Keep Going: Sifu Edward & Sifu Julliana Armstrong Sit Down With Keap CEO Clate Mask
Adapted from the recorded conversation; the guest's words are verbatim. The questions are reconstructed and voiced by Sifu Edward and Sifu Julliana Armstrong.
🎥 Video podcast coming soon. The complete interview will play here once published. The full conversation is transcribed below, and the audio edition will be available on sifuarmstrong.tv.
In a new Sifu Armstrong interview, the Keap co-founder argues that entrepreneurship is supposed to deliver freedom, and that most founders accidentally build a cage instead.
Entrepreneurship is supposed to deliver freedom, but for too many small-business owners, it delivers the opposite. That’s the core argument from Clate Mask, CEO and co-founder of Keap (formerly Infusionsoft), who joined Sifu Edward and Sifu Julliana Armstrong for the latest Warrior Intelligence Series conversation.
Mask, co-author of the New York Times bestseller Conquer the Chaos, said he named his company Keap (spelled with an A) around a message aimed squarely at exhausted business owners who want to quit. “Our message has always been to these entrepreneurial, small businesses: keep going, keep serving, keep growing,” he said.
The company’s founding insight, he said, is that most small businesses lose ground not from a lack of leads but from leads that quietly slip away unnoticed. “Prospects slip through the cracks because they’re not hot today,” Mask said. “Virtually every business owner does a good job talking to the lead that’s ready to buy today. But most aren’t.”
As a father of six running a growing company, Mask said the real discipline isn’t balance. It’s priority. “When I say yes to one thing, I’m saying no to somebody that I love,” he said. That calculus, he added, extends to a deeper distinction he sees in the small-business world at large. “There’s a very big difference between having a business and being an entrepreneur,” Mask said, “and I think that that difference is very much the difference between success and failure.”
Mask credited a rotating cast of mentors for his own growth: including, notably, a monthly coaching session he set up with his own parents. “I’d really like to get a little coaching from you,” he told them years ago, and the sessions have continued ever since.
It’s a philosophy that echoes the warrior’s path the Armstrongs teach: don’t let the thing you built start owning you, and never let someone slip away simply because they weren’t ready yet.
In This Conversation
- Why Keap is named around “keep going, keep serving, keep growing”
- The lifecycle-marketing method: collect leads, convert clients, create fans
- “When I say yes to one thing, I’m saying no to somebody I love”
- Having a business versus being an entrepreneur
- Getting monthly coaching, from his own parents
- Where to learn about lifecycle marketing at keap.com
The Full Conversation
Sifu Edward Armstrong: Every operator who tries to build an academy hits the same wall: the warriors who reached out and slipped away because nobody followed up. You can't grow a movement on the prospects you happened to catch on a good day. So when I found the man who built one of the most important pieces of software for exactly this problem (making sure no one falls through the cracks), I knew our Academy Commanders needed to hear him.
Sifu Julliana Armstrong: And there's a deeper reason I love this one. He named his company Keap (spelled with an A), because his whole message to exhausted entrepreneurs who want to quit is keep going, keep serving, keep growing. That is the warrior's creed almost word for word. The tools matter, but that spirit is why this conversation belongs on our platform.
Our guest is Clate Mask, CEO and co-founder of Keap, formerly Infusionsoft, and co-author of the New York Times bestseller Conquer the Chaos. Clate, welcome.
Clate Mask: Thanks so much. Great to be with you.
Sifu Edward Armstrong: For anyone who doesn't know Keap, tell us what it is, what inspired it, and how it grew from Infusionsoft into what it is today.
Clate Mask: Yeah, the simplest way to say it is that it's sales and marketing automation software for entrepreneurs. Entrepreneurial small businesses, they're busy, they're wearing so many different hats. They're trying to get all kinds of different things done and it's really tough to not drop the ball with prospects and customers. So you need a system to help you follow up effectively. You need a system to help you to nurture leads, turn them into clients, turn those clients into raving fans and that's what our software does. It's an automation platform for small businesses.
A lot of people will refer to it as a CRM. Sometimes we'll talk to entrepreneurs and small businesses and they're like, "I don't know what CRM ... I can't even spell CRM." So, we definitely refer to it as customer relationship management software, CRM for entrepreneurs, but simply put, it helps you to do a better job with your sales, marketing and customer service.
