Episode 1

Clate Mask | CEO and founder | Infusionsoft

Rebranding and Entrepreneurship Challenges with Infusionsoft Founder, Clate Mask

On this premiere episode of the Catalyst Podcast, LeadMD CEO, Justin Gray, welcomes Clate Mask to the show. As CEO and founder of Infusionsoft, Clate’s experience ranges from managing a services business to making the leap to software and a rebrand of the 15-year-old brand to Keap. In this interview, it isn’t just about business, but also how the strain of running a business impacted his personal relationships. A lot of tips in this one for business and personal life.

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Time Stamped Show Notes:

1:00 – Who are you? Tell us a little bit about Keap (previously Infusionsoft)!

03:21 – Do you have one monumental moment of cataclysm?

06:27 – Who was the voice of this catalyst moment?

08:21 – What is your answer to those who question your mission?

16:11 – Was it your intentional goal to inspire that same catalytic moment in other entrepreneurs?

18:07 – What characteristics do you look for in individuals as you grow your teams at Keap (previously Infusionsoft)?

20:05 – What are some traits you often see in small business owners?

22:20 – What are your thoughts as you look back on how far you have come?

24:20 – Wrap Up

3 Key Points:

  1. The support of others is crucial. No one said entrepreneurship was going to be easy. Colleagues and loved ones who have your back help to make those hard days a little bit better.
  2. Strive to understand your customers obstacles and how to help overcome them. Standing in your customers shoes and connecting with them on a personal level will help to build lasting relationships and overall, improve your business.
  3. The “Keep Going” mindset is very important. After you reach a certain level of success, challenges don’t cease, they simply change. It is important to remember those moments that brought you to where you are today.

Our favorite quote from the episode:

“I wouldn’t be doing our listeners service if I said, “Yeah, it’s just great that we stuck with it, and now everything’s been wonderful.” No, there are times where it’s amazing and we feel like, “Wow, so glad we did that.” And there are times where it’s, “Whoa, this is really challenging.” These are bigger challenges sometimes that we felt in those very earlier days. But you relish the challenges and you get more and more confidence as you beat those challenges over time. And you look at the challenges as obstacles, and things that just come with the territory in entrepreneurship.”

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Full Transcript

Justin: Hey, hello and welcome. You are back on catalyst, and we’ve got another great guest lined up here today. I’m thrilled to be joining Clate Masks. Clate is the CEO and founder of Keap. And if you’re not familiar with Keap, it might just be because of the recent rebrand. I’m sure you’ve heard of Infusionsoft, formerly known as Infusionsoft. The new brand is now Keap. So let’s talk through about that in the road to this recent transition. So Clate, welcome to the show.

Clate: Justin, great to be here. Thanks for having me.

Who are you? Tell us a little about Keap!

Justin:  Absolutely. So let’s do a little bit of background here as we get started. Just kind of fill the listeners in on who you are? A little bit about Keap, and then kind of what a normal day looks like for you over there.

Clate: Yeah, you bet. So I’m co-founder, and CEO. We started Infusionsoft shoot 17 years ago. And for the first few years we were just small business, just helping small businesses grow, automating their sales and marketing. And then we created our first product. And for over a decade Infusionsoft has been the leading sales, and marketing automation software for small businesses. A couple of years ago, we decided you know what? We need to go beyond Infusionsoft, and really open up the market to serve small businesses that maybe aren’t ready for all of that sophistication and power. But want an easier lighter solution that gets them some of the same benefits. A nd so we began creating a new product and that of course, led to the creation of the Keap product, and the rebranding of the company as Keap.

Justin: And so, how long was that transformation? How long did you have Keap under development?

Clate: A couple of years. At the beginning of 2017, is when we decided we were going to create this version of the software that would be the thing that we could use to serve millions of small businesses. And it really became because at the end 2016, we reached the end of a 10 year mission, and we decided, okay, what’s next? And we created the new mission that goes through the year 2030. And that mission is to simplify growth for millions of small businesses worldwide. And we recognize that in order to do that, we needed to create the easier, lighter version of our software, and have a platform that we could take to small businesses to help them grow with an addition of the software for whatever stage of growth they were in.

