Craig Swanson | Building an IT Support Company for Creatives and Scaling Business to Over $1M

Craig Swanson is a longtime entrepreneur, Consultant at Emerald, and Partner at KaisaFit, an online fitness platform. He is the Chair of the Seattle EO Accelerator program and EO Seattle and loves helping creators, educators, and entrepreneurs build sustainable businesses around their dreams.

Craig is a former Partner at The Wedding School, an online education program for wedding photographers. He was the Founder of CreativeTechs (previously known as Swanson Tech Support), which was a leading IT support firm for Seattle area creative teams. He also co-founded CreativeLive, one of the earliest live-streaming educational platforms, with Chase Jarvis in 2008 before exiting in 2015.

In this episode of the Smart Business Revolution Podcast, John Corcoran interviews Craig Swanson, a longtime entrepreneur and a Partner at KaisaFit, about his entrepreneurial journey from childhood to building an IT support company. They also discuss the challenges Craig faced scaling his businesses, how he sold his IT company to past employees, and his thoughts on running a business during a pandemic.

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Here’s a Glimpse of What You’ll Hear:

  • Craig Swanson’s entrepreneurial ventures as a child
  • How Craig helped digitize his high school newspaper
  • Craig talks about starting a business to provide IT support to creative professionals and the challenges he faced
  • Why Swanson Tech Support rebranded to CreativeTechs
  • Craig talks about building a live training business, its evolution to CreativeLive, and how he sold his IT company to past employees
  • The challenges Craig faced scaling CreativeLive and why he stepped away from the company
  • How Craig got to work with Sue Bryce and KaisaFit
  • The peers Craig acknowledges for their support

Resources Mentioned In This Episode

Sponsor: Rise25

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Episode Transcript

Intro 0:14

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome, everyone. John Corcoran here. I’m the host of the show. And for those of you who are new to this program, you know, check out our archives, we’ve got lots of great interviews with past smart CEOs, founders, entrepreneurs of all kinds of companies. We got Netflix, Kinkos’, YPO, EO, Activision Blizzard, LendingTree, and many more. I’m also the Co-founder of Rise25, where we help connect b2b business owners to their ideal prospects. And I’m so excited to have this guest on here. You know, most of my guests come from my own outreach. I’ve got a never-ending stream of people that I’m interested in interviewing. This one actually was from an incoming solicitation, which is rare, but as as soon as I saw it, I said, you know, I really want to interview this guy. 

So this is Craig Swanson. He’s the one of the Co-founders of CreativeLive, which is one of the first streaming educational platforms out there. We’ll talk about it in a moment. I actually was a guest on Dorie Clark’s CreativeLive a number of years ago, and it was such a thrill to do. But he’s got so many other things that he’s done. A longtime entrepreneur and partner in KaisaFit, which is an online fitness platform, also partner in The Wedding School, an online education for wedding photographers and portrait photographer business as well. Go check out for other podcast interviews with him Built to Sell podcasts, and every week kind of talks about exiting those businesses. But he loves entrepreneurial challenges of growing businesses from low six figures to a million dollars and more. And he also is the Chair of the Accelerator program and EO Seattle. I’m a graduate of that program. It’s an amazing program for any entrepreneur out there who wants to go be able to break seven figures. So go check it out. 

And of course, before we get into this interview, this episode is brought to you by Rise25, where we help b2b businesses get clients and referrals through partnerships with done-for-you podcasts and content marketing. And you can learn all about what we do at All right, Craig, it’s such a pleasure to have you here. And I want to start your longtime entrepreneur, your you know, so many people I interview, some like come from like, some completely technical they’re an accidental entrepreneur didn’t intend to become an entrepreneur? Well, you seem like you had it in you from a young age, to the point where like many entrepreneurs, you have a paper route. But that wasn’t enough. You also had a creative way of generating nor more money during that paper route. What did you do?

