Katalina Dawson (00:00.901)

Hello and welcome back to another episode of Career Path. I am your host Katalina. Today we are discussing the entrepreneurial journey. And with me to discuss that, I have the amazing Jack Gordon. He is so fun. If you haven't met him, make sure to stop and meet him at one of the events, because he's at almost all of the events. He is the founder of Web Recon and a serial entrepreneur. Jack, it is such a pleasure to have you on today. Thank you so much for joining me.

Jack (00:27.04)

is always fun being on with you. I'm excited to be here. I love talking about me, so even better.

Katalina Dawson (00:32.549)

Fantastic. Well, thank you. So normally we start this by saying, tell us a little bit about yourself and how you got to where you are today. But that is kind of the entire podcast this time. So we're going to skip that question and just jump into talking about, you know you always wanted to be an entrepreneur?

Jack (00:43.861)

you

Jack (00:55.852)

I didn't. This came to me kind of as I was hitting 30. You know, I started out, you know, my first job was at a comic book store when I was 11 in Chicago, which is just the best job you can have as an 11 year old, right? I made a dollar an hour. We're talking, we're talking, what are we talking, like 1980-ish.

And I went through the string of jobs that most teenagers go through. I worked at Burger King for two weeks. Only job I ever got fired from, by the way. I think I was just a little too flaky. I was always staring up at the space in those days. I was a lifeguard for actually a few years. I was a camp counselor.

Katalina Dawson (01:34.757)

What you do?

Jack (01:53.166)

pizza delivery, I worked in a movie theater, and then moved up to the corporate office, which is where this story really kind of starts.

Katalina Dawson (02:03.845)

What an eclectic collection of different jobs to start with. That is so unique. And what amazing work experience. You've got restaurant experience, movie theater experience. Didn't you say, I think you said movie theater. Pizza delivery, like lifeguard, a lot of different life skills rolled into a couple of years. That's incredible.

Jack (02:16.46)

Yeah, I did.

Jack (02:24.568)

Yeah, no, I felt that. And by the way, it wasn't just a movie theater. was the, I believe the world, certainly the country's first 20 screen movie theater back in 1987, before most movie theaters were these megaplexes. This was the very first one to get that big and right here in Grand Rapids, Michigan. So yeah, that was a really interesting, good experience. And by the way,

before I moved into the corporate position with that company, I also got some experience managing one of their other locations, or technically assistant managing. One of those, like it was a twin theater, two screens. And what a different experience, right? When you're working in a 20-screen movie theater, there's a lot of people, everybody has their job, they're all cogs in the machine. Going from that to...

being in management for a two screen theater with maybe four or five employees total, right? It's a completely different thing. And I learned a lot from that too.

Katalina Dawson (03:36.185)

Yeah, I'm sure you probably had to wear a lot of different hats in that position too.

Jack (03:40.782)

I became a projectionist, I became a janitor, I became a popper, I handled, well I mean I handled money at the big theater too, but just all the different things, right? Wherever I needed management comes second, right? I'm going and filling all the holes. In any case, it was from that that I actually moved into

Katalina Dawson (03:44.591)

Yeah.

Jack (04:07.798)

sort of an intern position in the corporate office marketing department. And I got that by the way.

because they had all these ideas, right? And I wanted, I really kind of wanted to act on some of them. And every time I reached out to the corporate office, the marketing department, my first non-family mentor, guy named Ron Van Timmeren, was my boss for like the next decade. Every time I reached out to his department for support, for help on doing fun, creative things.

They were always too busy. They were always too busy. So I said those magic words, what can I do to help? And they took me up on it, like immediately. And I started splitting my time between managing this little theater, assistant managing this little theater and going into their corporate office and just, you know, being the grunts in the marketing department, right? Helping to ease their load. And like I said, I spent the next decade

Katalina Dawson (04:45.72)

Okay.

