Latest / Better Together / Building Businesses That Last with Caleb Zimmerman and Katie Sandquist
Transcript
- Shawn Sundsvold: Hey everyone and welcome back to Better Together. This is the podcast that shares the stories, the lessons, and the practical advice from founders and leaders that can help you improve your business. I'm your host, Sean Sunsvold, along with my partner in business and in life, Kelly Sunsvold. Today's guests are people who aren't just building businesses. They're rethinking how they're built. Caleb Zimmerman and Katie Sandquist, our holding company entrepreneurs, focused on what they call building overnight decades. by bringing together the right people, systems, and strategy to accelerate long-term success. They currently lead and invest in ventures like the stable company, Turn Down, and Channel Companion. All these are designed to help businesses grow with intention in today's rapidly evolving landscape. Now, before this chapter, they spent years in the SaaS world, helping build and scale multiple bootstrap companies to successful exits. But along the way, Caleb and Katie saw a pattern. great companies being built only to lose what made them special after acquisition. That experience shaped a new vision, building companies designed to last, not just sell. Now they apply that philosophy in the AI era, partnering with founders, business building systems at scale and creating businesses that prioritize both performance and people. Their simple motto, we build businesses that allow people to have the freedom to do meaningful work. So, Caleb and Katie, welcome to today's show. Katie Sandquist: Hi, thanks for having us. Caleb Zimmermann: I don't think so. Shawn Sundsvold: Yeah, I was really excited to have both of you here. I think when there's a couple more people involved, it always makes for really fun conversation, right? To get different perspectives of what happens and how person views a founding story is different than another person views it and the different challenges. So I'm really excited to dig that with you guys today. So ⁓ let's start where you are at right now. Give us a quick snapshot of... You know, the three different companies that you've got, stable company, turndown, and channel companion. Tell us kind of in a brief two minute thing how they all fit together. Caleb Zimmermann: Yeah, so we exited kind of last software company that Katie and I were part of in 2023. And I kind of went on this journey of self discovery. Katie moved to New York and we said like, okay, what does this look like to do business differently? And so really like all of these things have evolved out of just our desire of. building companies that we can free people to do meaningful work. So Turn Down is our media company. I have a really talented business partner who runs that, where help businesses their story on YouTube. ⁓ Boring B2B that maybe wouldn't otherwise think of YouTube other than like Mr. Beast, how do they tell their story? And so ⁓ that's what do at Turn Down. The channel companion is a really cool tech venture that we're working on right now, where we partnered with someone who's got deep expertise in an industry, but needed help kind bringing technology to life and so he partnered with us to kind of really come around that and build that. And then really at the center of all of these is the stable company and the stable company is kind of what we call like our forever company that all our favorite people that we love to work with that we never want to not work with again if they want to lure them in and we ⁓ them to stick around but the stable company is how we're I think really building this philosophy and this mindset. So I'll let Katie dig into it a little bit more, but it's been an evolving strategy over the last couple of years, especially as AI is just continually reinventing the game. It feels like every other month. so as tech people at heart, that's been something we've been really paying attention to. But yeah, that's like the very quick kind of overview of where we've been. I think Katie can share a little bit more on the just kind of the stable company, because she's actually leading that company as the CEO. Katie Sandquist: Yeah. So at the Stable Company, we're really passionate about taking all that we've learned from the different business experiences that we've had and truly seeing work be done differently. Being a place where people can understand their gifts and talents and every day get to bring those in meaningful ways and see how they can partner together with other people who have different gifts and talents to be formed as a team to accomplish something special. And we love to see that unlocked not only in our business, but in other businesses. So like, said because we have a history in technology we love to use technology in ways that are very strategic to help people be freed up to do better and more meaningful work that they find deep value in and that helps them to accomplish their goals faster. Kelly Sundsvold: That's great. Thank you for sharing all that background story that ⁓ it's really awesome to see entrepreneurs able to ⁓ those experiences so that we're not alone. We know we're not alone. All right. You've described yourself, both of you, as building overnight decades. What does that actually look like in practice today? Caleb Zimmermann: I think it's, so we came up, we kind of coined that term because I think we all get tired of seeing people, whether it's LinkedIn or. X or wherever, where it just seems like, this thing just like blew up out of nowhere. and you kind of get this like overnight success. ⁓ and so it's a bit of the, it's a bit of the double entendre of like an overnight decade is it, there's a decade of work that's gone into every overnight success. I