Growing the Money with Rich Lennon

113 Episodes

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Episode 112: How Taxes Are Silently Destroying Your Wealth (And the Strategy That Stops It)

2026-03-0516:35

What if the biggest thing holding you back financially isn’t your income, your investments, or even your spending, but your taxes? Most people focus on making more money. Very few focus on keeping more of what they earn. And over time, that quiet leak adds up to hundreds of thousands, even millions, of dollars lost. In this episode, Rich Lennon joins the show to break down why income taxes are the single biggest obstacle to building real wealth, and what you can legally do about it. From the ...

Episode 111: One Florida Investor Just Lost 30 Deals (And Every Private Lender With Him)

2026-03-0214:32

What happens when 30 real estate deals fall apart at the same time, and the private lenders lose everything? It’s happening right now. Rich actually likes subject-to deals. They can be powerful tools when used correctly. But when you ignore basic rules, equity, underwriting, legal structure, and skin in the game, things can go bad fast. And when they do, the private lender is usually the one left holding the bag. In this episode, Rich breaks down what went wrong in a major Florida subject mat...

Episode 110: Investor vs. Business Owner – Why One Goes Home and One Goes Back to Work

2026-02-2612:18

What if the biggest difference in real estate isn’t how much money you make, but whether you have to keep showing up to make it? There’s a massive mindset gap between being a business owner and being an investor. One has to go back to work after the meeting. The other doesn’t. In this episode, Rich shares two stories that hit him hard. Both involved walking into rooms full of high-level builders and commercial real estate professionals, and realizing he was completely underdressed. This episo...

Episode 109: How I Bought 30 Rentals Without Using a Single Dollar of My Own Money

2026-02-2313:28

What if the reason you’re stuck at one or two rentals is that you keep using your own cash? Most investors think they need to save more money before they can scale. Bigger down payments. Bigger reserves. Bigger bank account. But what if that mindset is actually the thing slowing you down? In this episode, Rich breaks down the exact strategy he used to buy his first 30 rental properties, without using a single dollar of his own money. No gimmicks. No hype. Just borrowing money the right way, r...

Episode 108: How to Turn Your $8 Hour VA Into a Manager Who Actually Runs Your Business.

2026-02-1906:32

What if your $8/hour virtual assistant could eventually run your entire company? Most entrepreneurs hire VAs to handle small tasks. Answer emails. Pull lists. Follow up on leads. And that’s where it stops. But what if you could turn that same person into a true manager, or even a COO? In this episode, Rich breaks down exactly how he’s done it inside his own real estate business. He explains the difference between a task-based assistant, a true manager who owns 90-day goals, and a COO who make...

Episode 107: The $75K Credit Card Loan That Vanished - 3 Mistakes That Destroyed a Private Lender.

2026-02-1609:37

What if trying to make a safe 12% return ended up costing you $75,000, plus 25% interest? This episode is different. Rich shares a real call he received from a private lender who wired $75,000 to a local flipper, using a 0% credit card. No mortgage. No deed of trust. No security. And now the borrower has disappeared, while the credit card company wants its money back. It’s a tough story. But it’s also a powerful lesson. In this short but important episode, Rich breaks down the three critical ...

Episode 106: Why I Changed My Mind on Debt Three Times (The Wealth Curve That Explains Everything)

2026-02-1210:11

Is debt the key to building wealth, or the thing that quietly puts you at risk? The honest answer? It depends on where you are in your journey. In this short yet powerful episode, Rich Lennon breaks down how his opinion on debt has changed three times as his net worth, confidence, and priorities have evolved. From wanting everything paid off, to leveraging hard to grow, to shifting back toward security, this episode walks through the real-life thought process behind each move. You’ll Learn Ho...

Episode 105: 140+ Loans, Zero Losses -The Private Money Lending System Every Investor Needs - Part 2

2026-02-0934:18

What if the real secret to safe, consistent lending isn’t finding better borrowers, but writing better loans? In Part 2 of this series, Rich Lennon goes deep into the actual mechanics that protect private lenders when things go wrong. This isn’t theory or hype. It’s the real-world structure Rich has used across 140+ loans without a single loss. He breaks down exactly how notes, deeds of trust, defaults, penalties, insurance, and personal guarantees work together to give lenders control, not h...

Episode 104: 140+ Loans, Zero Losses - The Private Money Lending System Every Investor Needs -Part 1

2026-02-0535:48

What if lending money felt safer than flipping houses? No rehabs. No tenants. No late-night phone calls. Just steady returns and real control. This isn’t theory or hype. It’s a practical, asset-based approach built from years of experience, including what to do when deals go sideways and how to protect yourself before they ever do In this episode, Rich Lennon breaks down the private money lending system he’s used to fund over 140 loans without a single loss. He shares the real rules he ...

Episode 103: Why I Pay My Taxes With Credit Cards (The Unpopular Airline Miles Strategy)

2026-02-0209:32

What if paying taxes didn’t have to feel like pure pain? What if it could actually work in your favor? Most people dread tax day. Some would literally rather swim with sharks than deal with it. But in this episode, Rich Lennon shares an unconventional strategy he personally uses to turn one of life’s biggest expenses into something useful: airline miles. Rich walks through why paying taxes with credit cards can make sense if you do it the right way, how extensions really work and where people...