Jack (05:12.718)

kind of rising up in that infrastructure to the point where I became like the guy that was negotiating with all the film studios on advertising revenue shares or spend shares technically and placing ads and writing content for the movie theater world. And that was...

That was a really cool job for somebody in his 20s. it really did kind of open my eyes to learn, like I said, my mentor there really, really can help me learn what it's like to operate in the world of business. And I went to my first couple of conferences with that job, Show West and Show East, which now is CinemaCon Show West in Vegas, and then Show East.

Katalina Dawson (05:48.088)

Yeah.

Katalina Dawson (06:11.301)

cool.

Jack (06:14.242)

Same kind of thing, but on the East Coast, either Orlando or Atlantic City. And they were cool, right? That was something I'd never seen before, right? That was just everything. And getting, and you know, by the way, those are the kind of conferences that people like Arnold Schwarzenegger and Tom Cruise and Martin Scorsese show up to to talk about their new movies that are gonna be coming soon, right? I got to see movies.

Katalina Dawson (06:23.62)

Yeah.

Katalina Dawson (06:40.953)

That's awesome.

Jack (06:42.808)

I got to see movies way in advance of their official release date, right? Because they want the movie theaters to see what's coming and be excited about it. So anyway, I did that for, like I said, I did that marketing department gig for a good decade. And then at that point, I got the entrepreneurial bug, right? was, while it was a fulfilling job,

Katalina Dawson (06:46.339)

of land.

Jack (07:11.692)

you know, it was not particularly lucrative, right? It was a small, you know, was a small business and a family run business and there didn't really seem like any place to go that would be, you know, would be, help me kind of get into my thirties. So I started thinking about, what should I do here? What should I do next with my life? And the idea, you know, of course in the nineties is when the internet happened,

And it became my job to learn about the internet, right? To figure out how we could use it to support the business. And so I did that. And I got to a point where I thought, you know what, maybe I can do this on my own, right? And I've managed to.

Katalina Dawson (07:56.835)

So that's when the entrepreneurial bug really kind of bit you is when you had this feeling about branching out and being able to do marketing specifically on your own or a variety of different things with technology.

Jack (08:11.502)

Yeah, well, it took me a little while to really hone in on that. That's a really insightful work actually. I started out thinking, you know, I know how to build websites, right? And so I'm just going to put myself out there. And please, please, please forgive me for the language I'm about to use, but that is called the shameless horror stage of entrepreneurship. I went out, I went to banks, to jewelry stores to manage to keep the company that I've worked for, the theater chain as a client, right? But I went out everywhere and started

Katalina Dawson (08:14.467)

Okay.

Jack (08:40.526)

trying to get clients. And what I learned in that first year of doing that was that web designers are a dime a dozen, even back then. And my skills were not, you know, at a really competitive level at that point. So I had to that forced me to sort of, you know, I mean, I had some success, right. But I just realized I had huge imposter syndrome. And I realized

I can't really compete with what's going on out there now.

Jack (09:17.954)

took a moment to reflect. And that gave me, I think, my first big epiphany of that, which was, I just spent technically 12 years in the movie theater industry. I went to their conferences, I speak their language, I read their magazines. In fact, I was advertising in their magazines, right? had connections all over the place. Why am I not taking what I've learned from all of that?

and focusing on that industry with whatever skills I do have. And that was so inspiring to me, that idea, that I dropped all my other clients and I went right to work focusing on movie theaters again. And the two big things that I did was I would build and maintain websites, keep them updated with all the new movie information and show times and stuff like that.

Katalina Dawson (09:53.829)

Yeah.

Jack (10:15.606)

And then the other thing was building a weekly email newsletter. And that would have all the new movie information coming. All the old movies leaving would be featured, the full schedule, special events, free offers, popcorn on your birthday kind of things. A trivia question, right? I built this whole cool newsletter thing. And actually,

did that when I was working for the theater in the 90s, right? That was one of the things that I did working for them and then I was still doing just for them. So I went kind of back to that idea and just completely invested myself in getting more theaters that I can do the same kind of work for and really start to build some scale, right? Because 90 % of what every theater needs in its weekly communication to its customers is the same, right? The movie description.

