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From Startup Survival to PR Empire: Jennifer Kaplan on 22 Years of Building Evolve PR
Introduction
Hello again everyone. This is Doug, and you’re listening to Leadership Powered by Common Sense. Hey, have you started a business out there? Was your dream enough to get you over the goal line, to get you started and get you into it? Well, hopefully, if that’s your story, you’ve been at it a while. My guest today certainly has. She started a business at age 30, and I’ll let her date herself past that. But she’s got a great story to tell and share with us. My guest is a lady named Jennifer Kaplan. She goes by Jen. So, Jen, welcome to the show.
Hi, Doug. Thank you. I’m excited to be with you and share the story and explore. You know, what we can share with others.
Meet the Guest: Jennifer Kaplan of Evolve PR
Yeah. So tell us about this labor of love. What was the original idea you had?
Well, my mom would say that I was born doing PR and it followed with Senior Most Talkative in high school, and then went to Arizona State University and studied communications with an emphasis in public relations.
I would say that during that time I maybe thought I wanted to be a sports agent or, you know, channel it somehow. I didn’t think traditionally I’d be doing PR and have a firm, but I come from a family of entrepreneurs and at 30 decided that I was going to start my own business. And here I am, 22 years later. We’re the largest PR firm in Arizona now, 28 people. There are a lot of full service agencies that have 50, 60, 70 people. But we’re solely PR. So as a, you know, niche business and just PR where the largest out here, I’m one of the larger ones across the country. And yeah, so I’m doing what I love and something that I really was passionate about as a young kid and loved connecting people and networking and helping elevate individuals and businesses. And yeah, so it’s — I feel very blessed that I’ve been able to do that.
Key Discussion Point 1: Pivoting and Surviving — The Entrepreneurial Journey
Well, first let me say congratulations on the long run. You know, in the entrepreneurial game, I think the SBA tells us that a lot of businesses don’t make it past the five year mark.
And it’s way up there, 80 something percent, I think, don’t make it past that five year mark. So kudos to you for that event. And as I think on a 22 year timeline, there’s been a lot of things that have happened in the market and with technology and a lot of other things along the way. So tell us some of your pivot points as you grew your business, what were some of the inflection points that you had to consciously make to keep things going in the way you wanted them?
Yeah. You’re right. Reflecting back in that time, I mean, obviously the more recent was Covid and how we navigated that as a business because we didn’t know. You know, I think that — well, starting out at the beginning, it was a little bit of fake it til you make it because you want to try and walk the walk and talk the talk, because when you’re new, you have to establish credibility and you have to establish, you know, why should someone trust you and hire you? You don’t have — you have — you kind of have nothing.
And so it’s getting those individuals to give you the chance and give you the opportunity, and you have to stay positive and, you know, not let that kind of beat you down. Being new and fighting, you know, for that spot in that space in your industry. One of the things that I did not necessarily consciously by design to help my business, but I ended up getting involved in the community, and I feel like that’s a really great way. Whether that’s networking or being on a board or getting involved in, you know, fundraising for a non-profit, you get to meet and network with so many different people in a little bit more of an authentic way than it being sort of a forced, which the force type of environments are good too where it’s very, you know, exchanging cards and all that.
But I found myself for probably about ten years when I started out my business in an environment where I was, you know, meeting other peers and meeting other people in, you know, in just the community through being involved in non-profits and fundraising.
And that even to this day, those relationships are still with me. And those relationships, you know, end up coming back and we reciprocate, you know, with each other of these people that I met along the way. So that was a pretty big one too. So and then there was, okay, we’re — we got to put kind of our big girl pants on. Now we’re established and we’re building our business and elevating that and being able to deliver and grow. And, you know, growing can be really scary investing in the business. You put money in your pocket, you put it back into the company. Where is that tipping point where you hire? Do you have clients that, you know, justify that? It’s a scary thing. And putting my head on the pillow every night, knowing that I’m feeding some mouths, you know, helps drive me.
And I think it’s important for people to figure out what drives them. I’ll talk to some people. They’re like, oh, no, no, I could never have more than two employees or five employees.
