Risk, Parenting and Co-founding with Your Significant Other:

An Interview with Lisa Weiss

“Had you told me in 2002, when we were starting this business, how much of our own money and how long it would take to get in and out of this business, if I knew that upfront I would never, never have done it in a million years,” declared Lisa Weiss, who co-founded Dynamic Clinical Systems in 2003 with her husband Chris. It didn’t matter that they were able to sell the company in 2014, pay off all debts, put their two girls through college, and end up with about the same nest egg had they kept their consulting careers. It didn’t matter that they did all that while getting to be their own masters rather than working as suits. “Given knowing how it came out, I still would not have done it,” Weiss reiterated.

When we spoke with Weiss, we were hoping for some perspective on being an entrepreneur while raising a young family; more specifically, co-founding a company with her husband with a 7-year old and a 5-year old in tow. We got it! She was forthright about their journey, the challenges, co-founding with your significant other, her and her husband’s different perspectives, and how it impacted the kids. Interestingly enough, it was because of the kids that they took the entrepreneurial plunge in the first place.

“The whole impetus for this was around the fact that we did have young children,” Weiss explained. “We were both consultants, both flying every single week, out Sunday night, back Thursday night. And our kids at that time were in second grade and kindergarten and being raised by nannies and such, so we were really feeling like we needed to do something different.”

Point of Conflict and Life Coaching
Both Lisa and Chris were entrenched in management consulting firms, so before making a big change they tapped some professional help. “We did go see a life coach for a weekend and they do what’s called a Vision Day,” Weiss explained. “They talk to us separately and then together to try to get us to reconcile our different perspectives on what we want to do. Our big point of conflict at that point was in respect to risk aversion and where we are on that spectrum. I hate to do gender stereotypes but it’s certainly something where you read that men tend to be more comfortable with risk and women tend to be more risk-averse, and I fit that stereotype for sure. He was much more comfortable with let’s just quit our jobs and have no income and figure it out; and I really wanted one of us to keep our job. So life coaching helped us get comfortable with quitting our jobs and figuring it out.”

They sold their house in Massachusetts and moved to bucolic Hanover, New Hampshire – a place they knew pretty well because it’s home to Dartmouth. (He went to undergrad there and she got her MBA at Tuck.) It also had the small-town values they were looking for. “We started dating companies,” Weiss said. The plan was one of them would hook up with a startup that could benefit from some consulting expertise and business acumen, while the other would take a secure job with a guaranteed paycheck. However, with neither of them able to find a particularly exciting job, they both decided to go the start-up route but with different companies – again to mitigate some risk. The Dartmouth affiliated teaching hospital (DHMC) offered some opportunities in healthcare as doctors and professors spun out companies.

The Best Laid Plans … Often Go Awry
Ultimately, Weiss started formulating a business plan built on collecting and analyzing patient healthcare information with the end goal to improve patient care. “It would be a really nice way to contribute something good to the healthcare space, as well as trying to make some money off of it,” she explained. “We did some market research; we worked with a Tuck team on a feasibility study. They gave it a thumbs down, so I was ready to abandon the venture but Chris really liked it.” Again, her husband was more willing to take on the risk. They co-founded Dynamic Clinical Systems in January 2003. She served as executive vice president of product strategy, he as president.

Still planning to take an alternate route from her husband, Weiss committed to stay for six months. The six months turned into a year, which turned into two years, which then turned into six years. The same for the money commitment. First it was a modest amount of their own money. That doubled. And again. They mortgaged the house and borrowed money. And again Weiss reiterated, “I would never have chosen to go into it if I had known that upfront.” But for her husband, it was game on. “You get a very different perspective from Chris,” she noted. “He loved it. He loved the game. He loved working on his own. He loved the building of something from nothing. And I loved aspects of it. I loved our clients. Loved the type of work it was. Loved the product development. But for me, I would’ve loved it so much more if it had been venture backed or part of a larger organization. I just could not stand the risk.”

The Frog Analogy
This brought the conversation back to whether women truly are more risk-averse than men. “Yeah, I’ve definitely read a lot about how the kind of risk aversion that women tend to have is greater than men. I don’t know all the science behind that, why that is, but certainly it’s not that surprising in some ways. You see that in all kinds of businesses, not just entrepreneurship but in businesses where there are high-stakes, high upside, high-risk, they tend to be more male dominated. I definitely fit that stereotype of preferring something more secure, and Chris was just way more comfortable thinking that it will work out.”

To further make her point, Weiss depicted an exceedingly apropos comparison: “So one analogy that I think is perfect for our situation is the frog jumping into the boiling pot. It is a real scientific fact that if a frog jumps into cold water and then you turn up the heat over time, they will stay in that water until it gets hot and starts boiling and will die. If they jump into boiling water, the frog will jump right back out. That analogy for me is perfect for our situation.” She found herself to be the frog in the slowly warming water.

With the original plan of taking separate paths, and then the six-month commitment turning into six years, we had to ask how it was co-founding and running a business with her significant other. “I continue to be of the perspective that it is not healthy for a marriage or relationship,” answered Weiss. “Maybe it’s hard to generalize that way because I’m sure some of it depends upon individuals, compatibility levels, things like that. I think it’s just too much of one person no matter who that person is. Even if it were your best friend, to spend 24/7 with the same person I think is hard no matter what. But that might not be true for everyone.

