Life After Exit: Reinventing Yourself as an Entrepreneur With Craig Swanson

So if someone’s a visual learner and someone’s an audio speaker, this is a simple example, but someone’s a visual learner, another person, another person in the class or, you know, group, a cohort or whatever is more of an audio learner. Or if they learn better with a fast talker versus a male versus a female, talking like all those different kinds of nuances could, could, could potentially, as we move forward, could be relevant so that the person, the student that’s learning can learn in the way that they want to learn.

Craig Swanson: 10:56

Absolutely. And we’re seeing some of this coming up. But for example, a lot of instructors, a lot of experts that are not necessarily full time teachers, but they are really strong instructors. And they’re really very, very deep knowledge. The most natural place for a lot of those people to go is a Socratic teaching style with a small group of people. So if you were going to teach a class on podcasting, well, we won’t say you, but, but, but someone that was had a deep expertise, like one of the most natural places for a teacher to go is to basically teach a small group of people between 4 to 10 people and have a rough outline, but teach the class very, very socratically so that as they’re teaching things, people are asking questions.

And there’s this back and forth. Now, that’s a very natural way to teach, but it’s not always the easiest type of content to consume if you’re a learner. If you’re a learner, those side conversations, everything else is kind of going left and right. You get a little bit lost and you’re kind of like losing your main point. But with AI, what is happening increasingly is we can take a an expert that teaches socratically that doesn’t necessarily have a really strong delivery for everything from point A to point B, they do a little bit of Socratic back and forth and use AI to basically interpret that and then reconstitute it into more of a one way endpoint for a, for a learner on the other side of that conversation.

And then and then you can also say break it down into smaller chunks. If you have people that tend to want to learn in smaller chunks, that’s a possibility. It really lets individual learners start to change the way they consume education. And we are just seeing the hints of that right now. But it is increasing every, every couple months.

John Corcoran: 12:51

It’s amazing because, you know, like ten, five, ten years from now, maybe we’ll look back and be like, remember the old way of learning? It was so barbaric. You know, much like, you know, we look back at like 100, 200 years ago, the way that people used to learn back then and think that it, you know, misses the mark and, you know, all the new ways we have of doing it. I want to ask you, though, about though, for you personally, you know, exciting these businesses, you’ve you’ve sold your portfolio. What has it been like for you in this journey, moving from someone who’s been so forward, focused to things, thinking about the future so much to shifting your role and, and, you know, kind of talking about some of the things that you’ve done in the past.

Craig Swanson: 13:29

You know, it. So honestly, it’s been a difficult time. I. I have sold probably six businesses over my career, and I think all six businesses are still running. And each time I sold them, I went through this kind of rebirthing process of loss of identity, trying to figure out who I was. But I’ve also always had a portfolio of businesses. So when I sold Sue Bryce Education, I had other business. I had Kaisa Fit, which was an online fitness company. I had these other companies. But between 2000 and 2022, I actually sold all the companies in my portfolio. So whereas I felt like I understood what that process was, of moving past a company that I’d built and that sense of not being connected to it, I had never done it where I didn’t have another one I was doing on the side.

And so I would say, like the last two years have been, they’ve been joyful and there has been some freedom. And also there’s been a lot of me not knowing what’s next, not really knowing what I’m working on next. And in my role in, in, in the Seattle EO Group and on the board and just different things, I just spend a lot of time now trying to figure out whether I’m in retirement, if I’m in retirement, what that looks like. If I’m not in retirement, what it looks like to not be hitting the type of home runs that I used to hit at what I consider the high point of my career. I’m doing a lot of self questioning and self-reflecting trying to decide what I am without this, without this thing I do, which is building and creating and selling businesses.

John Corcoran: 15:18

And if you look back on it now, is there anything that you wish that you did differently? Maybe you went back to, let’s say, 2019 before you sold the most recent batch of companies?

Craig Swanson: 15:29

I mean, the one thing I’ve told people, there are two there are two things I tell people. There are two things I tell people that I wish I had learned. Number one is if you have multiple businesses, keep one for yourself. Like I don’t think I would ever sell all my businesses again if it were fully up to me. No, no. In these cases, I’m always with partners, so I’m not really sure I had an option of not selling a business, but I didn’t realise how much that mattered to me. And this is, this is silly, but it’s honestly something I was never really a strong self promoter. Take selfies with all the famous people that you work with.

John Corcoran: 16:12

That’s it. I was not expecting that.

Craig Swanson: 16:14

Tip it. It’s one of the things I’ve told other people that that works with a lot of people and, and I never did. I never liked being the guy grabbing my camera and doing a selfie. But I’ll tell you what, if I had a selfie with all the famous people I’ve worked with, it does really simplify the act of explaining you know, why you matter and what you’re doing.

