Leaving Corporate America: The Real Estate Investing Journey Nobody Talks About
In this episode of the Generations of Wealth Podcast, Derek sits down with Jon Weiskopf, a former Apple engineering leader who walked away from a successful corporate career to build his own path through real estate investing, private lending, and entrepreneurship.
Jon shares his transition from designing and managing projects for Apple around the world to building a portfolio of multifamily investments, assisted living facilities, and a specialized private lending business.
The conversation explores risk, freedom, entrepreneurship, lending, real estate operations, and what it really takes to leave the security of a paycheck behind.
How to Navigate Lending, Syndications & Industrial Investing in 2025
In this 37-minute episode, Derek Dombeck sits down with David Hansel, founder of Alpha Funding and Lucerne Capital Partners, for a deep dive into the evolution from single-family flips to commercial and industrial real estate investing. David shares his journey through market cycles, how he built a thriving lending business during the 2008 crash, and how he transitioned into managing over $300M+ in assets through funds and syndications.
You’ll gain first-hand insights into hard money lending, fund management, and small-bay industrial investing — with actionable advice for both new and seasoned investors.
Syndications vs. Funds (and SEC Traps): Kevin Kim’s Playbook for Raising Capital the Right Way
Derek sits down with securities attorney Kevin Kim (Fortra Law) to demystify raising capital for real-estate deals—covering when to use a syndication vs. a fund, realistic startup costs, 506(b) vs. 506(c) advertising rules, what actually happens when regulators come knocking, and how note offerings compare to LP/GP fund structures. They also hit modern twists like series LLC funds, why most beginners should avoid tokenization, and a pragmatic outlook for late-2025 across SFR, small multifamily, and shaky commercial sectors. If you raise money (or plan to), this is your compliance-and-strategy cheat sheet straight from a former regulator.