Jack (11:14.912)

same. The trivia question can be the same. You know, all the information about the theater and everything. And then the stuff that isn't the same, it's all data. And so that's where I kind of really got my first taste of working with data was, all right, I, you know, I got to a point where it taking 80 hours of manpower every week..

Jack (11:43.054)

gold out all the newsletters for all the theaters that we had brought on as clients. It was a lot, you know, for a one man show, it's, so I got some, I hired some help. And it was a kid, right? It was a college age kid. And, you know, he looked at that, he looked at my process at what I was doing. And he just looked up at me and said, you know, you can write a program to do all this. Boom, there's my next big epiphany. Of course, it wasn't mine. It was given to me.

Katalina Dawson (11:47.542)

Yeah, that's a lot. Yeah.

Jack (12:12.718)

But holy cow, right? I mean, you're right. You could write a program that would do all the custom parts, right? The weekly show times for that particular theater, the what's leaving, the what's coming, any special events, stuff like that. That's just data. So we worked on building that. It took about a year on building out a really, really, really cool, totally unique

platform that would handle that process. And that became the company. That really defined, fact, the name of the company was Front Row Marketing. And I did that just because I didn't have any other great ideas and I came out of this movie theater industry. I had no intention when I left, when I started doing that, to be a movie theater based company. So that was actually serendipitous. And I had the perfect name for it already.

Jack (13:11.95)

So I took this and I went out to their conferences as an exhibitor this time and we launched this program. It cut that 80 hour work week down to four. And the four hours was basically putting the data in the database so that it could then save us those other 76 hours of putting it all together.

Katalina Dawson (13:26.061)

my gosh.

Katalina Dawson (13:36.995)

That is the power of automation, the power of database, computing, love it. And I can see in your story, these little breadcrumbs of leading to where I know you from, but I'm still also kind of lost. I'm like, my gosh, you're so in this movie theater cinema world. Now you've kind of got this data, you're building things, but how did you get from the cinema world into the receivables world?

Jack (14:06.188)

That's a pretty tragic story, actually. I sold, I'll spare you the whole story, but I sold the company, right? I didn't really invest too, but you know, was a good time. You know, we were like two months away from having our first baby. You know, money was, you know, even though I was having success with this, right? It was still a pretty small company.

And this other company came in that did monthly newsletters for their clients, which were like bowling alleys and restaurants and stuff like that. Right. And they said, we really want to be in the movie theater business and we really want to buy your company. And if you don't, by the way, we'll just, you know, put together the resources to compete. I like, I, you know, I thought about that.

And I ended up selling it to them and they were a disaster. There's no way they could have put a million dollars into competing, right? That was a total bluff because they were on the verge of falling apart themselves. they did fall apart about a year after I sold to them. And the only profitable part of their company was the part that I sold to them. And so they took that, just that part of the entity and they resold it to another company.

which is probably the one I should have sold to in the first place if I was going to sell, right? But, you know, I learned a lot from that experience. And, you know, by the way, here's a big learning. Most of the money I got for selling a company to them was in stock. And so when they fell apart, so did all of my, all of my compensation, right? It wasn't something I could cash out of easily.

Katalina Dawson (15:53.838)

Katalina Dawson (15:58.725)

Gosh.

Jack (16:02.688)

at all the experience. Right. So anyway, I went to work for the new company that bought that but you know what I had built and you know, just to kind of help them with the transition and you know, see, what they're you know, kind of as the godfather of this product, right, what I could do to help. And they they were a great company.

Katalina Dawson (16:02.894)

Ouch.

Katalina Dawson (16:13.327)

From them, yeah.

