InsuranceAgents: A Shocking Thing Happened After It Hit $12 Million

This is the story of a first-time entrepreneur who seemingly-overnight reached $12 million in sales and the shocking thing that happened to him afterwards.

Seth Kravitz co-founded InsuranceAgents, a site that lets consumers compare insurance quotes. During a 12-month period, he grew revenue from $700,000 to $12 million and generated 150,000 leads.

Today, Seth is running Technori, a digital magazine that celebrates entrepreneurship in Chicago.

Seth Kravitz

Seth Kravitz


Seth Kravitz is the cofounder of Technori, a digital magazine that celebrates entrepreneurship in Chicago.



Full Interview Transcript

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All right, let’s get started.

Hey there, freedom fighters, my name is Andrew Warner, I’m the founder of, home of the ambitious upstart, the place where proven founders come to tell you their stories so that you can learn from them, go out there and build your own success story and hopefully once you do, you’ll be as willing to share your story as today’s guest and the hundreds of other guests have on Mixergy.

You know I like to focus these interviews and so here’s this focus. The focus for this interview is, I’m going to tell you a story of a first time entrepreneur who seemingly overnight reached 12 million dollars in sales and the shocking thing that happened to him afterwards. Seth Kravitz co-founded Insurance Agents, a site that lets consumers compare insurance quotes. During a 12 month period he grew revenue from $700,000 to $12 million and generated a 150,000 leads. Today Seth is running Technori, a digital magazine that celebrates entrepreneurship in Chicago. Seth, welcome, and thanks for doing this interview.

Seth: Thanks for having me. It’s fun to be here. I’ve been following this site for a while, so it’s fun to actually be on it.

Andrew: Thank you. Do you remember what it was like when you look down one day and say $12 million is coming into this business that I just founded that was just a vision in my head at one point.

Seth: Yeah, it was kind of crazy. You can’t predict that kind of growth. You’re never really ready for it and to be honest we probably grew way too quickly and it was probably growth for the sake of growth which is the worst kind of growth. It wasn’t really planned out very well and we certainly paid the price the following year after all that explosive growth. Things fell apart and then we were able to luckily repair everything and get it back on track but for a two year period there it was hell.

Andrew: You know what? I wrote down a note here to come back later in the interview and were going to go in chronological order to see how you built this up, but at the right time I want to find out how a company can grow too quickly. I thought growth was all good and I want to understand through your story how it can be too good or how it can overpower a business. I do want to take in chronological order but one of the things out of order that I want to talk about; did you marry the guy you co-founded the business with?

Seth: No, no. We started out of his parent’s basement. We started back in 2004 out of his parent’s basement and just a classic folding table. We had a mutual friend who said hey I’m a web designer helper and he was an insurance agent and [?] so we just got together.

Andrew: Oh I thought that. Yes.

Seth: No.

Andrew: Ok. I thought that there was some marriage there. Maybe my notes are little bit off. I’m reading a lot of my notes from the Ink Magazine article?

Seth: Yeah, so, well, business partner obviously and not relationship partner.

Andrew: Oh, boy did I get that wrong. You know, I’m glad that I asked you upfront. There was some, do you mind if throughout the interview we talk about, is there some issue with the relationship? Where at your toughest time you broke up? Is that something you feel comfortable talking about?

Seth: During the course of right after we had rapidly grown and then sort of peaked really quickly and fell into some IT problems, during that same exact period of time I actually got divorced as well.

Andrew: OK.

Seth: It was, yeah, it all kind of happened at once.

Andrew: All right. Well tell you what, I’m going to put it off for now. If you feel comfortable at all talking anything personal I’d love to talk to you about it. The reason that I want to do that is because I feel that the only way that we can really understand motivations and what happens in business is to get those personal stories. I remember when I talked to Alexis Ohanian of Reddit and he told us that he sold his company, and clearly Alexis did not sell the business at the height and I was trying to find out why. It turns out that his mother was going through some issues, some health issues, and that’s why he needed to back away from the business. In retrospect was it a bad decision? I don’t think so at all. But it does help us understand the overall decision making process when we understand what goes on behind the scenes.

Having said that, I haven’t earned your trust yet. There’s no reason why you should tell me any of this stuff. Frankly even if I did earn your trust and you don’t feel that it’s the right place to talk about it I’ll understand completely. I want as much as you feel comfortable sharing here. As much as I can learn from you I want to learn from you.

Seth: I assume these are all kind of chopped together. It’s not like this entire conversation is in order in the video or?

Andrew: We go through it in order. In fact, right now what we’ll do is we’ll go back in time to where the idea originally came from and then we’ll just continue in chronological order and let the story unfold as it will.

Seth: Well, I’m talking about the actual video when they go live on the site.

Andrew: Oh, kind of chronological order, yeah.

Seth: Is it edited or is it just literally everything we’re talking about right now?

Andrew: Everything we’re talking about right now.

Seth: Fantastic. All right.

Andrew: This is podcasting. I don’t have a budget for proper editing. And also it creates a more real environment. Is that…?

Seth: No, that’s fine. Yeah, sure. I mean, had I known that I guess I would have just been like yes.

Andrew: Given me short answers? Well, you didn’t say anything that…

Seth: No, it’s not that. I would just talk more like it was actually in a live interview and less, I was assuming that they were kind of edited together at the end.

Andrew: Ah, no. Anything that you said that you feel uncomfortable about? All right.

Let’s go back and see. The original idea came to you while you were at Ohio State, the idea that led to this business. Is that right?

Seth: Yeah, we were at Ohio State University. He was actually at a different university. We just, I had nothing better to do. I was not a very good student. Kind of had like authority issues. I was never going to make it through college. I barely made it through high school. I just kind of realized that, it just seemed like a better opportunity than trying to get a job or trying to go to school. It seemed more fun to go create something. It was a pretty easy sell when he was just like yeah, let’s go do this insurance marketing company.

Obviously I wasn’t interested in insurance. It’s really hard to be interested in insurance. It’s just boring it’s unbelievable. It just, I don’t know, the challenge of taking something and taking a big pile of nothing and trying to create something out of it.

Andrew: What do you mean you were rebellious? What was it about school that didn’t draw you in and make you feel like this was a place for you to excel?

