I’ve Never Had to Lay off Anyone Before

Introduction:

This week, Sarah Segal tells Shawn Busse that the other shoe has dropped. A couple of months ago, as she’s shared here previously, Sarah lost two big clients in one week. Now she takes us through her decision to lay off three of her employees, including what it means for the business and what it means for Sarah’s own role in the business. Before the layoffs, she had gotten to the point where she was working on the business—but now that’s changed. “I’m not working on the business,” she says. “I am working for clients. I am getting the job done. I am making sure that we’re successful with our clients, and that is my priority right now.” Plus: We also discuss how to choose a CRM, why Sarah and Shawn’s home cities of San Francisco and Portland have been getting such bad PR, and whether former business owners are employable. “I wouldn’t hire me,” says Sarah.

— Loren Feldman

Guests:

Sarah Segal is CEO of Segal Communications.

Shawn Busse is CEO of Kinesis.

Producer:

Jess Thoubboron is founder of Blank Word.

Full Episode Transcript:

Loren Feldman:
Welcome, Shawn and Sarah. It’s great to have you here. Sarah, we haven’t spoken in a little while. How’s it been going?

Sarah Segal:
[Laughter] That’s a loaded question, Loren. It’s been a lot of learning curves and a lot of education. It has not been the most stress-free start of the end of the year. So, the biggest update I have is that I had to resize my company. I had to let go of three people.

Loren Feldman:
I’m sorry to hear that.

Sarah Segal:
Yeah, I let go of my three top people. I mean, it was trickle down from the economy. We had a number of clients basically say, “A, we ran out of funding. B, we spent our wad on this new project and now we have to tighten our belts until the end of the year.” And for months, I was like, “Okay, I’m gonna be able to get new business. I’m going to be able to subsidize this change.” And it just wasn’t happening in August, because people don’t do anything in August.

Shawn Busse:
It’s the worst month ever.

Loren Feldman:
When you say “subsidize this change,” you mean?

Sarah Segal:
Find new clients, find new clients. And I was optimistic for a long time. And then, when payroll started getting stressful for me, I was like, “Okay, I’ve just got to do it.” None of it was performance-based, because we really had a solid, awesome team. All these people delivered on so many things that, like, now I worry about dropping the ball on. It was out of necessity to make sure that we were going to be profitable. And so that was a really unfortunate experience. I have never had to lay anybody off before.

Loren Feldman:
Oh, these are the very first ones?

Sarah Segal:
Yeah, I’ve never laid everybody off. Like, I fired somebody because of performance, but never laid anybody off because of lack of business. But then, of course, like two months later, we have all of these folks coming at us with new opportunities so that I’m like, “Okay, do I hire people? Do I get contractors?” I’m afraid to step my toe too far into the water now, because what happens if that goes away? So it’s been kind of traumatizing. Let’s put it that way.

Loren Feldman:
How did it go laying the three people off—the actual act of laying them off?

Sarah Segal:
Well, I mean, I am really transparent with my team. I always have been. If a client gives us positive feedback, I let them know. If they give us negative feedback, I let them know. If I worry about them continuing with us, I let them know. They know the ins and outs, and they actually know the retainer sizes of all of our clients. So, anybody on the team would understand that if two major clients go, there’s going to have to be some readjustment.

So I don’t know that anybody was surprised. I think that my top earners were surprised that it was them. But I think it went as well as it could, because they knew that I didn’t want to do it—but in order to keep the roof on, I had to.

Shawn Busse:
Sarah, I’m kind of curious. Did you run at a loss for a while before you made this decision? Or is it like, as soon as you hit that moment of not making money, you made the decision?

Sarah Segal:
No, I saw it coming. So I did not want to run into a loss. I can’t afford to run a loss, and that added stress to me was too much. So, no, I saw it coming, and I knew that if I didn’t make a change that I was gonna be in trouble.

Because I don’t have any funding. I have no bag. I have no small business loans. Money comes in, money goes out. I’m not a giant organization that has a soft pad to land on just in case. I have no rainy day, nothing.

Shawn Busse:
You don’t have any cash reserves for this kind of situation?