Jack (16:32.526)

guy named Brett West. I won't exactly say he became my second mentor, but he was a really smart guy. And the company was called CinemaSource and he subsequently sold the whole thing for gazillions of dollars. But what he did was, you how you can go online and see all the showtimes for all the theaters in your area in one place or like a newspaper, like

Jack (17:01.71)

You know in a regional You know in a city right though the list all the he's the guy that Did the work of compiling all of that data from every movie theater all over the country putting it all into a database and then reselling it to every media that wanted to publish, you know showtimes or movie and

By you know so his first choice was he would give theaters a little program that would create an FTP connection and Automatically sends their showtime data from their POS system to him and The theaters that wouldn't do that He would he would take it by email or fax the theaters that wouldn't do that He would have

He had his own little call center, right? He'd have people call their recordings and transcribe all of the showtimes off of their phone. Yeah. Or you take them off of their one. By sheer tenacity, one way or another, this guy built a machine that housed all of the showtime data for all of the theaters in this country. And he turned it into a money printer, right? Because now he could sell anybody, anywhere that data.

Katalina Dawson (18:01.891)

Pull in? Wow.

God.

Jack (18:24.928)

and they can use it in whatever it is they do. And so that was really inspirational to me. And I bet you can see that as another breadcrumb. So I did that for about another year, but technically I was a salesperson and that's not really what I wanted to do. So I parted ways on friendly terms and

Katalina Dawson (18:36.516)

Yeah.

Jack (18:54.798)

started really looking for, know, what is it I'm gonna do with my life? And a friend of a friend was an attorney for this collection agency. And here's where it starts getting, you know, more recognizable. And the owner of this agency was old. He'd been running it. He was the second owner, the first one and him both ran this agency for 35 years. And...

He was ready to retire, right? He was old, was cranky, he was not in good health. And he burned a lot of bridges. And so the company had shrunk, right? He had hospitals. And by the time, you know, he was ready to sell, he'd lost all of his hospitals. And so here I am thinking, you know, I just built this amazing company, right? And it is succeeding, you know, not without me, but...

Katalina Dawson (19:29.701)

You

Jack (19:53.89)

I feel like I have a skill, right? I think I could do this. I could come in and turn this company around and I wouldn't have to dirty my hands with collection work because what do know about that collection? And boy, was I naive, right? I mean, what a disaster that whole thing was, right? That became...

Katalina Dawson (20:07.267)

Hahaha

Katalina Dawson (20:10.957)

It's a difficult industry to come into not knowing anything because it's a very complex industry.

Jack (20:16.238)

Really, I do not recommend that strategy. Don't take all of your savings and dump it into something that you know nothing about. That's kind of a loser strategy. But for some reason, I thought it was a good idea and I persuaded my wife to go along with it even though she thought it was crazy. And so I bought this agency. It took about three weeks for me to realize just how

completely screwed I was. And, you know, mean, there's another couple hours of stories I could tell about that. In the interest of time, let's just say... There's a lot of horror stories, and I'll be first in line. I...

Katalina Dawson (20:47.086)

Yikes.

Katalina Dawson (20:57.859)

Yeah, we'll have to bring you back on and hear some of those for sure.

Katalina Dawson (21:06.191)

Gosh.

Jack (21:10.414)

I hung around for four and half years. I tried my best to build it. The best I could do is kind of stabilize it. And by the way, in those four and a half years, I took two paychecks. Yeah, it was a hard business. My wife had a good job, right? You know, we really, really depended on that for those years.

Katalina Dawson (21:24.837)

How did you even afford rent? That's insane.

Katalina Dawson (21:35.801)

Thank goodness. Yeah, that's rough. My gosh.

Jack (21:37.102)

Yeah, so like I said I stuck around for four and a half years I You know the lawsuits started to come in right the consumer lawsuits there was litigation Between me and the old owner because you know guess what he lied about everything and due diligence And

Katalina Dawson (21:57.605)

no, and then you inherited that. god.