Do you have one big moment of catalyst?

Justin: So I think the most astounding thing here is 17 years, right? Like we have a lot of folks on the show, and they’re talking about, four, five, six year runs. And that seems to be like a long history. 17 years isn’t an enormous amount in SaaS technology. So, if I can’t ask you, let’s rewind all the way back to the beginning, or maybe just along that journey. Because the entire show is really about, those moments of change, those moments of impact, things where we doubled down as either entrepreneurs, or executives, business leaders. And I know that you’ve got those moments throughout your journey here. So do you have one big moment of catalyst? Or have there been many along that extensive journey?

Clate: There’s definitely been many along the way. I think one big one was, early on and when we began to make this shift from being a service provider that was trading hours for dollars, doing custom software to becoming a product provider, and having a SaaS solution that we could help small businesses grow with. I think that transition from services to product, and specifically to a SaaS product. That was a big change, and that required a lot of courage to burn the ships on one side, and decide, okay, we’re going to go for it. And we didn’t have a good financial cushion to fall back on. We didn’t have a really well vetted, perfectly articulated business plan. We just had a pretty strong sense of where the market opportunity was, and a recognition that our service business, and specifically the hours for dollars game that we were in, that that was holding us back from really getting to the market that we wanted to serve with our product. And so that was the basis for us deciding, okay, let’s go for it, and let’s create this product that we can serve small business marketers with.

Justin: And did you have complete alignment within the organization around that change? Or were there folks that took convincing? Did you take convincing?

Clate: It’s funny because we were a small group at the time. There were just five, probably seven of us, and I was probably the one that required the most convincing because I was the person responsible for sales, marketing, customer success, paying the bills. The rest of the team was doing software development for customers, and a little bit of tech support, and customer success. So I was kind of more sales marketing, account management, and then doing the books, and making sure that we could keep the lights on. So when I looked at the question of abandoning that part of the business, or at least stepping away from it, and really going after more aggressively the product that we had been working on and wanted to create. That was a scary proposition, and it wasn’t something we could easily just say, okay, let’s go for it here. So we did it thoughtfully, we took measured risk as entrepreneurs will do. And then there was a point where we had to hold our breath, and just charge forward as hard as we could.

Who was the voice of this catalyst moment?

Justin: Sure. So I find that kind of that ability push through, or even to view risk in a very unique way as entrepreneurs normally do, like those are normally traits that are supported by either mentors within an individual’s life, or just a really strong influence and presence. And I’m curious, is there that type of individual that you cite in your own personal path, career path that you would look back on, and say, “Wow, this individual is really someone that armed me with what I needed to go out there and succeed?”

Clate: There’s so many, it’s hard to say one but yes, I definitely, I mean, I’m entrepreneurial. I wanted to go for it, but I also have a certain amount of managing things, and making sure we can cover the bases and my co-founders, Scott is probably the best in terms of like, look, we’ve got to go after this. He pushes on the vision, and the belief of what we can accomplish. Which is great and certainly did that in this early decision we made.

In that early decision, he was the key catalyst that pressed us and said, “We need to do this.” And I knew it in my heart, and in my gut, but my mind didn’t want to go there. My mind was more conservative, and saying, “Hey, we’ve got to play it safe here a little bit, and make sure that we’re covering our bases, and able to pay our bills and make payroll.” And that sort of thing. Even though my heart, and my gut had the sense of, yes, the opportunities here, let’s go for it. And I wanted to, but those were the debates we had together as a founding team. There were three of us at that time, and Scott my co-founder was definitely the voice as a catalyst to help us move forward.

What is your answer to those questioning your mission?

Justin: And so I’ve also heard some stories, after you guys made that transition, and you were going full bore at the SaaS space, that there was also some interesting conversation that took place between you and your wife about traction within the business. And ultimately maybe some doubt that was interjected there as well. So I’d love just to kind of get that context because quite frankly, it’s something that we don’t talk about a lot, which is when do you say when? And what do you say when folks in your life that are really important to you are also questioning that mission?