And so I think it’s really important for people to be in their comfort zone and what’s safe for them to be able to thrive. And for me, there was kind of this high, to continue growing and, you know, build it — but not without fear. My mom calls fear the real four letter F word, because I think we all have that. And so without that, I mean, we’re not really challenged. We kind of have to have a little bit of that inside. So all of that — very long winded — there were different, you know, journeys along the way. Like I said, the fake it til I make it and being involved in the community and seeing where there’s growth and taking those risks are all part of, you know, that collaboration of getting to where we are today.
The Real Shape of Business Growth
Yeah. You know, as you were saying that I was reminded that, you know, when you go to business school, the charts and graphs for business are usually these gently sloping upward to the right lines.
But in the entrepreneurial world, that’s not it at all. It’s giant stair step kind of things. And like you alluded to, just if you’re a solopreneur and you decide you want to hire your first person that incremental amount monthly on your expense line — that’s a step up. That’s a giant step up. It’s not a smooth curve. And if you keep going along that journey and you get into, you know, buying extra equipment for your operation or buying, maybe expanding an office commitment, you know, to something. Of course, now, I know we do a lot of hybrid things, but, you know, there was a point in time where you had to have a place for everybody to work. So there was a facility charge on your balance sheet and income statement. And you know, if you plot all that out, it’s those giant stair steps that plot the real progress of a small business. And as the owner, that’s scary. It’s like, you know, you’re at a certain level and you’re doing okay, and you know, you need that extra person or that extra machine and it’s like how? What if. Oh my. Oh goodness. You know. So it is that fear factor that you alluded to.
You’re so right. And the impasse that I got to with literally all those things you just said — the space, the environment, the tools, the resources, the insurance, the benefits — all of that was retention. And that’s when I realized I was having, as a young entrepreneur, some turnover and some challenges. And I was looking at why is this happening? And I had a key employee at the time bringing to my attention that you need to be doing other things in order to get the team to stay, retain, you know, be committed. And that was a game changer.
And so you’re right, investing back in the company and into your people, you know, you hear that — you know, people’s culture and mission statements. People first, people before profits, all of that. But when you’re a young entrepreneur and you don’t know what the next day is going to be or you’re still establishing yourself, it’s really hard and really scary.
But I kind of got hit in the face with it and I said, you know what? I want to grow and I want to retain people and I want to be competitive among my peers. And so you have to do those things. And yeah, it’s — it can be a big nut to bite off, like you said, with overhead. And what tools do you need in your company to make yourself competitive and almost separate yourself where and when you can from, you know, your competitors too? Yeah.
Key Discussion Point 2: Letting Go — The Chief Everything Officer Trap
Well, let’s talk a little bit about internal. And by internal I mean not just inside the company but inside your own head, if I may, Jen. When did you realize you needed to stop being Chief Everything Officer and start delegating and giving up some of the white knuckle grip you had on the business.
I’m sort of embarrassed to say this, but it’s actually only been more recently. You know, you would think after 22 years, maybe that happened ten years ago, but it’s been only more recently, I would say in the last five ish years.
I hate to keep — you know, I referred to Covid earlier, but, you know, in a traditional sense, I was an in-office person. Every day you show up, you do your job, you’re there for X amount of hours and Covid, you didn’t have a choice. You were hybrid, like you said now, and other things that afforded flexibility and grace and all that. Where I was like 9 to 5, hour lunch, you know, all of the things. And so Covid was the start for me in kind of leaning back a little bit and feeling like I have to trust that Doug is doing his job. And I have to trust that even though Doug is home, that he’s not just, you know, watching TV and, you know, just giving his dog belly rubs — I don’t know, you know. I had to trust that the process of the team was going to rise and be successful. And I found that a lot of people actually did better and were excelling more with some of that space and flexibility.
But I was in the traditional, you know, my sort of time was a little more structured. So for me, it started with Covid and then it’s just gotten more and more longevity with my team — my VP’s been with me 13 years, my director ten. And so when you have those types of employees, then they also, you know, can run it sort of without me as hands on where before it’s like, well, I have to be the one to do it. No one else can do it. It’s a hard place to go. The one thing I will say, which I know my team sort of rolls their eyes with — with 28 people on the team, about 140 clients, I am on every single email. Every email. So that’s a lot of emails, because if they’re sending more than ten a day, even just, you know, back and forth coordinating something with one client. So it gets to be a lot. But I’m not ready to give that up yet.
Well, maybe we’ll do some coaching about that.
