Deciding to go to business school, changing careers, and selling 2 businesses with Ido Deutsch (VP of Growth at Agentero)

Callan Harrington 00:01
You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here today.

Callan Harrington 00:20
I'm really excited. We're joined by Ido Deutsch of Agentero. Ido is the VP of Growth at Agentero, so I want to sit here and welcome Ido. Welcome to the show.

Callan Harrington 00:30
Hey, hey, Ido, thanks for having me.

Callan Harrington 00:33
Yeah, absolutely. So, we've gotten to know each other, so this is exciting. I'm excited to kind of dive into your career. So tell us a little bit about what you're doing at Agentero.

Callan Harrington 00:47
Yeah. So at Agentero, I'm the VP of Growth. What that means is that I lead the team that does everything other than product and engineering. If you think about it, it's the whole go-to-market—marketing, sales, support, success, finance, operations—everything. It’s about trying to align everyone to similar goals.

Callan Harrington 01:10
Absolutely. So you're covering pretty much the entire buyer’s journey, correct?

Callan Harrington 01:14
Yeah, pretty much. All of it. Marketing, sales, customer success.

Callan Harrington 01:17
So before we dive into Agentero a little bit, where did this all begin? How did you get to where you are today?

Callan Harrington 01:25
Good question. Let me go a couple of years back. So I'm originally from Israel, born in a small town in the southern part of Israel. From a very early age, I played soccer. I found myself really enjoying it and was really good at it. I was a goalie, so I played professionally when I was 14 and started playing for the national team. I played for the national team from 14 to 18. Playing soccer competitively and being on a team sport, being the goalie who sort of sees the whole team, built my character. Having reflected on it for many years, I think that's something that's deep within me.

Callan Harrington 02:11
You played for the national team, like the team that would play in the World Cup?

Callan Harrington 02:15
Yes, I played in the World Cup for the U-17 and U-18 Israel teams.

Callan Harrington 02:21
Gotcha. Wow, I had no idea. That's really cool. So, what does the career path look like going into that? Once you get to 18, do you have to try out for the national team to make it? How does that work?

Callan Harrington 02:36
Yeah, good question. So, there is one national team, and you have the under-14, under-15, 16, 17, and 18 teams. I played for all those teams. But once you turn 18, you play for the one national team that gets all age groups together. When you’re younger, you play with your age group until you're 18, but after that, you play with all age groups. I didn’t make it to the varsity, or the adult World Cup Israel team, but I played for all the younger teams back then. The other thing is that I was a goalie, and there’s only one or two spots on the team. When you compete against all age groups, the probability of actually getting in is very low. So I didn’t make it there, but if I had, I would probably have continued being a soccer player until I was 30 or 40 or something like that. I’m grateful for how it built my character and helped build who I am today, but I’m also happy that I’m not there anymore.

Callan Harrington 03:35
Got it. This is fascinating to me. I had no idea, of course, but was that your plan? When you were 16, 17, 18, was the plan to play professional soccer?

Callan Harrington 03:46
Yeah, since I was nine years old, it was all about soccer. I mean, I went to school and all that, but everything was soccer. In Israel, you have to go to the military when you are 18 to do your service for three years. But because I was playing for the national team, I got to do the service while still playing soccer. But it was all about that—if I missed a practice, it would be like the end of the world. My whole life was centered around soccer. I played until I was 21. I played for the national team until I was 18, and all those years, I also played for my city team. But when I finished with the military and got discharged, it was a point in life where I had to ask myself, "Do I want to continue with this?"

Callan Harrington 04:25
Gotcha. How hard of a decision was that? Something you've done your entire life, and now you're just like, "Okay, I’ve got to go into a completely different path." How did you come to that decision?

