Portfolio Construction in the Age of AI | Rachael Richardson, Florida Funders

What we talked about.

Sunny Ray sits down with Rachael Richardson of Florida Funders to explore how AI is reshaping venture investing and where human judgment still matters. Richardson explains how the nearly 13-year-old platform builds the Florida and Southeast startup ecosystem, runs a network of about 3,000 investors, and manages funds including a pre-seed vehicle for Florida founders and a vehicle focused on a16z speedrun startups. She traces her path through Alumni Ventures and Volo Earth, describes what a standout founder looks like through the story of a vertical software company for laundromats, and explains why her firm favors second-time founders and operators whose judgment is embedded in how work is actually done. She also discusses why strong founders sometimes go unfunded when model releases and horizontal players erode their value. Richardson closes with a detailed look at check sizing from $500,000 to $2 million, reserves of 40 to 50 percent, and a three-bucket portfolio approach spanning speed-driven bets, early AI categories with acquirer demand, and small experimental positions.

A Florida Funders investor explains how she builds a venture portfolio when AI models can erase a startup's advantage overnight.

The questions, and the answers.

What problem is Florida Funders solving?

We work on two sides. Founders in Florida and the Southeast lacked an ecosystem of capital, advice, and customer connections to take the risk and build. Meanwhile, successful individuals in many industries lacked access to good startups outside the traditional hubs. We build the ecosystem for founders and connect investors to startups in Florida, the Southeast, and beyond.

Why did you choose Florida Funders after your earlier firms?

Alumni Ventures gave me breadth and pattern recognition, and Volo Earth gave me a hyper thematic, conviction-led framework. Florida Funders is a nice hybrid. It has a clear thesis across cybersecurity, vertical enterprise AI, and fintech, and I can bring value from day one. I also loved its people-driven, community-based approach and its leadership's drive.

What did the first deal you worked on teach you about a strong founder?

It was Alex Shikowski of Sense, vertical software for laundromats. His obsession with the product, industry, and customers shapes the whole culture. Every new hire spends a day in a laundromat with customers. He sells to customers, talent, and investors at each stage, and he balances humility and coachability with firm leadership, which is hard to do.

Why do you look for founders who have exited or led inside a market-leading company?

Taking a product from $1 to $5 million to something larger involves capital formation, pacing through market cycles, and building teams and systems. Second-time founders sequence those resources better. Leaders from market-leading companies know pricing, margins, and how work is really done. Knowledge embedded in workflows is more defensible against labs and horizontal players than knowledge written down.

How has the way you evaluate companies changed?

Humans love stories, and a pitch deck feels convincing as you nod along. Now I focus on dissecting that story. I ask whether it could be right, then identify the assumptions inside it. I test them by asking subject matter experts, customers, the founder, or a research agent to help parse out what actually holds up.

What is the most common reason a strong founder still does not get funded?

Mostly market dynamics. I have met great founders with prior exits whose growth was taking off, and you can trace the decline back to a model release that made their product far less valuable. Lab obsolescence, horizontal players, and absorption pressure, where a product quickly becomes a feature, are happening faster than ever.

How do you size checks and handle reserves?

We separate position-size checks that move the fund from smaller option checks that buy information and a seat for later. About 40 to 50 percent of the portfolio is held in reserves. Follow-on money has to be earned, because doubling down raises exposure but does not automatically improve returns, so we evaluate each additional dollar on a marginal basis.

How do you think about building a portfolio?

I think in three buckets. First, speed-driven categories where we accept slightly less ownership but de-risked go-to-market. Second, early AI industries where acquirers are already buying, giving higher ownership and a 10 to 20X floor. Third, small experimental bets with reserves around three times the initial check, held until specific assumptions and metrics tell us when to double down.