Clate: Yeah. Well it took us about a year to get to the point where we said, okay, this we’re going to really go at the market with this SaaS CRM product. And then it took us another two years, I would say, to get to the point where things were going pretty well, and we were able to pay ourselves consistently reasonable salary. But for those first three years, it was really, really tough. And so, to give you a little bit of context, I’d done eight years of college. My wife, and I both had degrees, and we had a lot of student debt to show for it. We had four kids at home. My wife Shariece is as a working like crazy, taking care of the kids while I’m working like crazy, trying to get this business off the ground.

And it was great to get to the product decision, and we started to get a little bit of traction there, but it was nothing close to being able to provide a reasonable income for the three of us as co-founders. And we didn’t have any other funding sources or anything like that. It was all bootstrapped, credit cards, I mean, doing everything we could to survive. So you can imagine that as the months went by, and we were struggling and getting deeper and deeper into debt, and creditors are pounding on our door both personally, and at the business, my Shariece is saying, what are we doing here? How long it’s going to work? and is this really the reason we went to eight years of college? And so I continued, I had gotten to a point about a year, and a half into our business where we had our product, and we were seeing our customers using it, and we were seeing that it was valuable for them to do these automated marketing campaigns in their small business, but it wasn’t yet translating to solid revenue for our business.

And it certainly wasn’t yet translating to take home pay for me and my wife, and my partners, and their families. So one night she just said, we were about probably two and a half years in, and she said, I just can’t do it anymore. And I had lots of conversations trying to persuade her, and she said, you’ve got to do something different. You got to promise me this time that, and that you’re going to look for a job. And I had said before, okay, I’ll start kind of keeping my eyes open, and that sort of thing, and be open to other possibilities. When the reality was my heart, and mind were so much into the business because I was seeing at work, and I really felt like it was only a matter of time before we started to really have some success that she could measure in terms of a bank account, and deposits that sort of thing.

So I was trying to hang on because I believed in it at that point. I had gone through my dark period where I wasn’t sure by the way, but at this point I totally believe we were going to do it. And our customers feedback was giving us the right indications. She wasn’t there, and she was definitely doubting. And so she said, look, “you got to promise me that when you go into the office tomorrow you’ll look for a job,” and I said, “Okay.” And this was a tear filled conversation. This wasn’t just nice. Right. We got lots of these, and I had prevailed in persuading her to stick with it many times before, but this time I wasn’t going to prevail. And she said, like, “you have to go look for something.” So I said, all right.

And so, the next day I went into the office, and I sat at my computer, and started working, and before I knew it, the day was over, and I hadn’t done a bit of job searching. That the business had just swallowed me whole that day. Like it had done so many times before and like it does for so many entrepreneurs, and I was busy working leads, and talking to customers, and all of that. So I basically drove home that day, both bugged with myself, that I hadn’t done what I said I would do, and very nervous about what it would mean for my relationship with Shariece. Who by the way, just to be clear, I mean, she’s a total saint, super supportive, very much in my corner, but she had gotten to a point where she was at the end of her rope.

That Day I walked into the house, I remember it very, very well, never forget it. Walked in, her back was to me, and she turned around and said, “Did you look for a job today?” And I said, “No.” She walked towards me, she gave me a huge hug, and she said, “Just keep going, it’s going be okay. Everything’s going to work out, just keep going.” And that was an amazing moment for both of us, any entrepreneur who’s experienced the challenges where you, and your loved ones are drifting apart because the business is requiring everything that you’ve got, and your relationships are suffering, and you’re struggling, it’s a really tough place to be, and I’ve talked to so many entrepreneurs who have been in this place.

So when I got to that point, and she was able to support me and say, “We can do this, keep going.” That changed everything, and it really was… I mean that was, you talk about a catalyzing moment, that was probably the most clear catalyzing moment I’ve ever had because it just … When you and your partner are in that place where now you really are working together, and you’re not pulling apart from each other anymore, it does something incredible. I mean rocky screams, “Yo Adrian!” Because it’s a very catalyzing thing to have happened between the husband and wife, partners that are working on a business

Justin: That’s an awesome story, and it also reminds me a lot, I took a look at Keap’s new commercial. I know there’s a couple of different versions of it, but you might think I saw the long version. It feels incredibly similar to the experience that you guys are describing in those commercials.