Callan Harrington 04:43
That's a great question. It was a tough decision. It took a couple of years. You know, growing up playing soccer in very competitive environments, I always wanted to be the best, always wanted to be at the top, and I was usually there. But when you're not there, you're trying and trying again and again. But at some point, you have to be honest with yourself. For me, I think I was probably more mature than most 21-year-olds at that time. I had this moment where I was sitting at home thinking, "What should I do? Should I keep trying to get into this top 1% in soccer, or should I go and study?" And I decided, "I should probably go study." I didn’t leave soccer cold turkey; I was still playing and doing some of the, you know, SAT-type things in Israel and all that. But when I got to the university, the one I wanted to go to, I knew I had to make a decision. It was easier because I was already 70% there in my mind, so I just made the jump.

Callan Harrington 05:55
I’m curious how much that decision helped you later in life and in your career because that's a really tough thing to do. Did you find that it helped you later in your career?

Callan Harrington 06:08
So, I think there are two things. One is that I’ve always been competitive, always trying to do more and do better. But there's also a part of me that is very aware of not being a perfectionist and not letting perfectionism be the enemy of good. So, when you need to do the 80% and not the 100%, it's fine. Let’s leave it there. I find myself thinking a few steps ahead all the time, like, "Is what I’m doing today good enough? If it is, I'm moving forward." That approach helped me a lot in my career. The toughest decision in my life from that perspective was deciding to stop playing soccer. But once I made that decision, everything else sort of layered up from there. I learned to not let perfectionism be the enemy of good. I would try to win, do the best I can, evaluate things from an outside perspective, and say, "Is this good enough?" and move on.

Callan Harrington 07:18
I think that’s great advice. So, you decided to move on from soccer and go to school. What was that transition like for you?

Callan Harrington 07:26
For me, it was easy. The decision was hard to make, but once I made it, I just went with it. I always try to do my best, so I went to school and tried to be the best at school. I went to a private school in Israel, and I had to work throughout the entire time to pay for it. So, it was a challenging combination of working really hard every day, trying to pay for everything, and going to school altogether. It was a different challenge—excelling at school while trying to make everything work together. I wasn’t the best in school, but I gave it my 80%, and the rest was about making things work so I could actually work, live, and maintain the cost of living.

Callan Harrington 08:23
That makes total sense. So shortly after, it looks like you founded a company right after you graduated. Is that correct?

Callan Harrington 08:31
Yeah, so there are two things there. As part of my nature, I’m competitive and always trying to do things on my own. Even while I was still in college, I worked in bars and restaurants to make a living. Eventually, in my last two years of college, I also opened a bar.

Callan Harrington 08:49
I co-founded the bar with three other friends I met along the way. It was a great experience—my first real ownership experience. I always wanted to start things on my own. I was working in bars, and I thought, "We can do it better. We can create a better place and make it work," and we did. We were very determined and had a lot of fun.

Callan Harrington 09:16
So that was a lot of fun and also a great experience. Building that bar helped me understand how business works—how you need to bring in money, make it work, and if not, you need to bring more money from your pocket. Understanding all the mechanics of how business works and what it takes to make it grow was a super valuable experience. I did that for two years. I think I sold the place just right after graduating. It was a really good experience, but this was my first real experience in building something from scratch, understanding how business really works, and what it means to build something from the ground up.

Callan Harrington 09:49
Then I sold that business when I finished school. I also had to do an externship and get certified as a lawyer. Yes, in one of my darker stats, I’m also a lawyer back in Israel. Not proud of it, but I am.

Callan Harrington 10:16
So I did that, but there was something that always bothered me when I was working in bars and restaurants. We always had delivery. I would work in the bar, managing the restaurant, and the kitchen would do deliveries. Today, with things like Uber Eats, it’s simple—you go on your phone and order. But back then, smartphones were just starting to come out. Most people would call the restaurant. There were websites like GrubHub, but in Israel, we had a few websites that would send orders to the restaurant via fax machine. The fax machine would sit on the countertop, receiving orders, and we’d take those pages and put them into the system.

