What to Expect When You’re Expecting a Business

Introduction:

This week, Paul Downs, Jennifer Kerhin, and Liz Picarazzi discuss the challenges couples face when one spouse is building a business. Liz says it was important to let her husband know that she spent years working on a business plan before leaving her corporate job to start her first business. Paul explains why, when times have been tough, he hasn’t always shared the bad news with his wife. And Jennifer says too many couples planning for one spouse to start a business focus on best-case scenarios rather than the more likely worst-case scenarios. She also suggests some important questions for couples to ask themselves, including this one: “Will she still have faith in him if the business fails?” Plus: Businesses fail all the time, of course, and Paul explains why he thinks it’s usually for one of three reasons. And four years after the pandemic arrived, we take a look back: What was each owner’s toughest moment? What was their best decision? How have their business models changed?

— Loren Feldman

Guests:

Paul Downs is CEO of Paul Downs Cabinetmakers.

Jennifer Kehrin is CEO of SB Expos & Events.

Liz Picarazzi is CEO of Citibin.

Producer:

Jess Thoubboron is founder of Blank Word.

Full Episode Transcript:

Loren Feldman:
Welcome, Paul, Jennifer, and Liz. It is great to have you here. We’ve just passed the four-year anniversary of the arrival of Covid and the pandemic. In our conversations here, we often note that much has changed since then. But we rarely go back and talk about the upheaval that Covid brought at the time. And with that in mind, I’d like to ask each of you three questions. One, what was the most difficult moment for your business? Two, what was the best decision you made during that period? And three, how’s your business model different today than it was four years ago? Anybody want to go first?

Paul Downs:
I’ll go. I remember hearing the news that Italy was kind of closing its doors and shutting down, and going, “Huh?” And then, when I heard the NBA canceled their season, I was like, “Oh, this is for real.” And then shortly after that, I realized that, in a world of people staying home, the likelihood that they’re buying huge conference tables is gonna go way down. And that was my worst moment: thinking that the business we do is simply just going to be shut down, like no one will want my product ever again.

Loren Feldman:
If nobody’s going into an office, there’s no need for a conference table.

Paul Downs:
Right. And fortunately, I was completely incorrect about that last one. Our business went down about 20 percent in 2020. But actually, March and April were the two best months of the year. We continued to get orders. And what changed about my business model was nothing, except the clientele has changed a lot. Nowadays, we do a lot less of customers in the Northeast: sort of the Boston, New York, Washington quarter, with the exception of government. But the private industry in that area has really slowed down.

And we’ve seen significant growth in a set of clients who are from western states, southern states, but also ideologically more conservative. In other words, people who did not react to the pandemic. First of all, they didn’t react at all for the first couple of months. And second of all, there has been an emphasis, I think, in other clienteles of just like, “Hey, we’re gonna continue with our office life the way it was.” So yeah, I never really had a terrible moment, because as soon as PPP came along, and I got some of that money, I never was short of money for the next three and a half years. So, it wasn’t nearly as bad as I thought it was going to be. But in March, yeah, it was pretty crazy.

Loren Feldman:
Paul, you’ve spoken here, in the past, that a lot of people told you initially, when you were concerned about your business falling off, that you should get into the business of making tables for people setting up home offices. Everybody was talking about the pandemic pivot. You came to the conclusion that you should not make one of those pivots. Was that your best decision?

Paul Downs:
I think that was a good decision. It’s a decision that I’ve had to make continuously for the last 30 years, which is: We have a shop that’s got a lot of tools in it that could be making a lot of different things. And the constraint is not what you can make, but whether you can shoulder your way into a functioning distribution channel and then compete with the people who are already in that channel. And as it turns out, custom conference tables is not a heavily populated channel. There just aren’t very many people who can do it.

Whereas when Covid came along, all the people who had been doing home offices suddenly had a bonanza.I suspect, and I still believe, that it was going to be very difficult for me to pivot into that space. Because most of the people who suddenly needed a home office are not necessarily the demographic we serve when we’re making things. I’m not going to be able to compete for and deliver a $400 sit-stand desk. I just can’t do it. And that’s what looked, to me, like the main market was going to be for the next few years: people trying to spend their own money to outfit their own home office. And that’s a much more budget-constrained customer than I normally have.

