EPISODE 6: Love and Business

Published 11/09/23

I would probably caution anyone against going into business with their life partner or their spouse if they hadn’t really clearly talked about it, and the goals and what each person’s role was going to be.

KAREN 00:13
If someone were to bring that to me — they were thinking about working with their spouse —  I’m not opposed to it, just like I’m not opposed to marriage.

Partnership. It’s a word that describes love relationships. It also describes the work relationships. And despite advice to keep our personal and professional lives separate, sometimes it’s just too tempting for romantic partners to launch work ventures.

“Love and Business.” That’s the topic of this episode of “Dating While Gray: The grown-up’s guide to love, sex, and relationships.” I’m Laura Stassi.

If you ever eat at a Panda Express, or drink a bottle of POM Wonderful, you’re a customer of a husband-and-wife owned business. Those two couples, they’re raking in billions.

Though the majority of couple-owned businesses are classified as small businesses. That usually means less than $10 million in revenue. And while some couples plan for the day they can launch their own thing, others kind of stumble into an opportunity.

That’s what happened with Allison and her husband. They were raising three young kids in Los Angeles when they decided to pull up stakes.

Once we did the math of how much it was going to cost to send them to good schools in California, we started to look around for other places to live. And we checked out the Midwest and the Pacific Northwest. We finally came here to the Research Triangle area of North Carolina, where I had some family, and we liked it a lot.

Allison’s family moved in 2005, and her husband started working at a university. That’s where he developed a health care education software platform. After six years, he went out on his own. Allison was happy to join him in the new venture.

I don’t know what I did for those first few years. I called myself the accidental CEO. He really did everything. I mean, I have such admiration for him. He was the programmer and the system administrator and the trainer and the documentarian and the salesperson. And I just kind of, you know, followed up behind and sort of swept the stage and made a few phone calls. And so to see where I’ve come from those days is really, it’s been transformative.

Did you have office space, or did you work out of your home? Tell me a little bit about how it worked.

It was absolutely the mom and pop, literally out of our home. When we realized that there was an opportunity to spin this out as a separate company we both said, sure, let’s do it. You know, it’s like Mickey and, Judy — I’ve got a barn, kids, let’s put on a show, you know. And what we didn’t know probably actually saved us and kept us going in in certain ways.

We walked out of Duke with three university clients under our belt using the software, which pretty much helps run medical schools. And so we just kind of kept going from there, Laura. We learned as we went. We’re both very big students of learning as you go along. And I think we got up to maybe 10 or 11 universities that we worked with, and he was really the only person working on the software.

And did the business aspects affect the romantic aspects, or were you able to keep things like, on separate tracks?

I mean, that kind of was the issue, I think, in a lot of ways, because a lot of things got clouded by our commitment to the business and to our family, which might sound strange. But when you think about it, you know, he’s basically the CTO, the chief technical officer, I’m the CEO running the business side and building the business. And we’re trying it, we’re doing this so we can have a, you know, a legacy and a good life for our family. So when you think about trying to take a break from your business, right? You can’t do it. Because you’re taking a break from supporting your family, right.

And here I am as the CEO, and I would like my CTO to have a break so he can have a life. But every time I would encourage that, nothing. He felt the same way. It’s like you almost felt guilty, right? Taking a break from this thing that we were working on so hard. It was like a hall of mirrors. It never made us doubt it. And you know, frankly, Laura, maybe it should have because I know there are a lot of people who look at us and were like, how did you hold on? Not to the marriage, to the business — so long over, through so many obstacles.

And I think it was just almost a tunnel vision of we’re doing this because we believed in it. We’re doing this because we want to make our kids proud, right? We’re doing this because we want to provide for our kids. And you get a certain distance down that road, and it is very hard to turn around and go in another direction. And I think, you know, it was not the only reason that our marriage ended. But it certainly made it hard to have a personal relationship that didn’t revolve around that because it was so fundamental to who each of us was.

