Episode 171: Free Trials (and Tribulations) with Kyle Racki

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Greg: 00:01 Hey everyone. It’s Greg Strauch with Two-Brain Media. On this week’s episode we talked to Kyle Racki, CEO and founder of Proposify. We talk about Kyle’s new book, “Free Trials (and Tribulations),” along with learning more about Kyle’s life experiences that have led him to become a business leader. Subscribed to Two-Brain Radio to hear the very best ideas, tips and topics to move you and your business closer to wealth.

Greg: 00:26 Two-Brain Radio is brought to you by Two-Brain Business. We make gyms profitable. We’re going to bring you the very best tips, tactics interviews in the business world each week. To find out how we can help you create your Perfect Day book, a free call with a mentor at twobrainbusiness.com. We’d like to thank another one of our amazing partners, Level Method. As a CrossFit gym owner, I know retention is key to keeping my business going for years to come. Retention is not easy though. People want to see success and if you don’t show them early they’ll find a place that does. This is where Level Method comes in. With Level Method, you are now able to guide your members through an amazing structure; it’ll give them a path to success. Once you have success, you instantly have motivation for them to continue, which will now be delivered to your members. Start systemizing the creation of powerful moments for your members today. Go to levelmethod.com to book a free call.

Chris: 01:20 Hello Racki, welcome to Two-Brain Radio.

Kyle: 01:22 Hey, thanks for having me Chris.

Chris: 01:23 Yeah man, it’s a real pleasure. And you know, I got to meet you in person long before this book came out. You even mentioned back then that the book was coming, so I was anticipating it. It was even better than I’d hoped. So today we’re going to be talking about Kyle’s book, “Free Trials (and Tribulations).” I’ve got my well-thumbed and often-folded copy right here, but Kyle, you know, the listeners would love to hear your story first. So go ahead and I’ll let you tell it.

Kyle: 01:47 Sure. It goes back a while. So just kind of give them the broad overview, I guess. I run a company today called Proposify, which is a SAS business that helps thousands of teams write proposals, write, send and track. So the kind of the whole end-to-end process of that. We’re about 70 people, we’re based out of Halifax, Nova Scotia, and we’ve been on this ride now for five years. But prior to that I used to run a web design agency called Headspace—not the meditation app, which people often get confused by; just a really good name. Did that for about five years. That was the first business that I had started, did that when I was 24 and actually met my business partner Kevin, who’s 20 years my senior and we’re still together today running Proposify. So that’s kind of a brief work history, where I was a graphic designer by trade; went to college for that.

Chris: 02:32 OK. So we’re going to get to the “how to build a business while getting punched in the mouth” part later. But in the book you say you’re not a born hustler, so why did you want to start a business in the first place?

Kyle: 02:45 Yeah. You know, the idea of sales always really scared me, which is kind of a little bit ironic. Running a SAS business that helps sales teams with sales and doing a lot of speaking about sales. You know, I was never kind of the scrappy hustler in the sense of like the ones slamming cold calls and going and knocking on doors. I was always a little bit more shy than that, you know, but I wasn’t the kid—like if you ever hear Gary Vee talking about this stuff, he’s like, “When I was six, I was, you know, stealing the neighbors’ flowers and selling it back to them and getting other kids in the neighborhood to sell lemonade for me.” And that was sort of the Gary Vee thing. That was never me. I was kind of like the quiet artsy kid drawing.

Kyle: 03:26 So the idea to become an entrepreneur, which just happened kind of organically in my twenties when I was a graphic designer at an agency, and I have to thank the bad bosses that I had. There were these guys running these agencies really uninspiring. We had no idea what was going on with what were y’all trying to do? Maybe that was the millennial in me, but it sort of just inspired me like “I can do this.” They’re just going and finding somebody who has a web contract or whatever and I’m the one doing the work. Let’s just cut out the middle man and I’ll go out and find the web contract and do it right. So that was kind of where it started. Just the freelance lifestyle, living life on my own terms, being able to work from home, choose my contracts. That was really what appealed to me, and in order to get that I had to get out and kind of hit the pavement and find clients.

