EO Seattle | How To Be a Creative Entrepreneur

Craig Swanson is the Co-founder of CreativeLive, the world-leading live and online classroom for creative entrepreneurs. Getting his start delivering newspapers, Craig is a natural-born entrepreneur that loves the challenge of growing an online business from low six-figures to breaking $1M and building the team and systems to a scale far beyond. Craig is also a board member and the Accelerator Chair at EO Seattle, a partner in KaisaFit, and a consultant for Emerald.

Here’s a glimpse of what you’ll learn:

Craig Swanson’s entrepreneurial journey that started with a paper route (combined with delivering ice cream)
How Craig combines his talents and love for creativity, publishing, and technology
Balancing running a business, letting team members grow, and being a leader
Why Craig rebranded Swanson Tech Support to CreativeTechs
What prompted the beginnings of CreativeLive and how it’s evolved
How Craig exited CreativeTechs
Craig explains the growth and scaling of CreativeLive
Partnering with and growing Sue Bryce and KaisaFit

In this episode…

As an entrepreneur, are you exercising your creative side? Where can you get the help you require to leverage your creativity and scale your business?

Creativity positively impacts the world, moving it forward and helping people foster ideas and become innovative. When you take knowledge and combine it with passion and your creative side, there’s no telling where you’ll go. Entrepreneur Craig Swanson combined his love for creativity, publishing, and technology, taking him on an entrepreneurial path he would not have foreseen. Leaders and entrepreneurs don’t always know how to use their creativity to achieve success. Creators and entrepreneurs can now learn ways to be creative in all aspects of design, photography, video, music, and entrepreneurship, thanks to CreativeLive.

In this episode of the Rising Entrepreneurs Podcast, John Corcoran sits down with Craig Swanson, Co-founder of CreativeLive. Craig talks about his entrepreneurial journey and what he learned along the way. He explains the early challenges he faced running his business, how he started and scaled CreativeLive, and his partnership with Sue Bryce and KaisaFit.

Resources mentioned in this episode

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Episode Transcript

Intro 0:02

Welcome to the Rising Entrepreneurs Podcast where we feature top founders and entrepreneurs and their journey. Now let’s get started with the show.

John Corcoran 0:11

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, check out our archives got lots of great interviews with past smart CEOs, founders, entrepreneurs of all kinds of companies. We got Netflix, Kinkos, YPO, EO activation, Blizzard, Lending Tree and many more. I’m also the co-founder Rise25 we help connect b2b business owners to their ideal prospects. I’m so excited to have this guest on here. Most of my guests come from a product, 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 soon as I saw it, I said, 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. Longtime entrepreneur, partner and KaisaFit which is an online fitness platform. Also partner in the wedding school and online education for wedding photographers and portrait photographer business as well. Go check out for other podcasts interviews with him Built to Sell Podcast and every week. Craig talks about exiting those businesses. But he loves entrepreneurial challenges of growing businesses from low six figures to a million dollars or 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 referrals and strategic partnerships with done-for-you podcast and content marketing. And you can learn all about what we do at rise25.com. All right, Craig, it’s such a pleasure to have you here. And I want to start your longtime entrepreneur, so many people interview, some like come from like, some completely technical they’re an accidental entrepreneur didn’t intend to become an entrepreneur. But 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 2:26

Yeah, so I saw my first paper out of 10, because I was in a small town that allowed you to that that I moved to Seattle, you had to be 12. And so I had to wait like a year before I got my paper out, got my paper out at 12 got the largest number I could get, I think I’d 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 downtown, I got a wholesaler license, I got a business license 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.

John Corcoran 3:05

It’s not enough that you’re lugging all these newspapers, you also have to lug a refrigerator.

Craig Swanson 3:11

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

John Corcoran 3:24

Do you 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, do you remember that experience?

Craig Swanson 3:36

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 need to pick the stuff up. That would be my style. In fact, so I have a son, I have a son who just turned 20. And I remember when he turned 13. I called up my parents I said 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 that we had nothing to do with that. Like you would come home with these ideas and start building stuff. And this was definitely a 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 4:21

Well, it does get into a whole another 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 were 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 4:54

So yeah, so 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 that time. So my first year in the newspaper, we would send out our type to a line of Tronic typesetting house that 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 another 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 that is 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 they’re like, let me do custom stuff. Maybe I even 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 6:05

And not cheap, probably at that point too.

