Connor Tomkies. Aftermath of an Exit: Healing, Reflecting, and Progressing Forward
Episode - 21
Connor Tomkies. Aftermath of an Exit: Healing, Reflecting, and Progressing Forward
Connor Tomkies. He spent 8 years growing and selling SupportNinja, his global talent acquisition firm. Now he focuses on buying great businesses to scale them for exit. This episode delves into Connor’s exit experience, why he prefers to buy a significant portion of a business over angel investing, and how helping out his extended family members turned out to be the most rewarding use of his exit wealth.
What We Discussed:
00:01:12: Welcome
00:01:25: Discussing Connor's sale of Support Ninja
00:02:34: The experience of selling a company
00:03:11: Separating Connor's business decisions
00:03:40: The importance of discussing the future with partners
00:04:06: The traumatic experience of building a business
00:05:22: Post-exit healing process
00:06:12: Dealing with transition
00:08:17: Deciding on a time frame to take a break
00:08:52: Current happiness with decisions
00:10:10: Introduction to venture studio, Operator Equity
00:11:16: Discussing goals for buying businesses
00:12:01: Introduction to Entrepreneurial Operating System (EOS)
00:13:04: Providing value to entrepreneurs
00:15:14: Enjoying the entrepreneurial stages
00:18:11: Personal love for inception and growth of a company
00:19:33: Buying companies in the growth stage
00:20:11: Exercising creativity with new projects
00:21:10: Beginning of Operator Equity journey
00:21:57: Dealing With The Identity Crisis After Business Exit
00:26:10: Changing Perceptions about Money and Wealth
00:31:13: Balancing Personal Relationships Post-Business Exit
00:33:39: Redefining Purpose After Business Sale
00:39:52: Evaluating Financial Success and its Impacts
00:41:23: Encountering and Dealing with Impostor Syndrome
00:43:22: How Parents Define Success
00:44:23: Thoughts on Raising Future Kids
00:45:35: Discussing Operator Equity and Investing
00:47:24: Work-life Balance and Fulfilment
00:48:42: How to Be Remembered and Leaving a Legacy
00:49:47: Closing Remarks and Good Wishes
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Connor Tomkies: [00:00:00 - 00:00:03]
I was a little worried about how I would respond to wealth.
Anastasia Koroleva: [00:00:04 - 00:00:29]
Connor Tomkes. He spent eight years growing and selling support Ninja, his global talent acquisition firm. Now he focuses on buying great businesses to scale them for exit. This episode delves into Konas exit experience, why he prefers to buy significant portion of a business over angel investing, and how helping out his extended family members turned out to be the most rewarding use of his exit Twelve.
Connor Tomkies: [00:00:29 - 00:01:06]
The best companies have multiple offers to buy them. Like, the best companies have options. So then the question is, how are you providing value to those entrepreneurs? I look for companies that already have a fully built leadership team and have already found product market fit, and I'm just helping them scale faster. I think the best things that we've done with money have been helping family members.
But it's also, like, something that you hear a lot of, like, caution about. Feeling embarrassed about your past self, but also feeling like you're an imposter. Like, all these things are probably signs of growth. If I was to die tomorrow, I think I have lived a good life, and I don't have many regrets at the moment.
So I'm pretty happy with how things are.
Anastasia Koroleva: [00:01:12 - 00:01:13]
Hi, Corner.
Connor Tomkies: [00:01:13 - 00:01:15]
Hi, Anastasia. Nice to meet you.
Anastasia Koroleva: [00:01:15 - 00:01:20]
Nice to meet you, too. Very good to have you on my podcast. Thank you for joining.
Connor Tomkies: [00:01:20 - 00:01:24]
I'm excited to be here. The Exit Paradox. Let's jump into it.
Anastasia Koroleva: [00:01:25 - 00:01:36]
Fantastic. So you sold your company support Ninja two years ago. Can I take you back to that moment when you made the decision? And I want to hear why you decided to sell.
Connor Tomkies: [00:01:37 - 00:02:24]
Yeah. So, for everyone, I think the reason is slightly different for us we were hitting a point where we were hitting a lot of ceilings as far as, like, our growth, and the operations were getting so much bigger, and support Ninja was doubling in size every year, and so as a different company every year, and I had to be a different CEO every year. So that was a part of it, is that we needed a partner to help us scale to that next stage. And then another piece of it is there was three partners, and one of the partners wasn't involved in the business day to day. And so going through that exit process was a way for us to also have that partner find his exit and give him an option. And that's something that's always really challenging, is that the partners that you have going into it might not be the next set of partners that might help you get to the next stage.
Anastasia Koroleva: [00:02:24 - 00:02:33]
No. Absolutely. So now, looking back to that business that you saw, do you ever regret starting it in the first place?
Connor Tomkies: [00:02:34 - 00:03:00]
I don't think I do. Even the companies that didn't have the exit, I hoped that they would have. It's hard to say that you regret it if you like where you are currently. For me, it's like, even if you don't have that desired outcome financially, you still learn so much going along that journey, and you still met so many different people that help you get to where you are that it's hard to say that you regret that. Right.
Connor Tomkies: [00:03:00 - 00:03:08]
And so would I have done things the same way? Probably not, but hard to say that I regret it.
Anastasia Koroleva: [00:03:08 - 00:03:11]
What would you do differently this time?
Connor Tomkies: [00:03:11 - 00:03:39]
So I kind of have to separate it out into two different parts. Right. So the first part is like, what would I do differently if I was to sell a company in the position that I am in now, which is a little bit different, because once you have that financial security and you've gone through that exit process the first time, you're able to have more flexibility, you're able to time your exit better, you're able to plan better. And so that's completely different. And that's why I encourage people to, like, go through that process once, because then you're a different entrepreneur after that first time.
