The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
Startups For the Rest of Us
28 minutes 45 seconds
2 months ago
Episode 777 | Why Retiring Might Be the Worst Goal for Entrepreneurs
What if the traditional dream of retirement is actually a trap for entrepreneurs?
In this episode, Rob Walling talks with Derek Coburn, author of Let’s Retire Retirement: How to Enjoy Life to the Fullest, to challenge the long-held belief that early retirement is the ultimate goal. They explore why many entrepreneurs feel unfulfilled after retiring and how shifting toward purpose-driven work can create more freedom, meaning, and longevity.
Topics we cover:
(2:17) – Why traditional retirement often leads to boredom and regret
(6:44) – How working longer can drastically reduce your savings burden
(11:05) – The power of $50K moments and appreciating time with loved ones
(17:03) – Prioritizing health and well-being as a long-term strategy
(21:42) – Smarter and more flexible alternatives to full retirement
Links from the Show:
MicroConf Europe – September 28–30 · Istanbul, Türkiye
TinySeed – Invest
Let’s Retire Retirement – Book on Amazon
Derek Coburn’s Website
Derek Coburn | LinkedIn
Derek Coburn (@cadredc) | X
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
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Startups For the Rest of Us
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