Episode 102: How Fractional Lending Works - The $100K Loan That Returns 30% (Explained)

2026-01-2944:27

Most real estate investors obsess over acquiring more deals, more units, and more flips. But very few ever question what happens after they’ve already built wealth. What do you actually do with the money you make? How do you grow it without adding more employees, stress, or operational complexity? In this episode, Rich Lennon breaks down a strategy most operators never consider until they hit the ceiling on flipping and rentals: fractional lending. Rich explains how he pivoted from a 14-emplo...

Episode 101: The BRRRR Method Is Dying - Here’s What Smart Investors Are Doing Instead -Part 2

2026-01-2629:03

What if the strategy that helped you build your portfolio is now quietly working against you? BRRRR used to be the go-to play. But in today’s market, higher prices and interest rates have changed the math, and many investors are feeling it. In this episode, Rich Lennon breaks down why BRRRR doesn’t work the way it used to and why the refinance step has become the biggest problem. Using real numbers from his own portfolio, Rich walks through how deals that once cash flowed now lose money, and ...

Episode 100: The BRRRR Method Died – Here’s What Smart Private Lenders Are Doing Instead -Part 1

2026-01-2228:40

What if the strategy that helped you build wealth is now the thing quietly holding you back? For years, the BRRRR method was the go-to playbook. Buy, rehab, rent, refinance, repeat. It worked. However, today’s market appears quite different. Higher rates, tighter deals, and thinner margins have changed the math, even for experienced investors. In this episode, Rich Lennon joins the show to talk honestly about why BRRRR doesn’t work the way it used to, and what smart investors are doing instea...

Episode 99: How to Write Checks From Your IRA Without Waiting on Your Custodian

2026-01-1913:14

What if your retirement money could move as fast as you do? No waiting. No paperwork bottlenecks. No missed deals because a custodian took days to respond. In this episode of Growing the Money, Rich Lennon breaks down one of the most misunderstood and powerful tools in self-directed investing: checkbook control. Rich explains how investors use trusts or LLCs to gain direct access to their IRA funds, why speed matters in real estate, and the exact process to do it the right way, without trigge...

Episode 98: The Fractionalized Note Strategy That Turns 20% Loans Into 50%+ Returns – Part 2

2026-01-1524:55

What if the real secret to higher returns isn’t chasing riskier deals, but structuring smarter loans? Most investors think 20% is the ceiling in private lending, until they learn how to fractionalize notes the right way. In this episode, Rich Lennon continues the deep dive into his fractionalized note strategy and shows how breaking a single loan into multiple pieces can dramatically increase your yield, without swinging for the fences. Rich explains how he underwrites deals, protects downsid...

Episode 97: The Fractionalized Note Strategy That Turns 20% Loans Into 50% Returns -Part 1

2026-01-1224:49

What if a 20% loan could quietly turn into a 40–50% return, without incurring more risk and without requiring additional hours? Most people think you need bigger deals, more properties, or complicated funds to boost returns, but that’s not actually where the leverage is. In this episode, Rich Lennon breaks down the fractionalized note strategy he uses to turn simple private loans into outsized returns. He explains how he structures deals, why lazy money is the key ingredient, and how he prote...

Episode 96: From 60-Hour Weeks Flipping Houses to 5 Hours a Week Lending -Part 2

2026-01-0830:37

What if the real goal wasn’t owning more properties, but getting your time back? In part two of this conversation, Rich Lennon gets real about what happens after you build a big rental and flipping business. The long hours. The stress. The moment you realize you’re asset-rich… but tired. Rich walks through how he went from grinding 60-hour workweeks flipping and managing rentals to spending just a few hours a week as a lender, and why that shift completely changed his life. This isn’t a hype-...

Episode 95: From 60-Hour Weeks Flipping Houses to 5 Hours a Week Lending - Part 1

2026-01-0532:03

What if working harder isn’t the answer, and the real win is working less while your money does the heavy lifting? In this episode of the Proximity Podcast, Clayton and Stephanie sit down with real estate veteran Rich Lennon to unpack how he went from grinding through 60-hour weeks flipping houses to spending just a few hours a week as a private lender. No hype. No shortcuts. Just real experience, real lessons, and honest talk about what actually works over the long run. Rich shares his journ...

Episode 94: Why BRRRRs Create Wealth But Don't Grow It (The ROE Problem)

2026-01-0132:14

What if the strategy everyone praises for building wealth is quietly slowing you down once you already have it? BRRRRs are powerful. They help you buy properties, recycle capital, and build serious equity. But here’s the uncomfortable truth most investors don’t talk about: once that equity stacks up, your money can actually start working against you. In this episode, Rich Lennon joins the show to break down why BRRRRs are great at creating wealth, but terrible at growing it long term. Rich sh...

Episode 93: I Don't Flip Houses - I Move Other People's Money (Here's How I Do It) - Andrew Lucas.

2025-12-2930:56

Most investors approach private capital from a position of need, believing money holds the power. In reality, the investor who can responsibly deploy capital is the most valuable person in the equation. In this episode, Andrew sits down with seasoned real estate investor and private money lender Rich Lennon to break down the mindset, mechanics, and real-world strategies behind raising and using private capital. From finding your first lender to structuring terms responsibly, Rich shares over ...

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