ITC 2021’s Real Theme Wasn’t Technology. It Was Capacity.

Jay Weintraub, founder of Connective (the parent company behind ITC Vegas, Blueprint, and the newly launched Manifest), returned for a second annual year-end conversation — a genuine tradition at this point, recorded between Christmas and New Year’s as Omicron cases surged. Between comparing pandemic Greek-alphabet fatigue and swapping notes on how different New York felt this time around, the conversation moved through what actually happened at ITC 2021, what’s coming next across Connective’s growing portfolio of events, and a genuinely useful framework for thinking about where insurtech capital, customers, and capacity actually flow.

In Episode 59 of InsurTechTalk, Jay and I covered why so many ITC 2021 conversations turned out to be about reinsurance capacity rather than technology, his blunt take on empty “we are an AI company” pitch decks, and why crypto insurance is a genuinely harder problem than the hype suggests.

About Jay Weintraub

Jay Weintraub is founder of Connective, the events company behind ITC Vegas (which he also founded), Blueprint (a real estate technology conference), and Manifest (a new logistics technology conference launching January 25-27, 2022 at the Paris Las Vegas). ITC Vegas grew from roughly 1,500 attendees at its first event to about 6,000 attendees in 2021.

ITC 2021: Bigger, and About More Than Technology

Jay reflected on ITC Vegas 2021 as a genuinely emotional milestone — 6,000 people gathering in person after nearly two years apart, with a specific highlight being a live interview studio built at the far end of the expo hall (an idea that came together only after Talkdesk, initially looking for remaining sponsorship inventory, offered to sponsor exactly that setup). He was quick to note, with some pride, that he made it through the event without testing positive for COVID.

Two things stood out to him from his own interviews on-site. First, unsolicited requests from multiple attendees to bring an ITC event to Latin America, reinforcing how much insurtech activity is happening well outside the US (drawing a parallel to Nubank’s recent IPO). Second, and more structurally interesting: several founders told him that many of their most important ITC meetings weren’t really about technology or distribution at all — they were about capacity, meeting reinsurance and risk-capacity partners directly. That observation is pushing Connective to consider a dedicated mini-summit on capacity specifically at a future ITC.

The Three Cs: Capacity, Capital, and Customers

The conversation’s recurring bit (and self-aware drinking-game premise) was a running tally of buzzwords starting with “C” — but underneath the joke sits a genuinely useful framework Jay and I worked through together: whatever insurtech company you’re building, connection ultimately means one of three things — connecting to capacity, to capital, or to customers. Startups pitching into cyber, for instance, are increasingly running into their own capacity constraints and having to find alternative paths (citing Corvus as one example of a company building toward other lines of business as a response). Jay’s closing framing tied all three back to a single underlying principle: none of the three Cs matter if a company isn’t solving a genuine, specific pain point — that’s what actually pulls in capacity, capital, and customers together, not the reverse.

Blueprint and Manifest: Beyond Insurance, on Purpose

Jay described Blueprint, Connective’s real estate technology conference held in parallel with ITC (on the floor above), as having outperformed his own expectations — drawing roughly 750 attendees who weren’t otherwise at ITC. His reasoning for running it in parallel: venture capital, especially corporate venture capital, already treats real estate tech and insurtech as adjacent categories, since real estate is a massive asset class carriers invest premium dollars into, and companies like Hippo and Rhino genuinely straddle both categories at once. Blueprint will run independently in September going forward rather than overlapping directly with ITC.

Manifest, a brand-new logistics technology conference, was set to launch January 25-27, 2022 — deliberately timed, Jay joked, right as supply chain disruption became something literally every consumer was living through firsthand. He cited a striking data point: roughly $7 billion was invested into logistics tech startups in Q3 2021 alone, with more unicorn-stage private logistics companies than in insurtech — a space that, like insurance itself, looks superficially “solved” from the outside but turns out to have plenty of the same unglamorous, unsolved friction (his parallel: agents still submitting business by fax in insurance; the logistics equivalent problems Manifest is built to surface).

InsuranceGIG and Why Workflow Beats Pure Connection

We discussed Michael Lebor’s InsuranceGIG directly — a technology marketplace for insurance, which Jay compared to “Zapier for insurance.” The striking part, in his telling, is how basic most of the actual use cases still are: large brokers frequently need help with problems as fundamental as converting a PDF into structured data and feeding it into a CRM or agency management system, well before getting to more sophisticated AI-driven tools like Relativity6 or Kodiak. Jay connected this to his own long-standing appreciation for workflow tools specifically (he name-checked Zapier as a tool he’d underestimated for years before actually using it) — his point being that connecting two systems is only half the job; without a workflow that actually does something useful with that connection, the connection itself falls flat.

“We Are an AI Company” Should Disqualify a Pitch

This was one of the sharper exchanges in the conversation. I pushed a specific pet peeve: pitch decks that lead with “we are an AI company” without naming a concrete functionality — what’s actually being predicted, what specific classification or recognition task the model performs. Jay agreed directly, contrasting it with Relativity6’s own evolution as a company: it started by pitching AI-driven churn prediction broadly, then refocused specifically on a narrow, laser-clear value proposition — automated commercial classification coding — which is a functionality, not a buzzword. His summary distinction: a company that is genuinely providing AI as a packaged capability is a legitimate “AI company”; an MGA or insurtech using AI as one input toward better underwriting or retention should be describing the underlying business outcome (better risk selection, better retention, lower operating cost relative to revenue), not wearing “AI company” as the pitch itself.

