From Zero Inbox to First Customer: Authentic’s Four-Month Desert Wandering Period

From Zero Inbox to First Customer: Authentic’s Four-Month Desert Wandering Period

Late 2022. Cole Riccardi opened his laptop to check his inbox. Zero unread messages. No meetings scheduled for the week. No warm introductions pending. Just a conviction that captive insurance could reshape how small businesses buy coverage—and absolutely no one waiting to hear about it.

In a recent episode of Category Visionaries, Cole Riccardi, CEO and Founder of Authentic, described this period as “wandering in the desert.” It’s the phase every founder faces but few discuss honestly: when you’ve left your job, committed to an idea, and have nothing but conviction to sustain you. Four months later, Cole had Slow Ventures funding and a pipeline of customers ready to sign. What happened in between reveals how wandering becomes traction.

The Reality of Zero

The desert metaphor isn’t dramatic—it’s accurate. “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.

This is the moment most founders underestimate before starting a company. You expect uncertainty. You expect financial stress. But you don’t expect the silence. When you’re at a company, your calendar fills itself. People need things from you. Your inbox is a problem because there’s too much in it. As a first-time founder with no product and no customers, the opposite problem emerges: nobody needs anything from you because you’re not yet relevant to their world.

Cole had left Aquiline, an investment firm where he’d spent six years. He had domain expertise, a network, and an insight about captive insurance that felt obvious to him. But obvious to you doesn’t mean obvious to the market. And expertise doesn’t automatically translate to meetings.

The challenge isn’t just practical—it’s psychological. “You don’t have meetings and nobody probably wants to talk to you,” Cole notes. Past tense. At some point, people will want to talk to you. But right now, in month one of wandering, they don’t. And that silence can break founders who mistake it for invalidation.

The Direction: Keep Wandering Where You Believe

Cole’s framing of “wandering” is crucial. He’s not saying aimless or lost. He’s saying directional movement without visible progress markers. “You just need to kind of keep wandering in the direction that you believe is the right path.”

The direction for Authentic was clear: talk to anyone who could benefit from a turnkey captive insurance platform. “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.

This meant three specific channels: franchisors who could offer insurance to their franchise networks, vertical software companies trying to add embedded insurance, and associations looking for member value-adds. “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.”

Notice what Cole isn’t doing: he’s not exploring multiple business ideas, testing different markets, or keeping his options open. The direction is set. The wandering is about finding people within that direction, not finding a different direction.

This focus matters because it’s what separates productive wandering from actual lostness. Lost founders explore too many directions simultaneously, never going deep enough in any one to learn if it works. Wandering founders commit to a direction and persist long enough to find out.

The Daily Practice: Compound Learning Across Conversations

What do you actually do when wandering? For Cole, the answer was simple: have conversations. Lots of them. With everyone who might care about this problem.

The pitch was straightforward: “If you guys had a platform or some type of infrastructure, would you start your own captive insurance program and offer insurance to your small business customers or small business members?”

Early conversations yielded “overwhelmingly positive” feedback. But feedback isn’t traction. “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,” Cole learned.

So why keep having conversations if positive feedback doesn’t equal customers? Because of compound learning. “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.”

This compounding effect is what makes wandering productive. Conversation one teaches you how franchisors think about insurance. Conversation twenty teaches you the specific objections they have to traditional carriers. Conversation fifty teaches you the exact language that resonates. By conversation one hundred, you’re not pitching your idea—you’re articulating their problem in words they’ve been searching for.

The daily practice isn’t complicated: wake up, reach out to potential customers, have conversations, document what you learn, adjust your pitch, repeat. But the psychological challenge is maintaining this practice when nobody’s buying, nobody’s signing, and your inbox stays empty.

The Conviction Requirement: Why You Need It

Wandering in the desert requires a specific type of conviction. Not conviction that you’ll succeed—that’s outcome-based and the desert provides no evidence you’re moving toward that outcome. You need conviction that the direction is right, even without proof.

