Generational Gains

Greg Herlean
  • 5.0 (8)
  • Entrepreneurship
  • Updated Biweekly

Welcome to Generational Gains - where two perspectives, seasoned experience, and youthful ambition, come together to offer an enriching blend of insights. Dive deep into the world of entrepreneurship, real estate, and personal growth with father-son power duo, Greg and Carson Herlean.Greg, with an astonishing track record of transacting over $1 billion in real estate and the founder of Horizon Trust, brings wisdom from years of steering people towards taking charge of their retirement through smart financial strategies. His expertise in self-directing IRAs and retirement accounts is unparalleled.On the other hand, his prodigious son Carson, all of 20 years old, is not far behind. Having built businesses that already boasts multiple six-figure revenues, he embodies the spirit of young entrepreneurship and the limitless potential of the new generation.Generational Gains is more than just a business podcast. It's a treasure trove of experiences, from the trials and triumphs of a seasoned entrepreneur to the fresh challenges and innovative solutions from a young mogul-in-the-making. Together, they delve into the art of setting transformative goals, maneuvering through life's challenges, boosting one’s income, and fostering a growth mindset that drives success in both life and business.Tune in for their heartwarming anecdotes and actionable advice. Whether you're a budding entrepreneur, an established business owner, or someone looking for a spark of motivation, Generational Gains promises a journey of continuous learning, self-improvement, and inspiration. Embark on this entrepreneurial voyage with the Herleans and discover the secret sauce to building generational wealth and wisdom.

  1. 9h ago

    Is College Still Worth It in the Age of AI? The American Dream Is Changing | Episode 48

    AI is changing the way we learn, work, build businesses, and potentially even how we define success. In Episode 48 of Generational Gains, Greg and Carson Herlean debate what they would do if they were 20 years old today with artificial intelligence at their fingertips, and whether the traditional path of college, a career, buying a home, and building the “American Dream” still makes sense. They explore the line between using AI as a powerful tool and using it as a shortcut. Can AI make you dramatically more productive and creative, or are people becoming dependent on it and losing the ability to think for themselves? The conversation then turns to one of the biggest questions facing young people today: Is college still worth it? Greg and Carson discuss why experience, relationships, real-world skills, entrepreneurship, and the ability to use AI may increasingly matter just as much, or more, than a traditional degree in many careers. In this episode: • How Greg is implementing AI inside his business • Whether AI makes us smarter or lazier • Why the people who master AI could have a massive advantage • How AI is already changing education • Whether spending four years in college still makes sense • College vs. entrepreneurship and real-world experience • Why hustle still matters even with AI • How hiring could change in an AI-driven economy • Whether the traditional American Dream is becoming harder to achieve • Why every path to success still requires time, sacrifice, and failure AI may make things faster, but Greg and Carson argue that it doesn’t eliminate the need to work, learn, take risks, and actually apply what you know. As Greg puts it, the people who combine AI with relentless execution could end up miles ahead of everyone who refuses to adapt. Subscribe to Generational Gains for conversations about money, entrepreneurship, business, investing, family, and building wealth across generations. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  2. Jul 27

    The Economy Is Getting Worse... Should You Find a Business Partner? | Generational Gains Ep. 47

    The economy has slowed, real estate investors are feeling the pressure, and many business owners are searching for ways to free up cash flow and survive the next six to twelve months. In Episode 47 of Generational Gains, Greg and Carson Herlean discuss what they are currently seeing in the real estate market, why fix-and-flip margins have become increasingly difficult, and how strategies such as velocity banking may help some people manage debt and cash flow more efficiently. They also explore one of the biggest decisions an entrepreneur can make: choosing a business partner. A strong partnership can provide capital, clients, expertise, accountability, and the missing skill set needed to grow. The wrong partnership can create resentment, financial losses, and a painful business breakup. Greg shares lessons from decades of partnerships, including why you should test a working relationship before committing, choose someone whose strengths complement your weaknesses, listen to trusted mentors and your spouse, and avoid automatically splitting a company 50/50. This episode covers: • What Greg and Carson are currently seeing in the economy • Why real estate deals are taking longer and producing smaller margins • How velocity banking may improve cash-flow flexibility • When partnering with someone can help a struggling business • The warning signs of a bad business partnership • Why complementary skills matter more than friendship • How to test a partnership before making it official • Why taking action beats endlessly preparing Whether you are starting a company, navigating a difficult market, managing debt, or considering bringing on a partner, this conversation offers practical lessons from two generations of entrepreneurs. Subscribe to Generational Gains for conversations about money, business ownership, real estate, retirement, and building lasting family wealth. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  3. Jun 23