We both really liked what we did in the business. We did joke about this. It’s like, you know, something that’s really cool is if you have a thought at 11:30 at night, you can just turn to the other person and say, Hey, let’s do this tomorrow. So it really simplified things. Butas I’ve grown, you know, as a business leader, and just in in my life, I’ve realized that the delineation between parts of our lives is really important.

We liked talking about the businesses. As a matter of fact, I think as the years went on, that became the — you know, that and the kids right became the conversation topics that we were most comfortable talking about. So we kind of let, I think, other things slip. And I take absolutely my share of the responsibility for that. Though honestly, as I think back, I don’t know how I would have had the energy have the bandwidth to maintain that part of a marriage. And that’s very sad.


ALLISON And each person deserves more than that in a marriage, you know?

Yeah. So what did you first notice? Were there cracks in the business partnership before there were cracks in romantic partnership?

It’s — I don’t even know if I would call it cracks as much as just sort of atrophying in the personal side, right. And I would tell myself for a long time, because you hear all these stories: oh, you know, you get married, and whether you’re working together or working in different jobs, you know, you’re busy, and you’ve got young kids and nobody has sex anymore. And nobody has, you know, it just like, that’s just what happens, right?

And then 20 years go by and your kids grow up, and then you look back at each other across the room and go, oh, I think I remember you, you know. But that’s kind of the funny joke that gets told in the movies. And it really, you can’t just turn around after 20 years and look at each other and say, okay, let’s pick this up where were we left off when we got so busy.

I think we just kind of chose to focus on the business stuff, right? And the kids, and you realize that you have to pay attention. And you have to slow down. And it was also very hard for us to slow down and do personal stuff. We tried but, you know, every vacation we would take — it was what I would always call a functional vacation, right? You’re going to visit grandparents, or it’s a holiday or something. So things like date nights, things like, you know, just trying to get away, just the two of us. It was very hard for us to step away from the work and take our heads out of that.

Okay, so was there a moment that you can recall, or an incident, where you thought, we have to end one of these: the marriage or the business.

Yeah. Like I said, I haven’t really talked about this publicly. So I’m trying to be respectful and also authentic. It was definitely the marriage first. And I think, again, it was, it was just a matter of not the right fit, right? I think I didn’t, I honestly think if we weren’t out there needing to have children and procreate, that nobody should get married till they’re like, 50. Because you just don’t know yourself. You know, and I think now, I mean, I really feel like, wow, I didn’t know enough of myself to promise myself to someone else.


ALLISON: And the really, I think, the sort of intriguing thing — which is kind of painfully ironic, too — is that my role in this company has been so transformative for me, and it’s what’s helped me realize who I am and what I’m capable of. Now, I, if I had a different job, I might have had the same realization. It’s just, everybody deserves to have a partner that, you know, you’re the right fit for them.

And so when we decided to separate, one of the very first conversations we had was, look, we have, you know, a business relationship. We have a parenting relationship. And really, we still, once the wounds healed a little bit, we still had a friendship. I mean, our whole life together was based on respect for each other and a friendship. So we’re like, well, you know, 75% of this situation is still something we’d like to, you know, work on. And that I think that was, it was comforting for me. There was something to hang on to there even in the face of a lot of things changing.

So he moved out and found a place right around the corner. Again, never any daylight between the two of us about the priority that our children are, so wanted to make sure he was close by and the kids could stop by and everything. Even before COVID, we were in a remote work environment. It was pretty opaque to other people. And in fact, we agreed to wait about a month until we told the folks on our team because we wanted to present them with a feeling like, oh, wow, y’all separated a month ago, we didn’t even notice, you know?  So that as compared to saying, hey, this is happening, you know, tomorrow and then people freaking out about what does that mean for the company?

LAURA STASSI Are you all still in business together?

ALLISON No, he’s no longer involved in the business.


