Every CEO talks about AI. Few can show a direct, measurable ROI. My guest on The Scaling CEO, Josh Dater, saved more than $1 million by actually implementing it.
Josh is the co-founder and CEO of Inventory, a platform that helps wine collectors and restaurants manage their collections with precision and personalization. He’s a rare blend of product thinker, engineer, and entrepreneur, holding master’s degrees in both Entrepreneurship and Artificial Intelligence. His story shows what happens when technical skill meets business instinct.
From Product Builder to CEO
Josh spent five years as Chief Product Officer before taking over as CEO. That shift forced a new kind of thinking.
“As a product person, I believed that if we built the best possible product, it would sell itself. But when I became CEO, I realized distribution is the other half of the game.”
For CEOs who grew up in engineering or design, Josh’s advice is simple: a perfect product without a go-to-market engine is just an expensive prototype.
Knowing If It’s Product-Market Fit or a Scaling Problem
When revenue stalls, most CEOs ask: Is it the market or the execution? Josh says the answer lies in both data and instinct.
“You can see product-market fit in churn, conversion, and ARR—but you also need to listen to what people say. Are you getting niche criticism or broad rejection? That intuition matters.”
He built a feedback loop that filters noise through surveys, helping his team distinguish useful data from isolated opinions. For CEOs, this is the discipline of focus—knowing what to fix, and what to ignore.
The Calm of Resilience
Josh’s first business lessons came from his father, who reminded him, “It’s just money. It’s just business.”
That perspective shapes how he leads through turbulence. “The companies that win are simply the ones that stay in market the longest,” he says. Patience, not perfection, is often the real advantage.
Revenue Obsession vs. Mission Connection
Josh admits he checks the revenue dashboard every morning. But he also knows metrics don’t build purpose.
“We’re transparent with our employees. We share great customer feedback in Slack every day and show the P&L monthly. They need to see how their work connects to both mission and margin.”
Purpose-driven transparency fuels retention and motivation, especially in small teams.
The Pivot That Changed Everything
Inventory started as a tool for individual collectors. As Josh expanded into restaurants, he learned that business buyers behave completely differently.
“It’s a different type of customer. Their buying behaviors, product needs, even margins, everything’s different.”
He started asking a simple but powerful question: “Why did you buy this?” The answers revealed new use cases and unexpected growth opportunities.
Vincent: The AI Sommelier
Inside the platform, Josh’s team built “Vincent,” an AI-powered wine assistant that curates bottles, plans events, and helps collectors rediscover what they already own.
“Vincent isn’t here to replace sommeliers. He’s here to assist them. You still need a nose and a mouth to taste wine.”
Even professional sommeliers use Vincent as a shortcut for narrowing choices before applying their own expertise. It’s AI as augmentation, not automation.
The $1 Million AI Efficiency Play
Where AI has transformed Inventory, most of it isn’t customer-facing. It’s internal.
The company manages a database of over two million wines and processes 1,500 new entries each week. Previously, they outsourced data cleanup and enrichment to contractors.
“Now AI runs duplicate detection, fills in missing data, region, price, critic scores, and then our in-house sommelier verifies it. We used to outsource all of this, and it cost over a million dollars. We’ve cut that entirely.”
For CEOs, this is the real power of AI: operational ROI.
Final Takeaway
Josh Dater’s story is proof that AI’s biggest value comes when it’s baked into your business, not bolted on. Whether saving a million dollars in labor or building tools that deepen connection, his journey shows what happens when innovation serves strategy, not the other way around.
I’m Glenn Gow. I coach CEOs who want to scale smarter with AI. On my podcast, I uncover the strategies top leaders use to turn innovation into real, measurable growth.
Listen to the full episode of The Scaling CEO with Josh Dater for lessons on scaling, intuition, and how AI can make small teams unstoppable.