    The Retirement Risk No One Plans For | Generational Gains Ep. 46

    In Episode 46 of Generational Gains, Greg and Carson break down the biggest takeaways from their live webinar on retirement income planning and the strategy Carson calls the Volatility Buffer. Most people insure their car, home, and life — but never insure their retirement income. In this episode, they discuss why market volatility can destroy retirement income, how whole life insurance can be structured as a protected income buffer, why the traditional “just invest and withdraw” model may not be enough, and how this strategy can work alongside self-directed IRAs, real estate, and other assets. If you’re preparing for retirement or want more control over your income, this episode is for you. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  4. Apr 7

    The Truth About Business in 2026: What the Smartest Entrepreneurs Are Doing Right Now | Generational Gains Ep. 45

    In this episode of Generational Gains, Greg and Carson break down their biggest takeaways from a recent Boardroom mastermind with over 250 business owners from around the country. From real estate and lending to entrepreneurship, AI, profitability, and the economy, this conversation dives into what successful people are actually seeing behind the scenes right now. In this episode, we talk about: Why profitability is harder than most people thinkWhat business owners are really dealing with in today’s economyWhy many successful people are still feeling pressureHow tighter lending is affecting deals and growthWhy some investors are preparing for major buying opportunitiesWhat AI is already doing inside businesses right nowWhy learning AI may become one of the most important career moves you can makeThe importance of faith, values, and community during hard seasonsWhy talking to your kids about money early matters more than ever One of the biggest takeaways from this episode is simple: Even successful people are being forced to adapt. The market is changing. Lending is tighter. Profit is harder. And the people who win will be the ones who stay grounded, stay creative, and keep learning. If you’re a business owner, investor, entrepreneur, or someone trying to better understand where things are headed, this episode will give you real-world perspective from people in the trenches. Share this with someone building a business or trying to make smarter moves in this economy. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  5. Mar 18

    The Smarter Way to Invest in 2026 (Real Examples) | Generational Gains Ep. 44

    In this episode of Generational Gains, Carson and Greg break down real conversations with clients this week — and the biggest investing mistake they see over and over again: Going ALL-IN on one strategy Whether it’s stocks, crypto, real estate, or even alternative assets… most people swing too hard in one direction — and pay for it later. In this episode, we dive into: A real client with $800K in the stock market questioning what to do nextWhy going “all-in” (even on good investments) is riskyWho self-directed investing is actually for (and who it’s NOT for yet)The ideal investment allocation strategy most people missHow to balance:StocksReal estate / alternative assetsSafe, guaranteed assets (like life insurance)Why your strategy should change with your stage of lifeThe difference between accumulation vs protection vs income planning Key takeaway: Wealth isn’t built by picking the “perfect investment”… It’s built by creating the right mix of investments that can survive any market. Who this is for: You have $75K–$500K+ saved and want to invest smarterYou’re nervous about the market but don’t know what to doYou’ve been told to “just stay in the market” but it doesn’t feel rightYou want more control, diversification, and protection Want help building your own plan? Reach out and we can walk through your numbers and show you exactly how this could look for you. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  6. Feb 18

    How to Protect Your Retirement Income From Market Crashes (Volatility Buffer Explained) | Generational Gains Ep. 43

    In Episode 43 of Generational Gains, Greg and Carson break down one of the most overlooked parts of retirement planning: Most advisors help you climb the mountain (accumulation)… but almost nobody teaches you how to get back down safely (distribution). That’s where the SAFE Method comes in — a strategy that uses a volatility buffer so you can keep income steady in retirement without being forced to sell assets when the market is down. In this episode, we cover: The 2 phases of retirement: Accumulation vs DistributionWhy market volatility is the real retirement killerThe truth behind the 4% rule (and why it’s not as “safe” as people think)How newer research pushes that withdrawal rate closer to ~2.8–3%Why sequence-of-returns risk matters more than average returnsHow a SAFE account can let your growth assets recover during down yearsWhy whole life insurance can be used as a non-correlated, liquid, guaranteed bufferA simple example of how the SAFE Method can improve outcomes with the same savings The goal isn’t to “invest more.” It’s to allocate smarter — so your retirement income isn’t at the mercy of market timing. If you want to see what this looks like with your numbers, we can run the math and show you how a SAFE plan could fit into your retirement picture. Reach out to Carson to walk through it using your actual savings, timeline, and goals. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  7. 12/30/2025

