Authentic’s First 100 Conversations: How Cole Riccardi Turned Customer Discovery Into Pipeline

Most founders finish their hundredth customer conversation and think they’ve done research. Cole Riccardi finished his and had a waitlist.

In a recent episode of Category Visionaries, Cole Riccardi, CEO and Founder of Authentic, revealed how he spent late 2022 and early 2023 having conversations that looked like customer discovery but functioned as enterprise pipeline building. When Authentic launched its captive insurance platform, those conversations converted into paying customers. No cold outreach. No demand generation. Just a methodical approach to compounding learning while building qualified pipeline.

Here’s how he did it—and the framework you can replicate.

The Starting Point: Zero Inbox, Maximum Conviction

Late 2022, Cole left his role at Aquiline, an investment firm focused on financial services. He had identified a massive opportunity: vertical software companies, franchisors, and associations all wanted to offer insurance to their small business customers, but the economics of traditional partnerships didn’t work. His insight was that captive insurance—traditionally only available to large enterprises—could solve this if the infrastructure existed.

But insights don’t pay bills. “I think one of the most challenging parts of being an entrepreneur is when your inbox is zero and you don’t have meetings and nobody probably wants to talk to you, but you just need to kind of keep wandering in the direction that you believe is the right path,” Cole reflects.

He had no product, no prototype, no team. Just a thesis about captive insurance and a conviction that if he was right, these companies would buy. The question was how to validate that thesis while simultaneously building relationships that could convert later.

The Three-Channel Strategy

Cole identified three distinct channels where his solution could work: franchisors who could offer insurance to their franchise networks, vertical software companies trying to add insurance to their bundle, and associations looking for member value-adds. This wasn’t arbitrary—these were channels where he’d seen the pain firsthand during his years at Aquiline.

“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,” Cole explains. “And what that meant in practice was talking to as many franchisors, talking to as many vertical software companies, talking to a ton of associations.”

The pitch was disarmingly simple: if you had a platform or infrastructure, would you start your own captive insurance program and offer insurance to your small business customers or members?

Notice what he’s not asking: “Would you buy my product?” or “What features would you need?” He’s validating the category itself—whether these organizations even want to own their insurance distribution. If they don’t, no amount of product refinement matters.

The Compounding Learning Effect

Here’s where most founders get customer discovery wrong. They treat each conversation as an isolated data point—twenty conversations means twenty pieces of feedback. Cole understood something more powerful: conversations compound.

“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,” he notes.

This isn’t about validation. It’s about linguistic alignment. By conversation fifty, Cole was using the exact terminology his prospects used. He understood their objections before they raised them. He knew which features mattered and which were nice-to-haves. Most importantly, he was pitching the solution in their language, not his.

The compounding effect works because each conversation refines your understanding of the problem space. Conversation one teaches you about the problem. Conversation twenty teaches you about how different segments think about the problem. Conversation seventy teaches you about the unstated assumptions preventing them from solving it themselves.

By conversation one hundred, you’re not pitching a product—you’re articulating a solution they’ve been searching for but couldn’t name.

Building Pipeline Disguised as Research

The genius of Cole’s approach is that he never separated customer discovery from pipeline building. Every conversation that validated the thesis was also a potential customer being warmed up.

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.”

The conversion wasn’t perfect—not everyone who was excited said yes. But the hit rate was high enough that Authentic had customers from day one. “I was very pleased with the amount that were willing to move forward and take a chance on a startup, and I think that’s a credit to the idea,” Cole shares.

Think about what he avoided: no cold outreach when the product launched, no educating the market on why they need this, no convincing people there’s a problem. All of that work happened in the pre-product phase, disguised as customer conversations.

The Permission Strategy

Here’s the tactical detail most founders miss: Cole wasn’t just having conversations and hoping people remembered him. He was getting explicit permission to follow up.

The feedback was “overwhelmingly positive” during these early conversations. But Cole understood a crucial truth: “You never know if someone’s actually going to be a customer until you put a piece of paper in front of them and ask them to sign it.”

Positive feedback without commitment is validation theater. Cole needed something more concrete—permission to come back when he had something to show. Each conversation ended with an implicit agreement: if I build this, you’ll take another meeting.

That permission is what converted customer discovery into pipeline. Without it, he’d need to re-earn attention when launching. With it, he had a warm list of qualified prospects who were already bought into the vision.

The Timing Unlock

The other insight in Cole’s approach is timing. He didn’t rush to build and launch. He spent three to four months purely in conversation mode, learning and refining. This patience created two advantages.

First, by the time Authentic launched, Cole deeply understood the market. He knew which objections were real blockers versus nice-to-haves. He knew which segments had the most pain. He knew the exact words that resonated.

Second, he built credibility through consistency. The prospects he talked to in month one and then again in month three saw someone who was seriously pursuing this, not just exploring. That commitment signaled this wasn’t a side project—it was going to happen.

The Framework: How to Replicate This

Cole’s approach can be distilled into a repeatable framework:

Identify your channels. Who are the three to five distinct types of buyers for your solution? Be specific—not “enterprises” but “vertical software companies serving SMBs.”

Validate the category, not the product. Ask if they want to solve the problem in this way, not if they’d buy your specific solution. If they don’t want to own their insurance distribution, building a better captive platform doesn’t matter.

Compound learning across conversations. Track what you learn in each conversation. By conversation fifty, you should be pitching in their language. By conversation one hundred, you should sound like you’ve been in their shoes.

Get explicit permission to follow up. Every conversation should end with a clear next step: “When I have something to show you, can I come back?” Document who said yes.

Don’t rush to build. The temptation is to start building after ten conversations. But conversation one hundred teaches you things conversation ten couldn’t. Patience in the discovery phase creates velocity in the sales phase.

The Result: Sales Without Selling

When Authentic launched, Cole didn’t need to be a great salesperson. He just needed to follow up with people who’d already told him they wanted this. “I had so many meetings where not everybody that was excited about it said yes, but I was very pleased with the amount that were willing to move forward and take a chance on a startup.”

That’s the unlock. Most founders struggle with early sales because they’re trying to create demand, educate the market, and close deals simultaneously. Cole separated these. He created demand and educated the market in his first hundred conversations. When he launched, he just needed to close.

Your hundredth customer conversation can be research. Or it can be pipeline. Cole chose pipeline.