Seth: I never traditionally liked school. I barely graduated high school. I had a 1.92 GPA. It didn’t, I spent all my time in class filling notebooks with sketches of buildings and things like this. I thought I wanted to be an architect until I realized that being an architect actually really sucks. You spend like 30 years of your life locked away in a cubicle drafting. It’s not what they picture like in The Fountainhead or whatever. It is not that. It’s like oh, there’s an empty lot and I’m going to put a huge building there. That’s not how it works. You spend most of your life literally locked away in a cubicle drafting and that’s pretty much it.

Andrew: OK.

Seth: I thought I was going to be an architect and then as soon as I realized that it just kind of sucked that pretty much sucked the last little bit of interest in school away from me.

Andrew: Right.

Seth: That was it. I was done. There was no way I was going to finish. If I hadn’t dropped out I would have failed out. I had no chance.

Andrew: Was there any passion at that point for entrepreneurship? Did you read about famous entrepreneurs and say I’d like to be like them? Did you dream that maybe you didn’t want to have a job but if you could create your own company you’d have a life that you wanted? Anything like that at that point?

Seth: Nope, no. It was just more like I was unemployable. As I said I have authority issues so I would, I mean I got fired from the fast food industry. If you can’t cut it there you really can’t cut it anywhere. I don’t know, I’m just not very good at seeing something that’s inefficient and not speaking my mind and saying this is not being done correctly. In the corporate world, especially if you’re just like a low peon working in fast food or whatever, they don’t like you commenting on their systems and the way they do things. It was never going to work.

Andrew: OK. All right, that wasn’t going to work and then an opportunity presented itself. It had something to do with insurance and you said that’s not the part that drew you in. What was the part that made you say hey, this could be a life for me?

Seth: Well, I’ve never been drawn to ideas really in general. It’s more about the opportunity. I like taking, as I said, a big pile of nothing and creating a big pile of something out of it. Right now I’m launching a coffee company. I didn’t start drinking coffee until three months ago. I’m launching with two other people who are coffee fanatics so it’s not like we don’t have coffee knowledge. It’s just not me. For me it’s never been about ideas.

Insurance was just an ends to a means. I wanted to create something and here was somebody that wanted to create something too. In Columbus, Ohio there’s not really much of a start up community. We were very much alone. There wasn’t a whole lot of mentorship. There wasn’t a whole lot of, actually that really kind of sucked. We somehow made it work but it really wasn’t an ideal environment to launch something.

Andrew: I see. The coffee shop, by the way, apparently is Bow and Truss. That’s what you guys are calling it?

Seth: Yeah, it’s actually a coffee company. It’s importing, roasting, wholesaling, and opening a chain of shops here in the spring.

Andrew: Got it. OK. I’ve got a ton of research on you. Whoever, you know what, you have such an interesting story that whoever did this research for me, and I don’t know if it’s Ari or Andrea, added a lot to it. Then I, as I was clicking around, kept coming up with all kinds of notes on what you were doing. To go from insurance to then helping to grow a start up community now in Chicago and then to coffee makes for a very interesting life.

Seth: Yeah, since I’m not [attached to] ideas that means I’m always going to be jumping around forever.

Andrew: All right, I want to understand that too. The co-founder was Lev, right? OK. Lev presented you with this idea to do an insurance based online business. He had a little bit of experience in insurance. What was it?

Seth: He had already launched an insurance agency. At 18 he started an insurance agency and became one of the fastest growing All State agencies in the country. This is an 18, 19 year old kid. He’s one of the best sales people I’ve ever met in my entire life. He can sell anything to anyone anytime. He really is one of the best.

Andrew: Do you remember, what I’ve noticed about good sales people is that there’s certain things that they repeat. That if you watch carefully maybe you can take good notes and not be them but you can predict what they’re going to do. Did you notice a few things about Lev that made him a good sales person that you can share with the audience and make them better sales people?

Seth: He always stayed really comfortable. I’ve never really seen him lose his temper or skip a beat. No matter even if you could tell the sale wasn’t going the way that he wanted he just, he always did a phenomenal job of just staying on point and just keeping his calm. What’s great about that is when you get angry, you get excited and everything, your brain literally starts to kind of shut down. It becomes much more difficult to do critical thinking, to do problem solving. I think one of the biggest things he always did was no matter what was happening he was always super calm and was always thinking five steps ahead in the conversation of where this is probably going to go and trying to lead them.

I think it’s some of the things that an uber kind of sales guy can do. It’s one of those things that I always struggled with. I was never on the sales side. I was more on the web side and also on the marketing side. The actual sales part was always tough for me. I do not like asking for the sale. I am a terrible closer. I can get people super excited all the way up until that last moment when you’ve got to close and then I fall to pieces.

Andrew: Have you ever met those people that are so good at closing that they just keep putting those offers out there. They just keep asking hey, would you mind tweeting this out? Hey, why don’t you just run this on your home page. You accept one or two of their requests because that’s a thing that we’re naturally trained to do, to accommodate I guess. You go how did I even get to do this? Where does he have the nerve? You have?

Seth: Oh yeah, it happens to me all the time. People doing that to me and I always fall for those things. If you switch the roles around I am terrible at asking for the sale. I’m just not good at it. Which is good. I realized that was a weakness of mine so it was great to partner up with somebody who had that.

Andrew: That had that, yeah.

Seth: It really balanced us out, because if both had been like me, or both been like him, you know, it would have been very difficult to build the company we did.

Andrew: OK. So you were going to do the web and online marketing, he was going to be the guy who was going to close sales. What was your experience in web developing and marketing before this?

Seth: I mean, honestly, at that point, it was still limited to just building small websites. I built like a weird niche, building auto repair websites.

Andrew: Which, a niche auto repair website?

Seth: No, I mean, I built out a niche for myself, for my web design. I built one auto repair website, and this was back in the days where you could get away with saying at the bottom, like, this website was designed by, you know, it was early on, people would just let you do that. So the next thing you know, another auto repair site says, “Hey, I like that site, can you build one?” And the next thing you know, I literally have eleven clients and they’re almost all auto-repair shops, all around the country who just kept seeing sites I was building, and it’s a weird little niche I carved out, but it helped it give me beer money.

Andrew: I see. Alright, so he’s the guy who’s the born salesman with a lot of insurance experience and success. You’re the guy who’s building websites, who understands the internet. You guys are going to get together and build something. What’s the first thing that you guys built? What’s the first version look like?