Connor Tomkies: [00:03:40 - 00:04:01]
Um, but if I was to go back and do it before, I think it's important for partners to, uh, kind of sit down and talk about what that entrepreneurship prenup looks like if you were to split up as partners, or what happens if someone finds something more interesting, um, and they want to do something else. I think having that conversation is very important, and I do that with all my partners I work with now.
Anastasia Koroleva: [00:04:01 - 00:04:06]
Would you agree that building a business is a traumatic experience for a founder?
Connor Tomkies: [00:04:06 - 00:05:06]
Yeah, it can be traumatic. I think all of us have some scar tissue. Yeah, for sure. I think it's hard because there's so much energy and so much of yourself that you put into that business. And so if that business goes through something, then you're so tied to it that you, in a way, also go through it. And so it's also hard to have that much responsibility or be that responsible for so many people. And if your company gets to a size where you don't know everyone by name, there's also that kind of, like, you're responsible for people that you can't directly take care of. And that's kind of stressful in a way. So I think a lot of the trauma is either tied to not being able to be the person I want to be for everyone inside the organization, if that makes sense. But I also am not sure if it's fair to call it trauma. I think it's just more like some scar tissue, you know, like, take some hits, and then you keep on moving.
Anastasia Koroleva: [00:05:06 - 00:05:22]
I guess that's where scars normally come from, from some form of damage. Right. The reason I was curious about it is because I wonder if you then went through any kind of healing process after you sold and if you felt the need to do that.
Connor Tomkies: [00:05:22 - 00:06:12]
So whenever I talked to other post exit founders, a lot of them took some time off in between their companies to take time to reflect. And I've heard different amounts of time kind of tossed out there, like a couple months, two years. I didn't take that time to, like, reflect too much. I think I was kind of dealing with my stuff and my transition while moving, and I think that's how I tried to feel better is almost immediately, I started building landing pages and working with potential partners, and I spun up, like, a venture studio, and people reached out to me to invest or buy their business. And so it was just more like I was excited about what the next idea was, and I was excited to keep on moving.
Connor Tomkies: [00:06:12 - 00:06:31]
But probably for six or eight months, it's been like, transition, where I'm like, have good days and then bad days, or I wake up in the middle of the night being like, oh, I should have done this, or I should have handled this relationship differently. So I think I'm still dealing with it, but I'm probably like, elsa, I'm frozen, and I'm concealing, not feeling.
Anastasia Koroleva: [00:06:31 - 00:06:39]
So if you look back at these two years, what would you do differently if you had to go through them again?
Connor Tomkies: [00:06:39 - 00:08:07]
I probably would have taken a little bit more time. I think that probably would have been best. We went on a trip to Italy, and we were able to relax there. And then we came back, and my wife kind of I was playing Zelda on the couch behind me, and she's like, is that what you're gonna be doing? And I'm like, oh, yeah. Well, I guess not. I should get to work. So I wish I'd probably take a little bit more time. And I kind of respond well to that. I kind of respond well to people, like, teasing me or kind of pushing me to do something a little bit differently. And so I wish I probably took a little bit more time than that, though. And I think this is hard, but whenever you're transitioning away from the business, like, the thing that you carry away from that experience most is the relationships that you have inside that business.
And I wish that I did this to an extent, and I wish I did this even more, is I wish I connected more with people and spent more time with them and was able to, like, it's never too late, right? But it's. I wish I was. It's important to be a very intentional friend and peer and colleague to the people if you're leaving a business because you might work with them again or you might. Those relationships are very important, you know?
Anastasia Koroleva: [00:08:07 - 00:08:15]
So you regret you didn't take more time between businesses because you could have spent that time developing those relationships.
Connor Tomkies: [00:08:15 - 00:08:17]
Yes, I think that's exactly it.
Anastasia Koroleva: [00:08:17 - 00:08:19]
How much time you think you should have taken?
Connor Tomkies: [00:08:19 - 00:08:50]
I think for me, probably a couple months would have been good. And that's on the lower end of the spectrum, I think. I think we have a knee jerk reaction of, we have to move, or we have to be building something, or if you're not moving, you're standing still. And sometimes it's good to strategically hold still. It's good to strategically stop and take a moment, or else he might jump into the wrong thing, and he might be in that wrong thing for the next three to eight years. So it's good to take that pause.
Anastasia Koroleva: [00:08:50 - 00:08:52]
Do you feel now you're in the wrong thing?
Connor Tomkies: [00:08:52 - 00:10:08]
I think I was relatively lucky in that I have a lot of partners that I really respect and enjoy working with, and I actually enjoyed what I'm doing now more than I was, like, two years ago. And so I really enjoy that piece. I really enjoy working in multiple businesses. I really enjoy seeing them grow and develop and expanding on different ideas relatively quickly. And it's harder if you're working inside a bigger company and support Ninja had thousands of employees. It's really hard to move quickly. And also, you feel guilty working on new ideas because you feel like you should be working on, you need to be working on that company 100% like they, you owe them that much. Right, as the CEO of that company. And so I do enjoy the freedom of where I'm at now. I don't have a lot of regrets. I think that there were a couple things where, like, things didn't work out right away, or you try to do, like, you're looking at a distrust business and you're trying to figure out how do you pivot it. And luckily enough, we made some mistakes, but we were able to move on relatively quickly. So that's a win.
Anastasia Koroleva: [00:10:08 - 00:10:10]
So what is it that you're doing now?
