After My 3 Companies Failed, Working a 9-to-5 Felt Like The End of the World

Sean Weisbrot: Oshri Cohen is the founder of Red Corner, a fractional CTO firm. Osri and I discussed his journey as an entrepreneur, the importance of cash flow, why three of his companies failed at the same time, how he gave up on being an entrepreneur after that and for a long time before something made him realize he needed to be an entrepreneur. And the most important thing he's learned in life so far. I love these founder journey interviews because I. In them. You get to see the depth of the man or woman. Um, you get to see a lot of things about them that you may not hear in other places. You may not see it on their LinkedIn or their Twitter. You may not hear it in other interviews because we try to go as deep as we can into their psyche to understand who they are, why they are this way, and what made them change and adapt. I know you're gonna love this interview with Ri. Let's get to it. What made you want to become an entrepreneur?

Oshri Cohen: I was a shit disturber and I never got along with my bosses. Is that a good answer? I think it's a pretty good answer.

Sean Weisbrot: Probably pretty typical.

Oshri Cohen: School never really did anything for me. Right. High school never did anything for me. In high school, I was already, uh, I was already an entrepreneur. Burning, burning, um, pirated, uh, software games, music for everyone in Hi. In high school I had, I even had an order form written out, dropped it in people's. Um, in people's, uh, lockers, they would fill it up and then drop it in my locker. Right. And they knew exactly, like I had just had options. They would select the price was there, and then, you know, and I'd tell 'em, all right, this is when it'd be available. Right. And, uh, you know, I made hundreds and, uh, thousands of dollars, not hundreds of thousands, but thousands of dollars as a, you know, 16-year-old, uh, pain in the ass. That's, that was my first foray into, into entrepreneurship. But, you know, I don't have a high school degree. I have a GED. Because of, uh, in my area, uh, French is an absolute requirement. And, uh, I had a problem with my final French exam, which was a pass fail. So it wasn't from an aptitude point of view, it was from a BS government point of view. I worked a little bit right, um, for about three years in a, in an, in an, uh, uh, adult entertainment company building. As you can imagine, their websites disgusting business, never worked for those businesses. I, I'm serious, never worked for, for the porn industry. It's disgusting. Um, although it makes for really good stories. Um, and, uh, and then I worked for a consulting firm because I knew I wanted to go off on my own and I knew I needed an MBA and I didn't wanna go to school for an MBA. I'm like, oh, we'll work for a consulting firm, learn how to do proposals, client meetings, negotiations, contracts, and then design the solution sales, all of it. It was a paid, it was paid education, right? It was paid in, uh, it was paid education. Um, and from that point on, I went off on my own literally with $5,000 in my bank account, you know, while, while still living at my parents' house.

Sean Weisbrot: What kind of consulting were you doing specifically?

Oshri Cohen: So at that consulting firm I was implementing, um, business applications, so CRMs and, and whatnot. And that's before the world of SaaS where, you know, you didn't even have the internet connection for, for, for those kinds of SaaS force, for, for internet down SaaS. So, so I would implement Microsoft Dynamics, CRMI would go into companies and consult and run workshops, get requirements. Great experience to be able to translate technology, sorry, business requirements to technical requirements and technical issues to business speak. 'cause nobody wants to know, you know, when you go, when you go to the garage, you don't really care if that, uh, specific piece in the car is broken. Will the, will the car function and is it dangerous? That's all I wanna know, right? And can I avoid fixing this? For the next like three months. That's, that's what I wanna know. I don't wanna know the caliper of the disc, the fusion reactor of that. I don't care. I don't wanna know this stuff. Right. So, so I learned that early on in my career. I was 23 at the time. I learned early, early on in my career, and then I went off on my own and opened my own uh, uh, custom dev shop. Um, yeah.

Sean Weisbrot: So what made you want to go into developing then?

Oshri Cohen: Well, I was a developer. I was, I've been developing since I was 13 years old. Right. Um, and I saw an opportunity to level up the development game with, with individuals, with, uh, with someone representing the client in such a way that, um, that was education based, right. That was education based where I would, I would really explain to them the process properly where that was completely in exist and didn't exist at the time. Right. It didn't exist at the time. You hired developers and you wouldn't understand a word that they would say, because again, that was 2004, 2005, the internet was barely a thing. Hmm. Right. I mean, you started having broadband internet, so. Um, so, so that was that. And, you know, I had hired developers. I had, uh, hired sales. I had hired a whole bunch of, a whole bunch of individuals, right, to help me, help me build this practice, right, and, and execute on client work. I signed some really big clients, and then I got my ass handed to me in 2008 in the financial crash. Yeah.

Sean Weisbrot: What did you learn from that? Did you know cashflow

Oshri Cohen: is important?

Sean Weisbrot: Yeah. I, I, cashflow is more, I learned my, my last business failed because of that.

