Can I Go Dig a Hole?

Introduction:

This week, Liz Picarazzi, Jennifer Kerhin, and Sarah Segal talk about whether they ever wish they could go back to their corporate lives. For Liz, there was a period during the early days of COVID. For Jennifer, it was when she made the transition from a consulting business to an employee business. These days, none of them can imagine going back—although Sarah did have a rough week recently when she lost two clients. “It’s just the way of the world,” she tells us. “When businesses are looking to cut costs, it’s outside agencies that go first. But when it’s two of your largest clients in the span of a week, it’s like, ‘Really? Can I go dig a hole, put myself in it, and just stay there forever?’” What she’s actually doing, as we discuss, is figuring out some new ways to attract more clients. We also discuss whether everyone needs a business plan and whether the three owners ever wonder if someone else would do a better job running their businesses.

— Loren Feldman

Guests:

Jennifer Kerhin is CEO of SB Expos and Events.

Liz Picarazzi is CEO of Citibin.

Sarah Segal is CEO of Segal Communications.

Producer:

Jess Thoubboron is founder of Blank Word.

Full Episode Transcript:

Loren Feldman:
Welcome, Jennifer, Liz, Sarah. It’s great to have you all here. The three of you have much in common, including the fact that you’ve all been very generous about sharing the ups and downs of your journeys here on this podcast—which leads me to the question I’d like to start with today. None of you had to start a business. And I’m just curious, especially when you’re struggling with something, do you ever regret it? Do you ever think about going back to your corporate careers or doing something else? How about you, Liz?

Liz Picarazzi:
So it’s interesting that you asked, because I used to work at American Express. And yesterday, I was at an event at a restaurant in the same complex as American Express. And I was really reminiscing about my time there, and the people who I met, and how, when I went to happy hours with all my Amex colleagues, it was mostly all corporate types. But then I was there with a group of entrepreneur women. There were around 12 of us. And I talked last night about how I got a lot out of corporate. But one of the most important things I got was, I understood how much friction there is in getting anything done.

And for an entrepreneur, you’re looking for traction. And when you encounter friction, you’re going to try to find 10 ways to get through it or to get around it or get above it. The impression, for me, with a corporate company—it’s not just an Amex thing—is that there’s a lot of friction in getting anything done. So if you’re doing an eight-hour day, and you’re in meetings for six of those, which often happened with me, it’s really hard to get things done. And it’s very agitating for an entrepreneur.

So for me, I always kind of felt like a black sheep there. I felt like everybody else knew how the hierarchy worked and kind of how politics worked. And I don’t mean that in a negative way. I understand, in corporations, why there is hierarchy. I really do. But I just couldn’t play that game. I wasn’t very good at it. I like to do things that I’m good at. And I ultimately felt like I needed to do something that was more creative. As it turns out, with me, I had a business plan written for my first business before I left Amex. And I was affected by the layoffs due to the recession. And so I ended up leaving, but having that business plan in my back pocket and being able to start the business right away. And that’s a story for another day, what that transition was like.

And in terms of where I have regretted it, in the beginning of the pandemic, when I had laid off all my employees and didn’t know if PPP was really happening and had a warehouse full of inventory that I had just brought over and was paying tons to house that, you know what? If I was in corporate, I definitely would not have had this problem. And I just had to have hope that we got through it. And we did. And I feel like the government was incredibly generous with small businesses. I definitely would not have survived had I not gotten that PPP. So I guess if things had gone really south, then I probably would want to have a corporate job right now.

Loren Feldman:
Jennifer, how about you?

Jennifer Kerhin:
I think I definitely did, between years five through eight. When I started the company in 2009, it was really supposed to be started as a consulting firm, not as a business. Because I love what I do. I have a definite vision of how associations can optimize their events, and I love it. I love every aspect of it. And in the beginning, it was just me working by myself. So more of a consultancy than a business. I was totally fine.

But when I got to the point of creating the business, hiring staff, doing more complicated accounting, getting more things to build the structure, I didn’t like it, and I really regretted it. And I thought, “Why did I do this? I could have worked for a consulting firm. I could have worked for an association. This is stupid. This is taking up all my time.” My kids were little. “I hate it, hate it, hate it.” I pushed through it.