    3 Years Into Infinite Banking: Real Policy Numbers Most People Never See | Generational Gains Ep. 42

    In Episode 42 of Generational Gains, Carson walks through a real client’s Infinite Banking policy — showing exactly how it looks 3 years in, how it was originally illustrated, and how it’s actually performing today. This is the part most people never see. Instead of theory or sales language, this episode breaks down: What a whole life policy looks like after the early yearsWhy Infinite Banking feels confusing in years 1–2What actually changes in Year 3 and beyondHow paid-up additions (PUAs) create liquidityWhy policy cash value begins growing faster than contributionsThe difference between guaranteed vs non-guaranteed valuesHow dividends, cash value, and death benefit really work togetherWhy Infinite Banking is a savings and banking system, not an investment You’ll also see: Projected vs actual cash value and death benefitWhy conservative illustrations often under-promiseHow this policy is already outperforming expectationsWhy banks fail — and insurance companies don’tHow to use policy loans without interrupting growth 💡 Key Insight: Once a policy matures past the early years, every new dollar you put in becomes immediately usable — while still compounding for life. This episode is especially valuable if: You already have a policy and want a refresherYou’re 1–3 years in and questioning the processYou want to see real numbers, not marketing slidesYou’re considering Infinite Banking but want proofWatch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

  8. 12/22/2025

    How I Built a Wealth System at 23 (My Real Story & Banking Strategy) | Generational Gains Ep. 41

    In Episode 41 of Generational Gains, Carson shares his full personal story — how he went from a middle-class upbringing, losing money in the stock market, and questioning the traditional path… to building a repeatable wealth system centered around business ownership, Infinite Banking, and real estate. This episode isn’t theory. It’s real life. You’ll hear: • Why Carson stopped investing in the stock market at 18 • How mentors like Chris Naugle and Justin Colby shaped his thinking • Why he dropped out of college to pursue financial education • How Infinite Banking became the foundation of his wealth strategy • Why life insurance is his primary capital reservoir • How he uses policy cash value to buy real estate • How this system creates tax efficiency, liquidity, and control • Why wealth is built through systems, not single investments This episode is meant to be a case study — proof that these strategies aren’t abstract ideas, but real tools used by real people building real lives. Core Lesson: Wealth isn’t built overnight. It’s built by creating a system that produces income, stores capital safely, and reinvests it intentionally over time. Have questions about Infinite Banking, starting a business, or building your own system? Reach out to Carson, he is happy to connect. Watch the full video episode on Greg's YouTube Channel here: https://www.youtube.com/@gregherlean Follow and connect with Greg on IG: https://www.instagram.com/gregherlean/ Check out Greg's website here: https://www.gregherlean.com/ Carson's IG: https://www.instagram.com/c.herlean/ Carson's TikTok: https://www.tiktok.com/@carsonherlean

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5
out of 5
8 Ratings

About

Welcome to Generational Gains - where two perspectives, seasoned experience, and youthful ambition, come together to offer an enriching blend of insights. Dive deep into the world of entrepreneurship, real estate, and personal growth with father-son power duo, Greg and Carson Herlean.Greg, with an astonishing track record of transacting over $1 billion in real estate and the founder of Horizon Trust, brings wisdom from years of steering people towards taking charge of their retirement through smart financial strategies. His expertise in self-directing IRAs and retirement accounts is unparalleled.On the other hand, his prodigious son Carson, all of 20 years old, is not far behind. Having built businesses that already boasts multiple six-figure revenues, he embodies the spirit of young entrepreneurship and the limitless potential of the new generation.Generational Gains is more than just a business podcast. It's a treasure trove of experiences, from the trials and triumphs of a seasoned entrepreneur to the fresh challenges and innovative solutions from a young mogul-in-the-making. Together, they delve into the art of setting transformative goals, maneuvering through life's challenges, boosting one’s income, and fostering a growth mindset that drives success in both life and business.Tune in for their heartwarming anecdotes and actionable advice. Whether you're a budding entrepreneur, an established business owner, or someone looking for a spark of motivation, Generational Gains promises a journey of continuous learning, self-improvement, and inspiration. Embark on this entrepreneurial voyage with the Herleans and discover the secret sauce to building generational wealth and wisdom.

Information

  • Creator
    Greg Herlean
  • Years Active
    2023 - 2026
  • Episodes
    48
  • Rating
    Clean
  • Copyright
    © 2026 Generational Gains
  • Show Website
    Generational Gains

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