Craig Swanson 6:06

No. And this would have been and we were using PageMaker 1.0 is probably an $8,000 laser printer and it will 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 I just loved it. I poured myself into this thing. And we pasted up we did the paste up 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 curry 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 were switching over and no one knew how to do it. So I had a full time job.

John Corcoran 7:06

Over here. He’s doing it for the local high school newspaper obviously knows how to do it.

Craig Swanson 7:09

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. 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 had. 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 was my graphic designers.

John Corcoran 7:56

I love doing that work out. And 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 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 8:25

So what am I, what am I I’m 52 now, and I’ve been in business, basically, since I was 18, 19. 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, 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 1am I could do that. But basically, there’s a point at which you ship it doesn’t matter 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 9:14

And 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 it seems like it was kind of next evolution, that was Swanson tech support. So talk about how you evolves from supporting those newspapers into this business.

Craig Swanson 9:35

So I mean, effectively I went to college as a graphic design major realized that really, I was a technology major and I loved working with creatives. 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 mean anything in terms of my qualifications other than, like, maybe my professionalism and just understanding of life, because nobody actually knew the technology at that point. And, really 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 commercial creatives, for, for photographers, for writers, for ad agencies, for design firms. And I am very, very technical, I’ve been able to sell my intelligence in trade for time and, and trade for money. But it’s always been within this support structure of helping creatives publish, create, find stability, and basically run their businesses around technology. So it’s this way, I’ve combined these two sides of me into something that I just absolutely love.

John Corcoran 11:03

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 inter woven in the threads of the business. So to talk a little bit about those early challenges.

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Craig Swanson 11:24

I think my path, I would say like, is like really like 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, or when I was trying to leverage and bring in other people and was a terrible boss didn’t trust other people was basically 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 did what I think I see a lot of young entrepreneurs doing which is I was trying to micromanage and cheap out and 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 it was a self-fulfilling cycle.

John Corcoran 12:41

Yeah. And actually one of your early hires when your first hires actually ended up leaving shortly later, and that was a devastating impact for you, talk to me about that.

Craig Swanson 12:52

Yeah, so that was one of my very, hires is even maybe overstating it, because this is freelance, this is freelance, where I was looking for like lifetime permanent commitment from somebody for somebody who’s emotionally involved in my company as I was, and yet I was trying to commit as little to them as possible. And at a time, we were talking about potentially him coming as a partner my business or trying to figure that out, he ended up becoming a partner in a competing business. And so not only did I lose the person I thought I was going to be able to work with to build into the next phase. But then he became my competitor. And basically, I watched my competitors start to figure out things that I was struggling with.

John Corcoran 13:32

And that’s devastating. This business kind of evolves and Swanson Tech Support becomes CreativeTechs. Is that right?

Craig Swanson 13:44

Yeah. Around 2000. I started business mostly in 2000, in 1988. So we had the .com, bust all this stuff. There were a lot of my clients that were design firms that were starting to our business, they were service based design firms, technology was shifting. And one thing that I started to notice is that in a service based design firm, the people that had their name, and the company name tended to have a lot less success, creating anything that lasted beyond them. Now, there’s probably indicators of other things beyond just the name itself. But when I looked at that, and I looked at what I was trying to build, I really started to see that me Craig, something called Swanson Tech Support was branded around me it wasn’t a brand about my audience. It wasn’t giving room for other people. And also there was just this mentality around it. That was not what I wanted to build. And so I rebranded as CreativeTechs, we were techs for creatives. This was also probably the point at which I actively tried to be hiring people smarter than me with different skills than me, and I think started to get into the process of learning how to allow others to lead within my company and how to learn how to be a leader of leaders, I would say I was a fledgling at this, but I was starting to show signs of it. And I was starting to show signs of a business owner as opposed to just a single practitioner trying to like leverage other people to do what I tell them to do.

John Corcoran 15:16

Now, it was interesting, I was looking into your background, I was reading a couple of old blog posts here. And I saw the evolution of what became CreativeLive, which was so innovative when it came out. But you kind of baby stepped into it, because you got into education and training, you kind of incubated the idea. what point did you get involved to Chase Jarvis? And at what point did you start to test around with this idea of building this kind of platform.

