Think a high-return deal is always a golden opportunity? Sometimes the numbers are so tempting that you want to jump in fast, especially when everyone around you seems excited. But underneath those promises and pressure, some clues reveal whether an investment is solid or headed for disaster.

In this episode, Rich Lennon shares the five warning signs that helped his client avoid losing $200,000 in a deal that went completely to zero in just two months. He walks through how unrealistic returns, fuzzy math, group pressure, lack of security, and inexperience can quietly lead investors into terrible decisions. With clear examples and straightforward reasoning, Rich shows you how to evaluate opportunities and protect your money with real confidence.

You’ll Learn How To:

• Recognize when unrealistic returns point to deeper problems
• Check whether the math actually makes sense
• Avoid group pressure that pushes you toward high-risk decisions
• Understand why secured investments protect you better
• Lean on experienced investors to filter out dangerous deals

Who This Episode Is For:

• New investors learning to spot risky opportunities
• Private lenders evaluating deal security
• Anyone tempted by high return promises
• Listeners building confidence in investment decisions

Why You Should Listen:
This episode shows how a few simple checks can save you from losing six figures. Rich breaks down how to evaluate deals so you can protect your money and resist pressure. You'll invest from a position of real control and confidence.

What You’ll Learn in This Episode:

[00:00] Five warning signs that saved a client two hundred thousand

[02:00] Why would they need your money if returns are truly that high

[04:00] The danger of groupthink in investment decisions

[06:00] Surrounding yourself with experienced investors

[07:00] The bonus sixth factor, maintaining control of your money

08:00] The Zillow housing market downgrade and what it means for lending

Follow Rich Lennon here:

Website: https://richlennon.com/

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

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

Think a 12 percent loan really costs 12 percent? Think again. On paper, the numbers might look simple, but the way money moves tells a different story. The timing of payments, upfront points, and how interest is collected can quietly change your true rate of return or cost of borrowing. What happens when the math behind a 12 percent loan adds up to something much higher?

In this episode, Rich Lennon breaks down the hidden rate loan structures and how timing, points, and payment collection can dramatically affect yield. He walks through how to understand your true rate of return and spot when lenders are tweaking the numbers. With the right knowledge and transparency, you can gain a real advantage in the lending world. 

You’ll Learn How To:

• Spot how loan terms like prepaid interest and points change true ROI
• Calculate the internal rate of return (IRR) versus the stated annual interest
• Avoid being misled by “lower” advertised rates
• Use transparency as a competitive edge in lending deals
• Educate clients to build trust and long-term business
   

Who This Episode Is For:

• Private lenders who want to understand real returns on their loans
• Real estate investors are comparing lending options and hidden costs
• Borrowers seeking to avoid surprise fees and inflated interest rates
• Anyone who wants to make smarter lending and borrowing decisions
  
  

Why You Should Listen:
Behind every loan lies a story told by numbers. Rich Lennon shows how a few shifts in structure can raise a 12 percent loan to a 17.5 percent cost, and how knowing the math gives you the power to negotiate smarter, earn more, and lend with confidence.

What You’ll Learn in This Episode:

[00:00] Greetings from Orlando and the value of education

[01:00] How payment timing and points affect loan returns

[02:00] The risks of skipping payments and losing compounding

[04:00] What makes a 12% loan effectively cost 17.5%

[06:00] How educating clients reveals the true cost of borrowing

[08:00] The impact of transparency on trust and repeat business

Follow Rich Lennon here:

Website: https://richlennon.com/ 

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

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

Ever heard the saying, shirtsleeves to shirtsleeves in three generations? Sadly, it’s true, 95% of all wealth disappears by the third generation. The real reason? Most people spend their lives chasing wealth but never teach their kids how to build it, manage it, or respect it.

In this episode, Rich Lennon shares the personal story behind The Lennon Bank, a simple system he created to teach his kids about earning, saving, investing, and responsibility. From peanut butter sandwiches to horse races, Rich breaks down how small, consistent lessons at home can change your family’s financial future for generations.