Loren Feldman:
How long did that last?

Jennifer Kerhin:
Three years. But what I should have done is, earlier on, embraced that if I was going to run a business, I should have sought outside help at that moment. Instead, I languished in misery for a couple years. And if I’d said, “Okay, this is now not a consulting firm. I’ve decided to be a business. Here are the different options for resources. There’s books, there’s podcasts, there’s CEO advisory groups out there. There’s free things from the state.”

Years later, I got some amazing courses through Maryland’s Small Business Development Corporation that were free. Go to that. I should have done that instantly to help me design my way. I had a vision, but I was very lost on the business side. Once I got through it, I was fine. And I love it. I’d never go back. I absolutely adore it now. But if you fall into starting a business without thinking that it’s a business, and you get lost, find the outside resources. That’s what helped me get out of that stage.

Loren Feldman:
What was it that you most needed to do differently during that difficult period?

Jennifer Kerhin:
Stop thinking I had to know everything. I didn’t understand accounting. And I should have hired a part-time accountant to set up QuickBooks Online for me much sooner than I did. I knew how to do the work, but I didn’t know how to hire an employee. I could have gotten some help to say, “This is how you hire your first employee. This is what you do with them”—and then how to delegate work for any sort of management, because now you’re not in the phase of just doing the work. You need to manage someone else’s work.

If I had gotten help on those two things, that would have helped me get to the next level, because I love sales. That was easy to me. You know what I should have done? I should have read E-Myth a lot sooner. I love that book, my favorite book of business of all time. And I should have read that day one.

Loren Feldman:
Sarah, you’ve shared with us that you’ve had multiple previous careers or incarnations. [Laughter] Do you ever miss them?

Sarah Segal:
Well, no. They’re all in communication. So the consistency of my career is, I’ve been in the communication industry for a really long time. And so whether or not it’s as a reporter, on one side of the fence, or the person talking to a reporter, it’s still communication.

I was just thinking back: I had drinks with an old colleague of mine from Cafe Press, which was a print-on-demand company that was pretty big at the time, that got absorbed by another larger entity. And the people who I worked with there, we’re still all in contact. We follow each other and communicate with each other on a regular basis. Because the one thing that we liked about that time period was the creativity that we were afforded.

And we were always kind of kept on our toes. It was really fast paced. And it was really nice having that comfort that someone else was paying the bills, and I didn’t have to worry about that. Because that can be suffocating sometimes for me, as a business owner, where I’m so focused on generating new business, or expanding the business, or this and that, that I forget about the creative side of what we do and why we do it.

So I’m actually working with my team to do this pretty large creative project, that I will divulge at some point soon. It’s not for a client. It’s for us to kind of get our juices flowing, and really kind of share the creativity that we have. Because, when you work in PR, a lot of the time, you give a client 15 amazing ideas, and then they generally go for what’s safe. And so we have this laundry list of really awesome ideas that never get picked up. But sometimes you’ve just got to do them yourself.

I just want to point out one thing: I love that Liz had a business plan before she started her business. I still don’t have a business plan. I’m working on it slowly. But I still haven’t been able to figure out what my end goal is, because I don’t really have an end goal. I like what I do, but is it a monetary goal? Probably not. Is it an accolades goal? Probably not. Or is it like how big are we? Probably not. So I haven’t been able to really figure out what that is. But in terms of going back to a corporate environment, I don’t think I could, because I don’t think I’m employable. I think that Jay said that on a podcast episode once or in conversation, but I don’t think I’m employable.

Loren Feldman:
He said you were unemployable?

Sarah Segal:
Well, somebody said it about themselves. And I was like, “You know what? I’m not employable.” I don’t like marching to the beat of somebody else’s drum. I am always looking for: How can we do things better? How can we change things? How can we move ahead? And a lot of bigger entities aren’t built that way. They don’t want to test-drive new ideas.

Loren Feldman:
So I would phrase it a little bit differently. I think you’re probably quite employable, but you might not be a great employee, which is probably true of everybody on this podcast.