Seth: It was awful. It was really awful, but we weren’t afraid to get it out there, so we got out a terrible site and just started driving a lot of traffic to it. I mean, this is back in the day when PPC a lot easier to do. There was still a lot of things you could do to game the system that you just can’t do today, so a lot of the things we did launch, we just wouldn’t be able to repeat them today, but we took advantage of the fact that back in the day, there were just all sorts of really cheap traffic driving sources out there, and we just drove a lot of traffic to this really crappy site, and try to sell people insurance online, and we at that point were just the middleman, so we passed it on to somebody who else who’d pay us a commission.

That was just to start generating cash flow from the beginning, but then eventually we switched to being the actual lead generator, where we sign up the agent directly, we sell the information directly to the agent. But at first, we were just the middleman, because it takes a while to build up enough agents coast to coast to be able to actually sell directly.

Andrew: OK. You said awful, crappy, you said a few things about the website. I wrote a note down to ask you what was it about it, in retrospect, that was so crappy and awful?

Seth: Everything. It looked awful. It’s weird, in the XXX space, honestly, in a lot of internet marketing, you’d be shocked at sometimes how much better a really crappy looking page can perform than a really amazing looking page. You can really over design a page, where you focus way too much on making it look really beautiful and not actually converting. In our field, it’s all about conversions, so it’s converting people, and we found the less we put on the page, the less intense it was, the more people actually converted.

So honestly, by having a really crappy site that was really basic at the beginning, it actually kind of set us on the right track, that simple XXX space, whether it’s insurance or mortgages, anything. There’s only like 200 verticals of Legion. It really doesn’t matter which one you’re in. Simpler tends to be a lot better than super over designed, at least in our field. You could make it completely different, and if you’re looking for a web designer, I wouldn’t want to go to a site that looked like ours, cause I would never trust them, or a marketing firm or whatever, I would just expect a little more, but in our space, simple just works, just really, really basic, simple. There are people buying me, so.

Andrew: I see. So you launched something that was very basic, and it turns out that that worked better than over designing it. You also said then that you started getting traffic very quickly, and you were gaming PPC, paid-per-click advertising. What was possible back then? What did you guys specifically do?

Seth: Well, it’s possible to get cheap clicks back then. If you’re exceptional at what you do, you can still do that, but not like you could back in the day.

Andrew: We’re talking about 2002 is when you guys partnered up, 2004 is when you started, right? So around there.

Seth: Back in ’04, not only were the costs per click dramatically cheaper, but you could do things like we’d build out six different sites, and stack up for a certain keyword, the number one, number two, number three, number four, number five spot. You could do quality score, and things like that this that weren’t really present yet, so it didn’t really matter how crappy your page was. You could bid on keywords all across the entire spectrum, and quality score didn’t matter, so at that point, it was dramatically easier. That’s all I can say. It was so much cheaper back then, and it literally, as I said, trying to do what we did then now, would literally be almost impossible. You couldn’t start the way we started then.

Andrew: Today, if you buy how to tie a tie as the key phrase in Google, and that linked over to a webpage that just had a form asking you about your insurance needs and nothing else, if most people bounced out of that, today Google would just shut it down. You wouldn’t get much traffic. Back then, that would give you access to a mound of cheap bases.

Seth: Yeah, you could do things like that back in the day. You can’t do now.

Andrew: OK, and you were buying just from Google, or also arbitrarily?

Seth: All across the board. I mean, Google was like the most advanced at that point, so when you’re talking about Yahoo system, which was overture at the time, well, I guess it was MSN at that point, and then it became Live, and then it became Bing, but back in the day, their systems were just way too easy.

Andrew: And you know in certain things, being an early adopter is a problem. Like, if you’re the first guy to install the latest Mac operating system, there are going to be certain programs that won’t work right, certain programs that won’t save right, and the same is true for a lot of technology, but when it comes to buying ads, when you’re one of the first people in and the first people to figure it out, there’s a huge advantage, and that’s true whether it’s pay per click advertising in search engines or after that, for Facebook, and then eventually there were people who were doing, and I’m sure today still doing similar things for iOS. It helps a lot, doesn’t it?

Seth: Yeah. What’s nice about being on the ground floor and watching it evolve is I just have a much deeper understanding now than if I was trying to jump in now. It paid to kind of go through the early growing pains of, cause they were changing the system so frequently back then, and you were just constantly trying to keep up with everything. Now, everything is much more like every six months, and it’s very planned out, the way they do their things, and back then, it was much more just like things were literally changing. Every few weeks, there would be some dramatic change to MSN or whatever, and we’d have to kind of change the way we were doing things, and it was kind frustrating, but at the same time, though, I mean, the Internet’s becoming less of the wild wild west.

Everything is becoming much more standardized, everything is becoming much more just kind of planned out. Everything is much more robust and everything from security, everything you can think of is becoming dramatically more robust in general, so that it’s starting to feel more and more like the real world, as far as the difficulties of entering and things are more expensive and you know, the opportunities to game the system and everything are becoming fewer and farther between. It’s not as crazy as it was back in the day, so it’s slow, but it’s fun.

Andrew: Do you remember those days? I remember actually buying ads on the cheap from Overture, and sending them to forms where people would join my mailing list and ending up with, like, two cent clicks that converted at ten cents per email address per person who’s on my mailing list who I get to send them trivia or jokes or whatever it was we were doing at the time, but at the same time, I was earning money on advertising from them for days, for months, for maybe even years.

We were excited. We felt like we were kings of the world.

Seth: Back in the day, you could do all sorts of arbitrage things. I did some arbitrage. It’s fun.

Andrew: Arbitrage, meaning you were buying clicks on Google on the cheap, and then sending them to someone else for what?

Seth: Everything you could imagine, so all sorts of silly programs, running traffic from MSN, Yahoo, to Google AdSense pages.

Andrew: I see, buying ads on Yahoo to pages that have ads for Google, which pays you more than Yahoo, that kind of arbitrage.

Seth: This is back before, like, you know, they had Google quality score, but other ones have similar systems now. You can’t get away with driving, because you could drive people, in most expensive terms, you know, they still are, and insurance, and mortgage and loan and legal terms are still way up there. So you drive people literally searching for something like a music term, which are incredibly high traffic. Pick one, like Green Day or whatever, you could run an ad for Green Day, saying, you know, free Green Day t-shirts or whatever, it doesn’t matter, and drive it to a page that talked about mesothelioma with AdSense.

