Kiri Masters (Pt 1): The Challenges of Founding, Building, and Exiting Her Marketing Agency in 7 Years

Kiri Masters Discusses the Challenges of Business Ownership on The Business Owner's Journey Podcast

Kiri Masters is an acclaimed entrepreneur, award-winning writer, and expert in online retail. She founded Bobsled Marketing, a digital marketing agency specializing in retail marketplaces, which she successfully exited in 2022.  Kiri is also a podcast host and personal brand coach.

In this episode of "The Business Owner's Journey," Kiri shares her entrepreneurial journey, discussing how she built and sold Bobsled Marketing, and offers insights into personal branding and the importance of peer groups for business owners.

Her insights are invaluable for any business owner looking to grow their business and develop as a leader. Kiri's emphasis on the importance of a support system, including peer groups and coaches, is a testament to the fact that success in business is not a solo journey. Her approach to balancing work and personal life, especially after becoming a parent, offers practical advice for maintaining mental health and avoiding burnout.

Key Takeaways from the Episode:

The Journey of Building Bobsled Marketing

Kiri discusses the origins of Bobsled Marketing, explaining how her early experiences in e-commerce and banking shaped her entrepreneurial path. She shares the initial struggles, including the challenge of making only $36,000 in the first year and the pivotal decision to leverage her Amazon expertise as a consultant. Kiri emphasizes the importance of content marketing and establishing a strong online presence through blogging and YouTube, which helped Bobsled Marketing gain credibility and attract clients.

The Role of Peer Groups and Coaches in Success

Kiri highlights the critical role of peer groups and coaches in her entrepreneurial journey. She discusses her involvement with communities like the Dynamite Circle and organizations such as EO (Entrepreneurs' Organization) and EOS (Entrepreneurial Operating System). These networks provided her with invaluable support, practical advice, and a platform to share both the highs and lows of business ownership. Kiri underscores how these connections helped her navigate the emotional and mental challenges of entrepreneurship.

Deciding to Sell and Transitioning Out

Kiri reflects on the decision to sell Bobsled Marketing and the complexities involved in the process. She shares the importance of having a strong advisory team, including a fractional CFO and an M&A advisor, to guide her through the sale. Kiri also discusses the personal challenges post-sale, such as managing a change in identity and addressing mental health issues. Her experience offers valuable lessons for business owners considering an exit, highlighting the need for careful planning and support.

Resources Mentioned in This Episode:

Quotes from the Episode:

  • "Content marketing was a crucial strategy in establishing Bobsled's reputation, even when financial resources were limited." - Kiri Masters
  • "The more successful you are, the harder it is for sure. There's less and less people who understand." - Kiri Masters
  • "I prioritized my own health and well-being more than a lot of other founders do." - Kiri Masters

Where to Find Kiri Masters:

How to Get More of Nick Berry and tBOJ

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The host - Nick Berry
The Production Company - FCG

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Episode Transcript:

Nick (00:00)
our listeners are going to get a two for one today because I've got a guest, Kiri Masters, who is going to cover two topics for us. So first is going to be the story of Bobsled Marketing, her company that she built and sold. And then the second, she's going to share her expertise on personal branding. From my conversations with Kiri, she's pretty adept at personal branding and I'm going to have her try to...

speak to that for those of us who are

You made a very good impression on me. You're the kind of person, every time we've had a conversation, it's been, it's like there's something enlightening about it, right? It's just the kind of conversation that I think I've told you this, it's good for your

First thing I wanna do is I wanna start the story of Bob's Lead Marketing. And I'm gonna just kinda turn it over to you and let you run us through the timeline. And I'll probably stop and ask you some questions along the way. But before you start there, I wanna ask you one thing. Would you do it all over again?

Kiri (01:01)

kind of get into it with the story a little bit, but when I started Bobsled, I was 27 years old. And then when I sold that company, I guess I was, yeah, 34. So I think, I was just talking with my husband about this yesterday, like,

think it's great to become an entrepreneur at any stage of life. And statistically, you know, you hear about, we hear, hear about the Mark Zuckerbergs, the 18 year olds starting huge companies, right? But statistically, like there are more entrepreneurs that are 45 and you're more successful if, if you're like just statistically more successful as an entrepreneur when you're older.

But for me personally, having that experience relatively early in life has sort of set me up pretty well. And although it was challenging, I'm really glad that I did it at that point in time because I had a lot of energy. I didn't have anything to lose. Like I didn't have any assets. I didn't have any, like I had, you know, the, the, the beginnings of a career, I guess, in, in banking.