Craig Swanson 15:48

So I had always loved education and writing. And so I actually I even way back when I had written a newsletter for Photoshop 1.0. So way back when so I’d always had some type of publishing mindset. But what became CreativeLive really started incubating inside of my IT company, around the time that I had created enough space that other people were running most of the business. So at that point, I was not doing most of the client services, I was doing some of the sales, I had really good technicians that were doing most of the other work. And also the company was profitable. So with all those things, I like to joke that other business owners at that point, that’s the point that they buy themselves a boat. And so I took my boat payment, and instead of buying a boat, I poured it into another hole that you can pour money into, which happened to be for me, a internal startup and internal online startup company. And I ended up hiring a really great trainer, Jason Hoppy that was an expert trainer in Photoshop, Illustrator, all the Adobe products. And then for about a year, we built out our own studio. And we were experimenting this with this way of creating bite size education. My original vision was people were like my clients, were going to come here during lunch and have like lunch and learns. We’re going to create all these different things that wasn’t really working. So we were iterating around all these different ideas around trying to create different ways of creative education.

John Corcoran 17:19

And this is, what 2008 2009 time period.

Craig Swanson 17:22

This would have been 2006 2007 2008. So like in a range.

John Corcoran 17:28

And I think YouTube started in 2005. So we’re talking early days of online video, are you streaming it? Is it kind of live online? Or is it recorded video?

Craig Swanson 17:38

In the very early days, it was just a lunch and learn. So we’re just trying we’re actually creating content that we could like, basically deliver in an hour and the idea that people drive to be in person with us, so wasn’t even online. And then we weren’t making any money. I mean, it’s like we are spending 60,000 $100,000 a year on my education per minute probably brought in $5,000 a year. So it was a not a very good business. But it was my love. And so impersonal is not working. We thought, okay, let’s switch to webinars, this new thing had just come out, go to webinar, we were playing with this thing. So we started doing some virtual classes. And then I think really what ended up being the trick that like tripped over to make what CreativeLive as possible, is we started experimenting with something that did both at the same time where we took our in person classroom, had people in person there in person, and simultaneously did a broadcast to a webinar externally. So that the people watching externally, most webinars at the time had this dead performance of the person teaching because they were not talking to anyone, they were just talking to a screen, they had no sense of anything. So I wanted from Jason I wanted his in person audience I wanted laughter I wanted humor, I wanted him to be like responding to an audience in front of him. And so we end up building this classroom that had about five or six people in person that were paying to take the class there. And then we had, 10 11 12 people that were tuning in remotely. And that created such an amazing connection. Jason had the instructor had an audience and person to react to. We had the people watching remotely that let us like support more people. And then I was making sure in the back end that I could like have their audio from the remote people come in. We did a lot of work to basically try to make this all work working where were Jason’s eyeline was going. So all this said, we’re doing all these things too. I try to create this hybrid classroom environment which leads up to 2008 when the economy tanked and we had the wave of banks going out of business. In fact, Washington Mutual Bank in Seattle was my biggest client and they went out of business. And all of a sudden, this IT company that was running without me. That was giving me the owner my boat payment to go reinvest in my little favorite little hobby.

John Corcoran 20:07

Did you get sucked back in, did you have to cut the cord and get sucked back into running the IT company?

Craig Swanson 20:13

Basically, the IT company could no longer afford to do nothing owner. So I needed to do something. And I remember I was going over spreadsheets, I was just basically I really didn’t want to give up the classroom. But I knew that that was the thing I need to do.

John Corcoran 20:30

Put years into it. And you’re passionate about you built the studio, you got the momentum. And you’re that’s like devastating for you.

Craig Swanson 20:39

Exactly. And I was going for spreadsheets where I was looking at Google ads. And I was basically just saying is there any way I can make this classroom pay for itself and like I was looking at what it cost to do advertising all these things. And this spreadsheet over this weekend, every time like I was getting a zero at the bottom or a negative number. Basically, nothing I could do in terms of like pricing strategies or advertising was getting this thing to actually, like not cost more than was doing. And I remember just kind of like a one point just saying, exploitive? Why don’t we just give the thing away for free? I don’t think swearing your podcasts are basically just, if I’m gonna be losing money on this thing, why can’t I just give this thing away for free. And at least we’ll go out with a large audience. And so we basically scheduled the final class for this online course it was a 10 week Photoshop course. So we had the curriculum all set up. And at that time I had like had about a three out of 30,000 person email newsletter list that I built up over the years just because I liked writing. And we emailed everything and like put this over social just basically said free 10 week Photoshop course just show up. You can watch it when it’s live. If you want recordings of it, you can you can pay for the recording. And that basically is the CreativeLive model that the very first week of that 10 week course. We had a 1000 person license for go to Webinar. And I genuinely thought the 1000 person bullet point, I thought the 1000 person bullet point was a marking number. I thought there’s no way that they’re actually paying attention how many people there’s the end at 1000 people like it cut off our new people. And so I’m angry, frustrated. But it was great. I mean, like there’s a lot of energy. And so what is happening is over the next several weeks, we couldn’t upgrade that limit, we couldn’t upgrade that limit. So we just started the webcast early on earlier. And so basically, it would be filling up five minutes early, and then 10 minutes early. And so basically, like there was such a capacity desire for this thing, that people were basically just filling up the funnel.