Connor Tomkies: [00:10:10 - 00:11:15]
So I started a venture studio called Operator Equity, which the idea is almost like an anti-private equity firm, where it's entrepreneurs are essentially the LP's in the business. There's not a horizon as to when you have to sell. And I focus mostly on fixing cap table issues. So what I was talking about before, helping partners try to figure out what is the right next steps for them, and then operator equity is in a position to help those companies kind of like fix that cap table or figure out what the right steps are to move forward. And so I did that.
I became an EOS implementer, if you know, the entrepreneur operating system. So that way, whenever I buy a business, I can help implement an operating system inside that business and help them grow their sales and their operations departments. And right now, operator equity has six logos underneath the umbrella. So it's been growing pretty rapidly. We just announced that we bought a business today, which is exciting.
Connor Tomkies: [00:11:16 - 00:12:01]
We set out to make essentially like a deal box, talking about like, what are the type of companies that we're interested in buying, what are the characteristics of them? And so, as far as valuation, we're looking at between five to 20 million. We find this kind of like the in between of like small to medium sized enterprises, like, where they're just kind of hitting their, their growth stage. 25% margin agency SaaS Technology services businesses mostly, we're looking for a motivated founding team, probably at two to six times on EBITDA, and preferably an EOS operating system behind the scenes. So, like, investing in other companies that also run on this operating system makes it easier to speak the same language and to incorporate them into the fold.
Connor Tomkies: [00:12:01 - 00:12:47]
So, essentially, EOS stands for the entrepreneurial operating system. It's based off this book by Gino Wickman called Traction. And it breaks down the business into six key components. There's a people component, a data component, process, vision, traction. And it breaks down, like, here's the different stages of development in these six different areas, and here's how you can implement them in a very clear and concise way. And I think for a lot of entrepreneurs, we just start solving problems, and we don't necessarily know what that next stage of development looks like. And so I like the EOS model. Just because you can hand someone a book, you can hand a manager a book, or an entrepreneur a book, and you can know that you're beginning to speak the same language, essentially.
Anastasia Koroleva: [00:12:47 - 00:12:55]
Yeah. It's like The Lean startup book was used for a while in a similar manner.
Connor Tomkies: [00:12:55 - 00:13:02]
I think that might have been one of the first books I read on entrepreneurship back in the day. Is that Eric Ries that did that book?
Anastasia Koroleva: [00:13:02 - 00:13:03]
Yeah, I think so.
Connor Tomkies: [00:13:03 - 00:13:04]
It's been a while. Yeah. Eric Ries.
Anastasia Koroleva: [00:13:04 - 00:13:11]
Why did you choose EOS as kind of the structure for your system?
Connor Tomkies: [00:13:11 - 00:14:22]
Yeah, so I self implemented EOS at Embark, which is a dog genetics company, before support Ninja, and it went all right. And then at support Ninja, we needed a little bit more help because we had so many people. So we had three EOS implementers, some even in different countries, and we implemented it because we had so many managers, so many different levels, because we had so many people. And it was that point of being able to hand them that two page business plan and have everyone aligned in core values and everyone understand what our one, three and ten year plan would be and what our good market strategy is. Just being able to hand them that plan in a clear and concise way and have them run their meetings the same way, really created a really cool ecosystem where everyone inside the company could see what was happening on a leadership team level and a director and a VP level. It's really kind of cool. Like, if you look at 150 different teams with team managers all doing meetings the same way and speaking the same language and understanding where the company's goals are, that's a pretty powerful alignment thing.
Anastasia Koroleva: [00:14:22 - 00:14:46]
So basically, you tried it yourself, you saw it work in two companies, not even one of different sizes, and now you believe in a system because you've tried it and you think this is sort of the value you can bring into those companies that you're buying to help them. Ten X or whatever your expectation is from them by the time you, I assume, exit them at some point.
Connor Tomkies: [00:14:46 - 00:15:13]
Yeah, I think that's a big part of it, is whenever people are the best companies, have multiple offers to buy them. Like the best companies have options. So then the question is, how are you providing value to those entrepreneurs? And that was something I was struggling with, and that's what I liked about EOS. But then the other side of it is that I think CEO's and entrepreneurs are also looking for what their growth plan is as a individual, as a person.
Connor Tomkies: [00:15:14 - 00:15:52]
And what's cool about operator equity is that once we invest in a business and they haven't, they have an event, they have like a lot of cash that they didn't normally have access to, they then get to act as an LP in the next deal. So then if they find something that's interesting to them, then they can co invest and do the next one. And so in a way, they're growing as an entrepreneur and they're getting more exposure into different industries. And I think that's pretty important to me, is that they're bringing in that skillset into that ecosystem and they're helping engage with other founders that are going through similar things. It creates a really cool dynamic.
Anastasia Koroleva: [00:15:52 - 00:15:56]
So what's your ambition with operator equity? Where do you want it to go?
Connor Tomkies: [00:15:56 - 00:17:05]
I think for me, I like the idea of entrepreneurs helping entrepreneurs, and the idea of not having a shorter term investment horizon. I like the idea of kind of seeing what nature the company takes on its own. Right? Like, what's the best thing for that company and for that entity? Is it scaling for five years and then selling? Or is it scaling for 20 years? Is it doing an ESOP? Is it doing a public offering? I enjoy seeing that kind of piece, you know, and there's not like a hard requirement as far as, like, we have to hit these milestones or we have to acquire these companies within this timeframe. So I really enjoy that there's a little bit more flexibility kind of baked into the model where with traditional financing options and raising money from LP's, they need to set an expectation as to when that exit is going to occur. And usually it's within that three to five year window, and that might not necessarily be the right thing for the company. So from my end, I'm looking forward to seeing how these companies flourish organically.
