Founders and Funders: Riley Rodgers

We had a great time at this month’s Founders x Funders AI Series at Pilot HQ, where we hosted a fireside chat with Riley Rodgers of Valia Ventures. Riley sat down with Cole Levin, our Head of GTM for CFO Services, for a candid conversation on what makes AI startups durable and why the next big win might come from a business that doesn’t look like an AI company at all.

If you’re building in or around AI and missed this one, here’s what you should take with you: 

1. The market is split and only a few will make it.
66% of venture dollars this year are flowing into AI. But most of that is chasing a small group of breakout companies. The rest of the startup world? Struggling to raise. Riley's take: being in the “right category” isn’t enough, you need to be exceptional.

2. “Boring” businesses are a hidden opportunity.
Forget building another flashy AI wrapper. Riley spotlighted founders embedding AI into traditional industries: janitorial services, financial ops, healthcare delivery, and outperforming the market– the businesses that make up the great majority of US GDP. The future’s not just in pure AI products; it’s in applying AI where others haven’t looked.

3. Valuation discipline is back.
Seed rounds at $50M+(or even $100M+) valuations aren’t flying like they used to. Mid stage rounds like Series B benchmarks are steeper, and growth alone won’t cut it, investors are demanding efficiency and real traction. The bar is higher across the board.

4. Founder mindset matters more than pedigree.
Some of the most promising companies today are being built by 20-year-old college dropouts; others by experienced operators. What they have in common: clarity of vision, ability to execute, and a bias toward speed. Riley put it best: “Head in the clouds, feet on the ground.”

5. How you communicate still matters.
A clean, thoughtful deck won’t raise your round, but a confusing one might get you ignored. Riley made the case that clarity isn’t just for investors, it’s for customers, hires, and momentum. If your story isn’t sharp, fix it.

Want a second set of eyes on your metrics or fundraising strategy?
Pilot’s CFO team has helped hundreds of startups raise from top-tier investors and we’d love to support you as you scale. Talk to us about how our CFO services can help, or keep an eye on our events hub for upcoming webinars and events.

We’ll see you at the next one.

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