Angel Fest 2025 brought together investors, community leaders, and builders, and this year’s insights did not disappoint. From the power of storytelling to the subtleties of company culture, the conference was packed with fresh perspectives, hard-earned lessons, and calls to think deeper about the work we do. Here are some of the standout moments we’re still thinking about.
Lessons from 100+ Checks with Daren Cotter
In his spotlight session, experienced angel investor Daren Cotter pulled back the curtain and revealed what he's learned after writing more than 100 checks. His approach emphasized not only listening and adapting, but also performing strong, thorough due diligence and understanding the law of probability.
Daren stressed the importance of diversification in your portfolio as an angel investor. Betting on one big win is risky, but creating a well-diversified portfolio not only increases your chances of success, it reflects disciplined, long-term thinking. One of Daren’s go-to questions when looking at a deal is a reflection that means something different for everyone:
“If everything goes right, can this be a big company?” — Daren Cotter, Angel Fest 2025
Poolside Chat with Monica Nassif
Our first headliner, Monica Nassif, founder of Mrs. Meyer’s Clean Day, reminded us that a brand is far more than design and messaging, it's identity. She built the iconic natural cleaning line not around a product, but a person, her mother.
Monica emphasized the importance of emotional resonance, shared values, and lifestyle alignment. These elements gave the brand its lasting power in a competitive market.
We learned that your brand isn’t just your logo, it’s the feeling people get when they interact with your company. When looking back on what it really took to create the Mrs. Meyer’s brand, Monica said it best:
“Make sure to invest in it early… Get the basics right and then stick to it.” — Monica Nassif, Angel Fest 2025
In order to create something real and lasting, it’s important to root it in the individual experience. Oh, and don’t even get her started on work-life-balance!
Poolside Chat with Chuck Runyon
Our second headliner, Chuck Runyon, co-founder and CEO of Anytime Fitness, unpacked how cultivating a “culture of care” enabled Anytime Fitness to scale globally without losing its core. From franchisee alignment to internal leadership, the company’s growth was directly tied to the intentional way they built and nurtured their culture. In fact, Chuck painted this ideal powerfully:
“You start focusing less on product and more on people.” — Chuck Runyon, Angel Fest 2025
We learned that if your values don’t show up in the day-to-day behaviors of your team, you don’t truly have a company culture. While most of the startups you invest in won’t have a tattoo parlor giving out free tattoos of the company logo, Chuck challenged us to redefine what putting people first looks like. Culture isn’t an HR initiative, it’s what gives you a competitive edge.
Invisible Threads with Joe Toscano
Joe Toscano, author, technologist, and featured expert in Netflix’s The Social Dilemma, challenged us to consider the deeper implications of the products we build.
He explored the invisible forces shaping our world: data privacy breaches, and protecting companies against these tech infrastructures. Joe reminded us that the digital world isn’t neutral, and the decisions made by founders and funders have a rippling effect. The best startups don’t just solve visible problems, they consider the invisible systems behind them. As he states:
“The fact of the matter is, anything that we're building nowadays that is digital in some sense is connected to the internet. And all the investments you make feed into a larger data set, whether you're thinking about it or not.” — Joe Toscano, Angel Fest 2025
Rookie to Rainmaker
In the Rookie to Rainmaker panel, the discussion highlighted the many contrasts and surprising overlaps between investors. The conversation revealed how fresh perspectives often challenge conventional thinking, while experienced voices provide wisdom rooted in years of investing. Each investor brought a unique background, sharing compelling stories ranging from early-stage wins to hard-learned lessons. This mix of insight created a dynamic dialogue on what it takes to evolve from a first-time investor into a confident, strategic rainmaker.
Unleashed and Unbound
The Unleashed and Unbound panel not only explored the medical industry, but Rochester as a whole and how the city continues to foster cutting-edge advancements, pushing the boundaries of what qualifies as healthcare. From tech-driven treatments to holistic care models, the message was clear: opportunity lies in reimagining what’s possible.
Dilly Dilly
The speakers on the Dilly Dilly panel shared valuable insights into the steps investors take when evaluating opportunities during their due diligence process. While some strategies mirrored those of others on the panel, unique approaches and personal touches underscored how due diligence varies from investor to investor, shaped by experience, industry, and risk tolerance. Rebecca Kahnweiler, Managing Partner of LongJump, states:
“We bring total transparency to the process, if we don’t invest we will tell you why. Our feedback is also very specific, so founders know the areas they can improve on.” — Rebecca Kahnweiler, Angel Fest 2025
Proceed Toward the Exit
The Proceed Toward the Exit panel took a deep dive into the complex decision-making process behind exits. Whether it's selling, merging, or stepping aside, the timing and rationale can vary widely. Panelist Katrina Anderson, founder of Clinician Nexus, remarked:
“The angel investing landscape today is very different from when I was raising capital. We had to make a clear decision, either get serious with an investor ready to write a check or walk away.” — Katrina Anderson, Angel Fest 2025
Some panelists spoke of exits driven by data and calculated risk, while others shared stories of gut instincts. The key takeaway: knowing when to walk away can be just as critical as knowing when to invest, and there’s no one-size-fits-all strategy.
Angel Fest 2025 wasn’t just another event, it was a recalibration. Whether you’re a first-time investor or have been steadily building your portfolio, the message rang clear, in a fast-moving world, the fundamentals still matter. Brand, people, integrity, and curiosity remain at the center of what makes a startup worth backing. And it’s the investors who slow down to build with purpose, not just speed, who are best positioned to shape what’s next.