Made It with Connor Tomkies

[00:00:00] Benji Markoff: I don't think there's a single entrepreneur I knew who's =had success, who didn't have years and years of like painstaking 20 hour days, crying in the bathroom,

In those early stages, you think you're in this fishbowl, right? every mistake is going to be just the biggest mistake. It's going to just be such a big blunder and derail your every dream you had. you realize once you get through those things that like, no one's even paying attention to you. it's a flash in the pan mistake and you just move on and you're just wiser for it.

Hey, co founders, welcome to Made It with Conor Tompkins, a podcast where we meet with badass entrepreneurs who've successfully exited their companies, discussing everything from the wins and losses of entrepreneurship to the next steps after the exit. To not miss out on these exciting stories, be sure to subscribe wherever you get podcasts.

Let's dive in.

[00:00:56] Connor Tomkies: Hey everyone. I'm here with Benji. He was a sales manager at cohort, and then he started a New York venture community, that led into founder shield, a insurance company for startups. and then he's also a part of his own family office interplay, and he's launching some new things that are coming around the bend. So I just want to say welcome Benji. good to have you.

[00:01:18] Benji Markoff: Thank you so much. It's a pleasure to be here.

[00:01:19] Connor Tomkies: you have your own podcast that's about to come out. It's called the shit. help me.

The

[00:01:23] Benji Markoff: The schvitz sessions. Yeah. not the shits. That's a different podcast. That's season two.

[00:01:29] Connor Tomkies: That's like whenever you're in there for too long.

[00:01:31] Benji Markoff: yeah, that's where things go. That's where things go real already. Honestly, it's just, it falls in line with a lot of the other stuff I'm doing, but, I enjoy the podcast format.

I enjoy talking to people. I'm, a extreme extrovert by nature. I love saunas. I love like new age, wellness strategies and techniques. And then it was incredibly impactful, especially post exit for me. Cause I went through like a very classic 1 percent problem of, sold your company for a bunch of money and feeling lost and useless and imposter syndrome.

And, I was a therapist. wet dream? I think,

[00:02:08] Connor Tomkies: As soon as you exit, the therapists are like down the block just waiting for you.

[00:02:12] Benji Markoff: exactly. I was noticing that. I would always have really interesting conversations. in a sauna you're definitely completely exposed in there. and number two, I think, your heart's racing, you're sweating bullets, your mind's kind of starts to get a little loopy.

And you completely let loose, or at least, I've experienced that other people have like really let loose in those types of conversations and the types of conversations that I've had with like super interesting, successful, people have been very different from if I was just like, Add a meal with them, or having a coffee with them.

I thought to myself, it'd be really interesting to post a podcast or like a video, audio visual, YouTube channel podcast in which I'm talking to people that I find interesting and seeing where it goes and put the format inside of a sauna, which, you know, 190 degrees or higher.

the goal is for, the guests to last at least a certain amount of time

shamed if

[00:03:09] Connor Tomkies: ones, but it's your entire body.

[00:03:11] Benji Markoff: exactly. fully physical hot ones. the concept is that, they're challenged or they're shamed if they can't beat the previous guest's time.

it's like a personal, fantasy factory that I'm like creating over here with that or with other businesses I'm doing and just enjoying it. I think that the conversations that might come out of that are going to be really atypical, at least in compared to a lot of other podcasts that are popular, that are out there, present company excluded.

it's a social thought experiment for me to see what happens. the only goal I have around it is consistently put out, content. I'm not marketing it. I don't care if anyone listens to it. the benefit is more so for myself and, to,be able to express like my artistic side, I think, and, in a handful of different ways and through a handful of different platforms.

[00:03:59] Connor Tomkies: I think that's a helpful way to look at it. And also, the whole Sana idea. are you just inviting people to be like, Hey, you want to, Sana with me?

[00:04:06] Benji Markoff: Basically, I, yeah, basically, I have a solid list of a couple hundred potential guests, that, I'm close with, or some dream guests, And the idea is just to have them over. I built this sauna in my backyard, it was actually a much more complicated, project than I initially anticipated because I had to rig the sauna so that it could basically double as a recording studio.

[00:04:29] Connor Tomkies: that's interesting. I have a hard time making this work, just in an office, let alone, a sauna. You know what I mean?

[00:04:34] Benji Markoff: and by the way, I have no idea if it's going to work. I have no idea if it's going to work. It's just going to be an iterative process and we're going to have to figure it out. we rigged the inside with these heat resistant, high end GoPro cameras and we installed like these mics from the ceiling, with these heat resistant covers, on them.

We'll see what the outcome of that is. I don't think audiophiles are going to be tuning in and enjoying it, it's something that I personally am excited about just sitting down in there with someone and there's this also, there's this

mental hurdle and challenge, that when you are in a sauna with someone else that create this bond around this communal experience is when it's the same thing with, starting a company, going through those challenges, the bond and the relationship and the level of, depth, in that relationship when you experience something challenging together, I think is.

Yeah. It's really unique and special, and so trying to flash in the pan, create that over and over again and see what happens.

[00:05:38] Connor Tomkies: Yeah, you're in the schvitz together, right? you're in the thick of it.

[00:05:41] Benji Markoff: exactly. we're going to have a cold plunge outside as well, so we'll probably

[00:05:45] Connor Tomkies: say, I was like, as long as you can jump into something cool after that, that would feel

[00:05:48] Benji Markoff: yeah, so I might have a second segment that's three minute, quick questions in the cold plunge, right?

[00:05:54] Connor Tomkies: have to ask you really quick, because I know that you're jumping into podcast life now. for those that don't know you, how did you go from being a sales manager to starting a company and founder shield?

[00:06:04] Benji Markoff: Yeah. the high level story of that goes, I was the junior, business development salesperson on this, early stage venture backed company called Cohort. This was in, I'll call it end of 2010, early 2011.

We raised 3 million and, founder, co founder I, Benji, you deal with insurance because we're busy.

yeah, sure. I can handle it. I was, go getter. I figured, low man on the totem pole, say yes and figure out how to accomplish the goal afterwards. And I just remember that the experience of finding a broker, going through the process of buying commercial insurance, the, how debilitating it felt and how antiquated and archaic that entire process was.