John Corcoran 22:48

Probably people who are out of work and looking for work or looking to upgrade their skills. So there’s good sense.

Craig Swanson 22:53

Yeah. And then we sold recordings, and we basically just we sold recordings for I think for 50 bucks. And we made $30,000 off of this first 10 week course.

John Corcoran 23:05

That compared to previous revenues, is that a lot more than what you’ve done previously?

Craig Swanson 23:11

Well, I think I mentioned before we were doing like $5,000 a year like it was not an economic engine. It was a love engine. It was not an economic engine.

John Corcoran 23:20

It kind of stumbled into a freemium model.

Craig Swanson 23:24

Exactly. And a freemium model that really like everything inverted and all of a sudden, it became the driver that kept my company alive. So my IT company, actually now instead of the company have an important $100,000 a year into the training, it turned around the train, the training company was now generating a lot we did a Photoshop course that did $30,000 in sales. We did an illustrator course, I was talking with Chase. So you asked when I met Chase.

John Corcoran 23:50

Chase, by the way, well, very well regarded photographer who at the time had built a social media following I guess you’d call it early days of social media.

Craig Swanson 23:59

Absolute Chase Jarvis with one of the big photographers, like worldwide in Seattle, like was early on in terms of doing online education and just sharing the behind the scenes of what was considered to be kind of a secret, like untalked about backend of how photographers work. He had been a client of mine, I think for about a decade. So remember, I supported the biggest ad agencies, design firms and photography studios in the Seattle area. And Chase was one of the biggest photography studios in the area and had been a client of mine for years.

John Corcoran 24:29

Got it in a working relationship.

Craig Swanson 24:32

I think we were on a panel together at AI GA at the graphic artists guild. And at a break I was talking about, like what was happening with the Photoshop course. And we just started talking and basically over about the next four or five months. Now I expect out moving this thing that had been in prototype stage inside of my company. We spun it out in 2010. So in terms of timeframe, the 2008 is when the economy tanked around the end of 2009 is when I kind of knew that I needed to do something with my IT. So my Hail Mary with the education copy was around 2009. And then between 2009 2010 is when Chase and I were talking and then we launched CreativeLive in 2010.

John Corcoran 25:19

And then by that point, was your IT company back on more stable footing?

Craig Swanson 25:25

So by that time was actually it was okay. It was okay. So I sold my IT company to…

John Corcoran 25:31

Key employees. Right, tell the story about these employees, because they had actually left and you had a bunch of different relationships with them in different capacities.

Craig Swanson 25:41

Yeah, Tim, who is now one of the owners of CreativeLive, Tim and Kyle had been with me for about a decade. Tim actually was a consultant of mine that worked at Washington Mutual, he ended up leaving my company going to Washington Mutual, and in doing so invoking our non-compete that we had with our employees. So we actually negotiated his exit where I was working to enforce my non-compete with him as he was going to my biggest client. So we negotiated him exiting as an employee to my biggest client where he became my boss.

John Corcoran 26:18

So rather than you putting your foot down, saying, absolutely not, no way, I’m gonna force this non-compete. It sounds like it was a more of an amicable discussion.

Craig Swanson 26:26

Yeah. I mean, so for the most part, I am always trying to make sure that I’m taking care of me. But also I try to play win, win, so when he left, we just try to make sure that we’re taking care of as long as and he’s taken care of. And so basically, he actually was able to use the lever because he didn’t really want to be the IT guy. So we actually appreciated being able to say, I can’t do this work that I’ve been doing with you, because I was gonna do other work. And so he got to use us, he got to keep using Kyle. And then a couple years later, Kyle left, so Kyle left. And so he actually went to start his own gig and we actually even negotiated we went through his client list and I let him buy out her gift, I basically went through his client list and gave him a couple clients that he was really core with, it allowed him to kind of start his practice, in return for him, not going after other clients and just kind of negotiating the terms under which he was going to leave. I think a lot of illustrators rose are so afraid of this, they never talk it out. And they create a lot of dead end conversations where basically have two people like not trying to negotiate. So we’re basically really proactively trying to work this out. And then when Washington Mutual went out of business, because of all that, Tim left Washington Mutual, I lost my biggest client, Tim lost his current job. And then Tim and Kyle went into business together as competitors.