Oshri Cohen: Yeah. Cashflow is more important than your mother, man. You know that we love our mothers, but cashflow more important in the business at least. And you know what I was, I, I was, I was pulling in about 2 million in revenue. In, in my best year, and as the, you know, as the, as a first time entrepreneur and a first time founder of a business, I would never call myself a CEO or even a president because it's too small for that. Right? Give yourself the proper title, otherwise you can't be taken seriously. Um, and I overinvested, I, I took parts of the team and I said, oh, like, we're build, we're gonna build our own startup as well. Right, so we can build our own startup as well. I had built the first variant of, of what Salesforce came to be, right? And Airtable. So this web application, you can just put data in the table and that's it, and share it with people and have logic behind it, execute it, and so on and so forth. It didn't sell because nobody understood what the heck I was talking about. Because they were like, well, we have Excel and email. Well, why do we need your software, your web application? Right? And at the time, again, there was no SaaS business model, right? So the, you know, it's, I priced it at an enterprise level. Oh, a thousand dollars per user per year, or $5,000 or whatever it is that per seat. 'cause that, that was the only business model that we had available at the time. We didn't have, you know, 30 bucks a month. Right, because we didn't even think at those levels of scale yet. We we're starting to see that level of scale, but not in the B2B sphere, not yet.

Sean Weisbrot: So the most important thing you learned during the, the financial crisis was cashflow is important or is there something more important?

Oshri Cohen: Cashflow is important. Your bo, your job as a boss, as a boss, as a, as a founder, is to keep the lights on. Right. And always see the worst of what might happen. Right? Predict what the worst part will be. So, you know, when I invested in, in my, in my, in my startup internally, um, I had a year and a half of runway what could go wrong? Everything a year and a half of runway with, with guaranteed contracts right there. We had signed contracts with a penalty with everything, right? 2008 came. Within a few months, I started losing one client after another. Boom, boom, boom. They're like, we're not gonna be able to pay you. We're canceling the contract. Right. I know we have a cancellation fee. We won't be able to pay the cancellation fee. What was I gonna do? Sue them? Yeah. What was I gonna do? I could have, I could have, but I would've sold my name in the, in, in the market because I was in the Montreal, Canada market. Right. I wasn't in on an international level. So, yeah. So there's that. That's, um, that, that's, uh, that was a tough lesson to learn. 'cause I had to go back to work and I had to let go. A lot of people.

Sean Weisbrot: Hmm.

Oshri Cohen: So the business was dead. That's the worst part. Business was dead. I had overinvested. I was not the only startup. I had another one because, again, entrepreneur who can't, who can't focus on one thing at a time, right? And has to do like five freaking things. That's why I'm, I have a book that I'm writing and I have, and I've got a podcast that I'm launching and I'm doing podcasts and business and this and that, and service lines and everything, right? I have to always be super busy. My brain requires it. Um, I had built another startup called Trust or not. And what we were doing is, uh, we were scraping the web for statements made by important people, by politicians, important people, companies. They made, they make a statement and then the world could just say, I trust it, or I don't trust it. That's it. Very simple. Trust. Not trust. Think of like Reddit actually just not stupid. Mm-hmm. You know, what's the point? What, what was the business model for that ad? I, I figured I would, I would bring in enough. Traffic to generate it via ads and then be able to resell this information back to, um, back to the people that matter. So, you know, if the president of whatever, or if a minister or, or, or a public figure wanted to know, because, you know, I assumed it would be the biggest thing in the world because that's how you have to operate. Um, and because B2C makes sense at a, at a, at an internet scale. Right to, to just spread it out completely. Um, to resell them analytics. So, you know, you would see the current people who are trusting or not trusting your statement. Right. But then you wouldn't have any graphs or anything like that. And if you wanted that, then you would call us. It was really a data play and an ad play. Okay. It could have worked, it could have worked, could have worked. When was this? 2007.

Sean Weisbrot: So you're doing both of

Oshri Cohen: those companies at the same time?

Sean Weisbrot: No, I did a third one as well.

Oshri Cohen: Okay.

Sean Weisbrot: Remember the third one? I did a third one. While I have my custom development business, right.

Oshri Cohen: While I have developers coding. Were you using profit From My flight? From the

Sean Weisbrot: custom development to pay for the other two companies? Yeah. Boom. And so when the first company died, the other two companies ran outta money. All three businesses died in 2008.

Oshri Cohen: The last business was a built, was due to a school shooting in Montreal. We don't have many of those, thankfully, uh, we don't have many of those, but, um. Um, when that school shooting happened, the entire cell phone system went down 'cause everyone was trying to call and so it can, cell phone towers can only handle so much traffic, especially in 2006. Remember when it happened, right?