Yeah, I do need some of that. I do know. Yeah.
The Law of the Lid — John Maxwell’s Timeless Leadership Principle
Well, I asked the question because it is a topic we’ve talked about on this show quite a bit, and I tell the story that I observed it in my banking days. I saw owner founders who had great ideas. Their company went through some evolution of their own. I tend to look at businesses in a four stage idea — you know, startup, grow up, scale up, and enterprise — and you can’t really scale until you grow and mature a little bit in your systems and process. You typically don’t have a way to think about that until you’ve gotten through startup, and startup is that really messy, ugly, undefined time where so many things are up in the air. You’re chasing rabbits and trying to get some traction and get a revenue flow going that can fuel your idea and get you there.
And so it’s all understandable. But all too often, and this is the point I observed in my banking days, you get into that second or third phase and everything gets capped by the founder’s ability to engage or make the changes they’ve got to make to allow future growth.
John Maxwell calls it the law of the lid. You know, everybody’s got a lid and you can’t go beyond that unless you as the individual, the owner, founder in this case, are willing to do some work to lift that lid and create some mental capacity and emotional capacity to let go, let others have a piece, let others take the reins and do some things. And that’s hard. It is a very hard transition to make. The inevitable reality is that lid is going to be ever present until you do some work on it, and if you’re okay with that, if you’ve gotten your company up to, let’s say, 5 million revenue or 10 million revenue, and it’s created a lifestyle for you that you’re comfortable with, and you don’t want to go beyond that — great. Good for you. You know, I’m not saying that’s a problem. But if you say you really want to continue growth and so that you can be the biggest, baddest, you know, greatest solution out there, well, you’re going to have to do some personal work to make that happen. 100%.
Yeah. That’s a lot of — I think that’s on the, on the daily, you know, to be able to reflect and look at that. And I am still reminded, you know, I said Covid and my, you know, the other leaders on the team, but on the daily basis, there are individuals on our team that come to me that want to be involved in something or take ownership, you know, of an aspect of the business. And where, you know, previous Jen would not even conceptualize that. Where I’m like, you know what, you have to trust the people, trust the process. But the business doesn’t scale. You know, if I’m creating that lid, how is it going to thrive and grow? But I still have to gut check myself a lot.
It is my baby. And the identity of, you know, I never had kids, but, you know, you give birth to a child, you name it, you mold it, you form it, you give it all the love and all that.
And that’s what I’ve done with Evolve. And so for me to just say here, you know, take it and relinquish it to others — not really, you know — but just give some of that responsibility. But I know for a fact that if I didn’t give up what I gave up — in kind of like you said, I love that that lid kind of theory — then we wouldn’t be where we are. We wouldn’t be 28 people. We wouldn’t be 140 clients. So that’s something I would say to any entrepreneur. You have to do that. I mean, unless your business is such that you couldn’t scale it anyway.
I don’t know what you know — even if you’re a psychologist or a therapist, you can hire other therapists and train them and grow a business, you know. So it’s really important to look at that and yourself and make those decisions. Like you said, you can stay at a certain dollar amount or a certain level, but I don’t think you’re going to grow if you don’t.
The Ultimate Test: Can Your Business Survive Without You?
Right. And speaking to the owners out there, there’s a real simple test on whether or not you’ve begun that change in your own business. And that is, can you take a week or two off totally by yourself and unplug and the business survive? And to many entrepreneurs, the answer to that question is no, I can’t. And you know, on the flip side of that, I know a young man who owns a construction business in Florida. And when I first met him, we were talking about where he was in that journey, and he said, oh, I can tell you my company passed that test with flying colors. He said, I took a month off. I took my family to the islands. And, you know, we bopped around the Caribbean for a whole month. He said, I had three phone calls, not because there were crises, but it was just check ins and everything was running fine. I got back. Sure enough, everything was just great.
Nobody had skipped a beat. Projects were still on track because he had built a culture with some delegation and some authority dispersed to appropriate levels in the business so project managers could keep things going. General superintendents could keep things going without him, and they all knew what his standard was, and they continued to execute and made the decisions they needed to make in his absence. And it wasn’t contrary to what he would have done anyway. And, you know, it was all a good result.
