From Tactical to Transformational: Real Estate, Conferences & Conversations

In this powerhouse episode, real estate mogul and entrepreneur Ashley Wilson joins Derek Dombeck for a candid, unscripted conversation that dives deep into multifamily real estate, the true value of in-person networking, and her mission to bring transparency and innovation to the conference world. Ashley unpacks her journey from clinical research to managing over $160M in real estate assets, co-founding Apartment Addicts, and launching the platform Conference Connect. The discussion also tackles the current multifamily market, negotiation dynamics, personal accountability, and the future of live events. Whether you’re a new investor, a seasoned operator, or someone passionate about personal growth—this episode hits on all cylinders.
Escape the 1031 Trap: Create Freedom with the Deferred Sales Trust

In this insightful episode of the Generations of Wealth Show, host Derek Dombeck welcomes Brett Swarts, founder of Capital Gains Tax Solutions, to challenge the traditional 1031 exchange and unveil a more flexible, investor-friendly strategy: the Deferred Sales Trust (DST). Brett shares how DST empowers investors to defer capital gains taxes, diversify investments, and most importantly—reclaim their time and freedom.
Through powerful stories of clients who exchanged active property management for peace of mind and increased cash flow, Brett makes the case that building wealth should never come at the cost of your family or lifestyle. If you’ve built up significant equity and are looking for a better way out, this episode is your roadmap.