7 Go-to-Market Lessons from Building a $16M Captive Insurance Platform

7 Go-to-Market Lessons from Building a $16M Captive Insurance Platform

Your inbox is at zero. Nobody wants to take your meetings. You have conviction in your idea but no customers, no traction, and no proof. Most founders quit here. Cole Riccardi kept walking.

In a recent episode of Category Visionaries, Cole Riccardi, CEO and Founder of Authentic, shared how he went from “wandering in the desert” in late 2022 to building a captive insurance platform that’s raised 16 million dollars. His journey from investment firm analyst to insurtech founder offers seven tactical lessons for B2B founders navigating complex markets.

Lesson 1: Use Your Unique Seat to Spot Category-Creating Opportunities

Cole’s idea didn’t come from a customer discovery sprint or a market sizing exercise. It emerged from occupying a rare vantage point. “I was fortunate enough to spend six years at an investment firm called Aquiline, which focuses on financial services investing,” Cole explains. “And we had a number of vertical software companies that sold software and payment services to small businesses. And were trying to figure out how to offer an insurance product to these small businesses.”

Most people saw the problem—vertical software companies wanted to offer insurance but couldn’t make the economics work. Cole saw the solution because he had pattern recognition from two different worlds. His family member had formed a captive insurance program for horse farms. His investment firm was trying to crack embedded insurance. The combination created what he calls “the AHA moment for embedded insurance.”

The lesson isn’t to get lucky with family connections. It’s to recognize when you’re sitting in a unique position where you can see something others can’t. Your alpha comes from privileged exposure to problems and solutions that don’t typically intersect.

Lesson 2: Talk to 100 People Before You Build Anything Real

After deciding to start Authentic, Cole spent three to four months in conversation mode. No product, no pitch deck with fancy mockups—just conversations. “The first three to four months, it was really about talking to as many potential partners as humanly possible, trying to gather all of the potential customer feedback that I could potentially garner,” he shares.

He talked to franchisors, vertical software companies, and associations—anyone who touched groups of small businesses. The pitch was simple: if you had the infrastructure, would you start your own captive insurance program?

Here’s what made this work: “With each of those conversations, you learn one new thing every time, which compounds after your hundredth conversation and all of a sudden you’re pitching something that’s a little bit more of a real product.”

The compounding effect of customer conversations isn’t about validation. It’s about building a product in the market’s language, with the market’s priorities, solving the market’s actual problem. By conversation one hundred, Cole wasn’t pitching his idea anymore—he was pitching their idea back to them.

Lesson 3: Your First Customers Are in Your Pipeline Already

When Authentic finally had a working prototype, Cole didn’t need to generate new demand. “Immediately went back to the folks I had one or several meetings with and said, hey, you know that captive platform you were so excited about in theory? Well now it’s here and I’d love for you to sign a contract.”

Not everyone said yes, but the conversion rate was high enough to validate both the idea and the approach. Those early conversations weren’t just research—they were pipeline building disguised as customer development.

The tactical lesson: when you’re pre-product, every conversation should end with permission to follow up when you’re ready. Document who was excited, what specific problems they mentioned, and what would make them sign. Then build exactly that.

Lesson 4: In Small Markets, Product Quality Is Your Marketing Engine

Cole’s marketing philosophy breaks conventional B2B wisdom. No content machine, no ABM campaigns, no outbound SDR team. “My marketing philosophy as CEO is insurance is a relatively small space, insure tech I should say, and a lot of these different channels that we’re pitching, they all talk,” he explains.

The strategy is simple but requires exceptional execution: “If we just do such an incredible job with a small subset of customers and our product is really that great and creating that much value, that channel will hear about it.”

Five months after launch, it’s working. “We’re really excited to see kind of the word of mouth that’s been happening within these channels for the value that we’re creating for folks.”

This only works in markets with three characteristics: small enough that everyone talks, sophisticated enough to recognize real value, and concentrated enough that word travels fast. If your market has these traits, your marketing budget should go into product and customer success, not ads and content.

Lesson 5: Build for Recession, Scale in Recovery

When Cole started Authentic, the consensus was clear: terrible timing for insurtech. The 2018-2019 hype had evaporated, investors were bearish, and funding was tight. His response reveals a contrarian framework for thinking about market timing.

“I would rather build in a hard time and see if my business works then than build in a time where there’s a little bit more funny money around that can keep you afloat if your business maybe isn’t so great or the economics are upside down,” Cole argues. “If you’re building in a harder time, you find that out way faster.”

The logic is about opportunity cost: “Every Founder, there’s an opportunity cost to their time and their life, right? And so I’d love to find that out sooner than later.”

Building when capital is scarce and customers are cautious forces you to have real unit economics, genuine product-market fit, and actual customer pain. If your business works in a down market, it’ll thrive when conditions improve. If it doesn’t work, you find out faster and move on.

Lesson 6: Product Work Is Fundraising Work

Cole has a clear message for his team about fundraising: “The work we do right now is for fundraising, because if you build a great business and are able to tell a great story, then you will be able to raise money.”

This flips the typical founder approach. Most founders treat fundraising as a parallel track—build the business while also crafting the fundraising narrative. Cole sees them as the same thing. “If you’re able to go into fundraising meetings and show an awesome product and awesome traction, that will make it a successful fundraising process.”

The implication is radical: stop obsessing over fundraising strategy, deck design, and investor targeting. Instead, spend those nine to twelve months making your product awesome and your traction undeniable. “It’s the actual work, it’s the actual company building, and then it’s the CEO’s responsibility to make sure everyone can see all of the accomplishments and all of the traction in that month or a couple of months of fundraising.”

When Slow Ventures wrote the early check, they weren’t betting on a pitch deck. They saw conviction, domain expertise, and a founder who had spent six years in the space. The story sold itself because the work was real.

Lesson 7: Enterprise Efficiency Beats SMB Scale in Complex Markets

Authentic’s go-to-market model defies SaaS conventional wisdom. “We don’t need 500 customers to build a billion dollar company. We need maybe 20 to 60 of the right customers,” Cole notes.

This changes everything about how you build. No army of SDRs. No massive customer success team. No self-service onboarding funnel at launch. Instead, Cole is “shooting up market” to the largest vertical software companies, the mighty middle and above in franchise space, and large associations.

The company just hired a head of go-to-market for partner activation, not a VP of Sales to build an outbound machine. They’re building a self-service model for smaller customers, but that’s secondary to landing the big fish.

This model only works when three conditions are met: high enough ACV to justify enterprise sales motion, complex enough product that competitors can’t easily replicate, and concentrated enough market that you can actually reach the top 60 customers. If your market has these traits, going enterprise-first might be more efficient than the traditional bottoms-up SaaS playbook.

The Compounding Effect of Clear Thinking

Cole’s journey from zero to 16 million in funding wasn’t about growth hacks or viral loops. It was about clear thinking compounded over time. See something others can’t because of where you sit. Talk to enough people that you build the product in the market’s language. Turn those conversations into your first customers. Let product quality drive word-of-mouth in a small market. Build when it’s hard so you know it’s real. Make your work speak for itself in fundraising. And structure your GTM around the actual economics of your market, not the SaaS playbook everyone follows.

“I think everyone has a different strategy to fundraising,” Cole reflects, but the meta-strategy is universal: do the actual work, build something real, and make sure people can see it. Everything else is noise.