Sean Weisbrot: It was like

Oshri Cohen: one G or two G. Yeah. Barely right? Uh, two G, you were fancy. Um, and. So I had, I had built this startup with, uh, with a few colleagues and we were trying to sell it, and we actually did sell it, but it, the council got the contract also got canceled. I'll tell you why in a minute. Um, the, the startup was a single button and you could notify all. All the entire student body and their and their guardians, right? Guardians could be parents or guardian or whoever, right? So we call them guardians of an event of what happened in one bucket. You can type your message out. There's a fire, blah, blah, blah, blah B, this is happening, hit it and guaranteed that the message would be sent. Um. So it's SMS Push notifications. Yeah. Basically it was SMS push notifications. Yeah. But I, I had to buy a data center for that. I had to, I had to buy hardware, hundreds of thousands of dollars of hardware. Oh geez. Like if you would walk in there, you would have to wear like a lead cup. I could guarantee. 'cause there's so many antennas I was in. I was, I was, I was in the data center. And you would have racks of antennas with sim cards. Right? Just racks and racks.

Sean Weisbrot: And you invested

Oshri Cohen: in all of that before you had the contract? I had the contract already. Like it was, it was ready to go. We just didn't sign it yet. I had a letter of interest. We're like, okay, this is going down. I had a major school, uh, a major university in, in, in Montreal is interested in this. And then we, we even, uh, created another product variant for high school so that, so that schools could check if, you know, if a, if a, with a parent why a student isn't in school. Most schools at the time had. Two or three full-time people doing that work, just that work alone. So we were gonna save them a ton of money. Right? So a lot of comp, a lot of schools were interested except for one problem. Our local government cut up, cut funding for all schools around the same time, and so it became an optics issue. That's literally what I was told. It became an optics issue. They didn't really cancel the contract as much as said, we're not gonna pay you and we're not gonna sign it. But we are going to cons reconsider it in a year and a half to two years. I'm like, I don't have a year and a half or two years. Now you go right. You had already invest. You had already bought the technology. Technology already bought everything. 'cause I needed to demo it. I need to show how it worked. There was no Twilio back then. I couldn't say I couldn't hack an MVP. I needed the hardware. I needed the solve. I needed the code. Everything needed to be there. I had bought it all right. I bought everything. Right. I had committed to the data center. 'cause you needed to, there was no cloud at the time. You couldn't just go and let me launch a server. No, it was, I had to travel to Toronto and do that, you know. Right. That was, there was no, there was, there wasn't even a data center in Montreal at the time in my local area. So, so that was, uh, that was painful. That was painful. But, uh. Just like, yeah, I'm sure

Sean Weisbrot: it, I'm sure it makes you feel like 2023 is great. Oh my gosh. Because you can launch a business with, with just like, you know, a hundred dollars

Oshri Cohen: you can. And, and that's actually a kind of a big problem because people are launching bullshit businesses, right? I mean, open AI, for example, right now, now allows you to upload A-A-P-D-F file, right? It allows you to upload a pdf f file. Yeah. Uh, and talk to it. How many startups did that just kill startups and businesses, right? There are so many that came up and said, Ooh, we're gonna parse the PDF and yeah, and we're gonna let you chat with your PDFL. Great, fantastic. Small, tiny, little problem, right? They're using the open ai. API and OpenAI saw that and be like, we can do that. That's it.

Sean Weisbrot: That's like what Amazon was doing. Yeah. Oh, we're gonna let you have your own brand on here and then, oh, this brand's doing great. Well, we could do that too. Sorry, brand. Bye-bye. What? It's called

Oshri Cohen: Amazon's Choice or something like that, or Amazon Choice. What is it called again? Prime Choice. I dunno what

Sean Weisbrot: I think. Amazon Choice.

Oshri Cohen: Yeah. They just undercut the seller, completely run 'em out of business because they, they sell it at way cheaper and ship it much faster. And that and, and probably manufactured

Sean Weisbrot: better.

Oshri Cohen: Probably

Sean Weisbrot: they might even be using the same manufacturers in China. They might, they probably are, but 'cause they can buy in bulk, they can negotiate better deals.

Oshri Cohen: Yeah. I mean, it's Amazon, right? What are they sitting on? A billion dollars of free cash flow. They could, I feel like that's too low. That's you think so?

Sean Weisbrot: Of actual cash in the bank? I don't know. Maybe, maybe they need, I mean, apple has like 200 billion in cash. I feel like, I feel like Amazon has more.

Oshri Cohen: Can, can we agree though, that this is an a, a, an obscene amount of money for any company to have? It's just, it's just obscene. It's like, it's nuts.

Sean Weisbrot: It's nuts. I mean, um, Berkshire Hathaway has about 200 billion in cash. Is it cash or is it investments? He sold a lot of investments and he is sitting on cash and he is buying some bonds with it right now.

Oshri Cohen: Yeah.