Callan Harrington 11:14
Now, imagine a restaurant that serves lunch at noon, and everyone wants to order at the same time. All those orders would go through the fax machine, so there would be a queue. We would only receive the orders at the restaurant at around 12:30 or 12:45 because there was a queue of faxes before that. It was crazy. Running the restaurant that way was crazy. I thought, "Why is no one doing anything about this?"

Callan Harrington 11:49
Around that time, tablets started to become available. The iPad had launched a year before, and they were becoming cheaper. I thought, "Why can't we put an iPad in the restaurant and just get the orders there?" I talked to some restaurants and websites, and they were like, "Yeah, that would be super helpful." So, I realized there was a problem that I personally experienced, and I saw a simple solution out there that I could solve. I knew someone who was more technical than I was, so I asked him, "What do you think about this?" He said it was simple, just do X, Y, and Z. So we started something.

Callan Harrington 12:34
We worked for three or four months, taking off-the-shelf stuff, building some software and hardware together, and putting it in the restaurant. They loved it. The restaurant loved it, the website loved it, and we scaled that for about two years—really working hard, building everything from scratch, hiring a couple of people, not raising money, bringing all the money ourselves. I didn’t really know how VC worked back then, how to raise money and all that. But yeah, we built this company, which I think was the biggest achievement of my life—building something from scratch, not knowing a lot, identifying the problem and solving it, finding this product-market fit, scaling it, and eventually selling it, exiting from it. So all that was a really great experience.

Callan Harrington 13:30
So you had two exits by 28?

Callan Harrington 13:33
Yep.

Callan Harrington 13:34
And then from there, you moved to Boston. What led to that move? It sounds like you were kind of on fire for what you were doing. What kind of spurred on that move?

Callan Harrington 13:43
Yeah, good question. I had a really good time with the company, and around the same time, I got married, which you wouldn't expect. It was a crazy time—I didn't have time to sleep, but somehow I got to meet my wife and got married. We're still rooting for one another. The reason I moved was that my wife got accepted to school in the US, in Boston, for business school. I had done my thing, and she was very supportive of my previous company. You probably know how it is when you start bootstrapping, you don’t have money, and you're not making much money—it’s really tough. But she was very supportive, so when she wanted to make a step forward in her career, I jumped in and said, "Let's do it." We moved to Boston, and I moved with her. I didn't have a lot of plans—I had something waiting for me, a friend that I knew, and I was working with him on something, but nothing really solid. So I moved like a clean slate and said, "Let's go on this opportunity and see what we can do."

Callan Harrington 14:55
Gotcha. What was that shift like, just in general, from Israel to Boston?

Callan Harrington 15:02
That was a big change. First, just the weather. Moving from Israel to Boston, I think it was 2014, and that was the year they still call "Snowmageddon." It was the worst winter ever in Boston for the last 100 years or so. That was the year I moved from Israel, which is a desert country and super hot, to walking the streets with walls of ice on both sides. I thought, "Yeah, not the best decision to move to Boston this year." I didn't think I’d stay in that cold for much longer. The weather was tough, but the other challenge was moving without having a specific thing to do, trying to figure things out on my own. My wife moved to her school, so she had a lot to do. I was part of the community, but I'm used to doing things. I'm a builder, a doer—that's how I define myself. So trying to figure out being there, being the supportive part, but not really having a lot to do, was hard on the self-identity, trying to figure that out on my own. It was a tough time, but it was also a lot of learning for me—figuring out how I could be in that situation, what I could learn, and how I could grow.

Callan Harrington 16:45
Before you get there, why was that tough?

Callan Harrington 16:48
You know, when you're used to always doing things, executing, and running, your whole day is filled up with things to do all the time. So I don't know how I met my wife because I wasn't sleeping—I was working 24/7, building stuff on my own. Then we moved, and she's going to school, and I'm home. I had someone to work with on a freelancer basis, helping with some support and advice, but it wasn’t really filling up my days. I was like, "What should I do? Boring. Why did we move?" Your self-identity kind of shifts—you're like, "What do I do next? How do I build myself?" Because you're moving to a new country where your experience isn't really valued—they don't know what you've done and who you are. So that was a tough time, a challenging time, figuring things out on my own. But again, reflecting on all that, it helped build character for me—getting to know myself better, understanding who I am, what I want, and how I want my life to look.

