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Firsthand insights into achieving financial freedom through the dynamic realm of real estate investment. 

Flipping Houses: The Journey From Side Hustle to Sustainable Business - By Dustin Olverson

Aug 07, 2025

Hey everyone,

I wanted to dive into something a lot of us are extremelyr passionate about: real estate flipping. It's an exciting world, full of potential and prosperity, but as I've learned firsthand, it's also a journey with its own set of challenges. Over the years, I've worked hard to build systems and processes that not only helped my business grow but also kept me from burning out. I want to share a roadmap that I've seen play out—a way to think about your growth so that you can build a business that's not just profitable but also sustainable.

 

The Different Stages of Flipping

I see the journey of a real estate flipper in a few key stages. We all start somewhere, and the key is to understand what each level demands.

 

1-5 Houses a Year: The Solo Venture

This is where many of us begin. Flipping 1 to 5 houses a year is absolutely doable on your own. It’s a hands-on approach where you're often managing every detail yourself. You can definitely make money this way, and it’s a huge thrill. However, this model can be tough to sustain. You're constantly on the hunt for the next deal, and the stress of a limited inventory can quickly turn that initial excitement into a grind. The danger here is burnout—it's a real thing, and it can stop you in your tracks.

 

6-11 Projects: The Need for Support

When you start moving into the 6 to 11 house-a-year range, the game changes. You can’t do it all yourself anymore. This is where a project manager becomes a total game-changer. Bringing someone in to help with the day-to-day allows you to juggle more projects and still aim for those solid returns. This strategy allows you to juggle more projects while still targeting a return of 15% or better using hard and private money. At this stage, you might be thinking about quitting your day job, but I’d advise holding on for a bit longer. That steady income is a valuable safety net while you're still building your footing.

 

12-24 Properties: The Business Perspective

Now you're not just flipping houses—you're flipping money. When you get to 12 to 24 properties a year, your operation starts to look like a full-blown business. Your returns might level off a bit, but your volume is what drives your income. Quitting your day job is a real possibility, but it comes with a whole new set of responsibilities. You’ll be wearing the hats of financial manager, marketer, and strategic planner, all while leading a team. It’s no longer just about the projects; it’s about the business itself.

 

25-40+ Projects: Business Ownership and Beyond

Reaching this level means you are deep in the business. Your team is specialized, your systems are in place, and you might even be looking into fund ownership or larger development projects. You've achieved a lot, but this is also the point where you might realize you're still working incredibly long hours. It can feel like a new version of the rat race, but with a lot more complexity. The key to this stage is to remember your "why" and to keep your focus on building a legacy, not just a job for yourself.

 

Finding Purpose in the Process

The real secret to success in this business isn't just about the number of houses you flip. It's about building a sustainable approach that supports your financial goals, your mental health, and your relationships. I've learned that investing in a great team, building rock-solid systems, and committing to personal growth are just as important as finding the next deal.

Flipping houses doesn't have to be a frantic race to the finish line. It’s about building a smart, balanced business that gives you both the financial and time freedom you’re working so hard for. Use these stages as a guide, but remember to always find your own path that fits your unique strengths and your goals. The growth and lessons you learn along the way are what truly make this journey worthwhile.

We can achieve so much more when we work together and share our experiences. Let’s keep this conversation going! I'd love to invite you to one of my local networking events where we can talk more about the strategies that have helped me.

 

Let's work together to make those opportunities come knocking!

 

Together, we can build more than just houses; we can build the future!

 

Sincerely, 

 

Dustin Olverson 

Agent Investor, Volume Flipper, Branch Owner, Franchise Owner

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