And I was. So inundated in the technology world or in the startup world, I was just blown away by how little tech was being used or no tech was being used as related to commercial insurance. we had such a hard time getting insurance because in the insurance industry as a whole had very little faith.

In venture backed businesses and early stage startups at that time. And the way they thought about those companies, did not fit into what their traditional underwriting guidelines looked like. And so companies like ours just had a difficult time. We're overpaying for insurance. that was just on top of how time consuming and how archaic the whole process was.

Logged that, painful experience in the back of my head and as, the next kind of year went on, pushed it aside, forgot about it, but probably towards the beginning or middle of 2012, the writing was on the wall that the company I was working at was not going to raise any more money.

They were going to go under, they hadn't achieved product market fit yet. and. I was thinking about what I wanted to do next, and I was talking to a mentor of mine, and we got to the point where I realized all I really wanted to do was anything around sales, right? I absolutely am obsessed and addicted to the science of sales, the strategies behind sales,

I would have always loved to be a professional athlete, but unfortunately didn't have the height or athletic ability to be able to ever get there. and so sales is, in my mind is the kind of perfect, antidote for that, right? there's so many parallels between sales and sports and athleticism.

I was just drawn to it. And so as I was going through that process, I thought back to that experience about buying insurance and I guess I was, either, overly confident or, I guess properly confident. I'm not sure, jury's still out, but that, if any, if people, businesses buy insurance, I can convince them to buy it from me.

[00:08:50] Connor Tomkies: Benji, that's a really hard industry to get into. I feel like it has a built in moat because even whenever I think about insurance, my mind goes blank.

[00:08:57] Benji Markoff: I was attempted to talk out of it many times from a handful of different people. A lot of people told me that you can't just start an insurance brokerage or an insurance company. You need X number of years of experience. You need all of this knowledge.

[00:09:10] Connor Tomkies: I guess they weren't right or they

[00:09:12] Benji Markoff: No, they were definitely wrong. I think that there's a lot of, there are significant benefits to, not, having any sort of experience in an industry before you try and disrupt that industry. you don't have the perspective of. Your prior experience in that industry and using that as a way to try and achieve success in the industry.

For me, I looked at Foundershield, not as, Oh, here's how we are going to disrupt insurance. cause I didn't even know what it meant to disrupt insurance outside of digitizing the process. I really thought of it and I was inspired by, the Tony, Shea book,

[00:09:47] Connor Tomkies: Oh, the one on customer experience

[00:09:49] Benji Markoff: I think it's called delivering happiness, something along those lines. one really stuck out, to me in that book, which is, Tony Hsieh is talking about the fact that he doesn't even like shoes. He owns two or three pairs of shoes and he gets into this whole conversation about Zappos is not about, it's not a shoe company, right?

Shoes are just a means to what they're really delivering, which is extreme levels of happiness and extreme levels of pleasure and excitement. And the vehicle in which they do that through happens to be through shoes. And so I thought of that. I said, you know what, the challenge I put to myself was, shoes are great.

It's like a gift to yourself. They're nice. Imagine if you could deliver, some sort of positive vibes, some sort of happiness around something that people push off, dread doing, which is buying insurance. It's like a necessary evil that people just have to deal with. and imagine if you can achieve like some level of excitement or happiness or, in, my dreams, I was thinking that.

what if people were excited to, get on the phone with us?

[00:10:51] Connor Tomkies: I'm trying to imagine a happy experience and I'm, struggling here.

[00:10:54] Benji Markoff: how did we pull it off? I think it was, extreme levels of attentiveness towards like customer service and customer support and really getting into the mind of our customers and understanding what their pain points are and understanding, what their stress levels were at any given point in time.

And how we could be a value add, to their ultimate goal, which is to achieve whatever dream or level of success they had built up for their company. And so if we can be a vehicle that, allows them to even increase the odds of achieving their dream by 0. 01%. We'd be accomplishing our goal.

[00:11:34] Connor Tomkies: So Benji, what were some, you ended up selling this for nine figures. How did you, what were the inputs? Did you have co founders? Did you raise rounds of investment?

[00:11:42] Benji Markoff: Yeah, I had a co founder, We bootstrapped the whole time. never raise a penny. And it was Very difficult, but, very thankful and very strategic decision not to raise capital and, a old mentor of mine was definitely give credit to him for, pushing that thought in our head and even as we were getting interest from a lot of, funds, he kept on telling us just grow at your own pace.

it's a lesson that I've taken on, as I'm advising other startups, as I'm onto like my next things, it was the most important decision, and it definitely, was a key reason, that led to the success we had in the ultimate exit that we had.

We had to really be confident in our internal investments where we were going to, put our money to work. it ended up making us. Much better, smarter decision makers and making the right decision more often than not. then I think if we were in a position where we had a ton of cash and a ton of runway to make mistakes, we didn't really have that, flexibility.

it allowed us to achieve an exit that, was really unique in our industry because we were both a profitable company and a high growth, a hundred percent year over year company, over almost a decade and a, company that. Over that decade of time had developed and built a lot of proprietary technology.

And the combination of all of those things allowed us to have like access to a really large pool of interested, acquirers.Which I think ultimately led to the, exit multiple that we ended up achieving.

[00:13:25] Connor Tomkies: There's not so many people in the space. So if I was an insurance company and I was looking at potential acquisitions, it's not e commerce, right? You have a very slim set of options.

typically for most, strategic acquirers, so most insurance companies, larger insurance companies, there's minimal organic growth year over year, especially once they hit a certain size. and most of their growth is attributed to, to strategic acquisitions. and there's a pretty, active M& A market, but it's mostly, traditional insurance brokerages buying smaller, traditional insurance brokerages and basically, utilizing their book of business, book of revenue to determine the, The acquisition value you're definitely solving a pain point. we're both part of this group where a bunch of other founders talk about issues that they're facing. And did you see that thread on insurance?

[00:14:10] Benji Markoff: it's on the personal side. So even though it's not like on the company side, even though it did touch on that, it's all these people that have had massive insurance plans before and yet they're still scratching their head about Oh, how do I go to the doctor's office?

[00:14:21] Connor Tomkies: Which is funny to think about.