Sarah Segal:
Oh, no. Well, last year, remember, I was owned by a larger entity. And getting out of that relationship, it was easy in terms of negotiation, but I still had to pay them our fair share of any computers that we took with us, any software that we had contracted. So I literally finally paid them the final check, like, last month. So I have not been able to put together a—

Shawn Busse:
Contingency.

Sarah Segal:
Exactly. That’s on my plan of things to do. I’m definitely trying to do that. But then, there comes the tax question, which I don’t know how to answer. But from a lot of agencies I’ve talked to, they’re like, “It’s best not to have any cash on hand at the end of the year, because then you get dinged for that.” I don’t know if that’s true or not. I have to talk to somebody who’s smarter than I am. But I just want to make sure that I’m doing the best thing for the business as well.

Loren Feldman:
That doesn’t sound right to me. I don’t think you get taxed on cash on hand.

Shawn Busse:
You’re gonna get taxed, regardless of whether you take it out of the business, or you leave it in the business, because you’re a pass through entity. So really, the businesses that empty out their accounts at the end of the year, more often than not, are LLCs, or multi-partner organizations. And then they’ll basically just start the beginning of the year at zero. But the thing is, in those organizations, it’s an expectation that the shareholders kick in cash if they need it, if the organization needs it. So you can certainly take all the cash out. You’ll pay taxes on it, same as if you’d left it in the business.

And you know, I’m not a CPA here—so anybody listening needs to take that with a grain of salt. But generally, it’s kind of a moot point. The real issue is: Do you have funds set aside for these kinds of situations so that you can ride it out? And how long are you willing to ride it out? Have you thought about that? Like, what’s the goal? How many months of operating expenses…?

Sarah Segal:
Well, yeah, everything I’ve read says three months. Actually, I have a consultant who I’m working with who is helping me figure out what my operating expenses are, what my need to bill is, and all of those kinds of things so I can be a lot smarter, in terms of the cash flow. Now that my team’s a little bit smaller—I mean, I still have a team, which is great. We still have clients, we’re still operating, we’re still doing a lot of new business. But I just want to not be anxious about the next phase of growth. So, I’m trying to get a business degree in six months.

Shawn Busse:
I could probably help a little bit, because I went through this process, too, in 2008. Basically, the bottom dropped out, I had to lay off everybody. We were very small at the time. But still, it’s meaningful. And that was when I was first introduced to the idea of months of operating expenses in reserve. And also, the other really important piece is getting your hands around tax liability—actually understanding on a quarter-by-quarter basis and updating regularly what your tax liability is so that you don’t get this big surprise and you run out of cash.

So, those two things. I think three months OpEx—which was my goal, too, when I first started on that journey—is ambitious, but a good number. It’ll make you sleep at night, if you can do it. I think it’s a little high if your business has long-term engagements. If you are project by project, and they can disappear overnight, then yeah, I think three months is what you want to go for, for sure.

Loren Feldman:
Sarah, did the layoffs, those conversations, go in such a way that you could imagine any of these three top people returning to your firm?

Sarah Segal:
Oh, yeah, 100 percent. I mean, all of them were like, “Yeah, let us know if you want us to consult or freelance or what have you.” But then, all of these three people are really wonderful, talented, skillful people. One of them, I think that she probably looked at the layoff as an opportunity to work on some projects that she wanted to work on—some personal projects. She was disappointed and sad about losing her position, but I also think that she saw, like, “Okay, there’s another thing that I can work on.”

And one of the people was my very first hire, ever. We had gotten to a point where I couldn’t teach her anything. She knew more than I do about operations. And she probably knew this internally, that she needed to go somewhere else to give herself more challenges. Although I’m sure she would consult for me, because even she was like, “Well, you know, the balls are gonna be dropped.” And I’m like, “Yeah, I do. But I’m gonna try to keep them up in the air as much.”

And then the last person, literally, I’ve already had two or three people ask me about her. So I think she’ll land on her feet pretty quickly, in terms of new opportunities. And they were all with me for a decent amount of time, and I will give them all wonderful recommendations. And I have done my part, in terms of introductions to potential opportunities for them. So I didn’t just let them go, take their office keys, and say, “Good luck.” It’s more like, “Hey, come to this event with me. I know there’s going to be a lot of people that you should meet and talk to.” Or, “Oh, I met this person. Let me introduce you.” I want to make sure that they land on their feet, and that when they look back at their career, they go, “Oh, I learned a lot there. I had a good experience. And my boss didn’t leave me high and dry when things got bad.”