Jack (22:02.862)

So it was so stressful and it so difficult and it took a huge toll on my marriage and it took a huge toll on my sense of self, right? I mean, how could I have stumbled so incredibly badly with this move that it really never would have been.

Katalina Dawson (22:12.345)

Yeah.

Katalina Dawson (22:19.909)

Yeah, you went from building a successful business that was able to be sold and resold and doing so well. And now you're like, I'm over here in a corner taking two paychecks. don't know what I'm doing. I'm going to court all the time. my gosh. What a 180 right there. Jeez.

Jack (22:37.374)

It was the absolute hardest period of my life. And finally, on the day I got my third consumer lawsuit in 2008, I finally said I'm done. I don't have the resources for this. I don't have the constitution for this. I'm not getting paid, much less being paid enough to make it all worthwhile. I hated it, right? I just hated it.

Jack (23:07.022)

You know, it really done a number on me. So I found a buyer, another, another agency that was, about not, like in Kalamazoo, right? Not, not even an hour away from here. and again, in the interest of time, I'll just, I'll just skip to the spoiler. that was a disaster as well, right? They bought it. The guy that bought it wanted his grandson to run it.

Katalina Dawson (23:26.955)

Okay.

Jack (23:36.146)

And the grandson had no interest and the grandfather died before I got old. And yeah, it was just, it was all so messy. So there was a little more litigation there.

Katalina Dawson (23:39.685)

no.

Katalina Dawson (23:46.689)

my goodness. So, all right, now you're in the industry. How did you get back up on your feet in the receivables industry and end up with Web Recon?

Jack (23:58.99)

Yeah, so, you know, I don't have any, I don't have any, I don't have any like big ah-has to share or, you know, transitionary insights or whatever. What happened was I stole it at the end of December 2008. My plan was to get a job somewhere, keep my head down for a while.

you know, just kind of go home and stay in the fetal position until I kind of got back on my feet and then really figure out what I want to do, right? That was the plan. It seemed like a good plan. But the economy crashed in December of 2000. We were losing hundreds of thousands of jobs a year. So finding a job, much less a stable, you know, a good one became almost impossible. And so I just had this one little weird, crazy idea in my back.

Jack (24:58.03)

And that was, you know, I had now been sued by three consumers in the year 2008 for completely baseless. Well, two of them were completely baseless. The third one was a setup, right? The attorney was already a professional, you know, consumer rights attorney who had a phone recorder and a script and, you know, put his client down and just kept on baiting us until something

Jack (25:28.71)

my collection manager said something wrong. Exactly. And, you know, that really sort of motivated me to think about that problem, right? There's a lot of collection agencies out there and almost all of them are better than mine. Right? I'm not really making the world a better place here by running an agency.

Katalina Dawson (25:31.609)

So like a form of entrapment. Yeah.

Jack (25:57.762)

But what if I could take this new problem of this explosion of consumer litigation and create something that addresses that problem? Maybe I can't solve it, but I can make it better. And that's where we're at.

Katalina Dawson (26:13.487)

So you're somebody who tends to look at things and say, hey, here's something new, technology, how can we apply that? Or here's where a deficit is, how can I fill that void? And that's where you become the entrepreneur each time.

Jack (26:28.142)

So, yeah, so here's the thing. I had now spent almost five years in the collection space, right? Reading their magazines, speaking the language, know, crash course and everything about how to do this, which obviously I did not pass that crash course. you know, listen, I will never say I was good at running a collection agency, but it did give me this core knowledge and experience.