Craig Swanson 2:54

So yeah, so I tried my first paper out of 10 because I was in a small town that allowed you to but then I moved to Seattle, you had to be 12. And so I had to wait like a year where I got my paper out, got my paper out at 12 got the largest number I could get. I think I had like 350 papers on this thing. And then I realized I was like cycling through the summer and like riding my bike or so I went down to the to downtown, I got a wholesaler license, I got a business license I got and I basically built an ice cream truck that I carried on the back of my bicycle when I was delivering newspapers. And so I was delivering newspapers riding through all the neighborhoods and selling ice cream at the same time. And it’s not

John Corcoran 3:33

enough that you’re lugging all these newspapers, you also have to lug us refrigerator Hollywood.

Craig Swanson 3:37

I think we couldn’t do it on Wednesdays because Wednesday through thick papers, and we certainly didn’t try to do it on Sundays. But yes, basically, your Monday, Monday, Tuesday, Thursday and Friday are nice light papers. I could totally throw in some ice cream cart in the back. And

John Corcoran 3:53

yeah, I remember being 12 years old and either telling your parents or showing up downtown, this 12 year old saying I want to get a commercial license. I mean, what do you remember that experience?

Craig Swanson 4:03

I really wish so I suspect I just showed up. I just told my parents one day that I had got the commercial license and needed a a ride to the wholesale building because I needed to pick this stuff up. That would be my style. In fact, so I have a son of a son who just turned 20. And I remember when he turned 13 I called up my parents I said so. So what did you do when I was 13? To like, encourage me to go do this stuff. And they just looked at me and shook their head and had we had nothing to do with that. Like you would come home with these ideas and start building stuff. And this was this was definitely a if there was if there was nurture in it. There was a lot of nature built into that there’s a lot that you just kind of like took and ran with.

John Corcoran 4:48

Well, it does. You know, it does get into a whole nother conversation about nature versus nurture in entrepreneurship. But the next thing I want to ask you about is when you got the high school You’re involved in your high school newspaper, I was involved my high school newspaper, mid 90s. At that time, there’s some really early primitive software that we’re using. But you were digitizing your high school newspaper from an early age, this is probably moving from laying things out physically, I imagined to doing it more on a computer. What was that like?

Craig Swanson 5:21

So yeah, so in my, the, let’s see here, the Apple Macintosh had come out. So I graduated 1988. So between 1984 and 1988 is kind of when the first Macintosh came out. And I think the first Adobe laser printer came out around around that time. So my first year in the newspaper, we would send out our type to a line of Tronic typesetting house, it was part of the district, and they would basically type these things up and send them out to us. And I wanted to do some special things. So I literally would like ride my bike out because I have a car at that time. And I would be telling the ladies what I wanted because I wanted a special headlines. These are things and I don’t know why they like people just let me they just, they leave and they let me talk my way into things. But they literally like let me get in front of the machine and start typing in that old code, how to like do my own typesetting and that, like, let me do custom stuff and output this,

John Corcoran 6:18

right? Getting rid of you just just let him do it.

Craig Swanson 6:22

Maybe I you know, I’m just astounded by it. So a year later, that same journalism department bought the first laser printer back when laser printers were brand new.

John Corcoran 6:32

And not cheap, probably at that, no. And this would have been and

Craig Swanson 6:35

we were using PageMaker 1.0 is probably an $8,000 laser printer and like it would take forever to print and we switched over from sending out from galleys of type to basically printing out on thick paper stock, printing it out, pasting up the like I did the editorial board and a couple others. And it was an I just loved it. I poured myself into this thing. And we paste it up we did the paystub at a local printing press where the local weekly newspaper was printed for Redmond Issaquah and Bellevue. There was a weekly, I ended up like pasting up my high school newspaper next to the guys that were doing the weekly production on the Bellevue popery and the Kirkland courier review and the Redmond whatever we call it. And then my senior year, they hired me 30 hours a week to basically run the production department like to start doing the production department on computers because they’re switching over and no one knew how to do it. So I had a full time job

John Corcoran 7:33

over here is doing it for the local high school newspaper obviously knows how to do it.