Loren Feldman:
Liz? Jennifer?

Liz Picarazzi:
Sure, so when I look at my most difficult moment, it was the feeling of quicksand, or of spinning my wheels, that I had for probably eight to 12 weeks when Covid first hit, and we were in lockdown. So my business, my sales went down very quickly. I had a very large shipment of inventory that had just come over that was about to be put into a warehouse where I didn’t have a very good relationship, to be nice, with the warehouse owner. He tried to extort me, before putting all of the bins in the warehouse, raised the price on me. And that was really difficult because I knew that I wasn’t going to be selling that many of those bins, and I was going to have to start paying rent on all of them. And it was a huge amount of money.

One thing I remember from that time is attending seemingly endless webinars with banks, Chambers of Commerce, the SBA, the Business Library, you name it. Every webinar that was available, I went to, because I had it in my mind that there was some bit of information I would hear about PPP that was going to put me at an advantage when it came time to apply. That turned out not to be the case. When PPP checks first went out, and I was not in the first tranche, as most small businesses were not, I was really devastated. I can remember—I think it was the Saturday after those first checks went to, like, Shake Shack, Ruth’s Chris.

I know that the Treasury Secretary, Steven Mnuchin’s wife, who had a business painting pictures of his ties that he wore to big meetings in the White House or wherever it was he went, he tried to use that in his example of how well PPP was going. And that made me literally hysterical—like crying hysterical. I was so bothered by that whole thing. And then really, the last straw was, I felt like with my bank, and with other financial institutions, I was not getting the responsiveness that I wanted. I was feeling sort of desperate. And I remember one day not being able to log into the bank because I had forgotten my password, or my password was changed. And suddenly I just had no access to get into my finances. And I had to just unplug, like, for a week, completely. I had a complete breakdown. Okay, and now I’m in the bad spot.

And the worst part of it: I also had laid off my small team of employees. So once PPP came around, I hired them all back. Luckily, as we headed into later in spring and summer, people started thinking more about their trash. When they’re at home, they’re working from home, they’ve got their kids at home. If you see mountains of trash out front, some that’s not being picked up, you’re gonna think about it more. So our sales went straight up. We sold through everything that we had in the warehouse. And it ended up being really positive.

But for a little bit of that time, I felt doomed, and I felt like I was in quicksand. And for an entrepreneur, as we’re all used to trying to solve problems and get past them, I felt like nothing that I did was going to help the situation. And that was a feeling of powerlessness that, I don’t know, I guess, entrepreneurs don’t feel that as much as the average person, because we’re optimistic about what we can do.

Loren Feldman:
Was there any particular decision you made that you look back on and think was an important right call?

Liz Picarazzi:
Yeah, so one of them was to look at this municipal market that I’m now in in a way that was very long-term and strategic thinking. So shortly before lockdown, there was an article in The New York Times about how the Department of Sanitation was going to be rolling out a big trash containerization effort. And I zeroed in on that. And I was like, “There’s a huge market here, and I’m gonna go after it.” Then when Covid hit, that whole program, and many others, shut down.

But I kept my eye on that. And we actually built a couple of web pages devoted to containerizing New York City street trash for a program that didn’t even really exist yet. And we had that kind of program and the marketing for it locked and loaded for when things got back up and running and that city program was resuscitated. We were ready to go for it.

And that was sort of a decision that, when I took it, I think my team was like, “Oh, this is so speculative. Is this thing really a thing?” You know, it was just in the paper and that was it. And that decision was probably one of the best that I’ve ever made. And it was just the optimism that that opportunity I saw pre-Covid would come back into play. And it did.

Loren Feldman:
And that reflects the changes in your business model since then as well, I would think.