Callan Harrington 18:17
I'm digging into this a little bit, but this is interesting, and I’m sure other people might relate. Obviously, I can't relate because I'm from Ohio, and I'm still in Ohio. But what did you do? Because just hearing what you're saying—you played soccer on the national team, so no doubt people knew who you were. I'm not saying everyone in Israel knew who Ido is, but if you're playing at that level, people are going to know who you are. You had two exits, you had a bar, so you were ingrained in the community, and then you had a startup, sold it, moved to Boston, and struggled to figure this out a little bit. What helped you? What advice would you give someone in that same situation trying to figure it out?

Callan Harrington 19:14
That's a great question. I don't know how many people are in that particular situation, but for me, it’s about understanding what I want. I would think to myself, "Okay, I'm here. How can I make the best out of this situation?" It's that competitive nature—always trying to do the best. I’d think, "I'm here. What now? How can I do better from this situation?" It’s always about thinking, "How can I make the best out of a given situation?" The second part is being really honest with yourself—like if you’re thinking, "I moved for a reason," you realize sometimes it’s not all about you. Sometimes it’s about your partner, letting them shine and be the star of the show, and you figure out things on your own. And for me, it was always an opportunity for learning. Being in that situation made me want to go out more, meet people, learn more things, and understand the culture in a new country—what people are expecting. It was easier for me because I was in Cambridge, and my wife went to MIT Sloan, so I was part of a community of great, smart people. You meet a lot of amazing people along the way. But still, a lot of the challenge was self-reflection, understanding why I’m here, and making the best out of that situation.

Callan Harrington 20:50
I think that's excellent. And I want to fast forward a little bit. Not surprised, your wife went to MIT; you went to a top business school as well—Berkeley. What led to that decision?

Callan Harrington 21:01
Yes, I think, you know, moving to a new country, the same situation as before. I tried to start another startup with a person I met, which went okay, but it was my first time starting something and failing. It was okay, but it didn’t go where we wanted. We tried to raise money but weren’t successful. It was another decision point in time—similar to when I decided to quit soccer. I had to ask, "What’s next? Do we want to stay in the US? Do we want to go back? How do I see my career moving forward? What do I want to do?" I knew I wanted to make the most of moving to the US. I liked the culture, and I thought I could learn and grow a lot more. So I thought, "What makes the most sense for me?" It wasn’t about going out and finding another job; that was more challenging. When I looked at different jobs, it felt like taking a few steps back—doing an entry-level job, especially coming from a different country where people didn’t know what I had done. Seeing my wife's experience and how great it was, I wanted to do something similar. So I applied to business schools. It’s not an easy process, but I spent time on it and applied to the top business schools. I got accepted to a few, which was surprising because I wasn’t expecting it. I got into a few good schools and decided I wanted to be where innovation happens—where everything happens from a technology perspective. So I decided to go to Berkeley. All the business schools I got into were really good, but I asked myself, "Where do I want to live? Where do I think I want to spend my career? Where do I think I’ll grow the most?" And that was Berkeley, California.

Callan Harrington 22:58
Gotcha. So you shifted, went into business school. How was that transition? You’d done a decent amount of business at this point, then pulled back and went into business school. What was that transition like?

Callan Harrington 23:12
You know, I went to business school with a goal. I was looking at the market for jobs before, and there were mostly junior entry-level roles. So I went to business school thinking, "Hey, I’ll get a formal American business education. I’ll interact with larger companies. I’ll put some brands on my resume, and it would be easier in the job market later." That was the initial thought. But personality-wise, it turned out differently. When I got into business school, the things that drew my attention were funding companies, entrepreneurship classes, raising money, and becoming a VC. All the classes I took and the projects I did were about building companies, helping companies, and learning how to fund them. I’d say 70% of my MBA was about learning early-stage company building and funding, which was an amazing experience and learning opportunity, but not what I expected going in.

