‘What Doesn’t Keep Me Up at Night?’

Introduction:

This week, we did something different. We recorded this session in Chicago at our very first 21 Hats in-person event. In May, some 20 impressive entrepreneurs from around the country, from different industries, with businesses of different sizes and stages, gathered to talk shop for three days. The last thing we did was to record this episode in which we gave the participants the opportunity to ask the podcast regulars anything they wanted. Those regulars included Jay Goltz, Sarah Segal, and Dana White, and the questions addressed everything from hiring to motivating to delegating to pricing to coping with stress to what they wished they’d figured out sooner and to what still keeps them up at night. And when there were no more questions, I asked those who attended the Chicago event what I could have done to make it better. That I would invite criticism in a conversation being recorded for a podcast audience, took some of the participants by surprise. But, as you’ll hear, it worked out pretty much the way I hoped.

— Loren Feldman

Guests:

Jay Goltz is CEO of The Goltz Group.

Dana White is founder and CEO of Paralee Boyd.

Sarah Segal is CEO of Segal Communications.

Producer:

Jess Thoubboron is founder of Blank Word.

Full Episode Transcript:

Loren Feldman:
This is just a great opportunity to get some feedback from some really smart people who’ve been hanging out with us this week. So I’d like to throw it open. Does anybody here have a question that they would like to ask anybody on the panel or all of the panel?

Nawal Motawi:
My name is Nawal Motawi. I’m the owner and founder of Motawi Tileworks, maker of very beautiful and distinctive art tiles. My question is for Jay, and it’s about hiring. So I’m always interested in learning new questions to ask of new hires. I’m trying to tease out whether these are kind, decent human beings. I’m looking for humble, hungry, and smart people for my company, and I’m interested to hear a question that you would ask someone, and what kind of answer you would look for or how you would interpret an answer.

Jay Goltz:
Well, we hire people everywhere from working in the factory to doing sales. So it’s different. But the first thing I want to know is, “Why are you looking for a job?” Because that can be very telling. “So are you still working?” That’s a big question. Are they still working? “Yes.” “Why do you want to leave?” “Well, it’s just time.” To which I go, “God, that sounds like bullshit. What do you mean, ‘It’s just time’? What does that mean?” And then I would ask them, “What do you like about where you’re at? And what don’t you like?” “Why are you looking?” I want to know: Why are they looking for a job?

And then given the internet and the websites, you can now say to them, “What do you know about my company that makes it seem like a good place for you to work?” I mean, they should have done a little research to go on and look at your website, for God’s sake. So I want to see if they have any good answers as to why they want to work here. And then I want to know: What are you looking for in a job? And that’s probably half the process.

The other half of the process is checking references, which from my experience, most people don’t do. Or they say they do, and they don’t, and you are just playing with fire. And it’s absolutely correct that nine out of 10 times, you’ll be wasting your time with a reference check. And that one time will save you a lot of grief. So good ad, great interview. I ask people who are in retail, “Tell me a difficult customer story that you had.” And that’s very telling.

Loren Feldman:
Does that answer your question, though, about finding kind people?

Jay Goltz:
That’s difficult. I don’t know how to tell if they’re kind.

Nawal Motawi:
I asked you a question earlier, and I liked your answer.

Jay Goltz:
Okay. What did I say?

Nawal Motawi:
I think the question you asked was: What did you think your previous boss could have done better?

Jay Goltz:
Right, tell me if you were in charge of the job you’re at or your previous job, what do you think they could be doing better? And I want to hear an answer. If they say, “Nothing.” Okay, they’re not being honest. There must be something. And then if they see there was a problem, I want to hear, “Oh, did you talk to your boss about it?” And I want to hear, “Yeah, actually, I did. I talked to him several times. I talked to their boss. And that’s why I’m looking for a job. Nothing changes.”

What I don’t want to hear is, I don’t want to see the rolling eyes. “They don’t listen to anybody.” I don’t want to hear that. I want to hear about somebody who was trying to participate, who was trying to make things better. Because, otherwise, they’re going to be complaining about you. I want people who are going to say to our face, “Hey, can we do something better here?” I want people to complain to our face. And you can tell from their last job frequently whether they’re the ones that are going to be the team player to say what’s on their mind, or they’re just gonna complain to everybody else?

Sarah Segal:
What do you think about references, though? You mentioned talking to references, and like, someone’s going to put forward their three favorite people who are gonna say wonderful things.

Jay Goltz:
Not true. Absolutely not true.

Dana White:
No, references with me are a waste of time. The three to four people they put on there are three to four people who tell the absolute best [things] every time. It’s very rare I’ve gotten a reference where someone said, “Yeah, no.”

Jay Goltz:
They’re not going to say no. It’s about what they don’t say. When I did the blog with Loren years ago, someone sent a great suggestion. He says: If you’re interviewing someone that the person is saying nothing but wonderful things about, and they quit, then he would say to them, “So it sounds like they were a great employee.” Pause. “What did you do to screw that up?” “Well, I didn’t say they were perfect.” And they’ll tell you the truth. I’ve had people tell me really bad stuff by just saying to them, “Well, they’re not working for you. So what went wrong there?”

