We Put the Whole First Symposium Together in Six Weeks. No Sponsors, No Tickets Sold, Off We Went.

Stacey Brown spent 21 years on the carrier side of insurance as an IT professional before founding InsurTech Hartford — and he’s explicit that he never set out to build a conference business. He started the first meetup group in late 2016, with the first actual event in April 2017, drawing directly on a late-90s-dot-com-era instinct: he watched investment starting to pour into insurance startups, recognized the pattern, and simply wanted to be part of the conversation as an industry insider — with no commercial ambition attached.

Insurtech London (led by Robin Merttens) came first as a genuine community model, and its influence on Stacey was direct and personal — watching colleagues in London attend regular networking events from his own desk in Hartford, with nothing comparable locally, was part of what he calls the “kindling” for starting something in his own city. A meeting with Jay (of ITC) early on functioned almost as an accidental dare — Jay, by Stacey’s account, expressed skepticism that a small community-driven event model could actually succeed at scale, which planted a challenge Stacey kept coming back to.

In Episode 94 of InsurTechTalk, Stacey and I covered how InsurTech Hartford grew from a Domino’s-pizza-funded meetup into a Mohegan Sun symposium, why the pandemic accidentally globalized his originally hyper-local community, and the deliberate design choices behind building “the best” event rather than “the biggest.”

About Stacey Brown

Stacey Brown is the founder of InsurTech Hartford, a regional insurtech community that grew from an informal 2016-2017 meetup into the InsurTech Hartford Symposium, now held at Mohegan Sun in Connecticut. He spent 21 years in insurance as a carrier-side IT professional (including time at AXA/XL) before starting the community. He has since begun helping activate similar communities in Chicago and Atlanta (working with Lisa Wardlaw), and separately co-founded InsurTech Slopes and InsurTech Trails, exclusive small-group networking retreats for founders and investors, alongside David Gritz of InsurTechNY.

Community, Not Commerce: The Key Distinction From the Big Conference Brands

Stacey drew a sharp, explicit line between what he does and how the major commercial conference brands (ITC, InsurTech Insights) operate. Those are genuine commercial ventures, built to turn a profit — which he considers entirely legitimate — but structurally different from what a true community requires. His pointed observation: nobody makes a living running a local insurtech community. The economics only work to cover costs, not generate profit, which means sustaining a community event long-term has to be driven by genuine passion in a local market, not commercial incentive. That distinction is also why he considers scaling community events genuinely hard — not the one-time event itself, but sustaining it regularly, year after year, in a way that doesn’t burn out the volunteer energy holding it together.

The Pandemic Accidentally Made Hartford Global

Stacey’s account of 2020 is a genuinely interesting story about a forced pivot producing an unplanned upside. InsurTech Hartford had planned to launch an Innovation Challenge that year, originally conceived as a local initiative — working with local universities to get students involved, with local carriers providing support. COVID forced the entire program online, and the unplanned consequence was that submissions started arriving from at least a dozen countries outside the US, coast to coast and beyond, rather than the single local university cohort originally envisioned. Stacey’s own framing: without the pandemic forcing that shift, he might still be trying to get one local university’s students to submit a single application — the crisis inadvertently gave the initiative a global reach it was never explicitly designed for.

Building the Symposium: From Domino’s Pizza to Mohegan Sun

The origin story of the flagship Symposium event is genuinely scrappy. The first-ever InsurTech Hartford Symposium in 2019 was assembled in six weeks, coming straight off a return from ITC with zero sponsors and zero tickets sold at the outset — and still drew nearly 300 attendees by the event date. Stacey calls it a “Goldilocks moment”: not too big, not too small, genuinely conducive to real collaboration in workshop-style sessions over a day and a half.

The pandemic forced a pause; in-person events resumed in September 2021, and the Symposium returned in April 2022 at the Connecticut Convention Center — a meaningful step up in scale and commitment (Stacey’s framing: renting a Marriott ballroom is one thing, committing to fill the Connecticut Convention Center is a genuinely different level of institutional bet). By 2023, the event moved to the Mohegan Sun Earth Expo & Convention Center — the venue that hosts the Miss America pageant — with attendance projected around 1,200.

The Real Differentiator: Experience, Not Content

Stacey’s framing of how to move an event “from good to great” is worth stating precisely, because it’s a genuinely transferable insight beyond insurance conferences specifically: everyone has content. Every conference has an exhibit hall, food and beverage, networking, speakers. Bad content clearly hurts an event, but good content alone doesn’t differentiate one conference from another at scale. What actually separates a great event, in his view, is the experience surrounding the content — the relationships people build, the quality of connection they leave with, not the sessions themselves.

