Welcome to the CEO Nation podcast, where we believe that true freedom is being able to do what you want, whenever you want, with whoever you want, by building a business that works for you rather than you working for it—and, now, to start uncovering how to get out of your own way and start building that business of your dreams, here's your host, Steve Richards.
Steve: Hey, guys. Welcome back to the CEO Nation podcast. I'm your host, Steve Richards. It's great to have you for another episode. I'm psyched today. This is not a normal interview for me and for us on this podcast. Today, we're joined by our friend, Greg Kraios. Hey, Greg.
It's really cool. We don't professionally know each other. Maybe eventually we'll do something together, but we've really hit it off personally. Really, oddly enough, Greg bought a house that we flipped and, through one of our real estate businesses, met my business partner, Brian, who some of you guys that listen know. [01:07.3]
He was like, Hey, man, this guy called me off a sign. I met him at the house personally. He's buying it. He’s paying cash. We negotiated a deal. He's a decision maker, I can tell you on the spot. You’ve got to meet this guy. It was really funny. He's like, Not only are we selling this house, and it was a really nice house, by the way, but I think you should interview this guy in the podcast—and here we are. It has been a couple months.
But, anyway, it was an interesting way how we met, but, guys, I'm really excited.
Before we get started, though, I’ll tell you, if you're new to the CEO Nation, look, the whole goal with the CEO Nation is to help hustling, grinding entrepreneurs transform into business-owning CEOs. We want you to learn how to get out of your own way and own a business that supports you rather than you supporting it, and really a business that works for you rather than you working for it. [01:58.0]
I think what happens with most people that get going in business is that they think they own a business. They really own a job and they don't own a business, and a business is very different from a job. Greg and I were just talking in the pre-interview here, which is always so good, by the way. It’s a half-hour of awesomeness, but we were talking about that difference with entrepreneurs and hustle.
Here's what's interesting about Greg, and then I'm going to let you maybe start with a bio, Greg. What we found really interesting is Greg is a success story of having exited a business that he sold here in Indiana, a tech business.
I'm going to let him tell you a little bit about it, but it was really neat to hear the story. I don't think he has had a super-traditional path and I think he's got some really down to earth conversation that we can have here about structuring a team and how he grew a business. That's what I'm most excited about getting into, because typically we're talking to really successful guys, Greg, or gals that have exited the business just from a day-to-day standpoint, but it's not very often that we have people on and we've only had a couple of them that have actually sold their business, so that's really unique. [03:07.8]
Anyway, with that, I want to introduce you guys to Greg. Greg, can you start out by just maybe quickly giving us a bio, just a little bit of the stuff that you probably think is boring, but how you grew up, how you ended up getting into starting a business, just some basic stuff, so people get to know you a little bit.
Greg: Oh, man, very non-traditional path. I don't have a degree, never knew what I wanted to be when I grew up. Took a job at a call center in the mid-90s as the internet was taking off and got introduced to the internet and kind of saw what it was becoming. At that job, I met a kid who became one of my best friends and he became the original architect. I got to see him write the first lines of code and meet the three founders. It was three guys with an idea. [04:00.0]
Every time I'd meet up with my buddy, he would tell me that they were growing and it was really cool, and he was getting to build this really awesome software as they kind of shared some office space for a while. I thought, Man, this just seems like a really cool place.
What inspired me about ExactTarget was it was the first company I saw that had kind of a West Coast management style here in Indianapolis. I was doing contracted IT work and I was saying that it was office space.
Every day was kind of the worst day of my life. I hated driving into that job. It was literally sitting in meetings, debating whether or not we could wear jeans on Friday while the product sucked and everything else. I mean, this is what we spent our time on.
I decided to quit and didn't know where I was going or what I was doing. I was looking on ExactTarget's website and I always say that I went there for a job and I left with a career, and I kind of fell in love with this whole email marketing deliverability, anti-spam kind of problem. [05:14.0]
I worked there for about two and a half years and just kind of realized for a lot of reasons it was my time to leave. I don't do well in big companies and tons of structure. I just like to get things done, and the bigger the company is, the more layers, rules and other things you have to abide by. It just typically doesn't work for me. But ExactTarget had this wonderful culture, and everybody was working really hard and having a ton of fun doing it, and that just really stuck with me.