Nick (02:07)
Thanks for watching!

Kiri (02:14)
but I just like, if it all fell apart and nothing came of it, it wouldn't have been the worst thing. I think that that freedom, is, is something that you might miss out as an older entrepreneur, even though you would have much, much more in terms of Rolodex skillsets, managerial capabilities, life experience, industry experience, you sort of make up that gap in, in all of those things.

But I'm still glad that I did it while I was young.

Nick (02:46)
Yeah. So was it your first business?

Kiri (02:48)
No, I started an e -commerce business a couple of years prior to that in 2012, which was this very niche e -commerce business in the arts and crafts supplies category. Basically, it was supplies for you to make your own lamps and lampshades.

So very, very niche. I was like, I was into crafting at that point in time myself. And I had like, tried a little bit of making some lighting and the materials were sort of hard to source. So I decided to set up an online store and sell this stuff myself. So that was where I had actually, dabbled a little bit in e -commerce myself and eventually started selling those products on Amazon. and so when it came time,

for me to sort of drop out of my banking job, which I wasn't really enjoying at the time. I had this skillset around Amazon, which was at the time fairly rare, I guess. And so I was able to take that skillset and sell it as a consultant to brands that were a bit more established and trying to figure out the Amazon ecosystem out back in, this is in 2015.

Nick (04:11)
Okay, and so then went to bobsled.

Kiri (04:14)
That's right. Yeah. So, Bobsled was officially the second company and quickly sort of began to show much more promise than the lamp making suppliers store.

Nick (04:26)
Okay, well, let's hear the story.

Kiri (04:28)
So I had,

the beginning of Bobsled. I was really burnt out from my corporate job. I started out in banking. With the beginnings of my lamp making supplier store, I had a glimmer that I might want to be an entrepreneur. And I was starting to, so I chose to like move into a different job at the bank. It was JP Morgan Chase in New York.

and try and pick a job that was, would allow me to engage more with small businesses and learn more about what it's like to run a small business. So actually becoming a sales, like a business banker, more of a salesperson in the bank was a really good idea. Cause I, I got to do all this training around financial statements and what a healthy cash flowing business looks like and what it meant.

you know, what we would look for at the bank to in terms of cashflow to service dash and things like that. And that was something that that was really unfamiliar to me prior to that. But I really didn't like that job. I, I really sort of felt like a cog in the machine in, in that position. And so I was pretty eager to get out quickly. and that's why I turned to consulting unlike.

an e -commerce business, obviously you can just make money upfront from a consulting engagement versus e -commerce, which is you have to build the whole airplane before you start flying. You have to sink a lot of money into inventory and infrastructure and all of that before you get any dollars back. And typically you get dollars back and then you have to put it right back into more products. And so it's not very, it doesn't cashflow very.

easily, especially in the beginning. So that was the beginning of Bobsled. It was a very rocky start though, that first year. I told someone this the other day, they didn't believe me. In that first year, Bobsled made $36 ,000 and that was like my, you know, we were all living in New York, and it's me and my husband.

He decided to quit his job and join me as well, like towards the end of that year as well. So we were just like living off of fumes in that first year, but it did just kind of seem to hold some promise. It was very exciting. We had a lot of fun working together and just, you know, we're two, like 27 year olds. We'll just figure, if this doesn't work, we'll just figure it out.

Nick (07:09)
That's so awesome. So he saw beyond the $36 ,000 pot of gold. He saw the promise.

Kiri (07:13)
Yeah. Yeah. Well, I mean, that was for the full financial year. So things sort of started to pick up a little bit more towards the end of the year, especially once we were both working on it. But, yeah, it was, it's amazing how you get used to living on a lot more. And that seems like an inconceivable amount of money, but at the time it was, it was all right. We figured it out.

Nick (07:37)
You said it when you started, you were 27 and like you had, you know, you didn't have a lot to lose. You were in a position where you could afford to step out there and do that. And that's what it allows you to do, right? You can get by on 36 ,000 or however many, I mean, that's a chapter in a lot of people's stories, thankfully, right? That's because otherwise there are a lot of us who would never be able to go beyond that. That would be the end.

Kiri (07:49)

Nick (08:06)
Not enough staying power.

Kiri (08:08)

people have it rightly, especially once you have kids and a mortgage and things like that. If you have a side hustle, they're looking to fully replace their income with their side hustle before they make the leap. And I just, I didn't feel that was necessary for me. I just took, took that leap right away. It's all very circumstantial and very dependent on your own capacity for risk.

Nick (08:09)

Kiri (08:36)
as well.