Liz Picarazzi:
It definitely does. So probably, I’d say over half of our business is now with cities and municipalities, and not just in New York. So that was a gigantic shift: seeing customers where I previously didn’t see them. So for the first almost 10 years of Citibin, I didn’t really think of cities as a potential customer. It just didn’t really cross my mind. I was so focused on homeowners. And so that was a gigantic change to our business model, definitely for the positive. And that’s really where my biggest growth area is now.

Loren Feldman:
So Jennifer, you’re in the event business, I’m guessing you had a difficult moment in the early days.

Jennifer Kerhin:
I did. But when I hear Liz’s story, I think our outcome was, in many ways, similar. The events industry shut down pretty quickly. And we spent the first four months refunding millions of dollars from exhibitors and attendees. And at that time, I definitely thought my company was probably going to be gone if this extended for a year. But in the similar ways with what Liz said, and maybe a little bit of Paul, we leaned into the technology aspect of virtual events. And virtual conventions in our association clients became a big thing.

And so instead of a lot of meeting planners out there, who threw up their hands, we definitely leaned into this technology. And we have had exponential growth since then—not a new market. It’s the same clients, but a new service. And so Covid, as much as I hated those first four months, it opened up all sorts of possibilities for us. It also made me stronger as a CEO. That whole phrase is: Adversity can make you stronger—unless it kills you. And I really thought it was going to kill me. But it has made me a much better CEO by living through that time.

Loren Feldman:
Is there anything in particular you would point to?

Jennifer Kerhin:
I think the prioritization of what’s on fire right now, what needs to be done. And then taking advantage of an opportunity. And so simultaneously dealing with a fire, as well as seeing, “Okay, once that fire’s put out, what’s our next step?” So in the present, dealing with the present, but then also looking a year down the road. We had a war room every morning, because events were just going away every second, and bringing the top leaders into that war room every morning and figuring it out, getting rid of the fires, and then setting a plan for the future, it made me much stronger as a CEO.

Loren Feldman:
With events closing, what was the purpose of the war room? What fires were you putting out?

Jennifer Kerhin:
So there are a lot of contracts. You can’t just cancel an event when you have 5,000 people coming to a city. What happens to that contract? What happens to the people who spent their registration dollars to get there or the exhibitors to get there? What do they do? What if they ship their equipment and it’s sitting in a warehouse? So even though the events are canceled, there is still a significant financial component to unraveling that.

Paul Downs:
So when customers are booking, are they depositing money with you? You said you had to refund millions of dollars. Do you generally have an enormous amount of cash sitting around for that purpose?

Jennifer Kerhin:
No, it goes into our association bank account, but we’re the conduit, the information, the customer service, the communication to the exhibitors. So the association clients, it was in their bank account, but we had to figure out how it was going to be done, how much it was.

Let’s say you paid $1,000 for a booth, but you’d only sent in the deposit, which was $1,000. It was a full amount. Can we roll that over to next year? Can we convince you that, “Let’s keep this money for next year”? The cancellation terms. So it wasn’t our money, at no stretch of it. It was our clients’ money. But walking through that process and trying to get as many people as possible to roll over to next year was a big part of those first few months for us.

Paul Downs:
How many did? I mean, I would have been like, “Hell no. Who knows what’s going on with this thing?”

Jennifer Kerhin:
Most exhibitors did.

Paul Downs:
Really? I guess everybody was happy that PPP showed up, if you’re not scrambling for every dollar back.

Jennifer Kerhin:
I think it was more that they had already accounted for spending that money. And so they didn’t know what the future looked like, so they thought: Well, they’re still gonna exhibit. They might as well just put it in the future, because who knows if they would get funding to exhibit next year?

Loren Feldman:
Was there any particular decision you made, Jennifer, that you look back on and think was a particularly good one?

Jennifer Kerhin:
The technology aspect, by far. Virtual conventions are here to stay, especially with ones that are educational in nature. Trade shows are perfect places for exhibitors. But also, if there’s a significant educational component to the conference, they have gone into a hybrid state. And now we have built an entire department to provide technological services that had not existed beforehand.

Loren Feldman:
I think that might surprise some people. Events are back. People are going to conferences. Why has virtual continued to be an important part of what you offer?

