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 journey from engineer to investor, the mistakes he made early on, and the exact mindset shift that helped him stop chasing deals and start letting money work for him. If you’ve ever felt burned out by flipping, overwhelmed by scaling, or curious about private lending but unsure where to start, this conversation will hit home.

You’ll Learn How To:

• Shift from active flipping to a more passive lending model
• Use other people’s money the right way to scale responsibly
• Build trust so capital starts finding you
• Avoid early mistakes that slow most investors down
• Think long-term instead of chasing quick wins

Who This Episode Is For:

• Investors burned out by flips and rehabs
• Real estate operators curious about private lending
• Professionals with capital who want smarter returns
• Anyone who wants more freedom without leaving real estate

Why You Should Listen:

Most investors never stop to ask if the model they’re using actually supports the life they want. Rich did, and it changed everything. This episode is an honest look at what happens when you stop trying to do it all yourself and start playing a smarter game. No sales pitch. Just real talk, real stories, and lessons you can actually use.

What You’ll Learn in This Episode:

• [00:00] Rich’s background and how he got into real estate
• [06:00] Why hard work alone doesn’t always lead to freedom
• [12:00] The biggest mistakes he made early on
• [18:00] How relationships, not deals, unlock capital
• [23:00] Why lending became the ultimate leverage play
• [30:00] The mindset shift that changed everything

Follow Rich Lennon:

Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

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 shares his personal journey from owning a large rental portfolio to stepping away from rehabs entirely and focusing on lending instead. The reason? Return on equity.

You’ll Learn How To:

• Understand the difference between building wealth and growing wealth
• Spot when your return on equity is quietly shrinking
• See why infinite returns don’t last forever
• Reposition equity without selling everything
• Use lending to make money work harder with less effort

Who This Episode Is For:

• BRRRR investors with growing equity but slowing returns
• Landlords who feel asset-rich but cash-stuck
• Investors are burned out on renovations and property management
• Anyone serious about scaling net worth, not just owning more doors

Why You Should Listen:
Most investors never realize when the game changes. This episode helps you see when it’s time to stop chasing more properties and start optimizing the money you already have. Rich breaks down return on equity in a way that actually makes sense, using real examples from his own portfolio so you can apply it to yours.

What You’ll Learn in This Episode:

• [00:00] Rich’s background and how he built his rental portfolio
• [05:00] Why BRRRRs are great early but flawed later
• [10:00] The return-on-equity trap most landlords fall into
• [14:00] How equity growth quietly lowers your returns
• [17:00] The moment Rich realized his portfolio was holding him back
• [21:00] Why lending changed everything
• [26:00] How to think like a money manager, not just a landlord

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

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 a decade of experience on both sides of the table, borrower and lender, and explains why the operator, not the money, is the true scarcity.

You’ll Learn How To:

• Shift your mindset so you stop chasing money and start attracting it
• Find private capital within your existing sphere of influence
• Talk about what you do without selling or sounding desperate
• Structure private money deals responsibly and professionally

Who This Episode Is For:

• New investors are unsure how to raise private capital
•  Experienced investors looking to scale with confidence
•  Real estate entrepreneurs want better funding options
• Anyone who feels uncomfortable asking others for money

Why You Should Listen:

Raising private capital isn’t about pitching; it’s about positioning. This episode breaks down why money is abundant, why skilled operators are rare, and how a simple mindset shift can completely change your ability to fund deals. Rich shares real stories, practical advice, and hard-earned lessons from both sides of the lending table.

What You’ll Learn in This Episode:

[00:00] Why money is abundant and skilled operators are the real scarcity

[02:57] How Rich found his first deal and built momentum early

[05:53] Scaling from one deal a year to multiple deals per month

[10:51] Defining success and knowing when to pivot

[16:33] Where private capital really comes from

[17:40] How to attract private lenders without asking

[24:05] Private money rates, terms, and how to negotiate

[27:42] Why beginners should use hard money before private capital

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

What if working harder isn’t the answer anymore? In 2020, Rich Lennon walked away from flipping houses, managing teams, and grinding every day, and didn’t look back. Instead of chasing deals, he chose a different seat at the table. The one where the money works, and life gets a lot simpler.