I solely, totally, 100% agree to the degree. I mean, that is the essence of it — is being able to step away for a period of time. This summer will be the fifth year that my husband and I — and I only recently got married in the last 4 or 5 years — but we’ll leave for the month of July and go to Europe. And, you know, you’ve got a time difference. You’ve got — now I bring the laptop. I don’t set an out of office. I do check my emails daily.
But that’s again my — in the morning get up, like that’s fun for me. It’s not on the phone working all day, any of that type of stuff. It’s just me, you know, kind of going through the emails. But yeah, I agree with that. I mean, all of your points about, you know, how entrepreneurs and leaders can be empowered and have balance and grow their business — spot on. I mean, that’s — that resonates for me.
Key Discussion Point 3: Hiring for Culture AND Competence
Well, and so much of that is predicated on the need to identify and hire the right people. And as you alluded to, be able to retain them, get them on board, let them drink the Kool-Aid that you’ve made and enjoy being a part of that venture, knowing they’re doing good work. What did you discover as the most effective way when you were out there hiring. How did you identify the talent you really wanted?
That’s a good question and something that I feel we’ve been so fortunate with the individuals on our team.
I mean, we have had our zig zags. But just the way we’ve created the process of, you know, from the relationship and getting to connect with people — doing in person, you know, talking to them, getting to know them during the hiring process — as well as the tactical, you know, we give them a writing assignment. And, you know, so I think there’s a balance of hiring someone, you know, from the personality standpoint and feeling that they’re the right fit for the culture, but then also knowing that there’s a job that we have to do and making sure that they can, you know, right.
And there’s, you know, like I said, some other things that we do in that process, hiring process. And, you know, again, sometimes there’s some misses and it doesn’t work. But it’s so crazy in our particular environment — we have individuals on our team that have become best friends in their weddings, become roommates, have moved, you know, visiting individuals to other, you know, when someone has moved, individuals from the team have gone to visit them in other cities.
And I think that that’s really special and unique — is to create that culture, because the retention that we talk about is on paper the benefits, the, you know, snacks and the thing, you know, and the pantry, whatever it is. But the culture and liking the people that you work with is really important because — and I don’t mean just a boss or a manager — their peers in their environment, they have to go and sit with them or talk to them or interact with them on a daily basis. And so I think that’s just as important when people are hiring is to look at that.
We after the fact will do some tests like some little fun person — not fun, like they’re real personality tests like Myers-Briggs and things like that. More so to know people’s traits and nuances. But we’ve never done anything real specific other than making sure we connect on that personal level and make sure we’re hiring someone who can deliver on the skills and the tactical side — not just one or the other.
The Practical Test: A Hiring Game Changer
Yeah, I like that. I had that same experience back in the day when I owned a company that I had built. And we, you know, quite honestly, we were struggling with hiring for quite some time, and because the method was pretty much just basic interview and resume review and that sort of thing. And, you know, in most any industry, people can fake it with the terminology and the language and they can sound like they know what they’re going to do. But it wasn’t until I created that tactical practical test. And as soon as I developed it, what I discovered was even in my phone screen, I would tell people, when you come in for the physical interview, we’re going to have a practical test we’re going to give you. And I’d have people hang up on me at that point. You know, they’d click — the phone would go dead. Yeah, okay. Check them off. You know, having a good solid no right there as helpful as anything.
But even the people that came in for the test, I had it structured in a way that I knew someone who knew the work, knew the industry, knew the business could probably get through my test in about 15 minutes. And if they were faster than that, probably not right. And if they took significantly longer — I had people sit for over an hour trying to massage the test, and I knew then you don’t know what you’re doing. And if it’s taking you that long — and, you know, I had — what’s the reverse of an Easter egg? I had intentional errors in the work that needed to be identified, and that was part of the test. It wasn’t just going to be 100% just, you know, crystal clear and complete. The whole point was being able to identify some exceptions. And if they identified those and got them right, you know, then that was a great indicator of them really knowing the work. Then we go back to the personality thing.
If they sounded and felt like they could be a good fit culturally to who and what we were or what we were trying to build — it was a win win. When I did all of that, my success rate in identifying good people probably tripled in the ability to bring them on. And the other element of that, by the way, folks, if you’re paying attention to this, is when you bring a new person in, if they can’t carry their own weight, it’s unfair to the team you’ve already got, and they’re going to feel insulted that you agreed to hire somebody that was less than.