Clate:  Yeah. Yeah, it is. I mean, the reason we chose the name Keap, is because the challenge for business owners who have that overwhelming desire to quit at times and frankly who romanticized the idea of quitting because it just gets so hard. As you know our brand of Infusion Soft has always been about small business success, and we’ve always been about encouraging the business owner to keep going, to grow their business, to make it work. So our message to small businesses everywhere is keep going, keep serving, because we’ve serve service businesses and keep growing.

We’ll build back Keap brand, we spell it K-E-A-P, so we can own it and trademark it and all of that, but it’s all about that very common word in our vocabulary, that means a lot to the success of a small business. It’s really the essence of what the Infusionsoft brand was, and now we’ve brought it front and center under the Keap brand.

Was it your intentional goal to inspire that same catalytic moment within other entrepreneurs?

Justin: Yeah. So if you guys haven’t seen the commercial, we’ll link it here in the comments, but essentially it’s exactly as Clate is describing it there. It’s about the doubt that really creeps in within entrepreneurs, within small business owners about the ability to run a business like that. I think a lot of folks have that drive or that craft around a certain thing, whatever that is, but then there’s the whole business aspect that surrounds that. How important is… It seems very formulaic now that we’re laying it out and still but was this an intentional goal of yours with the past that you’ve gone through for 17 years of building Infusion Soft to now Keap, to inspire that same catalytic moment within the entrepreneurs?

Clate: Absolutely. Our brand is a very inspiring brand, it’s always been that way. When we looked at, okay, how do we take this message to the world for millions of small businesses? And how do we help millions of customers simplify the growth of their business? We wanted to make sure that we preserved the essence of the brand, and one of the things that I’m so proud of in the branding work we did, which is it’s never an easy thing to rename your company and put new branding, but we did it because we have this vision to simplify growth for millions. In doing so, we wanted to make sure that we preserved the essence of our brand that we’ve always had.

That is very much an inspirational brand and message and feeling for entrepreneurs that are in those challenging moments, it’s also very much about growth. We are the growth platform for small businesses, that’s what Keap is. Our message is not just an inspirational keep going in the tough times, but keep serving, because as you serve your customers, everybody benefits and then keep growing, which really the big message of our mission is to grow your business.

Justin: That’s a great foundation in terms of your own catalytic moments in growing the business, and certainly overcoming those moments of doubt, incredibly difficult to do. Then you have to go build an organization that is going to have that same drive and the same desire to win and succeed. Number one, how many employees does Keap have at this point?

Clate: We’ve got about 450.

Justin: So a lot of folks involved there?

Clate: Yep.

What characteristics do you look for in individuals as you grow your teams at Keap?

Justin: What do you look for as you’re growing and scaling those teams, so that you… Hopefully people are inspiring others around them, and they’re fulfilling on this vision that you set out there?

Clate: Yeah. Well, it’s a great question, you need people who are scrappy and think like small business startup mentality, but you also need people who can build system and processes that can scale and serve millions. So it’s a tricky thing, and obviously you tend to blend across the spectrum. But in terms of people who are making things happen, we want people who are very passionate about small business success. So we look first and foremost for people who align with our purpose. Our purpose is to help small businesses succeed, our mission is to simplify growth for millions of small businesses. So we have to bring in people into the company who are aligned to the purpose and the mission that we have, and then who embrace the values that we have.

So when we hire or make a decision to part with somebody, or when we see somebody who’s not performing very well, we need to coach them up. We’re doing that, not just in terms of the skills of their role, but more importantly we’re doing it in terms of the purpose, the values and the mission of our company. That’s critical, when we do that well, we have people who make things happen who are great catalyst for growth, not only in our customer’s business, but also in our business.

Justin: Do you find that a lot of those folks that ended up being that ideal employee profile have owned a business in the past, or have some experience as an entrepreneur?