His concrete execution of that philosophy at Mohegan Sun: intentionally structured smaller roundtable and peer discussion formats (roughly 45 minutes each) layered inside a 110,000-square-foot integrated exhibit hall, designed to keep energy and foot traffic concentrated in one space rather than scattering attendees across disconnected breakout rooms — plus a dedicated networking lounge, and two main stages positioned to keep the exhibit hall itself buzzing throughout the event rather than emptying out during programming.

Solving the “Hounded by Sales Reps for Six Months” Problem

Coming from the carrier side himself, Stacey named a specific, common attendee frustration directly: the fear that attending a conference means being aggressively followed up on by vendor sales teams for months afterward. His structural answer isn’t excluding vendors (which would eliminate the value sponsors and exhibitors need to justify attending at all) — it’s designing smaller, peer-only roundtable formats specifically so carrier attendees get concentrated peer-to-peer time without being locked in a room away from the floor entirely, balancing both audiences’ actual needs rather than favoring one over the other.

Three Tiers of Experience, Deliberately Priced Up, Not Down

Stacey noted a trend he’s seeing at some competing events toward cheaper tickets and broader access, and explicitly chose the opposite direction. InsurTech Hartford’s Symposium offers three tiers: general admission, VIP, and an “executive experience” tier that includes exclusive content, fine dining, and two nights in an upgraded executive suite with river views. His reasoning: rather than compete on price, the focus is on creating more exclusive value and differentiated experience for each specific audience segment (carriers, startups, investors) — a genuinely different strategic bet than the volume-maximizing approach some competing conferences pursue.

Content Credibility Through Analyst Partnerships

To ensure content quality keeps pace with the elevated venue and experience, Stacey built relationships with industry analyst firms — he specifically named Celent and IT Novarica, the latter building a dedicated CIO Council program directly inside the InsurTech Hartford Symposium, expected to bring 100-plus CIOs to the event through that single strategic relationship alone. His broader point: leaning on people who do actual industry research to moderate and drive discussion content, rather than relying purely on vendor-pitched sessions, is part of the deliberate quality-over-scale strategy.

Expanding Deliberately to Chicago and Atlanta

Asked why certain major insurance hubs — Chicago specifically — lacked a comparable insurtech community despite having strong carriers, brokers, startups, and investors present, Stacey’s answer circled back to the sustainability challenge: the ingredients existed, but nobody had sustained the ongoing work required to activate and maintain a regular community cadence. His approach to helping Chicago and Atlanta (working with Lisa Wardlaw) isn’t imposing the Hartford model wholesale — it’s sharing hard-won lessons about what does and doesn’t work, with the explicit long-term goal of reaching enough scale across multiple regional communities that organizers could eventually be paid a livable wage to sustain them professionally, rather than relying purely on volunteer passion indefinitely.

InsurTech Slopes and InsurTech Trails: Deliberately Small, Deliberately Exclusive

Alongside the Symposium, Stacey co-founded InsurTech Slopes with David Gritz — a genuinely different format born from a casual conversation about combining Gritz’s avid snowboarding with a VC-on-skis-style networking retreat modeled on similar events in other industries. The explicit design constraint: capped at roughly 30-40 people, deliberately kept small rather than scaled, specifically to maximize depth of relationship over breadth of attendance. Stacey’s own account of the format’s success: investors coming up to him afterward reporting they’d actually closed deals at the event — the kind of outcome he considers the clearest possible validation of the small-format thesis.

The events aren’t pure social retreats — each includes real programming (his example: Josh Curry of CyberCube-adjacent Serious Point discussing founder compensation structures from an investor’s perspective) alongside the bonding activities (skiing, white-water rafting, and — for the upcoming InsurTech Trails event in Aspen Snowmass — hiking, horseback riding, ATV/UTV experiences, and a rodeo evening).

Key Takeaways

• Genuine community events and commercial conference brands operate on fundamentally different economics — community events can rarely turn a profit, which means their sustainability depends entirely on local volunteer passion rather than commercial incentive
• A forced pivot to virtual programming during the pandemic can produce unplanned global reach — InsurTech Hartford’s Innovation Challenge went from a single local university target to submissions from a dozen-plus countries purely as a byproduct of the forced online shift
• The real differentiator between a good conference and a great one is the experience surrounding the content — relationships and connection quality, not the sessions themselves, since strong content alone is table stakes at any well-run event
• Deliberately smaller, structured peer roundtables inside a larger integrated exhibit hall can solve the tension between giving carrier attendees genuine peer time and giving vendors and sponsors the floor access their sponsorship justifies
• Pricing upward toward exclusivity and elevated experience, rather than downward toward volume, is a legitimate and differentiated strategic bet in a market where several competitors are optimizing for cheaper, broader access
• Partnering with genuine industry analyst firms for content credibility (rather than relying purely on vendor-pitched sessions) is a concrete way to elevate perceived event quality independent of venue or production value
• Deliberately capped, exclusive-format events (30-40 people) can produce outsized relationship value — including directly closed deals — that a large-scale conference structurally cannot replicate