Anastasia Koroleva: [00:17:05 - 00:17:15]
So on a personal level, how did you come up with this idea, as opposed to building another company, just one company, or doing something else entirely?
Connor Tomkies: [00:17:15 - 00:17:58]
I think there's a difference in mindset between being a director and an executive, and being an executive and a founder. And then logically, the next step is being a founder versus an investor. And so for me, I was like, what is the type of investment I could be the most excited about? And how can I amplify myself similar to how I amplify myself as a CEO or as a founder? You hire people in a kind of like a family office venture studio model.
You are amplifying yourself, but on another level, you're amplifying yourself on an organizational level, and you're working with multiple organizations at the same time. And I think that's pretty powerful.
Anastasia Koroleva: [00:17:58 - 00:18:11]
So when you worked on your own companies that you founded or co-founded, what it is that you love doing, what kind of activity you love doing most?
Connor Tomkies: [00:18:11 - 00:19:20]
So have you heard that Zero to One Peter Thiel kind of book where it's talking about the joy of that initial creation element? So if there's Zero to One, and then let's say one to two is like the mid stage, right? And then let's say two to three is like a scale. I tend to enjoy zero to one, which is like the inception of the idea, the creation of the initial team and then the launch and then one to two I don't enjoy so much. That's like the small to medium sized enterprises where you're scaling, but you don't have all the team and all the resources in place. And I'm like, yeah, that's not great. And then I really enjoy the two to three. So you have a built out leadership team. So there's a little bit of a gap in the middle that I don't particularly enjoy. And so I really enjoy the startup ideation and launch, that creation of something. Then I enjoy seeing that thing hit the growth stage or hit that scaling element, which is more sales and marketing oriented.
Anastasia Koroleva: [00:19:20 - 00:19:26]
So sales and marketing is what would be interesting for you in that two to three stage?
Connor Tomkies: [00:19:27 - 00:19:27]
Yeah, for sure.
Anastasia Koroleva: [00:19:28 - 00:19:33]
So when you buy companies, do you buy them when they are already in that third stage?
Connor Tomkies: [00:19:33 - 00:19:36]
Exactly, yeah.
Anastasia Koroleva: [00:19:36 - 00:19:37]
You look for a more interesting one as soon as possible.
Connor Tomkies: [00:19:37 - 00:20:11]
Yeah, it's been interesting. So some of the companies that I'm actually working on, companies inside this family office, inside this venture studio that are incepted and launched inside the ecosystem, but the companies that I'm acquiring right now have gone through that scaling challenge and has found that product market fit and are in that quote unquote two to three. They're in that growth stage. I look for companies that already have a fully built leadership team and have already found product market fit and I'm just helping them scale faster.
Anastasia Koroleva: [00:20:11 - 00:20:33]
So do you feel you may be missing that creative channel that your business was for you probably at the very early stage if you only focus for the foreseeable future on companies that are more mature?
Connor Tomkies: [00:20:33 - 00:21:10]
Yes and no. I think that. So for example, I'm launching a podcast and that's one of the things that we were talking about. Right. And so that idea of like how do you, what's the premise behind it and how are you providing value to the listener and what's going to be the name of the podcast?
And so I get to exercise creativity in that way. And I'm learning so much because I'm immersing myself in these different companies and we're also launching additional services and products. I don't feel like I'm limited on the creativity side. I feel like I'm actually able to be more creative, if that makes sense, and solve more problems that are more varied.
Anastasia Koroleva: [00:21:10 - 00:21:18]
Fantastic. For how long you've been doing it now your operator equity business.
Connor Tomkies: [00:21:18 - 00:21:34]
I sold support Ninja two years ago. I stepped down as CEO of support Ninja in July to join the board. And then I've been working on this for less than a year. So it's been a relatively tight timeframe and a lot happening pretty quickly.
Anastasia Koroleva: [00:21:35 - 00:21:47]
I'd love to talk to you in five years or six years to see how this idea develops, but it sounds like it ticks all the boxes for what you think you want to do in this next.
Connor Tomkies: [00:21:47 - 00:21:54]
Let's check in. In five years, I might be like, Anastasia. I don't know what I was doing. I am losing my mind. I don't know what meeting I'm entering into.
Anastasia Koroleva: [00:21:54 - 00:21:55]
Fine. Right.
Connor Tomkies: [00:21:55 - 00:21:56]
I'm sure you.
Anastasia Koroleva: [00:21:57 - 00:22:15]
That's it. Or maybe you'll be very grateful that you started it. So I would be continuing on your personal journey. How you dealt with the loss of identity after you sold support Ninja.
Connor Tomkies: [00:22:15 - 00:23:40]
I think it's a little hard. Whenever you look at, there's a little bit of an ego and it's not always healthy where it's like, like with support Ninja, there's thousands of people involved and they all help make that company. Right. And everyone has their fingerprint on it. And it's hard to sometimes look at things that might have, like, your fingerprint on it and see it take on like it go in a different direction. And that's a little hard to see, right. Either you are growing a certain way and then you're no longer growing a certain way or see things being done differently, and that's a little challenging. The hard part, though, is that nothing really lasts and that it's almost like you're building a sandcastle. But everyone knows that your sandcastle is going to be washed away whenever the tide comes. So if nothing lasts, then it's like the only thing that you have is that time that you had with that company.
And I think that we made something pretty cool and we made a good environment for the employees, and we did a lot of good for the community. And it's really cool to see. It's something that, on the flip side, it's really cool to see something that you help make and see it flourish and see it do something that you never thought it could. So to answer your question, I'm still navigating it.