And these are the things you could do back in the day that you can’t really.

Andrew: But let me tell you a little bit about myself, and I’m hoping that this will show. I want to create a safe space for us to be open about who we are. And I don’t want to pry beyond anything that you’re comfortable with, so this isn’t a tactic to do that, it’s just, well here. I remember when we did that. Suddenly revenue was coming in, I mean, hundreds of thousands of dollars. I still have copies of those checks. They’re millions of dollars in ads.

I felt at that point like this vision that I had of myself was vindicated. That it was absolutely true that I was meant for some kind of greatness. Now, up until that point, I was the kid who no girl would date in school, because I was freaking awkward. I remember even in retrospect now, I was on a date with someone and I didn’t even know it and I was too busy in my head thinking why won’t girls date me.

And in that moment, I thought everything that I thought I was capable is absolutely true. And also, that gave me power to ask for more money from advertisers, gave me power to have someone say to me, we’ll give you three million. I said three million? I think this is worth five million dollars. Where’s the guy have the guts to do that? So that was good stuff that came with it.

At the same time, I thought also that I was invincible because of it, that there’s no way that I’m ever going to go down because I may not have it socially, but when it comes to business, I am the man and I proved it in my head before it happened and in reality when it did happen. And that was why I succeeded and why I fell. So how did you feel when that happened? Obviously, I had this mind screw that happened to me.

Seth: I never felt right about Arbitrage. It always felt like this can’t be real.

Andrew: You just knew this was going to go away.

Seth: Well, you could tell it was going to go away.

Andrew: Because it’s Arbitrage and Arbitrage always goes away. Inefficiencies in markets are always done away with, at least by people like you if not by laws.

Seth: It just, I don’t know. It just never felt right. You could tell it was going to go away and that was just one of the million things you could do back in the day involving affiliate programs but the more things started to grow with, we definitely hit a point where my partner and I were just definitely thinking we were a little invincible and that we couldn’t screw up. And then it just completely blew up.

It was, wow. That was an unbelievable wakeup call learning lesson. Whatever you want to call it. In hindsight, it’s just so obvious but in the moment, you feel like things are going really well and decisions we were making, the revenue kept going up every time we made a choice. So we just were like obviously we know what we’re doing and then we discovered we didn’t have the slightest clue what we were doing and it really sucked when that happened.

Andrew: Can you describe the business when you launched? You said that you guys were middlemen at first? What was it? You were sending people to a page that did what and then what happened with whatever it was that they did?

Seth: We’d drive them to forms and that information would be sold off by other lead generation companies.

Andrew: OK.

Seth: They pay us commission per lead.

Andrew: And so it would be a form that said do you want an insurance quote and on that form it would be what’s your name, what car do you drive and so on and then you’d sell that. Who would you sell it to?

Seth: There were a bunch of other competitors. A lot of people who have been bought up in the last few years but some of our major competitors are like Net Quote and Insure Me. There’s some big players that are in the hundreds of millions revenue that just do, or even some of the more obvious ones you might think of like Esurance.

Andrew: I see.

Seth: They all pay for traffic.

Andrew: And they end up taking those leads and selling it to individual agents or to local shops or how does that work?

Seth: Mostly to individual agents. Sometimes they’d sell it directly to carriers, like Esurance is a carrier. So they would buy leads for themselves that they want to sell those. But for the most part it’s just selling to the 450,000 total licensed insurance agents in the country, about half of which are sort of captive and/or in house or they just have a license and there’s another half or so that are independent ones that sell for multiple companies.

Andrew: I see. It sounds very much like Glen Gary, Glen Ross when they had those leads on paper and they’re all fighting for them because if they get the hot leads then they could close the sales which will make them winners.

Seth: Yeah, we used to show that video to our sales people. It’s a popular movie around the sales office.

Andrew: How did you get sales people? At this point, everything seems very cut and dried. You get traffic to a webpage. People fill out a form. You take that data and you sell it off to these companies that are out there buying these kinds of leads. What’s the next level? How do you grow from there?

Seth: We hired a lot of commission only sales people at first. It allowed us to grow out our sales team without having to pay them, obviously unless they closed. It definitely wasn’t ideal. I would never encourage anyone to build out a commission only sales structure. It’s just, the people that it attracted, they were just, sometimes it was a nightmare. The difference between that versus paying a really awesome professional sales person a salary and all that, you get a completely different level of talent. But it was just kind of like something we had to do at the beginning because we couldn’t afford a salary, like staff salary. So we went commission-only and paid people when they closed.

Andrew: So you originally were getting the leads and selling them off to someone else who would close those leads, get people who are interested in insurance quotes to sign up for insurance. You then start hiring people on commission and saying, “Look, you work the phones. You get these people who told us they’re interested in insurance to buy insurance. We’ll get a commission, we’ll split that commission with you.” No?

Seth: The sales team were hired to go out and find insurance agents who would then buy the leads.

Andrew: Oh, I see. The person who would eventually service the… I see. So they started making phone calls. Do you remember what they were doing? What were some of the most egregious things these un-commissioned salespeople did?

Seth It wasn’t really anything they did. They just tend to be unreliable. They were very flaky, they’d work for two weeks and then disappear. It’s really hard to build a solid company when your people are leaving you constantly. Really high turnover. Lots of training, constantly training because we were just losing people. It was not ideal. It worked in hindsight, I guess you could say it worked, but I would never build a sales team like that again if I had a choice. But we were creating [??] in the marketplace so we had to get consumers and the agent/buyers.

Andrew: How much were you saving by going directly to the agent with your own salespeople? What kind of money were you saving?

Seth: Every time I look at the consumers? What are they…

Andrew: No. I mean there are these companies built to buy leads from you and they give you a certain amount of money and you said “We can bring in more money if we bring in our own salespeople.” I’m just wondering for the trouble it was worth how much extra money was in there?

Seth: It was quite a bit. There’s a ceiling when you’re basically an affiliate in the middle like that. There’s a ceiling and they’ll say, “The most we can pay you is $10 a lead for an auto-lead” or whatever, and that’s pretty much all you’re going to get from them. On their side, they might be taking that same lead and selling it three to four times. Multiple agents are making a lot more than $10 and we never got any of that, we just got a flat number and they were very reluctant to do revenue shares. We just realized it wasn’t going to work. We’re going to be stuck at a certain level of revenue forever if we stay an affiliate. The only way we’ll be able to get to scale.