What I’ve learned is, unless it’s their friend they just set you up with—and it was a setup, which you should be able to figure out—no one wants to lie for someone who was a terrible employee. I have never met a human being who is going to let the words come out of their mouth, “Oh, they were great,” when they were a nightmare. They won’t. Their brain won’t allow it to come out of their mouth. They’re gonna give you a long silence. I had one guy once tell me, “Well, I don’t want to elaborate.” Well, that was enough. Really? You don’t want to elaborate?

Sarah Segal:
I guess you have to be kind of specific with their kind of references. Like, “Please provide us a former manager.”

Jay Goltz:
And if it wasn’t the last job, if somebody hasn’t accumulated people they’ve worked with who can say something positive about them, there’s something wrong there. Now, if they’re right out of college, that’s a problem. There’s not much you can get for references. But if somebody has been working in the workplace, and they can’t find someone? What do I want to hear in the reference? “Oh, she’s great. You should hire her.” That’s what I want to hear.

Jim Kalb:
Jim Kalb, Triad Components Group. Good to see you all. So you all come from very diverse backgrounds and industries. I want to know what keeps you up at night? And what are you afraid of after the time you’ve been in your business?

Sarah Segal:
Ooh, that’s a good question. Don’t come to me first.

Jay Goltz:
You know that phrase—what keeps you up at night?—sometimes I get up thinking about stuff I have no control over. And it has nothing to do with business. So what am I worried about in the business? Not a whole lot. I mean, if a key employee left, that’d be a problem. But does it keep me up at night? What I’ve learned over the years is: Stop worrying about stuff that you can’t control. I’m trying to choose not to worry about stuff. Does my subconscious do it? Sometimes. Yes. But at the moment, there’s nothing business-wise that’s making me [worry].

Loren Feldman:
What If he asked you this question 20 years ago? What would your answer have been?

Jay Goltz:
Oh, I had constant cash flow problems, employee problems. I keep telling everyone: I’ve been doing this for 45 years, I’ve gotten better at it. It didn’t happen in 10 years. This did not happen in 10 years. Twenty years ago, I was stressed out to the max, and—I take it back. About 20 years ago, I started to get it under control. So I’ll rephrase the question for you. I would say,
“What changed me from completely being stressed out to not?” Hiring and firing, hiring and firing, hiring and firing.

Loren Feldman:
Dana?

Dana White:
For me, it’s growth and making sure I don’t make the same mistakes that have hurt me, you know, personally—not personally, but emotionally—and hurt my business. Fear of the unknown, right? Because I am 10 years in. So it’s cash flow, do we have enough money? We’re going so slow. Why are we going slow? What didn’t I do? Am I repeating the same mistakes? That keeps me up at night.

Loren Feldman:
Sarah?

Sarah Segal:
What doesn’t keep me up at night? [Laughter] Every aspect of my business keeps me up at night. I make lists, and I have to have a pad of paper and pen next to my bed, because if I don’t write it down—I think it’s a thing in my family where we solve the world’s problems as we’re trying to sleep at the same time. And the only way to get it off of my brain is if I put it down on a piece of paper.

So, I don’t worry too much about making payroll anymore, because we’re profitable. But I worry about making sure that our clients are successful and happy. I worry about whether my staff is being successful and happy and flourishing and being challenged and being given new opportunities so they want to stay with us and want to grow with us.

And then I definitely worry about the growth of the business. Where should I put my money and my time so I can make sure that we’re growing in such a way that is sustainable and good for us in the long-term? Because I don’t want to start doing something that is not going to be sustainable for us and is not going to be something that we can repeat for other clients.

Loren Feldman:
Another question? Kemi?

Kemi Tignor:
My name is Kemi Tignor, and I’m the founder of Upbounders. We make screen-free puzzles and toys, with decidedly diverse imagery. I’m earlier on in our startup journey than you all are. So I’m making a lot of decisions, and I’m having those sort of first-employee, first-contractor engagements. And I wondered, as you were building your teams, what were the first positions that you began to fill?

Dana White:
I couldn’t grow my business without a team. I was one woman—and I’m not a hairstylist—so during buildout, I opened. So my first positions were stylist and shampoo assistant. Similarly to you, two or three years in, I replaced myself, if you will, in the administrative capacity. So it was now, bring on a manager, bring on an assistant manager and a receptionist.

Jay Goltz:
I was 22 years old when I started. I hired people who were younger. I hired kids. They were out of high school, and we’re doing framing. And it evolved over the years. How long was it before I hired a grown-up who was taking responsibility? Probably six years into it at that point. But I started at zero. Different businesses need different skill-sets.

I will tell you the worst advice someone gave me. I was having a real bad day at the front counter. And this older guy said to me, “Jay, the bigger you get, the harder it gets.” Absolutely not true. My life is—no comparison—easier now than it was 20 years ago. So I want to tell everybody who’s struggling: Keep working at it. You’ll figure it out, and it gets easier. That should be the message. It gets easier, not harder, because you can figure this out. It’s complicated. There’s a lot of working parts. Don’t think you’re going to figure this out in five years.

Loren Feldman:
Sarah?

