We Talk Too Much About Technology and Not Enough About People

Jonathan Crystal opened the doors of Crystal Venture Partners on November 1, 2022. ChatGPT launched 30 days later.

That timing was not a coincidence — Jonathan had visibility into what was coming — but the proximity still captures something true about where he sits in this industry. Third-generation insurance operator, CFO of a top-25 national brokerage, sold the family business to Alliant, and then had the audacity — his word — to go raise $33 million and start writing checks to founders building the future of insurance and risk.

Eleven portfolio companies later, with over $150 million in follow-on capital raised across the portfolio in the first six months of 2026 alone, Crystal Venture Partners is producing results that speak for themselves.

In Episode 163 of InsurTechTalk, Jonathan and I covered the origin story, the investment thesis, what he actually looks for in a founder, why he thinks the InsurTech label is holding the industry back, and what the closing question of the episode produced — one of the most direct and important answers I have gotten on the show in 163 episodes.

About Jonathan Crystal

Jonathan Crystal is the Founder and Managing Partner of Crystal Venture Partners, a New York-based early-stage venture firm focused on companies at the intersection of insurance, risk, and technology. He is a third-generation insurance professional — his grandfather Frank Crystal founded Crystal & Company, and Jonathan rose through the ranks over two decades to become CFO before leading the firm through its acquisition by Alliant Insurance Services in 2018. Before launching the fund, he made personal angel investments in Flyreel (acquired by LexisNexis in 2022) and Corvus (acquired by Travelers in 2024), giving him two successful exits that validated his thesis before he raised a dollar of outside capital. Crystal Venture Partners Fund I closed at $33 million in October 2025, oversubscribed, backed by senior executives from global insurers, GPs from top venture funds, and family offices with deep insurance domain expertise.

Why He Does Not Believe in InsurTech Anymore

This was the sharpest reframe in the conversation and worth understanding carefully.

When people ask Jonathan if Crystal Venture Partners is an InsurTech fund, his answer is no. Not because he is not investing in the intersection of insurance and technology — he clearly is — but because the label itself is the wrong frame.

InsurTech implies technology that serves the insurance industry. That is a closed circuit. A fixed set of buyers. A defined market.

What Jonathan is actually investing in is companies that serve the world — and happen to be doing it through the mechanisms of insurance, risk management, and resilience. Bright Harbor is not just an InsurTech company. It helps families who lost their homes in natural disasters get back on their feet. That is a problem for every person on the planet who lives in a climate-exposed area, not just a problem for insurance carriers trying to manage catastrophe exposure.

The implication for the industry is significant. If we keep labeling everything InsurTech, we keep limiting our ambition to the industry itself. The better question — the one Jonathan thinks the whole sector should be asking — is not how do we build better insurance technology. It is how do we keep insurance relevant for the next 100 years.

Three Things That Make a Durable Business in an AI World

When I pushed Jonathan on what he actually looks for — beyond the founder, beyond the market — he landed on three structural characteristics that he believes define the companies that will win across any technology transition.

The Three Pillars

• Regulatory navigation: Regulated businesses that can operate within, be compliant with, and ultimately use the regulatory environment as a moat rather than a constraint have a structural advantage that technology alone cannot replicate
• Capital efficiency: The ability to access capital and deploy it efficiently — understanding that capital structure, not just revenue, determines the long-term health of the business
• Trusted customer relationships: In a world where software is becoming abundant and cheap, the relationship is the product. The companies that own the customer relationship and maintain trust through transitions will outlast the ones that own only the technology

Jonathan’s point is that the entirety of the insurance industry — in every form it has ever taken, from Lloyd’s coffee house to AI-native MGAs — has been built on exactly these three things. That continuity is not a bug. It is the reason the industry survives every technology wave and will survive this one too.

The Investment Model: Early, High-Conviction, and Intentionally Personal

Crystal Venture Partners writes checks between $1 million and $3 million, sometimes as early as day one behind a team with an idea. The fund targets approximately 15 companies from its $33 million pool. The math implies concentrated ownership and concentrated attention.