Loren Feldman:
How have your remaining team members responded to this?

Sarah Segal:
They have taken up the challenge like nobody’s business. I am just dumbfounded. They’re just like, “Yeah, we got this.” Like, that’s amazing. I love you. You know, there was some anxiety at the beginning. But the way that we work is so not, “This is your role. This is what you do.” It’s more like, “Okay, let’s all learn how to make the gears work.” So that way—this is terrible, and I say this all the time at work—if someone gets hit by the bus, we can keep going.

Shawn Busse:
Can you give us some context? So, three people, is that half your staff? Is that a quarter of your staff?

Sarah Segal:
It’s half my staff. But then we have consultants on top of that. But we’re already talking about possibly having to hire a junior person. Like, literally two months later, it’s like: Okay, we have three, possibly four pieces of new business that may happen in the next 30 days. And if that happens, we’re gonna have to either find contractors—which I’m not a big fan of. I mean, we have a couple who we like, and they’re dependable, and they’re great. But I really prefer working with people who are invested in the business itself.

Shawn Busse:
Yeah, that’s a big hit. Gosh, I’m sorry, you had to go through that.

Sarah Segal:
And the people who we’ll hire are gonna be junior. Because the people who I have, who are running the show now, they know what they’re doing. And I think, quite honestly, they would be disappointed if I brought in anybody who was above them. They do a really good job. So we’re going to be looking for staffers with one year experience somewhere. And I think that the job market is still pretty good for us, in terms of hiring. So hopefully we’ll have some good options when I decide to make that jump.

Loren Feldman:
From what you’ve told us, Sarah, it sounds like you’ve got some potential new business coming in. You’ve got your existing business. You have a smaller staff. I’m guessing you must be working yourself really hard. How are you holding up?

Sarah Segal:
I’m stretched, like, completely. I mean, it’s good. I like what I do. I had gotten to a point with my three additional staff, where I could spend a bunch of time on non-billable things, where I could work on the business. And to be frank, I’m not working on the business. I am not working on the business. I am working for clients. I am getting the job done. I am making sure that we’re successful with our clients, and that is my priority right now.

Shawn Busse:
I think the “on the business” versus “in the business” thing gets overused. I spouted that out for many, many years. And I think it is important to build the infrastructure and to work on strategy and to cast the vision. But I’ve just really come to see that, until you get to a certain size, it’s very, very difficult to manifest that. And I think it gets overplayed in the conversations.

Loren Feldman:
That’s interesting, Shawn, because you’ve put real time and effort into trying to extricate yourself from the business, haven’t you?

Shawn Busse:
I have, yeah, I mean, at great expense. I probably make a lot less money, because I’ve invested in that. But I just—

Loren Feldman:
You mean hiring people to do the things that you used to do.

Shawn Busse:
Yep. Investing in systems. That’s been a lot of it, too: investing in systems that allow us to focus on the work, as opposed to the administration. So, those have all been good things. You know, we got a CRM many, many years ago. We got an applicant-tracking system many, many years ago. We have a whole process for asking for time off. And there’s a ton of technology that has made us very efficient at doing the work.

And I would also say, lastly, we hired a lot of contractors over the years to do the work that isn’t core to what we do: outsourced finance, outsourced HR, outsourced IT. I’m just a huge fan of those things. But I do think that when the business is under 20 people, there’s just a reality that the owner has to play an important part in that. And that varies, what that role is, but it’s really important.

Sarah Segal:
Can you talk a little bit about CRMs? I have a love-hate relationship. I’ve tried a couple, and all of it was like, I’m just daunted by the onboarding process for every single one of them.

Loren Feldman:
Are you using one now or not, Sarah?

Sarah Segal:
I have a trial with one, and it’s called Apollo. I’ve tried another one called Copper.

Shawn Busse:
That’s interesting that Apollo’s positioning themselves as a CRM, because I’ve always thought of them as sort of a data miner.

Sarah Segal:
Yeah, they do both.

