Today we’d like to introduce you to Mike Wesling.
Hi Mike, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My family has been vacationing in Michigan for generations. As a kid, I always looked forward to our annual summer trips with grandparents, cousins, and everyone together under one roof. Those weeks created some of my favorite core memories.
Fast forward to 2007. I was newly married, and my wife Melissa and I joined my family on one of those Michigan vacations. On a bit of a whim, I decided I wanted to buy a home in South Haven, Michigan, as a place we could enjoy ourselves and also rent out to help cover costs. That first house became the start of something much bigger than I ever imagined.
After about five years of owning and managing that single home, demand was so strong that we decided to purchase another. A few years later, we expanded again by adding two more homes. Each step taught us more about what it takes to create great guest experiences while running vacation rentals effectively.
I had always dreamed of starting a professional property management company that could leverage what I’d learned from self-managing our homes and offer that same level of care to other homeowners. Around that time, my sister Emily was considering moving back to the Midwest from Arizona and making a career change. I had just read Who Not How, which is all about finding the right partners to help achieve big goals, and I knew Emily was the perfect “who.” I encouraged her to move to South Haven and help lead this new venture.
In 2023, we officially launched Anchor Point Vacation Rentals in South Haven, MI. My sister Emily is based in South Haven as our General Manager, and she’s doing an incredible job supporting both owners and guests. Our goal is to grow gradually, focusing on luxury properties with great owners who share our vision of creating the same unforgettable memories for other families that my own family has been making in Michigan for generations.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
No, it definitely hasn’t been perfectly smooth — entrepreneurship rarely is. It’s a challenging but deeply rewarding journey. We’ve faced our share of mistakes and obstacles, but each one has come with valuable lessons and opportunities to grow, both as a company and as individuals. When I look back at what we’ve built in just two years, I’m proud of the progress we’ve made as a small team. Most importantly, none of it would be possible without the trust of our owners and the continued support of our guests. They are truly the foundation of our success.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I continue to maintain an active role in enterprise technology sales at a Fortune 500 company, while Emily, Melissa, and the rest of our Anchor Point team manage the day-to-day operations. My background in technology has influenced the way we’ve built Anchor Point into a tech-forward organization. By bringing in tools such as SaaS platforms, automation, AI, and practices like disaster recovery and business continuity, we’ve been able to operate more efficiently and thoughtfully.
After nearly 25 years in sales, I’ve also come to deeply value long-term relationships, memorable experiences, and a strong personal brand — all of which carry over into how we serve our owners and guests.
One day, I’ll transition to focusing all of my attention on Anchor Point. For now, I feel fortunate to have such a capable team in place. Their leadership allows me to continue a technology sales career I enjoy, while still growing Anchor Point in the way we envisioned.
What was your favorite childhood memory?
Our annual family trips to Michigan hold some of my best memories. I have flashes of so many experiences — boating on Lake Michigan, climbing the dune at Holland State Park, getting $20 from my grandma to spend at the general store, the thrill of the Saugatuck Dune rides, and endless swims at the beach. I can still remember the smell of bacon in the mornings, the sound of my grandparents laughing, and swimming with my cousins and siblings without caring how cold the water was. Those moments are at the heart of why Michigan has always been so special to me.
Our family always stayed together in a vacation home rented from kind owners who opened their doors to others. For that week, we felt like we truly owned that beach house and were part of the community. That same feeling — of belonging, comfort, and connection — is what we strive to bring to every guest we have the privilege of hosting.
Contact Info:
- Website: https://www.AnchorPointVacations.com
- Instagram: https://www.instagram.com/anchorpointvaca/
- Facebook: https://www.facebook.com/anchorpointvaca
- LinkedIn: https://www.linkedin.com/in/mikewesling
- Youtube: https://www.youtube.com/channel/UCU6L4xhiT9yymF_yGiyk61g
