“I resonated a lot with the
flexibility of being able to
go off to tackle something
with a lot of self-direction.”
Ben Williams, serial entrepreneur and CEO of Zentropy Consulting
Ben Williams is a serial entrepreneur, who has had his hand in everything from the early days of the internet to influencer marketing to solar energy—between stints in the U.S. Navy and Lockheed Martin. He now draws on those experiences to coach early and growth-stage startups to success with Zentropy Consulting. Here he talks about the value of an outside perspective to a founder, how to turn fear of failure into a wealth of learning opportunities, and a very unusual living situation in New York City.
What excited you about entrepreneurship on a personal level?
I started out just because I needed the money when I was in college, and so it was a very obvious thing to do because it was the only thing that was right in front of me. I could still go to school. I could still be on the track team. I could still hang out with friends. The flexibility was the only thing that would fit. In that context, necessity is the mother of invention.
Later on, I resonated a lot with the flexibility of being able to go off to tackle something with a lot of self-direction. Even within the Navy, that was a thing we had a lot of. My first tour, part of my job was running boarding teams in the Gulf for the second Gulf War. They would often give us very broad directives and go, “Okay, we’ll pick you up in a month. Go get some of that stuff done.” [Laughs]
As a 22-year-old, you’re both cocky enough to think you can do it, but also flexible enough to roll with the punches and figure it out. That was super interesting, and taught me a lot about how to be flexible, but focus on using existing resources. And that is a very, very similar philosophy to entrepreneurship, where there’s a lot of documentation on what you could do, but you have to adapt that to your specific scenario and environment.
Did you have any fears about becoming an entrepreneur?
I wouldn’t say it was fear at the beginning. There was plenty of fear while doing it. It became much more specific. I would say that in the grand scheme of things, I have a lot of confidence that things will work out okay, probably because the way that I frame it—even internally—is that there are very few permanent failures outside of death. Everything is an opportunity to learn a little bit more and to not make that same mistake the next time. Edison had that quote; he’s like, “I haven’t failed to make a light bulb. I’ve found 500 methods that didn’t work.” I think that’s a very cogent way of putting that together.
How did you cope with any kind of fear or hesitation?
Sometimes you depend on friends and family. For a certain period, I would do a lot of long runs to help me relax, or sometimes I would take a video game break or read or whatever. In a less healthy way, maybe drink beer or wine—probably not quite as good, but necessary sometimes.
I think a lot of times it’s maintaining perspective and having a framework for thinking through things. Like, instead of allowing them to become really overwhelming, taking what might seem like an overwhelming task and start breaking it down into smaller things. And then, by the time you’re done with that, it doesn’t seem so overwhelming and you can just get back to business.
What has been the greatest struggle in your entrepreneurial journey?
It’s hard to pick just one. Maybe halfway through my time at [influencer marketing company] Reelio, [where I was a co-founder and the COO], we brought in some HR help to better our management, to give trainings, and to provide a relief valve for people who we weren’t necessarily sure were going to talk to us as founders. We wanted to have other ways to get some feedback.
I believe that no one is anywhere near perfect, but it’s still always hard to hear negative feedback. The first time we did a really in-depth survey, I heard that a lot of people thought that I wasn’t listening to them or that I wasn’t responding enough to feedback or wasn’t taking it in—it was a bunch of different versions of sort of similar feedback. That certainly hit me hard, because I wanted to do better with that. So trying to think of ways to tackle that without coming across as, “Hey, all you guys said I sucked at this. What the hell?” Especially since the whole point is trying to listen. [Laughs]
It was an exercise in swallowing pride, but also trying to figure out how to listen actively so that they understood I was listening. It was this weird trying to balance. I hope I got better. I don’t know for a fact, but I got some good feedback afterwards that at least I appeared to be trying.
What has been your greatest triumph in your founder’s journey so far?
Probably selling the last company was pretty good. That’s not a bad one. Beyond that, I think the piece that probably is most validating is not necessarily those pieces, but where you get validation from people who you respect and trust. As I’ve been networking over the last few months, doing some coaching and consulting and mentoring work, I’ve met with a bunch of interesting venture capital reps and that sort of thing. They’re in a position where they don’t have to be nice to be. I’m not asking for anything from them, but a few of them—without any kind of prompting—have said that they were impressed by either pieces of my background or things that I’ve done. That felt pretty awesome.
“You have to be the end decision-maker, but you
don’t have to make the
Ben Williams, serial entrepreneur and CEO of Zentropy Consulting
What has been your biggest sacrifice?
During the early days of Reelio, I was leaving a job with good salary. I would have—I assume—continued to do okay there. It felt like I was actively giving up a lot of money for the opportunity of what statistically would likely be a failure. Financially, it felt like a somewhat irresponsible thing to do even though the hubris of the founder is, “I’m different though. I’ll get it done.”