Shawn Busse:
Yeah, they want more recurring revenue, like all these tech companies do. But anyway, my guess is, Sarah, your pain is coming from the fact that it’s an industry that wants to capture as much market share as possible. So they all say they can do everything for everybody. And anytime you have a tool that says, “Oh, we can serve everybody,” it means they serve nobody.

Sarah Segal:
I know, it’s like going to the supermarket versus the butcher. Like, the butcher, you know that they’re actually going to know the quality of their meats and their cuts and all of that kind of good stuff. You go to the supermarket? You’re going to get something.

Shawn Busse:
That’s a great analogy. And it’s not even like a good supermarket. [Laughter] It’s like the crappy one that has all kinds of random stuff and not very good quality. It’s a massive pain point for every business I run into. Every client I have either hasn’t done it, or has done it and it’s frustrating. I’d say maybe 10 percent of the customers I run into really have their act together. It’s a difficult space.

But, yeah, my counsel to folks is that CRM is not about the technology. CRM is about human behavior. So, can you train your people to use a tool? If you can’t do that, then don’t buy a CRM. It’s the discipline to use the tool.

And I know myself well enough—and this is the on-the-business-in-the business—that I’m not good at using these tools. I actually don’t think many business owners are good at using these tools. Because it requires a skill-set, execution, discipline, consistency that business owners don’t have. They’re random. They jump all around. You know, it’s like, “Squirrel!” every five minutes or so.

So CRM is not built for business owners, which is why my counsel is: Buy a system that is as easy as possible to use. And then you’re going to need some sort of administrative support. And that can be a virtual assistant, that can be somebody on your team who’s admin- and execution-oriented. And you need to make that person the administrator of the tool. And part of their job is to bug people like me and Sarah every week and say, “Hey, there’s a new contact in the CRM, because it’s tied into your email, and it has no information about it. Where did you meet this person? Are they a lead? What industry are they in? And what’s the size of their business?” You know, so you’re actually doing constant data hygiene, so that your CRM has value.

Sarah Segal:
That’s really good advice. And I definitely see it as something that someone could do remotely. And it’s like, find somebody who lives in a small town in Ohio, or Wisconsin, or something like that, who’s perfectly capable of doing this kind of stuff. How did you select the one that you have?

Shawn Busse:
We did an evaluation process where we looked at all the different features, and part of our criteria was: Is it simple? And so I would build kind of like an XY chart of price and simplicity or complexity. And so in the upper right—which would be high price/high complexity—would be a tool like Dynamics or Salesforce. You know, they could do all kinds of awesome things and lots of integrations and cool stuff. But you need a full-time administrator. You can’t do it yourself. Just full stop.

I think it’s an issue of, you need to find the tool that can most easily be set up to mirror your sales process. And that’s the other piece of advice that I realized I omitted, which is, you need to have a sales process. You need to have a series of steps you go through from, let’s say, prospecting, to inquiry, to qualified lead, to disqualification, to presenting a proposal. You need to have all of the steps mapped out. I would do that long before you start looking for a CRM, because what you want to do is, you want to map the CRM to your process to say, “Will this CRM fit this process and how much work is involved to do that?” I’ve had clients use Salesforce, and it’s like, “Wow, the hoops you had to jump through to get it to work are huge.”

I picked one, which I would put in the basket of—actually, not even CRM, but just sort of like sales tracking. And back in the day, there was Pipedrive. And there was, it was called at the time, Base: super simple sales-process tracking. And then Base got bought by Zendesk. And of course, they keep adding features, and they make it more complex. So, they all kind of arms race up to Salesforce, but yeah, that’s where I went: simplicity.

Loren Feldman:
Let’s get back to our previous conversation. I’m curious, Sarah, you said your operations person leaving said something about how some balls are going to drop. And you said you knew. How are you doing with that aspect of it so far?

Sarah Segal:
I’m actually doing fine. Some of the soft stuff of remembering people’s birthdays and stuff? Yeah, that’s fallen through. And, like, award submissions. This woman—a week ago, I got a box in the mail, and it was another award. And I’m like, “Oh, I miss her.” Because she did all of these award submissions for us, which is like giving birth. I mean, they take a long time to pull together all those details.

Loren Feldman:
Is it worth it?