We were helping small businesses do their sales and marketing online more effectively. This was 18 years ago. What we found was that there was so much disorganisation and chaos that made it really difficult for our customers to follow up effectively. So we created an automated way to send the right message to the right person, at the right time to build relationship, to do it efficiently and put more hours in the day for the entrepreneur.
So for years, Infusionsoft was this powerful sales and marketing automation software, but we heard customers say, "Oh, I need something lighter." So Keap is the lighter, easier version of Infusionsoft and the reason why we renamed the company is that most customers will start there and we want our software to be known first and foremost for ease of use. That's not what Infusionsoft was known for. Infusionsoft was known for all the power, all the bells and whistles. So today you can buy a number of different products from Keap. You can buy our Grow product, which is for the earlier beginners and then you can buy the Pro product for people that are starting to move up a little bit, and then you can buy our Infusionsoft product, which has all the bells and whistles.
Sifu Julliana Armstrong: I love that it took you three years to get it right, and that you weren't even using the automation yourselves at first. That's the unglamorous part of mastery nobody photographs. But the part that stops me is the name. Tell us why you called it Keap.
Clate Mask: That's exactly right. It took us about three years in the early days to get it right. We began using it ourselves and when we started to see our customers use this personalised, automated follow-up, we saw what a game changer it was. The funny thing is we weren't using the automation aspects ourselves. We were using it to organise our contacts and follow different calling lists, but it was really manual and it wasn't until we started to see our customers using the automation, that we said, "Hey, you know what? We ought to use that ourselves." Once we started using it ourselves, it completely changed the game.
The reason we named it Keap is that for those who know Infusionsoft, you know that we've always been about empowering the entrepreneur and encouraging that entrepreneurial spirit. The reality is sometimes it's really tough and you just want to quit. Our message has always been to these entrepreneurial, small businesses, keep going, keep serving, keep growing and we call it Keap. We spell it with an A so that we can own it. We have a mission that takes us through the year 2030, and our mission is to simplify growth for millions of small businesses and we'll continue that encouraging entrepreneurial spirit to keep going.
Sifu Julliana Armstrong: "Keep going, keep serving, keep growing."
Sifu Edward Armstrong: That's the warrior's path in three verbs. Half of mastery is just refusing to quit on the night you most want to.
Sifu Julliana Armstrong: Every competitor has the moment where the smart, comfortable choice is to walk away, and the ones who become champions are simply the ones who keep going one more time than they fell. To brand a whole company around that is beautiful.
Sifu Edward Armstrong: And it leads right into your book, Clate. Conquer the Chaos, and the idea that entrepreneurship is supposed to bring freedom but so often brings the opposite. That hit close to home for me when I left a franchise that owned my life. Talk about that.
Clate Mask: Yeah, you bet. So it's been about a decade since we wrote it. As we were helping our customers, we saw these common challenges that were causing small businesses to not grow and entrepreneurs to be frustrated and not able to find the freedom they were looking for when they started their business in the first place. See, that's the thing about entrepreneurship is we get into it because we want to have freedom. We want to have impact. We want to have the control to earn what we're capable of earning. The reality is when you get into the business, a lot of times you don't have freedom. You have captivity, the business controls you and owns you and dominates your life.
So as we saw this problem, we began to see very common patterns in what caused it, and we also saw very common patterns among those who were successful in finding the solution. We had a bunch of friends and family and people we cared about who were asking us for all sorts of advice. We said, "You know, we just need to write this." So we wrote a book all about the entrepreneurial mindset and the systems and strategies that are needed in order to conquer the chaos and grow a successful business.
Sifu Julliana Armstrong: "The business owns you and dominates your life." That's the exact trap we warn our Operator-Builders about; the dojo is supposed to free you, not jail you. You're a father of six leading a company. How on earth do you fit it all in?