Sarah Segal:
Yeah, I’m never satisfied with what’s being done. And I always want to make something different and do something inspired. And there are a lot of companies out there that don’t need to do that, because they have a great product that is a commodity but that people know their brand name. And I just don’t think I would fit well into that environment anymore.

Liz Picarazzi:
I’m actually hearing, Sarah, that you kind of want to maximize creativity.

Sarah Segal:
Oh, I do. I’ve kind of put myself in a little bit of a funk, because I’ve been so focused on business. We had two of our largest clients—we’re wrapping up with them at the end of this month because of financial bandwidth on their side. Literally both of them are like, “We love you guys. We’re gonna come back. But we need to take a break and get our ducks in a row and get more funding,” or do what they need to do to make really good use of us. But we love them. We think they’re great. We think that what they do is really interesting and awesome. And we’re so excited when we get media hits and opportunities for them.

So when they leave, I try not to, but I take it personally. Because I feel like I’ve failed the team. And then I’m like, to spend so much time, “Okay, so how am I going to make the numbers work? Do we have new business in the pipeline?” And then I focus all my energy on that. And I forget about the creative side that got me into this business.

And so I’m really trying to step back and go, “You know what? If we do what we’re good at, and we show the world how creative we are, specifically in the video realm, people will come to us.” And so I’m investing a little bit of money into starting to create that video content. We already edit video for clients and do all of that. But original content is kind of what we want to focus on for the next while.

Jennifer Kerhin:
Sarah, one of the things that helped me get out of my couple years of doubting and regretting that I had started a business was creating a business plan. I wonder if that would help. It gave me a sense of control. It gave me a way to direct my energies that didn’t make me seem like I was drowning. I’m wondering, I mean, Liz, you started off the right way. Because I think if I ever started another business, the first thing I would do is create a business plan. I’m wondering, Sarah—because it’s sad when you lose clients like that, really sad—I’m wondering if that might help you move forward?

Sarah Segal:
Yeah, I mean, I have a document that’s my quote-unquote business plan. And I go into it, and I work on it as I can. It’s kind of a work in progress. Probably it would be good to have somebody else put eyes on it at some point when it’s a little bit more finished. But again, for some reason, I’m stuck on this idea that a business plan has to have an end goal.

Loren Feldman:
I’m not sure you’re right about that.

Liz Picarazzi:
Mmm, I don’t think so. I think it’s really more about the process. And if you get your plan on paper, you can really ask the question: Will people pay for what I’m offering? Yes? No? How much? A lot of work to get there, but I think a lot of people, when they do business plans, work out a lot of things that they would encounter once they launch. And those are good things to know. And they can be short.

Loren Feldman:
When you put together your plan, Liz, how far into the future were you thinking? Was it the first year or to establish some stability?

Liz Picarazzi:
I think I probably did it for, like, three to five years. At least half of what I predicted was wrong. Which is fine.

Loren Feldman:
Which is probably a pretty good batting average, by most standards, I suspect.

Liz Picarazzi:
Yeah, I mean, everything from classifying employees as 1099 or W2, to how I was going to price things. Who my design target was for customers changed multiple times. But it still will narrow down your choices. And you’re gonna find 100 books about how to write a business plan. Just kind of look at which are the couple that are the best on Amazon and look for something that’s short.

I’ve even seen a book, I think it’s called, The One Page Business Plan, and I think for a lot of people, that’s kind of the way to go. And it forces you to ask questions and answers that you might not otherwise do.

Sarah Segal:
Have you ever thought about going back and updating your plan?

Liz Picarazzi:
No, I haven’t, because it’s just so many years back. For my first business, that plan was written in like 2008, or something. And then for my current business, Citibin, that was actually written in conjunction with starting it, because I was spinning it off of the handyman business. And then the other thing I would actually recommend, which you may even already know about, is the Goldman Sachs 10,000 Small Businesses program.