A Complicated Threesome: Husband, Wife, and Work
“I think you have to be the kind of person who is really good at being able to compartmentalize, to separate work from personal. For us, we worked out of the house; we had our desks set up in our bedroom. We could find ourselves getting in an argument about work, and having a harder time transitioning back to personal and vice versa. I think it can just be challenging to go in and out of those two different worlds.” It simply made it that much more difficult to leave home things at home and work things at work. There was lack of boundary.

“I would say in addition to your own relationship, it can be hard for your team. We actually have people who said that,” added Weiss. (Eventually, they took office space and built the company into a team of 15 people.) If they weren’t happy with one of us, they didn’t feel like they could complain to the other one of us. I think it can make it hard for other people because they can’t treat you like they would their other colleagues.”

Now with some distance from the experience and having some perspective, we asked Weiss about key stressors that stood out (in addition to the risk). “Certainly borrowing money from family, I think it’s a very complicated thing to do even if it’s no strings attached and involves a very willing family member. And then going into personal debt ourselves with the real possibility of having to pay off debt, debt with nothing to show for it. That for me is a risk tolerance I don’t have. But I also think working 24/7, we just never had a day off, and went so long without vacations, and we were trying to raise small kids. It actually would be interesting to interview the child of an entrepreneur. I’m not sure what they would say. I think it was hard for them that we were working a lot and working out of the house.”

Fluid Family Dynamics
This latter comment naturally prompted a little further digging into the family dynamics and raising kids while building a business. “I would say there are some positive lessons that our girls learned from us doing this business together,” answered Weiss, “and that they had to live a much more modest lifestyle for quite a few years. They didn’t get new clothes and things like that. What they picked up on here and there about being entrepreneurs, that was all good.

“I’m not sure I would want to start from scratch on my own as a young parent. I would probably enter at the point where someone else has either gotten some venture capital or is looking for someone to lead the company. I might do that. I think as a young parent, if your partner has a secure job and can offset risk, that’s a whole different stressor that can be mitigated. I mean it’s still painful because you’re making half the income but if you can have someone who’s covering the bills … I think my advice would be not to put all of your eggs in one basket, especially if that basket is an unfunded startup.”

We still wanted to know how Weiss got quality time with her kids. “They would tell you we weren’t great at that,” Weiss said forthrightly, “and I would say we weren’t great at that. I think they had to become independent a lot earlier than they might have otherwise. Like I made them start making their own lunches in the second grade, which they half-teased me about and half-resented. We’ve got some funny stories about balls that were dropped in taking care of them that wouldn’t have happened otherwise if we did have stable jobs. We did a lot of parallel playing. If they wanted to play a game, I would stop working, play a game, and go back to work. We did not go off the clock at 5 p.m.”

However, they did set aside Friday nights. “Friday nights were our movie nights. We didn’t have TV for the kids growing up, we didn’t have cable, and back then you didn’t have Netflix and such, so we never had a TV going in my house, but we would rent videos on Friday nights. We still spent a lot of time with them, it just wasn’t structured time. We played a lot of games with them.”

We asked Weiss if she ever had moments of regrets as a mom. “I definitely did have those moments,” she acknowledged. “I have vivid memories of going to their school concerts, and when my kids weren’t playing, I would go out into the hallway and work on some deadline that I was crazily trying to meet. So there were things like that when I was trying to meet some deadline or take some client call in between something I was doing with them. So yeah, that doesn’t feel great. I think in some ways my kids were more accepting and even used to it. Even though they kind of joked about it, they might’ve been resentful.

“They were so used to it, but sometimes I would worry what other parents would think. I definitely had a lot of amazing moms in my life who were really good at making the chocolate chip cookies for the kids when they came home, and making their lunches, so sometimes I felt a little inadequate as a mother compared to other moms who were spending more time doing stuff like that. So yeah, absolutely there is that kind of guilt and feeling those inadequacies as a mother. But I also feel like even if I had a consulting job, I probably would’ve had the same kinds of things going on because it’s just in my nature to focus on work like that.

Justifying the Trade Off
“I think the biggest thing for me, the hardest part I would continue to go back to, is less about how much work it was, the hours, even though that was a big piece of it, it was more about the fear of financial collapse and what that might do to our family. I think that from a family perspective and a mother’s perspective, my concerns were less about the job I was doing as a mother and more about as a provider, a financial provider, and making the right decisions as someone taking care of my family financially.”

Being a mother did make her more aggressive in terms of building the business and driving revenue to essentially protect the family unit. “I would definitely say that was the driver behind the trade off, the hours I worked versus spending quality time with the kids.” she expounded. “I would justify that trade-off with the feeling that I’m doing this for them as well. I have to work this hard because I want to land this client or I want to land this deal; and I want to make this money because this is what I need to do for our family. So I would say that was behind the kind of self-rationalization of how hard I was working.”

By the way, the Weiss’s two daughters are doing great – we know firsthand. Lisa Weiss remains dedicated to improving healthcare, most recently as CEO of High Value Healthcare Collaborative, a consortium of healthcare delivery systems, including Dartmouth Hitchcock and the Mayo Clinic. Nevertheless, mom sticks to her guns when she says she wouldn’t have cofounded Dynamic Clinical Systems had she known what she was getting into. “I think what I would’ve done differently is what we originally planned, which would be for one of us to take a secure job with benefits and such, while the other one went after riskier type of work. I think that would’ve been a better setup. I’m not saying this out of a point of resentment. We made all these decisions together. And I absolutely would have had Chris do this because he loved it. The entire time that he was doing this, he had a lot of job satisfaction, the kind of satisfaction he could not get from the corporate world. He enjoys working for himself way more than for other people.”