John Corcoran 27:00

Okay, competitors, to what you were doing.

Craig Swanson 27:57

Exactly. Meanwhile, I had other team members, but yeah, they were no competitors. And Kyle had a few clients that we’d passed along to him. And then, you can interpret this. And then they did a marketing campaign that included people that Kyle was expressly prohibited from marketing to.

John Corcoran 28:17

You found out about it.

Craig Swanson 28:18

I found out about it, it could be a mistake, or it could be intentional. But we then had a conversation about that. And I went back and enforced our non-compete with Kyle. I think in a way that kept relationship, like I mean, I don’t think it burned our relationship. I mean, it would probably put us under pressure. But then about six to nine months later, when I was selling my business. I actually had an offer from a couple a couple other it pa companies, but generally feeling good about it. I was able to go back to Tim and Kyle and say, hey, I’m selling my business. This is what we’re getting offered. You guys can if we can work it out. I would rather have you guys run this because you already know how to do everything. Like all the clients know you. And we worked out we worked out a deal. They bought it. What they bought it for totally worked for them. It also provided some support for me and my family over the next three years. As we migrated over to the CreativeLive startup when you’re getting outcome.

John Corcoran 29:20

Nice to have that cushion while you’re working on building up CreativeLive.

Craig Swanson 29:23

Yeah, and today, I mean I think we’re a decade later. Kyle and Tim are still the IT company that supports my wife, I am not my wife’s tech support. And so I like to say like, like this is a reference I can give these are people like if you ever want to know who Craig is, these are people that reported to me as employees that I reported to as clients that we have had adversarial relationships or competitive relationships and where we have actually negotiated some uncomfortable non-compete conversation and eventually who bought my business?

John Corcoran 30:04

So that relationship like that.

Craig Swanson 30:08

Yeah. And I’m not saying that every report they would have of me would, but they know me on all that and so like they’re the referral I give because there is not an aspect of me in business that they have not seen some side of.

John Corcoran 30:22

Now let’s talk about CreativeLive, I must have done it probably around 2013 2014 or something like that, as I said, my friend Dorie Clark was doing and she had me come in as a guest to the San Francisco studio. And this was not a small operation at this point. So reflecting back on what you said earlier about the difficulties of managing a lot of people. Now you’ve got a huge operation. I mean, it was like going down to the NBC Studios or something like that. There’s makeup, there’s hair, there’s a green room. There’s a studio, huge studio and rows and rows of desks. And then there was a party afterwards, I had a blast. When I did it, it was really a lot of fun. But what was that like for you getting to the point where this? I don’t know if you took on VC capital or not. But it’s a huge operation. And at some point.

Craig Swanson 31:09

Yeah, I was laughing. He says not small operation. At that point. That point you saw, I think it was a million dollars a month in payroll somewhere. If not, we were within striking distance of that. It was it was a big operation to know. It exploded like a rocket because we had just hit the economic downturn. And so basically, when we launched in 2010, it was messy. It was a messy business. But startups I find are messy. But we hit the audience and the audience was interested, we were serving a market and they rewarded us with purchases and everything else. So we grew tremendously. I think we did a million dollars $1.2 million in revenue in the first year and just grew and grew and grew. Two years into this. We did take VC funding from an a round from a group at Silicon Valley Greylock.

John Corcoran 32:08

That’s a top tier VC.

Craig Swanson 32:09

Oh, absolutely. We were watching the Facebook movie and like their characters in play, they were part of our dynamic that are being played by various famous actors on the TV. And that was like, a business education on steroids. I learned a lot about scaling, I learned a lot about where my strengths are in scaling, and my where my weeks our weaknesses are in scaling, and in terms of what type of personalities and team are needed to really be able to, like take things to the next level.

John Corcoran 32:15

Yeah. What was it like for Chase also to I mean, many most photographers are probably like small group operations that have no one working for them. That it’s an unusual dynamic for someone to go from being a photographer, a well-regarded photographer to running a big business like this.

