Wendell’s Weekly Wins and Whiffs

👋 Welcome to Wendell’s Weekly Wins & Whiffs — your front-row seat to the entrepreneurial and real estate rollercoaster, complete with high-fives, facepalms, and everything in between. Each week, I’ll peel back the curtain on life as an active investor and business builder: the triumphs that feel like victory laps, the flops that sting like a surprise plumbing leak, and the behind-the-scenes grind of running multiple companies. From flips that soar to admin headaches that test my patience, you’ll get the real, unfiltered scoop on both deals and business operations. Why? Because building wealth isn’t just about properties — it’s about building systems, partnerships, and businesses that can stand the test of time. My goal is to share the wins, the whiffs, and the lessons learned so you can sharpen your own edge in both investing and entrepreneurship.

Author

Wendell Butler
September 16, 2025

🏆 This Week’s Win — Unplugged in Corolla, NC
This week’s biggest win wasn’t about deals closed or units added — it was about stepping away. I took a long, much-needed vacation with my family in Corolla, NC, completely unplugged. No emails. No phone calls. Just sand, ocean, and time well spent together.

🌊 Why Unplugging Matters
It’s easy to get caught in the hustle of building businesses, chasing opportunities, and grinding toward bigger goals. But at the core of it all, the reason we work so hard isn’t just for money — it’s for freedom, presence, and time back in our lives.

💡 The Lesson
Success isn’t just measured by properties flipped or units acquired. It’s also measured by moments like these — when you can step away, be fully present, and enjoy the life you’re building. Taking the time to recharge reminds you why you’re putting in the work in the first place.

🔋 Coming Back Stronger
Now, with a clear mind and renewed energy, I’m ready to jump back into projects and opportunities with a fresh perspective. The vacation was a reminder that balance is essential — because when you take care of yourself and your family, your business benefits too.

💨 This Week’s Whiff — The Burnout Wake-Up Call
Truth be told, there wasn’t really a “whiff” this week — just some much-needed clarity. While unplugged on vacation in Corolla, NC, I had a few epiphanies about my business and how I’ve been running it.

📌 The realization?
I’ve been spending too much time in my business instead of on it. The day-to-day grind keeps me busy, but it doesn’t always push the company toward long-term growth. Even though I delegate quite a bit, I came to the conclusion that I need to take it further — hiring smarter, empowering my team more, and leveraging AI tools to free myself from the bottleneck role I’ve been playing.

✨ The silver lining…
The burnout I felt before vacation wasn’t a dead end — it was a wake-up call. Taking a step back gave me a fresh perspective: if I want to build this business the way I envision it, I need to shift from operator to architect. That means creating space to think bigger and lead more strategically.

🧭 The mindset?
Sometimes, the biggest “miss” isn’t a mistake — it’s realizing what needs to change. This week was about acknowledging that balance, delegation, and smarter systems aren’t luxuries; they’re necessities for scaling and sustaining. From here forward, I’m committed to stepping back, looking from the outside in, and building the business the right way.

🎯 Tactical Tip of the Week: Let AI Be Your Assistant
If you’re not using AI in your business today, you’re already falling behind. Tools like ChatGPT aren’t just “nice-to-haves” — they’re leverage. The tedious, repetitive, time-consuming tasks that eat up your hours can often be handled faster, cheaper, and more consistently with AI.

Here are a few practical ways to put this into action:

  • Content Creation: Draft blog posts, newsletters, social media captions, or even property listings in minutes. AI can give you a solid first draft so you’re never starting from a blank page.

  • Market Research: Summarize trends, competitor insights, or industry updates in seconds instead of spending hours searching and reading.

  • Admin Help: Use AI to draft emails, organize meeting notes, create checklists, or even build SOPs. It’s like having a junior assistant on call 24/7.

  • Data Crunching: Upload spreadsheets and let AI highlight key takeaways, trends, and red flags so you can make decisions faster.

  • Creative Brainstorming: From deal structures to marketing campaigns, AI can help you think outside the box and offer fresh ideas you might not have considered.

✨ The takeaway: AI won’t replace you — but it will replace the entrepreneurs who don’t use it. Start small, experiment, and you’ll quickly see how much more efficient (and effective) your business can be when AI is part of your toolkit.

🔦 FROM THE FIELD: Family Over Everything
At the end of the day, business, deals, and growth all matter — but nothing comes before family. That truth hit home this past week as I spent 8 days in Corolla, NC, one of the most remote parts of the Outer Banks. No commercial strips, no crowds — just the ocean, sand, and even wild horses wandering around our Airbnb.

I had the chance to step away and enjoy quality time with the people who matter most: my mom, dad, my sister and her husband, my girlfriend Catelin, and of course our dog, Presley. It wasn’t about productivity, emails, or projects — it was about being present.

💡 Why does this matter?
Family is the reason behind the hustle. The long hours, the late nights, the risks we take — all of it comes back to creating freedom, stability, and memories with the people we love. It’s easy to get so wrapped up in the grind that you forget the “why,” but time away in Corolla was a reminder that the ultimate ROI is time with family.

From the field, the lesson is simple: wins in business are temporary, but moments with family last forever.

📸 Catelin, Presley and I soaking it all in on the beach:

🎤 FINAL WORD

This week wasn’t just about getting away — it was about gaining perspective. Taking 8 days in Corolla, NC with my family reminded me of the why behind the grind: freedom, time, and presence with the people who matter most.

The win was unplugging and recharging. The “whiff” wasn’t a setback but an epiphany — realizing I’ve been too deep in the day-to-day of my business and need to step back, delegate more, hire smarter, and leverage tools like AI to truly scale. The tactical tip drove that home: if you’re not embracing systems and technology like ChatGPT, you’re working harder than you have to.

The lesson? Entrepreneurship isn’t just about building businesses — it’s about building lives. Wins give us momentum, reflections show us where to shift, and time away reminds us of the bigger picture.

Keep delegating, keep innovating, and most importantly, keep your “why” front and center. That’s how we build businesses that give us not just income, but freedom and time back in our lives.

Enjoy the journey,