Ken Herold’s fingerprints are all over the St. Louis startup scene. As an entrepreneur-in-residence for HOK, a global architecture, design and engineering firm during more than two decades with the company, he’s mentored more than 40 companies, has fractional C-suite roles with four area startups and is an adjunct professor of entrepreneurship and innovation in both the business and engineering programs at St. Louis University.

With a bachelor’s degree in architecture, a minor in computer science and a graduate degree in artificial intelligence from Washington University, Herold developed the first 2D/3D database for a computer-aided design and animation system for HOK. Over the ensuing decades, he became an independent technology consultant before returning to hold the office of Chief Knowledge Officer (CTO) until 2012.

Now, he serves as a shepherd to the next generation of entrepreneurs. His experience has made him an invaluable guide for founders looking to find success in the startup ecosystem, and EQ asked him what makes for successful mentorship.

You have so much going on—how do you manage it all so effectively?

It’s almost like being a bumblebee. As I’m driving and helping one company, I’m learning things, I’m finding out things and bringing new things to them, but I’m also thinking those for next time when it could be a whole different industry.

It’s really, how to take ideas and apply them through technology to do something new and different. That’s what I do.

Some companies have very strong leadership and technology, so I can mentor them. But then at some companies, I get involved on a deep level where I’m driving that for them.

What makes a good mentor?

A good mentor is like a good psychiatrist, [you need] to be honest. A good psychiatrist doesn’t fix you, right? You fix yourself. All the psychiatrist does is walk you through a thinking process so you get that “ah-ha!” and you do what you need to to fix yourself.

It’s the same thing with a startup. I can’t make a startup successful, they have to make it themselves. It’s more of a process of taking them through a journey so they get that enlightenment and understand what they need to do.

I think mentors who aren’t successful are the ones who have an idea of what they should be doing, and if they don’t do that then they are going to fail. I’d rather work with a startup to find a way that works for them to get their goals accomplished.

Not necessarily tell them how to do it, but they get to that “ah-ha!” where they understand what they should be doing. In the real world now, things change so fast, if you go down one track, you’re lost.

You have such a wide-range of experience, but your expertise is in technology. How important is it for startups to have diversity in the experience of their mentors?

My specialty is not marketing, not finance, not really being a CEO. That’s why I like doing these programs so much.

We as mentors each have our own specialty and even though I’m maybe working with one startup that’s very technically savvy, I may pull one of the other mentors out from the marketing side or the financial side. As a lead mentor, my job is to help them.

So it’s more like project management where I bring up other people to help them and giving them connections to people they didn’t know. That’s also the part of the lead mentor.

I’ve had ones where I’ve gone to either customers I know, clients I know, finding investment for them and that kind of stuff. Really trying to bring to bear whatever is going to make them successful.

It seems pretty simple in principle, but it can’t always go that smooth. What are some of the challenges you encounter as a mentor?

The frustrating part is when you get startups that don’t follow the advice. It’s a personality thing. IT gets sometimes more complicated if there are multiple founders. Now you have multiple personalities.

At the very beginning of the class, where I come in, the first day we take them through a lean startup process, like a lean canvas. That starts to help set in their mind what they’re trying to get accomplished with this business.

If there’s multiple founders, it gets a conversation going to make sure they’re all on the same page. That’s always a problem. If you have a team of people, you want to make sure they all believe the same things and are going in the same direction.

How do you break through when the personalities are less easy to coach?

I think a lot of it is how you treat them. If you treat them more like a psychiatrist, so you’re helping them think through it and not telling them what to do.

What happens if you do it well, is they come up with the ‘ah-ha’ themselves. It becomes their idea and they internalize it and then they do it. That’s the difference between being told what to do and being shown how to do it.

All this takes a lot of time, patience and energy; what makes it worth it?

What it takes for all the mentors is the desire. I do it because I love an idea. If you think about my architecture background, I love the creative process, I love an idea. To me, a startup—and especially technology—is a creative process.

That’s why I love doing it. I get to help other people deliver interesting things.

I do it myself as a fractional CTO or things, but also getting to help people is almost like a drug. The excitement of a new idea, the excitement of trying getting that new idea to work. That’s what drives me forward.

I also just like working on a lot of different things. I was a hyperactive child when I was young. I can’t be doing one thing at a time.