Ever wonder how a CEO goes from managing 2,000 apartments to building multiple seven-figure ventures backed by private equity?

If you’ve ever struggled with scaling a service business, finding reliable vendors, or wondered how to make the leap from bootstrapping to private equity funding, this episode will feel like it’s speaking directly to you. Tyler Dunagin shares the real story of how he solved a problem most property managers know all too well and turned it into a rapidly growing portfolio of companies.

Here’s what you’ll take away from this conversation:

• How to create a focused business model in a crowded industry that instantly speaks to your ideal clients.

• The step-by-step reality of moving from self-funding to securing private equity while keeping control of your business.

• What really works (and what doesn’t) when acquiring companies and integrating teams into your growing portfolio.

Hit play now to learn Tyler’s hard-earned lessons—and discover strategies you can use to scale smarter and faster in your own business.

Starting & Scaling in Property Management

[00:00 – 04:30]
Tyler Dunnagan shares his journey from managing 2,000 apartments and $250M in assets to founding businesses that solved the exact vendor and turnover problems he faced.

[04:30 – 09:00]
He explains the challenge of turnovers at scale—why managing hundreds or thousands of units requires a completely different business model than small, local contractors can provide.

[09:00 – 14:00]
Tyler breaks down his “secret sauce”: laser focus on the multi-family housing niche, processes designed for speed (days, not weeks), and speaking the language of property managers.

[14:00 – 19:00]
Discussion shifts to workforce models—how his companies balance W2 employees with 1099 contractors to scale labor flexibly across seasons and geographies.

[19:00 – 24:00]
The story of how Tyler strategically bought high-value, highly specific domains (like “Painter” and “Flooring” names) that gave his businesses instant clarity and discoverability online.

Funding, Acquisitions & Lessons in Growth with Private Equity

[24:00 – 29:00]
Tyler shares how he funded his first business by cashing out his 401k, then grew through reinvestment, early friends-and-family support, and eventually landed private equity backing.

[29:00 – 34:00]
He explains the private equity deal structure—selling a minority stake with majority control provisions—and how it gave him growth capital without losing his leadership role.

[34:00 – 39:00]
The conversation digs into acquisitions: how Tyler integrates smaller companies, manages cultural alignment, and motivates teams with upside opportunities like phantom equity.

[39:00 – 44:00]
Key lessons on what to do (and not to do) in acquisitions: stay open-minded, align on goals, prepare for curveballs, and build strong 30-60-90 day plans for integration.

[44:00 – 50:00]
Tyler reflects on lessons learned—investing in untapped talent, using psychological profiling tools like “Perception Analysis,” and staying flexible as the company scales nationwide.

About Our Guest

At the crossroads of innovation and leadership, Tyler Dunagin founded and scaled multiple seven-figure ventures, consistently driving industry transformation.

Over the past decade, he started and expanded both service and product-based companies, notably Turnserv—a platform of self-started brands revolutionizing the housing sector by streamlining turnover processes. With operations extending to new locations every few weeks, Turnserv addresses critical operational challenges for property managers with unparalleled reliability and efficiency.