Sarah Segal:
My first hire was to find somebody who could do the things that I shouldn’t be doing anymore, the things that I knew that I could train somebody else to do with competence. So for PR, that’s building media lists, pitching out to reporters, getting feedback, doing follow-up. It’s like, what I do for a living, the general PR, it’s not brain surgery. It just takes a person who’s organized, who can understand the nuances of how a newsroom works and what reporters are looking for, and be following trends, and really be able to communicate well with the clients. And so my first person—and actually, my first several people—are always people that can do something that takes something off my plate.

Jay Goltz:
You know, you use that phrase, “it’s not brain surgery,” but it’s not scooping ice cream, either. It’s somewhere in between. So most jobs take some kind of skill-set.

Sarah Segal:
But I think that’s important, to hire people to do things that, yeah, you know how to do them, and you could probably do them really well. But should you be doing them? And I think that’s something that you’ve talked a lot about as well.

Jay Goltz:
They always say, “Oh, you’ve got to delegate.” No, before you can delegate, you have to have a competent employee to delegate to, because delegating to an incompetent employee is not a good thing. And that’s the part they leave out.

Dana White:
It’s double work.

Steve Krull:
Steve Krull, CEO of Befoundonline, a digital marketing agency here in Chicago. There’s always this idea as people are starting out, and I’m sure a lot of your listeners, Loren, are new to business. We’ve got some folks in the room here who’ve only been at this a year or two. Looking back—and you’ve each had careers of varying lengths—what do you tell your former self? Jay, what do you tell your 22-year-old self when you started this? What advice would you give them now after everything you’ve been through, looking back?

Jay Goltz:
There’s no question there are two things that I just messed up for many, many, many years. Don’t be naive with hiring. If you’re looking for really good people, only one out of 10 is going to be a real good hire. So don’t just interview people, “Oh, they’re nice,” and hire them, because they’re probably not going to work out. So I went through a horrible learning curve with that.

And the second one is—and this isn’t just me, this is general to most entrepreneurs—I was giving tremendous service and tremendous product, and I wasn’t charging enough. I said this out loud: “Listen, price, quality, service. Most people want to give two out of three. I’m gonna give all three.” Stupid! You can’t give all three. It is impossible to give all three, because if you’re giving the best service and the best product, you’re gonna have to have better people and you have to buy the better stuff. It’s gonna cost more. So you’ve got to pick the two out of three. And I think if you’re a small business owner, it’s easier to give quality and service than it is to try to give price. Because unless you’re Walmart, I don’t know how you’re going to buy cheaper or something to pass along the savings. So that haunted me for many, many, many, many years. You need to charge what you need to charge.

Dana White:
I would have gone back and told her, “You’re smarter than you realize. Stop giving everybody the microphone as if you don’t already know. And raise your prices. [Laughter] Raise your prices.”

Sarah Segal:
So I agree: Raise your prices. Know your value. Because even though what I do is not brain surgery, people can’t do what I do. And I know that they can’t do what I do, because they don’t have the 10,000 hours of having been a reporter, more than 10,000 hours of being a publicist. They don’t have my background and ability to dive into different industries like I do. I can talk metaverse one moment, and talk donuts the next moment. And not everybody has the ability to do that.

I’d tell my younger self: Although we’ve only been around for five years, trust your gut. Because I’ve made some hiring mistakes where I was like, “Well, everybody likes the person. They seem very competent”—and I didn’t trust my gut. Or a potential client where I got the feeling that they just didn’t understand the value of PR. And I was like, “But you know what? They’re such a great company, and they have such a great product.” But we spent so much time explaining the value of what we did, it took into the hours that we should have been working on them as a client. And then the last thing would be: Keep with the idea that just because it was done a certain way in the industry forever doesn’t mean you have to do it that same way.

For example, when I was working at other agencies, there was a really crazy formality in terms of how you address your clients. And every email that you sent had to be very structured and professional. And I was like, “That’s such a waste of time. I don’t want my team spending 15 minutes curating out a fancy email when you’re just trying to get some point across.” So we integrated Slack. Now we have a Slack channel with all of our clients. We are constantly communicating, and sometimes it’s funny. Sometimes it’s short. Sometimes it’s straight to the point. But it makes us so much more efficient in what we do. And you don’t have to do it the way that everybody else has done to be successful.

Jay Goltz:
I’ll tell you what I didn’t do wrong. I have always, from day one, had unwavering support to make sure the customer is taken care of every single time. And that’s why I’ve survived all of the bad stuff that I did: the wrong hiring, the cash-flow problems, pricing problems, whatever. I’ve survived that all because I have always taken care of the customer. And at the end of the day, if you look at my growth chart compared to somebody else, it’s just about being a little bit better. Just a little bit better. If everyone else is retaining 90 percent of the customers, and you retain 95, it’s—

Loren Feldman:
Over 40 years.

Jay Goltz:
Over 40 years, it’s the difference between being a multimillion-dollar business or a $200,000 business. It’s just being a little bit better. It’s not about being a lot better.

Kemi Tignor:
This is Kemi again of Upbounders. So social media, podcast advertising, is everything niche? Or are there still ways to reach the mass market, such that it still exists?

