Inside the Build vs. Buy Decision: A Conversation with Tom Weist, AFV Advisor

October 2026

In the following interview, Stephanie Mueller, Head of Programs and Partnerships at American Family Ventures, speaks with Tom Weist, seasoned insurance industry executive and part of the American Family Ventures Advisory Network. The conversation highlights Tom's perspective on how he approaches the Build vs. Buy consideration, crucial components of successful partnership, and other points of advice for founders.

SM: You have had quite an impressive career in the insurance industry, can you share an overview of your background?

TW: I've spent more than 25 years in the insurance industry, primarily at the intersection of finance, actuarial science, risk management, and strategy. I am now retired, but most recently I served as Executive Vice President and CFO at Tokio Marine HCC. My responsibilities spanned everything from financial reporting and capital management to M&A, innovation, and the application of predictive analytics across the business.

What has been consistent throughout my career is a focus on helping organizations make better decisions through data and risk insights. Earlier in my tenure at Tokio Marine HCC, I served as Chief Actuary. I also spent time at Chubb in predictive modeling.

Despite now being retired, I have a hard time keeping my distance from the industry. I am involved as a mentor with Creative Destruction Lab, helping early-stage startups scale and commercialize. I also have the pleasure of serving as an advisor to founders in your team's portfolio with the AFV Advisory Network.

SM: I know I speak for many when I say we are deeply grateful that you still find yourself giving back to the industry! You've long been an advocate for providing early-stage startups an opportunity to do business with large enterprises. Can you share your philosophy when it comes to evaluating and adopting emerging technologies?

TW: I feel strongly that new technology must do one of three things for insurance: 1) lower loss ratio, 2) lower expense ratio, or 3) improve risk profile. Contrary to common thinking about CFOs, I did not look at new technology as an expense. ROI was always the primary measure. For example, will this company help improve underwriting or claims outcomes? Will it make a process more efficient? That frame of mind is crucial in order to get comfortable with evaluating new technology solutions.

SM: To that end, how do you think about the classic "build vs. buy vs. partner" equation?

TW: It's no secret that startups are far more flexible and fast than legacy insurers. If we can test cutting edge tech and get ahead of competitors, that's the advantage that startups offer insurers by way of partnership. In some cases where it makes sense, investing alongside that partnership creates additional benefit. If a market solution exists for standard operational functions and we don't get any ROI from building, that's when buying comes into consideration. Building is applicable when a proprietary capability could provide long-term competitive advantage.

SM: What are mistakes you've seen startups make during the early days of a partnership?

TW: You have to be crystal clear about what your objective is and define the end goal up front. There is such a thing as being too flexible. For example, tweaks to functionality are great, but adding a whole new product is a red flag. Being too flexible in your offering can slow down a POC and then everyone involved gets frustrated.

SM: To balance out that thought, how did you define success when it came to partnerships?

TW: It varies by use case. For example, new data to be used in underwriting would have to increase lift in models. This potential improvement in loss ratio could then be compared to the cost of the new data ingestion. Overall, when looking at a process improvement, the actual time or cost savings would need to be higher than the cost to implement. You see the theme here- ROI is always top of mind.

SM: Looking back, what separated pilots that successfully scaled from those that didn't gain traction?

TW: Trust and relationships are crucial, and clear communication is key to that. If there's a positive relationship sustained with the internal team, that will keep momentum going. That said, some degree of organizational resistance is a common challenge in large enterprises. Finding the right conduit within the organization to champion the work will make things far more efficient.

SM: Any advice to share with founders?

TW: The best founders don't overpromise or hide product deficiencies. If their software can't handle a specific legacy issue, they admitted it upfront and worked diligently on a workaround. They view the enterprise not just as a logo on their website, but as a true partner. They are obsessively focused on the business outcome, understanding that impact on the P&L matters most to business leaders.

SM: Is there any piece of advice you want to offer enterprise leaders?

TW: Traditional approaches don't always work well for early-stage companies, and establishing a partnership often requires flexibility. The best partnerships happen when both sides are willing to learn from each other and work toward a shared outcome.

Read on for more detail on Tom's background. If you have questions about the AFV Advisory Network, reach out to Stephanie at [email protected].