It Started at a Panera Table Outside DC. Six Months Later, 1,500 People Showed Up in Vegas.

Bill Harris met Jay Weintraub (ITC’s co-founder) back in 1999 — Bill hired Jay for his first job at advertising.com, where Bill ran media buying (he jokes he’s directly responsible for the invention of the pop-up ad, back when the company’s chief rival was DoubleClick). Years later, after Jay had left advertising to build events (starting with LeadsCon) and Bill had spent roughly a dozen years founding and running a fintech company doing digital payments for brick-and-mortar retailers, Jay called with an idea: a VC named Caribou (Caribou Honig, a Harvard classmate of Bill’s) wanted to build a fintech-adjacent event specifically for insurance — but knew nothing about running events. Jay knew events but nothing about insurance deal flow. Bill, with fintech entrepreneurship experience and Harvard ties to Caribou, was the missing piece.

The three of them plotted the entire thing out at a Panera table outside DC, near Caribou’s home in Richmond, Virginia. From that conversation to the first live event in Vegas took less than six months — a timeline Bill now considers borderline reckless in hindsight, precisely because his own inexperience with the events business kept him from realizing how aggressive it was. That first show drew 1,500 attendees.

In Episode 88 of InsurTechTalk, Bill and I covered ITC’s growth from that first show to roughly 9,000 attendees and 400 exhibitors in 2022, what actually changed in insurtech funding discipline since the early “dumb money” years, and the international expansion bringing ITC to Latin America, Asia, and (via the DIA acquisition) Europe.

About Bill Harris

Bill Harris is Chief Revenue Officer of InsureTech Connect (ITC), which he co-built alongside Jay Weintraub and Caribou Honig starting in late 2015/early 2016. Before ITC, Bill spent roughly 12 years founding and running a fintech company focused on digital payments for retailers, and earlier worked in online advertising media buying at advertising.com. ITC is now owned by Clarion Events (a UK-based global events company), and in 2023 was expanding to ITC LatAm (Miami), ITC Asia (Singapore), and, via Clarion’s acquisition of DIA, a European presence in Barcelona alongside the ITC Vegas flagship.

From 1,500 to 9,000 in Six Years

ITC’s growth trajectory, in Bill’s own numbers: 1,500 attendees at the first Vegas show, growing roughly 50-100% year over year, reaching 9,000 attendees and 400 exhibitors in 2022 — a scale Bill still describes as remarkable given how genuinely improvised the first six months of building the company were. The original organizing thesis, credited explicitly to Caribou and Jay in naming the show: bring together three groups that had never been convened in one place before — investors, insurance incumbents (carriers and reinsurers), and innovators (startups) — plus the technology vendors and professional services firms supporting all three. Nothing like that combined format existed in insurance before ITC.

Why In-Person Still Wins, Confirmed Twice

Bill’s read on 2021 and 2022, coming out of the pandemic, was unambiguous: nothing replaces face-to-face, in-person networking. Zoom, podcasts, and webinars accelerated certain kinds of connection during the pandemic, but 2021 (held during the Delta variant surge) and especially 2022 confirmed that elbow-to-elbow, casual, organic interaction produces something video calls structurally cannot. His most personally revealing observation: several people on his own ITC team hadn’t met each other in person until an actual ITC show — remote work hasn’t just changed how companies meet clients, it’s changed how colleagues build relationships with each other, a dynamic he considers genuinely under-discussed.

The Content Structure Fix: From One Stage to Seven Tracks

A concrete, practical lesson from attendee feedback: earlier ITC events ran content largely on a single flow, without organizing by topic — cyber, auto, home, life and health all mixed together on one stage’s schedule. With insurers frequently sending dozens of staff to divide and conquer the show, that structure made it hard for teams to plan who should attend what. In 2022, ITC restructured into seven distinct breakout tracks plus an eighth demo stage running in the expo hall throughout each day — a structural change Bill credits directly with improving how attendees could actually digest the volume of content on offer.