Crypto Insurance: Genuinely Harder Than It Sounds

ITC 2021 included a session on crypto and insurance (moderated by Jaclyn Lesage Krauss), which Jay compared directly to ITC’s earlier, largely premature blockchain sessions in 2016 and 2017 — chosen “because we felt like we had to,” before blockchain had found a real at-scale application. His view: crypto may be blockchain’s first genuinely at-scale killer application, but insurance for crypto assets specifically remains too broad and poorly defined a category to meaningfully address yet, and he explicitly invited any founder with a genuinely specific crypto insurance use case to reach out.

We worked through why this is harder than it first appears. Unlike almost every other insurance category, crypto assets are purely digital from inception — not a physical asset being digitized, and not a “digital twin” layered onto something physical. That breaks a lot of insurance’s traditional assumptions, which are built around insuring physical things or events. A concrete illustration: there’s no such thing today as general “wallet insurance,” in the way there’s homeowners or auto insurance — theft protection in crypto more closely resembles how credit card companies handle fraud (recognition, replacement, chargeback protection) than a true underwritten insurance product, and theft itself is a strikingly poor fit for classic underwriting: even within homeowners insurance, theft coverage is a limited add-on rather than the default, and “theft” risk varies enormously by context (a ground-floor apartment versus a tenth-floor unit, for instance) in ways that don’t map cleanly onto how crypto theft actually happens.

We also raised open structural questions without clean answers: would meaningful crypto protection look more like an SIPC- or FDIC-style backstop limited to regulated exchanges, leaving individual wallets and small business crypto holdings uncovered? And a genuinely novel wrinkle for insurers used to receiving and investing stable currency: if a policy were priced and paid in crypto itself, insurers would be newly exposed to the currency’s own volatility on top of the underlying risk being insured — a combination Jay noted the industry has no real precedent for handling.

What’s Next: DeFi, Not Crypto Directly

Asked about future show plans, Jay said a dedicated crypto insurance show wasn’t likely, but a decentralized finance (DeFi) show was a near-certainty. He’s also increasingly interested in electric vehicle and mobility infrastructure — specifically framing “infrastructure” much more broadly than its traditional definition of repaving roads, extending it to whether current roads and networks can actually support an autonomous, electric, and eventually partly airborne transportation future. He connected this directly to federal infrastructure funding (noting that only roughly $1.5-1.8 trillion of the widely cited topline figure is actually earmarked for infrastructure specifically, with funds not expected to start flowing until mid-2022), and argued this is inherently a public-private problem: neither government alone nor the private sector alone can solve charging infrastructure, road capacity for autonomous vehicles, or the local/regional “edge computing” deployment gap that cloud infrastructure alone can’t close for latency-sensitive use cases like autonomous vehicles.

He tied this to the emerging concept of a “digital twin” — not just a road or a truck itself, but a full digital representation of a vehicle’s systems, cargo, and real-time state, foreshadowing a planned future conversation about commercial trucking, where risk is increasingly a function of the vehicle’s own technology and semi-autonomous systems rather than purely the driver behind the wheel.

Advice: Go to the Events, and Don’t Lose the Plot

Asked for a closing recommendation — the same question posed the year prior — Jay gave largely the same answer on purpose: attend ITC, Blueprint, or Manifest directly, because the relationships and connections built there compound over time. His more substantive advice for founders: don’t get hyper-obsessed with funding milestones as the goal in themselves, and stay relentlessly focused on solving a genuine pain point for someone — regardless of whether your specific angle is capacity, capital, or customers, solving a real problem is what ultimately attracts all three.

Key Takeaways

• A recurring theme from ITC 2021 conversations was capacity, not technology — multiple founders reported their most important meetings were with reinsurance and capacity partners, prompting Connective to consider a dedicated capacity-focused mini-summit at a future ITC
• Blueprint (real estate tech) and the newly launched Manifest (logistics tech) reflect Connective’s broader bet that insurtech, proptech, and logistics tech investment are adjacent, overlapping categories rather than separate verticals — evidenced by companies like Hippo and Rhino straddling insurtech and real estate tech simultaneously
• A pitch that leads with “we are an AI company” without naming a specific functionality (what’s being predicted, classified, or recognized) is a red flag; genuine differentiation comes from a laser-specific value proposition, illustrated by Relativity6’s shift from broad churn prediction to focused commercial classification coding
• Crypto insurance remains structurally difficult because crypto assets are purely digital from inception, breaking insurance’s traditional assumption of insuring physical things or digitized versions of them — with open, unresolved questions around wallet-level coverage, exchange-level SIPC/FDIC-style backstops, and the novel problem of insurers being exposed to currency volatility if premiums were paid in crypto itself
• Workflow tooling (not just connectivity/marketplace tooling) is what actually makes technology integrations useful in practice — a lesson drawn from both InsuranceGIG’s real-world use cases and personal experience underestimating Zapier for years before actually adopting it
• “Infrastructure” is being meaningfully redefined beyond repaving roads to include whether current networks can support an autonomous, electric, and increasingly airborne transportation future — a problem requiring genuine public-private collaboration rather than either sector alone
• The consistent, repeated advice across two consecutive year-end conversations: prioritize relationships over funding milestones, and stay focused on solving a real, specific pain point, since that is what ultimately attracts capacity, capital, and customers alike