In this monologue, Cameron Herold critiques the modern boom in business coaching, arguing that most entrepreneurs benefit more from mentors who have actually built companies than from generic coaches who rely on the Socratic method. He explains that coaching became popular in the early 1990s, but many coaches lack hands‑on experience and therefore cannot provide the shortcuts and practical insights entrepreneurs crave. Drawing on his own background training 800 franchisees annually for College Pro Painters, Herold illustrates how mentorship rooted in real‑world execution can accelerate growth. He also highlights the hidden emotional toll of entrepreneurship—silent stress, depression, and the reluctance to share failures publicly—creating a “compression bubble” that amplifies anxiety. Herold differentiates between various support roles: mentors (experience‑based advisors), consultants (hands‑on problem solvers), and specialized coaches (e.g., EOS, Scaling Up) who teach operational systems but often lack leadership soft‑skill expertise. He likens business coaching to the multi‑coach model used by professional athletes, suggesting entrepreneurs need a suite of targeted coaches (finance, leadership, communication) rather than a single generic coach. Throughout, he stresses that true entrepreneurial DNA is rare, noting a 3% overlap with bipolar/ADHD traits, and warns against the trendy, superficial portrayal of entrepreneurship on social media.
Chapters
Coaching is supposed to be the Socratic method where you ask somebody a lot of questions to get them to help figure out what they should already know intuitively inside. That drives entrepreneurs crazy. The problem with coaches is they tend to talk to you about every area of the business that they've never done it before. So they might be good at asking the Socratic questions, but they're not good at giving you the shortcuts and the tips that most entrepreneurs are looking for. There's only 3% of the population are bipolar. Only 3% of the population are traditionally ADHD. And it correlates very closely with the 3% that are actually entrepreneurs. Entrepreneurship in my mind has become too trendy and too fashionable and too like cool, and people are trying to be an entrepreneur. Maybe they should be entrepreneurial, but the people that actually have the DNA and then the skill sets to match, to really be an entrepreneur, to really be a company, is much less than has become trendy. The other thing is no entrepreneur that I've ever met will tell the truth about how hard it is while it's happening. We'll talk about it a year or two later, but we can't talk about the real dirty, hard, crappy stuff because it can hurt our brand, it can hurt our team, it can hurt our company's confidence. So we tend to live in that little silent shelter, or we have— maybe we only tell a couple of our friends, or we tell our coach, or maybe a mastermind that we're in. But no one talks about the theft or the embezzlement or having to fire a friend or not being able to meet payroll or the worry that we have at night. So we live in this kind of silent compression bubble, which amplifies the stress and the depression we go through. But we do tend to share the, oh, here's the beautiful life I've got, and here I am flying private, and here I am on all my vacations. So we share the good stuff, and everybody on social media only sees the good stuff. It's kind of like nobody shows how hard our normal day is at home either. Coaching has become a trendy thing. So coaching only really started in business in 1993. The International Federation of Coaching and Coach U both started in 1993. I'd already coached 120 entrepreneurs by 1993 because I got— I was involved in a franchise group called College Pro Painters, which became the largest residential house painting company on the planet. We had 800 franchisees that we had to sign and train every year. So imagine finding 800 new franchisees every year. So that was the group that I grew up in. What happens is coaching is supposed to be the Socratic method where you ask somebody a lot of questions to get them to help figure out what they should already know intuitively inside. That drives entrepreneurs crazy. What they really want is more of a mentor. That's probably what I play. I built the companies before. I've built businesses in the home services space. I can talk to you about what you're doing. I stay away from the areas I'm they're not good at. The problem with coaches is they tend to try to talk to you about every area of the business, but they've never done it before. So they might be good at asking the Socratic questions, but they're not good at giving you the shortcuts and the tips that most entrepreneurs are looking for. And they don't have the actual skill set to really analyze the business in a very good way. And then in the middle of that spectrum is the consultants, the person that you're hiring to come in and actually do the work to help fast forward you. So I think a lot of people that say they're coaches are probably more mentors. That's where I think the real benefit for most business people comes from, is finding a mentor. And then the next part of that is you've got the business process people like the EOS coaches or the Scaling Up coaches or the Next Level Growth coaches. They're actually teaching you systems to help you scale up the operational side of your business, but they probably don't have the leadership skills around things like situational leadership, coaching, managing people, handling conflict, like the soft skills of leadership. That's something like that I would bring to the table. So it's a weird, it's a weird thing that most people are looking for. Let's say that you're a professional athlete. You don't say, I need a coach. Right? You need a skills coach, a mindset coach, a fitness coach, a, a nutrition coach. You might have 5 or 6 different types of coaches coaching on different aspects of your business. So you don't need a coach for the garage industry, but maybe you need a finance coach, maybe you need a leadership coach, maybe you need someone to work with you on communications. So there's different types of business coaches as well.