Sean Weisbrot: But otherwise, he's sitting out of the market looking. He's, he's sold out of things that he doesn't believe in. Like, I think he's sold half a billion in, uh, HP recently. I think he completely got out of his, uh, hp I think it's the consumer, the consumer side of hp. HP's still a thing. Yeah, they've got an, they've got hp, which is enterprise and they've got hp, which is consumers. They, they actually split the companies.

Oshri Cohen: Yeah. 'cause consumer is bullshit. Like nobody who buys a, an HP computer anymore. Right. People do apparently HP data centers. Sure. You know. High speed computing. Oh, well, HP has

Sean Weisbrot: printers.

Oshri Cohen: Oh, hp the

Sean Weisbrot: printers. Right, right, right. People are still buying their printers and they're still buying their SaaS or not really SaaS. They're buying. They're buying their has. Right. Hardwares. They are selling. I kid you not, I don't know if you have a printer. I haven't owned one in, in a very long time, but my parents pay a monthly fee to get ink mailed to them. What? From hp. That's nuts. I I would never do that. I would, apparently it's cheaper than if you bought it directly from like OfficeMax.

Oshri Cohen: You know, I, I have, I have a photography, uh, like photography grade printer. It's massive. It can print like, you know, like 18 inches, right. Wide. Mm-hmm. Um, and, uh, yeah, I mean, you know, it's 12 cartridges and each one will cost me about 150 bucks. But I can print 2000 photos with it. So you know, it's a different ball game. It's nice Ink. Ink is expensive. Ink is exp expensive. That's where they make their money, right? The printer is, yeah. That's why they turn it into a monthly subscription, which is ridiculous. Which is completely nuts. Like BMW and their, and their subscription model for bloody air conditioning or whatever it is that they're, that they've decided to do. I think it's

Sean Weisbrot: seat heating.

Oshri Cohen: Oh, seat seat heating. Yeah. I'm not paying for that. No, no, I think, I think that's just an overreach.

Sean Weisbrot: Yeah, I think, yeah, you wanna have like something like serious satellite. Okay, fine.

Oshri Cohen: You know? Yeah. You know what? I would pay a monthly fee. As a subscription to Tesla, I don't have own one to Tesla because they continuously improve the software. I'm like, great, I want the all, all, all your latest software. Just give me new, the new stuff. As soon as you get it totally fine by me. I'll pay for that. Because every, every friend that I have that has a Tesla, they they swear by. It's like, oh, we have a new feature. Ooh, what do we do now? What can I do now with my freaking car? Right?

Sean Weisbrot: Yeah. So 2008 seemed like a pretty rough time. Yeah. You said you ended up, you, you, you shut down all three businesses. Mm-hmm. I'm assuming you ended up getting, so the, the first business was generating, you set up to 2 million a year. Did you, were you able to take anything out of the bus, uh, any of those businesses or did you just lose all of the assets and all of the cash, all of it was just gone. Did you end up zero, you back to the square one? I,

Oshri Cohen: I sold off some of the hardware. Um, I incurred heavy. Heavy losses on my, on my company's, uh, um, balance sheet, right. For tax purposes. I don't think I paid income tax for a whole year after, for like six, seven years afterwards because they were just like against losses, right? So I would get massive, massive, massive returns back. But I was also burnt out. I didn't like, I didn't want to have anything to do with it anymore. I was completely burnt out. It was an emotional wreck to, to have everything you built. Right. And I had just gotten married and we wanted a child. And like everything. And I, and I was, I was working ev all hours of the day and night, and I was just completely stressed outta my mind. So it was, uh, it was, uh, it, it caused a lot of mental health load. Unfortunately, I. As, as is life, you know?

Sean Weisbrot: Yeah, I totally understand that. I'm, I'm still, it's been over a year since my company died, and I still don't feel like I'm like, completely, uh, healed from that. No,

Oshri Cohen: and it's your baby. It's you, you put so much effort into it, right? You put so much effort. Like my, my new, my new consulting business, red Corner, I'm putting a tremendous amount of effort. I haven't seen, I haven't had a paying client in two months because I'm building this, this, this practice, right? You know, it takes a lot of effort, lot of effort to, to spread the message, marketing everything when you're doing it on, on your own with limited cash. But it is what it's, that's the founder life, I guess.

Sean Weisbrot: So you went back to work? Mm-hmm. You were you what? You were a CTO of some company or what were you doing?