John Corcoran: 16:36

Yeah, yeah, well, my business partner jokes that I like to photoshop myself into photos with famous people over my shoulder here. So, you So, you know, there’s always that. I mean, I think, you know a thing or two about photography, so maybe you.

Craig Swanson: 16:48

Can just stop yourself. I think I could do it just straight with AI. Now, that’s actually a good idea.

John Corcoran: 16:52

Exactly, exactly. It’s problem is solved. Well, I know that your involvement in Seattle has been a big and important role for you, given you some purpose and things like that. And you were really involved as chair of the accelerator program, which I’m a graduate of. Talk a little bit about what that role has played for you as you’ve moved through this kind of life change.

Craig Swanson: 17:13

Well, so first of all, I’ve been an EO now for, I think, coming up on seven years. And EO has just been transformative for me. It is it I feel like I have found my crowd, the people that I felt less weird in EO than I have felt in most places in my life. Just because these are people that are fellow entrepreneurs that deal with the same types of issues that I’ve dealt with in my career. Yeah. And when we were selling our businesses. Lisa McLean, who is the president that year, asked me to step up and be the chair for the EO Accelerator program. And I love the EO Accelerator. EO Accelerator for those that don’t know. EO is for entrepreneurs that are doing that, that are managing a company, owning a company, doing over $1 million a year in turnover.

Accelerator is a program for entrepreneurs that are breaking 250,000, but have not yet figured out how to scale and break $1 million a year. Yeah. And I actually audited the accelerator program the very first year I was in EO. I have been a coach in accelerator for most of my years in EO, which basically meant I was working with a small group of entrepreneurs and helping them work. And leading the accelerator program in Seattle. The two years prior to now, it is probably one of the most enjoyable and tiring experiences I’ve had in, you know, it was a lot of work, especially coming out of the pandemic. But I am incredibly proud of the Seattle EO Accelerator program and the type of difference that’s making in entrepreneurs’ lives.

I, I love that space of of young entrepreneurs in their, in their journey trying to figure out how to get a company that works, trying to figure out how to how they work, their relationship with the business, how they get out of their own way, how they can lean on others, how they can build a team, how they can make the money work. All of these things that sometimes we’re playing with it a little bit higher level in EO because we’ve got bigger businesses. It is so refreshing and enjoyable to like working with people that are in those early stages of making it through that threshold the first time.

John Corcoran: 19:33

Yeah, it helps you remember how much value you can provide to someone like that by helping guide them through something. Talk about some of the examples of folks who’ve been through the accelerator program and graduated from it become members of OEO. I know there’s been a number of them.

Craig Swanson: 19:49

Well, okay, so the EO Accelerator graduate that I know most deeply and I’m most proud of is Jennifer O’Neill. Jennifer O’Neill runs a company in Seattle called Live Oak AV. And they provide AV support for conferences, events, live seminars and three things. Three things about Jennifer. First of all, Jennifer was an accelerator for I think five years. So she was in the accelerator program for five years. I was a coach of hers in an accelerator for about a year, and I was a coach of hers when the pandemic hit. So Jennifer had a business.

John Corcoran: 20:27

That AV company in the pandemic. Woof.

Craig Swanson: 20:30

Exactly. Jennifer went from almost being EO qualified, almost breaking $1 million a year to, I think, having her entire business shut down. Yeah, And she she is just an extraordinary entrepreneur. She pivoted. She was working. She worked so hard to not go out of business. She converted her team into delivering food because she had a team of vans out there. And so she basically just took stock of what she had access to because she no longer had access to her core business. And she figured how she could reinvent those resources to keep herself in business.

John Corcoran: 21:06

I love that, I love that scrappiness when people just are like, okay, what can I do? And they just take it one step at a time and find something new to do.

Craig Swanson: 21:15

She graduated two years after that, so she graduated up into the Big Easy. So she broke $1 million a year, completely reinventing her business, completely redoing everything. She’s now one of my former mates in my EO forum and is the chair for EO Accelerator and is right now leading. I mean, I’m really proud of what we did within the two years that I led the accelerator. The thing that I had the biggest impact on the legacy for the Seattle EO Accelerator is I got Jennifer signed up as my co-chair early. And then we actually brought in an EOS implementer, Zach Kramer, to help lead and coach the accelerator board on how to function well as a board. And between having Jennifer in for a year before she took over, having really great leadership on the board level. That program is just growing and churning along. I just love it.

John Corcoran: 22:15

Cool. Very cool. And I’ve had Zach on the podcast. He’s great. And then talk about some other current accelerator members. I know there’s some interesting ones that are currently in the program.