Jennifer Kerhin:
So if you think about the average association, let’s say they have X amount of members, and they might have anywhere from 2 percent to 20 percent who come to the event. There is a significant portion of an association’s membership that can’t always get to an event, and it’s for all sorts of reasons. Budget is one part of it, but that’s not the only part. There are many reasons why people can’t get to a meeting. And so an association, by its nature, is trying to fulfill obligations to all of its members.

And so if you have an in-person event, fantastic. But then if it’s education, especially if it’s accredited education, you can reach a whole section of your membership that maybe you didn’t know how to do before. And especially with the rise of DEI initiatives, there are all sorts of equitable aspects to a virtual conference for people who are unable to get to an in-person event.

That doesn’t take away from the fantastic elements of an in-person event: the networking, that face-to-face that you just can’t duplicate, the exhibit hall floor. But the educational side really helps support DEI initiatives of associations. And so the virtual-convention side, when it comes to the educational components, is still moving. It’s a startup in the events industry, basically, because it didn’t exist until a couple of years ago. And it continues.

Liz Picarazzi:
I find that so fascinating, Jennifer, because you’re saying between 2 and 20 percent of a membership would go to a trade show every year. What about those other 80 percent who also want to get those accreditation or those education credits? If they didn’t have the money or for whatever reason they couldn’t go, then they just wait until the next year to hopefully be able to take those classes. Now they have the opportunity to do it virtually. So I would just think there’s so much more inclusion in this, that it’s really very impressive and pretty exciting, too.

Jennifer Kerhin:
And associations have, for years, had some sort of accredited education, like a library. They had some sort of Zoom meeting, like a webinar. Webinars have been around for a while, right? The issue is, at a conference, you are creating incredible content. And it’s only getting consumed once—the keynote speakers and motivational speakers, the day-to-day practical concurrent-session speakers. That now doesn’t have to only be consumed once. You can capture that content—that’s what we call it, “captured content”—and use it again and again throughout the year for the members who couldn’t make it. Pretty cool.

Loren Feldman:
Can you in any way quantify for us, Jennifer, how big a portion of your business you see the virtual side of things being going forward?

Jennifer Kerhin:
I think it could take over the size of my company. It could by far take over my current annual revenues now. Honestly, it’s a whole section that I have not leaned into enough, from a marketing standpoint. For the past couple years, as you wear so many hats, you can’t wear them all at the same time sometimes. And so I have focused on infrastructure the last few years. But I think if I put some more money—and it’s coming—into marketing, that department could take over the entire size of my company right now.

Loren Feldman:
Well, thank you. I think you kind of made the point that I was hoping we would make, which is that even a horrific event like the pandemic can lead to all kinds of unexpected outcomes, and many of them oddly positive—which I think is the case for all three of you.

So let’s move to another topic. I read an interesting question that I saw posted on the small business subreddit. I was intrigued by it and wanted to hear what you guys think. Let me read it to you. It has to do with people who are spouses of entrepreneurs. The question is:

“My fiancé will start a business at some point after we get married. I’m highly risk-averse. How can we build in resiliency and communication during the tough startup years? My fiancé and I have been together almost four years and are planning for the future. He’s an incredibly business-savvy engineer with a life dream to start a business. Everything he does is well researched and thought out. I am naturally risk-averse. My life goals are less ambitious and more in the here and now. We have dreams together …

Two sets of questions: “The first one is how can couples set a business up legally to protect their personal finances, particularly the finances of a spouse that is not legally involved? Things like setting up an LLC, avoiding sole proprietorship, putting pre- or post-nups in place.”

Anybody have any advice on that particular question?

Paul Downs:
Well, we’re not lawyers, so I don’t know. But I didn’t do any of that stuff, if that’s helpful. [Laughter] I mean, on the face of it, a lot depends on what phase of life you’re in when you start a business. I started when I was very, very young, and had basically nothing dragging me down. I wasn’t even married, although I was living with my girlfriend at the time. We later got married. I just started a business kind of on a whim, and it all worked out.

