In this interview, Richard Hagberg discusses the psychological and operational stresses that entrepreneurs face as their companies grow. He describes the typical entrepreneurial personality as visionary, adaptable, and attuned to market needs, but also distractible and averse to structure, which can impair decision quality. As startups scale, founders encounter heightened financial pressure and a lack of prior management experience, often having never worked for another organization or managed teams. This inexperience leads to decision bottlenecks, especially for founders with strong control needs, creating distress and potential burnout. Hagberg highlights warning signs such as an inability to delegate, excessive control, and feeling overwhelmed by decision volume. He notes the scarcity of open dialogue about post‑failure experiences and points to resources that can mitigate stress: professional coaches (his own role), peer support groups like Vistage, and personal grounding practices such as meditation. Finally, he offers advice for prospective entrepreneurs, emphasizing the need for a clear vision, tolerance for ambiguity, adaptability, and low anxiety in uncertain environments.
Chapters
They're creative visionaries and they're change agents and they're pretty adaptable. One of the things I think that leads them to become an entrepreneur is they're often very aware of external needs in marketplace and technology and therefore they see opportunities and they're willing to take risks for sure. On the other hand, they're often very distractible kinds of people. They're not all that structured and that gets in the way of the quality of the decisions that they make. Often they're people who don't like structure. That's why they've started to be entrepreneurs. And that has implications as the company grows. They tend to be workaholics. They appear on the surface to handle stress well, but internally that's far from the case as they also appear to be confident. But in fact, there's usually an insecurity that drives them and so stress begins to get to them.
What sort of pressures change versus with someone who's at the beginning stages of just starting a business versus when they are established and now have perhaps employees who are depending on them?
That's a very good point, I think. I think a big thing is that as the company grows, there's a lot of financial pressure and pressure that just comes from growth. And many, many of the people I work with have very limited business and management experience. In fact, it's not unusual for them to, to have never worked for anyone else or never managed anything. That's a difference between entrepreneurs that I work with today and ones that I worked with in the 1980s and the 1990s. The entrepreneurs in those days had much more management experience to draw upon. They had people who were role models for them. They had had management training. Today you don't see that. And as the company grows, not only are they have no experience to draw upon, no pattern recognition, but they also have teams of inexperienced and actually decisions get kicked up to them that they don't really have the domain expertise to deal with. And so that adds to the stress.
Talk about some of the red flags. What are some of the warning signs that founders or perhaps the people around them should be aware of to indicate that there might be a problem if
they have strong needs for control? Often there's a line of people outside their door waiting to see them, and they become a bottleneck to decision making and they often feel distress. I can remember one CEO saying to me, I feel like my head's going to explode. And what that was about was he was feeling that all the decisions were all coming to him. Decisions that he wished other people could make. He didn't recognize that he was a bit controlling, but more than that, he just didn't have the team to delegate to.
This does seem to be an ongoing problem. So why do you think there's not more open discussion about what happens? There's a lot made of these, you know, big startups that make these big IPOs, and even when there are failures, but not really that much discussion about what happens after the failure. What sort of resources are available?
First of all, one of the things I've noticed, and I think there's research to support this, is that often entrepreneurs are on their third or fourth startup before they really hit it big. Now, we can point to some exceptions of that. People like Mark Zuckerberg for instance, but. But I think they learn from the mistakes. And there are coaches, that's what I do. And there are CEO groups that are like support groups. Vistage is a company that puts together groups of entrepreneurial CEOs, small company CEOs, who get together and are a support group. Increasingly, these people are also seeking out things like meditation. I've meditated for many, many years, but until recently I didn't find a lot of receptiveness to that in terms of recommending it. Now in the last maybe year and a half to two years, I've referred 10 people to learn to meditate, and they've all done it and they are being consistent and following up. That makes a big difference because, I mean, in the end, if you're not personally grounded, you're going to have problems with leadership.
What sort of advice would you give for people who are deciding whether or not entrepreneurship is a good fit for them?
First of all, obviously you need to have some sort of vision and idea. You have to be able to tolerate ambiguity. For sure, Ambiguity is the name of the game in startups. You need to be just comfortable with change and you need to be adaptable. If your anxiety level goes too high when there's a lot of uncertainty, it's probably not for you.
