Why I’m Joining SignalFlare.ai as VP of Product

I used to think the hardest part of building a startup was getting people to love your product. Then I built something thousands of people loved, and the real challenge was evolving it into a successful business.

In November 2022, I sent a 5-page post mortem to all thirty stakeholders who had supported the venture along the way with advice, capital, and labor. It explained in detail what we had accomplished and why it wasn’t enough. 

The crystallizing moment had come just two months prior, when the founding team was discussing twelve different business model frameworks I had listed in a Google doc with all the pros and cons of each. The models all were viable in one way or another. But it was too late. The trade-offs that came with each were too great. Subscription tiers? That meant building entirely new features. Marketplace take rates? We'd need to become a payments company. Advertising? Wrong user behavior patterns.

Every business model we explored required resources we didn't have or sacrificed the user growth that we hoped would suffice for raising another round. We'd been debating for over an hour, and the energy had shifted from optimistic problem-solving to something closer to dread.

IN., our social platform for group experiences, was an all-in-one play. We had power users who were using it weekly. We were growing 48% month-over-month at our peak. People were organizing international trips, planning local hangouts, and found it essential for bachelor(ette) parties. We'd raised just over $300K from respected investors and built a team that believed in the vision.

But we couldn't figure out how to generate revenue in a way that didn’t slow down our momentum.

On Entrepreneurship

That failure taught me something I couldn't have learned any other way: there's a universe of difference between building something people want and building something that wins in the market.

Whether you're launching a barbershop or the next billion-dollar tech company, the same three factors determine success, just at different scales:

The right people need to like you and want to help you. Your network opens the right doors, fills your talent pipeline, and gives you credibility while navigating the inevitable speed bumps.

Your product has to be exactly what the market wants or needs at that time. There's no product that overcomes being ahead of its time or being too late to the punch.

You have to be more creative, advanced, relational, and/or speedy than any competition. Sustainable advantages don't happen by accident.

These are the prerequisites you invest in to de-risk your journey upfront. We had a great vision and built valuable technology, but we didn't assemble the right network to fund us through the growing pains or find a way to find our wedge against a growing list of social apps going after the same market.

I've seen this pattern repeatedly: founders struggling to reach each milestone because one of these three pillars wasn't standing when they began.

So I spent the next three years learning how businesses actually win by helping over two dozen startups avoid my mistakes. Each project validated that my failure had taught me something valuable about how to bridge that gap between vision and execution.

The results have been gratifying and have validated the principles I’ve come to believe in. I doubled a YC-backed startup's outbound response rate by helping them understand their buyers in a structured way. I led the development of an AI product from 0 to 1 that won two fundraising competitions by staying focused on what would activate the company’s first sustainable revenue stream. I drove a 100% increase in ROAS for a Shopify store by establishing a system for experimentation that accelerated their learning loops. I generated hundreds of thousands in pipeline for a SaaS company by building their strategic alliances program from scratch that made them more viable upmarket.

My clients have included startups across SaaS, AI, consumer apps, ecommerce, and biotech – from pre-seed to Series B. Despite the variety, I started recognizing patterns. I could spot the founders who had all three pillars in place versus those who were trying to build them on the fly.

Which is how I recognized immediately when I met Mike Lukianoff that he had cracked the code I couldn't.

Choosing SignalFlare

Mike has been at the forefront of data science for restaurants for 30 years. He was on the team that invented econometric pricing for McDonald's and has since built and sold multiple companies utilizing his innovations. Today, you'll only hear positive things about his reputation with restaurant leaders. His work is lightyears ahead of any competition—it won Snowflake's startup challenge last year to prove it. And the hospitality market absolutely needs what SignalFlare is building.

When you're invited to join a founder like that, you're obligated to take it seriously. I took it a step further and signed my offer letter for two additional reasons.

First, I'm an AI optimist, though I didn't start that way. The sheer pace of AI disruption gave even prominent CEOs sleepless nights. It was no different for almost everyone I know – which AI course should I take? Will it be outdated in a month? Where is the puck going?

My optimistic take now is that AI gives us an opportunity to be more human. Imagine a restaurant CMO whose team currently spends three hours every Monday pulling data from five systems, then weeks figuring out how to make a data-informed decision on how to most efficiently spend their marketing dollars. With AI, that same data can be compiled in minutes, and the system can orchestrate workflows across knowledge bases to automatically generate actionable recommendations with accurate predictions about outcomes.

Instead of faster reporting, they get decision support that frees them to focus on the human side: calling underperforming locations, having real conversations with managers, thinking creatively about customer experience. That's AI's real potential – streamlining the drudgery so we can spend more time on what makes us human.

Second, I believe restaurants play an increasingly important role in our society. They represent one of the only remaining widely used third spaces where we can share our lives and connect with each other. At a time when IRL connection is waning despite increased URL connection, it seems a worthy endeavor to empower restaurant leaders — who specialize in the kind of hospitality that brings us together the way that I always envisioned IN. would — with this kind of next-generation technology.

The Next Chapter

Last week, I officially wrapped up four and a half years of entrepreneurship, first building my own thing, then helping others build theirs. My intention until a month ago was to continue growing my consulting business. Very few opportunities would convince me to leave behind a growing pipeline and reputation.

With Mike and his all-star team, I'll be building Agentic AI that gives restaurant decision-makers superpowers. SignalFlare is creating the 'restaurant decision intelligence' category by moving beyond analytics and business intelligence to AI-powered decision support. Our agents collapse the workflow from data to decision by taking complex industry datasets plus first-party restaurant data and making them actually useful for human decision-makers.

This frees restaurant leaders to focus their limited time and resources on what drives their business: food quality, service, atmosphere, and community connection.

After years of fractionally helping others build, I'm excited to again focus all my energy on building one thing in a new category for such an important industry.