Craig Swanson 33:03

I mean, Chase was very much a visionary. So I think like from a dynamic standpoint, Chase is very much a visionary does not very focused on brand very focused on audience perception and connections within the community. And very much less detail oriented in terms of finances, or technology or things like that. And I’m kind of the reverse, I am much more detail oriented, much more focused on kind of the technical side, and where I’m involved with creators more on creating the structure around creative as opposed to creating the creative. And honestly, like, Chase’s company, as a photography studio, he always was a fairly large company. So he always had like, a good healthy number of employees, like he always had like a team of like five to 10 people. And that is about the size of my company. So in terms of both of us, both of us had different coping styles and different like, personality styles. But neither of us were prepared or qualified for what CreativeLive grew into.

John Corcoran 33:03

Now, at what point did you say in your bio, now that your passion really is taking businesses, kind of the accelerator model from 100, to under $300,000 to a million bucks or more, that seems like really what you really enjoy. But there must have been a point where you look around, you’ll see all these different people, you don’t know their names. And maybe you’re like, I don’t know if this is for me, did you reach a point like that with CreativeLive?

Craig Swanson 34:31

I did, but also, I knew from the beginning that I wasn’t gonna be CEO. So I was a CEO of CreativeLive in the early incubator days, while we were figuring out where product market fit was. And then we brought in John Cunningham, who, as a CEO at that time to basically kind of like start to build the systems. And John really knew how to basically put together the executive team, build the team, all that and then Chase and I basically reported to John in different areas. So we may have been on the board, we may have been like founders. And there was this kind of triangle dynamic, where John was the CEO and fought for the control that CEO needs to have. And then you had two founders, who were major stakeholders, and also necessary components and employees to make the system run.

John Corcoran 35:25

Did you ever find at some point that you weren’t sure where you fit up fit in? And that dynamic?

Craig Swanson 35:30

Oh, yeah. Oh, yeah. And at some point, it grew to a point where I did move on, because at some point, in 2015, when Chase became CEO, after we’ve done through a couple rounds, like I did move on to the next phase, for me personally, because I really realized, I love the act of building a company and creating a company to about that $1 billion dollar a year mark, basically that like, for me, the act, the hands on act of creating, solving, finding the product market fit, working with creatives, basically, all that struggle of figuring out how to build a sustainable business that can break a million dollars, that is like my sweet spot, the next March, going from 1 million to 10 million and then beyond, I move into a mentorship role for different people through executive timber, different areas, but it actually gets to a place where I’m not the person to lead it or handle the details in that. And so I’d say, definitely I know about myself now. I think that emotionally, I was left less comfortable with that during CreativeLive, like during CreativeLive, it felt like power is being stripped from me, I was not. I was discovering this about myself at the time and learning what it took to grow and may be in denial. We’re struggling with it. Whereas today, it is something I built into my program today. Like I get companies up to a place and then basically, around the time we’re crossing a million, I’m also kind of cherry picking who is going to be the executive team that’s going to take it to that next level. And how are we going to basically build that team so it can go and thrive?

John Corcoran 37:10

It’d be great if we came with an instruction manual, then that told us these things, but it’s really once you cross those bridges that you learn those things. So that natural transition to some of the current more current work you’ve done with Sue Bryce. Sue Bryce was a similar kind of idea here, she was a well-regarded photographer, right. So talk about how that partnership came about.

Craig Swanson 37:32

So Sue is actually an instructor CreativeLive. So she taught her first class in 2012. And then around 2014 2015, one of the things that happens with instructors on Creative blog, especially as things are developing, because when CreativeLive started, nobody knew how to do live streaming, the technology was all hard. CreativeLive made a lot of instructors really big and famous and made him a lot of money in a really short period of time.

John Corcoran 38:00

You had some, some people like Tim Ferriss, the Brene Browns that are now much bigger individuals that you can claim credit for some of the growth in their career.