Clate Mask: It's a great question. I've got six kids and I'm busy with church responsibilities and leading a company. So it can definitely be challenging, but I've learned that there's no balance without priority and so you have to understand priority. I've learned that when I say yes to one thing, I'm saying no to somebody that I love. So I'm very careful about saying yes and that's, by the way, really hard, because I want to help more entrepreneurs. I get asked to be a mentor or an advisor and I have a desire to do those things. But the challenge is when you say yes to one thing, you really are saying no to another. At the end of the day, there's so much time you have, and you've got to make sure that your prioritisation is right and you say no a lot.
So those are a couple of things I've learned and then I just have a whole bunch of little life hacks that I use, things like leaving my phone in the car when I get home for a few hours until I can get the kids down and have a little bit of time to come back to work. I do things like taking kids on trips to kill two birds with one stone, different ways of a rhythm that I have of making sure my wife and I are staying connected. So lots of different hacks. I've made it a life study to figure out how can you have balance and be an entrepreneur.
A lot of people will say, "Oh, there's no such thing as work life balance. It's more about harmony." Leave aside the semantics of it, there is a way to have both and it just requires a lot of intentionality as an entrepreneur. It's tough because entrepreneurship is enveloping, it can be all consuming and we love it and you lean into it. But if you're not careful, your relationships, your health, the things that matter most can really suffer.
Sifu Edward Armstrong: "When I say yes to one thing, I'm saying no to somebody I love," that belongs on the wall next to Donna Kennedy's whole-life check-in and Tom Beal's Trinity. The wise ones all guard their time like a treasure. Tell us about where you come from, your family, and how much you credit to luck.
Clate Mask: I am from an entrepreneurial family. My dad's a teacher. My mom stayed home and raised six kids until my youngest brother started going to school. Then she started an interior design business and just built it from the ground up. She was very entrepreneurial and most of my brothers and sisters are doing very entrepreneurial things. I come from a family of six and I think all but one or two are running their own businesses.
There's definitely luck. I have a lot of faith and so I tend to see it as blessing and divine providence more than just dumb luck, but there's no doubt that, let's put it this way, for all our best efforts, we can't control the outcomes as much as we'd like to think.
In business, we have a few people who have mentored us over the years. Certainly Michael Gerber in terms of small business. In terms of marketing, Dan Kennedy, Bill Glazer, and our very first customers, a guy named Reed Hoisington, just really good direct response marketers. Then in terms of building great companies, we're big followers of Jim Collins. We've had an opportunity to spend time with him. I'd also throw a Patrick Lencioni in there, his work is incredible. Then just on a more personal level, my parents. I've got great parents who have a capacity to love and to inspire and build people up and I'm one of the beneficiaries of that.
Sifu Edward Armstrong: Dan Kennedy and Bill Glazer, those exact names came up when we sat with Craig Simpson, who trained under them. The lineage of these direct-response masters runs through everyone who builds well. And I love that you see providence over luck; I lead from the same place. You mentioned your parents. Do they still advise you?
Clate Mask: It's funny you ask that. I'm a big believer in coaching, and I went to them a few years ago and said, "Hey, I'd like to just do a little coaching session with the two of you and receive coaching from you." I pay a really high price coach to help me out. Over the years I've met with him once a week or once a month, and I went to my parents and said, "I'd really like to get a little coaching from you." So we started meeting once a month, we still do that. That session is all about getting a little bit of business and life advice.
And absolutely, there's a lot of leadership required when you have a big family, four of them are now married and two have a child of their own. So our family is getting bigger and bigger and I'm leading an organisation there too. Though I've got to be clear, my wife is the day to day leader and does an amazing job.
Sifu Edward Armstrong: A CEO humble enough to be coached by his own parents. That's the mark of a lifelong student, which is the only kind of master worth following. Let's talk mission. What's your ultimate goal for Keap, and how does it tackle that brutal small-business failure rate?
Clate Mask: For Keap, I think the small business failure rate is astounding. I think that there's a very big difference between having a business and being an entrepreneur. I think that that difference is very much the difference between success and failure. So my life's work in business is about helping small businesses become great entrepreneurs and helping people to be successful because they are willing to roll up their sleeves and do the work, and they understand what work they need to do. What we do here is we empower and liberate entrepreneurs from the frustrations and struggles that unfortunately, a lot of times, cause them to quit the business.