Craig Swanson: 22:25

So I am still coaching in an accelerator. So I’ve got a whole batch of women that I am coaching in Seattle. I mean, my favorite, my favorite. And she’s given permission for me to talk about her business outside of the accelerator has a company called Bonnie Rae. So Bonnie Raitt catering. And she is an accelerator. She is a Michelin star-rated chef. I don’t really know if that’s the correct term, but she used to. She used to cook in Michelin-starred restaurants.

John Corcoran: 22:52

I think that’s pretty amazing. That’s the Academy Award for food.

Craig Swanson: 22:58

Exactly. And before I think before starting her current business, she was the private chef for the Charles Munger family on their summer holidays. And so she has cooked for Warren Buffett. She’s cooked for Charles Munger. And if you go to her page on her site, there’s an entire list of people that she has cooked for. And she is amazing. And she has cooked for some of the, you know, some incredibly wealthy families.

John Corcoran: 23:25

And hopefully she took selfies with them.

Craig Swanson: 23:27

You know what I don’t know. See that’s that’s that that’s my advice to everybody is like, yeah. So here’s the thing. None of us like doing or there’s certain people that love doing selfies. So yeah, that’s totally she should have taken my advice in prep.

John Corcoran: 23:39

Yeah, yeah. So that’s a great one. And then talk a little bit about I know your role on the board has kind of been you’ve been kind of like an entrepreneur in residence. So it’s kind of like using your expertise and talking a little bit about the EO board and your president, John Pelotonia, I believe is his name. Some of the things that you guys have been working on this year.

Craig Swanson: 23:59

So this year, so this year with the board, with Jennifer O’Neill stepping in to run the accelerator program, I am the EO Learning Chair for Seattle, which means that it’s my responsibility to basically schedule and put on the educational side for the Seattle chapter. And John’s one of John’s big priorities as chapter president this year is creating stronger connections between EO members. So one of the things I did, though, was that I felt it was a little risky or a little different than normal. Normally, we try to fly in a bunch of really big name people to teach at different programs for Seattle this year. I’m really trying to go in, and I was really trying to find instructors and teachers and experts inside the Seattle community that we could basically create a stage for and teach. So we’ve actually been doing a lot more of creating space for our own members to teach for other members. And so pretty much everybody that has taught this year in EO for Seattle has had a really strong connection with you and including yourself. You are coming up. So like you are, I’m super excited.

John Corcoran: 25:13

I’m coming up in January. Yeah, we’re coming.

Craig Swanson: 25:14

Up in January. And there’s actually I think, I think I counted somewhere around 10 or 12 EO members have podcasts right now running that you’ve helped them start and be running. And so yeah.

John Corcoran: 25:28

Yeah. At least that many. Yeah. Yeah.

Craig Swanson: 25:30

And so this really falls in line with what we’re doing for the community, for connection. We’re basically trying to create this space where rather than trying to create really impressive events, we’re trying to create maybe more deeper events, events where we are learning to lean into each other, learn more about each other, and connect with the talent and expertise that is already within the community, either in Seattle or or along this coast.

John Corcoran: 25:55

I think that’s great. I was just having a conversation this morning with another EO member who was we were talking about that power of connection, and I don’t know if it’s because of the pandemic or because we’re all in our digital devices these days, but I think that in-person connection is so important and so valued these days. So I’m glad that you guys are doing that. And that’s really cool. Yeah. Yeah. Well, great. Well, so we’ll wrap it up there. Where can people go to learn more about you, Craig, and learn more about the Seattle chapter?

Craig Swanson: 26:27

Well, for Seattle. Oh, you know what? I don’t know the URL. I think it is seattle.org.

John Corcoran: 26:32

I believe it is Seattle.

Craig Swanson: 26:33

Yeah. Org. and then I’m available at Craigswanson.org. Although come look at EO like EO like if you’re an entrepreneur in the Seattle space or if you are an aspiring entrepreneur. I have not broken a million yet, but looking for that team of people to help you get above it. The accelerator program, something would be really great to look at. Yeah, and all these education things we’re doing, if you know someone that’s an EO like you can find them on LinkedIn. We are also creating space to at least ten spaces in every upcoming education space that we’ve got for creative, for EO this coming year. We are allowing people to bring guests. So if you are interested in what we’re talking about, come find someone that can invite you in and like to be part of this.

John Corcoran: 27:18

That’s great. Craig, thanks so much for your time. Thank you.

Outro: 27:24

Thanks for listening to the Smart Business Revolution Podcast. We’ll see you again next time and be sure to click subscribe to get future episodes.