Chris: 04:15 What was that first transition like for you when you were working for an agency and then you decided, “I’m going to go out on my own and have my own agency”?

Kyle: 04:23 It was terrifying. Now it started as freelance so it was a little easier. It wasn’t like I was going and renting office space and hiring people, but yeah, it was always really scary. I found that because I wasn’t as—I didn’t think I was a good salesman, but I knew that I was good at what I did. I knew that that clients were happy with my work and I knew that I was professional in the way that I dealt with them. So because of that, it was actually, all I needed to get was a couple of contracts, make those client’ really happy and then they would refer other people to me, and eventually it was kind of the reputation in my local area that was sustaining me. I kind of went out the first month and just, you know, went to conferences and handed out business cards, got a couple of jobs and then from then on as a freelancer I didn’t actually have to do any more sales. They just kind of came to me that way. So I was like, “Well, that’s a lot easier.” It’s a lot easier to do that than to try to have to sell something.

Chris: 05:19 It’s interesting that you bring that up and listeners are going to hear later on why I think that you got a lot of sales training from a very early age, but so how did the process go then from owning Headspace to another business and now into Proposify?

Kyle: 05:35 Yeah, the agency was a massive lesson over the course of five years, many lessons, really, of what not to do, how not to run a business. And I learned the hard way, you know, a lot of different things from how to manage a team and inspire them and motivate them and how to go sell larger contracts and everything about owning and operating a business, I think that I failed miserably at it, but I’m also grateful to have had those lessons because they helped me succeed with Proposify. The transition between the two was really ugly and really messy. Essentially what happened was we started getting into building SAS products internally in the agency, mainly because we hated running an agency. We hated trying to sell one-off services. And Kevin, my business partner actually came from a product background. He had actually sold coffee back in the 90s through e-commerce. He had Manatee coffee in Florida, which he ran.

Kyle: 06:35 And yeah, we started getting into the product stuff mainly as a way to sort of build some kind of recurring revenue. But we always had, you know, these different harebrained ideas for different products. We never really took the lead start-up approach and went out and validated them properly. So we just kind of spun up different products, realized there wasn’t a market and moved on to the next. And then I remembered about this whole idea that I had back in maybe 2006 for proposal software. When I was working at agencies and then going out on my own, we always had to write proposals and I thought, “Well, this is a huge headache. Wouldn’t it be easier if there was kind of like a basecamp-type system to manage all your proposals. Just sort of sat on that idea for years. And then fast forward to 2011, 2012 we’re like, what product should we do next? Well let’s dust off this little idea and give it a try. Ended up gettin it into some people’s hands even in a very early stage. And even though our product sucked, the feedback I got, a problem was, “Oh my God, I hate writing proposals. I have to do it every day or every month. It’s the worst part of my job. If you can build anything that will make that easier, we’ll pay you money.” So that was sort of like the first indication that we were on the right track and kind of moving towards something. Getting it launched and then selling off the agency and going full time into it was a long and arduous process. But we finally got there.

Chris: 07:58 I think a lot of entrepreneurs maybe have that blank-slate fantasy of “if I could start all over with a brand-new company knowing what I did now, here’s what I would do.” But the reality is like it’s very hard to kind of shut one company down and ramp up another. So how did you work through that process of focusing on Proposify and you know, taking your foot off first base like you had with Headspace?