I left ExactTarget and kind of stumbled into the world of being a consultant. I didn't even really know where I was going or what I was doing. I had a company reach out to me and ask me if they could hire me to do some work for them. I said, “Sure.” Then the word kind of got out that I was consulting and I had other companies reach out and ask me if they could pay me. [6:11.0]
To your point earlier, I wasn't running a business. I was running a job. I was making a lot of money, multiples more than I made at ExactTarget. I was working less hours a week. I did that for about five years and it was pretty great, but I always was inspired by these ExactTarget founders, other entrepreneurs that I’d met along the way and thought, Man, I want to swing bigger. I want to see if I can do something bigger. The only thing I knew in consulting was, If I work, I get paid. If I don't work, I don't get paid.
So, starting a software company that was kind of like paid. How can I get paid while I'm sleeping? How can I continue to make money while not constantly doing something for it, where my input is an X and my output is Y? I want to know how I continue to make money. [07:11.2]
But I didn't know how to start a software company. I didn't know how to get that started. I was at a conference and a friend of mine was complaining about another company in the space and their software, and how it didn't really do what he wanted it to do. It was 2:00 in the morning and we were having beers, and I was like, Hey, if I can build a better product, would you pay me? He was like, Yeah, sure. I was like, I can see all the ways it should be engineered better.
I came home, connected with my buddy who was the original architect of ExactTarget, and over the course of a weekend, we built an alpha product. The next week, I showed it to my buddy and he was like, Wow, this is already outperforming what we [have]. Maybe three months later he was like, Okay, I think we can pay you. It has been pretty reliable. Everything has been great. [08:05.6]
So, I needed somebody to write up a contract. Turned out that I reached out to an attorney and a guy who came to work for them happened to be the former counsel of ExactTarget. I was like, Hey, I know him. We had lunch and started talking. He was like, Tell me what you're doing and what you're up to, and he helped me with that first contract and I got a paid contract, so I had my first paying customer. I thought, Okay, that's kind of cool.
He was like, What are you going to do with this? I was like, I don’t know, I'm not sure, and I kind of had this bigger idea. He was going to be my original business partner and probably more my fault that we didn't come to terms, and so I kind of sat on it for a year.
Then the managing partner of the firm that guy worked for happened to bump into him downtown and he said, Hey, man, what did you ever do with that software? What are you doing with that? I was like, I still have just the one paying customer. I haven't really done anything with it. [09:10.0]
He was like, Man, let's go have some beers and talk. We did and he was like, Look—he was really passionate about helping entrepreneurs kind of get that first step—here you need an operating agreement and the valuation should be this and you should raise X amount of money, and we should have this many options in the company and regular units and preferred units.
All the shifts were blowing by me. I was like, Wait, what? and taking notes. Luckily, the lady who was the original CFO at ExactTarget was a really good friend of mine and we just became close during my time there and stayed in touch, and luckily she was helping me out and advising me. She was like, Okay, here's what I liked about the operating agreement. Here's what I don't. She redlined it for me to go back. It was just with a lot of help that I was able to get it kind of off the ground. [10:06.6]
For the first two years, I didn't pay myself. I didn't take a salary. I lived off savings. I made consulting. I remember that during those two years, as I was paying an engineer full-time, we had a lady who came to do the sales for us for a little bit. I was not only not paying myself, I was paying out of pocket to go to conferences and I would think, I’ve got to be the dumbest guy in the world. Who pays to go to work? You go to work to get paid. I’m literally paying, watching my savings account dwindle down and while I drive into work. I was like, I'm nuts. I should just go back to consulting. My life was so good. It was so easy.
Steve: So funny, to pay money to go to work.
Greg: Yeah, it was true. I was paying money to go to work and I was like, This doesn't feel right. [11:03.5]
I would talk to people I know that have been entrepreneurs and they were like, No, you're doing it the right way. Most people, when they start a company, they want to make more than they did at whatever job they have.
They think they're going to be free and have more time on their hands. They don't realize they're going to work twice as hard and make half as much in the early days, and that's what you have to do to get it to a financially stable position, or you can go out and potentially get alone or raise a bunch of money, but then you're just working for other people. You're working for the investors, especially if they have majority control or other things.