[00:14:24] Benji Markoff: it's wild. It's the truth is we actually, we had many opportunities to. dip our toes and dive into the personal line side and the health insurance side as well. And we,were very strategic and not, allowing ourselves to go in that direction and trying to expand our TAM that way.

but that was mostly because the sales organization we had built up internally, the skills they had in the way we had trained them. Was really focused on their ability to sell into companies, which is a very different kind of path and strategy that needs to get utilized versus selling, to individuals, you're dealing with a much more emotional buyer when you're dealing with personal insurance.

[00:15:04] Connor Tomkies: Yeah.

[00:15:05] Benji Markoff: Commercial insurance it's just a different set of tools that are required in order to, I think achieve the level of success I would have wanted to achieve in that area.

[00:15:15] Connor Tomkies: on your website somewhere, I saw that you were talking about like your proliferation into the VC marketplace. Is that part of your Go to market is you would go to VC companies and just be like, Hey, we can cover your entire portfolio essentially.

[00:15:27] Benji Markoff: when we first started the company, September, October, 2012, I made sure to brand our business as insurance for startups. That was like the initial tagline. and the reason why we did that was because there was there was no, we knew that at that point there were no other insurance brokerages.

That focused on startups. And on top of that, we were confident that even if there was a, competing larger insurance brokerage, one with more experience who could say, Oh yeah, we've, we work with high growth companies or startups, they wouldn't be able to say they exclusively work with startups. And be able to market that Hey, this is all we do.

[00:16:03] Connor Tomkies: All we know we're super like narrow, deep, and not wide area of expertise. And I think that allowed us to, develop a level of comfort between us and, our prospective buyers. We did something similar. Like we were outsourcing for startups. And then as they grew, we grew, it was like, yeah, they might be like a Y combinator company and they just got funding. And then eventually they ramp up to hundreds of people and you're just along for the ride

[00:16:28] Benji Markoff: Yeah, that's exactly it. some of our early clients, and then we rode the wave with them. We're like Coinbase, Robinhood, we've seen pretty monumental clients that, we've worked with,

[00:16:37] Connor Tomkies: We were working with Coinbase too, in the early days. yeah.

people were getting paid in like cryptocurrency and we're like, Oh, okay. That's cool.

[00:16:44] Benji Markoff: So I had met with Fred and Brian and we were just shooting the shit talking about, the standard types of insurance that they needed. Do you know insurance, GL for their office, property, all of those kinds of basic insurance needs. And I remember I'd asked him, I said, I'm not a crypto expert. I can't even buy crypto yet. Cause this is like early 2013 in New York. You couldn't really buy it.

I said, I'm like, but I can imagine a scenario where people have a significant percentage of their net worth or a meaningful amount of, of their capital, sitting in, on your servers and your, on your platform and. I told him, I was like, I think we could potentially do what a company like a PayPal does, or even like an FDIC for banks, we could probably promote and market, the fact that Coinbase, that any deposits in Coinbase are fully insured and backed by an FDIC.

Lloyd's of London or a legitimate, insurance provider. And especially at that time where like crypto was at its infancy. and there was so much fear around the unknown and,

[00:17:47] Connor Tomkies: at FTX and this stuff.

[00:17:49] Benji Markoff: yeah, I remember when Mount, I remember when Mount Gox, happened, which was, I think, 2014, maybe, that almost derailed this, this entire concept.

we basically. He worked really closely with Fred and Brian and, ended up developing the first ever insurance product for cryptocurrency,

[00:18:04] Connor Tomkies: Oh, that's awesome.

[00:18:06] Benji Markoff: ended up getting up to, I think it was like a billion dollars in capacity in that like initial structure. and Fred and I, we must've flown to London a dozen times to meet with Fred had to literally teach blockchain technology and crypto to 50 different heads of, different Lloyd's syndicates.

All, white haired, middle aged men,

[00:18:27] Connor Tomkies: You're like, you send the money where? Like, where does it go?

[00:18:31] Benji Markoff: exactly. And they're, like, middle aged, proper, British men, who at first were like, I'm like, This is never, they're never gonna understand this.

[00:18:41] Connor Tomkies: How did you get them to sign off on that? That seems a little bit of a stretch.

[00:18:46] Benji Markoff: I don't think I was overly strategic. I think I was just absolutely relentless.

[00:18:52] Connor Tomkies: Yeah,

[00:18:53] Benji Markoff: I'm going to make it happen. I have this tendency to, over promise and then do everything possible to deliver on that promise. Sometimes it's bitten me in the ass.

but in this situation, It worked out well.

[00:19:06] Connor Tomkies: you're working backwards. You're like, this is going to happen, and you're like, how are we going to do this?

[00:19:11] Benji Markoff: I can't get away from that even to this day. I still do that. And it's just, I think it might be just the way I motivate myself and the way I guess I, I work best. I like to, be thrown into the fire and, sink or swim Experience and mentality is, uh, beneficial to me.

I think,maybe I'm just a masochist, But anyways, that, that experience, with Coinbase led us down this path where we realized that there was this whole nother. opportunity to not just be a tech enabled, tech automated commercial insurance brokerage, but to be a truly,tech enabled, vertically integrated insurance experience.

We realized that we could go down this path where we can not only, create a really optimal customer experience, from the broker's side of things, but we felt that we could get to a point, to achieve what we believed was like the, The ultimate goal, which is fully own the entire process A to Z, because that's the only way you can truly, create, a custom specialized experience for your clients.

And so that was the path that we went down and that really unlocked A lot of growth for us and, a lot of innovation that ultimately led to our exit.

[00:20:24] Connor Tomkies: you were there for 11 years. So it was like a, an overnight success that took 11 years to build

[00:20:29] Benji Markoff: Yeah, exactly.every founder I know has,from, the external point of view,overnight made it big and I don't think there's a single entrepreneur I knew who's had success. who didn't have years and years of like painstaking 20 hour days, crying in the bathroom,

I've lost count of the number of times this happened to me, but,most people don't see that side of it it because you're, honestly, the truth is it's the beauty of being an entrepreneur. And I think once you get through the other side, you realize it is that In those early stages, you think you're in this fishbowl, right? You think that every mistake is going to be just the biggest mistake. It's going to just be such a big blunder and derail your every dream you had. And it's, life or death. And then you realize You know, once you get through those things that like, no one's even paying attention to you.

and people, it's a flash in the pan of a mistake and you just move on and you're just wiser for it.

