ITC Was Built for a Focus Group of One

Caribou Honig opened Episode 48 talking about crabbing on the Chesapeake Bay — a piece of chicken tied to a string, attached to a $3 PVC pipe from Home Depot, stuck in the sand while you wait with a beer for the line to go taut. It’s a fittingly low-tech hobby for someone who spends the rest of his time thinking about where technology is headed next, alongside kayaking close enough to wild dolphins near his home in Virginia to hear them breathe through their blowholes.

Caribou is best known as chairman and co-founder of InsureTech Connect (ITC), the industry’s largest annual conference. But the origin story, which he told in detail on this episode, is genuinely small in scale. In 2015, while focused on the insurtech category as an investor at QED Investors, Caribou went looking for a conference worth attending and couldn’t find one that fit what he needed — so he set out to build it himself. A former colleague introduced him to Jay Weintraub, who was independently planning his own insurance innovation conference. Their first conversation, Caribou recalled, could have gone one of two ways: a short one, if they decided to build competing events, or a long one, if they found real reason to collaborate. Jay’s original concept was narrower than Caribou’s; Caribou persuaded him to build the broader version — effectively the conference Caribou himself wanted to attend, built for what he calls “a focus group of one.” The lesson he draws from it, and one he considers a genuine startup principle: build something great for one clearly articulated need before trying to build something merely good for many. At the first ITC in October 2016, the team hoped for 600 attendees and worried 1,000 might be too many to handle; 1,500 showed up.

About Caribou Honig

Caribou Honig is Chairman and Co-Founder of InsureTech Connect, co-founder of the Blueprint (real estate tech) and HR Transform (future of work) conferences, and a General Partner at SemperVirens Venture Capital. He co-founded QED Investors in 2008, where the firm’s mandate evolved from data-intensive startups broadly into a fintech (and adjacent insurtech) focus, including significant later expansion into Latin America.

From QED to SemperVirens

Caribou’s move into SemperVirens came through HR Transform, the future-of-work conference he co-founded with Jay Weintraub. Through that event, he met the founders of a boutique, ecosystem-focused VC fund built around current and former senior HR executives and benefits brokers, alongside a future-of-work-focused accelerator. He joined first as a special advisor, then an investment committee member, and became a General Partner in early 2021. He described the fund’s underlying approach — and its Latin-derived name, meaning something close to “always growing” or “evergreen” — as sharing enough DNA with QED’s early philosophy that the move felt like a natural extension rather than a departure.

Building Blueprint: The ITC Playbook, Applied to Real Estate

Blueprint, Caribou’s newer conference focused on real estate technology, runs deliberately at the same venue and around the same dates as ITC — Blueprint on the third floor of Mandalay Bay, ITC on the second. The overlap is intentional: Caribou sees a genuine and growing intersection between real estate and P&C insurance, spanning business interruption, homeowners risk, and anything tied to the physical condition or use of a building.

He was careful to note that “real estate tech” and “proptech” aren’t quite synonymous in his view — proptech is the more VC-native shorthand, while people already working in real estate tend to think in broader terms: financing, construction, new ownership and usage models, even something as specific as retrofitting EV chargers into a multifamily property. He drew a direct parallel to ITC’s own value proposition: what makes an event like this work isn’t just who attends, but the mindset they bring — a rare, deliberate window where people set aside their day-to-day priorities to genuinely explore what’s possible.

Where Insurance and Real Estate Actually Overlap

Several concrete intersections came up. Embedded insurance strategies — following closely behind embedded finance’s rise in fintech — are pushing providers to explore real estate intermediaries (mortgage servicers, landlords) as distribution channels. On the multifamily rental side, Caribou pointed to founders reexamining the security deposit itself: rather than a blunt instrument for managing lease-break or damage risk, could an insurance-like structure serve the same purpose more efficiently for both landlord and tenant? He also connected IoT directly to the theme, describing a water-meter sensor he installed himself at his own home that alerts him to unusual water flow — a near-exact parallel, he noted, to automotive telematics’ own evolution from aftermarket plug-in devices toward sensors built in by the manufacturer at construction time.

He also flagged an unexpected connection point: life insurers, given how much of their investment portfolio sits in real estate, have a direct interest in better understanding property-level risk — though he noted, half as a standing question, that the executives actually responsible for those investment portfolios (chief investment officers) don’t typically attend ITC today, raising the question of whether that changes as the real estate/insurance intersection deepens.

Incumbents Aren’t Asleep This Time

Reflecting on how real estate tech compares to where insurtech stood in its own early days, Caribou pointed to a meaningful difference: in 2015, insurtech was barely a recognized category — Google Trends data for the term from that period shows almost nothing. Real estate tech, by contrast, is already a well-established category, with genuinely active innovation arms inside major incumbents rather than the more defensive posture insurance incumbents showed in 2015. What he believes hasn’t existed yet is a shared venue where real estate’s different types of innovators and investors — developers, brokers, property managers, and companies like Zillow that already won their first wave of disruption and are now figuring out their next one — can convene the way ITC brought insurance’s ecosystem together.

Advice: The Three-Body Problem

For his closing recommendation, Caribou pointed to The Three-Body Problem trilogy by Liu Cixin — technically science fiction, but, in his description, really more a work of social and political ideas than a conventional genre read, and dense enough to reward the time it takes.

Key Takeaways

• ITC’s founding principle, per Caribou: build something great for a focus group of one clearly articulated need, rather than something merely good for many — the first event drew 1,500 attendees against an internal hope of 600-1,000
• Blueprint is a deliberate structural bet that real estate and insurance share enough of a Venn diagram — business interruption, homeowners risk, embedded distribution through landlords and mortgage servicers — to justify running the two conferences at the same venue and dates
• Real estate tech incumbents, unlike insurance incumbents in 2015, already have active innovation arms — the opportunity Caribou sees isn’t waking up a sleepy industry, but creating the first shared venue for its different types of innovators and investors to convene
• IoT in real estate is following the same arc as automotive telematics: aftermarket sensors today, giving way to devices built directly into property at construction time
• Life insurers have a direct, underexplored interest in real estate risk technology given how much of their investment portfolio sits in property — though the executives who’d act on that insight (CIOs) aren’t yet a visible part of the ITC audience