I didn't want to. Again, I had a great job in being a consultant, but I didn't have a real business and I wanted to have real business. I want to have an exit. I wanted to build this thing up and, eventually, one day sell it if I was fortunate enough. [12:01.8]
It's always debatable. We closed our first seed round of funding in 2012. We sold it at the beginning of 2020. The alpha version was done two years before that, so technically I guess it was really 10 years, but technically eight based on the first seed round. It was eight years of an emotional roller coaster that I just can't describe, because no matter what you think you're getting into, you're going to get pushed so far past your limits and what you think you're capable of in just ways that you can't expect, but it's also the most rewarding experience that I’ve ever had as well.
Steve: That's awesome. Man, one takeaway, Greg, when you were talking is I feel like relationships matter a lot to you because, man, there was several pivots in that story you just told like, I happened to stay close to this person or this person knew me from this person or my friend brought this idea and I saw this problem because of my friend. [13:17.2]
That stuck out a lot to me that I think some people are bouncing through life and they get so closed minded that they lose sight of that. I know because I was in the tech business before, in fact, I might have told you this, but Scott Dorsey, one of the founders of ExactTarget, had a good hand in dashing my first… Did I tell you that story ever?
Steve: Our first startup ever before I left the tech world and got into real estate, we had a startup, and he heard about us and he had me come down to the downtown office. It was more [unclear 13:51.3]-wise.
It wasn’t that obvious, talking about it. This is terrible for the podcast listeners right now. [13:57.6]
But, anyway, this guy who eventually sold his company for a couple of billion to Salesforce here in town and Indy had me come down, and it was kind of an early version of LinkedIn back in 2000-ish and that didn't exist yet.
I remember Scott telling me, Hey, man, oh, now I see what you're doing. You know what? My sales guys spend their whole life collecting their Rolodexes. They're not going to put them online for everybody to see. They're not going to give their contacts away. That's like gold. As I walked out with my head down, he was like, Man. Scott Dorsey told me, These guys are finding stocks, and now it’s LinkedIn.
Greg: Yeah, and that resonates with me because the world of email is really small, and when I first started, I literally had people laugh at me when I told them what I was doing and they were like, Oh, that's not doable. You can't beat this company. They’re so much bigger than you. They own the industry.
I was like, Why? Why? Why should there be one? Why can there only be one? There's not just one brand of paper towels. There's not just one of anything. Competition is good. I think we can do it differently. I think they're strong at a lot of different things, but I also think they're weak at others. [15:12.3]
Yeah, those things can kind of hurt. I had people even through [unclear 15:19.6], I mean, you can't please everyone, but I never doubted that we were onto something and never doubted myself in terms of the vision I had and the people I surrounded myself with to make it happen.
Steve: Yeah, you said something before we started recording this. It's funny, I have a lot of people that come in different businesses, and I think a lot of you guys listening are probably in this boat or have been in this boat recently, but when the time comes to invest in your business by hiring or, more importantly, investing in marketing, people are like, All these other guys are already doing pay-per-click on these same keywords or people are already sending direct mail to the same list, or there's a booth at a conference that's right next to three or the people that are already… It's like, Why would they do business with me? [16:09.0]
It’s really interesting. You made a comment before we started recording that I wrote a little note here, but you said that the bar is getting set lower and lower, and sometimes I do feel like it's a race to the bottom with competition and I think that value really went out. I see people make decisions all the time, especially in our real estate business, people take our offer on their house that's less money than they're getting offered from more sketchy people and they just want to do business with us because they trust us to get it done right and there are so many intangibles that happen along the way that they're glad they did it.
Greg: I can't take credit for it and I don't know who it was, but somebody in our company has said this and it’s something I’ve latched onto. People want to do business with people they like. It's one of the things we talked about before we started recording. [17:02.0]
Restaurants. I eat at Ale Emporium four times a week, and the food is repeatable and the service is awesome. I'm there all the time. We've seen so many restaurants that we thought were very iconic to Indianapolis or to certain neighborhoods or whatever fail and not make it, and we've seen others thrive, and people will go out of their way to support the people that they like and care about that provide them that experience, and we're all kind of creatures of habit.
