👋 Welcome
I hope your week is off to a good start and you’re carving out time for the things that matter most.
This week’s story is about what happens when everything falls apart… and how that experience can actually become your greatest teacher about building something better. It’s a reminder that rebuilding is possible, but only if we build smarter the next time around.
If you're thinking about starting something new, this one’s for you.
Let’s keep turning ideas into action,
~ Curt
🌟 Words to Inspire
“Rock bottom became the solid foundation on which I rebuilt my life.”
— J.K. Rowling
Setbacks can feel like the end. But sometimes they clear the path for something wiser and more intentional. If you’ve come through a hard chapter, remember this: you’re not starting from scratch. You’re starting from experience.
📖 Main Feature
The Day I Lost Everything (And What It Taught Me About Risk)
At 46, my partner and I walked through a $1,000,000 custom home we couldn't sell for any price, one of several that would ultimately cost us everything. Ten years of hard work, a hundred custom homes built, multiple awards… and yet in less than two years, the 2008 crash took it all.
Jim and I thought we were the smart ones. We started our custom homebuilding company in 1998 with a bootstrap budget and a conservative mindset. We reinvested every dollar. We grew slowly, steadily. We didn't chase risky flips - we focused on quality and relationships. We believed experience would protect us.
But when the housing market collapsed, even caution wasn't enough.
Banks froze lending. Buyers vanished. Three speculative homes sat unfinished and unsold. We'd invested our life savings—every penny—trying to keep the doors open.
"Losing the business was brutal. But the real devastation was personal. I lost my home. My financial security. My future."
What saved me was time. At 46, I had two decades to rebuild. I rebuilt from scratch, leaning into what I knew, taking small wins, and staying in motion. Slowly, I recovered.
But what if I'd been 60? Or 65? Starting over wouldn’t have felt like an option; it would’ve felt like a crisis with no exit.
That's precisely why, when I officially launched Retirepreneur at 63, everything had to be different.
❌ No office
❌ No payroll
❌ No physical inventory
❌ No massive capital investment
It had to be digital. Lightweight. Flexible. Built to serve others without risking everything again.
Because I've lived through the financial free fall—and I'll do everything in my power to help you avoid it.
If you're planning a second-act business, start with this mindset:
✔️ Keep overhead low
✔️ Build around your experience
✔️ Don't bet the farm
✔️ Prioritize income stability over hype
I survived financial devastation once. At our age, we can't afford to do it again.
Build smart, not big.
p.s. oh, and Jimmy is still out there building beautiful homes and winning awards!
📣 Partner Spotlight
If you’re exploring remote or flexible work, there’s one platform that stands above the rest—FlexJobs. Unlike massive job boards that bury you in spam and scams, FlexJobs is curated, focused, and built for professionals looking for legitimate, flexible roles. Every listing is hand-screened, which means you can search with confidence and skip the nonsense.
Whether you’re interested in part-time work, freelance projects, or a new second-act career, FlexJobs makes the search easier and more efficient. With job titles ranging from virtual assistant to project manager, and industries like finance, healthcare, and customer service, there’s something for nearly every skillset and schedule.
Now is the perfect time to simplify your search and focus only on what’s real and relevant.
👉 Explore FlexJobs today and find work that fits your next chapter.
🧰 Weekly Resource
Curious what’s inside the Retirepreneur Hub? It’s a low-cost membership packed with practical tools for launching a small business or exploring flexible work, without the overwhelm.
This week, check out our newest addition: The Complete Consulting Services Guide, specifically designed for professionals 55+ ready to turn decades of experience into flexible income.
Explore everything the Hub has to offer and get inspired to take your next step.
Action Challenge
💥 Try This Before Next Tuesday
Take 15 minutes this week to honestly assess:
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How much can you afford to lose?
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How much time do you have to recover?
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What does 'safe' look like at your age?
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Can your business idea succeed without putting everything on the line?
A smart second act starts with clarity.
The goal isn’t just to start something, it’s to build something that fits your life now.
💡 Quick Tip
Start your morning with one 15-minute learning block - read one article, watch one tutorial, or listen to one podcast episode. Small daily inputs compound into expertise over time.
🛑 Parting Words
I hope this week’s newsletter reminded you that past setbacks don’t define your future—they inform your wisdom!
Take one step this week to align your goals with your reality. Build wisely, and keep moving forward.
Best wishes!
💁 That’s a Wrap
When you’re ready, here are ways that Retirepreneur can help:
🎓 Take the Free Course
Ready to turn your experience into income? Our free Retirepreneur Biz 101 course gives you the confidence, clarity, and step-by-step roadmap to start your second-act business with purpose.
🚀 Explore the Retirepreneur Hub
You don’t have to build your next chapter alone. The Retirepreneur Hub gives you access to step-by-step tools, trusted guidance, and practical resources to turn experience into income... at your pace, on your terms.
📝 Explore the Action Guides
Need help taking that next step? Our free Retirepreneur Action Guides give you simple, proven frameworks to move from dreaming to doing—on your terms and timeline.
📘 Read the Founder Story
Wondering if it’s too late to start? Read Curt’s journey from retirement to reinvention and discover how purpose and freedom are still possible at any age.
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