But if these people are viewing their marriage as a merging of two asset classes, as you might put it, then sure, I think it’s important that they define what’s hers, what’s his, what’s theirs, and consult with lawyers to make sure that if the business fails, then that doesn’t spill over anywhere where it doesn’t need to be.

And I think also that communication-wise, if he’s going to be committing his assets, or possibly their assets, in order to get lines of credit or anything, that needs to be a discussion between the two of them. And I have never reached this point myself, but I think that there needs to be some discussion going into it as to what failure looks like. So you know when the day arrives, and you can pull the plug, at that point. But I think I’m going to defer to my co-podcasters here, because I think both of them have much better experience with this than I do.

Loren Feldman:
The follow-up questions she has that I want to get to are about communication, which Paul touched on. Do either of you, Liz and Jennifer, have anything to say about the infrastructure aspect of this?

Jennifer Kerhin:
No, no. We can move to communication for me—unless Liz does?

Liz Picarazzi:
Yeah, I think I can touch on this. But I want to hear what Jennifer has to say first.

Jennifer Kerhin:
Oh, okay.

Loren Feldman:
Let me read the question about communication:

“How do couples with a business-owner spouse manage hard discussions about finances in difficult times, particularly during that hard initial grinding year period?”

Jennifer Kerhin:
Well, I’ll take this question. I think the person that asked the question is in the throes of excitement. They are about to get married. There’s nothing more exciting than the engagement and honeymoon period. The fiancé is also about to start a business. There’s nothing more exciting than the thrill of starting on your own. Those two are a recipe for disaster. The passion and excitement will meet the brick wall of reality pretty soon. And so what I would suggest to them is to talk to someone who has had a business fail and have an open, honest conversation.

Because what I’ve heard people say is, “Oh, I’ll work now. I’m going to work really hard. But you’ll have the day-to-day job with the health insurance. In a couple years, we’ll be able to figure stuff out, and then we’ll have enough money. Don’t worry, we’ll take the vacation then.” Well, that’s the best-case scenario. I want to hear the worst-case scenario.

I want them to have a conversation. Let’s say you don’t buy that house after the wedding, and you put that money in the business. And two years from now, that business goes bankrupt. How are you going to feel about your spouse? Is your marriage going to be strong enough to survive? What are you willing to do to keep your marriage alive? Don’t think of the best-case scenario, because we all want to live in the best-case scenario. Think about the worst-case scenario. So that’s my advice. Liz?

Liz Picarazzi:
Yeah, so when I started my business, I had kind of sketched it out. I had a business plan for a couple of years before I left corporate. And part of that was that I wanted my husband to see that I was prepared to launch the business, that I wasn’t just doing it impulsively. So he had a couple of years to see my passion for what I wanted to do and to see the business plan. So when the time came for me to be able to leave corporate, I had a severance. I had unemployment that I was able to get. At that point, he saw it as: This is your opportunity to go for it, because we have this runway in front of us.

So it was kind of an easier decision. If I had just decided to leave corporate to start a handyman company, which sounds insane even now when I look back on it, he would definitely not have gone along with it. We probably didn’t talk about worst-case scenarios. And I could have had that, because my first business I ended up selling and getting out of very quickly. But there still was a messiness in closing that whole operation down that was definitely a strain on the marriage. There was still some money involved, even though I had sold it, and that was a really trying period. The lucky part of it was that the reason that I sold the first business was to focus on Citibin, my current business, and that was doing well.

So the conversation wasn’t, “This thing shut down. What are you going to do now?” It was, “Oh, it’s a good thing you had this other thing going when the first one imploded.” And then, current communications, as everyone knows, my husband, Frank, is my COO. So we talk continually about this. As we grow, the stakes definitely seem higher. You know, taking on a higher line of credit, buying inventory in a much larger quantity. That’s always a big part of tension for us, because he is risk-averse. And I’m like, “We need to prepare for success. Stop having a mindset of preparing for failure, Frank.” And that’s probably a tension we’re always going to have. But I think we understand why the other has that perspective, more than we would have a couple of years ago.