To kind of bring that around back to relationships, that's your most important thing. At 250ok, we started off really just selling to people I knew in my network and really focused on resellers and other things, because we knew that we had a 10-year product roadmap deficit to our big competitor. [18:02.7]
You always hear that SaaS companies should spend about 40% of their budget on sales and marketing, and we never really got close to that. 2019 was kind of the first year where, at the end of 2018, we thought we had not only parity in product, but probably a superior platform, and we can kind of back it up with our own data based on the big-name customers we had. They renewed year over year.
I actually tried to discourage multi-year agreements with our customers. They were like, Your competitor wants us to sign up for a three-year deal or five-year deal, and I was like, Yeah, I'm sure that they do and, yeah, that'd be great to have on our books, but I want to earn your business every year. Every year, I want you to have the choice, and if you want to leave, leave, but I want our back against the wall. We should be able to earn your business year in and year out, right? [19:03.5]
Yeah, I can lock you up in that or if you want to sign a multi-year deal with service-level agreements or whatever to report to you, we can explore that as well. Obviously, I'd love to have that revenue on the books three to five years out, but I'm not afraid to keep earning it either.
So, we’ve just tried to approach things differently, but we were able to grow just based on the strength of relationships and because people wanted to. They had a personal relationship with me or some other employee or whatever, and you never know who people know. It's the same way where I’ve had some of the best conversations as I travel a lot, just people I meet on a plane and I'm like, Oh, hey, I just sat next to this guy, but in the middle of a flight, I have a new potential customer. I didn't know who that guy was. [19:50.3]
We all, I think, are trained a little bit to stereotype, to assume and to guess and whatever, and I’ve been very blessed and fortunate to meet and know some very wealthy people and you'd never know. Some of the people I see that look like…what I know those people are worth, are probably struggling, you know? It's just those things that you never know, so I think relationships are everything.
Steve: Yeah. Speaking of that, I’ve got a few minutes here before we get into our lightning round, which our regular listeners will be happy where they can get to know Greg more.
What would you say to people that are in the throes of trying to hire their first employees and the team members? Is there anything that you can give us that you learned in those early years about the people that stuck and the ones that didn't, and your mentality about who to trust? Because in the beginning, mishiring can be devastating to a small business. One of those first two, three, four key hires is like throwing gas on the fire or water, and they both are clear liquid and they look similar, but they both have a very different effect. [21:09.8]
Greg: Yeah, there are a lot of ways to answer that, I guess. For me, I usually try to stick with people I knew or somebody that was referred to me by somebody I knew. That was hugely important. Either having a past personal or professional relationship with someone or someone said, Hey, I hear you're looking for this person and I think I know a right person for you, and then you can kind of go down that path based on experience, time, history and all that other stuff that I think are important.
But some of the mistakes I think I made early where you don't always get to have the luxury of choosing, right? In a case of, let's say, you're early and you want to hire a salesperson, and you can't pay them a base and they’ve got to kill to eat, like, Hey, this is commission only. That's going to narrow the amount of people that you can probably get, right? [22:11.0]
So, I think you just have to be really honest with yourself in terms of setting that expectation and what you expect them to get, like, Hey, I really only need this person. I know they're not going to be here five years, but if I can get six good months out of them, if I can get a 100k in new business out of them, if I can get whatever. So, setting very, I would say, achievable and smaller goals, and really understanding where they fit into the company and the stage of the business, because I saw this at ExactTarget especially.
When I started, I think ExactTarget was three and a half years old, maybe four years old. I think I was employee number…I think it was technically 70-something, but we were only 40 people as they kept track from the first employee, including people that were no longer there. [23:09.0]
It was a really fun time, but I started realizing that some of the upper management was starting to circulate out and some people were really good at kind of zero to three to five years or maybe zero to 50 employees, but not good from 50 to 300. I think certain people are better in certain stages and structures, and other things, and so it's unfair, but we all do it to expect something from someone who's not capable of surviving or thriving in that. I think if your expectations are more in tune and realistic with what you can get from them, such that neither one is disappointed, that's fine.
One of the things I said earlier was I think we were also Midwesterners at heart, right? We were sometimes fast to hire and slow to fire, and we saw those bad things and we wanted to give people second chances, third chances. Looking back now, it was probably better for everyone had we just pulled the trigger earlier and we saw some of those signs. [24:18.7]
I don't always think that we had the brutally honest conversations that needed to happen because I didn't always realize. I think one of the best skills that I got over time at 250ok was realizing that you can have difficult conversations without being confrontational, and those difficult conversations typically provide the best outcome and the most growth because you're just laying it all out on the table. As we talked about earlier, part of our culture was to challenge everything, make data, back it up with data and don't make it personal.
