Celebrating the Power of Peers and Paying it Forward

Against the vibrant backdrop of Chicago, Endeavor Great Lakes hosted a three-day retreat that connected Endeavor Entrepreneurs and Board Members from across U.S., followed by a staff retreat for teams from 10 of our offices across the North Atlantic. The event not only showcased Chicago’s flourishing entrepreneurial ecosystem but also facilitated profound connections and dialogues among founders. Attendees were treated to three days filled with thought-provoking discussions, and explorations of the city including an exclusive behind-the-scenes tour of Wrigley Field and a cruise along the Chicago River. The group also heard from a distinguished lineup of speakers and panelists who shared their insights and deeply personal experiences.

Let’s Get Personal: Andy Dunn’s Story of Success and Struggle, and the Changing Dynamics between Funders and Founders

The week kicked off with a conversation between Andy Dunn, Bonobos Co-Founder and author of Burn Rate: Launching a Startup and Losing My Mind, and David Cummings, Serial Founder, Investor, and Endeavor Atlanta Board Chair. Andy Dunn’s candid sharing of his entrepreneurial journey, marked by multiple successes and personal challenges, resonated deeply with the audience. He stressed the importance of mental health monitoring for entrepreneurs and the pivotal role it played in his own trajectory as both a founder and an investor.

Dunn emphasized the significance of encouraging entrepreneurs to prioritize their mental health: “I think it’s important to encourage people who are entrepreneurs to be in therapy, not just executive coaching – therapy. And there’s nothing shameful at all about mental health issues and mental illness. What is shameful is that as a society, we don’t enable people to bring their full selves to the table and a shame that we don’t work together support mental health issues.” He continued with encouraging reflections on Chicago’s emerging startup ecosystem, adding “I feel so lucky that I get to be a small part of the ecosystem, one that’s about to do it, where all the conditions are percolating.”

Beyond Silicon Valley: Lessons In Innovation from The Fresh Coast

Day two opened with a panel moderated by Tony Wilkins of Standing Oaks Venture Partners. Panelists Kevin Willer, General Partner at Chicago Ventures, Andrea Zopp, Managing Partner at Cleveland Avenue, and Steven Galanis, Co-Founder & CEO of Cameo, explored the strategies required to challenge the dominance of coastal tech hubs. They delved into Chicago’s unique journey in solidifying itself as a global destination for founders, innovators, and investors through decades of careful planning and a spirit of camaraderie among its entrepreneurs.

Kevin highlighted the necessity of growing Chicago’s tech ecosystem with successful companies: “At the end of the day, all that matters, the only metric is successful companies. And that sounds obvious, but we need to have some of these companies going public or getting acquired.”

Steven underscored Chicago’s distinctive startup environment: “Government and the big established companies have always done a really good job of propping up the startups in the ecosystem. And in Chicago, everybody really is totally thrown on the same team. It’s not a competitive environment and CEOs are friends with each other, they all invest in each other.”

This Story Has a Happy Ending: How Great Leaders Innovate Through Uncertainty And Failure

Day three of the retreat closed out with a session led by Kim Lewis, Co-Founder of CurlMix, featuring Sam Yagan, Founder of Corazon Capital and OKCupid, and Sandra Campos, a serial entrepreneur, CEO and board member. The discussion examined the crucial lessons learned at every stage of leadership growth, particularly during times of crisis, and the role of failure in shaping leaders.

Sandra Campos shared her perspective on the benefits of failure: “I’ve had so many different types of failures. I can now see what’s around the corner and ask those questions like, ‘Did we think about this?’ A lot of times people don’t think about the ‘what if.’’

Sam Yagan stressed the importance of investing in team culture ahead of a crisis: “Investing in culture ahead of time is key. When people are truly bonded, that’s when they come up with their own ideas to help during a crisis.” Yagan also highlighted the significance of mentors and coaches, emphasizing their role in helping leaders make tough decisions with confidence: “I have found that coaching and mentorship are both things that I’ve relied on to help me grow as a leader. I think once you become a CEO, it’s hard to grow without being very intentional. Making a tough decision is the reality. Oftentimes I’ll go to a coach and it makes me less worried about what decision to make.”

The Power of Paying it Forward

The Endeavor U.S. Retreat was an extraordinary convergence of entrepreneurial minds, but more than that, it reiterated the impact successful entrepreneurs can have when they inspire, mentor, and invest in the next generation of founders. The spirit of the Multiplier Effect was on full display through our Endeavor portfolio Entrepreneurs who have taken board seats in their local offices, and through our inspiring speakers who took the time to share their stories. As our teams departed Chicago, we were all freshly inspired by the power of the “pay it  forward” mindset. And as one attendee put it, “It’s always about more than ‘networking’ or ‘drinks’ or ‘ecosystem dinners. It’s breaking bread with people you can trust.”