About Tyler Woodall

I'm a serial entrepreneur from Anderson, South Carolina. I studied marketing at Clemson University, then spent the first part of my career in commercial insurance — building a book the hard way, through high-volume cold calls and door-to-door drop-ins.

The agency

In 2021 I founded The WIN Agency. By leaning hard on systems, documented processes and remote team members, we took it from zero to seven figures in under two years. I sold the agency in 2025.

What made that possible wasn't more hours. It was the realization during COVID that most of what an agency does every day — quoting, servicing, admin — could be documented and handed to a trained team working remotely. That became the foundation of everything I've built since.

Agency Aid and ScaleOps

In 2023 I launched Agency Aid to give other independent agency owners the same leverage: fully trained virtual insurance specialists who can quote home and auto, handle mortgagee changes, send COIs and keep the back office running. We've now staffed well over 200 agencies, and at our peak I was managing a team of more than 100 people across several countries.

ScaleOps is the company that grew around it. Today it's a marketing and automation platform for independent agencies — websites built for Google and AI search, Google Business Profile management, lead campaigns, and the automation that ties it together. I'm also a partner in Catalyst Insurance Partners, an agency we run as the live test bed for all of it.

40+ countries and a mountain

I've been to more than forty countries. Not on a sabbatical, and not after selling the company — most of it while running a business with a hundred-plus people on the payroll, from a laptop, in whatever time zone I happened to be in.

That's not a flex about hustle. It's the actual argument behind everything I build. If a business only works when you're sitting in the office watching it, you don't own a business. You own a job with a lot of extra risk attached. Documented processes and a trained remote team are what turn one into the other, and the proof is that the work kept running while I was somewhere with bad wifi.

The clearest version of that was Kilimanjaro. Six days up to Uhuru Peak at 19,341 feet, no signal, company still running. You find out quickly which of your systems are real and which ones were just you.

Tyler Woodall at the Uhuru Peak summit sign on Mount Kilimanjaro, Tanzania — Uhuru Peak — 19,341 ft. Kilimanjaro, Tanzania.

Tyler Woodall hiking up Mount Kilimanjaro wearing a SOW Project cap — Day three on the mountain, in a SOW Project cap.

Tyler Woodall inside a blue glacier ice cave in Iceland — Inside a glacier, Iceland.

Tyler Woodall in front of Zojo-ji temple in Tokyo, Japan — Zojo-ji temple, Tokyo.

Tyler Woodall in front of the Sagrada Familia in Barcelona, Spain — Sagrada Família, Barcelona.

Tyler Woodall under a stone pavilion on the waterfront in Split, Croatia — Waterfront, Split, Croatia.

Tyler Woodall on the city walls above the rooftops of Dubrovnik, Croatia — The city walls, Dubrovnik.

Tyler Woodall in Praça do Comércio, Lisbon, Portugal — Praça do Comércio, Lisbon.

Tyler Woodall recording a podcast interview in a studio — Recording Defining Success.

Defining success

The conversation I never get tired of is how people define success for themselves.

A few years into running the agency I had the thing I'd been chasing — the business ran without me, I had freedom, I was making real money, and I was not happy. So I went back through my life and asked which moments I'd actually call joyful. Almost none of them were about money. Most were moments of service: mission trips, building something that made someone else's life easier. Before the agency I'd run a clothing brand called The SOW Project that sent part of every sale to feed kids in South America. It never made much. It's still the thing I'm proudest of.

That's why I host Defining Success with Tyler Woodall — business owners, athletes and high performers on what success actually looks like behind the scenes, not the highlight reel. I've asked the question on four continents now, and the most interesting answer is how often people update it. Almost nobody defines success at forty the way they did at twenty-five, and the ones who seem happiest changed the definition on purpose rather than by accident.

I've also hosted Agency Shop Talk for the insurance industry, and I publish on YouTube and LinkedIn.

What I believe

Document it, then delegate it. The E-Myth changed how I run every business I touch.
Go after good business, not easy money. Start with the end in mind.
Don't tiptoe through life to arrive safely at death.

Want to talk? Find me on LinkedIn or through ScaleOps. If you host a podcast and want to argue about any of this, here's the press kit.