In this episode, Cody Hofhine sits down with Rich to talk about the exact shift that allowed him to stop flipping, start lending, and design a life around freedom, travel, and consistency. Rich breaks down how he moved from active investing to private lending, why being the bank changes everything, and how everyday investors can do the same without taking on unnecessary risk.

You’ll Learn How To:

• Know when it’s time to stop flipping and shift strategies
• Turn active income into passive returns
• Understand why lending can be the safest seat in real estate
• Earn strong returns without managing properties
• Build wealth without burning yourself out

Who This Episode Is For:

• Investors are tired of constant deal-chasing
• Flippers are wondering what the next phase looks like
• Business owners are sitting on cash and are unsure what to do with it
• Anyone who wants more freedom without risking their money

Why You Should Listen:
If you’ve ever wondered what comes after flipping houses, or how people actually reach financial freedom without chaos, this episode pulls back the curtain. Rich shares what worked, what didn’t, and the mindset shift that changed everything. 

What You’ll Learn in This Episode:

• [00:00] Why Rich shut down his flipping business in 2020
• [03:00] The moment he realized lending was the better play
• [07:00] How private lending really works in plain English
• [11:00] Why being the bank lowers risk, not raises it
• [15:00] The returns Rich targets and how he protects his capital
• [20:00] Who private lending is and isn’t for
• [26:00] How lending created freedom to travel and step back

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

Think your job is secure just because you’ve been there a long time? Think again. What’s happening across corporate America right now is a wake-up call for anyone still relying on a paycheck to fund their future. Loyalty doesn’t protect you. Tenure doesn’t protect you. And benefits disappear faster than most people expect.

In this episode, Rich Lennon breaks down why the traditional W-2 path is far more fragile than people realize, and what you can do before it’s too late. Using real-world examples, Rich explains why counting on a job for long-term security is risky, how companies actually make decisions, and the mindset shift that helped him take control of his financial future.

You’ll Learn How To:

• Understand why job security is mostly an illusion
• See the warning signs before layoffs and cuts happen
• Stop relying on one income source
• Think differently about retirement and long-term stability
• Start building income you actually control

Who This Episode Is For:

• W-2 employees worried about layoffs or job stability
• Professionals who feel behind on retirement
• Anyone who wants control over their financial future

Why You Should Listen:
If you’re counting on your job to always be there, this episode will challenge that belief in the best way. Rich keeps it real and walks through why building your own income streams matters now more than ever.

What You’ll Learn in This Episode:

• [00:00] Why recent corporate layoffs should concern every W-2 employee
• [01:30] The myth of long-term job security
• [03:00] How companies really think about payroll and profits
• [04:30] Why relying on one income source is dangerous
• [06:00] What taking control of your financial future actually looks like

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 money could work harder than you do, and you only had to put in a few hours a week? Sounds unrealistic, right? That’s exactly why most people miss this strategy.

In this episode, Rich Lennon joins Jay Conner on Raising Private Money to break down how Rich consistently earns 30–50% returns by arbitraging what he calls ‘lazy money’ no hype. No complicated systems. Just a simple, asset-backed approach that puts real estate and private lending together in a smart way.

Rich shares how he went from flipping hundreds of homes to lending millions, why he stopped buying houses altogether, and how he now focuses on growing money instead of managing properties. If you’ve ever felt burned out by active investing or are curious how private lenders really make their money, this episode pulls back the curtain.

You’ll Learn How To:

• Turn private money into consistent, high returns
• Structure deals where your downside risk is protected
• Earn lender-level profits without doing the rehab work
• Use real estate to grow retirement money faster
• Think like a money manager instead of a house flipper

Who This Episode Is For:

• Investors are tired of active flips and rentals
• Private lenders looking to increase returns safely
• Professionals with capital who want passive income
• Anyone curious how money-making really works

Why You Should Listen:

You don’t need more deals; you need a better model. This episode shows how shifting from operator to lender can dramatically improve your time, lifestyle, and returns. Rich explains it in plain English, with real numbers and real examples, so you can decide if this approach fits your goals.

