Episode #26

From Overbuilding to Focus: Chris Taylor on Learning the Hard Way

Chris Taylor spent $2M building the wrong product, cut his team from 62 to 4, and nearly lost everything. Today, Actionable serves 1,800+ programs solving a 60-year-old industry problem. Hear how brutal focus and perseverance built a leading L&D platform.
Host:
Mike Pinkus
February 10, 2026

Timestamps

00:00:10 – Intro: Chris Taylor + What Actionable Does

  • Mike introduces Chris Taylor, founder & CEO of Actionable.
  • Actionable helps training companies prove impact and measure learning ROI.
  • Chris updates the “1,000 orgs” stat to ~1,800 programs last year.
View Transcript

Mike: Hi, I'm Mike from ConnectCPA and your host at GrowthTales. Today we have founder and CEO of Actionable, Chris Taylor. Actionable is behavior change technology trusted by consultants, coaches, and organizations in five countries and in over a thousand organizations. Actionable provides training companies with the tools, data analytics, and insights to prove their impact and help measure your learning program's ROI. Thank you, Chris, for joining me today.

Chris: My pleasure, Mike. Thanks for having me. Although I do need to update the bio because we were involved in 1,800 programs last year.

Mike: You still meet the metric of over a thousand—by a greater margin.

00:01:44 – First Business at 11: Devil Sticks

  • Chris started his first business at 11 years old.
  • Manufactured and sold “devil sticks” at school fairs.
  • Early lesson: build → sell → learn profits.
View Transcript

Mike: What was that business at 11?

Chris: Oh, I made, you remember devil sticks? Yeah. So we manufactured devil sticks. Me and I recruited two of my friends at the time. And I don't remember how, there's barely any internet back then. Cause I'm very, very old. Um, and so I don't know how we learned how to manufacture these, but we made devil sticks and then we weren't allowed to call them devil sticks because we were 11. Uh, and so we to call them something else. And then we went around to school fairs, all the middle school fairs, and we set up a booth and sold them at that fair. I mean, it wasn't a real business. We didn't incorporate but it lasted. It lasted his school year and it was good. It got me my taste for what it can be like to see a trend, build something, sell it, figure out the profits, all that stuff.

Mike: I wouldn't downplay that. I was expecting paper route or lemonade stand.

Chris: Yeah, there was the both of those are true too. But you're working for some not the lemonade stand, paper route, you're working for someone else. I don't consider that it's a it's entrepreneurial adjacent.

00:03:26 – Origin Story: The Knowing-Doing Gap

  • After a franchise didn’t work out, Chris went deep into books.
  • Frustration: consuming information without behavior change.
  • Actionable began as “how do we make learning stick?”
View Transcript

Chris: I started reading a lot, business books, personal development books, self-help books. And I became really disenfranchised with consumption of information without doing anything. So basically what Bob Sutton calls the knowing-doing gap. I was filling my head, but nothing was changing in my life. And so my first sort of beginnings of Actionable was around trying to figure out how to take ideas from books and put them into practice, how to help other people take ideas from books and put them into practice. And so I started a website.

Chris: It became a bit of a subscription thing. I was becoming the book guy. And then that turned into people asking if I can train their teams. So I from book summaries to training. I was doing training. I liked training. I've always liked teaching and nothing was changing for my clients or I didn't have any visibility as to whether anything was changing for my clients. And I felt still do very strongly that the point of training is to drive change, not to deliver content at people.

Chris: And so I became really obsessed with workplace learning transfer. Basically, how do we take ideas that are shared in a training session, things I'm inspired by and help make those behaviors stick. And so that, that was really the beginning. I hired a guy off Twitter, uh, cause I'm not a coder. I hired a guy off Twitter, uh, and it was called Twitter at the time to build the initial version of what's now Actionable. And, um, and it's been, it's just been a whole series of iterations over the last, that was 19 years ago, almost 18 years ago.