Sarah Segal:
You know what, it may not be worth it necessarily, in terms of new business. But it is worth it, in terms of making the team feel like they’re part of an award-winning agency. When they have a table with all these awards on it, it makes them go, “Oh, we’re doing something that’s worthwhile.” And you don’t necessarily get a lot of kudos from external sources for all the work you do.

We do have a range of clients. Some clients will be flowering us with thank yous and “Oh my God, you guys are the best. We love working with you.” And some are like, “Okay, thanks. Here’s what I need next.” So, I think it’s important to get some sort of recognition. And it makes people feel like they’re doing something of significance. So I miss her for stuff like that, for sure. And I have good intentions on picking up that slack. But I have not had the bandwidth, currently, to do that.

Loren Feldman:
Are you still able to pay yourself?

Sarah Segal:
Yes, I’m actually paying myself fine. I’m paying myself a little bit better now, because I factor that into my decision-making process where I was like, “Okay, this is the number of clients we have. This is the amount of work we have. I can actually pay myself a regular salary, which is good. And I am not going to hire people unless I can maintain that salary.” So that’s kind of the part of the process that I’m going through.

And we have a couple good things on the horizon. Interestingly enough, those good things are all based in San Francisco. We, because our team is all based here in the Bay Area, have become very well-known for supporting local businesses and events and conferences and all that, because we are physically here. And there are a lot of agencies that say they are based in San Francisco, but then you ask the follow-up question of, “Okay, how many people on your team are based in San Francisco?” And it’s negligible.

Loren Feldman:
You’re doing a big event in San Francisco coming up, aren’t you?

Sarah Segal:
Oh my god, I’m doing two, possibly three big events. We’re doing the APEC conference— is the Asian Pacific Economic Conference. It’s basically 21 economic leaders: everybody from Biden to the President of China. They’re all coming in mid-November for a whole week of meetings and conferences, and we’re expecting 600 to 1,000 members of the international media to descend on San Francisco.

Loren Feldman:
What’s your role?

Sarah Segal:
I am working with the press ambassador, in terms of feeding and wrangling the media. That is our job. So, it’s everything from media-related events to working with them in the filing center to telling local media what roads are going to be shut down because of all of the security. And then literally a week later, we’re doing something called the Fan Expo, which is like a Comic Con, but it’s a little bit more broad. It has cosplay and gaming, and they do them all over the country. And so we’re doing that, and it’s going to have a nice interesting list of thematic celebrities, like Sean Astin from the Goonies will be there, and William Shatner will be there. So we will be on-site dealing with that.

And then we’re in final talks to be the agency of record for a company that does VIP experiences at one of the big stadiums here. So, if you go to a concert or game or something like that, and you’ve paid a little extra for that VIP experience, we would literally have to be on-site to help manage those, which my team, of course, is like, “Yeah, we can do that. That sounds like fun.” So yeah, we’re doing a lot of conferences and events. And honestly, they’re totally exhausting and life-consuming, but they’re a lot of fun, too.

Loren Feldman:
It sounds like they might help get the city of San Francisco a little bit of good PR, which I’m thinking it could probably use.

Sarah Segal:
Yeah, you know, it’s interesting. I have to say that, as a former member of the media, I understand that you’re doing your job, but it seems like there’s this almost attack on San Francisco. I go to work in San Francisco three days a week. And there’s some homeless and there’s some, you know, whatever. But it’s no different than most cities I’ve been to.

I went to a hotel and restaurant conference the other day. I was talking to people, and they were like, “We have tourists coming here and talking to us and saying, ‘I don’t understand why everybody says that San Francisco is so terrible.’ They’re like, ‘It’s great.’ They’re like, ‘The issues in San Francisco are no worse than any other city, that it’s just for some reason the media has taken hold of this narrative and won’t let go.’”

Shawn Busse:
Yeah, my theory is that it’s transference. Essentially, what I think is happening, is anger at the tech sector, just in general across our society. And, essentially, San Francisco is emblematic of the tech sector. And I think there’s a lot of frustration with it. I think parents are frustrated with tech, because their kids are using these tools that are really unhealthy for them. I think businesses are frustrated with it. I mean, I can’t tell you how many software-as-a-service companies have raised their rates without adding any extra value to me in the last year or two. I just think most of America hates tech. I’m just gonna say it.

