In this episode of the Operate Podcast, we explored leadership through volatility with Dan Holt, co-founder and CEO of BillGO. Rather than looking back at his entire career, we focused on the major transformation he's currently navigating both personally and professionally as his company pivots its business model.

Dan shared candidly about reducing his team from 340 to 150 employees while discovering that a somewhat neglected part of their business was actually growing and thriving with 90% profit margins. He discussed how his leadership approach had to evolve, realizing that the fighter mentality and feeling of invincibility that previously served him well had become limitations to where he needed to go.

Our conversation explored Dan's perspective that "the hardest battles aren't outside, they're inside," and his development of practices to maintain calm during crisis – including intentional morning routines, daily exercise, and slowing down to ask better questions. He emphasized how a leader's presence can either diminish or create space for trust and innovation.

We also discussed Dan's evolving view on "wartime" versus "peacetime" leadership, suggesting that effective leaders need both capacities simultaneously. Throughout the episode, Dan offered valuable insights on maintaining transparency during difficult transitions and how treating people with compassion through challenges builds lasting resilience and trust.

Thanks to show sponsor, BankTech Ventures.

Chapter Markers:

00:40 Intro 

00:58 Sponsor 

01:30 Introduction and Background 

03:20 Current Leadership Transformation 

06:45 Leading Through Volatility 

13:32 Self-Leadership and Growth 

17:14 Daily Practices for Leadership 

19:52 Building Company Culture 

24:10 Building Trust Through Change 

28:50 The Pivot Decision 

35:10  Wartime vs. Peacetime Leadership 

42:59 Moving Forward: BillGO's Future 

44:39 Outro