Loren Feldman:
Can we all agree that podcast advertising is the most promising of those options? [Laughter]

Sarah Segal:
I think if you want to reach younger audiences, podcast advertising is absolutely where you should spend your money. You talk to anybody who’s under 40 what radio station they listen to, and they’re going to look at you cross-eyed. I mean, I listen to news radio like it’s going out of style. And my children are forced to listen to it, because that’s what I listen to. But they don’t listen to radio at all. And television—

Jay Goltz:
Nobody under 40 listens to radio?

Sarah Segal:
It’s pretty light.

Jay Goltz:
A lot. So let’s get off nobody, to less people.

Sarah Segal:
They listen for the weather, and they listen for their traffic, and that’s about it. But podcasts? Podcasts are what they listen to. They don’t watch television anymore. It’s all about streaming. It’s being able to have the program that they want on demand.

So, yeah, I think podcasts are a fantastic place to invest your money, but depending on your demographic, who you’re going for. Because if my client says, “We really want to reach out to people who are 25 and under,” we’re gonna be like, “All right, TikTok. TikTok’s what you gotta do.” You’ve gotta talk to influencers. We’ve got to get some content going out there, and you have to look at the medium and figure out who’s watching or listening or reading that medium, and figure out whether it matches your target audience. And that’s where you invest your money.

Chris Campbell:
This is Chris Campbell with Ritzr. You know, we’ve talked a lot these last few days here in Chicago about business, but I’m kind of curious—mostly because I find most entrepreneurs match the office and the home life in terms of the same level of intensity—whatever the hobbies or passions might be.

Jay Goltz:
I’m relaxed all day long, so I don’t have to go home and relax. [Laughter] I mean it. I’m in business groups. I said to them at the last meeting, I looked around the room and I go, “Does everyone realize that every single month we have meetings, every single one of you talks about how stressed out you are, and I’m not? Have you seen the difference?” And I’m trying to make a point to them that there’s something wrong there. I just don’t think you have to be stressed out all day long in business. I think if you hire the right people, it will get easier.

So I’m relaxed at work. What do I do? I don’t play cards. I love my family, married 43 years. I love being with my grandchildren. But somebody said to me, “Hey, you need a hobby.” And I laughed. I go, “Really? My life is my hobby. My business is my hobby. I don’t need a hobby.” So I don’t have a great answer for that. And I don’t play pickleball, though everyone else I know seems to be playing pickleball.

Dana White:
I’m a reader. I’m a cross-stitcher. I love a good movie.

Jay Goltz:
Oh, I love movies, too. I left that out.

Dana White:
Yeah, I love a good movie. I live in a great community. So I spend time in that community, walking. But I’m constantly—that’s my problem—my business lives with me. It is my third parent, and my first child.

Jay Goltz:
Is that a problem? That’s the question. Is that a problem?

Dana White:
It can be a problem if you’re worrying about things you can’t control, but I’m learning over time: “Okay, this is not productive.” I haven’t had a vacation in years. Haven’t had a vacation. Because it’s like, now’s not a good time. Now’s not a good time. Now it’s not a good time. But in COVID, I was like, “Oh my god, this is the worst thing that could possibly happen,” but it actually was a blessing.

Loren Feldman:
Because?

Dana White:
It required that you take pause, step back, look at your business, assess, and move it differently. And it gave you the time and space to do it. So I’ve carved out time to take care of Dana. I’ve learned about spas. What is that?!!! Like, it is amazing. So I’ve gone to a spa, and that’s gonna be a part of my self care.

Loren Feldman:
There you go, Jay.

Jay Goltz:
I like going to spas.

Dana White:
You go to spas? [Laughter]

Jay Goltz:
Not a lot but occasionally, sure.

Dana White:
Are you kidding me?

Jay Goltz:
Why would I kid?

Dana White:
I never knew that. Jay Goltz!

Jay Goltz:
Every couple of years, maybe.

Loren Feldman:
Sarah?

Sarah Segal:
So I’m a bit of a joiner. I’m on a couple boards. boards that are in my industry. And I do a bunch of events, so like, I’ll organize tours of local TV stations and radio stations and stuff. And we’ll do cocktails and stuff, and just getting to know people in my industry who happen to live in my area. And then I coach cheerleading.

So I did cheerleading when I was younger. I see cheerleading as a valuable way to teach people confidence in public speaking, being in front of an audience, having an ease at being the center of attention. Because, while I can do television—put me on NBC, the Today show, no problem. But putting me in front of a live studio audience is a little stressful for me.

But it’s amazing the confidence they get from day one to the end of the season. And I always love telling people how many really well-known people were cheerleaders. Ronald Reagan was a cheerleader. Ruth Bader Ginsburg was a cheerleader. Sandra Bullock was a cheerleader. There is a long list—especially past presidents—that were cheerleaders.

Loren Feldman:
Next question.

Nile Livingston:
Hi, my name is Nile Livingston, and I’m the founder of Creative Repute, which is a graphic design website development and mobile app agency. My question is, speaking of business needs, have you ever made and implemented a plan to help grow your business, such as hiring more sales team members, training, or increasing your total addressable market by moving to a new location? I’m curious what growth plan did you implement, or do you want to implement?

Dana White:
Yes! [Laughter]

Loren Feldman:
All of the above?