Chris: And so lots of iteration and continued development.

00:05:54 – The $2M Mistake: Building “The Whole City”

  • Chris over-committed and spent nearly $2M on V2.
  • Key error: building years ahead instead of what users needed now.
  • Lesson: constraints + iterate beats massive speculative builds.
View Transcript

Chris: And really the security and privacy thing wasn't really on people's radars, right? It would come up from time to time, but there was no industry standards around it. And so it was really like, does it work? Right. And as a user, I can go through it and does it work? And so we built an initial version and it was good. And then I decided to go all in on this thing and massively over-committed. And so we ended up spending, I was almost 2 million bucks on the build out of version two of the actual platform.

Chris: And I think it could have been good, but what we ended up doing was building for five or 10 years out. Like it was, let's build the whole city all at once instead of, no, what we really need is we've been living in a tent and we just need to build like a, you know, a duplex, but we didn't build the duplex. We tried to build the whole city. And before you've done any sort of urban planning to carry this analogy to a ridiculous degree, trying to build the whole city is not a smart move. So I think it's the danger with digital build is that anything's possible. I mean, that's, that's the draw to it, of course, but the, the curse to it is that if you don't put strict parameters in place around, but what do people need right now in my universe? So I can build it, sell that thing, then see what they need next, then build that, sell that thing. And, you know, embrace like an agile approach. If you don't do that, you can end up spending a lot of time and money building something that people don't ultimately want or need.

00:07:36 – Funding + Partner + V3 + Narrow ICP

  • How the build was funded, what went wrong, and what finally worked.
  • Shift to founder-led boutique training companies ($500K–$5M).
View Transcript

Chris: So I, at the time we were bootstrapped, we still are, but for a period of time, um, I found a partner who wanted to invest a bunch of capital because he wanted to be a part of building something to the moon. And so he put in, he committed 5 million bucks to the build out of this business. Um, and we took most of that or a big chunk of it at the B he was trotting it. So we took most of what was coming in and we, bought a dev shop and we, sounds like we bought a zoo. We literally bought a shop. We.

Chris: deployed 20 people full-time Western world salaries against building this thing out. And so you can burn through 2 million bucks pretty quick when you're paying for that sort of development team.

Mike: Okay. So, and, look, like you guys are smart. So $2 million, again, it's a big absolute number, but it's all relative to who your ideal customer is or your ICP. So who were you planning on selling to back then? Who's the ideal customer at the conclusion of a build like this? Like who are you targeting?

Chris: Yeah. So, I mean, this was eight years ago and I would say it was a relative. Well, I'll put it this way. We don't use a single line of code from what we built over that $2 million spend. So. Like it did not work just for anyone listening or watching. That was not the right approach at all. That business partner for completely unrelated reasons ended up going to prison about halfway through the deployment of that capital. So that was a whole thing. But to your question.

Chris: Back then, we didn't really know. And I think that's part of why we were spending 2 million bucks. We were trying to satisfy the needs of about five different avatars. And so we ended up building this fairly convoluted mess that didn't serve the needs of one at all. And so V3 of the build, and again, this is like nine years ago, V3 of the builds was this one little thing within this giant ecosystem that probably proportionally cost us, I don't know, 150 grand, 200 grand.

Chris: That's the thing that seems to resonate enough that if we're going to go again, let's just do that and do that really well. And so we did that and we improved it, but we didn't improve it wide. We improved it deep. it became stronger, more robust and more useful. And that caught on. And so really for the last eight, nine years, we've been growing.

Chris: The answer to your question was of all, so we play in the learning and development space, meaning we sell to executive teams and L and D teams and HR teams and consultants and facilitators and trainers and coaches. And were doing all of that back then, big companies, small companies, everything in between. For the last three years, who we have served best and maniacally is founder led boutique training companies doing between half a million and 5 million a year based in one of five markets.