ALLISON We thought we could make that work for a while, but it just became too difficult. So he ended up leaving the business at the end of 2019. 2019 was a hard year, right. And I remember thinking to myself, 2020 cannot possibly be any worse. And then 2020 strolled in the door. And he had a new job, but that job faded away. All of our kids who were at college got sent home from college, obviously; we had two in college and one in high school. So it went from me and in our youngest, in high school, living in our home to overnight, my daughter and her boyfriend come back from college, my son comes back from college. And my ex, we, you know, we looked at each other, and we said, we have college tuition to pay and he’s — like I said, his job had disappeared in the face of COVID. And so he moved back in, you know, to a different part of the house. And I had no question about whether that was the right thing to do. And yet I tell people, and they’re like, I’m sorry, are you kidding me? And to me, Laura, it is the perfect illustration of. what does family mean?

It sounds like you have a pretty compatible, companionable relationship. So I’m wondering, what was the trigger, I guess, that made you think, no, we really should not be working together; we not only have to be divorced, we have to end our business relationship.

Small businesses evolve and grow in different directions, at different speeds. And it’s not uncommon for, especially for a software company, for the founder who started it either wants to go on and do different things, or the company starts to go in a direction where they’re like, yeah, it’s not really what I signed up for. So it was a combination of not feeling like that was the right fit for him professionally anymore.

It’s not like we’re, you know, sending each other flowers every day. But we are grown-ups. I say grown- up, I just think that’s what it is. You know, it’s like, this is someone who was meaningful in your life for many, many years. The two greatest things in my life, I think, are my children and what I’ve been able to accomplish with this business. And none of those would have been there if I hadn’t been in partnership with him for all those years.

You know, the concept of failure is something that you talk about a lot in the entrepreneurial world. I think it’s a really dangerous word to use in regards to personal relationships and divorce, because I think it just carries so much freight. And it’s such an opportunity to point fingers and blame. And I think people change. Sometimes people grow together. And sometimes they grow apart. And I think that is maybe the best, simplest clearest definition of why not just marriages, but relationships, evolve and go in different directions.

That last thing Allison said? She was repeating what her mom told her when Allison was in high school and her parents split up. Today, Allison’s business is going strong, and things are bright in her personal life, too. We’ll hear more about that in a future episode.

Have you ever had to go to work and act like everything’s okay, even as your personal life is totally falling apart? Have you ever had to do that when the person causing you such love anguish is also your business partner?

KAREN My staff would look at me; my eyes would be swollen and everyone would say, are you okay? Are you sick? Oh, let’s add some more to the fire here. This is a family business. My daughter, his sons, my brothers — they all work there.


We’ll hear from Karen after the break.


LAURA STASSI When it comes to mixing business and pleasure, Karen has done it twice. The first time was early in her career, after marrying at age 21 and landing a position at a homebuilding company.

KAREN I was there first as a salesperson, and then he came into it. But he and I were already married at that point. And during the time that we were together, we had three children. And we — it was the housing industry here. You can never count on the housing industry, as much as it’s near and dear to my heart. The ups and downs are horrendous. So it was back in the late ‘70s, ‘80s where, you know, there were the crashes. So I chose to exit and have children and then go back. And then I ended up leaving the company — which was better for both of us, I think, because it was hard working for my husband. And that’s what I was doing.

Karen and her husband were married for over 20 years before splitting up. Eventually, she met someone else.

KAREN 15:11
We were both in the same industry. We’re both in housing. And he was in a family business. And I was working for another company. And we got together, and he decided to leave the family business. And I left where I was working, and the two of us chose to open up our company. And that was a little odd and different working together, because we hadn’t. And we kind of learned habits and whatnot that we both possess, and our work style. But we clicked with the company, I brought in sales, marketing, human resource; he brought in the knowledge of construction and home building, budgeting. Together, we had such a passion to make this company work.

The relationship grew. But not only that, the company grew by leaps and bounds very quickly. We were getting national awards. We were in the spotlight; we were on a reality TV show, “The Extreme Makeover.”

Oh, you really were?  I thought you were talking now. Wow.