[00:21:29] Connor Tomkies: I think I realized I could take a lot more punches than I thought I could. And the company could take a lot more punches than, like it feels like the end of days, but it's not quite. We had

like, um, an earthquake, take out our office and we're like, Oh, what are we going to do now? And then we had, like we had offices in the Philippines and there was like a typhoon, like every season and the pandemic was like a military style quarantine.

And we're like, we have people on site. what do we do with all these like computers? some people can't get home because they like literally blocked off the highways and you're like,we'll figure it out. And you do,

[00:21:59] Benji Markoff: it's your only choice. You're in. I think it's for anyone who thinks this is,the road towards, an exit or whatever your ultimate goal is as an entrepreneur is just, paved with, butterflies and rainbows. it is not the case.

There are just as many, if I think, if not more, down days than there are like super positive up days. And I think the best entrepreneurs just have that like superpower to be so resilient in the face of that and be able to like, forget it. It reminds me of, I can't remember who it is. I know it definitely applies to like, Steph Curry, which is, any good shooter in the NBA, basically.

If they miss 10 shots, they think the 11th shot is going in, right? And they like, they constantly are forgetting about their last miss. It's, it's over. It's done. Onto the next.

[00:22:49] Connor Tomkies: That's our superpower is we can't remember.

[00:22:52] Benji Markoff: Exactly. We're like, I don't know, that. Dory. Dory and Finding Nemo. I got three little kids, so my Disney references are very on point right now.

[00:23:01] Connor Tomkies: I do think that there's probably easier paths to entrepreneurship and like what you, we went through probably, buying a business is probably an easier way to get into it. And there's pre established processes. I feel like there's an easier way.

There has to be an easier way.

[00:23:16] Benji Markoff: bought a business now. I've went through, another M& A deal that ended up just, burning up and into flames in the 11th hour. we're in LOI on another one right now. And so I don't think it's easier.

I think it's just a different set of challenges. I also think it's different depending on what your mindset is and your objectives are going in. I like personally can't like, I'm so bad at looking at a target acquisition or business and saying okay, this is a really good investment.

Just keep, keep the ship steady. Like incremental, changes, over time. I'm like, no,

let's blow this up and turn this into, the biggest thing in whatever, it doesn't even matter what industry. it could be in like, adult diapers.

It'd be like we're revolutionizing adult diapers.

for me at least, that mindset has been helpful because. having like insane, absurd, dreams and ones that are, I think, from an external perspective, like shocking or laughable, create like a certain amount of motivation, And, eagerness to prove people wrong, that I personally find exhilarating.

And I also think that if you shoot for the, for the moon, right? You just. You fall in the stars, right? You'rewhatever you end up, end up doing and succeeding with, even if it's not that like outlandish dream, it's way further,along that path than if you just had a very reasonable,Strategic, do like an achievable dream on an annual basis.

[00:24:53] Connor Tomkies: I came on bouncing back and forth between like reasonable and not reasonable. So yeah, we're going to revamp this entire industry. And then I'm like, disappointed. I'm like, why isn't it revamped yet?

But on the other hand, you're moving forward and you're getting tens of millions of dollars in revenue.

And that's falling. that's pretty good. like that's a win.

[00:25:09] Benji Markoff: It's great. I think different entrepreneurs, love different, stages of, of the startup life. Like for me, I love like the zero to one or call it maybe zero to one, one to two. where it's an unlimited amount of chaos and you are forced to, to make decisions with one hand tied behind your back.

operating on a lot of intuition and gut, I love, wearing multiple hats and having a small team and creating like a really unique culture and, putting together like a dream that feels, misguided on some level.

I love that side. Once a, business gets to a point whereyou know, it's steady, it's repeatable,nine times out of 10, once a company hits that stage, people like shift their mindset to okay, don't fuck this up now.

[00:26:01] Connor Tomkies: it's more like a save what you have, than expand, right?

[00:26:04] Benji Markoff: yeah, that's, that's what I'm like. That's for me personally. I get a lot less motivated at that stage.

[00:26:10] Connor Tomkies: I think I like the 0 to 1, and then I can skip 1 to 2, and then 2 to 3. I'll be happy. You can start up a landing page. You can build the initial team. You can bring in the first X million and revenue and get it going. And then there's the awkward, like middle stage.

Like I'm going to call it the adolescent teenager where like things are uncomfortable and you don't quite have experts in all the positions. And then I'll come back and I'll be excited whenever I have all my seats filled with Fantastic people that are really know their shit and are kicking ass in each area.

And then I feel like they're like amplifying each of the different segments.

but I think that I don't even know if two to three is part of the saying,

[00:26:47] Benji Markoff: we're entrepreneurs. we're creating our own paths,on a continuous basis.

[00:26:50] Connor Tomkies: We need to tell Peter Thiel about the one zero to one, one to two, two to three. Now there's more to it.

[00:26:57] Benji Markoff: we do that and we get juiced on steroids with him.

I don't know, Peter, if you're watching this, um.You need to get into a sauna and say hi to Benji

will happily take sponsorship dollars from the, roided up, Olympic Games that he's starting.

[00:27:10] Connor Tomkies: it sounds amazing. I want to see athletes just destroy like previous records with a performance enhancing drugs.

[00:27:16] Benji Markoff: that's basically like what American Gladiator was like trying to do in like the early nineties. turning it into a Olympic level competition, it will definitely be interesting.

[00:27:24] Connor Tomkies: Like as long as it's, how do you say safe? Like, how do you put performance enhancing to a point or else, doesn't that get problematic?

[00:27:32] Benji Markoff: they haven't provided enough details there in it. I assume it's like to some certain levels.

[00:27:37] Connor Tomkies: if you go too far you have roided up anger issues happening on the track you know you're like hey focus

[00:27:43] Benji Markoff: maybe that's part of the competition. It's boxing and track and field together.

[00:27:47] Connor Tomkies: We should talk about what, so tell me about the exit. What was that like for you and what are you looking to do next?

