Key Leadership Lessons from Denver Startup Week: Navigating the Challenges of Leadership

Denver Startup Week (DSW) 2024 offered a vibrant platform for learning, connection, and growth within Colorado’s entrepreneurial ecosystem. As a proud advocate for the state’s startup and scaleup community, BEN Colorado was excited to play a prominent role in this year’s programming, aligning our mission of supporting founders and scaling companies with the energy and innovation of DSW.

Through three dynamic sessions, we brought together the knowledge and insights of our extensive network, giving attendees a glimpse into what BEN Colorado stands for: collaboration, mentorship, and compassionate, supportive real-world expertise. More importantly, we expanded our programming to reach more entrepreneurs across more stages in Denver and beyond, allowing us to engage with an even wider audience of entrepreneurs eager to learn, grow, and build businesses that matter.

In this recap, we’ll highlight key lessons that can benefit entrepreneurs, both here in Colorado and beyond.

Denver Founders VIP Founder Leadership Summit 

Mick Freeman, BEN Colorado’s CEO & Executive Director, kicked off the week alongside host Chris Franks as keynote speakers at the Denver Founders VIP Founder Leadership Summit. Together, they highlighted the unique qualities that set Colorado’s startup ecosystem apart, beginning with a “give first” mentality. This mindset of collaboration, mutual support, and a genuine drive to lift others up is at the heart of the state’s entrepreneurial community, creating an environment where everyone’s journey is intertwined and there is enough space for everyone to find success. “The pie is bigger when we collaborate to create more opportunities,” said Mick.

Chris and Mick didn’t shy away from candid discussions on two critical topics: failure and mental health. Failure, they noted, is an inevitable part of the entrepreneurial journey and a key notch on the eventual belt of success. In fact, most successful founders experience it multiple times. On average, entrepreneurs start 5.5 companies before truly hitting their stride. As Freeman put it, “How do you know an entrepreneur? They’ve failed. Now they’re educated.” Rather than seeing failure as a setback, it’s a driver that sharpens an entrepreneur’s resilience and business acumen. 

However, the stress that comes with building and sustaining a business can’t be overlooked. With 72% of entrepreneurs reporting mental health challenges, Franks emphasized the importance of self-care and nurturing the person behind the business, not just the business itself (“focus on the jockey, not just the horse”), and Mick reinforced the importance of vulnerability and transparency.

Evolving as a Leader Panel 

In Partnership with Denver Economic Development and Opportunity, BEN Advisors and Denver ScaleUp Network (DenSUN) Entrepreneurs came together for a lively panel discussion on Evolving as a Leader. Moderated by Scott Walker, the panel featured insights from Kristin Taylor, Lisa Pedersen, and Cedric Lipsey, who shared how leadership must adapt as a business grows, and how founders must individually evolve to meet new challenges. A key point raised was the importance of alignment within the organization, ensuring that everyone understands the ‘why’ behind their work. This shared sense of purpose fosters cohesion, drives performance, enables teams to navigate obstacles more effectively. 

In addition, the speakers highlighted the importance of self-awareness as a leader. Recognizing both your own personal strengths, as well as those of your team members, allows for greater collaboration and innovation. By understanding and leveraging each individual’s strengths, leaders can create an environment where everyone is contributing at their highest potential. Another key takeaway was the need for presence, as good leadership requires you to be fully engaged with your team and responsive to their needs in the current moment. Think ahead but focus on now.

The panelists also emphasized the significance of bringing personal values into leadership, especially when it comes to the way you treat your team. Embracing a people-first mindset will create a positive culture that ripples across the organization, resulting in both improved morale and productivity.

Finally, an important reminder was shared: “What if it all works out?” This paradigm shift from “what if we fail” question encourages leaders to embrace optimism and shift their perspective when the inevitable doubts set in. 

Embracing Vulnerability and Transparency

Led by Greg “Woody” Greenwood, this panel featured insights from BEN Advisors and Entrepreneurs Kendra Prospero, Joel Morrow, Chapelle Ryon, and Adam Oliver on the importance of transparency in leadership. One of the standout insights was the role vulnerability plays in fostering a supportive and trusting company culture. When leadership is open about their own experiences and honest when they might not know all the answers, they can create an environment where team members feel safe to do the same. This openness enables deeper connections and fuels strong teams. 

Another key theme that emerged was authentic leadership, which happens when leaders align their decisions with their personal values. Even through tough decisions, authentic leaders make decisions that are rooted in core values and a deeply motivating ethos. Leading authentically sets a powerful example for teams, encouraging colleagues to be real, focus on the shared purpose, and embrace vulnerability and transparency themselves. 

Finally, the panel stressed the importance of peer support for both personal and professional growth. Many leaders tend to feel isolated within their organizations, so seeking out a peer group of like minded individuals is an excellent way to embrace vulnerability, gain feedback, and encourage mutual learning in a safe space as you navigate the challenges of leadership together. BEN Colorado offers “BEN DEN” peer groups to allow for a safe, supportive space for entrepreneurs to share and collaborate on challenges.

Final Thoughts

Denver Startup Week once again provided a lively platform for exploring what it truly means to lead in today’s world. While the entrepreneurial leadership journey is full of challenges and obstacles, it’s also one of purpose, collaboration, reward,growth, and transformative possibilities.

A sincere thank you to all the incredible speakers and attendees who made these discussions both meaningful and inspirational. These conversations will undoubtedly make a difference as we all continue to grow as leaders. 

We look forward to seeing you next year!