KAREN 16:25
No, no, we really were, during a time where the industry was at the bottom. It was 2007, I believe, 2008. Where, you know, housing was terrible. We agreed to do it because we really felt our little town needed it desperately. And so you know, we just we kind of flourished. A couple years into the company, we decided to get married.

So when you started this company, you were a romantic couple.

KAREN Yes. We were living together.

LAURA STASSI Okay. And so at any time did the business interfere with the romance? Or did the romance interfere with the business? Or was it just – you know, what is it, cooking on gas, cooking with gas, as they say?

KAREN 17:11
I think we were cooking with gas. I think we were just flying high. We worked really hard. We kind of saw things the same way. We had a lot of the same beliefs. And we cared about our people. We cared about our customers. We were doing really well.

Okay, so wait a minute. You’re cooking with gas, everything’s great. And you’re living together. Why did you decide to get married?

KAREN 17:36
Now keep in mind, I was in my 40s. So in my 40s, I still felt the desire for marriage. I think we hadn’t really talked about marriage a whole lot. We were very comfortable where we were. He had kids, I had kids, they were all gone. So we didn’t have the blending of kids living under our roof. But friends, everybody we knew was married.


KAREN And now we’ve got a company together. So we’ve got responsibilities with the company and to our staff and to each other. And it just seemed like it was the next step. It made sense to just make it official. So we did. We were married for 14 years, I think, when it happened, you know, the wife’s the last one to know kind of thing. But I was devastated. Just devastated.

He felt for somebody else. It was through work, but it’s not somebody local. He truly fell in love with somebody else. And you know, it was one of those things, almost like a whiplash. It’s like what? Yeah, that can’t be. And then I started going back and more and more over the last, you know, eight years, seven years. You know, maybe I wasn’t the best wife, and maybe it wasn’t all his fault. And, yeah, there were issues that we tended to not really address or look at. We let life get in the way. I took him for granted. Perhaps, you know, I believed that he would always be there. I won’t take all the blame because I was there. And I, to this day, I believed that we could have made it work.

Okay, so you said looking back, there were issues. Do you mean just in the romantic relationship or as business partners were there tensions?

KAREN 19:34
it became clear to me that we had different visions. You know, we both looked at the company as our baby because we didn’t have kids together.


So this was our child that we nurtured and grew, and it was going off to college. You know, it’s kind of on its own, that the company was running well, and yes, we participated in major decisions, whatnot, but the company — I mean, to this day, the company is doing fairly well. So I think all of that was okay. But we tended not to nurture that relationship over time. I remember one day coming home saying, wouldn’t it be interesting if we didn’t work together, and we could look forward to each other coming home after work? Because we were 24/7 for 20 years, you know, or whatever it was. We were always together.


And I think that gets on your nerves, sometimes. I think if I walk away from this with one lesson, I hope that in my next relationship, if there is one — and I do hope there is one — I hope I am able to stand up for myself more and speak my mind. Because I was one of those people that would just swallow it. You know, I would just turn the other way or not view it as, this is something that should be addressed. I never would fight. I would just take it.


And I’m sure that wasn’t fun for him either.

So did you feel like you were an unequal voice in the business?

KAREN 21:16
Somewhat, but I’m not going to throw that on him. Because he was a big supporter of my input, my views, my ideas, my growth. But then it got to a point where I was going outside the company, within the industry, on more of a volunteer basis. And I got very involved in my national association. And I found where I had wings, you know, to fly within that organization where I was somebody, and just me. I grew individually, within the marriage, but outside of the company. And I tend to think that some of that may have left him feeling less of someone that I needed, perhaps. I don’t know that. I don’t know that it mattered, but I wonder sometimes. Maybe he was left alone too much. I don’t know. I will say that when I discovered that I was losing him, I did anything and everything I possibly could to save the marriage.