Oshri Cohen: I went in as a director of engineering. Then for a couple of years, the company was a small startup. It was fun. It was in data analytics and big data and whatnot, all sorts of fun. Why not? I had that background anyways. Grew the team and whatnot, they got sold to a, to a larger company, right? So the, the owners exited and then the owners got fired promptly afterwards. So when, you know, when every, when, when, when your bosses get fired and, and, um, it doesn't give you a lot of confidence in your, in your ability to stick around, right? It doesn't give you a lot of confidence. And so I had left afterwards, I became CTO for an EMR company. Um, loved the job because it was healthcare. It was my first foray into healthcare. I'm like, wow, with my hands, I can actually help someone, you know, six, these six degrees of separation, but I can still help someone. I'm not just making other people money or making myself money. So it's a very different paradigm to be in. Right. I loved it, but I had to leave my job. I had to leave that job because I was told that I was not allowed to hire end people in the company. I. Right. Everybody gives me the same. Yeah, like this is like 2008. Uh, this is 2010. Right. In Canada. In Canada. And I'm like, why was that even a discussion? I don't know. Like this is, I see a profile. I'm like, you look good. I meet you. I'm like, okay, you're smart. I'm hiring your, I could. I. I could care less if you have tentacles. I don't give a damn. It makes no difference to me in any way shape. Well, if they have tentacles,

Sean Weisbrot: they probably wouldn't be able to have the sensitivity to type properly, so.

Oshri Cohen: Right, fair enough. But hey, nowadays you have to give everybody a, you know, give 'em a pen in the mouth or something. I don't,

Sean Weisbrot: can't say I've met a human that has tentacles, but all right, let's, I'll run with it. Let's go, let's

Oshri Cohen: run with it, you know? But you know, um. I grew the team, but when I was told that, I'm like, yeah, I can't, I can't stay there. I'm the head of the co, I'm the head of technology. If I allow this to happen, then I believe in it right out of complete chance. The old company that I, that, that I was working for as director called me. It's like, we wanna reestablish the startup that we bought and we dissolve. We wanna reestablish it back, um, with you as the director of engineering. Um, we brought back the old owner, one of the old owners, and he's CTO now, and, you know, let's talk. I'm like, okay, great. You're giving me budget, you're giving me a team, a product. I already know, a team that I, that I, that I can rebuild. Why not? It was nice and easy. It was one of those places you left at 4:00 PM and you took a two hour lunch and you arrive at like nine 30. Right? Because it's, uh, you know, it's your old school corporate environment. It was very relaxing. Very relaxing. Mm. Because I just came from a startup that I was pulling 12 hour days. Right. You know, I was like, uh, I was playing with my kid and, uh, I, I had a baby at the time. I was, um, I was changing him and having a business call with, uh, with the CEO. Right? So, um. So after that, I had left and I stayed there for two and a half, three years. That was my longest stint. That was the longest stint I've ever had, right? Mm-hmm. Um, I got fired from that job though. I got fired hard and fast from that job. Um, remember the statement that I was a shit disturber, so, right. And, and entrepreneurs do not belong in a corporate environment. It is completely. Illogical to have an entrepreneur, creative free thinker in, in, in an army of drones that have no soul, right? They just, you know, they shuffle around doing their job and they don't think. They're waiting for someone to think for them. It's nuts.

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Oshri Cohen: the CEO loved me, but the CTO did not like me at all. He didn't, and he's the one who hired me, but he says like, no, it's, you know, we have a B2B product and, and so on and so forth, and I put up proposals. I'm like, how can we make this a massive business? Right? I wrote a whole business plan submitted to the CEO. The CTO saw that as going over his head, and because he had ownership in the company. He voted, he basically voted me out. Right.

Sean Weisbrot: Why didn't you go to the CTO?

Oshri Cohen: Uh, I did go to the CTO. He didn't believe in it, so I'm like, okay, hence. So you went around him? I went around him because I'm like, okay, well you're not gonna do anything about it. I'll do something about it. Went to the COO, met her for lunch, then went to the CEO, met him for lunch. Pushed it, I got invited to the, I got invited to the table right to uh, I was given a seat at the table with all the other executives. I was director of engineering. Right. Uh, the CTO saw that as, as, uh, as a, uh, as a problem because he didn't want me there. As his, as his life. Right. Because I was gonna make his life difficult because I was gonna make him actually do work. I know, right? I can think about product.

Sean Weisbrot: Wow. Why would they, so then, why, why did they bring the original founder back if they had already spent several years and moved on it? It didn't make sense to bring him back.

Oshri Cohen: He had shares in the company and I guess they gave him a job so that he wouldn't, uh, he wouldn't, uh. Sell his shares or he would sell. Right. And they wouldn't have somebody, uh, I guess you can do that in the secondary market. You can sell your shares to someone. I have no idea how that works. Um, I've never exited. And the company

Sean Weisbrot: was public?

Oshri Cohen: No, it was private. It was private. So I'm I'm sure you, there was a way of selling your shares to somebody else.

Sean Weisbrot: Yeah, I mean, when I was doing all of that with my investors, I had written out, uh, like the terms of the agreement where if we were private still. And they wanted to sell their shares. They would have to offer it to us first.

Oshri Cohen: Oh. Write it first for people. And if we said we

Sean Weisbrot: didn't want it. Okay. Right. If we didn't want it, then they could sell it to someone else that was part of the team or another investor. Mm-hmm. And if, and but, but we would have to approve them buying it.

