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/

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, and what are red flags to look out for.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/

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. Find Tait’s podcast at https://passiveincomepilots.com/ and his firm at https://www.turbinecapital.vc/ AND check out Turbine Capital's e-book on oil & gas investing https://shorturl.at/4r9zU Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ Check out Ben & Bob’s company and invest along at https://aspenfunds.us/

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 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/

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/

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 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/

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://leadersatthehelm.substack.com/welcome Find out more about the podcast at https://www.thebillionairepodcast.com/And check out Ben & Bob’s company and invest along at https://aspenfunds.us/

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.thebillionairebook.org/⁠Check out Ben & Bob’s company and invest along at aspenfunds.us/⁠

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 at https://aspenfunds.us/

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/id1673140441 Find out more at https://www.thebillionairepodcast.com/And check out Ben & Bob’s company and invest along at https://aspenfunds.us/