You can’t just… the way it worked in the day was it really hard to get traffic from just Ohio and get Ohio agents. We had to start signing up agents coast-to-coast, all 50 states. So to do that, we had to get a lot of sales people quickly and get them on the phone cold-calling all day. Emailing and cold-calling. It all worked, it was just literally by sheer effort it worked.

Andrew: You said they were selling a lead multiple times to multiple agents. How does that work? How can you tell…?

Seth: It’s standard industry… shared leads. Shared leads are sold anywhere from 3-5 emits.

Andrew: So you better really win. You get those hot leads; you better make the phone call and close them as quickly as possible because someone else will be on the phone to them.

Seth: One of our jobs at was to make sure our agents were constantly using the best technology, the best scripts. Giving them whitepapers, videos, training sessions, webinars. When you’re competing against 3-4 other agents, you need to be first on that phone. You need to be closing following up with emails and phone calls later on because you’re competing against potentially two or three other agents are doing the exact same thing.

Andrew: Let’s give it a moment for the audio and video to catch up. They’re losing the connection there, you said.

Seth: I can’t remember what that exact number is… it was at least 70 or 80% more likely to close the lead if you were the first person to make contact.

Andrew: So you built this up to $700,000 in revenue, which is huge, and then, boom, you get to $12 million. How do you get such a big jump over 12 months?

Seth: There’s $750,000 in 2008 and then just shy of $12 million in 2009.

Andrew: So what happened in 2009 that helped you get such a big jump?

Seth: Or was that 2008? 2007 or 2008. 2007, sorry. 2008 would be $12 million, 2007 would be 73,000 [SP]. That is the difference between being an affiliate and actually being the lead generator. So if you want a taste of what it’s like to be a middleman vs. being an actual provider, that gives you an idea of what we were leaving on the table. Also, we just signed up so many agents. We were very aggressive and honestly cold-calling and emailing and showing up at conferences and passing out cards like crazy. It’s just bootstraps. We had nothing to rely on other than our sales, so when you’re like that, you survive on selling. You only pay your rent that month if you go out and sell like crazy. We didn’t have a choice. We had to sign up agents. We had to sell those leads. We couldn’t focus on anything else other than that.

Andrew: Can you give us a sense of where you started that year, how many agents were buying from you, and where you ended, just to give us a sense of how many people you were closing?

Seth: I think in 2008, we were signing up around 400 agents a month. That number continued to increase until I exited back in October, we were signing up about 600 agents a month. I think at the time we had 8,000 insurance agents coast to coast that buy leads from us.

Andrew: And then you said something happened and it blew up and gave you an unbelievable wake-up call, as I have written down. What happened?

Seth: We were so focused on sales and building out, kind of our marketing and sales juncture, that we didn’t really focus that heavily on our IT infrastructure. It’s a giant piece of software that we built that sells a lead. It’s in real-time so it’s doing everything from literally the marketing landing page that’s powered by the system to processing the lead, setting it up with the right people, debiting their accounts, processing credit cards, sending the actual lead in real-time through email and text message and phone call, whatever, so the agents keeping track of this stuff, like analytics and all that, it’s one back end that powers all of that. It was really just kind of thrown together from the beginning and we patched it as we went, kind of crossed our fingers.

Then we decided in 2009, in July we were going to launch this brand-new platform that would be much faster and it would allow us to scale dramatically larger because it could handle a much larger volume of transactions. This is all theory. This is not what happened. That’s detailed in Inc Magazine story, you probably found out there. What happened is that we go to launch in July thinking the system’s been tested, all the developers that were working on it were telling us it’s fully tested, everything works, we’ll turn it live and there’ll be some bugs that we’ll fix, but it shouldn’t be a big deal. We turn it live and literally nothing works. Like nothing. It was obvious that it wasn’t tested and that they didn’t really know what they were talking about when they told us everything was perfect.

Over the next week, we just kept trying to patch it and fix it to get this new system to be stable. What happened is for the first week that we switched, from July 1st to July 9th, we didn’t exist as a company. I don’t think we processed $1 in transactions in that entire week. Everything was just completely messed up. Agents would log into their accounts and it’d say the balance was like $200, and then they’d log in a day later and it would say the balance was negative $1,000. Everything was just completely messed up. Agents were calling in like crazy, the phones are blowing up, the emails are just pouring in from our agents saying, “What is going on?”

I guess the obvious question we always get is why we didn’t just switch back to the old system immediately. Well, a lot of reasons, actually. One was we just kind of thought, “OK, we can patch the existing one. We don’t need to switch back.” What happens is, about a weekend ago, I was like, “Oh my God, we need to switch back to the old system. We have to get back on it.” What happened was, everything was built to go one direction in this transition. We had absolutely no plan or strategy on how to move back because we didn’t plan it.

Andrew: Ah, right.

Seth: On how to move back. Then we actually ended up losing a few developers during this process. People that would actually have the knowledge of how to move it back.

Andrew: OK.

Seth: What happened is we ended up with a situation where we couldn’t move it back. We were stuck on the new platform which was a very desperate situation to be in. Because we realized wow, we have no choice but to fix all the bugs with this new system that we put in place July 1st. That took probably about 40 days to fix everything. During the entire month of July and August I think our revenue was maybe, I don’t even know. It dropped. It was embarrassing. It dropped to a fraction. Personally Lev and I, since we’re a bootstrap company, we burned through over $1 million in cash.

Andrew: Wow.

Seth: To keep the company afloat a friend of mine out of New York city gave us a very temporary, like 90 day, loan to float us basically. We somehow managed to pay that back within 90 days which was incredible. It took months for us to calm down to the point where A, you didn’t want to like somebody. It took a while to calm down and finally look back and say OK, what did we do wrong? It was probably November, December before things were stable enough that we could actually take a pause, look around at everything leading up to that decision to go live July 1st. Stuff becomes so obvious that we made just painful mistake after mistake.

Then we spent literally the entire year of 2010 putting in new policies, building out an entire new development team. Changing everything. Changing our sales policies, marketing, everything. We decided to go back, we can’t just fix our development team. There are things that we’re doing wrong, the way we’re managing this company. We have to literally rebuild the whole company from scratch. In 2010 we went back to the drawing board and just completely rebuilt the company. Brought in a really amazing CFO that implemented a lot of policies that honestly made us into a much more, we stopped behaving like a couple of kids operating out of, like turned us into a real company. Because we were behaving still like a couple of kids operating out of basement and this is what happens when you do that. We changed everything to become stable, reliable.