Dana White:
All of the above. Great question. As many of you know, I moved from two locations in Detroit, Michigan, to one and a half locations in Dallas, Texas. I think, Nile, you asked me yesterday, “Did you know anybody?” I know nobody in Texas. I have no family in Texas. But I knew that the market was ripe for it. And so the business plan changed, because I was going to a different market. We were walk-in only. Now—and temporarily—we are by-appointment only. Why? Because I didn’t want to jar the market with not only are we an evolved form of haircare, not only is our business model already kind of different, but now you’re walk-in only. And I wasn’t sure that walk-in only would compute.

So, like in Michigan, it really didn’t. We had people who would show up at the salon at two o’clock in the morning and call and leave a voice message, “Why aren’t you open? Because I heard walk-in only and thought 24/7.” And that’s not what it was. And so the business model had to change, as far as how we service. We are going to go to walk-in only. We’re gonna go back, but just to get our feet wet, we’re going to do salon by-appointment.

In other ways, we changed the business model, I’ve added more services. I’ve been confident in saying, “Okay, when we’re talking about getting new ideas, what did my customers need that I didn’t give them in Detroit?” The other big thing is marketing, marketing, marketing, marketing. I said at dinner last night: I’m afraid I’m about to make the same mistakes in Dallas, Texas, where it doesn’t matter how ripe the market is if I’m not telling anybody, right? The young ladies who moved me out—there’s a moving company, most of the movers were women in Michigan—they walked in, they were like, “Oh my God, this place is beautiful. How come I’ve never heard of you?”

Loren Feldman:
Jay, did you ever have a growth plan? Or do you just show up every day and keep going?

Jay Goltz:
No, I’ve opened stores. I’ve hired salespeople. Sometimes it works, sometimes it doesn’t work. It usually works. I’ve got four successful businesses, but I’ve started eight businesses. And some of them crashed and burned pretty quick. And some of them, I held on to too long and lost hundreds of thousands of dollars. So like, it goes with the territory. Yeah, I opened a pop-up in New York, did some nice business there. But the rent was so… I tried it. I will not be the guy on his deathbed with regret saying, “Oh, I wish I would have tried that.” I’ve tried a lot of stuff. And I’m still standing, and I feel good about that.

Loren Feldman:
Nile, is there a growth strategy or plan that you’re considering, that you’re wondering about?

Nile Livingston:
Yeah, I just took a business boot camp for the first time and did a pitch for the first time as well. And something that I’m considering is focusing on sales and marketing, by maybe opening up another virtual office in another city so that I can increase the client base—and making sure I have feet on the ground, hiring more sales team members in that particular location.

Dana White:
I say, do it, but make sure you’re going to an area—I wouldn’t go across the country. You’re in Philly. I might go to another part of Pennsylvania.

Nile Livingston:
Maybe in New York, where the cost of living is higher, so I can charge more.

Dana White:
I wouldn’t charge more because the cost of living is higher. I would charge more because, what service are you providing in New York that might cost a little more? I always tie my pricing to what we’re putting out, not necessarily the needs of—

Jay Goltz:
Have you run out of customers? I mean, Philadelphia is a big city. Or do you have a specialty that is better to be leveraged in different cities? So why would you leave Philly?

Nile Livingston:
Yeah, not only am I a business owner, but I’m a visual artist in Philadelphia. And so I was born and raised. I have a really strong sense of community, and it’s very supportive. But I do feel as though I’m only known as a local artist. And with the business, I do feel like I know every single nonprofit in the city, and I’ve worked with them at some point. So I do just want to see what it is like to expand.

Jay Goltz:
Okay, so that makes sense. You’ve run out of the nonprofits that you think is your best niche. You’ve run out of them. Okay, that makes sense.

Loren Feldman:
Any other questions?

Jennifer Kerhin:
Hi, this is Jennifer Kerhin. I’m the CEO of SB Expos and Events, an association convention management company. So yesterday, we spent some time asking each other questions. And one of the first questions was: How big do you want to be? And after two days here, I think the better question that I’d like to ask you is to imagine a future where you are not stressed—as Jay was talking about that he’s not now—where even though you’re wearing the 21 different hats, that they’re not feeling overwhelming, that they’re not pressing down on your skull, right? What does that look like to you guys? What does that future look like?

Dana White:
The future, for me, is we are in all major markets. I have a few company stores. I have a few franchises. I have products that are being sold profitably, and I have sold the military-base company that I have. I think a non-stressful day as the CEO and owner of Paralee Boyd is Dana, 20 hours or less a week, with just a great group of people that are on this mission with me—similarly to Jay—who believe that we can change how women of color look at their hair care. They can go jump in a pool because there’s a Paralee Boyd over there. They can live a different life, because their hair doesn’t dictate where I go vacation, where I go to college, where it’s not on their list of things to do. There’s a freedom that they’re all interested in continuing and implementing through this company.

And working with that group of people, things just get done. Ideas can be implemented, and they’re executed. They come back to me. “You love it?” “Yep. Let’s go.” So it’s focusing on executing the vision, as opposed to, “Oh my god, did we meet payroll?” “Oh my God, did we have enough money?” That’s it. It used to be 250-plus locations. It’s not that anymore. It’s all major markets opening up to franchising, if you find the right people. People are at the center, and that’s what would make me stress less.

Loren Feldman:
Sarah, can you envision that future, stress-free?