For Cole, this conviction came from two sources. First, his six years at Aquiline watching vertical software companies struggle with embedded insurance. He’d seen the problem from multiple angles across multiple companies. This wasn’t theoretical—it was observed pattern.

Second, his family member’s experience with horse farm captive insurance programs. This proved the model could work for groups of small businesses. The question wasn’t whether captives worked—it was whether the infrastructure could make them accessible.

“I was really passionate about this idea. I still obviously am. It’s obvious to me, maybe more people in my demographic that I would rather buy insurance through a trusted channel that I already interact with, as opposed to some insurance brand that I haven’t worked with,” Cole explains.

That conviction—”it’s obvious to me”—is what sustains you when your inbox is zero. Not everyone sees it yet. Most people won’t take your meeting. But you know where the market is heading because you’ve spent years observing it from a unique vantage point.

Without that conviction, the first month of silence would prompt a pivot. With it, silence is just noise you ignore while continuing to wander in the right direction.

The Breakthrough: When Wandering Becomes Traction

Cole doesn’t mark the exact moment when wandering became traction, but the signals emerged. “A couple months after I had decided to make the leap into entrepreneurship,” Slow Ventures made an early bet.

What did they see? “I think they candidly just saw my conviction level in it and the fact that I had been in this space for six or seven years. And so I think that’s what really prompted them to write the check.”

The funding changed the practical constraints but not the fundamental activity. Cole continued having conversations, continued learning, continued refining the pitch. But now there was validation that the direction was right—at least one sophisticated investor believed this was worth building.

The customer pipeline emerged from the same conversations. When Authentic finally had a working prototype, Cole “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 desert wandering period had built a qualified pipeline disguised as customer discovery. Not everyone converted, but “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.”

The Timeline: How Long Can You Wander?

Cole’s desert period was three to four months. That’s short relative to some founder journeys, but it felt long in the moment. The timeline question every founder faces: how long do I keep wandering before admitting this direction is wrong?

There’s no universal answer, but Cole’s experience suggests a framework. You can wander as long as:

The feedback remains consistently positive. If every conversation validates the problem and the desire for a solution, keep going. If conversations start contradicting each other or the problem isn’t resonating, reconsider the direction.

You’re learning something new in each conversation. Compounding learning means each conversation builds on previous ones. If you’re hearing the exact same things by conversation fifty, you’ve probably extracted all the insight available and need to move to building.

Your conviction stays intact. This is personal. Some founders can maintain conviction for years. Others need external validation more frequently. Cole had six years of domain expertise building his conviction—that bought him runway to wander longer than someone exploring a brand new space.

You have the financial runway. This is practical. If you can only afford six months before needing income, you can’t wander for twelve. Cole’s timeline was partly dictated by when Slow Ventures came in with funding.

The Lessons: What Makes Wandering Productive

Cole’s desert period offers several lessons for founders in similar situations:

Direction matters more than speed. Moving quickly in the wrong direction wastes time. Moving deliberately in the right direction feels slow but compounds.

Conversations are work, not networking. Cole wasn’t networking—he was systematically talking to every potential customer to understand their needs and build relationships that would convert later.

Conviction isn’t about believing you’ll succeed. It’s about believing the direction is right even when no one else sees it yet. That belief has to come from insight, not optimism.

Document what you learn. The compound learning effect only works if you’re capturing insights and building on them. Each conversation should make your next pitch sharper.

Wandering has an end state. At some point you need to build. Cole wandered for three to four months, then had enough clarity to start building. Perpetual wandering is procrastination.

From Desert to Destination

Today, Authentic is a team of twelve with 16 million in funding, active customers, and word-of-mouth pipeline in three distinct channels. But it started with an empty inbox and a founder willing to keep walking when no one was following.

“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,” Cole reflects. But here’s what he doesn’t say explicitly: that challenging part is temporary. It ends not because the market suddenly decides to pay attention, but because you keep moving in the right direction long enough that your wandering creates its own path.

The desert doesn’t last forever. But you have to be willing to walk through it.