Chris: And that's it. That level of focus, niching, whatever you want to call it, I would say that that is one of the single largest contributing factors to our success over the last five, six years.

00:10:41 – How Actionable Attracts Customers

  • Content marketing and insight reports as the main growth engine.
  • Using large-scale data to stand out in the L&D space.
View Transcript

Mike: And how do you attract those customers? Because you've built a product that helps that avatar prove out their worth. Like really you're a tool to help prove that they've made an impact. How do you grow that audience yourself? So like, how have you been growing that customer base?

Chris: Yeah, I think, I mean, the advice of go where your clients are is great unless your people don't congregate in many places. So we found the couple places that they congregate and we, you know, we're part of that universe. But a big piece for me has been content marketing.

Chris: It's been a really beautiful flywheel about three years ago, I guess, or maybe four. Probably around the time of that growth, we started producing insight reports.

Chris: We have all this data inside the platform around what makes learning stick and how to prove the impact of it. And in an industry where case studies or reports tend to include data from like 24 respondents, 72 respondents, really here's 80,000 participants and the data around it tends to attract attention.

Chris: So our, our sort of manufactured viral marketing has been let's create a report once a quarter. We'll do an annual rollup. Let's post it everywhere.

Chris: And drive people to the report. They get on our list. They learn more about our world. And then we do strategic and infrequent invites to come to a workshop, which is like a two-hour session, where we can dig deeper on applying some of the stuff to their work that makes the tech the obvious next step.

00:12:18 – Team Structure + Referral Mix

  • No agencies; fully in-house team.
  • Breakdown of where new clients come from.
View Transcript

Mike: Wow. And are you doing this all yourself or do have agencies involved for the marketing piece?

Chris: Yeah, no agencies. I have an intact, or in-house team. I've got 13 on the Actionable team. And so most of that is, we've got about half as engineering and then about 30 percent is like partner success, client success, client services. And then we've got a couple of people on the marketing and sales side.

Mike: And do you track, I'm guessing you track the metrics on this. You did this three years ago. Can you see how much of your lead flow is coming from that content marketing versus like referral or, because I'd imagine you get a lot of referrals too, meaning someone makes a big impact on their customer. Like you've got to have this in your, in your toolkit. Do you know what that split is offhand or maybe not?

Chris: Um, referrals probably still make up, I don't have it like at my fingertips, but it's probably still 35 percent of our client growth, not leads, but clients.

Chris: I don't track it at a lead level. Honestly, we just wait until they're signing and then figure out where they came from.

Chris: And then about a third comes from this report strategy that I described. And then about a third comes from hearing me speak on podcasts, stages, et cetera.

00:13:30 – Events, Stages, and the Fishing Net Analogy

  • Why showing up matters even if only part of the room is ICP.
  • Balancing focus with broader opportunity.
View Transcript

Mike: Wow. And do you go to any events? Like you mentioned, like you have a very specific ICP, meaning like you're like specific revenue. It's learning and training companies. So it's like, I can't even think myself of like, where do those people live? I'm sure you've done research of like what events and stuff, but do you do in-person events and things to try to seek out building relationships with that ICP?

Chris: Yes. Yeah, absolutely. I used to do so. There's a couple of thoughts in here. So one is the fishing net analogy.

Chris: So I get really specific around who we're targeting. And then we go to the places, which we'll talk about in a sec, but we show up where they are as much as we can. We create content to attract them.

Chris: But it's the fishing net analogy where you might be fishing for tuna, but you're still catching a bunch of other fish in the net.

Chris: And that happens. And we do work with, like we work with enterprise organizations. So, you know, large scale household brands, their L and D departments, we work with them. We don't focus on attracting them, but we do work with them.

Chris: Same thing with smaller, earlier stage consultants that aren't at the half a million bucks. We have other vehicles to help them get to half a million and to use some of the tech. So we do have other offers.

