The Hard Decisions Behind Scale: Chris Hessler on People, Focus, and Advice

The people and decisions that get a business to one stage may not be the ones that take it to the next. In this ScaleCraft episode of The Joe Jaap Podcast, Joe Jaap talks with Chris Hessler, founder and CEO of The Advisory Bench, about what changes as a company grows and why even experienced CEOs need perspectives beyond their own.
Chris shares how his first advisory board helped him build a business around a U.S. Postal Service contract. Years later, that board challenged him to stop investing in a second product and focus on the core business, which grew to $120 million in revenue. Drawing on his experience building and selling companies and working in private equity, Chris explains why scaling demands difficult decisions about people, priorities, and leadership.
In this episode, you’ll hear:
Why the team that gets a company to $10 million may not get it to $50 million
What humility and coachability look like in a CEO.
How the right advisors can challenge a decision without taking it away from the leader
Why a promising new idea can distract from a proven core business.
How to work backward from the company you hope to sell in three to five years.
Where AI helps leaders, and where experience and judgment still matter.
Many of the problems a growing business faces have been solved before. The challenge is finding people who have lived through them and being willing to listen. Produced by EmoryDay. New episodes weekly.
https://www.youtube.com/emoryday
https://www.facebook.com/emorydayllc/
https://www.instagram.com/emorydayllc/
https://www.tiktok.com/@emoryday
https://x.com/emoryday/