Real Estate Educators Podcast with Kevin Amolsch

Hosted by Kevin Amolsch

Business Investing

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188

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Aug 2026

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About the show

We provide the real estate education you can build on. This podcast is unlike any I have seen where we not only focus on real estate investing but on the content creation behind it. We want to help real estate investors and real estate influencers build their wealth. Hosted on Ausha. See ausha.co/privacy-policy for more information.

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60 recent

August 19, 202642 min

Jackie Coffey - How NOT to Flip a House: Lessons Learned from 1,000+ Deals

Jackie Coffey's first house flip went about as badly as a flip could go. She hired one person to handle the entire renovation. Contractors took her money and disappeared. Materials were stolen from the property. She replaced things that didn't need replacing. And after all that work, she practically broke even. But she didn't quit. In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with Jackie Coffey, "The Happy Investor," to talk about the lessons she's learned through 22 years in real estate, more than 1,000 transactions, and helping more than 1,000 students with their own deals. Jackie shares how she got started at 21 years old while working three jobs and struggling financially, and how it took 202 phone calls to hard money lenders before someone finally said yes to her first deal. More importantly, she explains how those calls taught her to understand the numbers, speak the language of real estate, and stop treating every "no" as a failure. Kevin and Jackie break down some of the biggest fix-and-flip mistakes new investors make, including over-improving properties, choosing contractors based solely on price, paying contractors upfront, purchasing materials too early, and failing to take accountability when things go wrong. Jackie also shares one of the most important lessons from her career: you don't have to know everything before you start. You have to be willing to learn, take responsibility for your mistakes, and keep going. Whether you're preparing for your first flip or already have dozens under your belt, this episode is packed with practical lessons that could save you time, money, and plenty of headaches on your next project. TIMESTAMPS 00:00 - Starting real estate at 21 years old 05:30 - Overcoming the fear of getting started 08:15 - Finding her first fix-and-flip deal 16:20 - Learning how to talk to hard money lenders 23:20 - Why hard money can be so powerful for new investors 29:10 - Taking accountability when a flip goes wrong 34:45 - Why successful investors have to keep going 38:05 - How Not to Flip a House 40:40 - Jackie's pricing strategy for fix and flips Connect with Jackie Coffey Find Jackie across TikTok, Facebook, and Instagram as Jackie The Happy Investor . Visit JackieTheHappyInvestor.com to learn more about Jackie's book, How Not to Flip a House , her real estate investing course, and additional resources for investors. Learn more about Pine Financial Group at pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

August 12, 202648 min

Ryan Lee - Build a Real Estate Portfolio That Buys Back Your Time

Owning rental properties doesn't automatically create financial freedom. If managing those properties consumes all your time, you may have simply created another job. In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with real estate investor and educator Ryan Lee to talk about what it actually takes to use real estate to create more control over your money—and your time. Ryan shares how the 2008 financial crisis completely changed the way he thought about investing. After watching his 401(k) and brokerage accounts fall, he turned to real estate, only to discover another problem: owning rentals required far more time and effort than he expected. That realization pushed Ryan to build systems around acquisitions, property management, accountability, leverage, and liquidity. Today, his portfolio includes more than 50 single-family homes alongside passive investments and syndications. Kevin and Ryan also break down the four ways real estate can build wealth—appreciation, cash flow, tax benefits, and amortization—plus how Ryan balances leverage with liquidity and evaluates passive investments. They also discuss Ryan's "Passive Income Machine," the difference between financial security and financial independence, and why he believes taking ownership of your money is the first step toward taking ownership of your life. 00:00 - How the 2008 crash changed Ryan's financial plan 06:20 - Defining financial freedom as control over your time 12:15 - Real estate isn't freedom—the system creates freedom 18:50 - How lease options work 24:40 - How to hold property managers accountable 28:20 - The four pillars of real estate wealth 31:50 - Active real estate vs. passive syndications 35:10 - Financial security vs. financial independence 42:05 - Using real estate and the tax code to create income 45:15 - The "dependency economy" vs. taking ownership Connect with Ryan Lee Learn more about Ryan's approach to financial freedom and his book, Retire in 10 Years or Less , at RetireIn10Years.com . Ryan also shares that he can be found on social media as @TheRyanDLee . Learn more about Pine Financial Group at pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