Anastasia Koroleva: [00:23:42 - 00:24:33]
Yeah. I guess what I was trying to understand is how much that search for a new and clear identity was important in your decision about what you were doing next. So, for example, for me, when I sold my company, I was like, oh, my God, I need to have some kind of name or title or identity attached to me. And the first one I found was angel investor. And I went ahead and invested in a bunch of companies just to understand years later that it was coming from a completely wrong place, that I didn't do my work properly and I just wanted to be someone in the ecosystem because I felt I was suddenly kind of kicked out of it.
So I was just curious if you can relate to that or you didn't have as much ego as I did at the time.
Connor Tomkies: [00:24:33 - 00:26:10]
No, I think I have it bad. I think that it's kind of like that dinner party question when people ask you, what do you do, right? Which is inevitably, like the first or second question. And for almost everyone, it's like your work, right? It's your title or the company that you made.
And then after an exit, you're like, well, what's that answer? For me, it's not as clear cut, it's not as clean. And in some ways, I think that is a wrong question to begin with. Right. Because, like, that's same thing is like, people are trying to figure out how you fit into their world and you want to understand how you fit in their world, right.
And so, yeah, I definitely struggled with that. And there's this, there's this guy that was interviewing people during, like, Woodstock, and he was asking a guy like, so what do you do? He's like, I'm just living, man. And I'm like, oh, I can relate to that. I'm like, I'm spending time with family and with friends and, like, my title isn't all that I am.
But on the other hand, I was very quick to be like, I'm going to be launching these different things and I'm going to be running these different companies. And I still don't know. What I say whenever I'm at dinner parties is do I talk about one of the companies that I'm working on, or do I talk about the podcast that I'm launching, or do I talk about this community that I'm trying to build for entrepreneurs? It's very different, and I don't know what the right answer is. So maybe I should just pick a different answer every time.
Anastasia Koroleva: [00:26:10 - 00:26:22]
I guess you'll come up with some formula over time. So how your thoughts about money and wealth changed from before you exited your business to now?
Connor Tomkies: [00:26:23 - 00:27:28]
I was a little worried about how I would respond to wealth, and so I took some chips off the table. I took some cash out of the company when it probably would have been better to keep it all in. Right. Because it's. It's growing fast, partially, so I could learn about money.
So I definitely kind of view it a little bit more as, like, an educational process, and I'm definitely learning, like, what things I enjoy and which things I don't. I think it's definitely helpful to work with other people that have sold their business that are navigating the same thing, so that way you guys can share some lessons learned. That's definitely been helpful for me. Yeah. As far as money is concerned, I think I have a bias towards things I can control versus things I cannot control.
So I would much rather have, like, a company where I own a meaningful stake and versus a angel investment where I don't have as much of a clear image. What was that answer for you?
Anastasia Koroleva: [00:27:29 - 00:28:50]
It took me years to understand what wealth actually meant for me. There was a lot of confusion. I made lots of mistakes. And I think it wasn't until I got some clarity about my purpose when I realized that I want to think about my wealth as leverage for my purpose, in addition to creating enough stability in my life so I can actually be free to do what I want to do, which is also related to my purpose. But that was a long journey. At first, there was a lot of shock. There was a lot of fear as well, because I didn't come from much money. And when I did get the money, I suddenly developed very quickly this anxiety about my incompetence. And when I started angel investing, that didn't help because I ended up losing quite a lot of money. Didn't do very well there, and I didn't enjoy dealing with all sorts of advisors and private bankers either.
So it was quite bumpy for me. It was also very sudden, like, I didn't have any money then. I had too much to be able to manage, so it was a bit painful. Hence my question. I'm very curious about how other people go through this.
Connor Tomkies: [00:28:52 - 00:29:51]
The night of the first exit, my wife and I were about to go to bed, and my wife, in the span of ten minutes, figured out how to spend all the money that we had made. She's like, we're sending this much to family members. We're doing this much to here. I was like, it took eight or ten years, and in ten minutes it was all figured out. And, yeah, I think it's funny because everyone has an interesting relationship with money and understanding how to going from an abundance mindset versus a scarcity mindset and an offensive kind of, like I say, offensive, as, unlike you're looking at how do you generate wealth versus defensive.
Whether you're looking at how do you protect very different kind of mindsets.
Anastasia Koroleva: [00:29:51 - 00:30:08]
You are talking about an abundance mindset. I found that it was much easier for me to have it when I didn't have money. It was much harder when I did. It should be the other way around, but it's very easy to accept it when it's just theoretical and you have nothing to defend.
Connor Tomkies: [00:30:08 - 00:31:13]
Oh, for sure. 100%. And I think the best things that we've done with money have been helping family members, if that makes sense. But it's also, like, something that you hear a lot of, like, caution about, which is kind of interesting in that, like, you can hear about, like, money messing up families and relationships and trusts and that have gone wrong. But on the other hand, if you're able to, like, help your grandparents or your parents with, like, health issues or help family members move in with other family members or help with a down payment on, like, a house, like, those things have a pretty big, like, lasting impact on your lifestyle and your family. And, like, helping kind of set the course. So I think that's something that, like, we're happy that we've done with the financial security is be able to extend that financial security safety net to more people, which is helpful. But on the other hand, you also hear a lot of stories of caution about that that I haven't yet experienced.
Anastasia Koroleva: [00:31:13 - 00:31:33]
Yeah, I think it's one of the most common questions, actually, that come up when you talk to people who exited businesses or came into wealth recently. How do you say no to people with whom you don't want to hurt their relationships with? It's not easy.