Nick (08:39)
you, you mentioned, I think you use the phrase like it's showed promise, right? This, the bobsled showed promise. So what were the signs? What did, what did you

Kiri (08:42)

Nick (08:48)
When did the light bulb come on for you that this is going to be a thing we need to fan the flames.

Kiri (08:55)
not sure there was one specific moment that I felt really comfortable that it was all going to work out. we had in order to get some momentum with clients, we actually hired a lead gen agency.

who ran this lead gen campaign reaching out to brands who had reached their funding goal on Kickstarter and had raised more than, I think it was like more than like 75 grand or something. And so this lead gen agency would reach out to them and say, hey, we saw that you raised this much money, congratulations. We are a contingency based.

agency that works with brands like yours to get started on Amazon. We only take, we take whatever it was, like 15 % or something of your sales, which for those clients was a great deal because it was a hundred percent risk free for them. and the issue for us was they didn't always pay us or like it was just not a.

After all the fees and everything, we were just not really a priority to get paid. They wouldn't necessarily always like have the inventory available to make good use of the sales momentum that we would work really hard to, to build. So was not a, not a business model I would pursue again, but it did help to show us like, this is a valuable service. People are willing to pay for this.

And we just needed to get some more runs on the board in terms of like the experience that we had and the clients that we worked with in terms of like getting a foundation set. That was, that was really helpful.

Nick (10:53)
Okay. Yeah, that makes sense. So then kind of map it out for me from there to, I believe you said 60 employees, a staff of 60 when you sold and somewhere in multiple seven figures in revenue.

Kiri (11:07)
Yeah, so from the, so seven years later I sold, we, we, so that first year, 2015, it was me and my husband and we had one part -time employee. and then by the time we sold, we had, 60 employees, and around about a hundred clients at that point.

Nick (11:31)
Okay, so how do you get there?

Kiri (11:33)

So what I discovered that worked for me and how we came to know each other as well, Nick, was I didn't have, back in 2015, I had no money, had no credibility, I had no Rolodex, I had like, fairly minimal experience in the service I was selling, frankly. Like I had done it with my own business for a couple of years, it was still pretty small. So I...

You know, I had no business like getting into this whole game. but back then there were not a whole lot of super credible other options either. It was still very much early days in that ecosystem of Amazon agencies, Amazon consultants. They were out there, but there weren't very many of us. so the.

Direction that I took was to lean really heavily into content marketing and building a brand of expertise in this sort of nascent area. So blogging is free. YouTube, making YouTube videos is free. Making online courses is free. And I had time and no money. So that's what I did. And so I had like during my lamp era,

I had also done a lot of content marketing there. I'd make film tutorials and put them on YouTube and still my most, like the, the biggest like YouTube video I've ever made is one of my lamp making tutorials. It's got like 300 ,000 views or something like that. Yeah. I'm surprised you didn't. So I was like, I had some. Come like I had some experience with.

Nick (13:13)
I didn't find that.

in my research, I did not find that.

Kiri (13:25)
content creation from my previous business, which I, it's interesting seeing that thread, like connecting those dots now. but that really, really helped because when people were searching for, I, you know, how to create an inbound shipment to Amazon on Seller Central, like my content would show up. what's the difference between Amazon Seller Central and Amazon Vendor Central? My

content would show up. And so we started to get like, once these Kickstarter clients worked their way through and some of them paid us, some of them didn't, once we were actually able to start generating inbound leads pretty quickly by like within 12 or 12 months really of making a concerted effort there, which at the time felt like forever, but I just, I didn't.

I didn't have anything else to do. I would list, I would do all these sales calls, speak with clients and understand, like try and find out what are their questions? What do they struggle with? What are their misconceptions? Like, what are they, what are they, what are they just wrong about? I mean, we, we, when you're an expert, you know that people have misinformed ideas about something. And so like digging into, digging into that.

commentary about changes, like Amazon would roll out some new program or a fee change or something like that, just jump on that right away. What does this mean? What does it mean for you? Is it good or bad? So that really was the whole engine of Bobsled from 2015 right through to when we sold it. And it meant when it came time to sell and find an acquirer,

It's really funny, all of the potential acquirers I spoke with in 2021 all thought we were way bigger than we were. Like they would get to the point where we showed the financials and like, really? I thought you guys were so much bigger. Like you just seemed like a much bigger company because we had such a big reputation in the space, but we were sort of punching above our weight.

Nick (15:46)
my next question is why did you sell, how did you know it was time? But I don't want to jump to the last chapter of that story if it's not time.

a lesson or

that timeline that we would be skipping over?