Kyle: 08:23 Yeah, you know, I think there’s always a bit of a leap of faith with any businesses endeavor, right? You try to get enough validation to go, okay, well there’s a market, we’ve got some good customer feedback. Like, it all makes sense. But at some point there is a bit of that like jump off the cliff and hope you land on your feet. So I think we were there with Proposify, we were never really sure it was going to take off. There was even periods where I really didn’t think there was any market there, there wasn’t even really competitors at the time. So kind of that was a bit of a scary thought. I’m like, “Wow, nobody else doing this or maybe only one other company is doing this. How big is the problem?” We were incredibly fortunate with our timing because the whole proposal software industry really took off in the last couple of years and there’s a lot of competitors now, but it was far from a sure bet. I think actually what really helped us, in a sick sense, was the fact that our agency business wasn’t doing well. So it was kind of like, well we can stay stuck in this, you know, shitty business that we’re losing money all the time and completely stressed or we can try something new. Maybe we’ll be in the same spot, but at least it’s different. At least we can kind of start fresh and not have all the baggage from that other business.

Kyle: 09:38 So I think, you know, the process of getting it sold, and when I say “sold” it’s with double quotes, right? We basically got rid of it. We got it into somebody else’s hands. We didn’t make a cent off of it, if anything we lost money in the transaction. But it was really just the act of like, okay, we need to file that away, start a new chapter and move forward. And luckily after six months of doing it full time, we started to see significant traction.

Chris: 10:04 One thing that impressed me from the start about you, Kyle, is your ability to shoulder risk and just appear completely unfazed. And we met either in Toronto or San Francisco with the Martel Group and I think at that time, Proposify wasn’t even profitable yet, but you were just completely calm about it. Where does that come from?

Kyle: 10:29 Well, I think when we talked, when we met, not profitable, it was really because we raised money. So we did have cash in the bank, but you know, were currently running at a loss, which all all start-ups who raise capital do that, they spend ahead of revenue. But yeah, risk tolerance, I think there is a certain amount of risk tolerance that I have or just maybe an ability to stay calm in stressful situations. I don’t really know where that comes from. I mean it certainly as a child I had to, in a lot of ways, hold in my feelings. I had to kind of internalize that stress and just sort of push through it so it could have come from that. You know, I wasn’t really allowed outbursts as a child, you know what I mean? Whenever I saw TV show where a kid was like, “I hate you dad!” I was like, “Oh my God, I would’ve got like, my head knocked off if I tried that.” So it could come from that. Just sort of like just being able to bear down when hard times come.

Chris: 11:29 Let’s get into that now, Kyle. So tell me about your childhood and how that has prepared you for entrepreneurship because you know, part of what makes “Free Trials (and Tribulations)” so interesting is your entire story, starting from when you were a little kid and leading up to age 30.

Kyle: 11:47 Yeah, so I was raised by my parents as Jehovah’s Witnesses. They converted back in the 70s when they were still young adults themselves in their twenties and so, you know, to me it seemed mostly normal growing up that way. I mea it’s hard to be a Witness kid because there’s a lot of stuff you can’t do. Celebrating birthdays, you know, hanging out with kids at school, like after school, going to their house, participate in sports. It’s a very, very strict upbringing for the most part. But you’re also kind of taught that you’re—it’s of weird, but like your group is the only safe one. Everybody around you, they’re all worldly people and Armageddon is going to come any minute and destroy them all. So you have to try to save as many as you can. So that’s kind of a weird way to grow up. I refer to it as a doomsday cult, which some people think is a bit hyperbole, but I think it’s close to the truth.

Chris: 12:51 Okay. So what that led to though, and you know, this is actually a recurring theme in the book is like not just here’s this, this hard thing that I went through, but also like, here’s how it’s helped me down the road. And I was surprised when you said that you weren’t naturally an outgoing kid because in the book you’re telling stories about, as a kid, knocking on doors to talk about religion. How did that go?