Loren Feldman:
Do you think it’s a healthy tension that gets you into the right place?

Liz Picarazzi:
I think so, yeah. There’s a lot of angst. There can be a lot of angst, because you don’t want to think that your spouse is preparing for failure. And if I really boil it down, when he’s being risk-averse, in my mind, I take it sort of personally and think that’s what’s going on. But really, he’s just being protective of the life we have—you know, the house that we have, which, yes, is mortgaged against our big EIDL loan. But it’s a big tension. And I have to say, it doesn’t work for many, many couples, regardless of whether you work together. It’s a very big area where a marriage can fall apart. And it is really important for this person on Reddit to have their eyes open.

Loren Feldman:
The second part of this woman’s question is, “What do couples where the spouse’s business failed wish they would have done differently in terms of communicating with each other.” Paul, happily, your business did not fail, but you’ve been very open about how tough it was around the time of the Great Recession. You wrote about it in The New York Times, and you wrote a book that was largely about it. Can you tell us anything about how you handled that in your marriage at the time?

Paul Downs:
Sure. One thing about my marriage is that all that was really bad, but it’s not by any means the worst thing that’s ever happened to me. My wife and I have a very severely autistic son, and that’s just a constant challenge. And we’ve been able to turn that challenge into something that binds us together.

So the business failing was a distressing prospect, but it wasn’t… How can I explain this? It just never got to the point where it was actually the worst thing, because it didn’t fail. But we had over the years—we’ve been together for a long time—we just settled into a pattern of how to be married that didn’t require—how to put this—it didn’t require any continuing assurance on my part that the business was going to be this or that.

And part of that is because it started as just an effort to be a reasonably successful artisan. And it quickly grew beyond that, but Nancy’s roots and my roots in business are very humble. And she just was not so worried about—or, at least, I didn’t feel that she was worried about—a moment where income was down or whatever. Because A), she grew up in a household where that happened a bunch of times. And B), we’d had a lot of years prior to that, when I was starting the business, where it just really didn’t make much money, and we just got used to not having money. So it was tough to explain to her every little in and out of what was happening in the business, and I just didn’t do it. But we skirted disaster. So I never really had to confront the consequences of whatever I was doing at the time.

Loren Feldman:
Paul, you and I met because you sent me an email, when I was at The New York Times, saying that you would like to write for the small business blog that I was editing. And you thought you could provide a different perspective because you were running a business that was headed toward bankruptcy. At the time you wrote that email to me, did Nancy know that you felt you were headed toward bankruptcy?

Paul Downs:
I don’t know. I didn’t explicitly say it to her that way. At the time I wrote that email, which was mid-December of 2009, we’d already been through a pretty tough year. She knew it was bad. But she’s not somebody who can really listen to the minute-by-minute, “Oh, here’s how much money we have in the bank account.” And I think that that’s partially because, as I said, she grew up in a household where there were some pretty lean periods. And it would just be distressing for her.

And the other thing is, when you have a child with special needs, one of the things you learn is that something happened to you, right? It just happened, and then you deal with it. And so with the impending bankruptcy, I could see it coming. But at the end of the day, it did not happen. So I never really had to get down and deal with it as the biggest problem of the moment, because we just got out of it. And it just made it possible for me in my marriage to get through that without having that frank conversation. Now, that’s my experience, my wife, my situation. And I would never hold that out as, “Hey, if your business is failing, you should do what Paul did.” Don’t do what I did. I’m not a good role model, in this case. So I think you should ask the other podcasters.

Liz Picarazzi:
I just thought of a situation when Frank was not in the business. It was in my first business, and I was really struggling. I felt really lonely. I felt like no one understood I was the boss. No one understood me. And I remember I came up with this idea: He was in corporate, maybe he could work with me one day a week and kind of see what are the things I’m dealing with and be able to help or advise or at least know what’s going on—and really, very forcefully asking for him to do that. And he said, “No, I need to focus on this job where we’re getting the paycheck. We’re getting the health insurance. It’s paying for our life in New York City.” And he didn’t want to do that.