[00:27:54] Benji Markoff: Such a unique and grueling and just exhausting and rewarding experience. It was just a common, it was every possible emotion all rolled up together. the way we ended up, selling. Cause we were bootstrapped. we didn't have any pressure to sell or anything like that.

We weren't trying to reach some sort of Valuation and raise another round. We didn't have any sort of time pressure on us. but we had to end up getting two like unsolicited LOIs, in December of 2020, and they were Interesting enough, from a total dollar standpoint, they were like, okay, shit, this is what people are willing to pay for us.

This is crazy.

we ended up interviewing a handful of investment bankers, settled on one and then just did the gauntlet of,six, seven months. We had, I think we had 77, first round meetings. and we had this scenario where we had interest in a lot of different, acquirers investors.

went four paths went down the path of a SPAC, considered it. went down the path of private equity, went down the path of,growth fund,and kind of raising our first round, but like a massive one. and then we went down the strategic path. through that process, I remember, it was COVID time, so it was still like, still in the stages where people, weren't really traveling.

our bankers for the first probably like month.

We did like dry runs and, just like practicing the pitch. there's a different strategy when you're pitching a client versus when you're pitching someone who's looking to buy you, right? you're dealing with, A different set of goals or incentives and, have to be a chameleon in a different way as it relates to those pitches. had key points and we were talking, I think it was like two or three meetings a day, an hour and a half each.

[00:29:42] Connor Tomkies: It sucked. it was just absolutely exhausting. it broke me countless times. I had so much doubt during it. I'm like, this is.

[00:29:51] Benji Markoff: We're not going to sell. and, I'm lying to my employees, it wasn't, lying, but I'm like, I can't communicate with,

[00:29:57] Connor Tomkies: You have to keep it to yourself, right?

[00:29:58] Benji Markoff: yeah, exactly. and I'm like that they know something's up because I'm not as involved or attentive, um, to their needs.

it was just absolutely grueling and wake up in the middle of the night, just like sweating bullets thinking like, Oh my God, I messed up that pitch a week ago. but. I guess there's some type of, level of resilience. We ended up pushing through that, getting to,that next round.

I think we had 10 or 11 LOIs all said and done.

I think part of it was that were a unique company in the sense that like we were a high growth. tech company with a bunch of proprietary technology. and we had really healthy, like kind of venture level organic growth, year over year, and we were profitable every year that we operated.

[00:30:43] Connor Tomkies: like 20 percent growth, 20 percent EBITDA or something like that. Like you, you were blowing out the growth target

[00:30:49] Benji Markoff: we did not plan it this way, but, we went through this, M& A process. I couldn't have picked a more perfect time. We, it was, it basically started right as that, like initial level of fear of COVID, was, dissipating and, confidence in the market started to increase a little bit.

There had been so much like dry capitalready to be deployed because no one did anything for nine months.the market was just like, foaming at the mouth, wait, like needing to make acquisitions. And so we came in just at an absolute perfect time and End up selling to a company called BRP and, the rest is history.

[00:31:32] Connor Tomkies: Congratulations, man. That's awesome. running a process is not fun at all. I think I talked to 22 different bankers and brokers to try to figure out how to take us to market.

[00:31:40] Benji Markoff: It is a lot of people and, it's an interesting process. Your bankers are your best friends until you sign the LOI with, with the company you tend to sell to. And then they basically can't be trusted at that point.

[00:31:52] Connor Tomkies: They're like, just trying to push through the

[00:31:53] Benji Markoff: Yeah, no, ignore that. No, we're not going to push here.

Otherwise, it was like, no, we can't push on these terms. They're going to shut the deal down. I'm telling you. And my, my next exit, if I ever, and. That is going to go down that path again. I, will definitely, not hold any punches, or requests. Cause I think we could have, been able to be even more aggressive than we were.

[00:32:13] Connor Tomkies: I hear a lot from bankers and brokers are like, just think about the overall pie or just think about the big picture. And you're just like, Oh man, I'm just trying to get this through. Potentially, depending on if there's an earn out or not, this might be my life for the next two years.

it's important to get the right terms in the first place.

[00:32:28] Benji Markoff:

[00:32:28] Connor Tomkies: You're starting a family office slash almost like a venture studio. it's like a combination of both, right?

[00:32:34] Benji Markoff: initial idea was just like, set this up, set these vehicles up, like from a. like a tax saving standpoint and just proper,financial structures setting it up and as I,finished up that first layer of like legal work, I was trying to figure out, what the strategy was and what I wanted to do next.

Initially. I considered. Not doing anything, forever,

I think my financial advisor would have preferred that,

[00:33:01] Connor Tomkies: yeah, we would make more money if we did nothing.

[00:33:03] Benji Markoff: yeah, You

know, it's funny, it's, um, I'm not definitely not looking to get political, but I, it doesn't matter, to me.

but there's always these different articles about, Trump and how, if he had never done anything based on his inheritance.

he'd be worth like a significant multiple more than he is now.

[00:33:21] Connor Tomkies: will be missing out on Trump stakes,

and Trump Academy and shoes. Yeah.

Like the world would be missing these things.

[00:33:29] Benji Markoff: honestly, I can't relate to a lot, with him, but I can definitely relate to that asset, which is it's at that point, it's not about the accumulation of wealth.

It's you, like you are, you become, you feel dead inside if you're not. Like pursuing those things that you're passionate about, regardless of whether that exposes you to certain levels of financial risk.

[00:33:52] Connor Tomkies: Did you have a identity crisis a little bit like after that? Yeah.

Okay. Me too.

[00:33:57] Benji Markoff: crisis, depression, riddled

[00:33:59] Connor Tomkies: do I tell people whenever I meet some, meet them at dinner? It's what do you do? I'm like, I'm just living,

I would always mix it up. I'd be like, sometimes I'd say to retire. Sometimes I would say I'm a stay at home dad. Sometimes I'd tell the truth. whatever I said, I was uncomfortable with saying. Yeah. Just different answer each time. What do you do? I've, I watched Finding Nemo, like a

few times a day and I hang out with my kids and

just have a different answer every time they ask.