But I was fine with a lot of people challenging any decisions that we made as a management or executive team because I don't always have their perspective. I only have my perspective at the top, which is not the same as an account manager or customer support people, or our salespeople. [25:15.4]
Being able to create that, that system of feedback and having it be just truly honest and open without being confrontational wasn't easy, but I learned how important and valuable that was for our culture and our growth internally as well.
Steve: That's really good, dude. Do you know what I was thinking of? Have you ever read the Five Dysfunctions of a Team by Patrick Lencioni?
Greg: I am absolutely terrible and avoid all books like that. Honest to God, I am.
Steve: Here's what I’ll do. As we become better friends, if you hear about a book, I’ll listen to it on 2X in Audible, all cognition, dense it down to the three points that we care about, the visionaries, and then we'll go have a beer and I’ll just tell you what they are. [26:06.0]
Steve: And then we'll pontificate and an hour.
Greg: Yeah, I can do that, for sure.
Steve: Look what I do with Brian and the businesses. I'm like, Dude, I’ve had 17 podcasts, three books, two seminars, a mastermind, and I read 10 white papers. Basically, what I came up with is Brian can only listen to 30 seconds and then he's done.
Steve: He's like, How are we going to implement this? That's all I care about. Can we make money now? But it's this really cool book. I won't get into it now, but, guys, as you're listening to this, if you're worried about culture and how to build a culture like what Greg is talking about, it's called the Five Dysfunctions of a Team.
In fact, I read it one time in a prior business we had, Greg, and I turned it into a whole-day workshop, and it just talked about how there's no place for gossip and drama, and how the whole pyramid [is], to the top where it's trust. The very bottom rung that needs to go in place is good conflict, because if you can't have good conflict, people don't think they're heard. [27:02.3]
They sit in a meeting and they think, Why would I say something? Greg is not going to listen to me anyway. Then you have to get there, like, Fine, watch this. Then, when it doesn't work, they're like, I knew it, and there's no buy-in and they're like, No one asked me anyway. Then it just undermines the trust in the business, in the company.
It's a really good read on that, but you were making me think of that while you were talking, Greg, because I think allowing someone to be heard and really listening to them is really, really important. I think in the first business, EDS was the first company I worked at and the Defense Department was our client, but we had this disgusting building here in town that had Legionnaires' disease and all kinds of asbestos and whatever in Fort Wayne. Anybody that's listening to this, this isn’t any… They're like, Don't eat the ice because you can die. Don’t drink the water out in the community. [27:58.5]
But they had this old school thing called the chirp box and the chirp box was where you could write anything anonymously and stick it in there, and it was just so dumb. I mean, it was like every once in a while they'd be like, We went through the chirp box, and they would answer one and it happened to be the one that they probably had someone plant that, fit along, you know what I mean? They're like, Oh, this one fits. See, you've been heard, and everyone knew you weren't heard, and that’s really important.
Greg: That makes it worse, right? It's like that just makes it worse. Don't do that and not read all of them. That only perpetuates the problem.
Steve: There were some smartasses in there that I worked with because they hired a lot of us out of college, and they would write just crazy stuff and they would be like, Yeah, see. They would write stuff in there just to see if it got talked about, you know what I mean? They're like, No, we can prove you're not reading them. Anyway.
Greg: That was probably me. Maybe I’ve heard.
Steve: Okay, we have a few questions as you guys know that we normally ask. I want to ask you one that's a little different for you as we close out here, Greg. [29:07.6]
How was it to sell the company? I mean, was it when you finally got the wire, and I don't know if it came in options and cash and how all that. We're not talking about all the particulars. I mean, it was a healthy exit, I’m gathering, and once it was “done” done and the initial, whatever that piece was, and you knew it was going to happen, did anything weird happen? Was it like what you thought or did you have any…?
I just see professional athletes talk about where they win the national or the world championship of their sport and it's the most depressed they've ever been, because they were just thinking that was what they wanted and they realized that the journey all the way there was what they wanted and it was hollow. I mean, did you have a moment like that?
