He Validated a $120M Insurance Startup in One Weekend

One weekend, one WordPress site, a few thousand dollars in Google ads, and a fake error message at checkout. That was enough for Wayne Slavin to know he had to build Sure. A decade later, Sure has raised $120M and powers insurance programs for some of the world's biggest brands.

Key Facts

• Weekend validation conversion rate: 15.91% from ad click to checkout attempt (Wayne Slavin)
• Solo founder period: Worked alone for a full year before hiring anyone or raising a seed round (Wayne Slavin)
• Total raised: $120M, with no fundraise needed since 2021 Series C (Wayne Slavin)
• Profitability milestone: Net income positive since Series B; had every Series B dollar in the bank when they raised Series C (Wayne Slavin)
• PMF moment: End of August 2019 — an Elon Musk tweet about Tesla insurance triggered instant rocket-ship growth (Wayne Slavin)

How Wayne Validated an Insurance Startup in One Weekend

Wayne built a WordPress site with Google and Facebook ads, a full insurance enrollment flow, and a fake payment error at checkout. With 15.91% conversion from click to attempted purchase — and users retrying up to seven times — he had all the signal he needed to start Sure.

The idea came on a flight to Las Vegas. Wayne noticed passengers panicking during turbulence and wondered if you could sell life insurance right before takeoff. Coming from a payments and e-commerce background, he decided to test it the way he knew best: build something fast and see if people would pay.

Over one long weekend in 2014, he registered a domain, set up a WordPress template, created a good-better-best pricing structure with three insurance amounts, and ran Google and Facebook ads. The critical twist: when users reached the payment screen, they saw a fake error message. There was no real product yet.

The results were striking. Users went through the entire flow — entering flight details, naming a beneficiary, even writing a message — and then tried to pay multiple times after seeing the error. That behavior told Wayne the demand was real.

"We saw people coming back, going through that whole process seven times to try and buy it. And we were like, okay, if people are going to go through this whole thing multiple times to try and buy this product, they actually need it." — Wayne Slavin

"From clicking on an ad to going through that whole process, which isn't actually that simple, we converted fifteen point nine, one percent of people. Jeff Bezos would be jealous." — Wayne Slavin

Why Wayne Worked Solo for a Year Before Hiring Anyone

Wayne spent a full year alone, burning through savings in San Francisco, focused on two goals: finding an insurance carrier partner and raising a seed round. He didn't want to ask anyone to leave their job until there was real funding and real footing under the business.

Most founders bring on co-founders or early employees quickly. Wayne took a different path. For the first year, he was the only person working on Sure — no team, no paycheck, no external validation beyond his weekend test.

His reasoning was deliberate. As an engineer with product experience, he could straddle enough roles to make early progress alone. More importantly, he wasn't willing to ask friends to take financial risk until the company was on stable ground. He kept former colleagues loosely involved — getting design feedback, testing ad variants — but didn't ask them to quit their jobs.

When the seed round closed at $1.6M, that became the signal to bring five people on board. Three of those original five are still at the company ten years later.

"I wouldn't want to ask anybody to leave their job and put their financials on the line until this thing was at least on stable footing." — Wayne Slavin

• Key year-one goals: land a carrier partner and close a seed round
• Kept future hires engaged informally — feedback, side help — without asking them to quit
• Seed round of $1.6M was the 'launch party' moment that triggered formal hiring
• Commitment to future team: never promise a job before the money is real

Flying to South Africa to Land the First Insurance Partner

Wayne flew to South Africa for seven weeks with a clickable prototype and no insurance credentials. He chose South Africa because it's one market, one regulator, and English-speaking. That first partner became the proof point he used to close the equivalent U.S. partner shortly after.

Getting an insurance company to partner with an unproven startup is one of the hardest early enterprise sales. Wayne's insight was geographic: the U.S. insurance market is fragmented by state, making it slow and expensive to navigate. South Africa operates as a single regulated market, cutting the complexity dramatically.

Being originally from South Africa helped, but what actually closed the deal was a clear value proposition: Wayne wasn't asking the insurer to build anything. He was building everything. They just needed to supply the product.

After landing that first carrier deal and launching in the South African app store, Wayne returned to the U.S. — to Los Angeles, not San Francisco, since his now-wife had relocated them while he was overseas — and used the live product to approach the same insurer's U.S. operation.