What You’ll Learn in This Episode:

• [00:00] How Rich went from flipper to full-time lender
• [04:00] Why he stopped buying houses in 2020
• [07:00] How he underwrites deals in just a few hours
• [12:00] Using real estate, not people, to reduce risk
• [17:00] The simple math behind 30–50% returns
• [21:00] What ‘lazy money’ is and how it really works
• [26:00] Using self-directed IRAs to grow money faster

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

Follow Jay Conner here:

Website:https://www.jayconner.com/
YouTube: https://www.youtube.com/@raisingprivatemoneyrealestate
Facebook:https://www.facebook.com/jay.conner.marketing

Twitter: https://twitter.com/JayConner01

What if one trip could change the way you think, the way you invest, and the people you surround yourself with? Not through long lectures or packed conference rooms, but through real conversations, real relationships, and real breakthroughs.

In this episode, Rich Lennon shares why he’s taking entrepreneurs, investors, and go-getters to Mexico for a four-day mastermind that feels nothing like a seminar,  and everything like the experience that actually moves your business forward. From late-night strategy talks in swim-up suites to early-morning coffee with industry veterans, Rich breaks down exactly what makes this trip so valuable, and why the right environment can accelerate your growth faster than any course or classroom.

You’ll Learn How To:

• Build real relationships with investors, operators, and entrepreneurs doing big things
• Learn directly from experts through casual, small-group conversations
• Connect with both up-and-coming investors and seasoned gray hairs who’ve seen it all
• Spot the right business partners by watching how people interact off the clock
• Get clarity on marketing, operations, asset protection, and deal structure, without a classroom

Who This Episode Is For:

• Entrepreneurs who want to grow faster through the right relationships
• Investors are tired of traditional conferences that feel too formal and too scripted
• Anyone looking for a community of driven people who openly share what’s working

Why You Should Listen:

If you’ve ever wondered where high-level conversations really happen, this is it. Rich breaks down how these Mexico masterminds have shaped his career, helped him build lifelong friendships, and given him access to strategies he wouldn’t find anywhere else. You’ll walk away understanding why the environment matters, and why the right room can unlock the next level of your business and wealth.

What You’ll Learn in This Episode:

• [00:00] Why Rich chose Mexico and what makes this mastermind different
• [01:00] What the resort experience is really like
• [02:00] How the flexible schedule sparks real conversations and connection
• [03:00] Why younger investors bring fresh marketing and lead-gen insights
• [04:00] The gray hair wisdom that comes from seasoned operators
• [05:00] Why learning from people outside your market leads to total transparency
• [06:00] How casual dinners and downtime turn into real breakthroughs
• [07:00] What it costs, who should come, and how to bring a spouse or partner

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

Signing away liability has become the new tipping culture. Professionals often want your signature for their protection, not yours. Attorneys, vendors, and service providers push paperwork that shifts responsibility onto you. What happens when the people you pay refuse to be accountable?

In this episode, Rich shares a frustrating real estate closing that shows how common forced liability waivers have become. He explains how attorneys delayed funds, demanded unnecessary documents, and created extra hurdles even after the deed was recorded. Rich breaks down why these signatures matter, how they can strip your rights, and the red flags to watch for. He also covers lender and contractor scenarios, showing how to protect yourself from hidden liabilities.

You’ll Learn How To:

• Spot liability waivers that don’t benefit you
• Push back when attorneys or vendors demand unnecessary signatures
• Protect yourself during closings, payoffs, and lending transactions
• Identify documents that quietly strip your rights as a buyer, seller, or lender
   

Who This Episode Is For:

• Real estate investors navigating closings, contracts, and vendors
• Entrepreneurs looking to protect their rights in business transactions
• Anyone tired of signing documents without understanding the risks
• Buyers, sellers, and lenders who want to avoid getting boxed in by professionals
   

Why You Should Listen:
This episode uncovers how routine paperwork can quietly shift liability onto you. Rich shares real scenarios, breaks down hidden risks in common documents, and shows how to protect yourself from unnecessary signatures that cost you money and control.