Kiri (16:01)
I think one, so it's interesting what I'm working on now. One of the, one of the projects I'm working on now is, is a podcast called Obsession. And it's about people who get to the top of their game, whether that is as an author or as a video game designer, like studying sort of people, people's lives who made it to the top. And there's two, there's two common commonalities with everyone. One is being in the right place at the right time. And two is obsession.

So being in the right place at the right time, you don't always know it. Like I was in the right place at the right time in 2015, having a nascent skillset in the Amazon ecosystem turned out to be, that was like a rocket ship. And even today, the skills are still like relative to the need for them, still quite scarce. So I got in early and demonstrated some expertise and that was.

that w that just ended up being, looking back a very fortunate time and place to get started with that particular skillset. And then obsession is an unreasonable dedication to executing on something or becoming really good at us at a, at a skill or an industry. I've, I studied Mr. Beast, the, the YouTube, the biggest YouTuber in the world. And that guy is like,

He's still in his 20s, but he lives and breathes making videos. Like he just does not stop making videos and he's been doing it since he was like 11. So.

Nick (17:42)
And he doesn't do or doesn't spend time thinking about anything else, right? He's a mutant.

Kiri (17:45)
No, he doesn't have any friends. He doesn't have like, he doesn't have a normal life. This guy is unreasonably obsessed with that. And that's true for pretty much everyone who gets to the top of their game. Now I was like committed to getting really good at this thing. I wanted to, like, I wanted to build a business. I became really interested in, in the...

in the practice of running and operating a business. I got into EOS, which we've talked about. I got into, I joined EO. I really liked talking about business and marketing and it became a big part of my identity. But I also never got to the unreasonable obsession point. Like I always put a pretty good, pretty good line there in terms of.

work life balance and I didn't let the company get in the way of me living a pretty balanced and healthy life. Like there would be tough times, but I wasn't like flying around all the time meeting with clients. I wasn't typically working on the weekends. I had a pretty chill work life.

So I, I think that that if I had been a bit more obsessed and worked harder, it could have been a bigger company and maybe I could have made a little bit more money on the, on the exit. But, that was a choice that, that I made. And in my last like year that I was working at, sorry, in 2019, I was only working four days a week. I would take Fridays off and.

We were living in South America. I was going and learning Spanish and I'd go for a hike and I would work a four day week. So, there is, those are decisions that you can make as well. At the time that I was going through the exit process, I would get that question. Why is bobsled not bigger? Like you seem to have a good position in the market and.

a good team in place and like all of the things that you should, that should make for a, for a bigger business at this stage. And I just think that it was because I prioritized like my, my own health and wellbeing more than a lot of other founders do.

Nick (20:25)
So did you have to, did that come naturally to you or did you kind of hit a boundary early on and find out the hard way that you needed to focus on it? How did you do that? Because that's unusual.

Kiri (20:39)
Yeah. I can't think of a single moment. I had a baby in 2017 and that was, you know, that forces you to step back in, in, in many ways. And I guess I just wasn't really prepared to return to the grind.

Nick (21:05)
Were you pretty balanced before the baby came?

Kiri (21:08)
No, but it was fun then. Like, I mean, this is looking back on with rose tinted glasses, of course, but like on a Friday night, it would be, we would, me and my husband would just be working. I'd like maybe go and get a bottle of wine or something. And we would just like work all night on Friday. And it was fun. We would just, it's not like we didn't have anything better to do, but it was just like the, it was so high energy and exciting that.

Nick (21:26)
Mm -hmm.

Kiri (21:37)
I just wanted to do it all the time. And then Baby comes along, you're like, maybe there's something else to life here than just grinding. So I'd say that probably would be the catalyst.

Nick (21:47)
Mm -hmm.

Yeah, yeah, babies definitely change things.

Kiri (21:53)

Nick (21:55)
as you mentioned EOS and EO, can you like plot those on the timeline for me? Like at what point did you, use those two particular, resources and like, what effect did that have? What was your experience? And are there any others that you have, experience with that you'd kind of put in that same group of like, these were some of the things that, but for me, EOS, we, we use it for a little while. It was, it's.

one of a handful of things that changed everything about the way that I saw my business, right? So that's kind of that group of resources that I'm talking about.

Kiri (22:29)

Yeah. So there was a few things. One, when I first started, I was in this really great online community called the Dynamite Circle. It's still around today. I haven't been a member for a few years, but it is this wonderful community of people who run generally just online location independent businesses, which back in 2012, 20...