Sarah Segal:
I mean, I’ve stressed, but I think I always have stress. It is just part of being the person responsible for the livelihoods of your staff. I had an intern ask me, “What’s your five-year and 10-year plan?” I’m like, “I would love to say that I have one that’s definitive, but I would like to continue to grow at a good pace.” Someday, it might be nice to open a second office in another major metropolitan city, preferably somewhere where I would want to be for a while. I’d love to have that kind of West Coast-East Coast thing. I mean, I’m from Boston. It’d be awesome to go back and establish there as well.

But I would love to get big enough, where we have divisions that are really robust, where we have our technology division, we have a consumer goods division that’s broken down by food, wine, CPG brands, and really be able to have separate practices within the company that can be very dialed into those specific industries—so going from a generalist agency to an agency that has focused groups that really know each of those industries would be kind of my goal, I guess.

Jay Goltz:
I think the key is the 21 hats. You have four staff members who are very competent. Each take three or four of them. So now you’re left with five of them. That’s how it works.

Loren Feldman:
I’m not sure that math works, but… [Laughter]

Jay Goltz:
It does work. You’ve got four people who each take three or five things, so they each have five things. So that takes care of… You don’t have to get rid of all of them. If they took care of three of them that would lighten the load because a lot of the 21 Hats are like things you’ll deal with occasionally. Real Estate. It’s not like you do it every day.

Loren Feldman:
Another question?

Chris Campbell:
Yeah, this is Chris with Ritzr again. So we talked a little about motivation. You’re talking about staff and how important it is to have key people. And in the room earlier today we were talking about, it’s more than just money. I’m kind of curious what kind of creative motivators have you done, where you’ve gotten exceptional results from your team? And Jay has these playing cards. And he goes, “There’s maybe 10 ways to motivate people and 100 ways to demotivate them.” And I’d just be curious to hear a few examples.

Jay Goltz:
I get that question, “Oh, how do you motivate people?” And I’ve learned, that’s not the problem. The problem is when you interview people looking for jobs, you hear about all the ways to demotivate people. I think if you treat people nicely and respectfully, and they join the mission… I don’t have any motivational thing in my head that I said, “Oh, boy, this got everybody on fire when I told him this. I gave him a boat.” I don’t do that stuff.

I can think of a lot of ways—one little comment, one stupid thing you do to really, really turn somebody off. And my average employee has been here 11 years. I’ve got many people who have been here over 20 because they own their jobs, and we all work together. So I would suggest everyone stop thinking about ways of motivating people and start thinking about ways that you might be demotivating them, because some of them aren’t going to tell you the truth when they leave. They’re just gonna leave.

And I think a well-oiled company with people that are on the mission with you is very different. This is where the world’s coming to our side. Many of the Millennials want to work at companies with a soul where they can join a mission and feel good about it. They don’t want to go to work at the big corporation where you spend three quarters of your time playing politics and making yourself look good, figuring out who to talk to. I have never worked at a big corporation. All I know is talking to people who I’ve interviewed, when I hear about some of the machinations they go through, working in the place—stuff that’s broken, they can’t get fixed. Will so-and-so get the bonus based upon this? It’s dysfunctional, crazy stuff that a smaller company doesn’t have to be. They could just be mission-driven together. So I think it’s about being mission-driven.

Sarah Segal:
I believe in kudos, making sure that you’re telling your team when they’re doing a good job, or they’ve had an accomplishment, immediately, whether or not it’s over Slack, and to the entire team channel saying, “Rockstar Emily landed a placement for a client. Good job, Emily!” I mean, we’ve all had those situations where you’ve walked into a store, and then the salesperson is like, “Oh, I love your shoes,” and I’m the crappy shoes—but for that moment, I’m like, “Great shoes!” And it’s those random acts of kindness that I think keep people motivated. It just gives you a little burst of something.

We actually have an awesome app—I’m gonna plug somebody’s app—it’s called Thnks, T-H-N-K-S. And everybody on staff has access to it and can send somebody like a gift card to a Starbucks or whatever within a certain range. It’s just like a really good job well done. You went above and beyond what you were expected to do. And you did a really great job. And I’m thinking about you. And it’s a nice way for them to do that.

Dana White:
I’m old-school. So we have a kudos box in the salon. We have pieces of paper. And you write a note to your colleague, saying, “Great job with that customer, she was really giving you a hard time.” We fold it up, put it in the box. And the next time that person works, the manager goes in, sees whose names are on for the morning meeting. And she reads them out loud at the morning meeting. And then she gives them to her. That is huge.

Sarah Segal:
I was listening to a story the other day about an elementary school teacher who asked everybody in the class to write down one word about everybody in the classroom. And put those on a piece of paper for each of the kids, and there are people who have those pieces of paper with the descriptor, and they keep them in their wallet. And it’s just these great positive reminders. Because I never know how I come across to other people.

Jay Goltz:
Great. You come across great.

Sarah Segal:
Thanks!

Dana White:
We also have PB bucks. So it’s up to the manager’s discretion. There’s metal Paralee Boyd dollars with the logo on it or different branding things. And in addition to the kudos, she’s handing out PB bucks. And you get so many, and you can get a $250 spa package all the way down to a gas card. And what’s on that board for gifts is dictated by the staff. So it could be, “There’s a good concert coming up, could you get us tickets?” And then two tickets are up there, or placeholders for tickets. So those are how we move with it. Kudos are pieces of paper in a box. And when I tell you that builds camaraderie, they love it. There’s been tears.