And, you know, I understand it. But it also shows me, now that we do work together all the time, I don’t feel lonely in the business. Everything that we’re going through, we’re going through together. And I needed to feel more supported. It wasn’t that he was being unsupportive before, but we just had our life structured in a way that he couldn’t just tell his employer, “Oh, I’m gonna go help my wife with her business one day a week,” which I thought would be an acceptable proposal to an employer. And now I know that it’s not. But that was something, just through talking about this, I remember that feeling of like, “Oh, I need to pull him in just a little bit, so he understands more of what I’m going through.”

Jennifer Kerhin:
A couple of specific questions to give this person some really specific feedback: One is, if the company fails, who’s responsible to pay back if there’s any debt? Is this an assumption that the marital couple will do it together? Or that the person who had the business, it’s their responsibility? Second is, how soon after it fails is the expectation that that person who’s a business owner would get a job? And I don’t mean, like, employment, but to bring in other cash, whether that just means taking catering gigs on the weekend to bring in cash. What’s that expectation of a time period? Is it a month? Is it two years until they get their feet on the ground to start a new business? You know, everybody’s different.

Three is: expectations of changes in lifestyle. Most businesses that fail at this level, your lifestyle is probably going to change dramatically. Are you on the same path of, “Well, we still need to take that luxury vacation on the cruise?” Or, “Do we need to cancel it?” And then the final one, I would say, is: Where’s the health insurance coming from? If the health insurance is from the spouse that’s not the business owner, and they had expectations to do something themselves—another job, staying home with children—there’s all sorts of reasons to relook at that, because health insurance is a serious aspect on the marital side when a person wants to start a company. And who’s going to provide that? So I would think those are just a couple questions I would have them really talk through. Yeah, I think that that would help them if the business failed.

Loren Feldman:
Those are great questions.

Paul Downs:
I guess another one would be: Do you believe in the husband’s ability to start a business? I mean, without knowing the particulars of this person’s situation, it’s really hard to answer it, because any answer that’s generic just can’t really account for the particulars of a couple, a business, an existing situation, what the future looks like. But if you’re risk-averse, and the husband’s like, “Okay, I’m a practicing engineer, but I want to start a hot-air-balloon tourist company,” or something that he knows nothing about, that, to me, would be very important.

One thing that I’ve enjoyed over the years is that my wife has never doubted that I could do a reasonable job in my business—maybe when I first opened it, but we had no mortgage or anything at that point. It didn’t really matter if I failed, though. By the time we got to having kids, the business was not particularly successful, but she just had basic faith that I wanted to work every day. I worked hard. I tried. I was reasonably good at what I was doing. The business was growing, even if it was slow and it wasn’t very profitable. So having someone who has faith in you is pretty important to success, and just being able to manage the stress. So I would hope that this person who asked the question basically has faith in their partner, that they can get through this and that the marriage won’t suffer because of it.

Jennifer Kerhin:
Well, Paul, the interesting question is, if she does have faith, she’s in that honeymoon phase. She’s lovey-dovey: “Oh, I love him. We’re gonna get married, and he can start a business.” She’s not thinking as smart as old married people like ourselves. But the better question is: Will she still have faith in him if the business fails? What if it fails? How does she look at him as a husband then afterwards?

Paul Downs:
Well, I can give her some advice for that, which is having written for The Times and heard from a lot of people whose businesses failed, I came up with a theory of why businesses fail. And there’s kind of three things: the first thing is, it could fail because you just make boneheaded decisions. Whatever, the business you wanted to start isn’t all that smart, or you’re bad at running a business. The second thing is, if the vast forces of the economy are against you, you could do everything right and still get crushed. And then the last thing is just luck. You could do everything right and have a tailwind from the way the economy’s going and just get hit by a bus one day. So those three things are always at a mix in any given business story.

Jennifer Kerhin:
Totally agree, Paul. And yet, so many marriages fail because of money. And so the advice I would give that woman is that—you’re exactly right, Paul—businesses can fail for a wide multitude of reasons that don’t have to do with the character of the man you are marrying. And so, remember that. Because money should not be a reason, in my opinion, that people divorce. But that’s my personal thought—just to keep that in mind for the future.