13, 14, 15 was still like kind of unusual. but these are all different types of businesses, agencies and e -commerce and things like that. And so I had, there was a really great like part of that community in New York and I would go to some events that they had and there was just this really strong, sense of community there because having an online business was still a little unusual. And so we all kind of like,

really found kindred spirits in each other. And that was, that was awesome. I think that, that there's lots of these communities out there. EO is another one. It's sort of like a more grown up version of, of the dynamite circle, I guess. But there, there are lots of communities out there. And if you can find one that fits your vibe or stage of business, that is that.

is really life -changing because it is incredibly lonely. And once you start building a team, you realize, I, I, these people cannot be my friends and they cannot be my confidants in the business. I need someone to talk with who really understands what I'm going through. And there's, you have crises of confidence where you really don't feel like you've got it in you to do this. And then there are also moments of.

incredible exhilaration and excitement, and you have some kind of win and no one else will understand except another entrepreneur. So you need people to be able to text and share in that journey with you. And I'm still like, I'm still texting and calling and visiting with these friends that I made back in 2013, 2015 today. so yeah,

I've been a member of a couple of different communities there. The EOS was helpful. I did, like many people, self -implement based on the book Traction initially. And that was a really good experience. a number of things I sort of instinctively knew, like the...

integrator and visionary relationship and how important that is for there to be a clear visionary and an integrator. That was something that was already in place and understanding that framework, it's like, okay, actually we got that nailed kind of by accident, but it's still, I'm so glad I don't have to think about like formalizing that now.

Nick (25:54)
Then you can really buy into it, right? You got the information you needed, you can go.

Kiri (25:55)

Yeah. And there's some things you realize, you're like, actually we're doing that pretty well. And it's very, that that's just as good a win as realizing, no, we were doing that all wrong and here's the better way of doing it. you can sort of have an instinct for some of these things and then help, help with the rest. So a system like that, a system like that is, is, is great as well. But I would say I'd put the community.

first because it's as much a mental and emotional game as a game of systems.

Nick (26:32)
Totally. Yeah, I totally agree. As it relates to the community, I think you have to curate your support system as you go. And I think everybody needs a coach. I think you need to be a part of, you need to have a small group of people who are maybe peers, but that know your business well enough that you can talk to them about.

maybe some more of the nuts and bolts type things and they'll understand and they can even push back. And you need to be also be a part of a bigger, broader community. Sometimes it's just to have, make sure that there's somebody around that can pick you up and dust you off and say like, it's going to be fine. Like everybody goes through it, but you're right. It is lonely. And as you go, there are just going to be fewer and fewer people who can relate to the things that keep you up at night.

Kiri (27:17)

Right. Right. Yes, totally. I think the more successful you are, the harder it is for sure. There's, there's less and less people who understand and your employees, you, your employees believe and want to believe that you've not that you're like infallible, but you've got like, you've got a plan and you've got things figured out and that they're safe and secure and that there is a future for them at your company. So you can't let.

Nick (27:30)

Kiri (27:58)
that there is an amount of vulnerability that's helpful to have with your team. So they know that you're a real human and it's a team effort and you need their help. But yeah, you can't just unload on people about all of your insecurities all the time.

Nick (28:17)
Right, right. It's not their responsibility, right? I mean, you may need help. It's not their responsibility to be that type of help.

Kiri (28:20)

Nick (28:26)
Okay. So then now kind of jumping to the, the last chapter with Bob sled. What, what made you decide it's time? How did this, how did that all come together?

Kiri (28:35)

It was a real process to finally decide it was time to sell. I had thought of it for a long time. Because of the space I was in was pretty hot for a number of years. I would have people reaching out, asking about a potential acquisition fairly frequently. So I would entertain some of those calls and...

try that idea on and walk back from it and like, no, I'm not ready to sell. I should really try and get this company bigger and have a bit more of an exciting exit. And I sort of flip -flopped on this for, I want to say like, like at least a year, maybe even a year and a half before I actually decided, no, I'm going to do this. What kind of got me to make that final decision and push ahead?

was playing out my options. I just couldn't see it being a viable option for me to continue to own and operate the company myself. kind of burnt out of it, to be honest. Like, not because I was burning the candle at both ends at that point, but...

the fun had gone for me. I mean, it was working, but the problems that we had just tended to be the same. They were either problems with employees or problems with clients, or just kind of felt a little bit stuck. And so my exit options were going to hire a CEO, which at the stage that I was at would have been

difficult to find someone really good that would be, have it be exciting

maybe not even that. Just I knew it'd be difficult to hire a CEO and not necessarily

one would hit. Like I might need to redo that process a number of times and still stay involved and sort of watch what they're doing and make sure that they're the right person for the job or actually sell the company. So I...