I did that six or seven years ago, but they have satellites at universities in many cities. And that’s something that Goldman Sachs actually pays for the whole curriculum. It’s like a six-month commitment. I think it’s like one day a month in person. But every component of a business plan, there’s like an entire unit devoted to it. So you’ll get everything with the financials, the marketing, operations, hiring, firing, HR, you name it. That was really good for me. And actually, I created Citibin within that Goldman Sachs class, because I realized I wanted to spin it off from the handyman business and get out. So I actually planned my exit for my first business in that program.

Sarah Segal:
Interesting.

Jennifer Kerhin:
I also did—it’s very similar to Goldman Sachs—the Small Business Administration’s Emerging Leaders Program. That’s a nine-month program where they meet every two weeks. It’s at night, so it’s like two and a half hours. And it’s the same thing, curriculum. Every month is a different sort of chapter. They have a leader who teaches, as well as bringing in some guest speakers. And then you do a presentation at the end. Very similar concept to Liz’s, and they help you at the end of it. You had to write a business plan and a sales and marketing plan to support it.

I, unlike Liz, change my plan. I add to it. Let’s see, mine’s two years. There’s the initial what the company is going to be, but as things have developed over the last 14 years—especially with the arrival of us getting so involved with event technology support—I have changed it. I think the first thing that it helped me to do, though, is not chase any business that came my way. When I actually put down a business plan in writing, I was able to say no to potential or current clients when they asked me for services that I didn’t think were in my wheelhouse. Because before, when I was just sort of trying to make it through, sometimes I accepted work that I shouldn’t have, that wasn’t in my core strength. And that business plan really helped me to focus on my core strength. Kind of like Pilates for business. [Laughter]

Sarah Segal:
It’s like Pilates—just core strength?

Jennifer Kerhin:
Yeah.

Sarah Segal:
I get it.

Liz Picarazzi:
I do Pilates once a week. Maybe I need to do this more.

Sarah Segal:
Can I ask Loren: You know, you ask us questions all the time about our businesses, but you run a small business. Do you have a business plan?

Loren Feldman:
No, I don’t, and I probably should. [Laughter] I don’t want to get too deep into this right now, but I’ve been kind of throwing stuff against the wall to see what sticks and what might be a potential revenue source for me—the newsletter, sponsorship of the podcast, in-person meetings, a couple other ideas that I have. And I feel like I’ve needed to try these things out and get a sense of whether they work at all. And I’m thinking that, maybe next year, I need to really put it down on paper and have a real plan.

Sarah Segal:
Seriously, I have an idea for you: You need to host a series of webinars that people can sign up and pay for where you break down whatever the questions are for the business plan, and literally talk through those. And people have to go away and do homework and come back. And it’s almost like a peer group of people that are in your situation, in my situation, to kind of light a fire under them.

I guarantee 50 percent of business owners out there, if not more, don’t have business plans. And it’s one of those things that they wish they had, and they know they should have, but putting pen to paper is easier said than done.

Liz Picarazzi:
I actually have a little bit of a coffin for my first business. It’s just a box in my office where I put all of the things that died when that business died. [Laughter] And one of the things in there is the business plan. You know, postcards I created and sent, and various things. It’s almost like a scrapbook. But I was like, “I can’t get rid of this business plan,” even though half of it or more was totally wrong. But every once in a while, I’ll pull it out. And it’s like a little memento.

Loren Feldman:
Jennifer, you mentioned that you did an original plan and that you update it. Do you update it based on changes in the business? Or do you think about it once a year or once every two years?

Jennifer Kerhin:
I would say I update it every two years. Theoretically, it’s a plan for three years, but I never make it through three years. And the two-year plan is the core: the mission and vision. And then it talks about where we’re going to focus the majority of our efforts. The last two years have been focused heavily on scalable structure. I always have a theme with it, too. So it’s a strategic plan that underlines the business plan.

The business plan, to me, is: How is this engine running? I have my customers. I have my structure. I have how I’m going to make money. So maybe I’m updating my strategic plan every two years to tie into the business plan. But in the beginning, I started the business with associations as my core customer, but I started taking other work. And when I wrote the business plan, I said, “Nope, I only want to work with associations. I’m not taking corporate clients, and I’m not going to take government clients.” It helped me focus very specifically on events and the event revenue for association conventions.