Okay, I just want to say, as someone who was married for a long time to one person, I think it’s very natural – in particular, for women — to sort of make excuses. But we sorta still want to protect the reputation of our exes. And I’m hearing that a little bit from you because, and even though, you know, it’s been eight years. But I still think especially, somebody you were married to who was also your business partner. I’m not a therapist, but I want to give you the freedom to be mad at him.

KAREN 23:23
Oh, I’ve been there. Trust me, I’ve been there. Keep in mind, here’s, here’s the caveat to all this. There is — there’s one more piece to all this that we have not really disclosed. And that is we are not divorced.


We are separated. Because we didn’t feel it was good for the company to divorce.


So we are working together and running this company together, I have pulled out a lot more than I normally would have. Because it’s still hard for me and, you know, the personal aspect of. I was rejected. And you know, my family and friends say, oh, Karen, come on, stop going there. It’s time. It’s time for me to get over that. But he was my best friend.


And I use the term, he knew me better than anyone on this planet. And he rejected me. So there’s that heartache. And you know, I’m not good enough, pretty enough, sexy enough, smart enough. All those things, those messages keep going on in my head. I told him recently, you know, I’m finally seeing the light at the end of the tunnel here because I’ve been in this darkness for so long. And we don’t talk about it. He and I — we don’t discuss what our personal life is, where we are with life. You know, we kind of keep that quiet. I do care about him. I don’t want to be with him anymore. You know, it took me this long. He made that decision a long time ago. It just took me a little longer.

Yeah. So tell me a little bit about that. You said you discovered it. So it doesn’t sound like he was forthcoming with the fact that he was having an affair. Let’s just put it out there. It might not have been a physical affair. It was an emotional affair, but it might have been both. But there was something going on that he should have told you about.

KAREN 25:41
Yes, he should have. And it wasn’t until I discovered it that no, and that it, even then it was well, you know, I feel a connection to her and this that the other. But I don’t think he knew what he wanted at that point. I think he wanted us both. I don’t know, I can’t speak for him. I don’t want to trash him. He’s my business partner. And I still respect him. And I told him, I’m angry. I’m bitter, but I still care about him a lot.

Sure. It takes me a long time before I am to the point where I can be friendly to somebody I was romantically involved with who I thought did me wrong.


If my financial future was also tied in, you know, my profession was also tied up with that…

Yeah, it’s complicated.

Yes. Karen, what I want to know is …

Yes …

What was it like going into the office the day after, like the first big blow up?

KAREN 26:41
Hell. It was horrible. It was horrible. For several years. I was embarrassed. I was ashamed. It took me several years. And I was MIA. You know, I, I didn’t go in. I didn’t care. I lost my passion.


And for the last seven years, I had no passion. This last year. I’m starting to breathe again. I’m putting makeup on. I’m losing weight and doing things for me. And I’m looking for that next chapter. I’m ready. I want it. I’m ready for divorce now, and he knows that. We’ve talked about it. It’s time. I’d like to pursue the divorce and retirement. I’d like both.

Karen points out that this was a second marriage for both her and her estranged husband. So they had been especially mindful about having all the legal paperwork in place for both the love and the business partnership. And despite everything she’s been through on the love front, she says they work well together and that he’s been supportive.

Karen says she still believes in love. And she wants to think there’s another relationship in the cards for her. As for going into business with a romantic partner? She’s not going there again.

Dating While Gray’s audio production and mix is by Steve Lack: Audio. For more on the show, check out datingwhilegray.com. That’s where you can find the latest episodes, plus the archive of previous episodes. You can also find links to send me questions, comments, tips and true stories through email and voicemail. You know I love hearing from you. While you’re there, sign up for the free Dating While Gray e-newsletter, delivered every Friday to your inbox. That’s datingwhilegray.com. Laura Stassi. Thanks for listening.

Support for this episode of Dating While Gray provided by Edgespace, a small business offering financial management solutions for businesses of all sizes. Whether you’re an emerging business or an established company, Edgespace can help with your accounting needs. Learn more at edgespace.com.

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