Todd Gray, Founder and CEO of ValueInsights.AI

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Todd Gray, Founder and CEO of ValueInsights.AI – 1st Mondays Mini Podcast

Posted: September 9, 2026

By Ella Napata

In this episode of the Startup San Diego 1st Mondays Mini Podcast, we chat with Todd Gray, Founder and CEO of ValueInsights.AI. An accountant by trade, Todd shares how his web-based AI application is simplifying non-cash contributions for taxpayers and tax preparers, and why he believes a strong product doesn’t need a hard sell.

Quick Summary

AI-powered valuation for non-cash donations: ValueInsights.ai is a web-based, AI-backed application that helps taxpayers determine the best possible value for non-cash charitable contributions, simply by snapping a photo.
Built to serve everyone in the transaction: The platform is designed to benefit three groups at once — the taxpayer making the donation, the CPA or tax preparer filing the return, and the charity receiving the contribution.
At First Mondays to build visibility: Todd sponsored a table at the event specifically to introduce ValueInsights.ai to the community and give the product some early exposure.
San Diego’s tight-knit ecosystem stands out: Coming from an LA-based perspective, Todd highlights how friendly, inclusive, and supportive San Diego’s business community feels compared to larger markets like LA or San Francisco.
The real challenge is introduction, not the product: Todd believes the product “stands alone” once people understand it; his biggest challenge as a founder is simply getting it in front of people and educating them, since the value becomes obvious once they try it.

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What Is ValueInsights.ai?

Todd describes ValueInsights.ai in simple terms: a web-based application, backed by AI, that helps people accurately value non-cash charitable contributions. Instead of guessing at a donation’s worth, users can snap a photo of an item and get the best possible valuation for tax purposes. It’s a straightforward solution to a famously unglamorous problem, as Todd jokes, referencing his father’s old saying about the only two guarantees in life; his product at least helps with one of them: taxes.

A Product Built for Everyone in the Chain

One of the most distinctive aspects of ValueInsights.ai is that it’s designed to serve multiple stakeholders in the same transaction. Taxpayers get an accurate valuation for their donations, CPAs and tax preparers get cleaner documentation to work with, and charities benefit from smoother, better-documented contributions. Todd emphasizes that everyone involved derives value once they try the tool.

Why Todd Participates a 1st at First Mondays

Todd’s presence at the event wasn’t incidental; he sponsored one of the tables specifically to introduce ValueInsights.ai to the Startup San Diego community. For him, events like this serve a dual purpose: genuine networking and a low-pressure way to put the product in front of new people who might benefit from it.

Why San Diego’s Startup Community Stands Out

Toof points out that San Diego’s business community is tight-knit, friendly, inclusive, and genuinely supportive of one another. For founders navigating what can be a lonely path, Todd sees that sense of community as a real asset, echoing the “family” feeling often associated with Startup San Diego.

The Real Challenge: Introduction, Not Selling

When asked what keeps him up at night, Todd doesn’t point to product gaps or competition. He points to introduction. In his view, ValueInsights.ai stands on its own once people understand what it does: snap a photo, get the best possible value. His approach is to educate first and let the sale follow naturally, rather than push a hard pitch. It’s a philosophy he ties to product-market fit: when a product is genuinely good, it doesn’t need to be forced on anyone.

Connect with Todd

Connect with Todd on LinkedIn and learn more about his product at www.valueinsights.ai. True to his accounting background, Todd keeps his branding simple and consistent across every channel.