10,000 Scheduled Meetings, Plus However Many Happened Organically

The center of ITC’s expo hall is deliberately reserved as a dedicated one-on-one meeting zone — described by Bill as prime real estate, not an afterthought. In 2022, the app-scheduled meeting system alone produced 10,000 one-to-one meetings over three days, with an unknown (and likely much larger) number happening organically around the show floor, at the coffee lounge, the beer garden, and other informal gathering points Bill listed — including, notably, a “puppy lounge” he considers a small but genuinely beloved addition, partly because he personally misses his own dogs while traveling for the show.

Kickoff Day: From 6 Summits to 16

Bill described a deliberate expansion of ITC’s opening day programming, rebranded from “pre-conference day” to “kickoff day” specifically to make clear ITC is a genuine three-day event, not a conference with an optional preamble. In 2022, roughly 7,500 of the show’s 9,000 total attendees showed up specifically for kickoff day. The number of dedicated summits held that day jumped from six in prior years to 16 in 2022, covering specific emerging themes: an ESG summit (with Sabine VanderLinden and the team at Sonar), Broker Tech Connect (with Broker Tech Ventures), Group Tech Connect (with Finios, its second consecutive year), and a new Capacity Connect summit (conceived by Gohar Kalantari at Steer) specifically bringing together capacity providers and capacity seekers for focused matchmaking.

Reading Trends Through the Crowd, Not Predicting Them

I pushed Bill on whether ITC actively identifies emerging trends or simply reflects what’s already happening in the industry. His honest answer: ITC isn’t the “news breaker” — it’s the marketplace where the news breakers convene, and its real skill is recognizing what people are already asking to hear more about and putting a spotlight on it. Concrete examples from the 2022 show: embedded insurance remained a major theme (he cited three embedded insurers — Oyster, Walnut, and Vertical Insurer — all raising seed funding in roughly the same week, in the $3.6-4 million range each), alongside continued momentum in cyber, parametric insurance, and early exploratory sessions on Web3 and the metaverse — the last of which Bill was candid might turn out to be ahead of its time, given how much capital is being pushed into virtual-world initiatives without matching consumer pull yet.

Expanding Beyond Vegas: LatAm, Asia, and DIA

ITC’s international strategy accelerated meaningfully going into 2023, building on Jay’s original ambition that ITC Vegas should be the flagship of a genuinely global footprint, not the only show:

• ITC Asia launched in Singapore in 2021 and had already proven successful
• ITC LatAm was launching for the first time in April 2023, in Miami at the Fontainebleau, built specifically around consolidating the fragmented regional Latin American insurtech ecosystem — Brazil (with longtime partner Gustavo and CQCS), Argentina (100 Seguro’s Leo and Hernán), and other regional players — into a single, unified event rather than requiring international attendees to separately attend shows in Brazil, Colombia, and Argentina to cover the region
• ITC Europe, via Clarion’s acquisition of DIA (the Amsterdam-founded conference run by Roger Peverelli and Reggy de Feniks, whose production values Bill specifically admired for years before the acquisition), moving to Barcelona — with an explicit goal of preserving DIA’s distinct aesthetic and feel rather than simply overlaying the ITC format on top of it

The full 2023 calendar Bill outlined: ITC LatAm in April, ITC Asia in late May, ITC Europe/Barcelona in late June, and ITC Vegas at the end of October — with roughly 15% of the Vegas show’s total audience already coming from outside the US, representing 60 countries.

The Israel Delegation Partnership

Bill and I discussed a new collaboration — a partnership between ITC and Kobi Bendelak, organizing curated delegations of US insurance executives and investors to Israel’s insurtech ecosystem, deliberately capped at a small group size (roughly 15-20 people) to preserve a genuine “white glove concierge” depth of access, in explicit contrast to ITC’s own scale-driven model of thousands of attendees. Bill noted his own personal connection to the idea — his prior fintech company had Israeli co-founders, and Start-Up Nation (visible on his own bookshelf during the conversation) had shaped how he thought about Israeli entrepreneurial culture well before this specific partnership existed.