Connor Tomkies: [00:31:33 - 00:31:48]
Yeah, I don't have the answers on this one at all. I think, similar to you, I want to figure out how to provide financial stability and then align money and purpose as much as possible. And I'm still navigating that.
Anastasia Koroleva: [00:31:48 - 00:31:52]
So your wife immediately knew how to spend the money.
Connor Tomkies: [00:31:52 - 00:31:53]
She has a gift.
Anastasia Koroleva: [00:31:54 - 00:31:59]
Did you two agree on the plan? It caused some disagreements in the family.
Connor Tomkies: [00:32:00 - 00:32:47]
No. And I say this lightly because, like, she had all of it allocated it, and none of it was in, like, it was almost mostly, like, the family members. Like.
Like, 10% to each family member or something like that. And. But, like, whenever we talked about it, we talked about, like, long term appreciating assets and different investment things. And, like, also, that's, like, if I want to buy companies or do other things, like, that's kind of like you're doing it from what you made in a previous sale. And so she probably had it allocated in ten minutes, and then we probably walked it back in ten minutes.
So it wasn't, it wasn't. It was a healthy discussion.
Anastasia Koroleva: [00:32:47 - 00:32:52]
Generally would you say your exit had some impact on your marriage?
Connor Tomkies: [00:32:52 - 00:33:22]
No, not so much. I mean, so for us, we've been together since high school, so we've known each other since we were 13, and we lived in, like, a 300 square foot apartment together, then an 800 square foot apartment together, then a house. And so, like, I would say, like, it's the difference between, like, where we eat and what trips we go on and what we're able to do, but not so much on our relationship, just because we've seen each other through so many different stages in life.
Anastasia Koroleva: [00:33:22 - 00:33:32]
Oh, that's great. Yeah, because obviously, you know, the rate of divorces is quite high after people, when people sell businesses, so I'm happy to hear you avoid it.
Connor Tomkies: [00:33:32 - 00:33:39]
Oh, yeah. That's not a, that's not a happy thought. So far, so good.
Anastasia Koroleva: [00:33:39 - 00:33:50]
Great. Let's keep it that way. So would you say your definition of success has changed since you sold your business to today?
Connor Tomkies: [00:33:51 - 00:35:31]
Yeah, a little bit. I mean, so whenever you're talking to other people that have sold their business and, like, throughout our, throughout becoming an entrepreneur, it's interesting because if you're working inside a bigger corporation, you understand where you are in the hierarchy and how you're progressing in your career. And as an entrepreneur, the only thing that you can do is kind of, like, sideways and be like, where are these other entrepreneurs? And, like, how am I progressing? How am I learning about where I'm at and what is successful?
And there's always going to be people that are bigger than that run bigger companies than your company. And there's also, like, some founders that are very public about what they're doing, you know? And, like, there's some that are not. And I was in a camp where I had my head down and I never really looked up and saw what other people were doing until after I sold the business. And then I'm looking up and looking around and learning about other people and their stories.
And so I think my definition of success has changed because now I'm talking to entrepreneurs, like, five or ten times a week, and I'm having these relationships with them, and you come across people, and you really, I think, in my head, I'm definitely learning that we're all just people of us, figured out some things and some of us didn't. And my definition of success and where I kind of fit into it is a little bit different now. So, yes, my definition has changed. If you were to ask me to define it right now, I probably couldn't.
Anastasia Koroleva: [00:35:33 - 00:35:52]
Which is very understandable because you must be going through a big transition right now. You know, statistically, it takes ten years to get to clarity and to get over post exit crisis. Obviously, you know, some people have it harder than others, but it's ten years.
Connor Tomkies: [00:35:52 - 00:35:55]
Ten years? I have to wait that long? That's rough.
Anastasia Koroleva: [00:35:55 - 00:36:04]
You don't have to wait. You better get to work before people are fine.
Connor Tomkies: [00:36:04 - 00:36:05]
And that's the average.
Anastasia Koroleva: [00:36:06 - 00:36:08]
Average, yeah.
Connor Tomkies: [00:36:08 - 00:36:14]
Yeah. So I could either be one year and I could be on one side of the average, or I could be, like, 80 years old, figuring it out.
Anastasia Koroleva: [00:36:15 - 00:37:03]
But, you know, I've been. I've been obsessing about this whole post exit thing for 13 years now. And I have to agree that after about ten years, you look back and you clearly see patterns. And when you talk to other people who exited more than ten years ago, they agree on those patterns with you. But of course, when I was just, you know, two or three years after the exit, it's not possible to see these patterns. You always think, oh, now, I already figured things out. And I was writing a blog at the time, and I remember that, you know, two or three years after my exit, I was really thinking that I was sharing my amazing wisdom with the world. And now looking back at that wisdom, it's quite embarrassing because obviously, you know, I've moved on quite a bit. So, yeah, ten years.
Connor Tomkies: [00:37:03 - 00:37:11]
Isn't that true for any healthy person, though, that you're embarrassed by the person that you were? Right. If you're not embarrassed by who you were in the past, you're not growing.
Anastasia Koroleva: [00:37:12 - 00:37:15]
Yeah, it's a good sign that, you know, you've moved on.
Connor Tomkies: [00:37:15 - 00:37:28]
Have you ever looked at your early Facebook posts, like, your very first ones, and you're like, oh, what was I thinking? Like, why did I post that? It's a little embarrassing now.
Anastasia Koroleva: [00:37:28 - 00:37:30]
You gave me the idea, I'm gonna do it later today.
Connor Tomkies: [00:37:30 - 00:37:44]
It's a little cringy, but yeah, to your point, I hope that I'm embarrassed by who I am now, a year or two from now. As cringy as it is, it just means that progress is happening somewhere.
