Escape the CEO Doom Loop
Escape the CEO Doom Loop is built for CEOs and leadership teams ready to grow. Each episode delivers practical insights, real-world stories, and tools you can use today to lead with clarity and scale with confidence. We spotlight what’s working—and what’s not—for leaders navigating growth, building culture, and driving accountability.
It’s more than a podcast—it’s a gateway to The CEO Playbook and the next step in becoming the leader your business needs next.
Escape the CEO Doom Loop
Episode 5: Discipline, Vision, Trust: The Core of Real CEO Growth with Bill Costello
In this episode, Glen and John sit down with Bill Costello, CEO of Streeter Custom Builder, for an honest and insightful look at what it really takes to transition from doing the work—to leading the people who do.
From running operations to stepping into the CEO seat, Bill’s journey is filled with the tough mindset shifts and real leadership lessons that define a high-performing company. Whether it’s letting go of control, navigating team turnover, or building a leadership rhythm that drives culture and profit—Bill shares how he escaped the Doom Loop and built something stronger.
This conversation is packed with truth, strategy, and the kind of wisdom only hard-earned experience can bring.
In this episode, Bill shares:
- What it was like to take over a legacy business—and why vision had to come first
- The hardest transition of all: letting go of operations
- Why accountability scared some people off—and why that’s okay
- His framework for coaching senior leaders instead of managing them
- The rhythm that built consistency, culture, and over $3M in net profit
- What changed when he stopped being the fixer and started asking better questions
- How “Automate the Ordinary, Elevate the Extraordinary” became a leadership mantra
- Why building an A-level team is the CEO’s most important job
Timestamps:
00:00 – Welcome + Meet Bill Costello
02:30 – From COO to CEO: The messy middle
06:45 – Trusting the team to rise
11:10 – Letting go of control and the COO title
15:30 – Building a vision the whole company could believe in
21:15 – When the vision finally clicked—and fear turned into buy-in
26:50 – What accountability really means (and what it cost them)
31:20 – Turning metrics into motivation
36:15 – Bonus structures, performance, and retention
42:30 – When team changes force a reset
47:00 – Coaching through hard decisions
51:45 – Working on the business vs. in the business
55:00 – Ask more questions. Be patient. Stay disciplined.