00:14:44 – Stepping Away, Family, and Returning to the Stage

  • Why Chris stepped back from events for several years.
  • Returning to speaking with a book coming out.
View Transcript

Chris: I used to do a lot. Then we had a kid, then COVID happened, then we had another kid. And so I deliberately for about a—

Mike: Nice. What do you have by the way?

Chris: We have two boys and a dog. Thanks. Yeah, so I used to do a lot. I was on the road at least a couple of times a month. I deliberately took about a six year hiatus.

Chris: And then last year I just started again, back on stages. I got a book coming out next year. And so we'll use that to get more stages in the fall.

Mike: You wrote a book? Where did the time come from to write a book?

Chris: I have an exceptional wife.

00:15:53 – Top Two Biggest Challenges & Final Advice

  • Life-defining setbacks, cash flow pressure, and being early to market.
  • Lessons on leadership, patience, and resilience.
View Transcript

Mike: I normally ask about challenges in the business. You mentioned five million bucks, a two million dollar spend, your partner going to jail, like all this stuff going on. You’ve already kind of given away, I guess, some of the biggest challenges, but maybe there’s been bigger challenges.

Mike: If you were to give me the top two biggest challenges you’ve gone through, leading into 2025, what would you say they’ve been?

Chris: Yeah, so let’s go one micro and one macro. On a micro basis, my business partner going to jail halfway through his deployment of capital was, I would say, a life-defining challenge.

Chris: He was based in Australia. It was literally the middle of the night when I got a call from his ex-wife saying he was in jail and the money wasn’t coming.

Chris: That kicked off a four-year journey of not knowing how I was going to make payroll at the end of each month, with a newborn and a wife who had just had a C-section.

Chris: The biggest thing for me was an ego reset. My approach historically was: I’ll just get it done. I’ll follow the path I set, stubbornly, bullheadedly ignoring reality until I reshape reality to my will.

Chris: We were burning three hundred grand a month and I had four hundred thousand in the bank. There is no reshaping reality there.

Chris: I said I was going to keep everybody. Eight months later, I let a lot of people go and had more debt. That punched me in the face.

Chris: You can influence things, but you don’t get to decide how the world operates. That was humbling and helpful, and it made me a much better business operator.

Mike: Was that your first time going through a big round of cuts like that?

Chris: Yeah. We went from sixty-two people down to four. It was brutal. Letting people go when it’s no fault of theirs is the hardest thing any leader goes through.

Chris: I buried my head in the sand longer than I should have, and that hurt the people who stayed.

Mike: And the macro challenge?

Chris: I saw the need for impact measurement in training programs twelve years before the industry did.

Chris: People would say, “That makes a lot of sense, but we don’t have a budget for that.” If you’re too early, you’re constantly fighting “not no.”

Chris: No client has ever replaced something with Actionable. It’s always been net new, and that’s hard when you’re creating a category.

Mike: You’ve been doing this since 2008. What do you love about the business, and what’s changed the most in you?

Chris: I can see my personal growth plotted against the business financials. When I grow, the business grows. When I stall, the business stalls.

Chris: I love tackling a big unsolved challenge. Proving ROI on training has been talked about for sixty years and mostly unsuccessfully solved.

Chris: I also don’t take for granted that I get to choose my universe—who I work with, who my clients are, who’s on my team.

Mike: Final question. With AI everywhere, where do you see Actionable going over the next three to five years?

Chris: We were intentionally slow with AI. I didn’t want to just slap it on as a feature.

Chris: Short term, it’s about internal efficiencies and speeding up where clients spend time. Long term, I don’t think dashboards and screens are the future.

Chris: I think information becomes auditory, visual, and surfaced on demand.

Mike: Chris, I really appreciate you joining me today.

Chris: Thank you, Mike. I enjoyed the conversation.

Meet Our Host

Mike Pinkus

Co-Founder: ConnectCPA
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Meet Our Guest(s)

Chris Taylor

Founder and CEO of Actionable
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