What You’ll Learn in This Episode:

[00:00] Why liability waivers are frustrating 

[03:00] How a simple home sale turned into a mess of extra paperwork

[07:00] Why did both attorneys create delays, new demands, and more signatures

[10:00] What other liability-shifting documents should investors avoid

[13:00] Why certain contracts, assignments, and DSCR clauses can trap buyers and lenders

Follow Rich Lennon here:

Website: https://richlennon.com/

Facebook: https://www.facebook.com/rich.lennon.121

Instagram: https://www.instagram.com/richlennon92/

Think housing is already unaffordable? What if the changes coming next actually make things worse for the average buyer, but better for smart investors?

In this episode, Rich Lennon breaks down the biggest housing affordability shifts being discussed for 2026, including 50-year mortgages, portable loans, and even no-credit financing. He explains what these changes really mean for everyday buyers, why some of them are dangerous, and how investors can position themselves to win as the market reshapes. If you want to stay ahead instead of getting blindsided, this one’s a must.

You’ll Learn How To:

• Understand why 50-year mortgages sound good, but often trap buyers
• See how inflation, not interest rates, is the real housing problem
• Spot which affordability fixes are actually setting up the next crash
• Use market shifts to your advantage instead of fearing them
• Avoid getting stuck with a home you can’t sell later
   

Who This Episode Is For:

• Homebuyers worried about timing the market
• Investors who want to profit from market shifts
• Anyone confused by where housing is headed next
   

Why You Should Listen:

Housing rules are changing, whether you’re ready or not. This episode gives you clarity on what’s really happening behind the headlines so you can protect yourself, avoid bad moves, and spot real opportunity while others are guessing.

What You’ll Learn in This Episode:

• [00:00] Why housing affordability is being fixed the wrong way
• [02:30] How a 50-year mortgage really impacts your wealth
• [06:00] Why most buyers will get trapped by longer loans
• [08:30] The truth about portable mortgages and why banks fight them
• [11:30] Why no-credit loans should scare you
• [13:00] How today’s policies could trigger the next crash
• [14:30] What smart investors should be doing right now
   

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/

What do you do when the very thing you spent years building stops giving you the life you actually want? Most investors assume more doors equals more freedom, but sometimes it equals more stress, more risk, and more time away from the things that matter most.

In this episode, Rich continues the raw and honest breakdown of why he walked away from a massive rental portfolio he spent years building. From the hidden stress of managing dozens of doors to the financial traps investors overlook, this conversation digs into the real reasons he chose freedom, simplicity, and control over more.

You’ll Learn How To:

• Recognize the signs that your rental portfolio is controlling you
• Spot the hidden financial risks that come with scaling too fast
• Rebuild your investing strategy around lifestyle, time, and peace
• Avoid the burnout cycle that crushes most landlords
• Shift from managing chaos to creating stability and long-term wealth

Who This Episode Is For:

• Investors who feel overwhelmed by their rentals
• Anyone questioning whether scaling is actually improving their life
• Entrepreneurs are tired of stress-filled growth and are ready for real freedom

Why You Should Listen:

If you’ve ever felt the pressure to keep adding more doors, more deals, and more revenue, even when it’s costing you your peace, this episode will hit home. Rich opens up about the emotional and financial side of stepping back, simplifying, and rebuilding a business that supports your life instead of consuming it.

What You’ll Learn in This Episode:

[00:00] The moment Rich realized his portfolio wasn’t giving him the life he wanted [03:30] The real stress no one talks about when owning 100+ rentals
[07:45] Why profit on paper doesn’t always equal peace in real life
[12:10] The hidden costs that quietly eat away at cash-flowing properties
[16:30] How Rich decided what to sell, what to keep, and why
[20:55] Rebuilding a business around clarity, time, and lifestyle
[26:40] The complete mindset shift that changed everything
[31:15] What Rich Lennon is investing in now

Follow Rich Lennon here:
Website: https://richlennon.com/
Facebook: https://www.facebook.com/rich.lennon.121
Instagram: https://www.instagram.com/richlennon92/