Introduction:

In this episode of The First Customer, I had the chance to sit down with Jay Aigner and talk about my journey from corporate CTO to startup founder. We explored how my upbringing shaped my entrepreneurial mindset, what I’ve learned from both wins and losses, and why I now focus on building tools that help founders get investor-ready faster. I shared how I earned the name “Hurricane CTO,” how I approach chaos with calm, and why branding, systems, and empathy are essential to innovation. It’s a conversation rooted in real experiences—from missed deals to launching a product used by founders and accelerators around the world.

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Key Topics Covered:

Why I Call Myself the Hurricane CTO

The nickname started at the LA Clippers, where I earned a reputation for running into chaos—whether it was a network outage or a last-minute crisis—and finding order quickly. It stuck. Over time, I embraced it as a brand, one that reflected my ability to lead through turbulence with calm, clarity, and execution. It’s become part of how I show up, and part of the message I share with others who face high-pressure decisions every day.

Learning from a Missed Acquisition Opportunity

One of the most impactful failures in my career came during an acquisition deal that I couldn’t quite make work. I struggled to articulate the value from a tech and investment lens, and we ended up walking away—only to see the company double in value months later. That loss drove me to build a framework for evaluating businesses and opportunities, a toolset that eventually became Investimate.

How My First Business Was About Solving Real Problems

My entrepreneurial spirit started young—launching a paintball gear company in middle school so my friends and I could get wholesale prices. That drive to solve real problems never left. Whether working at UTA, launching startups, or building Investimate, my focus has always been about finding product-market fit by understanding what people actually need—and delivering solutions that make sense.

Building Investimate to Help Founders Succeed

With Investimate, I wanted to lower the barriers for anyone with a good idea but no clear path to funding. Using AI, we help founders validate their concepts, build investor-ready decks, and understand their startup’s value—without needing a business degree or a technical cofounder. We’ve partnered with organizations like UCLA’s accelerator and are working to expand globally with initiatives like grant support via the UN. For me, it’s about scaling access and giving people the playbook I wish I had earlier.

Conclusion:

My path—from corporate leadership to launching Investimate—has been full of chaos, learning, and reinvention. I’ve failed, rebuilt, and created frameworks to help others avoid the same missteps. Whether I’m leading a tech team, advising a startup, or building a platform, I always return to the same principles: lead with empathy, build systems that scale, and don’t shy away from the hard stuff. I hope this episode gives founders, investors, and operators something useful to take with them—because if I’ve learned anything, it’s that the first customer is just the start of the real work.

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