Loren Feldman:
To what extent, Jennifer, is it strategic, and kind of text? And to what extent is it financial and numbers: looking at what you charge, what your revenue will be, how much money you’ll actually make?

Jennifer Kerhin:
So there are definitely revenue goals, and net profit and gross profit goals that tie into a pipeline. So I don’t have great KPIs on what my pipeline should be. But I’m getting there. So if I want to do a 20-percent increase this year, how big does my pipeline need to be? And if it starts to fall below, I’m not going to get it, because I know, on average, of all of our proposals that we send out, we get 40 percent that turn into clients.

There’s definitely a financial side, and then there’s a lot of infrastructure in that plan. I do forecasting with my CFO. So: “Okay, we think based on this revenue goal, we should hire one FTE, full-time employee. Where would that be? Let’s think it through.” This sounds like I’m way more organized than I am, but it’s definitely over the course of like two months, every two years, that I put this to paper. Because if I don’t put it to paper, it won’t get done. It’ll stay in my head. It doesn’t get communicated. It forces me to put my plan to paper, and then say, “Okay, nope. I agreed I’m only focusing on associations.” That was years ago. This time, now, I’m adding two new services. “How am I going to do that? This is how I’m going to do it.”

Loren Feldman:
Sarah, I’d like to go back to the clients you were talking about. You said that you parted on good terms with them, but you still feel kind of a sense of responsibility for it. Did you learn anything from it? Do you think you could have done something different? Or was it purely their experience?

Sarah Segal:
It was purely their experience. I mean, there was nothing we could have done. Like, literally, it’s been all accolades, how much they like working with us and how great the team is. It’s just financials. It’s not the first time that we’ve had to ebb and flow with clients, based on their financials. It’s just the way of the world. When businesses are looking to cut costs, it’s outside agencies that go first. But when it’s two of your largest clients in the span of a week, it’s like, “Really? Can I go dig a hole, put myself in it, and just stay there forever? Until it goes away?” It’s kind of crushing, because literally, a week before that, I was like, “Wow, we’re on a good track. My P&L looks great. These are all good things.” And then all of a sudden, it’s like, “Oh, okay, not so good.” And getting those big clients is a lot of work.

I just found out yesterday, we had submitted a last-minute proposal through a connection of ours to work on a very large city project for San Francisco. And we found out yesterday that we didn’t win it because they were going with an agency that was bigger. Literally, that was the reason. That agency doesn’t have as many staff in San Francisco as we do. But because they had big name brands—they had worked for more familiar brands—that’s the reason that they’re going with them. They’re going with what’s safe.

We’re not on the radar yet of larger brands, or household-name brands. We’re still in the smaller regional businesses, which is good, and we like it a lot. But having those bigger companies with stable sources of revenue that aren’t going to look at you and say, “Hey, we ran out of funding, you’ve got to cut back for a while,” would be a nice goal. It would be nice to get those, so I need to spend a lot of time kind of figuring out how to put myself in front of those potential people. And it’s like, going to conferences, speaking, more contributed content. It’s the thought leadership, because it’s go where they go.

Liz Picarazzi:
Sarah, I’m curious, do you ever work as a sub? Like, let’s say it’s an advertising agency that’s going beyond just the regular marketing into the PR realm for big brands. Is that ever a way that you can kind of get on to a larger brand’s work?

Sarah Segal:
It is. We’re looped in with a handful of marketing agencies. Most of those marketing agencies don’t have the big, big clients. So I have started sourcing out and just trying to get on the radar of some of the other larger advertising and marketing agencies. Because a lot of marketing agencies, you go to their website, and they’ll be like, “Oh, we do marketing, and we do PR.” And then you look at their headcount, and they have like, one person that does PR. You’re like, “Okay, so you don’t really do PR. You say that you do PR, but you don’t really do PR.”

The only way to get in there is getting acquainted with these folks and introducing yourself as a sub, but yeah, we’ve done that in the past, for sure. Just not for any super major brand yet. I mean, there are big brands that we do work for. Like, for example, Birdies is a national shoe company. And we work for them, because we were brought in through their creative agency. And so we actually edit all of their digital advertising video. It’s really random, but it’s a capability that we have, and we’re very good at it. And so we just turn that around for them.