I didn't really like option A because I knew I'd have to stay involved somehow. and so I went ahead with option B and hired an &A advisor who knew my space really well, who was specifically a, like, agency &A broker I'd worked with on the

on the buy side of marketing agencies for a long time and then set up shop on the, on the, on the sell side. So really understood my industry very, very well. And we got moving. This is in the middle of, 2021 when I hired them and we got started.

Nick (31:35)
Did you have an advisor or like who was in your corner when you were going through the thought process? When you started making the decision.

Kiri (31:41)
Yeah. that's a great question. Yeah. So I had a fractional CFO who I'd been working with for maybe two, two, two years at that point, two or three years. foresight CFO is the name of the company. And so I had a fractional CFO that I'd been working with there and was certainly helped with the CFO side of things, but was.

like a coach to me in terms of thinking about this kind of stuff. And, and he, he and I had spoken off and on about selling for a long time at that point. And so when, when things got, got serious, that was very helpful because I'd already been exploring that option with John for a while. yeah. And then I, I had my accountant who I'd been working with since the

Nick (32:33)

Kiri (32:38)
beginning of my company who was also very well versed in, in and A at that point as well. But I didn't have a lawyer. I had to go find the lawyer and and A advisor, out the gate, get that figured out before I got started.

Nick (32:55)
Was your husband still in the business when you told?

Kiri (32:57)
No, once I decided that he, so, so yeah, once I decided I was definitely going to sell, I said, look, I don't think he could like working for someone else. You should, you should leave the company. And just to give a little context, like he was so, we had a conversation very early on when he joined. It's like, okay, so you want to join me here, but like in, in what capacity do you want to be a partner?

Or do you want to, do you not want to be a partner and do you want to just kind of be an employee? And he was, he didn't want to be a partner. He, he just wanted to be on the ride and, but you know, that, that I was the boss and I was going to make the calls. And it was so wonderful speaking of like, who was on my team. He was like the number one on my team because he didn't have like the most important role in the company.

but he knew enough of what was going on and the characters involved. And so he was always a great sounding board to listen to issues or brainstorm ideas and things like that. And I wouldn't always agree with what he said, but if I decided to go in a different direction, he'd say, well, it's your choice. That's your call. So it was a really good, I hear from a lot of people, I could never work with my spouse and...

If you think that, it's probably true. And that doesn't mean that you don't have a great relationship and a great marriage, but I don't think everyone is really suited to work together. And I don't think everyone would be able to like play, make those plays like my husband did to say, here's what I think, but you're the boss, it's your call. And I'm going to support you.

Nick (34:49)
all, did you know that I work with my wife? We're business partners and work together every day. Yeah. So, and, and I, I think before you, I've not met anyone else who talks about it the way that we do. So congratulations. But I think the conversation that you had with him, the role clarity conversation, like it doesn't go the way that you talk about it.

Kiri (34:59)
Yeah, wow, amazing. Yeah, same to you.


Nick (35:13)
it going with him being in the company by accident, right? It went that way because you were willing to have those conversations and, and be honest and push back when it, if you disagreed and then like that was built on and even, working with your spouse aside and that role clarity conversation, that's one of those things that, that I took from EOS. It kind of gave me the method for like, okay.

Kiri (35:16)


Nick (35:40)
I need to get really clear on these things about this place on this, on the org chart here. So now I know we can get clear on our expectations. And so, you know, that's that framework coming into play there and the stakes are the highest when you're trying to apply that with a

Kiri (35:59)
Yeah, absolutely. That's one of the tools I love in EOS the most is that accountability chart.

Nick (36:05)

that, for me, it was like, you know, I have an idea of what we're trying to do here, but I needed some way to organize this. And so, and that's a lot of the resources that I feel like played a big part in my journey were like that. That's, that's what they did for me was they gave me a label or a framework or a methodology, a box to put something in. And that that's just what happened to be.

Kiri (36:21)

Mm -hmm.

Nick (36:33)
most valuable for me or what I needed.

are you taking away from the entire experience with bobsled that you either want to make sure that you do next time or don't do next

Kiri (36:44)
So working with that &A advisor, like I paid them a lot of money, but it was a hundred percent worth it in terms of the moral support. The fact that this is something that they've spent each spent like 30 years of their career doing. And I've never done it before. That expertise is definitely worth something. Yeah. So moral support, just knowing how things work, being a buffer between you and the buyer as well, like having.