August 5, 202645 min

Tony Bradshaw - The Wealth Mistakes Keeping Most People Broke

What's the difference between people who simply manage their money and those who build lasting wealth? In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with author, coach, and podcast host Tony Bradshaw to discuss the lessons he's learned after interviewing more than 150 self-made millionaires. Tony shares how spending 15 years working with Dave Ramsey gave him a strong financial foundation—but also why he eventually realized there was another level to building wealth. From real estate and risk management to leverage, diversification, and financial education, this conversation explores the mindset shifts that separate people who simply get by from those who create lasting financial freedom. They also discuss why real estate has created more millionaires than any other asset class, the importance of understanding risk, and why finding mentors and surrounding yourself with the right people can accelerate your success. Whether you're just starting your investing journey or looking to grow your portfolio, this episode offers practical lessons on building wealth that lasts. TIMESTAMPS 00:00 - From Dave Ramsey to real estate investing 06:42 - Buying beachfront rentals instead of long-term rentals 10:08 - The leverage lesson Tony wishes he knew sooner 19:10 - The biggest investing mistake Tony made 22:08 - Why understanding risk is critical to building wealth 28:15 - Dave Ramsey's greatest strength—and where investors need to grow 34:25 - Why real estate creates more millionaires than any other asset class 40:12 - Final advice: become a little better every day Connect with Tony Bradshaw: Website: TonyBradshaw.com Explore Tony's books, podcasts, coaching programs, and the Get Money Smart community to learn more about personal finance, wealth building, business strategy, and financial education. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

July 29, 202641 min

Joseph Hunike - The Property Management Mistakes That Cost Real Estate Investors Thousands

Buying a great investment property is only half the battle. Managing it well is what determines whether it becomes a wealth-building asset, or a financial headache. In this episode of the Real Estate Educators Podcast, Kevin Amolsch talks with Joseph Hunike, Principal at WinVest Management in Miami, Florida. Joseph shares how his company has grown quickly by taking over underperforming rental properties and transforming them into profitable investments through better communication, stronger systems, and disciplined property management. The conversation covers how to evaluate your property manager, why every investor should understand their property's P&L, how to identify distressed investment opportunities, and what today's Miami rental market can teach investors everywhere. Whether you own one rental or an entire portfolio, this episode offers practical advice on protecting your investment and maximizing long-term cash flow. TIMESTAMPS 00:00 - Meet Joseph Hunike 03:10 - Building a property management company from the ground up 12:18 - How poor property management destroys cash flow 15:05 - The importance of knowing your property's P&L 21:18 - Common mistakes with Section 8 tenants 24:08 - How to identify distressed investment opportunities 30:12 - Appreciation vs. cash flow in today's market 36:10 - Joseph's advice for choosing a property management company Connect with Joseph Hunike: Website: WinVestManagement.com Learn more about professional property management, multifamily operations, rental property optimization, and investment consulting in South Florida. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