Greg: Yeah. Yes. I mean, that resonates so much with me and I can relate to that. I think a lot of it is when you have a goal, and I’ll back up for a second. [30:11.4]
I always say I never grew up poor. Poor to me meant you worried about food or shelter. I never had to worry about food or shelter, but I grew up broke and didn't have the same things that other kids had. Watched my mom work two and three jobs at a time. Struggled most of my life, living paycheck to paycheck, going to payday loan places to get money to go to a buddy's wedding out of state.
I know exactly what that's like and what it was like to know exactly to the penny how much money was in a checking account. For me, I never wanted to be successful for things. I want to be successful for freedom. I just wanted to be able to be done at an early point in life and enjoy time. [31:02.5]
So, as I kind of went on this journey and when you're broke and you hear people say, Oh, it's not about the destination. It's about the journey, you kind of want to just be like, Shut up. I don't care about the journey. I will literally crawl through crap if I have to, to get to a better place. Right? You hear that and you don’t [understand]. I didn't understand.
I really struggled with the sale of the company and why I struggled with it was because I knew that we had a very special culture. I had employees that would text me, email me.
Even their spouses would tell me at company events and they’d say that he or she has never been happier, thank you, or this is the best job I’ve ever had, thank you. Knowing that you're providing that for them and making their lives better, it felt better than anything I’ve ever done. [32:02.5]
When you've been laser-focused on something and it consumes all of your life because again, people think they're going to start a business that they're going to get more freedom in the early days, no. As you grow it and you build in the right layers and you surround yourself with the right people, yes, you can get some of that back and delegate, and push things down, but you're always going to be the most responsible person. Nobody's ever going to care as much as you do.
But as the sale happened, yeah, there was just a part of you that was a little empty. It's kind of like, Now what? That actually happened. Now what? Luckily, for me, as unfortunate as it is, COVID happened. While my life kind of slowed way down, the world slowed down with it, and so it kind of gave me time to not feel pressured with the outside world moving so fast to figure out, What do I want to do next? Why do I want to do it? What's really important to me now? And figuring out what to do with all this other energy. [33:15.8]
I think people that really start businesses and are leaders just have a ton of this energy that they can't explain to people and you have ideas in your head that you can't always get out, and this energy just needs somewhere to go, needs something to aim it at.
It’s always funny to me. People that know me will say, You can't sit still. Dude, I know you. You can't just retire and stop. I'm like, But what if retirement is just owning, I don't know, a restaurant or a bar where people come and be happy? I didn't need to make any more money. It's not even about money, but I can give jobs to people. I can give them some of this great experience. It can be something I pour energy into. Maybe it's flipping houses. Maybe it’s… Whatever it is. Who knows? Maybe it’s starting a nonprofit. There are all these things that you can go do with that, with that time and energy. [34:12.5]
Yeah, I completely relate to that and have gone through several months where I probably haven't felt that lost or confused in quite a while, especially when you've been so laser-focused for a decade.
In my late-teens, early-twenties, as I watched everybody I knew go get degrees and then even master's degrees and other things, I admired them because I literally had no clue and all the message that you get is if you don't get this piece of paper, you're going to be flipping burgers.
I'm like, No, it's kind of not my plan, but I know I don't want to be a doctor. I know that I don't want to be an engineer. I know I don't want to be an attorney. And your best advice is for me to get a general studies degree and I'm like, What do I do with that? How does that help me? They're like, If you go to something company and they want you to have a degree, you can get a job there. I was like, I don't want a job there, so why? It doesn't sound cool to me. [35:10.3]
But there weren’t enough people pointing me in a direction and I felt really lost at that point in my life, and then, for a while, I think doing kind of the tech support, IT outsourcing thing kind of filled the void. Then that came to a head for me really and that's when I quit. I was like, I just can't do this. I don't know what I need to go do, but I can't do this anymore.
That's where ExactTarget for me was a blessing. Again, I went for a job. I left with a career. It just pushed me down this path that I didn't see coming. Then for the last, I guess, 16 years now, I know more about email, anti-spam and other things than any normal human should know, but, yeah, coming from that place, I’m very fortunate to be home.
Steve: Yeah, that's awesome, dude. All right. Cool.…
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