Craig Swanson is a serial entrepreneur and business coach, best known as the Co-founder of CreativeLive, an online learning platform. Currently, he operates a personal startup studio, launching a new AI project every week. Craig has a track record of partnering with influencers to build successful online education businesses, including collaborations with photographer Sue Bryce and Kaisa Keranen. He is also the chair of the Seattle EO Accelerator program and EO Seattle and loves helping creators, educators, and entrepreneurs build sustainable ventures around their dreams.
Here’s a Glimpse of What You’ll Hear:
- [2:29] Craig Swanson discusses partnering with Sue Bryce to build an online education platform
- [4:28] How the pandemic made online education platforms more valuable and profitable
- [5:22] The process of choosing business partners and why alignment matters
- [9:16] AI’s impact on education and the future of personalized learning
- [13:29] Craig’s journey after selling all his businesses
- [15:27] Why keeping one business for yourself might be the best move
- [17:14] How the EO Accelerator program helps early-stage entrepreneurs scale
- [19:50] Craig highlights the success of Jennifer O’Neal
- [26:27] How to get involved with EO and the power of the entrepreneurial community
In this episode…
Exiting a business can leave entrepreneurs questioning their identity and purpose. After years of building a company, the transition to what comes next is often uncertain and emotionally challenging. How can you navigate the uncharted waters of reinvention and maintain a sense of purpose after selling a company?
Craig Swanson, a seasoned entrepreneur, shares his firsthand experience navigating life after selling multiple businesses. He emphasizes the importance of choosing the right partners, ensuring alignment in vision, and maintaining ownership of at least one venture to sustain personal fulfillment. Craig also discusses how AI transforms online education, making learning more personalized and scalable. By leveraging AI-driven platforms, educators and entrepreneurs can streamline content creation, reach wider audiences, and build sustainable enterprises.
Tune in to this episode of the Smart Business Revolution Podcast as John Corcoran interviews Craig Swanson, an entrepreneur and business coach, about the challenges of exiting a business and finding purpose beyond entrepreneurship. Craig delves into how AI is revolutionizing education, how to choose the right business partners, and why keeping one business for yourself can be a game-changer.
Resources mentioned in this episode:
- John Corcoran on LinkedIn
- Rise25
- Craig Swanson LinkedIn | Website
- EO Seattle Accelerator
- EO Seattle
Special Mention(s):
Related episode(s):
- “Craig Swanson | Building an IT Support Company for Creatives and Scaling Business to Over $1M”
- “EO Portland | How To Get Yourself Out of Running Your Business” with Zac Cramer
Quotable Moments:
- “Selling a business isn’t just a financial decision — it’s an identity shift that forces you to redefine your purpose.”
- “The best partnerships are built on alignment, not just opportunity. Shared vision and trust make businesses succeed.”
- “AI is reshaping education by personalizing learning experiences, making it easier for people to absorb knowledge in a way that suits them.”
- “If I could do it again, I’d always keep one business for myself — it’s harder than I expected to start over.”
- “Entrepreneurial success isn’t just about making money; it’s about creating something meaningful that outlives you and continues to impact others.”
Action Steps:
- Build strategic partnerships: To achieve success in scaling a business, consider collaborating with partners who bring complementary strengths.
- Embrace online education platforms: Investing in building or improving online education platforms can significantly increase business value.
- Leverage AI in learning: Explore the integration of AI to personalize and enhance learning experiences, making education more accessible and effective.
- Participate in entrepreneurial communities: Joining networks like the Entrepreneurs’ Organization (EO) can provide invaluable support, learning, and networking opportunities.
- Reflect and plan post-exit strategies: For entrepreneurs who have exited their businesses, taking time to reflect on their identity and future goals is crucial.
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Episode Transcript
John Corcoran: 00:00
All right. Today we’re talking about what do you do if you identify as an entrepreneur and you’ve exited your business? What happens to your identity? My guest today is Craig Swanson. He’s been on the podcast before. I’ll tell you more about him in a second, so stay tuned.
Intro: 00:16
Welcome to the Smart Business Revolution Podcast, where we feature top entrepreneurs, business leaders, and thought leaders and ask them how they built key relationships to get where they are today. Now let’s get started with the show.