Like letting someone else be the bad guy because they were definitely the bad guy. Like this company I sold to said, we did not like your banker. I'm like, well, I don't care. Like he was working for me. I'm the one who paid him. I don't care if he liked him or not, but like he had, he was the bad guy. So that when I joined the company and I've got to go work for the CEO of the company that just acquired me, he's not resentful. He might, he hates, he doesn't like my.

Nick (37:25)

Kiri (37:43)
old broker, they had all these arguments, but like, I, I don't have any, any, any stain on me, you know, so I'm the good, I'm the good guy. So anyway, like it was, it was so worth it to work with a &A advisor and, they were great. I'm still in touch with them. If anyone is in the, marketing agency space, I can certainly like pass, you know, connect them.

Nick (37:52)
Yeah, you're one of the good guys, Hal.

Kiri (38:13)
But, that was really, really important. And then, you know, like everyone says, it takes longer than you think it's going to take. And sure enough, it was, took about eight months from beginning to end. and like, yeah, it was a big journey. I just wrote a blog post actually, that's kind of like childbirth. You have this instant amnesia about how difficult and painful it was.

You think it's going to like just be so you have the birth plan. Of course, nothing ever goes to plan. It takes longer. It's more painful and bloody than like you could have ever imagined. But, eventually it's over and you got to go tell your employees and the clients and things move along. and yeah, I will say it was.

beyond the usual amount of paperwork that you have to deal with for, for, to sell your company. I also had at that point moved back to Australia, cause this is during like just around COVID era, we'd moved back to Australia. So I also had to plan to move back to the States, to go work for this new company, and deal with like an international move in the midst of all that as well. So there was a lot.

a lot going on in terms of paperwork and stress and like starting a job, working for someone else and navigating what, what that's like. And that huge change of identity that comes with, going from being a business owner with the weight of the world on your shoulders, but also ultimate freedom and responsibility of how you spend your time and what you end up working on.

to like having a job and having a boss and having, having milestones to hit. So that was, you know, the, the, the next stage of the, the, the process was, okay, you've done the deal, but it's not over unless you, unless you want to the very.

Nick (40:09)
Mm -hmm.

Kiri (40:23)
Very few people that gets an all cash deal. Like typically there is a next stage required and, and, and another like sprint ahead of you. Once you've, you think you finished the marathon and you got to do the, you know, the, the swimming leg of the triathlon.

Nick (40:40)
And as an entrepreneur, now you have to be re -domesticated for a little while. Right? So how did that go?

Kiri (40:43)
Redemonstrated. Yes. Yes. Yeah. Yeah, mixed. So like I had a wonderful boss and the company that I sold to was, was really great and did everything they said they would. so really no, no complaints there. It was, that was all wonderful.

The turmoil that I faced was all in a turmoil and it was related to a change of identity, getting through something that was so like, look at the time during the exit process, during the &A process, it was just like, it was just one data time, just put one foot in front of another. They need this, they need that. This has come up. What are you going to do about that? And just like, and then.

So it was, I couldn't really think about anything else. It was all, all consuming real is just get the thing done. Then when it was done, tell everyone, start the process of move, like these are, and moving back to the States and like event. It was, it was like a year where it was all about the deal or all about the move. And then, you know,

Nick (41:49)
Mm -hmm.

Kiri (42:10)
July, August of 2022, most of the things on the to -do list were done. And I was like, who am I? And what am I? What? Yeah, it was, I finally had some time to like myself and it was, it was.

It was nice like not having to work until midnight every night being on a different time zone and everything. But suddenly I had some time and space and I was like, I was really confronted with.

darkness. And this is something that entrepreneurs face when they sell their company and there's, I wish I could pull this research up, but I found a research study of people who'd exited their companies and like, it was like something crazy, like seven or eight out of 10 people who'd exited their businesses suffer from clinical depression.

Nick (43:13)
I would believe that.

Kiri (43:15)
Hmm. So that's what, you know, eventually came to realize that I, I, I was depressed and I started going to the psychiatrist and therapy for that. And, on my mental health journey from there, but that was very, it was very confronting. I felt very guilty that I had everything I could want out of life. I had a great family, great marriage.

I had money in the bank, I had a great job. What the

you don't deserve to be depressed. You've got everything.

Nick (43:53)

Kiri (43:56)
I also had a lot of judgment about depression as well, like, you're lazy, you're like - you're on the couch all day, you can't get up and do anything. You're lazy, you don't deserve it.

So I had my own judgment about what that mental health challenge looked like and I didn't like that. I had a lot of judgment towards myself about it.

