For those who know me, this may feel like an unexpected shift after 15 years in oil and gas. And trust me… I understand the skepticism.  But while oil and gas and insurance might seem worlds apart, they share a very common foundation—people and relationships.

From 2015 to 2020, I had the privilege of founding RigUp (now Workrise) and growing it from a two-person startup into a $3 billion company. We succeeded by recognizing the inherent value of relationships in oil and gas—and we won by enhancing them, not disrupting them. We gave independent contractors effective, practical tools that made their work safer, easier, and more profitable. We built a business, a brand, and a platform that empowered the "small guys"—we empowered the people who power our world. It was an incredible journey, and surprisingly, it shares deep similarities with the world of insurance.

“Ah, so you’re building RigUp for insurance?” Well, in a way, yes.

This time, however, I’m starting from a very different place, with one significant advantage—a decade of experience in running this playbook.

When I founded RigUp, I was fresh out of grad school. I’d never started or scaled a business; I hadn’t even managed a team. I truly had no idea what it would take to build something of that scale. But over the past decade, I’ve had the privilege of experiencing every phase of that journey. From a team of two in a closet to a global organization with over 500 employees and billions in revenue, I witnessed every milestone, every misstep, and developed a grounded understanding of what success entails.

RigUp was a phenomenal journey, and I have no regrets. But it should seem obvious that there are things I would do differently.

Knowing what I know today, we could have executed this playbook in half the time and with a fraction of the capital.

Lesson 1: Move more aggressively through zero to one.‍

We spent far too long struggling for traction. Most entrepreneurs do.  We needed credibility to secure meetings, and meetings to build credibility. We needed pilot partners to create a quality product and a quality product to attract pilot partners.  Our overarching vision was sound, but establishing initial momentum was a grind.

During my time at RigUp, I completed over 15 acquisitions, gaining critical access to markets, contracts, and relationships. Acquisitions proved to be a powerful lever for scaling—but we only turned to it after years of fighting for traction. In service-based sectors where acquisitions come with critical relationships and can be executed at reasonable multiples,  we should have used acquisitions as an entry point.  This would have cut the journey in half, and it would have been far more cost-effective than organic growth. Most importantly, this would have  accelerated our passage through the "zero to one" phase, fast-tracking growth and platform development.

Lesson 2: You don’t have to build it all yourself.‍

This is easier to say today than it was in 2015. Regardless, we relied heavily on first-party tooling from the onset. This was not only capital-intensive; it was slow and required ongoing maintenance, which continued to drain resources and agility.

Today, we have access to a remarkable range of AI tools and technologies that weren’t available back then. The resources needed to build a successful platform already exist. You can build a platform with a fraction of the first-party development – harnessing advanced solutions that are only getting better. This greatly reduces the upfront capital required and drastically improves speed to impact.

Lesson 3: Find the cultural balance between innovation and seasoned expertise.

When we started RigUp, we were the “tech kids” trying to change the face of oil and gas. This wasn’t a cultural playbook that was readily embraced, and I believe the same holds true for insurance. This journey, above all, is about people. Bringing the right talent into this venture isn’t just an advantage; it’s essential.

In an industry built on relationships, you must find the right balance of innovative operators eager to move quickly while also embracing the experience of industry veterans. Establishing a top-tier team from the onset is critical—innovative operators, industry veterans, and creative capital partners who believe in the coexistence of these archetypes.

So yes, I’m starting an insurance agency.

I’m going to start by acquiring exceptional agencies grounded in strong relationships—the backbone of this industry.

I’m going to integrate cutting-edge AI tools into a seamless platform for these agencies to operate off of—not to replace the human touch, but to amplify it.

I’m going to partner with people and capital providers who balance forward-thinking innovation with the trust and wisdom of tradition.

Equal Parts innovation and relationships. Equal Parts tradition and technology. Equal Parts ambition and experience.

So yea, for some, this might feel like a big shift from 15 years in oil and gas—but to me, it feels like I’ve done this before.

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- Witte