Callan Harrington 24:10
Here’s a question, because this is a hot topic. Would you recommend someone go to business school or not? If yes, in what situations would you recommend it?

Callan Harrington 24:19
Yeah, it’s a big question. I agree, it’s a hot topic. For me, it was one of the best decisions of my life. Why? Because I learned so much, met so many amazing people, and did it in a place where I wanted to grow my career. Location had a lot to do with it as well. It brought together everything I wanted—it put me in a place where I learned a lot in the areas I really wanted to focus on, and that helped me the most. So, if you ask me questions about how to start a company, what’s important, how to do it, and how to raise money, I’ve gained so much information from people who have been there and done that. I met so many people along the way, and when I need advice or need to ask for something, those people are there. Especially being part of the network of the school, it’s amazing—when you reach out to people, they just answer, which might not happen otherwise. So, for me, those three things make it one of the best decisions. Whether it’s the best decision for everyone depends a lot on what you want for your career and how you think about it. But for me, it was the best decision.

Callan Harrington 25:34
I don't want to give generalized examples, but if you're a consultant who wants to go to a tech company, you probably don't have to do an MBA to make that transition. You can do it without that. But spending two years of earning potential plus paying $100,000 or $200,000 for the degree, and putting yourself $300,000 or $400,000 in debt, that’s very hard to justify if you’re looking at it from an analytical perspective.

Callan Harrington 26:00
Makes sense. So, while in business school, how did you get involved with Agentero?

Callan Harrington 26:08
I met Luis, the founder of Agentero. He was also at business school with me—same year, same start at Berkeley. We hit it off right from the beginning. In the first week, we met a few friends, and I met Luis. What I liked about him was that he was super sharp but also super fun. Whatever you asked him, he was always on top of things, even if he wasn’t listening. He was visibly sharp. But then, he’d go out and have fun. That’s how I met Luis and eventually why I joined Agentero. But in between, I also did an internship at Embroker—another insurtech company. I spent three or four months there between my first and second year, which was a great experience—learning about the US insurance market, getting a glimpse into that. That experience and the fact that Luis dropped out after the first semester because he raised his angel funding for Agentero brought us together. I wasn’t involved much in the funding, but I knew him, we were friends. I was at Embroker, and at the end of the summer, he was at a point where he needed someone to help with marketing. He was like, "We need more leads; I need someone to help with marketing." He knew I worked at Embroker, so we started working together part-time, helping him through a couple of months. And then, after that, I joined full-time during the second year of business school. I’ve been with him ever since—it’s been a great ride.

Callan Harrington 27:56
It sounds like you guys have grown like crazy. What have been some of the challenges you've had to overcome throughout that growth?

Callan Harrington 28:06
Wow, there are a lot. I joined as employee number four before we had anything other than a landing page and something an engineer started developing. Back then, the challenge was building this machine that starts bringing leads, figuring out what the product is, and everything else. We had a very particular niche, which is insurance agents in the US—a very small industry. How do you bring these people in, get them to notice you, and actually be interested in what you’re doing? That was the first challenge—figuring out how to do that in a small niche. I hadn’t done it at full scale in the US before, but I had done a lot of similar things back in Israel—similar networks, social networks, types of marketing motions, and so on. So bringing a lot of those concepts I had already worked on helped a lot. That was the main challenge. But now, as we grow, the challenges have multiplied. The first was just setting it up, executing, and personally going in, putting all those things in motion, and building from scratch—evaluating systems, what we need to do, and how it scales. Then, the challenge becomes building a great team that adds value and can do things better than I do. The number one challenge is keeping up with hiring the best people for the roles, keeping them happy and engaged, and creating a culture in the company where people are happy to come in.