[00:34:23] Benji Markoff: definitely didn't know how to navigate it. It's like one of those things. I don't even know how, you can't really prepare for it, right?

[00:34:29] Connor Tomkies: I told myself Don't let your identity get wrapped up in this thing, like it's not going to last forever. It's a sandcastle, right? the tide's

going to come in at some point. And, yeah, and my identity totally got wrapped up in it. And, yeah, even though I saw it coming, I couldn't do anything about

[00:34:44] Benji Markoff: for a decade, basically, my brain was in this like very like unique fight or flight mode.

And so I basically was in this survival mode where. Anything that would distract me from achieving my goals from, as it related to foundation on that business, it basically just got pushed off to the side, right? but basically just didn't hit my, I don't know, frontal cortex or whatever part of the brain it was going to hit.

And very soon after we sold, it's almost as if like, everything opened up in my head and like it had room for other thoughts and I started thinking about things that I was like, I haven't thought about this ever, and then I didn't have answers.

And I wasn't prepared to,to deal with those,questions and thoughts and, identity crisis and all of that. and instead of, being prepared for that, it was more so I just had to, pick up the pieces and put them back together afterwards.

[00:35:40] Connor Tomkies: I was Like I need a vehicle for whatever's next. So like I did operator equity, which is like like the operators and entrepreneurs are like the LPs and like the funds and you acquire a company and then you guys can do joint deals together in the future. And so I started buying

companies and then, I started doing passion projects, right?

I'm expanding a lot more instead of just doing one thing. I'm doing a bunch of different things. so tell me a little bit about what you're doing on that side with your family office and what company did you end up buying? Are you planning on buying more?

[00:36:11] Benji Markoff: the path that I ended up choosing, to go down from like a family office strategy, after, trial and error was I got to a point where I realized. I'm an operator, and I'm like a risk taker and disrupted by nature and, putting myself in those positions and in those experiences is what excites me.

And so I really shifted focus, from a family office strategy completely away from any sort of passive investments. I basically told my financial advisor, like they, they're in charge of the past investments. I get no excitement out of it at all whatsoever. I could, I just had a, for an angel investment I made, cause I think the first I'd been making angel investments in definitely the first 18 months post exit, I went like real crazy on angel investments.

but I just had this one, company that I had an angel investment in that. Exited for 750 million

that was a company that I. Invested, I think it was at like a three and a half million dollar valuation.

[00:37:16] Connor Tomkies: Oh, wow.

[00:37:17] Benji Markoff: the only enjoyment I get out of it is that I know the founder, I know how hard he worked. And he's like the. Just the embodiment of like persistence and grit and resilience and I'm excited for him.

there's no, I, there's no joy out of it for me. Cause I had no, I didn't do anything. I finally realized I'm like, okay, I have to do stuff. Otherwise like it's just going to be, an unenjoyable, dragging my feet through the mud process.

And so structured the family office where we only focus on building new companies and, majority stake or 100 percent takeover, acquisitions.the second thing that I wanted to, I'm in this position now where I started founder shield and scale underwriting when I was, 24, I was engaged.

I wasn't married yet, didn't have kids and by the time we sold in 2021, my oldest was.four at the time. And and I have three kids and they never have really seen me, work at the like early beginning stage entrepreneurial level that, consume so much of my life. and then I was, proud of and, yielded the.

results, that we ended up achieving. And I really wanted them to like, see that firsthand.

I felt like it was the best way for me to teach them those lessons and those values. Cause those like soft skills that I think, make the difference between good and great for an entrepreneur.

they're hard to teach. and I thought the best way that I could do it for them was. Just by being the embodiment of that and living that life.

and so really that was really important to me. And then on top of that, I really just wanted to, I wanted to get my feet, went into a bunch of different things that I have no experience in and no business being in, and I wanted to start doing things that were polar opposite of what I had been doing and things that were,more tangible because I felt that on top of the.

trying to be like an example of hard work for my kids. I also thought that it would be so much more exciting for them to witness like, from see from infancy, from a seedling idea through whatever the ultimate goal is of something like truly tangible and something that they can experience firsthand.

[00:39:41] Connor Tomkies: Benji, is this going to be the paddle United sports club that

you're launching?

[00:39:45] Benji Markoff: There are two things. Padela United Sports Club. That was the one we're launching. And then I also bought another, is a, indoor 20, 000 square foot franchisor sort of path of growth, kids facility, sports facility,summer camps, things like that.

makes a ton of money. I honestly didn't know anything about this industry. someone, introduced me to, the, former, owner of it. it was something that I'm like, Oh, this is really interesting from just a, profit center standpoint.

And they're, they don't use any tech. It's like it, they almost are like treating it like a real estate play in the sense of. It exists, they make money, and that's it.

[00:40:27] Connor Tomkies: And you can just hold onto it forever.

[00:40:29] Benji Markoff: which obviously is not what I'm doing, I'm like, okay, how do we revolutionize the, the indoor birthday party industry?

both of those businesses are ones that like, I now bring my kids to I show them Hey, this is the change we're making. Hey. And my oldest son, who's can be eight. Like I asked him for like his input on, On this, superdome business.

I told him, I was like, you're the target demo,what is it that you want here? What would be the perfect birthday party here? what would be like the coolest arcades that we should put in here? and so it's really exciting to,have this.

Different sort of entrepreneurial and startup path and journey, in which I can, share that experience with, with my kids.

[00:41:09] Connor Tomkies: I have a fascination for secret rooms. So if you happen to put any secret rooms in that thing, I will check it out.

[00:41:15] Benji Markoff: I'll figure it out. I don't know. Secret Rooms are not a, Not necessarily the best way to maximize utilization, but maybe I'll put my office behind a secret room

[00:41:24] Connor Tomkies: A bookshelf or something like that.

[00:41:26] Benji Markoff: yeah, in Padel United. yeah. and then the

[00:41:28] Connor Tomkies: like offices. Oh Yeah.

Tell me about Paddle.

[00:41:31] Benji Markoff: I think going through like the, mental low points and struggles post exit, one thing that really got me through it was basically being super aggressive in trying anything and everything from a wellness standpoint. and I got super into cold plunging and cryo and, and saunaing, red light therapy as well, even some sensory deprivation,tank stuff.