Katalina Dawson (26:48.677)

You

Jack (26:57.718)

in the industry and my new, my next really aha moment came when I thought about this problem and how is it something that I can help address for the industry and the movie theater marketing company that I'd built, right? The working with data and databases and building something

you know, that's unique. I thought, what if I could bring these two parts of my life together in a way that I take the experience of running the agency and being in that world and I take the experience of developing database stuff, database driven software and put them together, right? And, and what can I do with that? That would help. it, you know, the, the plan kind of wrote itself from there. Right. I started, I scraped together

Money I really didn't have, like $250. I hired a developer in India and he built me a very, very crude beta of what something like this could look like. And it consisted of you uploading a bunch of names and checking the database and then telling you on the screen,

if any of those names show up in the litigation database, right? That's like nothing. Right? That was a step though. Very, very crude. And that ready for prime time. However, I took it and I ran with it, right? And I started putting a little email juice out there into the industry and I got a few takers.

Katalina Dawson (28:33.925)

It's crude, yeah.

Jack (28:54.67)

that was enough to give me the encouragement to keep going. And I actually, listen, I hadn't made money in five years almost. I waited a little longer and I put everything back into developing this product further. And it just really paid off. Once I kind of hit a certain threshold, I won't call it even sophistication, but something that was

Katalina Dawson (29:05.145)

Peace.

Jack (29:24.694)

not incredibly crude. We had the data, we had a database. So I added a search engine and started making that scrub process a little bit more formal and traditional. Then we added a whole bunch of other tools over the next few years. And I started taking a paycheck about

Jack (29:49.934)

maybe a year in, I replaced my wife's income about four years in, four and a half years in, and then of course she hated her job and she immediately, as soon as I told her she could quit, she quit. And, you know, we're...

Katalina Dawson (29:57.418)

wow!

Katalina Dawson (30:07.685)

That's gotta be hard for like the first year to stick with it and not be having that full income, but just to keep going. Wow. That takes a lot.

Jack (30:20.972)

I mean, listen, there's a lot of stress on a journey like this. It's not all fun and sales and growth. It's a lot of putting your nose down to the grindstone and working through challenges.

Katalina Dawson (30:24.975)

Yeah.

Jack (30:46.186)

effectively a one man show other than the programming part because I'm not a coder. So it was a one man show for the first couple of years, right, which I did all the tech support, I did all the data acquisition and importing and, you know, web design, which, you know, my skills were even more out of date at that point than a years earlier. But you know, I held it together, right?

Katalina Dawson (30:50.371)

Yeah.

Katalina Dawson (31:07.685)

you

Jack (31:15.31)

Over time I got better and over time I was able to bring in more people who could fill in some of my deficiencies to the point where, you know, I have a great group. of people, my key people have been with me now all for like at least 10 years.

Katalina Dawson (31:34.009)

That's incredible. I feel like there's so much more to this story, talking more about those hard times and how you got through them, that leveraging that team around you and finding a team of really good people. I know you and I even had a little conversation about how you found the developer that you ended up working with and how unique that was. I would love to have you on again for a part two for this so that we could dive more into that. But unfortunately today we are out of time. I could keep talking to you forever though.

Jack (32:03.374)

Well, we didn't even get into the sale.

Katalina Dawson (32:03.749)

Yeah, well, that's why I'm like, we're gonna have to do a part two. But thank you so much for joining me today. It was such a pleasure, Jack. I really, really appreciate you sharing all about your experience and the trials and tribulations that are the entrepreneurial journey. It's incredibly hard. And I really appreciate you being open with sharing that.

Jack (32:26.574)

Well, it's my honor, right? It's my pleasure. I'm so glad I'm in a position where I actually have some positive things to share. And by the way, you know, I share a lot of those same traits with our mutual friend Adam, right? He's been an inspiration to me on this journey as well. I would like to think, you know, I've been a little bit of an inspiration to him too in some ways. But he has a lot more energy than I do.

Katalina Dawson (32:52.581)

Yeah. He does have an incredible amount of energy. I agree with you. Well, to our listeners, if you have any questions, comments, or what you would like to see us discuss next time when Jack comes back, please leave it in the comments below. Otherwise, we look forward to seeing you in our next episode. Thank you.

Jack (33:12.184)

Thank you.

Katalina Dawson (33:15.45)

Okay.