Where it really started to feel crazy was when we moved the company to New York and we ran it in Manhattan for a while because all of our customers were within a 30-block radius of the Flatiron [building], so it made a lot of sense. But I couldn’t afford to live anywhere there, so I rented one room in a four-bedroom, one bath, illegal loft in South Williamsburg. You paid cash. Over two-and-a-half years, I had like 35 roommates. There were always people skateboarding or playing saxophone or weird stuff that. Probably when I was in my early 20s, I would have been like, “Cool.” But on a Tuesday night at four in the morning as a 35-year-old, I was like, “Let me go the fuck to sleep. I’ve got work in the morning.” [Laughs]
Have anyone in your personal life been a constant source of support throughout your entrepreneurial ventures?
The ecosystem for startups in general is a really positive support structure. Partially because people are going through it, but also because they know that if you put in the energy and the time and you’re open to feedback, you can greatly improve your chances for success. So if you’re willing to listen and take feedback, they will happily give you some. There’s a self-reinforcing success factor that is present in the startup ecosystem that I think is very helpful.
Tell me about your work-life balance.
In the early days of a startup, there’s not a lot of balance. I think that’s true of most founders. When I started, I was single and didn’t have kids, so it was easy to go way all-in. I met my wife halfway through Reelio, and so work-life balance began to enter the equation over time. Especially now that we have a son, it changes yet again. You begin to focus in different ways.
I don’t think that spending that amount of time makes you that much more effective. I think when you have other priorities on your time and you’re good about balancing them, you end up being more effective with the time you do spend. I think that there’s no getting around that, as an early stage founder, your work-life balance goes away quite a bit. But I think that once you start hiring and bringing on good managers, and if you’re doing your job right, you should hire yourself out of a job over time. There’s other things you’ll have to continue to do, but you’ll take on new challenges, and you should, over time, be able to optimize a little bit for however you want your life balance to be.
Did you ever come close to giving up?
That would happen twice a week. You’d have pretty wild swings. In the morning you’d get up and be like, “Alright, let’s hit this.” By mid-morning, you’re already like, “This is all going to fail. I might as well pack it in.” And then something else happens and you’re on top of the world again. Just like a wild ride in that sense—not always in a positive way. For me, it was also a balance of: Even if it fails in that we have to declare bankruptcy or we shut it down or whatever, I still will have learned so much that either I will have a much higher success rate in my next venture or I’ll be able to roll this into experience in a larger company.
What would make you feel as though you accomplished what you set out to do when you first became an entrepreneur?
There’s probably a couple different ways to think about it. I don’t do all of this for the financial outcome, but it would be interesting to be in a position not to have to work again. I think that would be a by-product of doing a few other things well, but also a large element of luck and chance and whatever.
Beyond that, I think that being able to show a repeatable approach that works, like a way of thinking about market entry or product development or company building or something like that. At this stage, I can show some repeatability. But for founders a lot of times there’s this inferiority complex. You’re always like, “Maybe it was just luck. I should probably do it one more time to really prove that I know what I’m doing because I probably don’t.” It would be nice to say that there’s a specific time at which I can go, “I have succeeded. Now I can relax.” I don’t really think that’s going to happen, but dare to dream.
What’s the most important lesson you’ve learned as an entrepreneur?
I think humility is a really, really critical piece because, even if you’re not super ego-driven innately, the position of being a founder requires you to put on that mask sometimes. Especially for investors, who expect you to be like, “Take no prisoners. Succeed at all costs.” And that can be toxic for some people especially, but also it can be a weird culture if you promote that in your company.
There’s a lot of weird pushes and pulls on a founder, especially around how you act and how you position yourself and how you talk about the company and your vision and employees and the culture, and it’s sometimes not super consistent. It takes a long time to both recognize how you want to manage it, how you communicate it, and how you adjudicate these different requirements from external sources.
One thing that I think a lot of people don’t do soon enough is bring on advisors and mentors or coaches. That may sound self-serving since I am a paid coach and mentor, but I attribute a lot of whatever success I’ve had to being able bounce ideas off of far more experienced people, either in a paid capacity or just grabbing a beer with another founder or listening to experience employees that you have, as well.
You can’t necessarily share everything with employees, but you can put them in a position to make intelligent decisions around a subset of your information. And to the extent that you can do that, you can leverage their intelligence and their capability—which is why you hired them in the first place. I think founders often take way too much on by themselves. You have to be the end decision-maker, but you don’t have to make the whole decision, you don’t have to come up with all of the pieces of the pie and put it all together and do the research. There are people that should be helping you with that.
This interview has been lightly edited from an in-person conversation for clarity. Capturing Lightning is a project from Woden, a strategic storytelling agency in Philadelphia that helps organizations articulate who they are and why people should care. To learn more about how to tell your story, visit us at wodenworks.com.