Loren Feldman:
Sarah, have you rethought your marketing strategy at all in light of losing these two clients? Are you doing anything different?

Sarah Segal:
Oh, I am. I am! So this kind of just happened over the last couple of weeks. But we do a lot of grand openings for our clients, a lot of brick-and-mortar stuff, where they’re opening a new location, or whatever. And so we end up, a lot of times, working with the Chambers of Commerce for regions. And we, in conversation with them, have found that we have a lot of knowledge that we can provide to the Chamber memberships. So we’re going to be offering complimentary webinars and in-person sessions that focus on PR and media relations and social media management for a handful of chambers in our region. And we’re going to kind of test-drive those, just to kind of continue to just get our name out there.

You know, we are becoming known, specifically in the Bay Area, because we have so many Bay Area clients. But the Chambers are great, and they’re responsive, and they work with every size business out there. So if we can continue just to offer up something that’s easy for us—like, I’ll talk about media relations until the cows come home, and you don’t have to pay me for that. So that’s what we’re doing. It’s a new new-business thing, in addition to some creative stuff that we’re doing.

Loren Feldman:
Jennifer, have you ever hired PR help?

Jennifer Kerhin:
I have not. We’ve talked extensively on the show about how marketing has been not really great for me. It’s not been my strong suit and sort of ignored. But no, never done PR. I’m always interested in what Sarah has to say.

Loren Feldman:
Liz, you have. How did you find the people you’ve hired in the past?

Liz Picarazzi:
So, I was in a kind of a women’s entrepreneur group really early on. And one of the women in the group was starting her own PR firm—a husband and wife team also, which I’m very familiar with. And so, interestingly, I was going to hire her. I think the retainer was like $5,000 a month, which was definitely more than I could pay, but I still took the leap. And she got me in The New York Times, like, immediately in that first month, which was a really big, big step for us. That was in 2015, a long time ago.

So in that situation, it was worth it. But what I will say is that you’re supposed to kind of continue on with the publicist for a couple months after that to kind of promote the publicity that you got. So I did another month, and I got literally nothing from it. And so I thought to myself, “Well, I aimed high, and I got exactly what I wanted. Do I want to keep going for it at least, at least at this stage?” And I decided not. So I cut it off after the second month.

Sarah Segal:
Oh, wow. That’s quick.

Liz Picarazzi:
Yeah, it was really quick. And I don’t know if it was too quick. However, I am very good at PR. And I spend a lot of time on PR, even though I wouldn’t call myself, “Oh, I’m like part-time publicity.” Like, I am. And I enjoy doing it.

Sarah Segal:
Is it a good use of your time though?

Liz Picarazzi:
Ummmm… hmm.

Sarah Segal:
Because a lot of people—PR is not brain surgery. It’s not.

Loren Feldman:
Although, let me stop you there, Sarah.

Liz Picarazzi:
I don’t know about that, Sarah. That kind of undercuts what you do, then.

Sarah Segal:
No, I mean, it takes time to learn how to do it and do it well. But the physical acts of what we do are not super complicated.

Loren Feldman:
But it’s not well understood.

Sarah Segal:
No, it’s not.

Loren Feldman:
I would ask Liz. You said they got you in The New York Times in the first month.

Sarah Segal:
That’s kind of great.

Loren Feldman:
But why did that happen? Did they know something? Did they do PR really well? Or did you just have a good story to tell that hit The Times at the right time? How did that happen?

Liz Picarazzi:
So Loren, that’s actually a good question. Because I think it may have been that I had a really good story. And it still was totally worth paying to get that, but I realized that a lot of what was in the release, or whatever, was stuff that I probably could have written myself. But at the same time, I didn’t really know how to work it. So our publicist, she had a contact in the real estate section of The New York Times, which is where it ran. So I guess I’m kind of talking out of both sides of my mouth here.

Loren Feldman:
Well, that’s valuable. She had connections. That made a difference.