Clate: Yeah, many times they have, we’ve got a lot of employees who’ve owned their own business, many who still have something on the side, and we’re okay with that, we allow them to do that because it keeps them better connected to our customers and understanding what it is to grow a small business.

Justin: So I understand that you guys did a ton of market research as well in conjunction with this campaign.

Clate: Yeah.

What are some traits you often see in small business owners?

Justin: What did you find out about the small business owner essentially? What are some of those traits?

Clate: Well, they definitely have this rugged individualism in them where they want to go do their thing, and a certain amount of nonconformist and things we understand. I think everybody knows I’m not breaking news here on in that sense. But I think what we also saw was, they feel very lonely. They feel very much isolated. They feel that their challenges, and their story isn’t frequently told that instead there’s an optimism that business owners typically have. And they were that optimism. I’m on their sleeve, but inside there’s doubts, there’s concerns, there’s worries, and there’s kind of a dark side of business ownership that they deal with. So those are just some of the things that we uncovered as we did the research.

I think Justin, the other thing was as we looked at the research, and the whole reason for doing the research was to understand small businesses, and our customers better so that we could serve them more effectively. And I think doing work, that research, not only helped us to get to know who they are, but it also got us to see what they deal with, and the high demands that their customers place on them and what they have to do to better serve those customers. And so the research project became a great catalyst for us in terms of the product work, and the innovation we were doing in our key product to make it possible to serve millions so that our customers could serve their customers better.

What are your thoughts as you look back on how far you have come?

Justin: Yeah, I mean, again, it’s just that daisy chain of moments essentially, right? Like, do I start my own business? Do I keep going? Do I change the product to fit the market? And then just those little explosions that keep a business fresh and exciting, and obviously, accelerating. So that’s great because we kind of wrap things up. I would love to hear the sentiment now as it exists between you and your wife and you look back on this and say like, yeah, we did a really awesome thing together. I can’t imagine that you would.

Clate: Absolutely. I mean, so there’s two answers to the question then the first answer is, we have had … Yes, she absolutely is glad that we stuck with it, kept going and there have been many, many conversations over the years where, wow, what if we wouldn’t have continued, what if we would’ve pulled the ripcord. And so we’re both very grateful for that. I think the other part though is, there’s not … I’m a huge advocate for this position that there’s always tough things, You always have to apply the keep going message. And a lot of times entrepreneurs think, well, I’m going to get to this certain point, and then things are going to be great. And it’s a fallacy. It’s not real. There are seasons where things are better, things are more challenging.

But I’ve come to realize that whether you’ve got one employee, or a million employees, you’ve got different challenges, and you’ve got to stick with it. You’ve got to keep going, you got to be mentally tough. You have to work through the challenges that come your way with excitement, and enthusiasm. Face those challenges with grit and optimism, and knowing that you’re going to work through them. But, I wouldn’t be doing our listeners service if I said, “Yeah, it’s just great that we stuck with it, and now everything’s been wonderful.” No, there are times where it’s amazing, and we feel like, “wow, so glad we did that.” And there are times where it’s, “Whoa, this is really challenging.” These are bigger challenges sometimes that we felt in those very earlier day. But you relish the challenges, and you get more and more confidence as you beat those challenges over time. And you look at the challenges as obstacles, and things that just come with the territory in entrepreneurship.


Justin: Yeah, that’s an awesome message, and a great reminder as well. Like what’s success? The stakes are larger, and so you really do have to keep a good mentality around what success looks like, and know that everything is like. Clate. Again, I really enjoyed the conversation. Thanks for being with us here today, Clate Mask, CEO, Co-founder of Infusionsoft now Keap, definitely check them out, check out the commercial. I think it really kind of catalyzes what we’ve been talking about here today as well. Cleat really appreciate it. Thank you so much.

Clate: You bet. Thanks Justin and I appreciate the opportunity to talk with you about catalyst, and tell a little bit of the Keap story, and we love helping small business grow, and grateful for the opportunity to spend all the time talking with you about it.

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