Nick (44:19)

so you just kind of figured out on your own that, you know, this is what I'm going through. I need to talk to somebody. Is there something that you could, you could have been told or that you could tell other entrepreneurs who might come up on that situation? Like, what do you need to look for? How do you keep somebody from having to figure, find out that that's what they're dealing with the hard way?

Kiri (44:41)

Hmm. Yeah, that's a good question. I

it became pretty obvious to me over time that that was the issue. It was sort of come and go, which made it difficult because I would have some bad days and then I'd feel all right. I'm like, that's weird. The other day, I don't know what it was. Maybe I didn't sleep well or something. I'd shake it off.

And then we'll come back and just kept recurrent. It was just kind of so I would say that to be aware of how prevalent it is and, and, and maybe after the interview today, Nick, I'll, I'll find that research and send it to you so you can put it in the show notes, but it is very profound. The percentage of people who struggle with this and to

just to be aware of it and to make your loved ones aware of it as well. Yeah, like if you, maybe I'm not the one that notices that first, but just to share with your loved ones that, hey, this is, it sounds strange because I've just had this like otherwise amazing event, but like a lot of people in my position do actually end up getting depressed. So just like,

Nick (45:42)
There's anything you can do to be proactive, right?

Kiri (46:05)
you know, have someone else looking out for you as well, because you may not even be noticing the one to notice it first.

Nick (46:13)
Yeah, definitely. We'll for sure include that information in the show

fire rekindled?

Kiri (46:21)
so I worked for the acquirer for a couple of years after the transaction and

once my obligations were finished there, I decided I wanted to leave. I have been in this space for nine years now and never say never, but I just got kind of sick of talking about the same things. It's an exciting industry. I went to a conference a few months ago just before I left and it's an exciting industry. I think...

Nick (46:47)
Mm -hmm.

Kiri (47:01)
you know, that there's a lot going on, never say never about going back to it, but I just, I felt kind of burnt out. I really wanted to have a break. So what I've been getting up to since I've left is doing a little bit of coaching and mentoring specifically in the personal branding and thought leadership space. As we talked about, I started a new podcast as well called Obsession, which is not an interview podcast, but it is.

exploring the origin stories of people who made it to the top of their game in commerce and culture. And what sort of, you know, what were the attributes that got them there? What are the habits, things like obsession and being in the right time and place as well. And just sort of like going back in and documenting my journey, I really learned a lot from people who'd come before me and shared.

what it was like to sell their company and what it was like when they first started their company and listening to podcasts and audio books and things like that about how other founders had made their way. And so I kind of feel like I'm in this point of time now where I can be a little reflective and go back and try and like document that story for my own benefit of like just processing it myself, as well as.

other people who are just starting out or just going into that exit transition process and want to understand what it was like from someone else. I'm just sort of writing all that stuff down in a personal sub stack as well.

Nick (48:44)
Yeah. So I've enjoyed reading the Substack. I've learned, I mean, a lot more about you and it's kind of sparked. Those are things that have come up in our conversations I think the podcast as I got into it and started to understand more about what it is, is very interesting to me. More interesting than I think you let on because it's like, you know, what makes these people who get to the

Kiri (48:55)

Nick (49:11)
and for somebody who thinks about, well, how do you, how do I want to be? How do, how do you need to be to be, to perform at that you know, a window that you like to look in into and see, you know, how are other, what, what's their style? How are they doing it? What's behind it? What's, you know, it gives you something to maybe use as a

Kiri (49:21)

Nick (49:30)
But I think the obsession podcast is very cool. I've seen a few episodes of would like to have you talk a little bit about, share some of your expertise on personal branding. This is actually how I got to know Kiri is I reached out to her for some input and she, we've had a couple of conversations.

And she's had to kind of slap me around a little bit about maybe some of the beliefs that I have about personal

I'm not sure if I'm representative of most people, but I feel, I think that me getting in my own way is probably something that it to other business tell us what do we do wrong and what should we be doing?

Nick Berry Round Headshot

Nick Berry is an accomplished entrepreneur and CEO, whose track record includes founding and leading numerous companies since 2002.

He is also a mentor and coach to other entrepreneurs and business owners who are looking for a trusted (and proven) advisor.  

Among peers, colleagues, staff, and clients, Nick has been referred to as both 'The Business Guy' as well as 'The Anti-Guru', due to his pragmatic approach and principled leadership.

He shares his insights and lessons learned, along with those of his expert guests,
on his podcast, 'The Business Owner's Journey'.