case for long-term investment strategies, while volatility management techniques are shared for successful investing. The episode also encourages listener engagement on these pressing investment topics.
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9 snips
May 27, 2025 • 33min

How HNW Family Offices’ are Investing in Alts with Kendall Laughlin

Kendall Laughlin, director at Arc Financial, specializes in guiding family offices of high-net-worth individuals. He discusses the evolution and significance of family offices in wealth management. Key topics include strategies for navigating wealth transitions, aligning family values with financial goals, and the role of alternative assets in achieving financial freedom. Laughlin also shares insights on preparing for the economic landscape in 2025, including the impact of tariffs and the importance of proactive planning amidst uncertainty.

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