Kyle: 13:13 Well, you know, this is the thing, when you’re raised as a Jehovah’s witness, knocking on doors, preaching is expected, right? You don’t have a choice. So you either have to just figure out how to do it—and I mean this is the thing a lot of people don’t realize, but all Witnesses, when your door is knocked on on Saturday morning, the person on the other end probably doesn’t want to be there any more than you don’t want to have them there. They all think that they’re there, you know, with zeal and vigor or trying to save your soul, and that is a very small amount. The majority are like, “This is what I have to do.” They count their hours and have to submit them at the end of the month. It’s like a sales quota. So you’re praying that the other person doesn’t answer and we can just mark them as not at home and move on to the next one. But then if they do show up at the door, you’re like, “Oh crap, now I have to say something.” And so then you have to go back to your training and use your rehearsed presentation and you know, overcoming objections. And there’s a lot of like kind of overall sales training that you go through as Jehovah’s Witness to be able to create rapport with the other person, try to listen and understand their needs. All sounds a lot like sales training.

Chris: 14:24 So before I get to the sales training and how it’s benefited you, how often were those sales pitches on the porch successful?

Kyle: 14:31 Oh, very, very rarely. Generally the way it goes as a Jehovah’s Witness, when you do the door-to-door, you know, probably 70% of people won’t answer the door or they’re not home. Then of the few that you get probably, you know, 90% will say “not interested,” close the door. A couple will yell at you and then like out of the rest of them, they’ll usually take magazines. That’s kind of like the thing that people do because they think that’s what gets rid of you is they go, “Ok, yep, sure. I’ll take your Watch Tower and read it. Thank you.” But what they don’t realize is you’re inviting them back. As soon as you do that, you’re now a lead. You know, they don’t call them leads, but they’re basically “Oh, I placed some magazines. I’m going to write their name and their house number and now I’m going to come back in a week and try to give them the next set of magazines and then try to develop that into a Bible study, and after a Bible study, I’ll start bringing them to meetings.” It’s a very, very long sales cycle, a very long road to conversion. But actually, at least when I was a kid in the 90s and the Internet wasn’t as prevalent with information, that is how we Witnesses were created other than just being bred and raised in the religion.

Chris: 15:41 OK. So you’ve done an amazing job already of, you know, sharing how that process is a lot like lead generation and cultivation and nurture. So how has that prepared you for what you do today?

Kyle: 15:54 Well, even though overall my experience in that religion and the process of leaving it was an incredibly negative experience, although generally shaped who I am, so can’t discount that. I think that the greatest thing about it was when I was a kid—and unfortunately they don’t have this anymore from what I learned from those inside—is they used to have weekly public speaking training where you would get a talk slip maybe every month. That will be your talk you have to work on you, you do the research, you practice it, and then you go up, you deliver it to the congregation. Usually five minutes and then as you kind of get more experienced, you’d give longer talks and then literally like an adult or an elder or somebody on stage would grade you afterwards in front of the audience. They’d be like, “Well Kyle, that was a really good job on the talk. Noticed that you didn’t pause quite enough. You were kind of rushing a little bit.” They would actually critique your performance onstage in front of everybody. So there was a lot of like lessons I guess on being humble. Like, that was the one of the main things as a Jehovah’s Witness is you have to be humble, you have to basically take it. You have to take any and all kinds of abuse. Now realizing later on why they encourage these traits is you’re much more obedient and willing to follow the rules and not question authority, but I digress a little bit. The public speaking training was very effective and it helped me even today to be able to give presentations, and I think it’s a shame that kids are growing up Jehovah’s Witnesses now don’t have that.

Chris: 17:28 Exactly. Yeah. You know, that’s one thing that’s really missing from our schools, at least in Canada, that you’ll find when your kids are a bit older is there’s no public speaking training at all. And so I think that the best is probably somewhere in the middle. But did those skills directly help you when it came time to raise money for Proposify? What was that process like?