Yeah, I agree. And they went through the same process when they got hired. So if we, you know, compromised in an area, they’re all going to know — you know, we held them accountable for the standards that we want and we expect, you know, at the company. And you’re right. It’s like, well, wait a second. If I went through the same thing that they did, how did they get hired? You know, so I think it’s — and it’s the questions you ask and you hope that, you know, they’re authentic and, you know, in the process.
But yeah, we only — not really. Yeah. I mean, recently ish, you know, again, I feel like we kind of grew up another layer or elevated another layer since Covid, you know — and giving the test and the in person, you know, and all of that. And I think that’s a game changer for the reason you just explained to you — kind of you get to weed out people who don’t want to do the test or come in person, or a combination thereof. So, yeah, I think it’s important to do that as well. But all that is learning as you go and you’re like, wait, something’s not working here. Yeah, right. Change it up. Like, if we’re not getting the right people, maybe we need to do this. Or if we’re not growing the business, maybe we need to do this — like you have to. You know, as an entrepreneur, you have to continually be looking at ways to improve and not just think the same way you’ve been doing.
It is going to be good forever.
Key Discussion Point 4: The Best Advice — Get Rich in Your Niche
Very good point. Jen, you mentioned growing up in a family of entrepreneurs. Perhaps it came from there or came from another voice or source. What was some of the best advice you got along the way?
Oh well, one that is more recent ish and probably the last six years. My mom said, get rich in your niche. And that’s because I felt like there was a moment where we were maybe leaving money on the table with social media and everyone’s doing social. You need, you know, we should offer social. We have these companies, these businesses. We’re doing PR under the whole marketing umbrella for them. Social falls under that — hired people, got the tools, got all the things. And I don’t — I mean I’ll do social media when I’m on vacation and doing this and doing that, and we do it for the company. But I mean, like for me as something I’m passionate about — and people didn’t want to pay. They’re like, oh, you know, and I can have an intern do that.
My daughter, my son, my neighbor — you know, they’re all those young people, they know social media. So there really wasn’t a huge value in them seeing social media. And I was beating my head up against the wall because I’m like, this needs to be, you know, a revenue stream and something we do as an organization to add value to our clients. And my mom said, get rich in your niche. And I went, done. PR is my niche. That’s where we’re going to grow the business. And, you know, we found places for these people to go in other companies and, you know, closed up the social media. So that was a big one from my mom.
Like I said, the fear being the real four letter F word — you know, getting that from my mom as well and just knowing that taking a risk because as an entrepreneur, you’re taking a risk every day. Every day you’re taking some sort of risk. And I don’t mean like the big risk of jumping off a cliff.
You know, just small decisions and not, you know, getting in your head and holding yourself back. So there were some isms along the way, and just seeing my brother — three years older and has a large company, and you know, how he’s navigated and the commitment that you need to make in order to grow your business. So, yeah, I was fortunate to have it with my family and then a few people in the industry as mentors, you know, giving me their, you know, their advice along the way. So just trying to, you know, take those nuggets and that information and learn from them and incorporate them into the business. But it’s a daily ritual. You know, any — I mean, maybe Jeff Bezos isn’t thinking about those things anymore, but, you know, yeah, for us small businesses, it’s a daily ritual, you know, to continue to hear and listen to others so you can take those lessons and grow.
Behind the Scenes: Marriage, Partnership, and Business
Absolutely. You mentioned the big life change. Getting married relatively recently. Is the husband involved in the business at all?
Well, you’re very intuitive, Doug. Excellent question too. So he was retiring from a career when I met him, and I met him the September before Covid. And so his retirement, you know, happened through Covid. And it was at a time where we were looking — he’s not a PR person — for someone that could take us to the next level from a COO perspective. And I think that’s an important role and a role that needs to be trusted. And I had someone who was with me that did, you know, some of the accounting and some of the payroll and other stuff. But anyway, yes. So he retired on a Friday, and then Monday started at the company and we weren’t even together a year yet. And here we are together almost seven years. But he says that if we weren’t working together, he’d never see me. So it’s probably a good thing that we get to work together.