You’ll Learn How To:

• Teach your kids real money habits without lectures or spreadsheets
• Turn everyday family routines into lessons about work and reward
• Build generational wealth that lasts long after you’re gone
• Use earned ownership to help your kids value what they buy
• Introduce financial lessons that stick, no fancy tools required
   

Who This Episode Is For:

• Parents who want to raise financially smart, grounded kids
• Families looking to break the cycle of spend it, lose it wealth
• Anyone serious about building a legacy that actually lasts
  
  

Why You Should Listen:
Wealth isn’t just about money; it’s about mindset, habits, and stewardship. This episode gives you a practical, heart-level way to start teaching financial wisdom in your own home. You’ll walk away with ideas you can use right away to help your kids and grandkids build confidence, independence, and a real understanding of value.

What You’ll Learn in This Episode:
[00:00] Why 95% of wealth disappears by the third generation
[01:00] The origin story of The Lennon Bank and what it teaches kids
[03:00] The simple $20-a-week system that builds money habits early
[05:00] How earning before spending changed Rich’s family dynamic
[07:00] What family vacations taught them about budgeting and priorities
[09:00] The surprising money lesson that came from a horse race
[10:00] How loss, choices, and ownership create lifelong financial wisdom
[11:00] The lasting impact of The Lennon Bank on generational wealth

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

What happens when the lending game changes overnight? Do you adapt fast enough to protect your money or get swept up with everyone else?

In this episode, Rich sits down with private lender and entrepreneur Scott Brown, who’s weathered multiple market cycles and built a thriving lending business from the ground up. From buying homes for $10,000 during the 2008 crash to structuring recession-proof loans today, Scott reveals how smart lenders survive, and even grow, when the economy shifts.

Whether you’re new to lending or managing millions, this episode will help you see market changes before they happen, protect your capital, and stay profitable when others panic.

You’ll Learn How To:

• Spot early warning signs that a market correction is coming
• Protect your capital by lending at the right loan-to-value ratios
• Use simple cash-flow principles to survive any downturn
• Structure loans that keep paying, even when property values drop
• Avoid the emotional traps that take lenders out of the game

Who This Episode Is For:

• Private lenders who want to lend safely and confidently in today’s market
• Investors who wish to learn from someone who’s been through every cycle
• Anyone who wants to build financial freedom through secure lending strategies

Why You Should Listen:

Markets always move, but with the right strategy, you can move faster. Scott’s real-world experience and timeless principles will provide you with clarity, confidence, and a clear roadmap for lending success, no matter what the economy does next.

What You’ll Learn in This Episode:

[00:00] The story of how Scott went from an orphaned kid to a seasoned investor
[02:30] Lessons learned from surviving multiple market cycles
[06:00] The warning signs that tell you a shift is already happening
[09:30] How to structure your loans for long-term safety and profit
[12:45] The biggest mistakes new lenders make in changing markets
[16:00] How cash flow, not appreciation, is your real safety net
[20:00] Why private lending still wins, even in uncertain times
[23:00] How to connect with Scott and start applying these strategies today

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

Think you can fund a flip without understanding construction? Think again. Most private lenders lose money not because they picked the wrong borrower, but because they underestimated the rehab. When you don’t understand what goes into a renovation, it’s easy to get blindsided by blown budgets, bad contractors, and projects that drag on for months.

In this episode, Rich Lennon sits down with Brandon Lindsey, founder of The Rehab Playbook, to break down what every private lender needs to know about construction. From how to spot red flags in a deal to understanding what $40 per square foot really means, Brandon shares practical ways to protect your money and fund flips like a pro.

You’ll Learn How To:

• Tell if a rehab budget actually makes sense
• Spot costly issues before they spiral
• Estimate light vs. full-gut rehabs fast
• Avoid funding hidden construction headaches
• Ask smart questions to protect your money

Who This Episode Is For:

• Private lenders who want to avoid funding bad rehab deals
• New investors who don’t understand construction risk but want to learn fast
• Anyone lending to flippers and looking for a repeatable way to verify deal safety

Why You Should Listen:
You don’t need to be a contractor to lend safely, but you do need to know what to look for. This episode gives you a clear, straightforward framework to evaluate renovation projects so you can lend confidently, avoid costly surprises, and build long-term wealth the smart way.