Liz Picarazzi:
I’ve got another thought, potentially, for her. And that’s: Is there any way her husband can test his business concept without leaving a job? So is there any way he can take on a couple of clients that demonstrate and work through things and see, “Is this viable?” Because that could give her confidence in watching that he can do it.

Jennifer Kerhin:
That’s a great idea, Liz. Great idea.

Liz Picarazzi:
Or like moonlighting. I remember, I did a little bit of moonlighting before I left corporate. And one thing I did was, instead of renting a big office somewhere, I literally rented like a quarter of a desk at a shared workspace. So it was low commitment, in terms of rent. But it put me in the discipline of, “Well, if I’m paying rent at that place, I’d better get my business moving along,” and I was moonlighting it. But there could be ways for him to demonstrate where he’s going with it without it being about, “Should I leave my job or not?”

Loren Feldman:
You guys have provided some great advice here, as I knew you would. We’re almost out of time. I want to hit one more topic before we go, which is: Jennifer, in emails before we gathered today, you indicated that you’re planning a staff retreat and that you’re excited about it. I’m curious what you’ve got in the works.

Jennifer Kerhin:
Yeah, it’s pretty cool for us. We are a fully remote company. And there are a lot of conversations out there in the small business world: How do you manage culture in a fully remote one? Now for us, it’s a little bit different, because we go to different cities to travel for our conferences and trade shows. So we get to see people, but still, there is something missing for face-to-face.

And so we are planning our first ever full-staff retreat: four days at the wonderful National Conference Center in Leesburg, Virginia. We’re very excited. We’ve hired a facilitator. We’ve hired consultants to come in to do training. We’re doing a culinary challenge, where they’re going to be competing against each other. Just the combination of in-person training and networking and collaboration. As much as I love remote work—I’m never going back to having an office—I think that face-to-face is still needed. And I’m pretty excited about it.

Loren Feldman:
When is it?

Jennifer Kerhin:
It is in June.

Paul Downs:
I hope you don’t have another pandemic before then. [Laughter]

Jennifer Kerhin:
Well, and you know, we were in-person before the pandemic. And so we had day-long staff training, but nothing like where we flew people in from different states to do four days of training. So afterwards, I’ll tell you how it went.

Loren Feldman:
You just explained that it’s not like other remote companies, in that you do gather from time to time at the events that you put on. Do you have people who haven’t met each other, though?

Jennifer Kerhin:
Absolutely. I have three people I’ve never met in person.

Loren Feldman:
Wow. And they’ll be there in Leesburg?

Jennifer Kerhin:
They will. They absolutely will.

Loren Feldman:
What’s the culinary challenge?

Jennifer Kerhin:
The center offers this, but they give you different fruits and vegetables and you have to create a transportation-type vehicle, something on wheels, I guess. And then you have to push it—I guess which one goes farthest? [Laughter] I don’t know. It’s just fun. The next day, we’re doing a Mexican night where each team has to make a ceviche and a guacamole. And then we’re testing it: Who’s is the best? So just different team-building things around food. Exciting stuff.

Loren Feldman:
Testing people who don’t have experience working with raw fish is an interesting challenge. [Laughter]

Paul Downs:
I thought she was gonna say they give you a cow. And then you have to come up with a steak dinner.

Jennifer Kerhin:
No nothing quite that elaborate. Just something fun to create a sense of a little bit of departmental competition and pride across the departments. Really, just a chance for face-to-face that’s both training and collaboration. And the best part about the center is it’s all-in-one. The food is part of the entire hotel combination. So you’re really in an enclosed space—not enclosed, it’s huge—but you’re in one area. And hopefully that will breed a lot of collegiality, I guess.

Loren Feldman:
We will be eager to hear how it goes, especially the ceviche. My thanks to Paul Downs, Jennifer Kehrin, Liz Picarazzi—and as always, to my sponsor, the Great Game of Business.