Invest Like a Billionaire

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....

How does Aspen decide what deals to jump for, and which to turn away? In this new series, Deals We Didn’t Do, the leadership team is bringing you behind the scenes on how we make those calls. 

In this episode, Ben and Bob Fraser, Ellis Hammond and Jim Maffuccio go over a recent Rescue Preferred Equity Fund or “Bail-In Fund” they turned down. They walk through how you can calculate if these kinds of private credit deals might pan out...

Tait Duryea has always loved two things: flying planes and building financial freedom. He’s built a life that combines these two elements, and he’s helping other commercial pilots achieve the same success he has in alternatives. In this episode, he tells Ben how he decides if a deal is ready for liftoff, how he thinks about risk assessment, and how he’s getting from Point A to Point B on his own financial goals. 

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Darrell Gargala started investing in real estate as a way to stay busy after retiring from the Air Force. But it’s become a passion, and he’s even bringing his kids into the fold. In this episode, he shares how he’s built up a 7 digit real estate portfolio, why he keeps his projects active, and how he's passing on this knowledge to his kids.

Find out more about the podcast at https://www.thebillionairepodcast.com/ and...

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.

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The oil & gas price has softened, but does that mean you should dump your investments, or double down? Bob and Ben Fraser discuss the headlines and the concerns they are hearing from their investors. They share their own perspectives, how oil & gas have fared in the past downturns, and where they’re betting that investment is going next. 

Find out more about the podcast at https://www.thebillionairepodcast.com/ and PR...

Kendall Laughlin is an investor himself, but his real passion is helping family offices set goals and reach them. He serves as a director for 10 family offices, ranging from 20-55 Million, and he shares how they think about strategy and plan their legacies, and what those families are thinking about in 2025. 

Check out Kendall’s family office work at https://arkfinancial.com/ and his coaching services at https://leadersatt...

In our first Headlines episode, Bob Fraser joins Ben to talk about the big question on many Aspen investors' minds: are we heading towards a recession? With tariff news and trade war threats dominating the news cycle, it’s easy to get worried, so Bob and Ben are taking a look at what the data says and its impact for investors. 

Find out more at www.thebillionairepodcast.com/⁠ and preorder the Invest Like a Billionaire book ⁠⁠www.the...

Curt Stevenson has had a hugely successful career in tech consulting and entrepreneurship, and has lived through the big ups and some big downs. Curt’s ready to settle into an early retirement, so he shares with Ben how he’s building a portfolio that will offer him stable, reliable income for decades to come. 

Find out more at https://www.thebillionairepodcast.com/

And check out Ben & Bob’s company and invest along...

Jordan Linscombe is a bold entrepreneur and a careful investor. He and his wife Mindi have built up their bridal shop – Something New Boutique – over the past 18 years into something amazing. So much so, that Jordan has taken his own path as a real estate professional to manage their assets. 

Check out Jordan’s business https://www.somethingnewboutique.com/ and his podcast https://podcasts.apple.com/us/podcast/the-something-new-show...

Wes Hill has been in the real estate game since he was young. And he didn’t start with a trust fund or a legacy  – he built his 7-figure passive income portfolio through small steps, sacrifices and smart moves over many decades. Learn how Wes is thinking about real estate investing today after a career in the industry, and how you can build out your portfolio starting today.

Find out more at https://www.thebillionairepodcast....

Francois Braine-Bonnaire knows how to jump on an opportunity. He moved across the world for the perfect investing moment, and it’s paid off. In this conversation, he shares his advice on when to go all in, when to walk away, and when to know you’ve peaked. 

Check out Francois’ life coaching business at www.tobeoptimized.com

Find out more at https://www.thebillionairepodcast.com/

And check out Ben & Bob’s company and ...

A very special episode – Bob Fraser, co-founder of Aspen Funds (and father of Ben Fraser) is in the hot seat. Bob tells the story of how he has won it all, lost it all, and built it back up again. We go inside Bob’s portfolio to hear what asset classes he’s most excited about today, and what lessons he has learned from his decades of investing that are preparing him to weather the storms of the future.

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Your favorite podcast about winning the alternative investing game is back, with a new focus. Every episode we’ll be taking you inside the portfolios of everyday millionaires to learn how they have built their successful portfolios. We’ll keep you up-to-date on the economics that matter to you, investable megatrends opportunities we’re watching closely. 

Make sure you’re subscribed so you don’t miss an opportunity to hear how you ca...

Mark Kohler and Ben Fraser discuss tax strategies, asset protection, and the political landscape's impact on small businesses. They also touch on efficient business structures like the S corporation, the importance of revocable living trusts in estate planning, and the power of Roth IRAs for building tax-free wealth. Mark is the founder and board member at Direct IRA and Senior Partner at KKOS Lawyers.

Steven Pesavento, Principal at Von Finch Capital, shares his journey in real estate, emphasizing mindset, financial strategy, and self-investment. We explore current market opportunities in multifamily real estate and private credit amidst economic shifts.

This conversation with Brett Swarts explores the numerous benefits of DSTs, their role in deferring capital gains taxes beyond real estate transactions, and practical examples of people who have successfully applied this strategy.

We discuss how Ownify's model allows first-time buyers to gradually purchase homes through fractional ownership, bypassing traditional mortgage hurdles.