Why “Dumb Money” Insurtech Funding Is Over

This was Bill’s sharpest and most direct market read. His framing of the 2016-2018 era: if you had a plausible idea and could label yourself insurtech, funding was genuinely easy to access — “dumb money,” in his words, flowing in with limited scrutiny of underlying unit economics. That era, in his clear assessment, is over.

What replaced it: capital still flows readily to companies with genuinely proven unit economics and a track record — but simply claiming “AI” or “machine learning” in a pitch deck no longer moves the needle on its own. His pointed comparison to public insurtechs: companies with loss ratios genuinely out of balance are now visibly struggling to justify enterprise value when they’re writing large claims checks constantly, regardless of how sophisticated their original pitch sounded. He referenced comments from Root’s CEO Juan Andrade at ITC specifically about needing forward-looking data discipline to actually close the gap between data collection and genuinely reduced loss ratios — not just claiming AI-driven underwriting as a marketing point.

What He Actually Expects in 2023-2024

Bill’s forecast, delivered candidly as informed prediction rather than certainty:

• Consolidation and exits accelerate. Roughly six to seven years is the typical VC time horizon, and a wave of insurtechs funded in 2016-2018 are hitting that point simultaneously — meaning more acquisitions (he cited Steadfast’s acquisition of Insurcore as a recent example), some outright business failures, and some “plan B” pivots as capital runways run out
• Recession impact on insurance specifically is likely modest and cyclical, not catastrophic — his personal (explicitly non-economist) read is that this is a normal cyclical slowdown, not a structural break, though venture funding pace from insurance company venture arms may soften somewhat
• Climate and data integration remains the real growth frontier. His framing: carriers increasingly have access to genuinely rich datasets (geospatial, weather, climate risk) but the real unsolved problem is operationalizing that data into core systems in a way that lets a carrier proactively warn and support a policyholder ahead of a coming event, minimizing loss before it happens — not just pricing risk more accurately after the fact

Advice: There’s Only One Right

Asked for a closing recommendation, Bill offered something he uses regularly with his own kids: “there’s only one right.” His framing: life is a continuous series of choices, and while people can hold different opinions, there’s only one set of underlying facts — and correspondingly, when a genuine ethical or values question is on the table, there’s only one correct answer, however uncomfortable finding it might be. His broader point: staying anchored to that discipline, distinguishing between legitimate difference of opinion and an actual right-versus-wrong call, is a durable principle worth carrying into any year, not just 2023 specifically.

Key Takeaways

• ITC’s entire founding structure — investors, incumbents, and innovators convened together — filled a genuine gap in the insurance events landscape that didn’t exist before 2016, built from initial concept to a live 1,500-person show in under six months
• Restructuring content into discrete topic tracks (seven breakout stages plus a dedicated demo stage) directly solved a real attendee navigation problem as the show scaled past what a single content stream could serve
• In-person networking produced measurably higher engagement than any virtual alternative even after two years of pandemic-driven advances in remote collaboration tools — a signal borne out by 10,000-plus scheduled meetings in three days at the 2022 show
• ITC’s international expansion (LatAm, Asia, DIA/Europe) is explicitly designed to consolidate fragmented regional ecosystems into single unified events rather than forcing international coverage to happen show by show, country by country
• The “dumb money” era of insurtech funding — where a plausible pitch and buzzwords alone attracted capital — is genuinely over; funding now requires demonstrated, proven unit economics, not just a compelling narrative
• Consolidation, exits, and some outright business failures are expected across the 6-7-year-old insurtech cohort as VC fund timelines mature and force resolution, independent of broader recession dynamics
• The real unsolved growth opportunity in insurance data isn’t collection — carriers already have access to rich datasets — it’s operationalizing that data into core systems to proactively reduce loss before it happens, not just price risk more accurately after the fact