Homeless, Bootstrapping, and Living on the Outer Edge

A talk with Greg Kotzbauer, an entrepreneur in the healthcare industry

As we sat at a local coffee shop, he described how bootstrapping is a way of life, and I munched on a solid egg sandwich. Then he told me how he is effectively homeless, all of his personal belongings in storage, him living out of hotel rooms and crashing with friends or family. Like an entrepreneurial vagabond. I set aside the sandwich.

Mind you, Greg Kotzbauer is not truly homeless and certainly not going to bed hungry. As you read on, you’ll find that for him bootstrapping is truly a way of life, to keep him living on the edge, pushing boundaries, and feeling alive. The guy’s got a BA in Psychology from the University of Kentucky and a Masters of Science in Clinical and Health Services Research from Dartmouth College, so he’s pretty sharp, especially when it comes to the human condition.

Deeply involved in the healthcare industry – more specifically, the founder of a pair of companies (U.S. and U.K.) with a mission to help industry leaders implement change through behavioral modeling – Kotzbauer’s enthusiasm is infectious. He’s also blunt and uncompromising about his goal for his venture: “I only want to build a product that wows people.” He has a real passion for what he is doing, that is, to change the healthcare industry for the better, to offer real value. For him, it has to be emotionally meaningful.

At the same time, he acknowledged upfront, “It’s a lonely space. The ups and downs are very wearing.” And it should be no surprise that his hours can be “insane.” There are other challenges too. Since he’s bootstrapping, cost management is critical, and runway is always an issue (welcome to the club, right?), because his contracts with entities are typically for one year. “So there’s always that concern of what next?” he said. “Will I get another contract?”

Self-doubt As Barrier and Inspiration

Another challenge is that Kotzbauer doesn’t have a sales background – even putting together a one-page pitch can be a challenge – and he’s basically a one-man sales force! “Taking no for an answer is really hard,” he said. And later added, “I have the courage to put myself out there, but I also have fears. I know I need to build better communication skills. I need to know the market better. And I need to not worry about failure.”

From our conversation, it appears that self-doubt is actually his biggest barrier – not a good thing for an entrepreneur – yet Kotzbauer also seems to thrive on it because it makes him feel alive. “That self-doubt has kept me back quite a bit,” he admitted. There have been times when he hasn’t fully realized the value of his product. “Not having a partner for trusted guidance and feedback has slowed down growth.” He added, “Not having trusted advisors can cause you to crack emotionally and then cause the company to crack.” So he largely relies on happy clients to remind him of his product’s value.

Podcasts for Company

To survive emotionally or mentally tough times, Kotzbauer’s solution is pretty simple: “I get through down periods by working harder. I won’t let it stop me.” All the while he is working to increase his emotional intelligence and resilience to better his chances of success. “You need to build an emotional bank and knowledge of your space, then failure can be avoided,” he said. He also advised, “Listen to others’ lessons. Try not to prove something you’re not. A lot of the emotional ups and downs are because of unrealistic expectations. Focus on who you want to be. It helps you stay grounded.” One thing he does, especially since he’s a solo act, is to listen to podcasts. “I listen to podcasts about startups so I’m constantly hearing what emotions others are going through. When you hear their voice and their journey, you know what to expect.”

Resilience & Pushing Boundaries Through Athletics

And there are the marathons, ultra races, and iron man competitions. “There’s a natural resilience that comes through sports, that’s built into sports,” Kotzbauer explained. He first competed in an Iron Man back in 2000, and to get ready he trained with someone who measured everything. That someone kicked his butt in the race, which opened his eyes to how you have to push and measure yourself on so many levels. It’s easy enough to measure your times in race training, but in pursuing a business venture as a founder it’s not quite as straightforward. So Kotzbauer really looks to stay attuned to his passion and energy levels in his work life: “Is it emotionally meaningful? Measure your interest, your pace.”

Training became not just about measuring, but pushing his body and mind by purposefully causing pain; for example, Kotzbauer will allow lactic acid to linger in the muscles, and then push through the pain of a training session. Pushing through the pain and knowing you’re going to make it carries over into his business life – it makes him more resilient. And it’s about pushing your limits, pushing out boundaries. “We all have our boundaries, that area in which you feel comfortable,” Kotzbauer observed. But from competing in these grueling competitions, he wants to push beyond those boundaries. “I always want to go a step beyond the boundary, where life becomes extraordinary and meaningful.”

In business that can include pushing to think outside the box, to see what other people are not seeing, to explore the unconventional. Or it can be always improving and testing your product in real time, which can certainly create tension and a little stomach acid as opposed to lactic acid because you could be risking the loss of customers and revenue during such testing (search Lean Startup drawbacks).

Get As Many Wins As Possible

When you’re pushing boundaries, failure can happen. That’s a given. However, Kotzbauer’s not a big fan of viewing failure as a way to earn your stripes. “It’s OK to understand failure happens, but you need to get as many wins as possible. Even small wins. They sit with you. You want to replicate them. You’re seeking something positive that can get you into a rhythm.” That way when you do have a failure or a down period, you know you can get through it, you know how to succeed. “Several failures in a row can lead you to fearing another failure,” he explained. Paralysis can set in. “Failure sucks. So set yourself up for little successes. But do it in a balanced way. You don’t want to fool yourself.”

Kotzbauer strongly believes you need to reflect on everything you do, which will help build that bank of emotions and business savvy. Being an entrepreneur is a very spiritual experience for him. “I’m using this to find myself,” he explained. “I use running to find myself. I want to be living on the edge. A boundary is permeable. And your boundary is often farther out than you think!”