Jay Goltz:
I take it back. There’s something we do at the factory. You all were in the cafeteria. Did you notice the Rocky statue in the corner? Once a month, we have the Rocky Award, which of course, most of the people who work for me weren’t born when Rocky came out, because that was 1976, I think. But we do the Rocky award, the employee of the month, and they read out who was nominated and why. And then we turn on bom, bom, b-bom, b-bom—you know, the music—and they come up and they take a picture, and we have a good time with that. And we certainly do some small things like that.

Sarah Segal:
It’s not just about employees as well. It’s about customers. I don’t know if you’ve ever heard of lagniappe. It’s, I believe, a Creole word for an unexpected delight. So I believe it’s the Doubletree hotels where you walk in the lobby, and they give you cookies. Even when you go buy shoes, have you ever had the salesperson bring out three other pairs that you might like, because you picked that one pair? It’s those unexpected delights, and I think they work.

Jay Goltz:
You know who doesn’t get those days? The boss.

Sarah Segal:
Oh, no, the boss. I’ve never gotten kudos, and I’m okay with that. And reporters don’t get them, either. And that’s my big thing. If you’re ever working with a reporter, and they write you a really great article, and you put it on Twitter, or you find it and you reshare it on Twitter, all of those algorithms will tag the news station, the news outlet, but they won’t tag the actual reporter. So you have to do the next step. And tagging the reporter and saying, “Thanks, it was awesome talking to you. Great article.” Because reporters, they churn them out and churn them out. But nobody says thank you.

Loren Feldman:
We’ve spent the last couple of days spending a lot of time with each other. We’ve had some good meals, some good walks, we took a boat ride. We’ve been in this conference room where we’ve been kicking around big-picture ideas. This is the first time I’ve done anything like this. And I’m just curious if you could offer me any suggestions. What could be done better? What would have made this a better experience? Anybody care to respond to that?

Sarah Segal:
I will.

Loren Feldman:
Please, Sarah.

Sarah Segal:
Name tags!

Jay Goltz:
I brought that up.

Sarah Segal:
I always love to have a takeaway. I mean, I love Jay’s playing cards. They’re fantastic. But a takeaway of something I’m gonna implement in my business to make it better. And I know that’s really hard, because it’s really dependent on what kind of business you have, but give me a cheat sheet or something that will help me think along the day. There are so many conversations that I’ve had over the last two days, that even a workbook where it forces me to make some decisions or action items that I’m going to do when I get back.

Loren Feldman:
Who else has a suggestion?

Tricia Groff:
Hi, I’m Dr. Tricia Groff of Psychology builds business. I currently do consulting with CEOs and business owners to mitigate risk and help make sure that they reach the opportunity in front of them. And then I’m looking at building two scalable businesses related to informational products and tangible products.

I personally believe that it’s inside of us each to figure out how we’re going to maximize the situation, what we’re going to get out of it. And so I’ve been fighting like crazy, because my consulting business is dialed in. I love it. I love what I do. And I’m looking at this horizon in front of me of where I’m going without a plan. Without like, what do my profit margins look like? With so many questions in my head. We went through a discussion yesterday about revenue, profit, and we ran out of time right before lunch. And running out of time right before lunch, when I was going to actually ask the whole group to make me cry, because I needed questions. I needed people to drill me.

So I went to lunch. I was completely frustrated, because I was holding all of this angst in my head, and there was nowhere for it to go. What I know about myself is that when I’m pushed to that part, it’s right before a breakthrough. It’s right before something really clicks in. So I had to sit with it. And I knew that we had tapped into something hard, in terms of the barriers that are holding me back. So I sat with it. I sat with it. I listened. And throughout the evening, and this morning, the Aha! moments came because you had space. Like at breakfast, there was space for us to talk to each other. And in that space, I was both able to process and get feedback. And so for me, that was game-changing. And I think what I’m trying to say is that sometimes the answer isn’t having a perfect plan. It’s allowing enough mess in the process for people to figure out their way.

Jim Kalb:
Jim Kalb again. What I really appreciated was there was plenty of white space to operate. You didn’t have everything so programmed out as to what we’re going to do. It was a really, really wonderful time here. So that’s what I took away from this.

Steve Krull:
I’ll throw a takeaway on top of that, Jim. Steve Krull, again. My takeaway is the size of the group. It allowed us an opportunity to get to know everybody in the room—about 20 people—without going, “Oh, I haven’t been over there, over there, over there.” Where at a lot of the larger events, you sort of get stuck, and you’re lucky if you get to know somebody. And luckier still if you get to know one or two people. I think I’ve walked away with half a dozen good friends, and I’ve gotten to know everybody at least a little bit in the room.

Jennifer Kerhin:
For my takeaway, this is Jennifer Kerhin again, I would say the reason I listen to the podcast is the authenticity and the rawness of the anecdotal stories. I can read a lot of business books, and I do. But that emotion, that rawness, authenticity doesn’t come out in a business book, right? And so I think my takeaway from this last couple of days is with this group size, with the sharing that went through, with the breakthroughs, with the Aha! moments, it was the sharing and rawness of our group.