Anastasia Koroleva: [00:37:44 - 00:37:55]
Exactly, exactly. So let's talk about how your thinking about purpose evolved over time. Why did you start your first business?
Connor Tomkies: [00:37:55 - 00:39:32]
I had wanted to do prosthetics and work in the healthcare space for as long as I can remember when I was little. And oddly, my wife wanted to do business stuff, so she was doing Deca and wanted to be an entrepreneur. Deca is a business contest in high school, and I was doing health science, technology, and interning at hospitals in university. We swapped right? And she's now a doctor, and I'm now an entrepreneur.
So we swapped years, our wires got crossed, and so I didn't know what I wanted to do. I wanted to get into architecture briefly and then realized that it's kind of hard to make a living and you're doing a lot permitting. And I had this idea of around, like, setting up campsites before people got there. So I would be renting out, like, equipment to them and setting up the campsite for them. And that would be like a way to make money in college and you're making money off the rental plus the setup and whatnot.
And I made a website, and I thought it was kind of cool that the website gave this idea credibility because there was this digital storefront at the time, which is easy to do now, but harder to do then it was like, you created something. And so I thought that process was really fun. And then from there, I made a company called delegate it, which was like an omnichannel, kind of like backend service. And then from there, embark and support Ninja.
So it's just more of, like, each thing led to another thing, and it happened pretty organically.
Anastasia Koroleva: [00:39:32 - 00:39:35]
Okay, so do you have a sense of purpose now?
Connor Tomkies: [00:39:35 - 00:39:48]
A sense of purpose now? I think I really enjoy the idea of community, and I really enjoy the idea of bringing people together. So I think that brings me the most joy. So if I'm focusing on one thing, I'm probably focusing on that.
Anastasia Koroleva: [00:39:48 - 00:39:52]
Have you ever felt guilty about your financial success?
Connor Tomkies: [00:39:52 - 00:40:52]
No, not so much. I think it's important, at least for me to understand what role I play and the different stakeholders I work with. And I think that whenever we were looking at wage rates for all the employees, we pay above market rate, invest back into the schools and the orphanages and the areas that we work in and we, as far as, like, the stakeholders and the different companies that I ran, they all did really well. And so, and for all the employees, we did a lot of, like, option grants, and people were able to start businesses from when the company sold.
And so it's really cool to see, see that happen. And so, not a lot of guilt. No. But you have me thinking, and so if I think about it long enough, maybe I might find something to feel guilty about.
Anastasia Koroleva: [00:40:52 - 00:41:07]
Okay. If you felt guilty, you would know it. But it's great. It's a perfect answer. You avoided feeling guilty because you did all these amazing things.
Giving back and taking care of other people makes a lot of sense.
Connor Tomkies: [00:41:08 - 00:41:23]
Some of the ways that we structured the exit is that a portion of the money that we would have made goes to the employees. And so that really helps with making sure that all the stakeholders are benefiting from that exit and that experience. But you were asking about imposter syndrome.
Anastasia Koroleva: [00:41:23 - 00:41:30]
Another popular term that flies around in the post exit founder community.
Connor Tomkies: [00:41:30 - 00:41:59]
Yeah, especially when you talk to other post exit founders. You're like, well, what am I doing in this group? Because some people have done some amazing, amazing things. So, yeah, I feel imposter syndrome all the time. That's probably another thing that's healthy, though, like feeling embarrassed about your past self, but also feeling like you're an imposter.
Like all these things are probably signs of growth. If you don't feel that way, you probably aren't. Aren't moving forward. You're probably in the wrong room.
Anastasia Koroleva: [00:41:59 - 00:42:14]
Feeling those unpleasant feelings motivate us to move forward, to grow into that person we want to be, but feel we are not yet. There's definitely a positive way to look at it. I agree.
Connor Tomkies: [00:42:15 - 00:42:40]
Isn't that a hard balance, though? Because you're looking at other people and you're evaluating yourself in relation to them, and that's how you create the imposter syndrome. And that's also the motivation and the driving force moving you forward and driving you. But on the other hand, that's also causing you to have a lack of happiness and a lack of fulfillment. So it's like, have fun walking that tightrope.
Anastasia Koroleva: [00:42:40 - 00:43:11]
Yeah, but imposter syndrome can also come to you from your comparing yourself to whomever you want to be yourself. Right. It doesn't have to come from you comparing yourself to other people. Yeah, but whatever it comes from, it's definitely a source of suffering. And suffering does push us forward, but temporarily reduces the level of happiness, that's for sure.
But that's how we're designed to be, right? We move forward because we have a kind of desire and we suffer until that desire is satisfied.
Connor Tomkies: [00:43:11 - 00:43:21]
Yeah. And at some point we will find our Zen and or take an SSRI and find our happy place. So we'll figure it out.
Anastasia Koroleva: [00:43:22 - 00:43:29]
I'm curious about how your parents defined your success, whom they wanted you to be.
Connor Tomkies: [00:43:29 - 00:44:23]
I don't think my parents and my in-laws understood my companies or what they did too much in the beginning. I think that they're happy now, but I think they're probably still scratching their head and still being like, what is Connor doing? And how do these pieces, uh, kind of fit together? I was having coffee with my mom, uh, I was saying, like six or seven months ago, um, after stepping down, and I was outlining, here's operator equity, here's the companies that we're buying, and I was outlining on the table, like, with salt shakers and sugar packets, like, how these companies are going to support each other. Um, and so I think that they're, they're happy for me.
Um, but I think they are still figuring out what that, how I fit into this world and what I'm doing.
