From Collapse to Comeback: How to Learn from Defeat on the Road to Success w/ Ben Brownback of B2Group

Summary

Ben Brownback didn’t set out to be an entrepreneur. His first brush with business ownership started when he was still a teenager, making videos for McDonald’s regional leadership. After spending years growing a fast-moving production company, he experienced the devastation of watching it all collapse—losing not only his business but nearly everything he had built. That rock-bottom moment didn’t define him. Instead, it became the foundation for his next act: building the B2 Group, a creative-focused event production company rooted in trust, strong culture, and a people-first philosophy.

In this episode, Ben pulls back the curtain on his entrepreneurial journey with raw honesty. He talks about learning business fundamentals on the fly, the emotional toll of letting employees go, the staggering financial risks he took to save his new company, and the leadership principles he now refuses to compromise on. His story offers a powerful blueprint for resilience, self-awareness, and leading with both heart and discipline.

If you’re wrestling with the fear of starting over, carrying the weight of leadership, or just wondering if true culture-first businesses really exist—this is a conversation you can’t miss.

Takeaways

1. Ben’s entrepreneurial journey started unexpectedly – when McDonald’s executives recruited him to help run an internal communications team as a teenager.
2. His first company, DAV Productions, grew too fast – doubling year over year—but eventually collapsed, teaching him hard lessons about financial vigilance and internal trust.
3. After losing everything, including financial stability, Ben faced a dark six-month rebuilding period – before launching the B2 Group.
4. B2 Group is intentionally asset-light – focusing on storytelling and creativity instead of heavy equipment ownership to avoid previous pitfalls.
5. The two most important early hires Ben made – were someone to manage money and someone to run operations—a formula he recommends to all founders.
6. Ben believes leadership is rooted in deep personal relationships – balancing professionalism with genuine care for employees and their families.
7. He stresses the importance of verifying trust – even among close teams, drawing from painful past betrayals.
8. Taking massive personal financial risks – like selling his cars to fund payroll, was necessary to keep B2 afloat in early days.
9. Culture starts with leadership – Ben credits his right-hand executive, Hannah, with maintaining a healthy, people-first culture as the company grows.
10. Today, Ben runs his business based on clear, unshakeable personal morals – he refuses to compromise them even when business pressures tempt otherwise.

Chapters

• [00:01] From Ben TV to McDonald’s communications
  • Ben’s entrepreneurial seeds are planted when a high school TV show leads to an unexpected corporate career.
• [03:05] Learning business inside a giant company
  • How McDonald’s unconventional mentorship helped Ben understand operations, budgeting, and innovation.
• [04:35] Launching DAV Productions
  • Ben and his mentor Dave start a production company focused on AV services with an innovative media edge.
• [07:11] Growing fast—and growing unstable
  • DAV grows 50–100% per year but faces challenges with asset-heavy operations and unchecked internal risks.
• [13:14] Losing it all and hitting rock bottom
  • Ben details the painful collapse of DAV and the emotional and financial aftermath.
• [16:02] Deciding to start again
  • After months of darkness, Ben chooses resilience over defeat and begins planning a second act.
• [18:30] Building B2 Group with intentionality
  • No more fixed assets—B2 focuses on creativity, storytelling, and serving niche clients who value differentiation.
• [21:52] When to bring employees onboard
  • Ben reflects on the emotional and practical weight of hiring again after a major failure.
• [23:16] Finding your right-hand people
  • He explains why his first two hires were crucial: one for finance, one for operations and leadership.
• [31:23] Betting everything—again
  • Facing another crisis, Ben sells his personal cars to fund the business and keep it alive.
• [36:01] Entrepreneurs often only hear the success stories
  • Ben shares the real mental and financial struggles that don’t always make it into the startup narrative.
• [41:43] Shaping a resilient company culture
  • How he built B2’s culture differently than DAV’s, learning to maintain professional distance without losing heart.
• [47:43] Leading with unwavering morals
  • Ben outlines his “true North” leadership philosophy: clear personal morals and trust but verify.
• [51:02] What young entrepreneurs should ask
  • Why success isn’t the right question—instead, ask about the worst failures and how they were handled.
• [55:18] What he would do if starting from scratch
  • Focus immediately on finance, operations, legal support, and staying laser-focused on the core business.
• [57:27] Book and leadership recommendations
  • He highlights Good to Great and The Contrarian’s Guide to Leadership as essential reads, and the importance of simply being a good human being.