John Corcoran: 00:32
Welcome, everyone. John Corcoran here. And you know, if you’ve listened before, every week we have interesting and smart CEOs, founders and entrepreneurs from all kinds of companies. We’ve had Netflix, Grubhub, Redfin, Gusto, Kinkos, YPO, EO, Activision Blizzard. Check out the archives. Lots of great episodes in there. And of course, this episode is brought to you by Rise25, our company where we help B2B businesses to get clients referrals and strategic partnerships with done-for-you podcasts and content marketing. And you can learn more at Rise25.com and learn about our new podcast Copilot platform by checking that out.
And I want to give a quick shout out to an organization that helped bring this podcast together. It’s EO Seattle. EO Seattle is the local chapter in Entrepreneurs Organization, which is a global peer to peer network of more than 18,000 influential business owners with 200 chapters across 60 or so countries. So if you were the founder, co-founder, owner or controlling shareholder of a company that generates over $1 million a year in revenues and want to connect with other like minded successful entrepreneurs, go check it out. EO Seattle is the chapter for you if you live in the Seattle area.
All right. My guest here today is Craig Swanson. He is a long time entrepreneur, started a number of different companies, including CreativeLive, which you may know, and he’s excited a number of different companies as well, including his personal startup studio, where he partnered with other companies that had online brands, wanted to build online businesses and helped build them up, and has also sold a Sold a number of those. And so Craig, so excited to have you here today.
First of all, let’s dive into your background. Now we’ve done previous interviews where we talked about CreativeLive. And then you had started partnering with other brands, people that had a following but maybe hadn’t monetized it enough, hadn’t created enough of a business behind that. And one of those you did that with was Sue Bryce, who’s a photographer. Talk a little bit about what you guys did together, how she came to you and what she was looking for when she partnered with you.
Craig Swanson: 02:29
Okay. That’s great. So Sue Bryce was a friend of mine and someone I’d worked with at Creativelive for years. Since around 2010. And about 2015, she spun off her own dedicated education platform called Sue Bryce Education. Got it to a certain level and really was looking at how she could really take this thing and just supercharge it. And she at that time, I had exited CreativeLive. I was working on some other projects, and then she invited me to come in, along with two other partners to basically help her build that business. And that’s kind of the role I played for the last seven years after Creative Live, which is basically partnering with instructors that have a significant following, a lot of expertise to share.
So we basically built out an entire education platform for her around her portrait photography business, expanded out to conferences, expanded out to actually creating an entirely separate platform called the Portrait Masters, which was for other photographers to teach on and really just like built that up over the course of the next 4 or 5 years. And then in 2020, during the pandemic, we we accepted an offer for it to be to be acquired as being acquired by one of the largest trade show companies in the United States that had a large photography division that they were looking at at at bringing in content that wasn’t tied to physical people in physical conferences.
John Corcoran: 04:07
Definitely an acute need at that moment in time. Exactly, exactly. Yeah.
Craig Swanson: 04:11
Side note they had pandemic insurance, which is one of the reasons why they were able to fund a lot of these acquisitions.
John Corcoran: 04:17
So that’s probably unusual for many conference companies.
Craig Swanson: 04:21
It was there that some VP years ago made that choice and really saved the company.
John Corcoran: 04:28
Wow. Wow. But I want to put money on that guy. Whoever it was. Like, there might be a global pandemic one day. And everyone else was like, what a waste of time. But go ahead, Fred. Exactly. Yeah.
Craig Swanson: 04:37
And I think that that deal closed in 2021. And just overall, that kind of like that whole arching thing. I think we basically made all these online education platforms I’ve been building over the years two things a lot more valuable. And so we made a lot of money during the During the pandemic and all those assets became more valuable. We ended up selling them off one at a time, largely driven by the. The stakeholder was the lead person in each company. Because we’re basically building around an individual influencer brand.
John Corcoran: 05:09
Right, right. And talk to me a little bit about how you decided who to partner with, because that’s a big decision. You weren’t being hired as these weren’t clients of yours, you were actually partnering with them. So it seems like a bigger, more weighty decision.
