Don’t Raise Just Enough to Get By. Raise What You Need, Plus Some, and Stop Playing the Market.

Dave Wechsler came into insurtech sideways — five years before this recording, working at Comcast on Smart Home technology, not insurance. As he learned about applications of smart home tech to insurance (Hippo among the companies that eventually emerged from that space), he started networking specifically to find people who could teach him the industry rather than trying to learn it purely from documents and reports. That instinct — that the real education happens in casual conversation, not just conference sessions — became the origin of InsurTech RAP, the live, informal community show he now runs alongside his day job.

In Episode 97 of InsurTechTalk, Dave and I covered why he thinks insurtech’s “first act” is closing (and why that’s a genuinely good thing), the mechanics of his newest and first self-led investment — an E&S-focused MGA called Join — and why he considers bridge financing one of the worst instincts a founder can act on in a down market.

About Dave Wechsler

Dave Wechsler is a Principal at OMERS Ventures, the venture arm of OMERS — one of Ontario’s public pension funds, managing roughly $120 billion in total capital, with roughly $2 billion allocated to venture investing specifically. OMERS Ventures is a generalist investor with offices in the San Francisco Bay Area, Toronto (headquarters), and London, typically investing Series A through Series C with check sizes of $5-25 million. Dave focuses on insurtech and fintech within that mandate and also hosts InsurTech RAP, a live, informal weekly community conversation for insurtech investors, founders, and industry members.

AI and the Coming Change to Compliance and Law

Before getting to insurance directly, Dave and I spent real time on a legal-AI tool he’d encountered that morning — one capable of summarizing a 50-page contract into plain English (“explain it to me like I’m a kindergartner”) and proactively surfacing the top negotiation points. Dave’s genuinely bullish read: AI won’t eliminate roles in law or compliance, but it will change their nature — a large share of legal work is interpreting a client’s situation into precedent and applicable language, and as models improve, the gap created by imperfect human translation between client and lawyer shrinks. His more provocative extrapolation: he could see AI eventually taking a contract and a factual situation and rendering an objective determination of which party is at fault, based purely on the contract’s language — a genuine shift in how disputes get resolved, not just how agreements get drafted.

My pushback, grounded in caution appropriate to my own compliance obligations as an investment banker: we’re still early, and the skill shift matters as much as the capability shift — the emerging requirement isn’t just “can AI read a document,” it’s “does the human operating it know how to ask the right question to get a reliable answer.” We agreed this reframes what a modern insurance agent or lawyer’s actual skill set needs to include.

How InsurTech RAP Started

Dave’s account of the show’s origin is genuinely bootstrapped: in fall of the prior year, he emailed a group of contacts and ran an experimental hour-long live Zoom session on insurtech funding, featuring a panel of VCs, open to audience questions. It was, in his words, “awkward” and imperfect but generated enough positive response that he kept iterating — trying pre-arranged panels, open sign-up slots, different lengths and formats.

His explicit design philosophy: this isn’t meant to be an “experts talking down to an audience” format (he cited Twitter Spaces, with sessions drawing thousands, as inspiring in scale but ultimately too one-directional for what he wanted). InsurTech RAP is built around genuine audience engagement, speakers who wouldn’t necessarily headline a traditional conference panel, and space for people to share opinions rather than only rehearsed, vetted talking points — with the explicit goal of building community, not lead generation for his own fund. His stated measure of success: if attendees at a major conference the following year know 50, 100, or 500 more people specifically because of relationships built through InsurTech RAP, he considers the project a success — independent of his own visibility as host.

Join: A First Self-Led Investment in E&S Underwriting

Among OMERS Ventures’ four core insurtech investments (Clearcover in personal auto, Foresight in workers comp, weFOX in European distribution), Join — an MGA focused on commercial excess and surplus (E&S) risk — is the one Dave personally led, closing in December of the prior year.

His explanation of why E&S specifically is structurally interesting right now: E&S covers non-standard risk that’s inherently harder to underwrite because it doesn’t fit standardized, homogenized models — and the category is growing precisely because traditional, standardized risks are getting displaced from the admitted market. Climate exposure and emerging risks like cyber and AI are pushing more business out of what a typical carrier’s standard buy-box and technology stack were built to handle, requiring bespoke underwriting few carriers are structurally set up to do efficiently.

Join’s team, led by CEO Saranya Messiah (25-plus years in insurance, largely at larger carriers) alongside other ex-AIG and ex-Hamilton executives, is deliberately insurance-first rather than tech-first — Dave’s phrase: “just enough tech to make them dangerous.” Their specific innovation: standardizing what has historically been an extremely bespoke, manual underwriting process. Dave’s description of the pre-Join status quo: E&S underwriters typically work across multiple disconnected workbenches, manually processing large volumes of forms and unstructured data before they can even begin underwriting judgment — meaning most of an underwriter’s time goes to prep, not risk assessment. Join’s platform pulls data in, augments it with third-party sources, and gets underwriters to the actual underwriting decision faster — a pattern Dave noted is already common on the admitted side, but genuinely rare in E&S specifically.