What You’ll Learn in This Episode:
 [00:00] The story behind Brandon’s start in construction and how it shaped his investing
 [03:00] Why understanding the scope of work is the difference between profit and loss
 [09:00] The real cost per square foot for cosmetic, heavy, and full-gut rehabs
 [13:00] How to identify big-ticket systems that blow up budgets
 [17:00] Foundation, mold, and waterproofing, how to catch problems early
 [19:00] The types of houses lenders should avoid funding and which ones are safest
 [23:00] How to spot bad contractors and the importance of trust and transparency
 [25:00] Why good communication and documentation protect both sides
 [27:00] Inside Brandon’s Rehab Playbook, how it’s helping investors and lenders win

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

Ever wondered how to grow your wealth without buying and selling another house? In this episode of Growing The Money, host Jack sits down with seasoned real estate investor and private money lender  Rich Lennon to talk about how he transitioned from flipping hundreds of homes to earning consistent, high returns through lending. Rich opens up about the biggest lessons he has learned, the lifestyle decisions behind his business pivot, and how you can safely create passive income by being the bank.

You’ll Learn How To:

• Transition from active investing to lending without sacrificing returns
• Build systems that protect both your capital and investor capital (‘lazy money’)
• Vet deals and borrowers like a pro, using simple underwriting principles
• Use private lending to generate up to 30% returns annually
• Teach financial literacy to your kids and build long-term wealth habits

Who This Episode Is For:

• Real estate investors looking to step back from flipping or rentals
• Professionals seeking a safer, high-yield investment option
• Parents interested in teaching their kids about money and responsibility
• Anyone who wants financial freedom without day-to-day management stress

Why You Should Listen:

Rich Lennon reveals the insider systems that helped him go from a hands-on flipper to a confident, high-return private lender. You’ll walk away with the knowledge and mindset to protect your capital, earn like a pro, and finally stop trading time for money.

What You’ll Learn in This Episode:

[01:06] How Rich got started in real estate after moving to Richmond, VA

[03:02] Why rental properties limit your wealth-building potential

[04:13] The lending model that earns 30% returns annually

[08:53] Rich’s biggest mistake — chasing software instead of staying focused

[13:40] Protecting investors and setting clear expectations with partners

[17:05] How to double your IRA each year until it hits $100K

[20:05] Teaching kids about money through the Lennon Bank system

[24:10] Rich’s top book and AI tools for smarter investing decisions

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

What if you could grow your retirement money completely tax-free, and still move fast enough to jump on real estate deals as they come? Most investors don’t realize that their IRA can actually slow them down, especially when custodians take days to release funds. But there’s a smarter, faster way to take control, without breaking any rules.  

In this episode, Rich Lennon breaks down the exact setup he uses to lend through his IRA without the frustrating custodian delays. You’ll learn how to structure your account, stay compliant, and unlock the freedom to move at the speed of opportunity. If you’ve ever missed out on a deal because the money wasn’t ready, this episode is for you.  

You’ll Learn How To:

• Set up a self-directed Roth IRA that grows your money tax-free  
• Bypass slow custodians while staying 100% compliant  
• Use a personal property trust to access funds faster  
• Avoid prohibited transactions that could cost you big  
• Build real wealth by lending through your IRA safely and strategically  

Who This Episode Is For:

• Private lenders who want faster control over their investment funds  
• Real estate investors are tired of waiting for custodians to release money  
• Anyone looking to make their retirement account work smarter, not slower  

Why You Should Listen:

Most investors let custodians control their timelines, but you don’t have to. This episode gives you a proven framework for keeping your money protected while freeing it from unnecessary bottlenecks. You’ll walk away knowing how to lend from your IRA safely, efficiently, and profitably, without ever waiting days for someone else’s approval.  

What You’ll Learn in This Episode:  

[00:00] Why custodians slow you down and how to fix it

[01:00] How to turn your IRA into a fast, flexible lending tool  

[03:00] The trust-based structure that keeps you compliant  

[05:00] How to transfer funds to a local bank account safely  

[07:00] The risks to avoid and the right way to stay protected  

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

Ever wonder how a small, overlooked lien could derail a real estate deal you thought was smooth sailing? Most investors and lenders assume that title insurance will catch everything, but mistakes happen, and the wrong policy could cost you thousands. 

In this episode, Rich Lennon breaks down how a lender’s title policy can protect you when homeowners’ policies fall short. He shares a true story where a 15-year-old lien threatened a property sale, but thanks to the lender’s policy, the borrower was saved from unnecessary costs. If you’re a lender or investor, this episode shows why the right title insurance can save you thousands.

