Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Released Monday, 21st July 2025
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Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Starting a Business in Your 20s vs 40s: What We Wish We Knew | Generational Gains Ep. 33

Monday, 21st July 2025
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What’s it really like to start a business in your 20s vs your 40s?


In this raw, real episode of Generational Gains, father-son duo Greg and Carson Herlean open up about the truth behind entrepreneurship—the freedom, the failures, and the myths social media doesn’t show you.


Together they explore:

✅ Why most people don’t know how to start a business

✅ What they misunderstood when they launched their first ventures

✅ The pros and cons of having a business partner

✅ How long-term thinking changes everything

✅ Why you need cash reserves (and peace of mind)

✅ The importance of failing forward—and learning fast


Whether you’re just thinking of launching a business or you’re years in and looking to regroup, this episode delivers hard-earned wisdom from both generations. You’ll leave with a grounded view of what it takes—and why the journey is worth it.


Subscribe for more weekly conversations on business, legacy, money, and life.

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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From The Podcast

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.

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