Liz Picarazzi:
That’s super valuable. Yeah, yeah. I mean, I often just ask, “If I were the journalist, what would I want? What information would I want to be able to decide to do the story, decide if it’s interesting, or decide I have the right media?” So when I got really focused on doing that, it’s almost like, I feel like I’m sometimes feeding them the stories. And a huge percentage of it that ends up in the article will have come specifically from what I gave them, including the names of competitors and links to competitors.

I realized that a while back, that if you’re writing to a publication that’s going to look at a category—let’s say package lockers—they’re definitely gonna be interested in what I have to say. But I think they were more interested because I made their job easier. They didn’t have to research who my competitors were, because I gave it to them.

Sarah Segal:
Do you want a job? [Laughter] But again, is it a good use of your time? Because, yeah, you know how to do it. You know how to do it really well. But should you be doing it? We get a lot of clients where it’s like, “Yeah, I know how to do this. I can talk to reporters.” But should I be spending my time reaching out? Or should I offset this, because it’s time consuming?

Liz Picarazzi:
Yeah. I don’t know. I kind of enjoy it.

Loren Feldman:
There are advantages to doing it yourself. I would say, speaking as a journalist, I developed relationships with people who reached out to me directly through the years that have lasted for many years. And I don’t think it would have necessarily happened if it had come through somebody else.

Sarah Segal:
Yeah, but I’ve heard from a lot of reporters who don’t like working with businesses directly, because most of them don’t understand the timeline, the deadlines, the image requirements, and how not to try to use it as a commercial. A lot of people will try it, and we spend a lot of time working with clients, being like, “No, if you want a piece of contributed content to run, you cannot be writing it like an advertisement for the business. You have to put it in context.”

We work with a hotel, and I’m like, “Yeah, we can get a travel reporter to come and write about the hotel, but they don’t want to write just about the hotel. They’re gonna want to write about the whole region.” So we’re gonna have to make friends with other hospitality providers and make it a whole thing. And they quickly got that. But it’s what you said. You’re pitching yourself, but you’re pitching your vertical as well. You’re giving people a heads up on other players in the space, which can help and obviously hurt you in certain ways. But that’s what they want. They want a trend story; they don’t want to just write about one entity.

Loren Feldman:
Sarah, we’ve had this conversation before, once or twice, with Jay Goltz, where he has said that he’s surprised that he doesn’t get more pitches from PR firms directly reaching out to him. Have you thought more about just picking out businesses that you would like to work with and contacting them directly?

Sarah Segal:
Yeah. I find that cold emailing doesn’t work, though. So I’m just going to tell you that much. My gut is, I’ve definitely reached out and given case studies or provided them with, “Hey, I saw this opportunity and thought of your brand.” And those don’t usually go anywhere unless there’s a connection. But for example, we manage the social media accounts for a bunch of clients, and this really cute company based in San Francisco reached out through our client’s Instagram handle, because they make custom-branded dog toys. And so they—

Loren Feldman:
Custom dog toys?

Sarah Segal:
I know it’s weird, but it’s called—can I say their name on this?

Loren Feldman:
Sure.

Sarah Segal:
It’s called Goodboi, spelled g–o-o-d-b-o-i. They’re based in San Francisco, and they created a prototype of a doughnut box and a doughnut, both of which are dog toys, and reached out through Instagram to say, “Hey, who can we send this to the doughnut company to consider?” which I thought was super cute. So I reached out back to them, and I got my staffer to get me their email. And I was like, “Hey, you guys are small, you’re up and coming, but I think what you’re doing is really interesting. I’d just love to grab a coffee or something and put us on your radar for when you’re ready.”

We did that recently with a local distillery. Because one of my staffers was like, “Oh my God, this place is awesome. And they don’t do PR.” And I was like, “Okay,” and so I reached out and said, “Hey, we just want to be around for when you decide you want to invest in PR.” And we got a meeting with them and sent them a proposal. And I don’t know if it’s gonna happen right away, but they know that we’re there now. And so that’s kind of how I’m going about those.

Liz Picarazzi:
Well, they could also develop a budget in the future based on your quote. They may not have it now, but they could say, “Yeah, we’re gonna get this started in 2024.” I think that’s a really good approach.