Oshri Cohen: Yeah. Yeah.

Sean Weisbrot: If that person wanted it.

Oshri Cohen: Yeah. Right. Of first refusal. You have, you have. Yeah. They do that in, they do that in, in, in real estate a lot. Um, but anyways, whatever, whatever their, their terms were, their terms were, and the guy's still there raking in a massive salary doing bleep all because a marketing agency doesn't need a full-time CTO, so, you know.

Sean Weisbrot: Yeah.

Oshri Cohen: It just doesn't Lucky guy. Yeah. Doesn't need one. So he is milking it until he's, until he decides to sell, making a couple of hundred thousand dollars a year. Right. So I got, I got pushed out of that business, but the CEO really liked me. And so he gave me a two month severance, which is pretty, what was standard? No. Uh, two weeks. Barely. You're lucky if you got two. Yeah. Two weeks was the minimum by law that you could give, but two months with and and kept my health insurance for another six months or eight months. Right. Even though, you know, in Canada we have health insurance by the government still, you get a little bit more of those helps. Um, took a month off and started looking for work. Found another job that was fantastic in a SaaS. I was writing code, but I wasn't, I wasn't in leadership. 'cause startups don't need like a leadership hierarchy at the beginning. You don't need directors and managers and whatnot. You need developers and then you need the founders. That's it. They, they recruited me. So the CEO found me on LinkedIn 'cause I was writing a book and whatnot and uh, and he's like, I like your style. Let's talk. And so I was with them for about six months before a friend was CTO for another company from a hypergrowth company brought me in. That job lasted for six months also. So two, two jobs. That lasted six months because I moved. I'm like, I, I, I, I like coding, but this is the end of my career if I start coding again. Like, I don't, I don't wanna be coding. I haven't, you know, I'm good at what I do, but I want to be in leadership. This is where my career trajectory, I wasn't thinking of going off on my own yet. Right. So I'm like, maybe that time is gone in my life. Right. And that company acquired another company that, and, uh, replaced me, just replaced me like that, you know, unceremoniously, um, had a couple of other jobs in between that are inconsequential. But, um, that's when I decided, after, after being laid off, that's when I decided to go into business again. That's, I had some money saved and I'm like, you know what? This is the time to do fractional CTO. And here we are.

Sean Weisbrot: Makes sense. Yeah. After my last company ended, I kind of found myself in a position where I'm like, I have no idea what I wanna do. Because I'd spent four and a half years as a startup founder. I'm like, what am I supposed to do after being a startup founder? Like I can either find another, I found another company, which like I was not emotionally, you know, ready to do that. Or maybe I can get a job working for someone, but like I haven't worked for someone for 10 years, so I don't think I am probably in the best position mentally to like work for somebody else. And so I kind of just spent a few months just doing the podcast, interviewing some people and traveling around and, and over time just kind of realized, yeah, you know, the thing that I did well, that I made a lot of money at was consulting. Screw it. I'm gonna start consulting again.

Oshri Cohen: Consulting is a fantastic business. It really, really is. If you can productize your service right. If you can productize your service and add a and and make it into a flat fee model, it's so easy to sell. It is easy to sell. It sells like hotcakes. My fractional CTO business, I must have generated something like close to 500 k and in the first six months, right? Not the first six months, the last six months, the first six months, I made no money. 'cause I was, you know, small contracts here and there until my name, I gained some name recognition. But, um. Uh, how can I say, um, what did I want to say? Yeah. And because I had productized it, I had, this is the flat fee every month. That's what you pay me. This is what you get. Nice and simple. Contracts are a couple of pages long. That's it. You really don't need much. Right. And yeah, and I found, I found a, uh, uh, a market that is, that is open to. To hiring a fractional CTO. And it's not always startups. Startups sometimes, but I realize even small businesses needed it, not just startups.

Sean Weisbrot: So there was, what, about eight years or nine years between when you started working for people and when you decided to go back into Yeah. Your own business again.

Oshri Cohen: And, and, and you know what? Throughout that time I was, I had depression, I had depression and anxiety. Like working for someone I felt like was the end of the world. It was the end of the world and let's explore that. And I've been a CTO, I've been director, vice president of software engineering and at multiple startups and companies. And I was looking for work and, and even when I decided to go off on my own, I'm like, I'm still gonna look for work. Maybe I'll find Right. And I had many, many interviews. 'cause I have a very, very good. Uh, resume. I very, very good experience. And then I realized that I wasn't getting the jobs, I just wasn't getting it. Why wasn't I getting it? Because I didn't know one specific tech, uh, technology, right? You know, I was, there was one company that was bringing me into be a, a, a network, CTO, like a CTO for all of their companies, right? Mm-hmm. So very high level in New York, the whole thing, right? I may have even had to move there, potentially. And, um, that was pre, uh, that was Post Co. That was Post COVID. Um, and, and I didn't get the job because I didn't know something very specific in AWS and I'm like, this is, but that's not A-C-T-O-A-C-T-O is leadership. It's like a, it's like asking a founder, you can't be a founder 'cause you don't know that Excel macro. But that has nothing to do with anything. I can learn that that's not a problem. I know that I can need to, I can use Excel. I don't need any more, any more information than that. Right. I don't need to be an expert in everything. Yeah. And that's when it started to key in. Most companies don't understand what A CTO does.

