Jim Pfeifer was a financial advisor working with clients invested in traditional stocks and bonds. Then he got into passive real estate investing – and he has a lot to say about why financial advisors can’t or won’t push real estate. He’s now built a hugely diversified passive portfolio and built a community helping others do the same. 

Check out Jim's company at passivepockets.com [http://passivepockets.com].

Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ [https://www.thebillionairebook.org/] 

And check out Ben & Bob’s company and invest along at https://aspenfunds.us/


Financial Advisor turned Passive Investing Pioneer with Jim Pfeifer

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/ [https://www.thebillionairebook.org/] 

And check out Ben & Bob’s company and invest along at https://aspenfunds.us/



The Hard-Won Lessons Behind Aspen Funds with Jim Maffuccio

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/ [https://www.thebillionairebook.org/] 

And check out Ben & Bob’s company and invest along at https://aspenfunds.us/


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

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/ 

Find out more about the podcast at https://www.thebillionairepodcast.com/ and PREORDER the Invest Like a Billionaire book at www.thebillionairebook.org/ [https://www.thebillionairebook.org/] 

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


Creating a passive portfolio from the air with pilot Tait Duryea

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/ [https://www.thebillionairebook.org/] 


And check out Ben & Bob’s company and invest along at https://aspenfunds.us/

Making alt investing a family affair with Darrell Gargala

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/ [https://www.thebillionairebook.org/] 


And check out Ben & Bob’s company and invest along at https://aspenfunds.us/

Lessons from 25 years of investing success with David Shaw

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/ [https://www.thebillionairebook.org/] 
And check out Ben & Bob’s company and invest along at https://aspenfunds.us/

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

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/

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

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/⁠ [https://www.thebillionairepodcast.com/] and preorder the Invest Like a Billionaire book ⁠⁠www.thebillionairebook.org/⁠ [⁠www.thebillionairebook.org/]

Check out Ben & Bob’s company and invest along at aspenfunds.us/⁠ [https://aspenfunds.us/]

Headlines: Will tariffs lead to a recession?

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/


When the exit doesn’t go as planned with Curt Stevenson

Most investors don’t know that the ultra-wealthy (billionaires, institutions, family offices) have large portions of their investment portfolios allocated to investments outside the stock market and in alternatives like real estate, private equity and hedge funds. Meanwhile, the average high net worth investor is mostly invested in stocks and bonds. Join Bob Fraser, Jim Maffuccio, and Ben Fraser as they dive into the world of alternative investments, uncover strategies of the ultra-wealthy, discuss economics and interview successful investors and alternative investment experts.

Evan Umberger

Shows