Kyle: 17:48 Yeah, I mean, I think when it came time to raise money, it was probably more so just being in business for quite a few years that helped that. To be perfectly honest, think my business partner is the generally the leading force behind raises, so I can’t take credit. You know, it’s very similar to our relationship at Headspace. When it came to sales, Kevin was much more the opener and I was the closer. Kevin was great at building and nurturing the relationship until it got to a point where, pkay now you have to present the plan or present the contract and then get it signed. And it worked very, very similar to our fundraising efforts where Kevin would develop all the relationships with VCs and different investors and show them our numbers and our pitch decks. But then actually, you know, hopping on a plane and going and pitching it would be us together. We would do that. So the presentation skills for sure probably helped. Although, we haven’t been super successful with raising money as much as others have, so I don’t know how great I am to be able to offer advice there.

Chris: 18:52 That’s okay. I mean, you know, what I guess I was getting to is that your first rounds came from somebody that you’d made a connection with another way. Right? Well maybe just tell us that story to start.

Kyle: 19:03 Oh, that was raising the first round for Proposify? Yeah, I mean when we were running Headspace, there’s a VC group in the city that I’m in, in Halifax, called Innovacorp, and we had actually pitched them on raising a seed round back when we were running Headspace, and they turned us down. Now, a year passed and we had come out with our MVP. He got some traction, he got some feedback, not a lot, but you know, I think we were at maybe 10 customers or something like that, paying 20 bucks a month. So very, very small amount of traction. But we had done it, we’d put something out there. And then we were getting towards the tail end of getting out of the agency business. I signed up one month to a pitch competition at the local kind of start-up group called Volta just to kind of pitch, more or less get out and practice, you know, and at that pitch competition, ended up winning the competition and that same guy from Innovacorp saw what we were doing and was like, “Oh wow, you know, you guys have come a long way and we should definitely talk.” So that was sort of the beginning of just getting in the door with them and then ultimately they said yes when we pitched the board on what we were doing.

Chris: 20:17 You know, there’s really, I think, two valuable lessons there. And the first is that just because someone says no once doesn’t mean it’s a no forever. But you know, the point that I was trying to reach here I guess would be, it never hurts to go out and make more connections. How has that helped you, you know, grow Proposify?

Kyle: 20:33 It’s funny because a lot of our members of our leadership, two in particular that come to mind, Ricky, our head of product and Jen of communications, you know, I have known them for 10 years. We actually met before I even started Headspace at the agency. And so, I mean it’s been a long, long relationship but now they’re members of leadership at Proposify. So I found that as you kind of go about your being in business or being employed somewhere, if that’s where you’re at, is and look at everybody as a potential lifelong connection, you know, people that you really click with and people that work well together. You know, you could be working at their company or they could be working at your company in 20 years. You have no idea. So the more of those relationships you foster and create and also prune, you know, the people that aren’t adding value or you don’t click with or you know, just basically being able to—I don’t actually believe that you have to be friends with everybody and you have to, you know, not burn a bridge; I think sometimes it’s great to burn a bridge, you know, just know who you work well with and enjoy their company and don’t spend time with people who are kind of energy drains on you.

Chris: 21:48 Can you give us an example of somebody that you’ve pruned? Maybe a client, maybe a staff person?

Kyle: 21:54 Yeah, I mean both of those, you know—hard to give out examples with staff. But I mean that happens. You always have the best of intentions when you hire somebody and over the course of time you sort of figure out they’re either not a cultural fit or they just don’t have the skills that you thought that they had and you’ve got to let them go. And that’s always hard. Sometimes you part on good terms and other times, you know, we had an employee who, the relationship was somewhat acrimonious as she left and ended up filing complaints and kind of going the legal route to try to get back at us. So that was unfortunate. But I mean that stuff happens. We always encourage our staff, like if you’ve got a customer who’s just unreasonable, rude, hangs up on you, swears at you, you know, just doesn’t want to—like a relationship in business, it has to be an equal exchange of value. So if you’re providing a service, you’re offering them value but they don’t want to pay you or they don’t want to live up to their end, then it’s not meaningful transaction. So that’s sort of the barometer for just fire them, you know? And you’d be amazed how many times an employee will think that the customer’s always right and you always have to say yes, and the ultimate goal is to keep the client. So when I would say, well, just fire them, just get rid of them. They’re always like, “Really? You can do that?” It’s important.