Loren Feldman:
Shawn, Portland has had some similar issues. Do you think it’s the same explanation there?

Shawn Busse:
I think it’s a different thing. I think the issue with Portland is that The New York Times had a love affair with our city for about five years.

Loren Feldman:
Kiss of death.

Shawn Busse:
Yeah, it is. I mean, they had a love affair with Seattle for a while. And then you see this news cycle—and I’m sure you’ve seen it, Loren. It’s the hero-to-villain news cycle, where whether it’s an entrepreneur or a business or a city, they’re beloved by the media until the tide turns. And then the media can find every reason it can to demonize them, because that gets clicks. I mean, at the end of the day, that gets clicks. And that’s what’s driving the news. Good news does not make money.

Loren Feldman:
Well, I would say—

Shawn Busse:
You’re gonna take it for the media, Loren. Sorry.

Loren Feldman:
I can take it.

Sarah Segal:
Loren, I came from a newsroom where it was like, “If it bleeds, it leads.” I mean, literally. That is an unfortunate truth.

Loren Feldman:
I just want to say, there’s a whole range of entities on the media landscape. And what you’re describing absolutely does exist. I will tell you, at The New York Times, I never had any pressure whatsoever about traffic.

Shawn Busse:
How long ago did you work there?

Loren Feldman:
I left about 10 years ago, but believe me, Buzzfeed existed 10 years ago.

Sarah Segal:
If you were to survey reporters, there’s a lot more pressure for them to create headlines and content that gets clicks. And plus, they’re burdened with the, “Okay, you have to write your article, but now you have to post it, and you have to do this and that.”

Loren Feldman:
It’s not so much that people want to have this hero-to-villain thing, I don’t think. They want something new. So if there have been lots of stories about somebody being a hero, and you come up with some evidence that suggests villain, you can fill a 14-inch story that makes that case. And it’s something different, and, yes, people will click on it.

Shawn Busse:
But I mean, I’m not saying there’s some grand conspiracy to go hero-to-villain. I just think that the natural cycle produces that outcome. Just like you said, how many hero stories about Portland will The New York Times run?

Loren Feldman:
It stops being news. You’ve got to do something different, if you’re going to write about Portland.

Sarah Segal:
What is the solution for San Francisco? That’s the big question.

Shawn Busse:
Well, you know what’s interesting, I think San Francisco and Portland suffer from the same problem, which is concentration of commercial real estate space without residential. So if you come to Portland, and you don’t drive into the core, urban area that’s entirely businesses, if you go outside of that—which is not very far, by the way. We’re talking like seven or eight blocks—it’s a totally different environment. It’s vibrant and tourists, and businesses are healthy, etc. So for Portland, it’s a very small area, but it’s very intense, where it’s located. And that, I think, is a function of the zoning.

Loren Feldman:
We’re just about out of time. I want to hit one more topic before I let you go, which is something that, Sarah, you referred to a couple of months ago, I think. I recently highlighted a story in the Morning Report about recruiting services who were interviewed saying that they do not recommend that employers hire former business owners, for a variety of reasons.

Shawn Busse:
We are unemployable, Sarah, so you better not let your business fall apart.

Loren Feldman:
And I’m curious, first of all, do you share that concern? Would you hesitate to hire someone who had previously owned a business, either of you?

Sarah Segal:
I wouldn’t hire me. [Laughter] Well, the reason why is, I constantly want to make things better and improve things. And if I’m working for somebody who doesn’t have that same vision—I definitely would not hire me. I think I’m stuck in my reality. Shawn, what do you think?

Shawn Busse:
You know, it’s funny. I was looking at your job history, Sarah, and my prediction before going over it was like, “I bet Sarah lasted an average of two years or less at most of her positions.” And I’m looking at your track record, it seems to hold fairly true. Would you agree with that?

Sarah Segal:
I would.

Shawn Busse:
Yeah, and same for me. I lasted two years at my last quote-unquote real job. And I think here’s the arc of what happens: You come in. You see lots of opportunity for change. If the business is reasonable, they embrace that, at first. And they’re like, “This is awesome. Sarah’s making all these cool improvements. Shawn’s making things so much better. Let’s promote him. Let’s give him more money. Let’s give her more money, etc.”