I never thought, you know, people are like, oh, I could never work with my spouse or my significant other. But maybe because he’s had his career and, you know, we’re in our 50s and not looking to fight for a spot. And my company was, you know, already about 15 — I’ve been doing it, you know, for a while — established. He could come in and just elevate it. So yes, he is in an important role, but he does everything but PR.
Setting Boundaries When Family Works Together
Well, all great story. And yes, it is absolutely possible. As some of my listeners know, my wife and I — the company I alluded to with the hiring practice — she and I ran the company together. And we did — we even along the way hired some of our children who were approaching adulthood. They spent some time with us. But the one thing we did, we created some bright lines around areas of responsibility and authority, including what we told our kids — you know, hey, at work, we’re not mom and dad.
We’re co-owners of this company. And when we say jump, you jump. And I — we laugh now about this. Our youngest son came to work for us. He was not one destined for college. He had watched his older siblings. He wanted no part of that. But he came to work for us and was doing a good job. But then he kind of started taking advantage of the situation and I put him on probation. I said, you’re not going to be any different than any other employee. You got a 30 day notice here. If you can’t get your act together, you’re out. Well, he got his act together. And long story short, he basically followed me in the career path after that and got into the banking world, which is where I had come from and what this company was kind of related to, and has made his own career doing some of that. So, you know.
Those things are so important.
It can work. I guess that’s my message to everybody.
It can work. But if you’re the owner, you got to be bold and set those boundaries and live by them and walk your talk. And I can vividly remember things — people come into my office and they’d say, I want to talk about blah, blah, blah. And I’d go, nope, that’s Susan’s, that’s her domain. Go talk to her. Yeah. And she would do likewise. No, that’s not me. Go talk to Doug. You know, and pretty soon people knew where those lines were.
Yeah. And that shows a lot of respect to each other, you know. So if people are entrepreneurs with a family member, you know, it’s really important because then the staff and the employees think it is a little bit loosey goosey or not as taken as seriously. And so with us, same thing. You know, he’s the hard line in what he does and I don’t — even that’s his domain. And then same on the PR side. Of course we’ll gut check each other if we need to check in, which is nice, but, yeah, I think that’s important for not only the relationship, even if it’s not a married situation, just for any family relationship.
And then again, I feel like the perception for the team, it’s important as well.
Closing Thoughts
Totally agree. Well, Jen, this has been great. Thank you for sitting in and sharing this with us. Tell people how to get in touch with Evolve.
Well thank you, I’ve enjoyed the conversation. Our website is usually the best. It’s got all the info and the clicks to get everywhere. Evolve PR and spelled out and marketing — evolvePRandmarketing.com.
Wonderful. Well, as always folks, we will have that link in the show notes, so feel free to check that out. And I do like to remind you we have a video version of the show on YouTube. It is under a channel by the same name — Leadership Powered by Common Sense. Go over there. Check out our archive. We’re rapidly approaching episode 500. Looking forward to that. So we’ll have some news about that when it happens. But for now, I’m going to sign off. Say goodbye. Go out there. Make it a great day.
Meet Our Guest
Jennifer Kaplan is the founder and president of Evolve PR & Marketing, Arizona’s largest public relations firm. Since launching the agency in 2010, she has led Evolve’s growth from a small, client-focused team into a powerhouse of 29 full-time publicists serving more than 140 clients across local and national markets. A proud Phoenix native and Arizona State University alumna, Jennifer’s deep Valley roots and relationship-driven approach have helped her build lasting partnerships and elevate brands across industries. Her leadership and impact have earned her numerous honors, including the Inaugural Hugh Downs School of Human Communication Alumni of the Year Award, ASU Sun Devil 100, Phoenix Business Journal’s 40 Under 40, AZ Business Magazine’s Most Influential Women in Arizona Business, Ranking Arizona #1 PR Agency, AZ Big Media’s Most Admired Companies, Copper Anvil 2025 Agency of the Year, PR News’ 2025 Top Women in PR and People of the Year and Ragan’s Top Women in Communications. Outside the office, Jennifer enjoys time with her family, giving back to the community, and finding balance on her yoga mat. She’s always cheering on the Sun Devils—forks up!
Evolve PR & Marketing website: https://evolveprandmarketing.com/
Evolve – https://www.linkedin.com/company/evolveprandmarketing
Jennifer Kaplan – https://www.linkedin.com/in/jennifer-kaplan-b331948/
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