Why He’s Bullish: Insurtech’s “First Act” Is Ending

I asked Dave directly for his read on the funding environment, given the 2022 pullback and mixed early 2023 signals. His answer, delivered candidly as a “long punchline”: very bullish, but with a clear-eyed account of what went wrong first.

• Early insurtech entrepreneurs deserve genuine credit for bravery and vision, regardless of individual outcomes — some ideas worked, some didn’t, and even the “long shot” ideas that didn’t pan out had a legitimate role in testing what was possible
• Valuations got out of hand primarily because venture capital, structurally, wants to deploy large amounts of capital and — in Dave’s assessment — didn’t fully understand insurance economics at the time, encouraging entrepreneurs to think and raise bigger than the underlying unit economics could support
• Insurtech “led the way down” for venture broadly in the 2022 pullback, and Dave’s prediction (delivered with real conviction) is that it will also lead the way back up, because the “tourist” investors who never understood the space have exited, leaving behind investors genuinely committed to it
• The single most important signal he pointed to: carriers beginning to acquire insurtechs directly — regardless of whether any individual deal was a great outcome for investors or founders, carrier M&A activity validates the category and creates room (and confidence) for new founders and capital to re-enter

His specific caveat: MGAs that were priced too aggressively during the peak will struggle to raise, because nobody wants to be the one forcing a painful recap on a founder — but the broader trend he expects is a healthier, more capital-efficient MGA ecosystem emerging from the correction, with carriers themselves more motivated to adopt real innovation as MGA competitive pressure increases.

Why Bridge Rounds Are a Trap

This was the sharpest tactical advice in the conversation, delivered with real intensity. Dave’s direct warning to founders considering a bridge round specifically to “hang on until things get better”: that’s a mistake. His reasoning:

• Nobody can reliably predict when a down market ends — it could turn next quarter or persist for two years, and betting a bridge round’s timing against that uncertainty is a gamble, not a strategy
• If a company is genuinely healthy enough to raise, it should raise what it actually needs, plus buffer for a difficult one-to-two-year stretch — not the minimum amount to survive to the next inflection point
• His own career pattern-matching across five startups (three founded, two joined): a beautiful cap table with insufficient runway can still end in bankruptcy, while a genuinely messy cap table can still reach a great exit — there are too many variables to “game” fundraising timing, so the discipline that actually matters is building a fundamentally sound business, not optimizing valuation or dilution at any given moment
• His pointed real-time observation: founders who were anxious about raising in Q4 (when the market first turned) and delayed, hoping conditions would improve, generally made things worse for themselves — the market got harder, not easier, in the months after

Advice: Know Your Market, Then Run Hard at It

Asked for closing advice, Dave’s answer circled back to the same discipline: if you genuinely believe an idea will work, understand precisely how and why it will work, raise the appropriate amount of capital to make it happen, and then stop worrying about valuation, exit timing, or other “existential” distractions that founders can’t actually control. His pointed critique of the broader venture ecosystem over the preceding five to six years: VCs collectively pushed too much capital and encouraged founders to think bigger than warranted, which contributed directly to the correction. His genuinely optimistic closing framing: there’s no bad time to be an entrepreneur — the discipline is proving product-market fit is real, which doesn’t require being large or even profitable yet, just demonstrably working.

Key Takeaways

• AI-driven legal and compliance tools are likely to change both contract drafting and dispute resolution meaningfully, but the emerging human skill isn’t disappearing — it’s shifting toward knowing how to ask the right question to get a reliable answer
• InsurTech RAP’s design deliberately favors audience engagement and non-traditional voices over expert-to-audience broadcasting, built explicitly around community-building rather than lead generation
• E&S insurance is growing structurally because climate, cyber, and AI risk keep pushing business out of standardized admitted underwriting models that most carriers’ technology wasn’t built to handle
• Carrier M&A activity acquiring insurtechs directly is, in Dave’s view, the strongest positive signal for the category’s health — regardless of individual deal outcomes, it validates the space and creates room for new entrants
• Bridge financing timed to “wait out” a down market is a gamble on market timing nobody can reliably predict — raising sufficient capital to weather a genuinely difficult 1-2 year stretch is the more defensible discipline
• Neither an unusually clean cap table nor an unusually messy one reliably predicts startup outcome — fundamental business soundness matters more than optimizing financing structure at any single point in time
• MGAs that were overpriced during the 2021 peak will face real difficulty raising, but the broader correction is producing a more capital-efficient, fundamentals-focused insurtech ecosystem likely to be healthier over the medium term