Chris: 23:19 It is. And you know, you’re a really great connector. So I’m going to bet that, you know, maybe you’ve had a friend who worked for you or a friend who was an early client and then you realize that, you know, while they were maybe a great friend, they were not a good fit for your business. How do you recommend people fire those clients?

Kyle: 23:38 Yeah, when they’re friends. You know, I’ve always been of the mind that you can certainly be going into business with friends and I’ve had pretty good success with it, but the person on the other end cannot look at it as, what’s the word? You know when you just hire your friends and family because they’re friends and family.

Chris: 23:59 Oh, nepotism.

Kyle: 24:00 Nepotism, yeah, like they have to know that okay, we might be friends and we might be able to go play, like Ricky and I play racquetball after work sometimes. You know, we’re very close friends. We were best men at each other’s weddings last year, but there’s still, we have to separate the business side of it. So when he comes to work, he comes at it with all of his energy, wants to be critiqued. You know, like, it’s actually a boss-employee relationship. He’s able to do that. He’s able to separate them. But I think when you hire your friends, you have to be sure that they’re not just looking at you to get them a free pass because we’re buddies.

Chris: 24:36 So how do you—what’s the first conversation when they’re hired, then? I mean, I’ve really struggled with this, so I hope you don’t mind me following this question a little bit more.

Kyle: 24:45 Yeah, the questions you ask. I mean, I think generally for people that I’m friends with, it sort of doesn’t need to be said, although maybe it does. That, you know, we’re entering into a contract here. Like, you know, you have to look at it with the same expectations that you would go into business with anybody, which is you have to live up to your end and I have to live up to my end, you know? And that means that sometimes you’re going to fight, which I actually think it’s great if you’re friends and you can have a good work fight. That’s how you get the best results, you know, you argue you and then oftentimes because they’re your friends, they’re more willing to challenge you, which is a great thing. Sometimes if it’s somebody who it’s like, they just met you, they’re a brand new employee, it takes them a lot of time to feel comfortable with challenging the boss because they’re used to environments where challenging equals getting fired.

Chris: 25:33 Right. That has come up recently, too. But you know, one of the most interesting parts of the book for me was you’re mostly writing about SAS business and software and stuff. But you have some really great advice for service-based businesses, too. And that’s who mostly listens to this podcast. Owners of gyms and hair salons and attorneys. And one of the things that you said in the book was that a service business can be lucrative for the founder if you go narrow and deep. What does that mean?

Kyle: 26:00 Yeah, I mean, you know, before you hit record, we were talking about websites, and I think this is a good lesson for all these different types of businesses, gyms and hair salons, you know, in the web-design business, it’s gotten very, very hard over the last decade because it becomes more and more of a commoditized service. So anybody can go and sign up to Wix or Squarespace or any of these do-it-yourself website builders, use a WordPress theme and it’s generally fairly fast and easy to get a really good-looking website up and running. So the mistake that I made with Headspace was we didn’t see ahead, and we didn’t focus on where the market was going. We kind of buried our head in the sand and just said, nope. It’s just the same thing Blockbuster would’ve done with Netflix, right? Like they bury their head in the sand, “no, people are always going to come to the store and want to rent their DVDs and pay their late fees” and they just refused to accept, you know, the reality of where things were going. And we kind of did the same thing on a smaller scale. You know, you’re going to be able to get a mom and pop to pay you 10k for a website. There are certainly people who will pay 10k and 100k and a million dollars for a website, but they’re probably not a mom and pop. So we didn’t see that coming. Now the way that agencies, the really good ones are able to do it now is they go super narrow and deep.