What That Means for Founders

• Jonathan typically takes an observer or participant role on the board, with material ownership given the early entry
• His most valuable contributions are not technical — he said so explicitly to a founder who tried to pull him into a tech stack conversation: “You didn’t bring me on to give you tech advice, did you?”
• What he actually brings: customer introductions, senior talent connections, capacity relationships, carrier appointments, co-investor relationships with funds like Lightspeed, Bessemer, Sequoia, Khosla, Brewer Lane, and Congruent
• His framing: “Every money is green. You should think about who’s the partner you want to have and what they bring to the table.”

He also described the investment relationship with a line worth stealing: “When we make an investment, it’s like marriage with no chance of divorce. Death or secondaries put us apart.”

The Gyde Story: Eight Months of Conversation Before a Check

Jonathan’s description of how he came to back Will Johnson at Gyde (Episode 153) is the clearest window into how he actually sources and evaluates deals at the early stage.

It was not a pitch meeting. It was eight to nine months of getting to know Will while he was still at Oscar Health — understanding what motivated him, how he thought about problems, what kind of business he would want to wake up every morning and run.

And then Will came back with a different idea than the one they had originally discussed. Not an evolution of the original — a genuinely different business. He wanted to acquire independent employee benefits agencies and layer AI on top of them to drive organic growth.

Jonathan’s response: it’s your business. Take it where you want to go. We want to be alongside you.

That posture — conviction in the person before conviction in the idea — is what makes seed-stage investing work. And it is why Jonathan spends the first few minutes of any founder conversation asking to skip the first six slides of the deck. He does not want to hear about the TAM. He wants to understand what unique insight the founder has that nobody else has, and whether they know how they are going to make money.

On Revenue Models and the Death of Pure SaaS

One of the more provocative positions Jonathan staked out was on revenue models. Crystal Venture Partners is explicitly revenue-model agnostic — and Jonathan articulated why with a line that will age well:

“When all software becomes disposable or abundant or cheap, you probably have to find something else to sell besides the software itself.”

His portfolio reflects this: Gyde makes money on commissions. Sixfold is structured around carrier outcomes. Other portfolio companies operate on gain-share models or services contracts. The unifying thread is that customers pay for outcomes, not for licenses.

His recovering-CFO framing for the token economy was equally sharp: labor on one side, tokens on the other, and the right answer is to put them on the same line item and let the business figure out the allocation.

Venture Capital Is the Most Expensive Capital You Can Imagine

Jonathan’s advice to founders thinking about raising venture capital was unusually direct — and important for the founders and operators in the InsurTech:LA audience to hear.

Venture capital carries an implicit expectation that every single investment can return the entire fund. Crystal Venture Partners has a $33 million fund. That means every $2 million check needs a credible path to returning $33 million. That is a 16x return expectation on every deal, not an average return target.

The implication: venture capital is structurally incompatible with building a good, sustainable, profitable insurance business that grows at 20% a year. It is specifically designed for companies that could be 100x outcomes. If your ambition is to build a great regional agency or a profitable specialty MGA, venture is the wrong capital source. If your ambition is to transform a category, it is the right one — but only if you understand what you are signing up for.

The Closing Answer: We Need to Talk About People

The final question — what should the industry be talking about that it is not talking about enough — produced the best answer of the episode.

Jonathan did not talk about AI. He did not talk about technology. He said:

“We are talking too much about technology and not enough about people. Because this technology is going to impact people. And the hard thing of an AI transformation is going to be about organizational change. Changing how people work and helping people navigate through that from a career perspective and a skill and knowledge development perspective. So I’d like to hear us talk about people much more than technology.”

For a fund that has backed AI-native underwriting, AI sales agents, and AI-powered brokerage — that is a striking answer. And it is the right one.

Key Takeaways

• The InsurTech label limits ambition; the better frame is how insurance remains relevant for the next 100 years
• Regulatory navigation, capital efficiency, and trusted customer relationships are the three structural characteristics that define durable businesses in an AI transition
• Seed-stage investing is about conviction in the person, not the deck — Jonathan spent eight months getting to know Will Johnson before writing the Gyde check
• Pure SaaS is under structural pressure; outcome-based and gain-share models are the future
• Venture capital is the most expensive capital available — it requires a credible path to fund-returning outcomes, not just a good business
• The hardest part of AI transformation is organizational change, not technology deployment