Craig Swanson 7:37

Exactly. So I was doing my local high school newspaper, and then three local newspapers in the Seattle area. I say I dropped out of high school at that point, I just basically stopped going to high school at that point, because I had a 30 hour a week job. Yeah. And I had an acceptance letter to the University of Washington that didn’t include the paragraph that said, based on future grades, which most of my friends said. So I said, Okay, well, it’s not based on future grades. So what do I care about future grades. So I just stopped going to school, except for I think, journalism, calculus and worked at the newspaper, I did all this production. And that basically led into my first job, right out of college, which graphic designers

John Corcoran 8:19

I love doing that work out. So I was editor of my high school newspaper, and I loved laying it out. I love taking these different stories love the creativity within the constraints of a newspaper. I remember driving, I lived in LA. So driving from San Fernando Valley all the way to Glendale, which is where our printer was having to go there to check on things. And back then things would get messed up. And we’d get like, you know, 1000 papers printed up that had some major thing wrong with them, because we didn’t have a good way of getting proofs or anything like that. All kinds of mistakes and stuff that would happen.

Craig Swanson 8:52

So I am What am I what am I 52 now, and I’ve been in business, basically, since I was 1819. There is so much about my understanding about you launch businesses run life and basically just kind of work as a creator and an entrepreneur from journalistic production, this idea of we went to press every week, every week on Thursday. It was we were done. We were done with the best work we could do up until the point that the deadline occurred and then you ship so we shipped with the best thing we could every Thursday night. If I want to stay up till one, you know till 1am I could do that. But basically, there’s a point at which you ship it doesn’t matter if if you’ve not filled in something. There’s a white sheet, there’s a white piece of paper that doesn’t have your work on it that goes out printed the next morning.

John Corcoran 9:41

You can see that rhythm showing up in CreativeLive later, which I want to get to. But before we do, yeah makes total sense that you eventually get into doing it support for graphic designers because this seems like it was kind of a next evolution, which was that was Swanson Tech support. So talk about how you evolved from supporting those new Stanford’s into this

Craig Swanson 10:00

business. So I mean, effectively I was I went to college as a graphic design major realized that, really, I was a technology major. And I loved working with creative. So I started an IT company in 1988, which was teaching computers to graphic designers at agencies, design firms and photography studios in the greater Seattle area. And the fact that I was 18 years old. Didn’t didn’t mean anything’s in terms of my qualifications, other than like, maybe my professionalism and just, you know, understanding of life, because nobody actually knew the technology at that point. And, really, from from from that year, up until when I sold that business in 2010. Through various variations, I just was working to create support systems, generally around technology for for commercial creatives, for, for photographers, for, for writers, for ad agencies, for design firms. And I am very, very technical and very, I’ve been able to sell my intelligence in trade for time and and trade for money. But it’s always been within the support structure of helping creatives publish, create, find stability, and basically run their businesses around technology. So it’s this this way, I’ve combined these two sides of me into something that I just absolutely love.

John Corcoran 11:30

Yeah. Now, for you, one of the challenges early on was hiring. You said that that was a big struggle for you was getting good people in place and kind of replacing yourself and not being the one who was interwoven in the, you know, the threads of the business. So talk a little bit about those early challenges.

Craig Swanson 11:51

I think my like my path, I would say like is like in really like three to seven year increments. I’m like going through different phases, like the first seven years of my business, it was all about me, I was just struggling with time management, with pricing with billing with me just figuring out how to be me. And then the next seven years are when I was trying to leverage and bring in other people and was a terrible boss didn’t trust other people was basically trying to find a was trying to replicate myself instead of understanding what the company needed, and how I could actually create a space for other people to be able to grow. And one things I learned along the way is, there’s a quality of partner and team member that I can never get onto my team until I grow to be a better leader and grow to create more space for them to be able to grow. And so I I did well, I think I see a lot of young entrepreneurs doing which is I was trying to micromanage and cheap out and try to, I was trying to basically get things off my plate while trying to control everybody that I brought into my sphere, and not trusting them to do anything, right. And so like that combination of things, brought me people that were willing to work with someone like that. And yet it was a self fulfilling cycle. Yeah.