Andrew: To people who hear $12 million coming in in revenue they can’t imagine how you’d be short money even if you did lose $1 million. How do you get to a place where you need a 90 day loan?

Seth: Well, when you’re paying people, so we’re paying all of our sales people a lot. On every account they close we’re paying them quite a bit. As quickly as the money’s coming in it’s going out. Also, most of our partners who were paying us, everything from the agents to some large partnerships we have, they’re paying us on like a net 60, net 90. We’re paying out our sales people out front for sales that we weren’t collecting on, revenue that we weren’t potentially going to realize for up to 90 days in the future.

Andrew: I see.

Seth: When you have an immediate thing where we have agents canceling like crazy and demanding refunds and we have to refund them out of our bank account. We hit a cash pinch there in July and August where all this money was going out in refunds. We weren’t going to ruin our reputation so if an agent asked for a refund, because if you’re logging into your account and you’re seeing balance $200 and the next day it’s (inaudible), whatever. You don’t trust that company at that point, obviously. You’re like give me my money. I’m done. We refunded everybody we could.

We tried to keep everybody we could happy on the basis that we could probably get them back in the future as long as we don’t do anything wrong now. We did, we got a lot of those agents to return to us. To do that, though, it was incredibly expensive. Literally we just, there were just millions going out and nothing coming in. Paychecks, not paychecks but like partner payments (inaudible) two months out even though we’re paying out that stuff now.

Andrew: What do you feel comfortable saying about how it affected you personally?

Seth: Oh, I mean 2009 was a bad year. It was a bad year. I’m trying to think of exact dates here. I can’t remember the exact dates but basically at that point, 2007, 2008, and 2009 (inaudible). And 2009 got the worst at the same time the company was collapsing. On the business front, everything was completely falling apart. On a personal note, my entire life was falling apart. And then financially, if you want to call that a third category, everything was completely falling apart. It’s an incredibly bizarre scenario to enter January 1st, 2009, to be financially stable, married, and a company that’s growing really quickly, and you feel like you’re a rock star, to literally finishing out 2009 broke. The company’s still going, people are still getting paid, but not anywhere near like what we did. Tech company is just completely shell-shocked, nobody can believe what happened during the course of that year, but we survived. It’s like a feel-good awful kind of moment. And also, single for the first time in years.

Andrew: How long were you married?

Seth: Two and a half years. We were together for about six.

Andrew: Wow. How did one thing affect the other? How was the relationship affected by work?

Seth: Everything was. I lost all stability at that point. From what I can remember from employees and stuff, comments, I became very standoffish in the office. I just went to my space.

Andrew: I did that.

Seth: Kind of “leave me alone” and didn’t want to talk to anybody. I’d come in with a hoodie on and headphones, “Just let me do my work.” I guess I wasn’t very friendly there for a little while, but slowly worked it out by the end of the year. Then I was more friendly, and then met the woman I’m with today for about two and a half years. Met her right towards the end of 2009. That was kind of the shift where everything finally started getting…

Andrew: So the new relationship was what really opened you up and helped you get out of this funk.

Seth: It certainly helped. I give her a lot of credit for… yeah. I was in a bad place in 2009 and it really helped me get out of that.

Andrew: What was your relationship with Leb [SP] like outside of work?

Seth: I don’t know. We were always very friendly and very much sort of buddy-buddy, but we weren’t friends before we started the business and we kind of became friends as we did it, but we always knew that there was a defined line between “We are business partners, we are not best friends from…” Both of us always kind of preferred it that way. I very much do not believe in going into business with friends and family.

If you look at statistically family business, they typically dramatically under perform. Non-family businesses in the same category, it’s really obvious than you think about it because it’s hard to go to your mom and be like “You’re fired.” So you end up putting up with inefficiencies and all this garbage that ruins the business. You put up with it because you can’t fire your brother or whatever.

Andrew: It’s hard enough to fire strangers.

Seth: Yeah. So you either put up with it or you close the business down or whatever. This is why family and friend businesses tend to dramatically under perform because you put up with stuff you would never put up with an employee or someone who’s not a friend.

Andrew: How awkward was it at the beginning of the interview when I got the person you were married to wrong?

Seth: [??] make it to this point in the interview…

Andrew: Well, we said it. You said no in the beginning, but maybe we should have made it even clearer.

Seth: That’s one of those things. When you say partner, people think you’re referring to business partners all the time. I refer to business partners like “My partner and I did this.” People in the business world tend to get it. “Oh, he means business partner.” But when I’m talking to people that are employed, just career-minded and all that kind of stuff, there’s always a moment where they’re like “Partner, or…?” Business partner, not life partner.

Andrew: Were you spending enough… Back me away like in the beginning of the interview where you just said, “Hey, dude, your basic facts are wrong. Thank you for having all these researchers, but if you can’t get the basic facts right, I’m going to correct you.” Push me back if I’m here, but did you also then at home get distant and is that what leads to divorce? I’ll tell you why. Olivia and I have been married two and a half years. I worry because I feel like we entered into an institution that’s bound to crash. If a plane crashed as often as relationships do, you wouldn’t get into it. And here I am happily walking into a relationship. I want to know what’s coming up. Even if I crash, I want to know what’s coming up. And better yet, if I’m going to crash, I want to know what’s coming up so I can avoid it.

Seth: I don’t know, entrepreneurs tend to have higher divorce rates. You can probably see a lot of reasons why. I mean, you’re apart a lot, stress levels are incredibly high, stability is not there, everything from financial to where we’re going to be living, whatever. Everything is completely up in the air, so unless you’re with someone that kind of accepts that, and gets that, and understands that things are always going to be kind of up in the air. It can be tough. There’s never one reason, there are a million reasons why it didn’t work out. It didn’t help, there’s no way it helped, because I was just constantly busy, and there’s just no way it helped.