But then after a couple of years, or a year and a half or so, the business starts to be like, “Whoa, whoa, whoa, whoa, whoa, whoa. These changes you’re bringing are too big, too much, too much. We need to stick with the plan, stick with the system.” And that’s why you don’t last—you or me—for more than a couple of years. So I think the nuance of that article should be: You can hire former business owners if you’re okay with change, and knowing that they might only last a couple years. Because I think the amount of change they want to bring might be too much for most businesses. That’s, at least, been my experience.

Sarah Segal:
Yeah, I’m not a good just doer. I’m an improver. I want to make things better, and help a company do more things. And not every company shares that same vision. And quite frankly, I leave when I’m bored. My big thing with my team is: “I’m like you. I hope that you’re always learning something new.”

When I was a TV reporter, it was great, because I would literally learn something new every single day. One morning, they’d be like, “Oh, you’re going to do an economics story.” And the next day, “Oh, you’re gonna do a political story.” Because I was a general assignment reporter, I was happy to become an expert in the matter of four to five hours on whatever topic I was covering. And that was fun. And when you stop learning something at your job, that’s when you need to leave, because it’s not going to be beneficial for your career or your mental health.

Shawn Busse:
That two-year thing is something I look for when I’m looking at candidates. I look for the one-year-two-month, one-year-four-months, one-year-six months, because it’s like, “You know what? I think you should be a business owner.” Like, if I were to look at your profile, Sarah—like, I’m looking at it now—I never would have hired you. Like, never, no. [Laughter]

Sarah Segal:
Thanks, Shawn!

Shawn Busse:
I’m sorry. I mean, I would have been like, “No, she gets bored after a year or so. And she’s gonna move on.” And so I think there’s some truth to that article. You know, if you are building a business where you want people to be around for a while, business owners are not good—unless you’re gonna give them equity and make them a co-owner. I just see it over and over again. And like, somebody will announce, “I’ve decided to go out on my own.” And as soon as I look at their profile, it’s the same story every time: one-year-two-months, one-year-six-months, two-years-three-months. There’s a persona. I don’t know what it is.

Loren Feldman:
I have to say, I tended to last more than two years in most of the jobs that I had. I think four or five was more typical for me, but I also got fired by more of those than I can even keep track of I think. And I have to say, running 21 Hats, it’s not clear yet that it’s a real business. But I’ve gotten used to the idea of getting up every day and doing what I think I should be doing. And going back to following someone else’s marching orders—

Sarah Segal:
Oh my God. I would die.

Loren Feldman:
I would have a really tough time. I don’t know.

Sarah Segal:
There’s no reason to. Maybe I’m not gonna become the Edelmans of the world. But my full intention is building a larger, successful, midsize PR agency. And I know that I can do it. I like being the decision maker. And granted, I don’t make every decision. I trust my team about a lot of stuff.

One of my team members looked at me yesterday and was like, “Do you want to look at this press release about this really famous actor that we’re announcing for Fan Expo?” And I was like, “Did so-and-so on the team already look at it?” And she’s like, “Yeah.” I’m like, “Yeah, I don’t need to look at it then. You guys can make these decisions on your own.”

But in terms of the trajectory of the business, and kind of where we go, I like being at the reins. And I think I would suffer any other way. I will say—I did say the other day—I do want to put my resume together, which I haven’t done for, like, a decade. Because I’ve done some guest speaking at various universities and schools, and I coach a sport, and I really like working with young minds who are eager to learn and do stuff. And I could see myself teaching what I do at a collegiate level. So yeah, I could see myself having a boss in a different space, but not in my industry, because it would be miserable.

Loren Feldman:
Well, I think it’s a good sign that you feel that way, even after the rough stretch you’ve been through.

Sarah Segal:
It’s just rough. It’s a learning curve. You know, I learned something from it. I don’t think I did a terrible job. Nobody turned around and said, “I’m not going to take your payout.” And one of them is coming to a cocktail party that we’re going to this evening. We left on really good terms because they know it wasn’t personal. It was business.

Loren Feldman:
All right. My thanks to Shawn Busse and Sarah Segal, and to our sponsor the Great Game of Business, which helps businesses use an open-book management system to build healthier companies. You can learn more at greatgame.com. Thanks, everybody. Thanks for listening.