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

EPISODE · Jul 21, 2025 · 20 MIN

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

from Generational Gains · host Greg Herlean

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 fastWhether 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/@gregherleanFollow 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

Episode metadata supplied by the publisher feed · Published Jul 21, 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 ch...

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

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