The Generations of Wealth
Welcome to "Generations Of Wealth," where wisdom meets wealth, hosted by the insightful Derek. Derek is not just a podcaster; he's a seasoned entrepreneur, astute investor, and strategic management expert with a passion for empowering others to build lasting legacies of prosperity. Derek's journey is a testament to the transformative power of entrepreneurship. Having navigated the dynamic landscapes of business and investing, Derek brings a wealth of experience to the microphone. With each episode, he distills his insights, offering a unique blend of practical advice, inspiring stories, and expert interviews.
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How a Missed Call Cost Him Two-Thirds of His Deals
<p>📄 Summary Ed Mathews spent decades in Silicon Valley software (including years at DocuSign) before leaving corporate life in late 2017 to invest in real estate full-time, something he'd first tried on the side back in 2011. His first deal — a four-family in East Hartford, CT — took three years of overthinking before his broker, tired of his excuses, put a signed contract on the hood of his truck and told him to sign it or never call her again; he held that property for 13 years and it became the foundation of a portfolio that eventually replaced his corporate income. Today his companies include...
Why Distressed Commercial Real Estate Is a Buying Opportunity
<p>📄 Summary Moshe Popack was working as an owner's rep on a Miami development when the 2008 crash hit, the construction lender pulled the loan, and he was left jobless with three kids and no financial safety net. He and his wife (also an attorney, who now runs operations while he focuses on strategy and growth) used their wedding money and savings to buy one foreclosed note on an apartment, eventually parlaying that into a nearly 400-unit Miami apartment deal that took months of rejected capital-raising attempts before one investor believed in them. From there, Moshe scaled to roughly 7,000 apartments acquired ove...
Is Now a Good Time to Buy Multifamily?
<p>📄 Summary John Todderud spent decades in software and IT consulting before buying his first small multifamily properties (a 3-unit, then a 4-unit) just after the 2008 crash, after deciding fix-and-flip's one-time payout and renovation-cost risk wasn't for him. He self-managed those first properties close to home, then deliberately bought farther away and hired property managers once he wanted to step back from day-to-day management — a shift that eventually let him invest anywhere in the US based on market fundamentals like population growth, job growth, and landlord-friendly regulation (something he says has steadily worsened in his home state of Washington). He share...
How Hard Money Lending Actually Works
<p>📄 Summary Kevin Amolsch bought his first house at 21 using books and library research rather than paid mentorship, and built an early real estate career around lease options — a strategy he mastered by going on five appointments every weekend in college. After partnering with a private-money broker named Susan in 2006, he built out a residential lending arm that grew into Pine Financial Group, but the 2008 crash hit hard: between owner-financed properties and personally guaranteed debt, Kevin had 55 properties when the market collapsed, teaching him painful lessons about adjustable-rate mortgages and overleverage. He rebuilt by shifting focus from closing individual deals to cr...
The Right Way to Finance an Investment Property
<p>📄 Summary Aaron Marsh spent 30 years in corporate finance before getting licensed right before the pandemic to help friends and family refinance at historically low rates — a side gig that snowballed into Marsh Lending once he discovered DSCR, non-QM, and commercial loan programs built for investment and short-term rental properties. He describes his ideal client using a complexity-vs-loan-amount framework: not first-time W2 buyers (served by every bank) or ultra-wealthy private banking clients, but high-complexity, high-dollar borrowers — business owners with multiple LLCs or thousand-page tax returns — who get rejected by traditional underwriting despite having the money to qualify easily. He breaks down how...
Investing in Real Estate Overseas: What to Know First
<p>📄 Summary Ladislas spent his twenties working for Nestlé in Switzerland, South Africa, and Ghana before a road trip with his parents from Oman to Paris — through Iran, Armenia, Georgia, and Turkey — opened his eyes to real estate opportunities in frontier and emerging markets. What started as one deal turned into a decade-plus career, and a blog he wrote to test his own thesis eventually grew into The Wandering Investor, now one of the largest firms helping clients invest internationally and acquire second residencies and citizenships. He explains that overseas investing works differently than in the US: markets are typically apartmen...
Why Real Estate Is a Relationship Business
<p>📘 Overview<br /> In this episode of the Generations of Wealth Podcast, Derek talks with Denis Shapiro, founder of SIH Capital Group, about the hard lessons he learned moving from single-family landlord to limited partner to full-time syndicator — and why he believes charismatic marketing, crowdfunding platforms, and even AI will never replace the relationship-driven side of real estate.</p> <p> </p> <p >⭐ Key Takeaways</p> An operator's marketing presence or public profile says nothing about whether they can actually run the business well — those are separate skill sets entirely. Before wiring capital as an LP, do real due diligence on the operat...
How to Legally Pay Only 2% Tax
<p>📄 Summary Mike built One Oak Financial (formerly ZGP Financial, then Mike Milligan CFP, then Ideas by Mike) around a simple belief: most "financial plans" are really just products — a 401(k), an IRA, an insurance policy — sold without ever answering why money matters to the client. His process starts by asking "why" repeatedly until clients get past the answer they think he wants to hear and reach the real one, then builds a written philosophy document covering taxes, retirement, investments, healthcare, and legacy before any product gets recommended. He explains that wealth is built primarily through three vehicles — real estate, retiremen...
Why I Stopped Betting On Appreciation: The Case For Cash Flow
<p >📄 Summary Travis Watts spent his first six and a half years as an active investor — fix-and-flips, vacation rentals, house hacking — before realizing it had become an unpaid full-time job, and shifted to passive LP investing around 2016. His first deal was a $50,000 check into a Phoenix multifamily value-add syndication, found through an accredited investor meetup in Boulder, Colorado; he doubled his money and built a strategy around stacking many smaller cash-flowing investments. Deal flow was abundant at the 2021-2022 market peak, but has slowed considerably since as floating-rate debt resets have wrecked some of his holdings, and he candidly shares that he...
Generational Wealth at Risk: Why Your Kids May Inherit a Home With a Mortgage
<p >📄 Summary David Bacon spent his career in banking and finance before landing at WellStreet Financial, where he now markets housing bonds — real estate-backed securities that pay 9% annual interest (paid quarterly) with a 3-year hold, bumping to 10% after that, with no management fees. Investor capital funds the "horizontal work" (water, power, sewage) that banks treat as speculative and won't finance affordably, which lets developers build neighborhoods instead of defaulting to premium-only homes to recoup costs. Every deal carries a 40% equity cushion and WellStreet stays in a primary lien position, capping exposure at 60% loan-to-value. Bonds start at $10, are open to non-accredited inves...