And so it really had such a net positive impact on my life. And I was traveling to all these places to try and do these things because, the town that I live in, the area I live in Jersey, they just didn't have any of these, spots, around. And I was like, you know what, I'm just gonna, I was like, I'm just gonna buy all of this stuff and put it in my backyard or my, somewhere in my house and Make my own little,wellness,retreat in my home.

And my financial advisor called me up, he's you have, he's Benji, you're an idiot. Stop doing this. get a retail location and put all that stuff there. and go there for it. Even if it's just for you, go there for it. But don't like, waste money doing this in your own house.

[00:42:35] Connor Tomkies: Yeah. It could be a business or was he seeing it more as like a tax like thing

or, or both?

[00:42:41] Benji Markoff: for both, but mostly it's like you can, even if the business fails, it's still a business expense if you try and attempt to make it into a business. And so I said, I'm like, okay, you know what, I really wanted a kind of like a social wellness club in my town. I thought like this area of Jersey, which is it's affluent, it's beautiful homes, upper middle class or upper class,Suburban, suburban, towns and neighborhoods. I was like, there's nothing here really that,provides that sort of offering. So as I was going through that process, looking for it, I'd also, at the same time I've been introduced to Fidel and I was fascinated less by the sport necessarily, and more so by.

Like the hockey stick, like growth metrics. It was, it w it was, showing and the, like the financial analysis and, unit economics of that business.Because unlike, unlike tennis, Padel, requires significantly less square footage and it's four players instead of two players. So you basically have a two and a half X plus.

Another two X on top of that, potential earnings per,compared to the square footage, between Padel and, tennis. And so I knew that racket sports in general were like super popular, in this area. And I knew that there was like a lack of supply and a massive demand for indoor facilities.

I could combine those two, like those two efforts, those two ideas. The Bedell side, which is social, at its core and like social wellness club. we might be able to create something like really special and really unique.

[00:44:19] Connor Tomkies: This is really cool. I'm looking at a graph, looking at growth of like global sales of padel rackets and like the, these stats are old too, so it's looking at 83,000 in 2002 to 409,000 in 2017. And oddly, Spain and Argentina have the most at this point,

[00:44:39] Benji Markoff: Sweden has a bunch of, Norway,it started in Mexico, Spain is where it really took off now. It's the second most popular, recreational sport behind soccer in Spain. there's around 8 million active weekly player, recreational players in Spain. It's, grown exponentially in, the UAE, Dubai, Qatar,all over the Middle East.

I would say in the past probably 36 months, we've started to see a significant increase in interest and then investment in both the UK and in the U S and there's a lot of, very wealthy individuals and funds, pouring in athletes, celebrities, pouring a ton of capital into, the growth of the sport in the U S and it's.

Yeah. It's really fascinating because right now, as we currently, currently stand, there are less than, I think, 400 public courts, public Fidel courts, available in the US and it's the demand and the chatter around it far outweighs the supply, like there's a massive supply issue here. So there's a massive push, to, Increase that supply, tenfold over the next couple of years to be able to support the demand.

in my opinion, it has all the benefits of a sport like pickleball. Which obviously became like, just grew and became massive in the States, but it isn't played anywhere else, by the way. and so it has all the, growth potential and the benefits of pickleball in the sense that I think the best thing about pickleball is that Anyone can really take it up.

It's very easy to take up. There's not a big learning curve, other than their confusing scoring system. and Padel is very similar from that standpoint. It's really easy to pick up. The difference between the two is that Padel is like chess in that it's It requires like a different level of strategy and a never ending pursuit of of growth in your skills and your strategies and, in, in becoming a better player.

And it also requires a different level of athleticism. So it requires a lot more agility. It's a better workout. You're breaking, a significant sweat and, real athletes, like professional Fidel players are like incredible athletes who are, on the same level to like athletes in a lot of other sports, just from a athletic ability, and it's one of the sports where I, I believe by in 2032, it's going to be.

[00:47:10] Connor Tomkies: introduced into the Olympics,Benji, is this a franchise or is this something that you just came up with and

[00:47:16] Benji Markoff: no, this is, no, I, yeah, no, we just came up with it.

[00:47:19] Connor Tomkies: Okay, cool. if it does turn into a franchise, then let me know.

[00:47:24] Benji Markoff: Yeah. I can't say being a franchise business, especially like our, the strategy there is like very, it's very amenity rich, like luxury for kind of a, country club,vibe.

[00:47:36] Connor Tomkies: Yeah, I'm looking at this. You have, cryotherapy, you have, you're looking at, premium cafes and juice bar, children's play area. Actually, the children's play area is pretty sweet.

[00:47:45] Benji Markoff: that was,an important thing I think for our, because our strategy is very much focused on what I think is it's even less about Padel and wellness. it's really about what I believe is like the core issue that like I'm trying to solve for, which is why, You saw this like during COVID, post COVID, where a tremendous amount of wealth and,Millennials moved outside of like large metropolitan cities, moved into the suburbs, and there's just a lack of like unique, special, transformative retail experiences in the Burbs.

[00:48:20] Connor Tomkies: this idea of, a third place, right? And suburbs are missing that. And the third place, for those that don't know, is it's not your home, it's not your office, it's what used to be the bar, or the club, or the lounge, and we don't have that in the burbs.

[00:48:35] Benji Markoff: Exactly. It's some place to like, to, to recharge, to escape, and to be like communal, right? To meet new people. I think that's one of the things, the difficulties at the beginning of the verse,I came from, New York City before this, unlike the city where you're constantly meeting people all the time,especially post exit, I found myself like, oh, I, I've basically been in my house.

and so really just I'm meeting the people that I'm already friends with, but not really, experiencing meeting new people and, being exposed to, new ideas, new personality types, all, all the stuff that makes life worth living.

[00:49:04] Connor Tomkies: have you heard of the garage in Park City?

it's super car storage artwork. But it's a third place, right?

you're

bringing people together and you're making friends that have common interests or slightly different interests. if you can solve particularly grown men past the age of 30 making new friends, you solved a major issue in America.