Craig Swanson 38:11

So those two Tim and Renee, yeah, super nice. Like they’re huge when they got involved with CreativeLive. But yeah, there’s a lot of people that like, kind of like, use CreativeLive as an initial springboard for really significant impact. Yeah, and so Sue got to a certain level impact and then then made a conscious choice that she was going to go do her own thing. And so she did that a little bit later, Chase became CEO I had kind of made my peace in terms of like, where my role and CreativeLive was and critical I was growing to a place where I was an owner but I wasn’t really involved in so I went through like I exited CreativeLive still an owner but basically went through my non-compete burn out period and all that and at some point Sue and I got together and like we’re both free of CreativeLive, she’s been doing her own thing and she had her online education company was doing about $600,000 a year and she knew that she knew she was like bumping into a non-sustainable place for her. She was either gonna blow it up or like, you know, get rid of it or like just she was basically running into her own limitations in terms of what she wanted to do and where she was skilled. And then I came in along with a couple other partners, we came in and basically partnered with Sue Bryce created the incubator company that I was doing that I basically did a lot of work with. And we basically took Sue Bryce, I think, yeah, we basically built Sue Bryce into a company was doing about $6 million a year. Eventually it got sold and acquired by Emerald, one of the biggest in person tradeshow companies out there. And that became really like the first big incubator company that I took first to a million or was part of it. team that took first to a million and then built out the team that could basically grow that to the next level.

John Corcoran 40:06

And now you’ve got another one you’re working on. This is the KaisaFit.

Craig Swanson 40:10

Yep. And then KaisaFit. KaisaFit, we started in 2019, which is an online fitness platform.

John Corcoran 40:16

Good timing, by the way, leading right into the pandemic, but you plan that really well.

Craig Swanson 40:20

I’ll tell you what it was really lucky. And it’s also really lucky that we did our prototyping so quick, because we basically started in June of 2019. And if we had not had kind of the scrappy prototyping, like, prove out the audience find product market fit mentality, we would have missed the opportunity that was about to be like, laid on the entire planet. And when I say opportunity, like terrible disaster, but we were selling online, we were selling workouts that people could do in their living room at a time when the entire world is about to be locked in their living room for a couple years.

John Corcoran 40:58

Yeah, yeah. And so there must have been some moments though of fear going into it, or were there not any moments of fear?

Craig Swanson 41:06

Oh, yes. I mean, a fear. Fear always fear. So for me, like I was gonna ask you where fear of the pandemic fear of failure, fear, like, life is fear.

John Corcoran 41:17

It’s interesting how many entrepreneurs and businesses that grew through the pandemic, at least the first month, two months, no one knew anything, I had no idea what’s going on. They’re scared for their family, for their parents, for their kids, that sort of thing. And then and all of a sudden hockey stick starts.

Craig Swanson 41:36

I would say also, that was both luck. And also choice. So we did we had a conversation, we had a conversation both at Sue Bryce education and also at KaisaFit because I tend to get so I tend to have one company that isn’t scaling more than I’m mentoring in so I don’t not use as much and I have one cup of I’m turning to be growing. And so I’m usually have time between a couple companies. But in both companies, we had a conversation about how we were going to respond to the pandemic, which is we could basically take ourselves out of the game and just huddle in and wait for this to blow over. Or we could look for the unique gift that is buried in here. That only exists for us if we have the opportunity to see it. And in both cases, we ended up basically making some shifts to what we were doing, really leaning into it, rather than running from an empty and a lot of marketing. And in both cases, both businesses just exploded. We were lucky in the positioning like we are the type business that did explode. But also, and we’ve not really talked about EO accelerator, which you mentioned, I was the chair of your accelerator, but it was also my next topic. I was gonna say I was coaching, I was coaching in new accelerator at that time. And so when the pandemic hit, we were six months into my coaching program and my small group. And so we had our first zoom call, because none of us like we’re all trapped at home. Where I’m the coach, and we’ve got six entrepreneurs of different businesses, including businesses that are event businesses that are completely like they what they believe their business is does not exist anymore.

John Corcoran 43:16

Yeah, I’m on it. And we haven’t tried to completely pivot or else they do nothing for two years.

Craig Swanson 43:21

Yeah. And basically, my, my challenge was, I offered three kind of like concepts for them just talk about first of all, like, how’s your family? How’s everyone doing? Like, how’s the health? Like, where are we? Is there anything you need to do just to cover yourself? Number two, are there any hard decisions that are long term decisions in your business you’ve been putting off, because there’s a saying, like, never waste a crisis. Like we’re in the middle of a crisis, this is the time that you can make a bunch of really, really hard decisions that are going to just basically be like, swept away emotionally by everything else is happening right now. So like, if there’s a long term thing you’ve been in denial about, this may be the time to look at it. And then number three, is there a unique opportunity in this circumstance that you have not been seeing because of fear?