So we have a big mission to simplify growth for five million small businesses by the year 2030. That's all about an entrepreneurial movement and helping business owners become great entrepreneurs and teaching them the principles and giving them the software to put it all into practise. It's something that isn't going to be accomplished in six months or a year. We've been up to it for 18 years and we'll be up to it for at least another 10.
We teach a methodology called lifecycle marketing. It's really just a way for entrepreneurs to get their brain wrapped around their business and to understand that there are these three phases of the customer life cycle. You have collecting leads and then converting them to clients and then creating fans out of those clients. Business can sometimes feel so dizzying and frustrating, but it's really as simple as that. Collecting leads, converting clients and creating fans. Then underneath that, there's three sub steps of each one and we teach that customer life cycle and then we give you a system to automate it.
When you do that, all of the techniques and shiny objects and different things you pursue as an entrepreneur get settled into place and you can put them into a system to help you run your business. The outcome is not just that you get more leads and more clients and more fans, but you get peace of mind and you're able to conquer the chaos, as we say in the book, and you're able to have a great business and a great life.
Sifu Julliana Armstrong: Collect, convert, create fans. That's the warrior's journey too: the curious visitor becomes a student, the student becomes a warrior, the warrior becomes a lifelong member of the tribe. But the heartbreak you named is the prospect who slips through the cracks, and that one's personal for me, because the future warrior is almost never ready on the first day they reach out.
Clate Mask: Yeah. You nailed it there. One of the main problems that causes small businesses to not grow like they should is prospects slip through the cracks and they slip through the cracks because they're not hot today. Virtually every business owner does a good job talking to the lead that's ready to buy today. But most aren't. Most are interested, but the time's not right and they must be nurtured. Well, business owners don't have time to do that nurturing, which is why it doesn't happen. They've also told us over the years, "I don't have any system or process for doing that." They've also told us, "I'm not sure exactly what to do there. What to say, when to say it."
So Keap is a platform that enables them to nurture those prospects but get them to the point that you can convert them to clients and then turn those clients into lifelong raving fans, but all along that customer lifecycle are pitfalls where valuable prospects and customers slip through the cracks. It can be a prospect that gives you a business card, or you see at an event at the very beginning of your interaction, or it can be actually a customer that has bought from you repeatedly but doesn't realise that you also offer A and B and they go to a competitor to buy A and B because you haven't nurtured that relationship. That's what customer relationship management is. You manage the customer lifecycle and build that relationship, so that opportunities don't slip through the cracks.
Sifu Edward Armstrong: The warrior-in-waiting who wasn't ready the day they first watched a class. That's the person we most refuse to lose. Clate, for anyone who wants to learn more about Keap and lifecycle marketing, where should they go?
Clate Mask: Yeah. We have a lot of learning resources on our site, keap.com, K-E-A-P.com. There's all kinds of things from blogs to reports and all sorts of resources that you can get there. You can learn more about lifecycle marketing there and how to think about your business holistically. Whether you use our software or another solution, we really are just trying to teach the world about lifecycle marketing, because it really does help the entrepreneur conquer the chaos that's going on in their mind and gives them a framework for how to successfully grow their business and not lose their sanity in the process.
Sifu Edward Armstrong: Clate, it's been an absolute pleasure. Thank you for your time today.
Clate Mask: Thank you so much. Great talking with you.
Sifu Julliana's closing word: Keep going, keep serving, keep growing, Clate built a company around that, and it's the creed of every warrior who ever wanted to quit and didn't. The other thing I'm taking is "when I say yes to one thing, I'm saying no to someone I love." A champion's calendar is a series of brave no's. Guard your time, protect the people who matter, and refuse to let the thing you built start owning you.
Sifu Edward's closing word: Clate named the exact trap I escaped, the business that promises freedom and delivers captivity. The cure is a system: collect, convert, create lifelong fans, and never let a future warrior slip through the cracks because they weren't ready on day one. Automate the follow-up so the operator can stay on the mat. Honour the long mission. His runs to 2030, ours runs to the World Games. And above all, keep going. We don't entertain warriors. We create them.
Clate Mask, CEO and co-founder of Keap (formerly Infusionsoft) and co-author of the New York Times bestseller Conquer the Chaos. Learn about lifecycle marketing and the platform at keap.com.
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