"They didn't have to build anything new. We were building everything. We just needed their product to sell." — Wayne Slavin

"That first insurance company in South Africa provided the validation to go to the U.S. and meet with that same insurance company and say, we're already doing it with your counterparts. Why don't we just do it here?" — Wayne Slavin

The Slow Pivot from Consumer App to Embedded Insurance Platform

Sure didn't flip overnight from a direct-to-consumer flight insurance app to a B2B embedded insurance platform. Wayne ran both models in parallel — validating the new embedded model with renters insurance partners while keeping the mobile app live — until the economics and traction made the choice obvious.

The consumer app worked technically but had structural problems: low average policy value, no recurring revenue, high customer acquisition costs, and a commodity product where price was the only differentiator. Wayne recognized that the real asset Sure had built was the transaction infrastructure, not the consumer brand.

The pivot started with renters insurance embedded inside property management platforms — places where customers were already acquired and insurance was a natural add-on with zero CAC. The economics were immediately better. The first partner, Onerent, went out of business the week before launch. But the framework was proven with the next round of partners, and the business ramped to a million in ARR faster than Wayne expected.

The embedded model also revealed a second customer: the insurance companies themselves. Carriers wanted to license Sure's platform to run their own digital programs. That dual-sided insight — brands need infrastructure, carriers need software — became the core of what Sure is today.

"I hadn't proven the embedded insurance thing yet. So we kind of kept the one thing going while validating the second thing and eventually just kind of slowly sunset the mobile app as the embedded insurance distribution ramped up." — Wayne Slavin

"Our DNA is more about building product and tech. Less about marketing and customer acquisition. And in hindsight, my why is much more about helping other people build things versus us building a brand." — Wayne Slavin

How an Elon Musk Tweet Created Instant Product-Market Fit

In August 2019, Elon Musk tweeted about Tesla Insurance. Sure was the infrastructure behind the program. The result was an immediate, overwhelming surge in transactions that gave Wayne total conviction that the embedded insurance model would produce billion-dollar outcomes.

Sure had been building toward embedded auto insurance, but validation at scale came suddenly and from an unexpected direction. When Tesla announced its insurance product and Elon tweeted about it, consumer demand flooded in instantly. Sure was powering the rails behind that program.

Wayne describes it as the moment every prior bet was confirmed. The combination of a trusted brand, a relevant product, and zero friction at the point of purchase created what he calls a 'rocket ship' of transactions. It also clarified the long-term mission: help the world's biggest brands build their own insurance programs using Sure's infrastructure.

Wayne is careful to note that this kind of lightning-strike moment isn't repeatable by design. But it crystallized the hypothesis that has driven every decision since: consumers buy insurance from brands they already trust, and the convenience of not switching contexts is worth more than marginal price differences.

"End of August 2019, there was a tweet from the chief tweeter, and a program launched. And it was a rocket ship. Literal rocket ship of insurance transactions, sales, and it just was like, oh my God. If you have the right brand and the right product, in the right place, this is going to be a billion dollar business before we can imagine." — Wayne Slavin

"Deca billion dollar insurance brands will be built by Sure, because of what we saw in auto insurance with that AV brand." — Wayne Slavin

How Sure Reached $120M Raised — and Stayed Profitable Since 2021

Sure raised $120M across multiple rounds but has operated profitably since its Series B, with every Series B dollar still in the bank when the Series C closed. Wayne credits private-equity-style financial discipline — not venture growth-at-all-costs thinking — for giving the company control of its own destiny.

Sure's capital story is unusual in venture-backed startups. When Wayne raised the Series C in 2021, Sure was already net income positive — not 'community adjusted EBITDA,' as Wayne puts it, but real profit. The raise was strategic, not a lifeline.

Since 2021, Sure hasn't needed to raise again. That financial independence has allowed the company to make long-term product decisions: progressively owning more of the insurance supply chain, from software to implementation to operations to balance sheet to underwriting. Each layer added makes Sure harder to replicate and more valuable to enterprise clients.

Wayne frames financial discipline as a prerequisite for good decision-making. Founders who are starved for oxygen, he argues, tend to make short-term calls that compromise long-term positioning. Profitability isn't the enemy of ambition — it's what funds it.

"When we raised our Series C in 2021, we had every dollar of our Series B in the bank still and we were actually profitable, net income positive, not some weird community adjusted EBITDA thing." — Wayne Slavin

"It's hard to control your own destiny when you're starved for oxygen. You don't tend to make the right long-term decisions." — Wayne Slavin

Consumer App vs. Embedded Insurance: Sure's Two Models