Andrew: There’s the busy-ness, it’s also like you said, you don’t know where it’s going to be. Sometimes I envy my friends who have steady salaries, and have had them forever. I know that it can be boring, and I don’t blame them for stopping, and making different choices to get away from that. There’s a certain stability that comes in the rest of your life when your finances are stable, when you know from month to month, ‘Honey, this is how much money we’ve got. We’re going to be careful about where we shop, and if we do, then we’ll have this much at the end of the month, and if we don’t, then we know where we went wrong together.’ There’s a calmness that I feel comes from that, versus entrepreneurs. You look at even the best of the best, and suddenly they fall on hard times. The big mouth, Donald Trump, who always said how great he was, when he was going through some trouble, he was feeling depressed openly about it.

Seth: Yeah, not my favorite entrepreneur, but yeah. He’s a good example of a lot of things not to do. [Laughs] He’s fantastic on that level. Yeah, it’s tough. I mean, it’s really tough to be in a relationship and be an entrepreneur, at the early stages. Sure, later on when everything’s kind of stable and you’ve figured it out, you fast forward five or seven years or whatever, then sure, that’s fine. But right at the beginnings, especially that was our first company really, like our first big company that was starting to scale and all that, so everything we were going through, we were going through for the first time. So I was kind of always on edge, my anxiety was high, it was just not a good time to be in a relationship, especially married. Just looking back, there are just so many things that you would do differently.

Andrew: For example, what’s one thing that you could have done differently that I, Andrew, need to learn from about this?

Seth: I mean just separating work and personal time is the most common one that everyone always says, and it’s true. [Audio cut out] It’s really hard to separate them, but it’s so critical. Also, absolutely not bottling up. Actually, everything’s just standard answers that you would normally think are just Relationship 101, like separating your work life and your personal life is absolutely true.

Andrew: You would think that. I’m sorry, what were you going to say with the other one?

Seth: Being very open with how you’re feeling at the time. I wouldn’t talk about all the stress that I was going through at work and everything, and I would just kind of keep it to myself, and you just bottle it up, and if you have no one to talk to about that kind of stuff, it catches up with you. And you either end up with horrible anxiety problems, or you end up exploding or whatever. There’s no good outcome to not talking about how difficult and stressful and painful it is to do a startup, and the effects that it has on the relationship and everything.

Andrew: That’s still not something that I could ever talk to Olivia about, not because I can’t trust her with that information, I can trust her with that information, but when I’m going through that, I can’t talk about it. I can’t sit down and say, ‘I’ve had this frustration.’ All I could do is maybe vent about it and then move on, but the vetting’s never really very introspective.

Seth: You need to talk about it. I still struggle to talk about it, but I do. I’ve got to bring it up, because otherwise you’re going through it alone, and that’s not an answer. That’s not helping anything.

Andrew: The other thing that you were saying, that we need to separate work and private life, and you saying it sounds a little clich?©d, or you hear it so much. I feel I hear the opposite a lot. There’s this feeling that if you take even dinner without checking your Blackberry, or checking email on your iPhone, then you’re a wuss who’s not really committed to the company. And that’s the line that we feed other entrepreneurs, and that’s the line that entrepreneurs feed their employees, because they want to get as many minutes out of them as possible. We don’t often hear what you’re saying, which is, ‘Hey, you know what? If you’re at dinner, nothing’s going to break if you don’t check your email. If you’re away for a Saturday, everything’s going to be just fine if you don’t check in.’

Seth: Luckily, because of Technori, we’ve been able to meet a tremendous amount of successful entrepreneurs here in Chicago. And a lot of my favorite entrepreneurs, a lot of the ones that do just phenomenally well, they are good at taking off their weekends. They’re good at really enjoying their personal time.

Andrew: Yeah.

Seth: They have hobbies. They do things outside of work. I feel like that’s absolutely critical. And of course there are examples on both sides. There’s no question there are examples of people who are workaholics, they work 100 hours a week, they crush it out, and they do phenomenally well. But there are tons of examples on the other side, maybe just as many honestly, that they’ve learned how to separate them both. Maybe I’ve become slightly less efficient, I wouldn’t say that but let’s say I am, but I’m a hell of a lot happier than I was before, when I was just literally minimum 18 hours a day, crush it out, seven days a week.

Even if I’m not getting an insane amount, I’m just getting a ton done, I’ll take a ton over insane if it means I can actually have my weekends back. [Laughs] If it means I can actually go home and sit on the couch, or exercise, or whatever, and actually unplug. The level of happiness, the quality of life is just phenomenally different. And it’s just not worth it to ruin so many conversations by texting. And me, for sitting across from somebody and networking and all that kind of thing, you can’t be on your phone. It pisses me off when people do that to me. [Laughs] [??] I refuse to do it to other people, so what I do with people, they have my full attention.

Andrew: All right, I appreciate you talking openly about this stuff. I don’t get enough of it, and I want to get as much non-work conversation as I can, and still make sure that we cover all the work bases. So, there are two things that I wrote down that I want to come back to, and then I want to also tell people about Technori, where you just mentioned you are learning from other entrepreneurs and what you’re doing now. So, the first is: you said you grew too quickly, and that’s why this happened. What I noticed through the story is that you maybe could have continued to grow at this pace, as long as you didn’t change the software all at once.

Seth: Yeah.

Andrew: So, was it more about the software change than it was about the growth, and the way that was handled?

Seth: I mean, sure. It’s one of those things, it was going to happen eventually, it just happened all at once.

Andrew: I see. The foundation was just put together so quickly that it was bound to fall apart, and if it wasn’t the software, it would have been something else.

Seth: It would have been something else. I mean, our hiring policies were just way too fast. We were hiring people literally in one interview, 24 hours later they’re hired, which is a terrible way to hire people. We were doing everything wrong. So that it happened on the IT side, but it could have happened anywhere. And it forced us to completely change every single aspect, from the way we train our customer service people, the way we hire, to I mean everything. Every single thing you can think of, from having an employee agreement, all these things that just seem like default once you have a stable company, we weren’t doing any of that. So we were setting ourselves up for just disaster, eventually. It came in the form of an IT disaster. It could have come in the form of…

Andrew: Disaster with an employee?

Seth: Oh yeah, we had plenty of those as well.

Andrew: You did. What kind? What kind of disasters should we be watching out for? Don’t mention names, of course. And no specifics that could get anyone in trouble, but I do want to learn.