Kyle: 27:13 So, I use the example in the book of a local agency who kind of was our contemporaries at the time and they’re still running a 100-plus person agency, very successful and profitable. And what they did was they just said we only do travel and tourism websites, we help big brands, big travel brands, increase their bookings online and, and all their marketing, all their sales efforts, a hundred percent focused on big cruise lines and all these types of tourism and travel companies. If you’re the best in the world at something, then people will seek you from outside. They’ll want to work with the best. I like to use the example if you’re need a photographer, if you run an agency and you get the Corvette account and you’re going to do all the advertising for Corvette or for Jaguar or something like that, and you have to hire a photographer to do that, are you going to hire the photographer who does weddings and portraits and food shots? Or are you going to hire the photographer that does luxury cars? That’s all they do. They’re the best at it. Of course, you hire the specialist. For gyms and a hair salon, even though I don’t know a lot about those specific businesses, the same thing can happen on a local level because that’s usually, I think, where those types of businesses are competing, is for local business. Is they can be the best at X niche. Like you, you know a lot about the CrossFit business, right? So that’s, I guess what I mean by going narrow and deep.

Chris: 28:36 So I think a lot of people understand that concept logically. I think what maybe ties them up is this notion that it’s a zero-sum niche that for me to get a new client, I have to take a client away from you, but one of the first things that you said on this podcast was there are other proposal softwares out there now and that’s growing for everybody. So is it a case of just broader awareness that proposal software exists is benefiting everyone or is it something else?

Kyle: 29:05 No, I think that’s a great point. You know, even though there is more competition, you know, obviously that puts pressure on us to be even more focused and even more specific in our messaging because we’re not the proposal software for everyone. For people who, for instance, care a lot about the design of their documents and want total control over the customization of the documents, we can totally compete in that space. Not every piece of proposal software is like that. Some of them, you know, you just upload your word docs and you don’t care if they look good and it’s just all about the automation. For others it’s the simplicity, it’s like super easy to just type in the box, no training required. We can’t compete in that space.

Kyle: 29:43 So just kind of knowing where you fit in that space. But yeah, overall, proposal software, knowledge of it has grown in recent years. I think it’s the same thing with any business. My wife is a subscriber to five different gyms in our hometown. You know, those gyms might look at each other like they’re competition, but maybe you know, for certain customers and they’re just, “Oh, well if I want to do CrossFit on this day, then I’ll be a member of this gym. But you know, when I want to do hot yoga or pilates, I go to this gym.” I don’t know if that person makes sense. I obviously don’t know what I’m talking about.

Chris: 30:15 No, that makes perfect sense. And that’s something that I actually talked about in my first book back in 2012 was that that was where the market was going to go to, that I thought CrossFit was going to be one of five or six choices that made up your entire exercise portrait. So how did you determine where you fit in that niche though, Kyle?

Kyle: 30:35 I think a lot of it is know where you’re strong at already. I think it takes a certain amount of self-awareness both as a person and as a company to go like, what are we already really good at? What are our best clients? Who are our best clients rather. Because if we want to be more specific and have more of a focus as a company, we have to know, who are we all ready making happy? If we’re trying to go after, you know, huge enterprise clients but our best clients that are super profitable are you know, in this 200-employee range. Well, you know, why are we going over here when we’re already serving this group very, very well. And also, maybe because I have a design background, I always wanted a proposal software that was very customizable and you can just brand it to look exactly like your InDesign file. That was important to me and I assumed it would be for other people. Not every customer cares about that. The ones that do would use our software, not someone else’s. So I think it’s just a lot of self-reflection and going, where are we already strong? Let’s double down on that rather than trying to go over here and do something we’re clearly not cut out for.

Chris: 31:43 And how often do you talk to these, you know, these best clients? You know, maybe you’re familiar with Mike Michalowicz’s Pumpkin Plan. So his idea is that you identify your top three to five best clients first by the revenue that they drive and second by how you feel when you’re serving them. You know, do they fill you with energy? And, so you know, if you know who your best clients are and you’re very focused on serving them better, how often are you asking them about how you can improve your service or what you should be working on next?