Sean Weisbrot: Not just that, but corporations don't realize that their best employees are the ones that know how to teach themselves. Whatever it is. They're, they have a gap in, which is what most founders are really good at. Exactly. Because for example. I, my last time doing the consulting company, I didn't have social media. I didn't have a website. I didn't know how to build any of that stuff. Yeah. I've had to learn now how to do all of that stuff 'cause the world demands it. But I've actually been able to create systems for myself about how I can go for idea to launch much faster. Where before I didn't have any of that, those skills. Mm-hmm. But now that I'm working with another company as an advisor. I am. I've taken them from idea we're going to launch in the end of November, but I've basically pulled them through the whole process and I've systematized it as I've done it. I didn't know how to do this a few months ago. Despite all of my experience, I taught myself how do you go from idea to launch in a systematic way? And so I had to document everything as I did it. If someone hired me to work for their company and take them from idea to launch, but I'm not the founder. I wouldn't have the power to do any of that and to make those decisions and to document that stuff. Or if I did, they wouldn't appreciate it. But now with this experience, I'm thinking about launching an accelerator where I would help businesses. You say, come to me with your idea. I'll take you to launch. You'll give me equity. If I like you, I'll invest cash for more equity.

Oshri Cohen: Yeah. That's actually very smart,

Sean Weisbrot: but the focus would be on service businesses, because that's what I know I'm good at. You asked me to, to make a business accelerator for a SaaS or an E-com. I don't know how to do that. I can do it for a service business.

Oshri Cohen: Interesting. That's interesting. It's, you know what, that's actually very much needed. We've, we've, we've been, we've kind of been stuck in this in startup plan for a little while. You know, startups, oh, that's the only way to make money and whatnot. There's a heck of a lot of boring businesses, boring service businesses that could bring someone in five, 10 million a year, right? I'm designing my practice, red corner, right? My agency, my Al CTO agency. If I top out at five 8 million of revenue a year, I'm good. I don't need to grow any more than that. I don't need to bring in partners. I don't need to do anything. I'm happy even for less than that. Heck, bring me 2 million a year in revenue and I'm good. It will sustain a very luxurious lifestyle. It'll, there'll be money in the bank for years to come. It'll be real estate and investments and everything, and that's the reality of life. You know, to focus on, on making billions of dollars. Oh, I need my a hundred x multiple. Okay, let's relax buddy. You're not gonna take over the world with your dinky little PDF chat app. Right? That's, that's it's, it's a lot of startups now, especially because it's so cheap to launch a startup. Have devolved into, uh, quick fixes. It's like, uh, you know, uh, easy money skills. We call 'em micro SaaS. Call 'em, whatever you wanna call 'em. I have a micro SaaS right leaf.page, which is, uh, which is a landing page for professionals. I. You know, it makes a little bit of money here and there, and that's it. I bought it off of someone for a couple thousand bucks and, and I maintain it and grow it, and slowly but surely it grows organically, frankly. It just grows organically. So, you know, so, so that's it, that's, that's the, uh, that's the gist of it. It's. Man, there's so many ways of making money. Hey, buy a laundromat for all we care. Go buy a hundred laundromat. I'm good. Make it a better,

Sean Weisbrot: I have no desire to be involved in all that. I've, you know, when I was going between for the last year when I was thinking like, what am I gonna do next? I took all these courses about mastering marketing, mastering sales, buying laundromats, starting your real estate fund. I learned about all of it, and I was like, I, that's just, none of it is me. I, the thing that makes me happy, the thing that wait, that I want to get up and do every day is help companies be better at what they do.

Oshri Cohen: That's what makes me excited, helping founders. That's what makes me excited as well. That's literally, that's my, that's my, my happy place. I take over a team, a rack tack team of developers for a client. They don't know what they're doing. They're making mistakes all over the place. I leveled them up. I raised them up to be amazing people that. To the point where they do not need a full-time CTO, they will never need a full-time CTO. They'll need a fractional one to come in and just, you know, steer the ship. You're going to, yeah, go five degrees in this, in this direction and you'll be fine now. And that's it. That's all they would need. Because once you level up your people, once you teach your people how, how to think for themselves, how to be creative, how to take controlled and educated risks. You don't need someone to go in and think of strategy all day long, because even founders, we don't, we don't think of strategy all day long. It's, you know, we'll have half an hour with a scotch and on a whiteboard and figure out how our, where our business is going for the next two years and a couple of hypotheses and that's it. Right. That's the reality.