[00:49:24] Benji Markoff: I think Padel is, Padel really lends itself to that. because it's a two on two sport and you're, community organ organizing is a core, area where you have to succeed in order to build a successful padel club. And. The reason for that is for the most part, it's hard to find three other people all at the same time who can play.

unlike tennis, you can find one person to play with. But in this situation, the goal is you want to play, we'll have three other people like to play with, introduce you to all of that. And I think like Remedy Place has done a really good job of the social wellness side.

I don't like the true wellness,kind of retail experience, right? Or club experience where they've made coal plunges and other ship is another one in Brooklyn that's done the same thing where they've made coal plunges and sauna more, a more communal experience, right?

[00:50:14] Connor Tomkies: former Soviet Union places that used to be like the banya, did you ever

go out to like the

bathhouse?

[00:50:19] Benji Markoff: I love the Russian bath houses. The Russian bath houses, the Turkish bath houses. Those are fantastic. in the city, that's where I used to go. they didn't have, these sort of like newer, luxurious, saunas. It was always these in shambles, just look, they looked like they were 500 years old with 80 year old naked Russian men,

[00:50:36] Connor Tomkies: that's how you want it. That's the authentic experience.

[00:50:39] Benji Markoff: I only can hope and dream that one day. We can, at Hodel, we can have just a bunch of naked old Russian men just chillin in the sauna. That's

[00:50:49] Connor Tomkies: That's the dream.

Yeah, I, my wife is Belarusian. So that country like on the corner of Ukraine and Russia and we went to go visit her family in Minsk and they got in their head of oh, we're going to give Connor the American, a true Banya Russian experience. And I'm like, okay, cool. And they found this place online.

We get in this cab and It's snowing and he's going up the mountain and I see do not enter signs. And this cabbie just doesn't give a heck. Like he's just going, like he's off roading, going up this mountain, past these signs, and we get to like this warehouse, like this kind of like compound kind of thing.

And it has a guard. And it has two German Shepherds chained up, and it looks like a Fast and Furious kind of like safe house. And you're like, okay, cool. Like this is a banya. This is supposed to be like a bathhouse authentic experience. And this big old guy, completely bald, comes out in like a robe in the snow, like wearing nothing else. He's yeah, come here. Come here. I'm like, all right, where are we going? this is this going to be safe, And the family's like, all right, let's go. They go inside. There's like locker rooms that we get undressed and we They do the thing and they're like let's like give Connor like the authentic experience and like you do you know the birch sticks?

[00:51:57] Benji Markoff: Oh yeah. I've, yeah, I've done

[00:51:59] Connor Tomkies: You've done the whole thing you're pro yeah

[00:52:01] Benji Markoff: I am the, future host of a sauna podcast, the first of its kind. So I kinda

[00:52:06] Connor Tomkies: you hit your guess with the birch sticks to push the heat

[00:52:08] Benji Markoff: exactly. Patreon. I don't know. we'll figure it out.

[00:52:12] Connor Tomkies: whenever they took me to this place they have this the big guy They're like bringing the

big guy So this big guy comes in with the sticks and then he starts doing it to me and I'm like, oh I'm terrified. And then he's he jumps and does the most beautiful swan dive into the cold plunge I've ever seen a big man do barely like a ripple. And he's like, come here. And I'm like, I'm not sure if I want to do this. And, he's like, no, and so I jumped in and then he cradles me and rocks me around in a slow circle. And he's relax. And I'm like stiff. I'm like, I can't move. And, that was my, Authentic Russian banya experience,

[00:52:45] Benji Markoff: here's the beauty about all that stuff, right? the like community, interaction, meeting new people, I think is so important. And I think the other part is I don't think we like as a society or at least as Americans, I don't think we like expose ourselves to challenges and failure.

As, as much as we, as much as we really should, as much as is healthy for us, because I think that there's a certainexperience and feeling you get when you overcome an obstacle, when you, or when you, Put yourself in a challenging position or a challenging situation where success or failure is, or success is not guaranteed.

and you come out of that the other side, right? And you come out of it alive, whether you succeed or fail, right? failure and success are all relative, but yeah, hopefully, exactly. but it's so crucial to like. the human experience,

[00:53:39] Connor Tomkies: I like that tradition where like once a year you pick a major challenge to push yourself. What do you, is that called something?

[00:53:45] Benji Markoff: yeah, there's a Japanese term for it. it's so funny. I just read a book like a month ago about this exact thing.

[00:53:52] Connor Tomkies: We need to figure out the name for this thing though. There's definitely a name for it.

Hey, Benji, we are at time. How should

people find you?

[00:54:00] Benji Markoff: How should people find me? please don't.

[00:54:03] Connor Tomkies: does not

Just don't look for me. Don't find me. No. I don't know. People find me, I don't know, Google my name. I'm not sure. Go to, LinkedIn. I'm not a, I'm not big on, on X or anything else like that. Check out Padel United Sports Club. yeah. Padela united sports club. com. And then you also have this fits, which is coming podcast. And if you find it, then you're lucky.

[00:54:25] Benji Markoff: I hope no one ever listens to it. I hope I do it for the next 10 years. I hope I get to a thousand episodes of it. And I hope the only person I honestly, I probably will never listen to it because I. Like I disdain listening to myself or watching myself in an interview or TV. So I can almost guarantee that I will not be a listener of the podcast.

So no one else listened to it. Please don't, you won't know where to find it.

[00:54:51] Connor Tomkies: There's nothing you could say that would make this blow up more. please do not find this. This is a secret. It's just for me and it's on the internet for everyone else to see.

[00:54:59] Benji Markoff: Listen, if you, unless if you're into. interviewing Mark Cuban, Nips Blasting, then it's for you.

[00:55:10] Connor Tomkies: Yeah. See, that's the sell side of you. Like you, you so sold that's

a, that's definitely a

sell

[00:55:15] Benji Markoff: I guess so. I don't know. Yeah. I can't help it.

[00:55:18] Connor Tomkies: Benji. I

appreciate that chat. And,

and we'll be in touch. All right, cool. Good to see you.

That wraps up today's episode. For more inspiring stories and valuable lessons from successful entrepreneurs, be sure to listen and subscribe wherever you get podcasts. Thanks for listening. Until next time, keep pushing boundaries and writing your next chapter.