Forging Forward: Scenes and Sentiments from Rise of the Rest’s 2024 Founder Retreat

We gathered 50 founders from across the country for 36 hours of connection and candor in Alexandria, VA, and no surprise: We left inspired.

At Rise of the Rest, our boots on the ground approach is one of our biggest points of pride. We believe place matters, and that there’s no substitute for meeting founders where they are, in the ecosystems they’re building within. But there’s also no substitute for gathering those founders in a room full of their peers, which is exactly what we did at the end of September at Hotel AKA in Alexandria, VA.

We kicked off our 2024 Founders Retreat with remarks on the setting and its significance from Amazon HQ2 Head of Policy, Brian Kenner. Alexandria — a historic city just across the Potomac from our nation’s capital — is part of the larger ecosystem locals lovingly refer to as the “DMV” (D.C., Maryland, and Virginia, not the Department of Motor Vehicles). Amazon selected Northern Virginia as its second headquarters in part for its proximity to policymakers, but also because of the diverse and growing tech community in and around the Beltway. Brian’s take: “There aren’t walls between state lines. Our communities are porous — D.C. might be at the center, but HQ2’s location has given us a reach that spans from Baltimore to Richmond.”

Steve Case set the tone for day two, sharing why most entrepreneurial stories aren’t overnight successes, but the product of years, if not decades, of perseverance. A takeaway from his experience building AOL: Endurance is underemphasized. “The adage was always ‘keep your eyes on the light at the end of the tunnel.’ The problem was, they kept adding more tunnel.”

Anne Mahlum got us fired up and ready to go with lessons from founding Back on My Feet and starting, scaling, and selling Solidcore. The new morning mantra: “People are going to tell you your idea isn’t going to work. Their doubts are a reflection of what they believe isn’t possible.”

Jamie Rodota kicked off a relay conversation with Source’s Nicole Schmidt, Starday’s Chaz Flexman, ViuHealth’s Melanie Igwe, Understory’s Alex Kubicek, Unreal Estate’s Kyle Stoner, and Sigo Seguros’s Nestor Solari about what the last year taught them about themselves and their teams. A common thread: resilience.

CAVA CEO Brett Schulman shared hard-earned wisdom on growing up with your startup, building culture into the company, and preparing to go public. “The business you’re running today isn’t the business you’ll be running tomorrow. It’s like going from driving a speedboat to steering an aircraft carrier.”

We broke from programming to move our bodies, letting founders choose their own adventure. On the menu: restorative yoga, exploring Alexandria’s sights and history by bike, and self-guided R&R.

Steve Case sat down with NACIE co-chair, Under Secretary of Commerce for Intellectual Property, and U.S. Patent and Trademark Office Director Kathi Vidal to discuss how founders can harness, leverage, and protect their startups’ innovation. A salient note on approaching partnerships: “Trust is important, but if you don’t have IP, it’s hard to collaborate and know what each partner brings to the table.”

Founders broke into stage-specific sessions on adapting roles and teams for growth — a winning formula for candid conversations.

For the final fireside of the day, David Hall sat down with StockX Co-founder, President, and COO Greg Schwartz, who brought his sneaker game and insights on staying true to the company’s values, vision, and birthplace. “Detroit didn’t fit into many investors’ ‘theses.’ But Detroit was where I was born and raised. There is tremendous loyalty to the city, and StockX employees feel like they’re playing a part in its revitalization.”

Peer power hour, dinner, and drinks followed. Few things rival the depth and understanding of founder-to-founder dialogue. Having the opportunity to facilitate some of those connections is one of the best parts of the job.

Revolution Chief Communications Officer Tracy Van Grack and Superfiliate CEO and Rise of the Rest Venture Partner Andy Cloyd kicked off day three’s agenda with thoughts on the new playbook for founder brand building. Andy, who’s cultivated an engaged following and arsenal of personable, value-driving LinkedIn content, knows getting started is often the hardest part. “Uncomfortability with how something might be perceived is what keeps most founders from putting authentic content out there.”

Your Washington Office founder Evan Burfield shared why we’re seeing a wave of Big Tech and VCs setting up shop in D.C., and how startups can navigate and capitalize on new regulation. “Solving today’s thorniest problems demands tech and government collaboration. Understanding tailwinds in Washington and telling your startup’s story in a way that rides those tailwinds is key.”

We closed out the Retreat with a moment of gratitude and a call to keep the conversations sparked within the walls of Hotel AKA going well beyond them.

Getting the portfolio together — and then getting out of the way to let founder-to-founder candor flow — always fills our cup. We’re so grateful for the time, presence, and perspectives every entrepreneur contributed, and even more excited for those connections to continue.