John Corcoran 44:09

Yeah. And I have to say so Entrepreneurs’ Organization, which is the parent organization of the Accelerator program, such an amazing organization during that crisis, I think it’s like a template for what to do, because every day I’m receiving and I was an Accelerator program, the beginning of the pandemic. They’re sending a text message and email have a litany of different online educational activities, that we’re educating people about things to do marketing ideas, how to do the PPP things like that. And it was just amazing to see people step it up and help one another.

Craig Swanson 44:44

Absolutely. And one company in particular, like one company in the small group coaching is a event business basically she did audio visual for hotels. Well, in the pandemic audio visual for hotels. Her business went from almost to qualifying almost a million dollars a year to zero in a month. I mean, she had hundreds of 1000s of dollars of cancellations. All in this in this in this what she was dealing with. And she pivoted she has impresses me like very few entrepreneurs I have met like she took a step back and look at okay, what do I have? I have crew, I have cars, I have logistics. And she basically called up food companies that were like delivering to people that are nowadays like reworked for home. And she basically re pivoted her entire company to provide emergency food and delivery services, or like basically utilizing what she’s got. And then at the same time was building out a studio in what was once your storage space to try to create some type of online space for charities or other people to be able to do events and try to get to some semblance of business. So and even best she did this for two years. She became EO qualified at the beginning of this year, and she is now in EO Member in my forum. So she has now my forum, in my forum. That’s and that’s just extraordinary. And there’s other stories like that like, like, there were so many people that struggled, but also so many people that basically respond to try to figure out something. And there’s nothing like having a group of fellow entrepreneurs, some succeeding some like, but all being honest and pulling for each other and like creating the sense that we can choose how we’re going to respond to this crisis and how we can navigate it.

John Corcoran 46:39

Right to be deliberate and intentional, rather than to just let it happen to you.

Craig Swanson 46:44

Yeah. And to look for the opportunities. That does not mean denying the crisis. But it also means that there are unique opportunities that do exist in every crisis.

John Corcoran 46:52

Yeah, I mean, Slack is one of those. And that was a failed different startup. And they were meant to go out of business. They’re like, what else can we do? And they had this internal tool that they built, like, well, maybe we should look into that. And it ends up being a huge multibillion dollar company. And lots of examples like that. This has been amazing. Craig, I love talking to you. We’re almost out of time. I love to ask my gratitude question, which is I’m a big fan of gratitude, especially expressing gratitude to peers and contemporaries and mentors and partners who’ve helped you along the way in your journey. Who would you want to shout out publicly?

Craig Swanson 47:24

Wow, there are so many I’m gonna name check a couple like the one that comes to mind for me is Celeste, Celeste Old who was our first producer at CreativeLive who reported to me but took me aside one day and talked to me really straightforwardly about how my behavior was being disruptive for her team and distracting her team for me he will do the work that we have hired them to do and did so in a way that grew trust instead of breaking trust. And I think I Celeste probably gave me more opportunity to learn about myself and grow than any individual I mean, there’s so many individuals I’ve learned from but like I’m gonna just call up Celeste on this one, and she also she taught me what a producer can do she taught me my superheroes but Celeste is my superhero Celeste became the last in there’s this the entrepreneur operating system, there’s this thing called the integrator this vision, she basically taught me what a differently attraction, what a differently skilled person can do if we build trust together. And she takes my vision, and I give her the power to execute with what she knows to execute. CreativeLive would not be a CreativeLive became and I would not be the entrepreneur that I would be if I had not learned from Celeste how I can work with people like Celeste. So it’s not just that Celeste, like did all this for me for CreativeLive and like made an incredible team and grew an incredible team. Celeste taught me how to work better with future producers and that there was this role that could unlock an amazing amount of creativity and creation for me that I didn’t know existed.

John Corcoran 49:19

Greg, I know you’re super passionate about the EO accelerated program in Seattle. So where can people go learn about that? And where can they also go to learn about you connect with you.

Craig Swanson 49:27

So the best way to go if you’re in Seattle, you’re interested in EO Accelerator, go to seattleaccelerator.org. And there is a single page it contains all the summary of that seattleaccelerator.org Best way to connect with me is look for me on LinkedIn or go to craigswanson.org. Is Craig Swanson. not.org not.com don’t own the.com the.org

John Corcoran 49:49

Got to get on top of that. All right. Thank you so much.

Craig Swanson 49:53

Thank you.

Outro 49:54

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