Sean Weisbrot: Yeah. The, the team that I'm working with now that I'm taking to launch, they were like, it was like three months ago. They're like, okay, we're gonna do this and we're gonna launch in June of next year. I'm like, you're a headhunting firm. Why do you need 10 months to launch? You need 10 And so to launch Well, yes, but I, I said to them, you know, we, we need to have certain systems in place, so there's things that we need to do. Mm. Right. We need to do our branding. So I took them through branding. Okay, well now we know our branding. We need to go through the website stuff. Well, I mean, there was things before that, right? Well, the, the product, the service, the ideal client avatar. So I've built out documents for all of this, and it's like, okay, well what's the website? Gonna look like, what? What are the pages we need? What's the copy that's gonna be on each, on each page? Yeah. Right. How are we going to brand that? How are we gonna design it? How are we gonna do it? So we're doing all that now. But then, okay, well what's our sales process? What's our marketing process? What's the software that we're gonna be using? Who are the people that are gonna be running these processes? Yeah. How are we gonna manage all of these things? How are we gonna get clients? How are we gonna. You know, sell clients. What are the messages we're gonna use when we, we, we message them on LinkedIn, right? What's the, what's the high level, what's the mid-level, what's the low level of every single, single thing that this company needs to launch? And that's what I'm, I'm basically doing for them now because I, I realized that they had an idea, but they didn't know how to launch it. And so I said, well. This isn't what I signed up for. I signed up to be your advisor. Yeah. But you need this help. Therefore, I have no choice but to help because I've committed to helping you. So you're getting a cut out of that one. Oh, yeah. Uh, I have, uh, equity with this. Nice. Because they don't have the cash to pay. Yeah. Which is fine. No big deal. I would, if I could spend three months at a time with one company, getting them from idea to launch and have equity in every one of those businesses, I. I'd be very happy with that.

Oshri Cohen: So equity. So equity in a, in a startup, that's a digital product in a service

Sean Weisbrot: business.

Oshri Cohen: Yeah. But, but equity in, in startup land for your little dinky web, uh, you know, startup and whatnot, even if you raised 50 million or whatever it is, is a lottery ticket, you're gonna win or you're gonna lose. You're 99.9999999% going to lose. It's worth less than toilet paper. That's the reality. Yeah. That's

Sean Weisbrot: why, that's why I'm interested in service businesses. Yeah. Where the equity turns into monthly or quarterly dividends, boom. Based on revenue. Yes.

Oshri Cohen: So equity in a service business that has an actual path to profitability and an immediate path to profitability. Right. That's the reality. Oh, a headhunting firm. Yeah, sure. I've done recruiting in the past. There's a lot of money to be made there. And if you have equity and now you're going to get paid dividends for the lifespan of the company, well, okay. This is, that is a fantastic model. That is Fanta, because service businesses have to be profitable within their first year. They must be otherwise, or at least break even. At the very least. Break even. Right. If they do it badly, that's that's the thing. So yeah. Absolutely. That's fantastic. I love it.

Sean Weisbrot: So what's the most important thing you've learned in your life so far?

Oshri Cohen: Oh my gosh, so far. Um, don't underestimate, um, your ability to sell like sales is, I don't care who you are. I don't care how good you are at your job, you need to be able to sell. Like, you can't not be able to sell if you can, if, if you have, uh. A skill in selling, use it. That's the reality. Second lesson is don't be too cheap. Don't charge less than you. You, you, you should, because a lot of companies and a lot of clients will. We'll respect the higher price point. So I'm actually te, I'm actually testing this out for my consulting firm right now. So I have this whole, this whole service line where, where I represent clients who are hiring a dev agency. That's it. I'm a technologist. You're gonna hire, you wanna hire a custom dev agency. I used to be one. I know how, how, uh, predatory they can be right in order to raise their billable hours. And they're not. And I know how, they're not going to give you the best advice. They're never going to tell you, no, we should not build this because it'll cost them a hundred or 200 or 500 K. And so I represent the client and I'm like, I will represent you and I will tell you what you need to build. Not the dev agency that wants to charge you more, right? So I'm here to protect your wallet. Fantastic business, I think it is. I'm gonna have a massive Google and uh, Google campaign, but I'm gonna try landing page, uh, six landing pages at different price points, starting from $1,000 a month. To $5,000 a month. Right. We'll see which one converts the most. I have a feeling I'm gonna fall somewhere in the $3,000 a month. I think a thousand dollars is too cheap. 5,000 is too much. I think I'm gonna fall in the $3,000 range, but we'll see. Right. And and even the marketing company that's doing that right now is, uh, agrees with me because like they did it for a plumber. Just a plumber. Right. They tripled his rate and. The variant with the, with the three times the price, the hourly rate got more leads than the one that was cheaper, the cheapest because people respected the higher cost.