You’ll Learn How To:  

• Understand the difference between homeowner’s and lender’s title policies
• Protect your investment from unexpected liens and title issues
• Use the lender’s policies to resolve mistakes made in previous closings
•  

Who This Episode Is For:  

• Real estate investors and private lenders want to protect their loans
• House flippers who want to avoid hidden liabilities
• Anyone concerned about minimizing risk and maximizing returns in property deals

Why You Should Listen:  

Most investors overlook the power of a lender’s title insurance until it’s too late. This episode demonstrates how a proper policy not only protects your investment but can also save thousands of dollars and prevent deal-breaking problems. Gain clarity, confidence, and tools to ensure your money is secure in every real estate transaction.

What You’ll Learn in This Episode:  

• [00:00] The key differences between homeowner and lender title policies
• [01:00] How lender title insurance protects the entire loan amount
• [02:00] A 15-year-old lien that almost blocked a property sale
• [03:00] Why unresponsive attorneys can create costly closing problems
• [04:00] How the lender’s policy saved the borrower $2,500
• [05:00] Importance of checks and balances in title insurance processes
• [06:00] Why title mistakes happen more often than most investors think
• [07:00] How to protect your deals with the right title policies

Follow Rich Lennon here:

Website: https://richlennon.com

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

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

Ever wonder why your payoff amount is higher than you expected, even when you close on time? The truth is, most borrowers and lenders are getting hit with hidden fees they don’t even know exist. Closing companies are quietly padding the bill, and it’s costing investors thousands in unnecessary interest.

In this episode, Rich Lennon exposes how closing companies’ internal mistakes and slow processes end up costing you real money, and what you can do to stop it. If you’re a lender, flipper, or real estate investor, this conversation could easily save you $1,500 or more on your next deal. Don’t miss this one, it’s time to reclaim your power and your profits.  

You’ll Learn How To:  

• Spot the hidden costs that closing companies never disclose  
• Avoid unnecessary interest charges that eat into your profits  
• Ask the right questions before closing to protect yourself  
• Understand how wiring delays and overnight checks quietly cost you money  
• Choose title companies that prioritize your money, not their convenience  

Who This Episode Is For:  

• Real estate investors and private lenders are tired of surprise closing costs  
• House flippers frustrated with delayed fund transfers  
• Anyone looking to protect their returns and take control of the closing process  

Why You Should Listen:  

Most investors lose money not because of bad deals, but because of small, hidden costs they don’t even notice. This episode reveals how to prevent that, giving you the clarity, confidence, and tools to make sure every dollar you earn actually ends up in your account.  

What You’ll Learn in This Episode:  

[00:00] Why hidden title company fees are quietly draining your profits  

[02:00] How delayed wires and overnight checks add costly interest days  

[05:00] The importance of asking payoff-through-date questions  

[07:00] Why most title companies don’t trust their own wire process  

[09:00] The $1,500 mistake that borrowers and lenders keep repeating  

[10:00] How to protect yourself and choose the right closing partners  

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

Ever feel like you’re almost ready to make your first private money loan, but something keeps holding you back? You’re not alone. Most investors never take that first step because they don’t have the right systems, people, and mindset in place.

In this episode, Rich Lennon breaks down the five essential things every new private lender needs before funding their first deal. These aren’t just theories; they’re the same steps his students use to confidently lend, protect their money, and earn 30%+ returns without sleepless nights.

 You’ll Learn How To:

• Understand your paperwork so you can lend with confidence
• Accurately determine property values before sending a single dollar
• Verify construction budgets and protect yourself from bad numbers
• Surround yourself with the right support, mentors, peers, and encouragers
• Develop the mindset and courage to finally hit send on your first loan
  
  

Who This Episode Is For:

• New investors who want to start lending but feel unsure where to begin
• Professionals are tired of watching their savings earn next to nothing
• Anyone who wants to build wealth safely while keeping full control of their money

 Why You Should Listen:

If you’ve been sitting on the sidelines waiting for the perfect time to start lending, this episode is your sign. You’ll walk away with a clear checklist of what to have in place, how to protect your money, and the confidence to make your first loan the right way, without fear or guesswork.

 What You’ll Learn in This Episode:

[00:00] Why most people hesitate before making their first loan
[01:00] The #1 confidence booster, understanding your paperwork
[02:00] How to evaluate the true value of a property and who to trust
[03:00] The key to confirming construction costs and avoiding surprises
[04:00] Why having the right circle makes or breaks new lenders
[05:00] The mindset shift needed to finally send your first wire
[07:00] How to connect with Rich for personalized guidance and next steps

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