Invest Like a Billionaire

Dr. Peter Linneman, Wharton professor and real estate economist known for Lineman Associates and influential housing research. He unpacks why a shrinking federal workforce shifts labor to the private sector. He explains how rate cuts and capital rotation revive real estate. He explores AI’s realistic productivity effects and why multifamily demand stays strong amid a single-family shortage.

In this debate, financial experts Caleb Guilliams and Jim Dew tackle the contentious topic of whole life insurance and infinite banking. Caleb, a financial advisor and founder of BetterWealth, argues for strategic insurance use, while Jim, a wealth advisor at Dew Wealth Management, emphasizes practicality. They discuss the hype surrounding infinite banking, reveal common misconceptions, and critique the math that often leads to misunderstanding. Their insights into alternatives for accessing capital and the integration of insurance into financial plans are especially noteworthy.

Venezuela's oil reserves are vast, yet production is dismal due to sanctions and aging infrastructure. The hosts debunk claims about immediate impacts on oil prices and delve into the role of the shadow fleet managing black-market oil. They discuss the geopolitical implications of policing these fleets and how global forces like Ukraine threaten supply. While short-term recovery is unlikely, the discussion reveals a long-term investment thesis that underinvestment in oil assets may create significant opportunities by 2026.

Caleb Guilliams, founder of BetterWealth.com, advocates for whole life insurance as a strategic financial tool. Jim Dew, from Dew Wealth Management, brings 30 years of expertise serving entrepreneurs. Together, they dissect the pros and cons of whole life vs. term insurance. They highlight the complexity and common pitfalls of insurance sales tactics. The duo debates the suitability of whole life for investors, emphasizing timing, opportunity costs, and the importance of policy design while also flagging some products to avoid.

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/

Discover how to quickly evaluate multifamily investment opportunities with essential metrics. Learn about the importance of a high-level smell test to gauge a business plan's viability. Dive into cap rates, distinguishing between going-in and exit cap rates, and their impact on property value. Understand yield on cost for value-add deals and how debt yield shapes lender perspectives. Gain insights into the most sensitive inputs affecting underwriting outcomes, and refine your approach by asking smarter questions.

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/

Ken McElroy and Bob Fraser took questions from a live audience at an Invest Like a Billionaire book launch event this summer. We’re bringing that Q&A to the feed because it has a lot to say about the current state of real estate, especially multifamily, from two experienced real estate investors. 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/