Dana White:
So hearing me cry on the podcast was okay?

Jennifer Kerhin:
Well, yeah, because I have to say, I remember. Dana, I can’t tell you how many times I’ve listened to your story, and turned off the podcast and be like, “Oh, I feel her. I feel her.” I had no idea where you were at the moment. It could have been thousands of miles away. But you made me feel not alone.

Dana White:
Oh, wow. I’d get off the podcast and go, “What the fuck?” I’d get off and I’m like, “What did I just do?” And he’s my barometer: “Loren, was that, okay? Because I’m not really feeling comfortable with it.” And he’s like, “Nope, I got you. I trust you.” You’re like, “You’re good.” Okay. So that’s why I was actually making a joke—so it is okay that I cry. You answered it honestly. You’re like, “Oh, no, it’s really good that you do.”

Jennifer Kerhin:
It’s good. At business conferences, you’re listening to professional speakers speak. They’re not crying. And yet, they’re also not worried about payroll. They’re not worried about their employee, who you forgot to do it after five o’clock on Thursday, and ADP won’t run payroll. So now people aren’t gonna get paid until Monday morning. And now people are scared they’re not gonna pay their mortgage. Those professional speakers aren’t thinking about that. You are. And I hear you. So thank you for sharing.

Sarah Segal:
I want to hear where people messed up so I don’t do that. I want to hear mistakes that you made so I don’t make them too. And to do that for other people, I try to be an open book about where I went wrong and where I’ve made mistakes. And I think that those experiences are what help other people. Because I’ve certainly made mistakes, bad judgment calls, nothing Earth-shattering, but at the time, it eats you up. But I think having that level of candor is only going to come back to you in a positive way.

Loren Feldman:
We’re going to have to wrap up. Anybody else with a suggestion of something that worked or didn’t work, that we could do better? Kemi?

Kemi Tignor:
This is Kemi here with Upbounders. I was just going to say, for anybody listening who is in sort of the early startup phase, as we are, what I found to be great about this experience is that I didn’t feel like I was wasting any time, for lack of a better word. I hardly do anything else, except work on the business. And so if I’m going to be here, I want to make sure it’s constructive, and it was 157-percent constructive.

And we sort of sell product to other retailers. So I had a chance to see some other sort of retail partners here in Chicago. But just every minute of every second, I haven’t worried about the business because I knew that these were constructive conversations, constructive observations of other entrepreneurs, their authenticity. So that was really great. I’m going to send out a press release with Sarah’s help.

Sarah Segal:
I think it’s awesome. I think what you’re doing is amazing, and you have a good story and a good hook. I think every business has a good story and a good hook, but the people who are running the businesses don’t necessarily see them. So sometimes it is valuable to have an outside party come in and ask those questions. Because they’ll see you differently. But that’s awesome.

Loren Feldman:
Tricia, you had a question.

Tricia Groff:
Yeah. So, okay. I’m not debating, and I want to be supportive of your strategy. But I was so confused. What’s your strategy in asking us to tell the audience what we didn’t like?

Loren Feldman:
The whole 21 Hats brand is predicated on the idea that we have real, raw conversations, that we talk about things that other people, other business owners, don’t always hear discussed. As you all know, I often give Jay a hard time. I ask him lots of questions about why he’s got too much inventory, or why he doesn’t spend more time figuring out digital marketing. And I feel it’s incumbent upon me to be open and willing to have a difficult conversation about what I’m trying to do as well. So it starts with that.

But also, it has something to do with the fact that I know each and every one of you now, having spent the last couple of days with you. And I knew if I asked you, “What could I do better?” there was a good chance you would also tell me what you did like and what you got out of it. And that did happen. But I wanted it to be a real conversation. If I just said, “Hey, tell me how great a time this was, wasn’t this wonderful?” it wouldn’t have been real. But if I asked, “Give me some constructive criticism,” then maybe it will be meaningful.

Tricia Groff:
But here’s the thing, the positive stuff that works is as important as what doesn’t work, because how can you replicate it if you don’t know what worked?

Loren Feldman:
But I knew I would get that too. And if I just asked for that, it wouldn’t be as meaningful.

Sarah Segal:
Loren is an entrepreneur. He spent a career as a journalist and an editor, and you know, this is a new foray for him. So I think having this is just as beneficial to you, as a business owner, as to the rest of us. You may be moderating and hosting the event, but you’re also learning how to do things better for your own business as well. And so, for us, giving him candid feedback is only going to help him improve and make the next one, which I entirely look forward to—you know, if you want to do it in California, we could make that arrangement…

Jay Goltz:
It’s gonna have 1,100 people at it. [Laughter]

Sarah Segal:
I know a fantastic vineyard with a great space.

Loren Feldman:
Ooh. There are a lot of heads nodding right now.

Jay Goltz:
Taylor Swift is going to be entertaining at the next one. Just saying.

Loren Feldman:
All right, well, I want to thank the podcast regulars who are here: Dana Jay, and Sarah. And I especially want to thank all of you who attended this event and participated in this conversation. I know I got a lot out of this. Thank you all, and thanks also to our sponsor, the Great Game of Business.