Anastasia Koroleva: [00:44:23 - 00:44:35]
So you don't have kids yet, but I know you have been thinking about how to raise them. Would you like your kids, hypothetical kids, that you don't have yet to become entrepreneurs?
Connor Tomkies: [00:44:35 - 00:45:35]
Oh, geez, that's an interesting question. Hypothetical kids. I don't know. I have a hypothetical son, and he's great. Um, the hypothetical daughter, not so great.
I think she's going to be an artist or maybe go into trade school. Um, but, uh, it's hard to say, right, because it depends on what their, their interests are and how they align. And, and there's so many people that are entrepreneurs that don't fit into the standard, like, tech entrepreneur, uh, kind of space that we, we normally think about. Like, um, they could be an entrepreneur and like, own a trade school or art shop or, or like, own a small business that's a little bit more traditionally defined. If they are an entrepreneur, I would be super excited, and I would be, like, helping them build a landing page and a logo, and I'm all for it.
But if they don't want to be an entrepreneur, that's fine, too. Yeah, I'm open to wherever their journey takes them. It's a fun thought, though.
Anastasia Koroleva: [00:45:35 - 00:45:41]
So if we talk about operator equity again, are you investing your own money in it?
Connor Tomkies: [00:45:41 - 00:46:19]
Oh, yeah, for sure. So the first deals were definitely my own money. And it's like that for a few reasons. One is I'm figuring out how this venture, studio, family office is working, and the way to have the most independence is to be investing your own cash and figuring out how to leverage your own finances. But then after that, it depends on the deal.
And so if the deal aligns with other people or other entrepreneurs and it opens it up to have an investment group come together on a deal by deal basis. But to answer your question, yeah, in the beginning it's definitely my own money.
Anastasia Koroleva: [00:46:19 - 00:46:21]
But you already bring in other people's money in or not yet.
Connor Tomkies: [00:46:22 - 00:46:38]
Yeah. So for example, the deal that we're looking at now is probably going to be a joint investment and it's going to be other people that sold their company to operator equity that are going to be involved in that next deal. So it's, it's happening.
Anastasia Koroleva: [00:46:38 - 00:46:40]
They're recycling money.
Connor Tomkies: [00:46:40 - 00:47:24]
In a way and then also I think it might be great to like, once we have a pattern in the system and understand exactly what value we're providing to the companies, then it's opening up the door for us to bring on other LP's and other entrepreneurs that have also sold their companies to help out and in which case operator equity can expand. But what operator equity doesn't have at the moment is a certain mandate for growth. The mandate is we're taking some of the pressure off and we're making sure that we're providing value to the logos that we already have and the brands that we already have. And so once we have that figured out, then naturally it's going to set up a position for us to raise a fund around some of the stuff that we're doing.
Anastasia Koroleva: [00:47:24 - 00:47:27]
How hard are you working? What's your typical day?
Connor Tomkies: [00:47:28 - 00:47:48]
There's some days where it's like 12-14 meetings and then there's some days that are more quiet and I'm able to get some work done. I would say I am working probably 70 or 80% the hours I was working as the CEO of support Ninja. So I'm working a little bit less, but there's high tide and low tide.
Anastasia Koroleva: [00:47:49 - 00:47:54]
So on a scale from zero to ten, how would you rate your fulfillment?
Connor Tomkies: [00:47:54 - 00:48:04]
I would say right now I am a seven on a way to an eight. And I will have to check in after ten years and understand if I actually am or not.
Anastasia Koroleva: [00:48:05 - 00:48:09]
Fantastic. So what makes it so high?
Connor Tomkies: [00:48:09 - 00:48:23]
I think that I really enjoy the people that I'm working with and so that ties into the community aspect and creative expression. I'm able to have more creativity now, which is pretty enjoyable.
Anastasia Koroleva: [00:48:23 - 00:48:24]
So it's creativity in people?
Connor Tomkies: [00:48:25 - 00:48:42]
Yeah, I mean, those are covering some basic human needs, I think, for me. And that's making me feel pretty happy. It's that ability to, I guess, understand what gives you energy and what takes energy. And I'm spending a lot of time on doing things that give me energy, which is fun.
Anastasia Koroleva: [00:48:42 - 00:48:46]
Connor, my last question, how do you want to be remembered?
Connor Tomkies: [00:48:46 - 00:49:30]
That's a hard question because on the other hand, it's amazing how quickly people are forgotten. And so it's a really hard, hard question to answer. I think I want to be remembered by what I provide to my family and my community, my friends. I think that's pretty important to me. I think I want to be remembered as a person that gave more than they took.
So, and facilitated a lot of good times and happiness. So hopefully, hopefully, that's why I think.
Anastasia Koroleva: [00:49:30 - 00:49:34]
That'S beautiful and you're on the way to achieve that it sounds like.
Connor Tomkies: [00:49:34 - 00:49:47]
Hopefully we will see good times to be had. But I think that if I was to die tomorrow, I think I have lived a good life and I don't have many regrets at the moment. So I'm pretty happy with how things are.
Anastasia Koroleva: [00:49:47 - 00:49:50]
Thank you so much. I really enjoy the conversation.
Connor Tomkies: [00:49:50 - 00:49:51]
I enjoyed it, too.
Anastasia Koroleva: [00:49:51 - 00:49:55]
And best of luck with all your many new projects.
Connor Tomkies: [00:49:55 - 00:50:02]
I appreciate it. And we'll check in at some point and I'll be like, everything is great, or I'll be like, everything is terrible. I appreciate it. Have a good one.
Anastasia Koroleva: [00:50:03 - 00:50:06]
Thank you so much, Connor. Have a wonderful day.
Connor Tomkies: [00:50:06 - 00:50:06]
100%.