Callan Harrington 29:34
What advice would you give people on how to do that? How have you done that successfully?

Callan Harrington 29:41
So, on hiring and building a great team, I think it starts with the process. For me, hiring starts with a process—being able to hire based on objective criteria and not just bringing in whomever one person thinks is best because they liked something about them. We had to build our recruiting process from scratch. When you start from scratch, you have to build it—there’s no one to come in and say, "What’s the best way to do it?" So we made sure each role had an actual test that candidates would do, multiple interviews to get different perspectives, and a way to avoid bias. A lot of work went into defining the process—how to hire the right people and how to do it. And then, of course, a lot of work went into filling the pipeline. For me, once you have the process, filling the pipeline becomes the easier part—it’s more of a marketing and sales challenge. But setting up the process and making sure you hire the right person for the role is harder than just filling the pipeline with candidates.

Callan Harrington 30:45
If I’m playing that back to you, it’s about setting up a process for recruiting, evaluation, and onboarding, and starting that early in the company. A lot of people don’t realize you can do that. The process will be iterated on a thousand times, especially if you’re growing rapidly. It’s a totally different company every six months.

Callan Harrington 31:05
I agree with some of that. The process of evaluating a person might change and iterate a little, but the general concepts—multiple interviews without bias, having objective criteria, some sort of test for each role—those don’t change. Who’s interviewing might change, and the questions might change, but those concepts are consistent. Talking to a lot of founders and companies I’ve met, they often don’t pay attention to that. They’ll talk to someone, think they’re great, and hire them quickly—sometimes ignoring red flags and not removing bias. If the CEO says, "Hey, interview this person; I think they’re good," that person will likely be hired. You want to build a process that removes bias so you actually hire the right person for the role.

Callan Harrington 31:55
That’s a totally fair call-out. I think that’s excellent advice—setting up a system. A lot of times, I find a scorecard is great for this, especially if you have to hire a lot of people. Whether you’re hiring a lot of people or just a few, the scorecard helps because it can be hard when you get down to the final few candidates. The hardest is when you have so many good people—that’s a tricky one. It’s a great problem to have, but it is tricky to decide who to pick. So I think that’s excellent advice.

Callan Harrington 32:27
One question I want to leave with is, what would you tell your younger self? I purposely left that vague, so it’s up to you what age that person is. But if you could have a conversation with your younger self, what would you tell them?

Callan Harrington 32:42
Yeah, great question. I would tell them, "Everything will be okay. Take it easy; everything will be okay." I grew up in a small city without a lot of safety nets, so I had to grind and work really hard, being very competitive all the time to be the best. I’d tell my younger self to relax a little—it’ll be fine. Don’t worry about that. It’s okay that you’re trying and being competitive, but it’s also okay if you’re not working 24/7. I think that would be the one piece of advice I’d give my younger self. It applies to other people too. Yes, you want to be the best, you want to do more, but you’ll be fine. Don’t worry about that. I try to give the same advice to my two younger daughters. They’re super young—the older one is four and a half—but she tries to make everything perfect. If something doesn’t work, she gets super upset. I tell her, "It’s going to be fine; don’t worry." And you know, I say that to my child, but I should have given the same advice to myself when I was younger.

Callan Harrington 33:40
I love that. I think it’s dead on, especially if you’re really driven, right? It feels like these setbacks could almost be the end of the world, but the reality is they’re not. You’re not even going to think about it in five or six years—probably not even in five or six days. But I think that’s excellent.

Callan Harrington 34:00
Ido, thank you for coming on the show. This was so much fun, and I appreciate you joining me today.

Callan Harrington 34:06
Thanks, Callan. It was a lot of fun. I hope this experience helps someone along the way.

Callan Harrington 34:11
I love it. Yeah, I totally understand. Thank you.

Callan Harrington 34:15
Well, thanks, man. I appreciate that.