July 22, 202646 min

Peter Skaggs - How to Build a Real Estate Portfolio That Survives Any Market

What if you bought your first rental property at the absolute peak of the 2007 housing market? Most investors would assume that deal was a disaster. For Peter Skaggs, it became one of the biggest lessons of his investing career. In this episode of the Real Estate Educators Podcast, Kevin Amolsch talks with Peter Skaggs, a mortgage professional with more than 20 years of experience and a real estate investor who has built a portfolio of more than 250 units. Peter explains why buying power, staying power, and growing power are the three keys to long-term success in real estate. He also shares why cash flow matters more than market timing, why he prefers 30-year fixed-rate financing, and how investors can build portfolios that survive market downturns instead of being forced to sell. They also discuss the differences between single-family rentals and multifamily investing, DSCR loans, interest rate strategy, and the simple framework Peter uses to analyze investment properties. Whether you're buying your first rental or refining a large portfolio, this episode is packed with practical investing advice. 00:00 - The family story that inspired Peter's investing journey 05:45 - From mortgage websites to a 20-year lending career 14:18 - Why cash flow helped Peter survive the housing crash 17:10 - Buying Power, Staying Power & Growing Power explained 23:12 - Single-family vs. multifamily investing 29:22 - DSCR loans vs. conventional financing 35:10 - How Peter analyzes investment properties in minutes 38:15 - Why liquidity is every investor's safety net 41:02 - The importance of mentorship in real estate investing Connect with Peter Skaggs: Website: InvestorLighthouse.com Use Peter's free Deal Analyzer to evaluate rental properties, compare financing scenarios, and learn his Buying Power, Staying Power, and Growing Power framework for building wealth through real estate. Learn more about Pine Financial Group: pinefinancialgroup.com 43:35 Peter's final advice for building long-term wealth Hosted on Ausha. See ausha.co/privacy-policy for more information.

July 15, 202644 min

Tim Kelly - The Truth About Financial Freedom That No One Talks About

Everyone talks about achieving financial freedom—but almost nobody talks about what happens after you get there. In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with former Navy rescue swimmer, multifamily investor, bestselling author, and high-performance coach Tim Kelly. Tim shares how house hacking with a VA loan sparked his investing journey, how mentorship helped him buy apartment buildings while still serving in the military, and why he walked away from a military pension to pursue financial freedom. But the conversation goes much deeper than real estate. Tim opens up about hitting financial freedom only to discover it didn't automatically create happiness. He shares the personal struggles that followed, how rebuilding his life changed his perspective, and why true freedom requires purpose, discipline, relationships, and personal growth—not just passive income. Whether you're just getting started in real estate or already building wealth, this episode is filled with practical investing advice and meaningful life lessons. TIMESTAMPS 00:00 - From Navy rescue swimmer to real estate investor 09:05 - Buying apartment buildings while serving in the military 12:18 - Why mentorship accelerated Tim's success 18:08 - Why most people stay stuck and never invest 28:05 - The surprising truth about financial freedom 38:20 - Clarity, energy, and courage: Tim's coaching philosophy Connect with Tim Kelly: Website: TheTimothyKelly.com Learn more about Tim's coaching programs, commercial real estate investing, leadership development, and transformational adventure retreats. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

July 8, 202640 min

Jens Nielsen - How to Scale Your Real Estate Business Without Burning Out

Buying your first rental property is exciting—but building a real estate business that actually scales is a completely different challenge. In this return appearance on the Real Estate Educators Podcast, Kevin Amolsch welcomes back Jens Nielsen to discuss what happens after you've bought your first few properties. Jens explains why investors need to stop thinking like owner-operators and start thinking like business owners. They dive into building the right team, outsourcing effectively, finding mentors, knowing when to hire employees, and creating systems that allow your business to grow without consuming your life. They also discuss today's real estate market, why many investors are struggling to make deals work, and how successful entrepreneurs stay focused despite economic uncertainty. Whether you're trying to buy your first investment property or scale to hundreds of units, this episode is full of practical advice for building a business that lasts. 00:00 - Meet returning guest Jens Nielsen 06:10 - Thinking like an investor instead of an operator 09:00 - Why your team determines your ability to scale 18:05 - When should you outsource vs. hire employees? 26:00 - The difference between core competencies and outsourced work 29:12 - Lessons from The Science of Scaling by Benjamin Hardy 32:18 - Knowing when it's time to walk away from a deal 35:15 - Jens' coaching philosophy and helping entrepreneurs grow Connect with Jens Nielsen: Website: JensNielsen.us Learn more about business coaching, real estate investing, leadership, and building systems that allow you to scale without sacrificing your time. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