Craig Swanson: 05:23
Exactly. I mean, so the way we worked it is, I mean, technically, that’s one of the things I’m personally struggling with is I’ve never been a horrible person. So I wasn’t looking for clients. I was looking for business partners. And so I actually would come in with a team and money and we would help build them something together, and we’d own what we built together as a unit. They often basically controlled their brand, their name. They basically were kind of the visionary and driver of that particular thing. And then we were building out all the tools and all the execution and all the marketing and all the scaling and entrepreneurial stuff underneath the hood.
John Corcoran: 05:55
Yeah. And so you make that decision. And then what about the decision to exit was, is that hard to come to terms with that. Like is that like a joint decision that you made with each of the different partners?
Craig Swanson: 06:07
Pretty much everybody. So each partner gets to kind of decide. So like Sue Bryce Sue is in control of her brand, her name, her identity. And when we were looking at them we were looking at all the opportunities. We were looking at the offers that were being made. Ultimately, it was her choice, ultimately. She’s the one that gets to control the destiny of her name and everything else that she’s built. And once she decided that she was ready to hand off this photography side of her business to someone to acquire it, we basically helped make all that happen.
John Corcoran: 06:37
Yeah. And. Sorry. Go ahead.
Craig Swanson: 06:40
No. And I was just going to say that she is continuing and building education in other areas. The photography side is now owned by Emerald, which is the name of the company. And she is still a part of that. But it’s now being run by a different company.
John Corcoran: 06:55
Now you’re a very rare individual who understands how to build really like an online brand, an online business and monetize it. And I can’t tell you how often I talk to, you know, professional services people, business owners that are frustrated with what they’ve been doing. Maybe they’ve been doing it for a long time, they’re sick of clients or something like that. And the grass is always greener. What do you say now to people like that who are saying, oh man, I wish I had that kind of business?
Craig Swanson: 07:26
Well, I mean, so to be really honest, when they pointed out the businesses that I built in the past, they were businesses I built before the pandemic. They were their businesses. I built in different worlds in a different time. One thing that the pandemic did is it educated every single company that had any type of service that was delivered face to face, that if they did not have an ability to do some type of online version of that company, they were at risk of not being relevant. And so I would say that between the years 2020 and 2022, the things I had built over my career became a lot more valuable. But also probably those years, probably the world moved forward a decade or two, and its overall understanding of how to build, monetize and create online platforms. And the competition has really exploded. So I would say in some ways we’ve shifted a little bit from the gold digging days of, of early where, where you were basically.
John Corcoran: 08:28
Gold nuggets everywhere. Exactly.
Craig Swanson: 08:30
So, so so I, I’ve made my career not selling content on how you build online content platforms. I’ve just made my career by creating wealth and communities with people that are really good educators and really good brand leaders.
John Corcoran: 08:47
And you were an early adopter. I mean, really early adopters before people like online education. Why? That’s silly. Like we want to learn in person. So it sounds like what you’re saying is that you feel like it would be a lot more competitive now. Is there like a bleeding edge now? You know, I mean, there’s AI technology, there’s new things coming in. Like there are new areas that you’re excited about or that you look at and say like, that’s kind of the bleeding edge.
Craig Swanson: 09:16
I mean, the bleeding edge for me is AI. So I have definitely been playing with AI for the last 3 or 4 years and really digging into it. And I’ve got this kind of picture of what an AI enhanced learning platform looks like and feels like. So with Creative Live back in 2010, we were playing with online broadcasts. Today we’re doing an online broadcast right now, you and I. I mean, it is incredibly common these days, but in 2010 it was uncommon. It was difficult to do. Everyone was doing postage-sized video stamps or video, postage-sized video.
We were trying to figure out how to do bigger things. There is this world that we are entering into, in which I am able to do translations of learning styles between instructors and learners, and that’s happening a lot. So the kind of the recent projects I’ve been working on, we’ve been able to do with maybe a 1 or 2 person team, what we used to do with a ten-person team, because I am basically able to streamline so much of the creation and organization of what we’re creating.
John Corcoran: 10:27