Loren Feldman:
When they do their business plan. [Laughter]

Sarah Segal:
Yeah, so I think that cold doesn’t work, but warm does. So I’m kind of working on the warm, and that’s why we’re gonna do the Chamber of Commerce stuff, because it creates warm.

Loren Feldman:
We only have a little time left. Liz, last time you were here. You told us that you were in the process of preparing a presentation for your EO group about impostor syndrome. And I’m curious, did you go ahead and give that presentation? And how did it go?

Liz Picarazzi:
So I did give the presentation. I did not know that you were going to ask—that’s okay, Loren. I’m glad you asked. It’s nice to reflect on it.

So you know, I’ve had a lot of growth in the company in the last couple of years. And I’m finding myself in a lot of situations that I feel in over my head, or things that I don’t like to do that I need to do—anything that’s legal or taxes or insurance, any related stuff like that. And so, kind of figuring out what I’m good at and what I’m not good at has been really important, because then I can acknowledge what I’m not good at. And I can make sure that’s delegated. And I’ve made a lot of progress in the last year, delegating more.

So part of it was like figuring out what I’m good at and bad at, but then part of it is, I’ve encountered a lot of new people in the last couple of years since we’ve been doing city work. So one thing I distinguished in this presentation, which I had a coach for, is that there are a couple of situations I’m in where I feel really vulnerable in terms of, “Well, what is my subject matter expertise? I am not an industrial designer or an architect. Like, what business do I have making trash enclosures? You know, these people have all their journals and their white papers all about how to do various forms of public-use goods. And not that I necessarily think that they should put Citibin in there, but I guess I sometimes feel sort of threatened. Like, “Well, if these people are the arbiters of good design and good use of public space, maybe I need to understand that better.”

A lot of it had to do with design. A lot of it had to do with figuring out what I’m good at and not. And then I would say the underlying worry of all of it that comes up is that I sometimes wonder if I’m the best person to run my own company. We’re growing. I’m feeling good about that. I’m doing a good job, I think, but there are a lot of things that are starting to feel really chaotic, like hiring people quickly or changing some big things with operations. Maybe someone else would be good at doing all of that. And that is imposter syndrome, because my seven EO mates in the room all said that they all, at various points, and many of them currently, have impostor syndrome. I mean, it’s not rare. It’s really common, depending on what profession you’re in.

And actually, I would say entrepreneurs probably have less impostor syndrome, because we’re really bold, and we’re really courageous. And you know, you’re not going to be overwhelmed with impostor syndrome to the point that you aren’t going to be an entrepreneur. Like, you can still get through it. So, it was a really good presentation. I think it was good to distinguish where I see myself feeling the imposter syndrome and how can I sort of address it? Definitely very cathartic.

Loren Feldman:
You’ve told us in the past that you’ve asked yourself whether you’re the right person to do this or not. Did going through this process of preparing and giving the presentation affect your thinking on that at all?

Liz Picarazzi:
So I definitely still think I’m the best one to lead my company. I feel like I have kind of shed that for a little bit. I don’t know if this is a fully formed thought, but I’ll say it anyways. I feel like if my company keeps growing organically that I’m going to be really good at my job. But if I got outside funding or something happened where we really blew up, and we’re huge, I think I would not be good in that situation. And that’s good to know. Because then it’s like, okay, well, maybe I’m not always the CEO. Maybe I’m gonna become the chief creative officer. I kind of am that in many ways right now. And I love that.

Loren Feldman:
Sarah or Jennifer, have either of you thought about this at all?

Jennifer Kerhin:
I think no one will love my company more than me. I think of it as, I don’t know what I’m doing every day, but I will smother it with love. [Laughter] And I will find the answers. It’s like when you’re a new mother. You know, you love that child more than anything. Do you know all the right answers? And when you see the mom who has four kids, you’re like, “Man, they have it all together.” Right? Do I know everything? Nope. But I have a vision and a desire. And no one’s going to put as much effort and love into this than me.

Loren Feldman:
All right, we need to stop. My thanks to Jennifer Kerhin, Liz Picarazzi, 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.