Kyle: 32:13 Yeah, you know, I used to do it a lot more. I used to have conversations with virtually every single customer who signed up. Of course, companies scale and now we’re at about 8,000 customers. That becomes a lot harder to do. But you know, customer development is a big core part of who we are. So everyone from just having conversations with customers and just reading the conversations they’re having and seeing what customers are saying, listening in on phone calls that salespeople are making, there’s a lot of ways at scale I think to collectively cull information and just know as a group, okay we know we’re doing really well with these franchise groups for instance, but maybe not with companies that need CPQ or all their salespeople are in the field with iPads for instance. We know that if that’s their current reality, they’re probably not going to be super happy with our service. Now maybe that’s an area we can get better. But just kind of knowing where you play by talking to your customers or rather your employees who can talk to your customers.

Kyle: 33:20 Okay man. I think that’s great advice. So last question. What’s your actual role at Proposify now? How do you spend your day?

Kyle: 33:28 You know, I struggled with this I think a couple of years ago and that was what impelled me to reach out to Dan Martell and get his coaching because I didn’t know what I did anymore. I was used to being in the trenches, you know, designing and having customer support conversations and really like doing the work, and transitioning out of that and trying to build a company was a whole area I’d never really known what to do. So I’ve gotten a lot of help from that group that we were a part of, that I’m still a part of. And so, you know, I think the advice that Dan Martell gives us about, like setting the vision and building the team and keeping money in the bank are the three primary roles of a CEO. I try to stay focused on that stuff, and I think that I’m in a really good position where Kevin as a cofounder is really good at the money part. So that’s an area that I’m kind of week in, is like the operational, working with the accountants, kind of knowing where we’re at financially. He owns that. So it really gives me a lot of freedom to focus on vision and team building, which was the stuff that I actually really enjoy, is sitting with the product team or sitting with the head of customer success and just talking about like where are we going? Where’s the product going? Where are the opportunities, where should we be doubling down on? And then running the weekly sync meetings. Yeah, I mean that’s kind of what I do every day.

Chris: 34:49 It’s really cool, man. Well Kyle, you know, my favorite thing about “Free Trials (and Tribulations)” is that, even though there are a lot of hardships that you’ve gone through, it’s really, really obvious how surviving those things has separated you as an amazing entrepreneur and benefited you later in life. So thanks for giving me an hour and thanks for this book.

Kyle: 35:07 Oh, thank you Chris. A lot of fun.

Chris: 35:10 Hey everyone. Chris Cooper here; I’m really thrilled to see you this year in June in Chicago at the 2019 Two-Brain Summit. Every year we have two separate speaking tracks. There’s one for you, the business owner and there’s one for coaches that will help them make better, longer, more meaningful careers under the umbrella of your business. This year we’ve got some pretty amazing topics like the client success manager, how to change your life, organizational culture or the business owner’s life cycle, how to have breaks, how to have vacations, how to help your marriage survive, owning a business, motivation and leadership, how to convert more clients, how to create a GM position that runs your gym for you and leaves you free to grow your business, how to start a business owners group in your community and more.

Chris: 36:02 Point here is to do the right thing that will help gym owners create better businesses that will last them for the long term, get them to Tinker Phase, help them be more successful, create meaningful careers with their coaches and give their clients a meaningful path to long-term health. We only do one big seminar every year and that’s the Two-Brain Summit and the reason that we do that is because a big part of the benefit is getting the Two-Brain community together and welcoming strangers into our midst and showing them how amazing gym ownership really can be. We’ll have a link to the Two-Brain Summit, including a full list of all speakers and topics on both the owners and the coaches side in the show notes. I really hope to see you there.

Greg: 36:38 As always, thank you so much for listening to this podcast. We greatly appreciate you and everyone that has subscribed to us. If you haven’t done that, please make sure you do. Drop a like to the episode. Share with a friend, and if you haven’t already, please write us a review and rate us on how what you think. If you hated it, let us know. If you loved it, even better. See you guys later.

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