June 10, 202617 min

The Biggest Lessons Real Estate Investors Need to Know from Season 6

What separates successful real estate investors from those who never get started? After six seasons of the Real Estate Educators Podcast, Kevin Amolsch is breaking down the biggest lessons, mistakes, and trends from conversations with investors, entrepreneurs, and industry experts. In this Season 6 recap episode, Kevin shares the common themes that kept coming up again and again—from why taking action is the biggest predictor of success to the underwriting mistakes that quietly destroy deals. He also dives into how investors are using AI to save time, improve decision-making, review documents, streamline operations, and create more efficient businesses. Plus, Kevin discusses why real estate will always be a people business and how relationships with tenants, contractors, vendors, and other investors can make the difference between struggling and scaling. If you want to become a better investor, avoid common mistakes, and prepare for where real estate is headed next, this episode is for you. TIMESTAMPS 00:00 - The #1 mistake real estate investors keep making 05:02 - The importance of keeping consistent income while building wealth 09:05 - How AI is changing real estate investing 13:10 - Building the right team of vendors and contractors Learn more about Pine Financial Group: pinefinancialgroup.com Subscribe to the Real Estate Educators Podcast for more conversations about real estate investing, market trends, financing strategies, and building long-term wealth. Hosted on Ausha. See ausha.co/privacy-policy for more information.

June 4, 202636 min

Benjamin Stef - The Lending Strategies Real Estate Investors Are Using in 2026

Most investors focus on finding the next deal—but the way you structure your financing can make or break your ability to scale. In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with Benjamin Stef to discuss creative lending strategies, DSCR loans, HELOCs, building momentum, and what separates successful investors from those who quit. Ben shares how growing up in an entrepreneurial real estate family shaped the way he thinks about investing and lending. After starting his lending career during COVID and surviving one of the toughest interest rate shifts in history, Ben explains why focusing on the right daily activities and avoiding “shiny object syndrome” are critical for long-term success. They also break down creative financing options investors may not know exist—including DSCR loans, investor HELOCs, non-QM lending, and strategies to access capital without selling properties or giving up low interest rates. If you’re looking to grow your portfolio, unlock equity, or understand how successful investors think about financing, this episode is packed with valuable insights. TIMESTAMPS 00:00 - Growing up around real estate and entrepreneurship 07:05 - Starting a lending career during COVID 09:24 - Surviving the interest rate shift when others quit 18:04 - Finding your “why” and refusing to quit 20:40 What is non-QM lending? 24:45 - Hosting events and building relationships through education 29:15 - Why every investor needs to pick a niche Connect with Benjamin Stef: YouTube: Funding Freedom – Ben Stef Website: FundingFreedom.net Learn more about creative financing, DSCR loans, investor lending strategies, and ways to leverage equity to grow your real estate portfolio. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.

May 27, 202638 min

Jason Roberts - The Real Truth About Fix & Flipping in Today’s Market

Can you really make six figures on a single house flip, even in a challenging market? In this episode of the Real Estate Educators Podcast, Kevin Amolsch sits down with Jason Roberts to talk about wholesaling, fix-and-flipping, market risk, mentorship, and building a recession-resistant real estate business. Jason shares how watching his parents lose everything during the 2007–2008 housing crash shaped the way he approaches investing today. They discuss why investors need multiple streams of income, how to stress test deals, and why wholesaling creates the cash flow needed to survive market downturns. They also dive into double closings, finding off-market deals, probate opportunities, and how Jason’s mentorship students are landing six-figure flips. If you’re interested in wholesaling, flipping houses, or building long-term wealth through real estate, this episode is packed with practical advice. TIMESTAMPS 00:00 - Growing up in a real estate family in New York 09:05 - From engineering to real estate investing 11:14 - How fix-and-flipping replaced Jason’s W-2 income 13:28 - The biggest lesson from the 2008 housing crash 18:08 - The balance between staying focused and diversifying 22:18 - How Jason finds off-market wholesale deals 26:40 - What a “double close” actually means 31:45 - Scaling from one flip to 20+ projects per year 34:18 - The mentorship program helping students land six-figure flips 43:08 - Why market data matters more than opinions Connect with Jason Roberts: Website: BetterBlueprintAcademy.com Learn more about wholesaling, fix-and-flipping, and real estate mentorship opportunities in Colorado and nationwide. Learn more about Pine Financial Group: pinefinancialgroup.com Hosted on Ausha. See ausha.co/privacy-policy for more information.