Growing the Money with Rich Lennon

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 mess this up, and why overpaying slightly can be smarter than underpaying. No loopholes. No gimmicks. Just practical thinking about cash flow, penalties, and using everyday expenses to your advantage.
You’ll Learn How To:
Avoid costly tax penalties that most people don’t see coming
Understand when extensions help, and when they don’t
Use credit cards strategically without going into debt
Turn unavoidable expenses into airline miles
Think about taxes like a money manager, not a victim
Who This Episode Is For:
Investors and business owners who want to be smarter with taxes
Anyone curious about airline miles and travel strategies
People are tired of tax season stress and surprises
Those looking for simple, practical money ideas that actually work
Why You Should Listen:
Taxes aren’t optional, but how you approach them is. This episode breaks down a realistic way to reduce friction, avoid mistakes, and make tax season a little less painful. Rich keeps it honest, practical, and grounded in real-life experience rather than theory.
What You’ll Learn in This Episode:
[00:00] Why so many people fear tax day, and why you don’t have to
[01:15] What filing an extension actually does, and doesn’t do
[02:45] The penalties and interest most people underestimate
[04:00] Why Rich prefers to overpay instead of underpay slightly
[05:10] The unpopular reason he pays taxes with credit cards
[06:30] How airline miles really work in plain English
[07:45] Using tax strategy to support long-term wealth building
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

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-employee operation doing 4–5 flips a month to lending out millions of dollars at 30–50% returns while working less than five hours per week. He covers how fractional lending works, why it outperforms traditional rentals from a return-on-equity standpoint, and how even passive lenders can earn double-digit returns secured by real assets.
You’ll Learn How To:
Build wealth through lending instead of operations
Structure fractional loans that return 30–50% on your own capital
Earn passive double-digit returns by backing borrowers safely
Protect lender money using notes, title policies, and builder’s risk insurance
Vet assets, underwrite borrowers, and enforce proper draw procedures
Raise private capital without pitching, selling, or sounding desperate

Who This Episode Is For:
Flippers and wholesalers who are hitting operational ceilings
Real estate investors looking to convert equity into higher returns
Private lenders seeking safer passive double-digit yields
Operators exploring alternatives to flipping, rentals, and syndications
Entrepreneurs who want time freedom without sacrificing wealth growth

Why You Should Listen:
This episode reveals a wealth strategy most investors only learn after burning out on flipping and rentals. It shows how to take money already earned from real estate and grow it faster, with less work and greater security. Rich breaks down how professional lenders generate asymmetric returns, how fractional models leverage other people’s capital, and why building wealth can look very different from making money.
What You’ll Learn in This Episode:
[00:00] Why Rich stopped flipping and pivoted to lending
[03:00] How fractional lending works and why lenders can earn 30%+
[07:00] How “Billy Bob” participates and earns passive double-digit returns
[10:00] How to underwrite deals: asset-first vs. borrower-first
[14:00] The two insurance policies lenders must require at closing
[18:00] How to protect capital using notes, mortgages, and draw controls
[24:00] How to raise private money without pitching or sounding desperate
[31:00] Who fractional lending benefits most, and when it makes sense to pivot
[38:00] Why experienced investors seek time freedom, not more flips
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92

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 how assuming low-interest loans and shifting toward lending can completely change the outcome.
You’ll Learn How To:
See why BRRRR deals that used to work now fall apart
Understand how interest rates flipped the numbers
Identify when refinancing hurts more than it helps
Use loan assumptions to improve cash flow dramatically
Think differently about rentals, notes, and lending
Who This Episode Is For:
BRRRR investors are struggling with today’s margins
Landlords with equity but shrinking cash flow
Investors are burned out on rehabs and property management
Anyone exploring private lending or note investing
Why You Should Listen:
Markets change. The best investors change with them. This episode helps you understand why BRRRR isn’t performing like it once did and what experienced investors are doing instead. Rich shares real examples so you can evaluate your own strategy with clearer expectations.
What You’ll Learn in This Episode:
[00:00] Why BRRRR worked so well in the past
[04:00] How rising prices and rates changed the math
[08:00] A real example of a BRRRR deal that now loses money
[12:00] Why refinancing is the weakest part of the strategy
[16:00] How assuming low-interest loans improves cash flow
[20:00] The difference between owning rentals and owning notes
[24:00] Why Rich shifted toward lending
[27:00] How to think about strategy changes moving forward
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

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 instead. Rich shares his personal shift away from owning and managing rentals and into private lending, not because he failed, but because the game changed.
You’ll Learn How To:
Spot when a once-great strategy has run its course
Understand why higher interest rates broke the BRRRR math
See how private lending fits into today’s market
Reduce stress while still earning strong returns
Think like a capital allocator, not just a property owner
Who This Episode Is For:
BRRRR investors are feeling squeezed by today’s market
Landlords are tired of rehabs, tenants, and surprises
Investors sitting on equity are unsure what to do next
Anyone open to smarter, simpler ways to grow wealth
Why You Should Listen:
Most investors keep running the same play long after the rules have changed. This episode helps you zoom out, rethink your approach, and understand why many experienced investors are shifting away from ownership and toward lending. It’s a practical, grounded look at what’s actually working right now.
What You’ll Learn in This Episode:
[00:00] Why BRRRR worked so well for so long
[03:30] How rising rates quietly changed the strategy
[07:00] The hidden risks most BRRRR investors overlook
[11:00] Rich’s personal turning point with rentals
[15:30] Why private lending started to make more sense
[19:30] Comparing ownership stress vs lending simplicity
[23:00] What smart investors are prioritizing today
[26:00] How to start thinking differently about your next move
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

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 triggering penalties or breaking the rules.
You’ll Learn How To:
Understand what checkbook control actually means
Move IRA money faster without waiting on custodian approvals
Decide between using a trust or an LLC
Avoid common mistakes that can trigger penalties
Use self-directed retirement funds for real estate the smart way
Who This Episode Is For:
Investors using or considering self-directed IRAs
Real estate investors who need speed to compete
Lenders are tired of custodian delays
Anyone who wants more control over retirement money
Why You Should Listen:
Speed matters in investing. This episode shows how experienced investors legally gain control of their IRA funds so they can act quickly, protect opportunities, and avoid costly delays. Rich walks through the process step by step, shares real-world examples, and explains the rules in a way that actually makes sense.
What You’ll Learn in This Episode:
[00:00] Why speed matters when using retirement money
[01:15] What checkbook control really means in simple terms
[02:45] The biggest problem with waiting on custodians
[04:00] How investors legally gain control of IRA funds
[05:45] Trust vs. LLC: which option makes sense for you
[07:30] How to avoid mistakes that trigger penalties
[09:00] When checkbook control is and isn’t the right move
[10:30] Final takeaways and who this strategy is best for
Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/