Seth: Yeah, I won’t get too specific. Just in general, and this is something I’ve been telling people at lot now, is that if there’s even one percent, something that seems off, like 99 percent about this person is just awesome and they’re great and I want to hire them, but there’s like one little thing that you can’t put your finger on, that just doesn’t sit right with you, that doesn’t sit right with your gut, don’t hire that person. Whatever that one percent is, it’ll show up. It’ll show up in the worst moment. And you’ll realize, ‘Oh yeah, that was what it was. That’s why I was thinking I probably shouldn’t hire this person.’ You’re bringing these people into your family, and when you’re a startup, it is like a family. So, you’re bringing someone in, and we had it happen over and over again, because we were hiring too quickly, that just one bad person would destroy company morale.

It’s amazing, even if you’re at 30 people, 50 people, whatever, how one person can really damage everything. And we had it happen a few times, and every time we’re just like, ‘OK, never again.’ And then we’d hire someone else that there was one little thing we couldn’t put our finger on that was like, ‘I don’t want to hire you, but everything else is just so amazing, I’ve got to hire you. It’ll make up for whatever this little thing is that we can’t figure out.’ And then it shows up, and you realize, ‘Oh yep, that’s what it was.’ And, it’s so tough to say the word patience to an entrepreneur, but when it comes to hiring, you can get amazing people. But if you’re not patient, you’re going to get really crappy people and it’s going to ruin your business.

Andrew: You turned things around. One thing you did was hire a CFO. First of all, is the company now profitable even though you’re not there?

Seth: Yes.

Andrew: Not only is it profitable, but based on the look on your face, I can see it’s doing pretty well.

Seth: Literally other than July, August, September 2009, we were profitable within a month of existence since 2004.

Andrew: You still own a big piece of the business?

Seth: Nope. I got completely out.

Andrew: You sold out? You cashed out?

Seth: To my partner.

Andrew: To your partner, right. So he owns the cash out?

Seth: He owns 100% of the company now. I’m out.

Andrew: Congratulations. Are you doing better financially because of this?

Seth: Well, I would say so. Yeah, it had been a while, so it was time for me to go. Insurance, as much as I don’t care about the ideas, it’s more about the fun of creating something. It would help if it had been something else other than insurance. So I was never really interested in insurance and it just started to get to the point of “I can’t do this anymore. I need something new, something exciting.” And honestly, something real, as far as real-world –

Andrew: Something you can taste, smell.

Seth: Something physically that I can hand to somebody and say, “I made this.” And they hand you cash as a transaction. I want that experience. I’m so tired of the digital world after a decade of building everything. I can’t touch anything I’ve ever built. I have a decade and I have nothing physical, literally, to show for it. Now it’s time to build real things.

Andrew: So if I understand you right, the turnaround came because you were able to patch the software and you ended up patching the software. You didn’t ruin your reputation because you paid people even though it was your system that was screwed up and it was eventually going to get fixed, you said, “No, we’re going to pay people.” You borrowed money to make sure that you could get over this hump, and once you did, the rest of the infrastructure was in place and then you fixed everything from the bottom up. You set yourself on a foundation by bringing in a CFO, better hiring practices, by unboarding people you hire better.

Seth: 2011 was back to growth again and then – I’m not part of it now but I talk to my partner every now and then and 2012 is about growth again. They can grow properly.

Andrew: I don’t think there’s an entrepreneur in all of Chicago, a tech entrepreneur especially, who doesn’t know you and doesn’t have good things to say about you. It is true and the reason is that you’ve helped build this community, you’ve blogged about what’s going on there at Technori, where people can read about what’s going on in Chicago. I’m looking for other websites I can give out. You co-founded Spark Chicago, helping to promote and encourage entrepreneurship in Chicago through six days of intense incubation and startup events. Did I get that right?

Seth: Yeah. That was last summer. I’m not sure we’re going to do it this year, but it was a fun time.

Andrew: That was in 2011. All right, and where’s a good way for people to connect with you and say, “Thank you” if they got anything out of this or say, “Hey, I’m going to be in Chicago and I’d love to come out to one of the events you’ll be in”?

Seth: Actually, I have a fun new email address. It’s

Andrew: You have

Seth: A friend named Josh who owns and a bunch of other domains hooked me up. Now, I’m going to start using it for fun. So, if you ever want to chat. Also, my website is I don’t have a contact page, it’s the “Let’s Get a Beer” page, and you just click “Let’s Get a Beer.”

Andrew: What’s the domain?

Seth: It’s just, my full name.

Andrew: So, people can click “Let’s Get a Beer” and you’re going to get a beer with these guys.

Seth: Yeah. It’s coffee more likely at this point.

Andrew: You’re way nicer than I am. I’ve got a webpage up on Mixergy that says “I don’t want to chat. Quit inviting me out for coffee.”

Seth: I absolutely believe in the power of networking. It’s incredible what happens when you start meeting everybody for coffees, beers, lunches, dinners. You do that for –

Andrew: It’s incredible what happens when your work doesn’t get done. I don’t know how they keep up with all this stuff.

Seth: I –

Andrew: Actually, you know what it is? It’s my own fault. I didn’t set up an organization here at Mixergy that could function without me. I’m going to now so I can take a break and actually go and have a beer, and I have been, so I’m not going to write the post for this. So if you don’t like the headline and you don’t like the way I described it, you can yell at me or at the team and we’ll fix it. We’ve got a team now in place to do that, and I’m going to do the same for everything else – scheduling guests and so on. By the way, scheduling – did I screw things up? I realize when we started the interview, maybe I didn’t – what were you going to say? You were going to say something.

Seth: Your previous point, yeah. You’ve got to create a business that can survive without you, whether it’s two years down the line or three years down the line or whatever it is. Otherwise it’s just – and that’s fine. My stuff is great. If you can pull 2 or 300K, whatever it is, everything from an insurance agency to whatever, those are great businesses. I love businesses where I can pull myself out of the equation and it still continues to scale. Along the lines of scheduling I just had us down at 11 on my calendar.

Andrew: I did too, but I realized as we started –

Seth: Time difference.

Andrew: Time difference, yeah. So I had us down for 11 Eastern, you were thinking 11 Central.

Seth: Sorry about that.

Andrew: I’m sorry about that too. I appreciate that we were able to get on here and do this interview. This is a really good interview. I’m grateful to you for doing this, glad we got to meet, hope we get to have a beer sometime, and more importantly, I hope my audience gets to meet you in Chicago when they’re there. Seth Kravitz, thanks for doing this interview.

Seth: Thank you. Thanks for having me.

Andrew: Thank you all for watching.

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