think even like Instagram, you know, like the, I built this podcast, think Instagram is maybe the only one that truly like they backed into something that just blew up in like a year. They sold it for a billion dollars. but most companies there's 10 years of or more. Kelly Sundsvold: Yes. Caleb Zimmermann: that go into that. And so I know that was our experience, just that there was like 15, 20 years of toil. My loves to tell the story of how he remembers mowing the lawn and me following along behind him with my little bubble lawnmower as he was dreaming about all these things and what he was gonna build. then, ⁓ know, years later I was working with him in the business ⁓ and just would reflect often on how like crazy that was that like, hey, he could not never have dreamed in his wildest dreams that like we would have been working together still in the same tech company. And so building overnight decades is just a fun way of honoring the work that it takes to build business and that ⁓ it's and years years compounded and half of the battle is just sticking in the game and not trying to ⁓ just hit home run every time. You ⁓ gotta have long mindset in the way that you think about these things. ⁓ Shawn Sundsvold: Definitely. Definitely. up, my dad was an entrepreneur as well. He was a stockbroker, but he had his own office and he did a lot with that. And so ⁓ kind of got that bug myself, watching him ⁓ life and do that. So ⁓ some relatable pieces to that and watching it. How do you watch a parent do that? And I was never involved in that, but ⁓ kind of set that stage for me in owning my own business. So kind of looking back a little bit and taking a step backwards, Caleb Zimmermann: Mm-hmm. Shawn Sundsvold: not just running one company, right? You've got multiple companies that you both are involved in, you know, in this structure. So how do you guys think about that structurally and that, you know, you've got multiple companies you're managing and leading. How do you kind of keep up with that and keep it all organized? Caleb Zimmermann: and talk about our operating system, Katie. Katie Sandquist: Sure. So early on, even back, like Caleb said, his father was a serial entrepreneur, a visionary, if you will, on steroids in a lot of ways. He always had a really cool idea and always a new business. And so I would say it was 2013 and I was helping run with a group of people two businesses that him and his business partner had started. And we were having this chaos effect. Every day was something new. They would come in and this client's on fire, you need to go solve this. The next day, we should be doing this. The software needs to take this turn, so get somebody on it right now. Hey, now we have cash flow, so go find me cash. Every day was something new. And so me and two of the other people in those businesses had gotten together and said, we've got to figure something out. We have to find some way. through a process of exploration, found an operating system. There's lots of them out there. found one that worked for us and at its core operating systems just help give you almost a bone structure for your body of people to do your body of work. ⁓ that operating system in place, we're able to ⁓ approach the chaos with a framework to help us place it in the right bucket, if you will, and everyone aligned and focused on mission. So when an urgent item came up, the urgent didn't to replace the important. We had a place to put it. had something, structures and rhythms of meetings to work through those items and decide, does this truly need to replace the important because it's a higher value? ⁓ it something that can wait another 90 days till we can come up with a new strategy and plan ⁓ ensure that you keep a group of people together? ⁓ as we grew eventually to then three businesses and almost 100 team members, To keep everyone organized and aligned with three different missions all headed towards one single arc of caring about care, you have to have intentionality putting people to work and helping them see the bigger picture and that their work is meaningful. So today we take that forward with us into our different business ventures. ⁓ think about the overarching value of building these that last decades and freeing people Shawn Sundsvold: Yeah. Katie Sandquist: people up for meaningful work. How do we do that with different ventures? And then we keep very focused with that group and that business. So anytime we go into what we call our weekly team meetings, we're keeping that vision and mission of that particular venture very focused. And we have structures of types of meetings and how we think about that work that crosses all of those different businesses. So we're able to keep ourselves focused when we shift our focus to different businesses. And we're able to then keep on top of the work and keep the world moving. Shawn Sundsvold: Okay. Caleb Zimmermann: I think it's one of the hardest things right now. I bet a lot of other entrepreneurs are feeling this, especially if you're working on multiple projects or your vibe code and stuff at night is like you're constantly context switching even jumping from like call to call. You know, I'm sure you guys feel like you jump from a podcast to a client meeting to this. All of a sudden, you know, you, gotta go to a doctor's appointment in middle of the day. like, how do I like keep my head ⁓ and keep it screwed on? Right. And so we try to do a lot to just help ourselves like both by like recording all of our meetings. upload those. Shawn Sundsvold: Yeah. Caleb Zimmermann: transcripts, we actually have a tool that we're building right now for ourselves that we're eventually going to start letting other companies use, but that essentially just takes your transcripts and turns it all into like, this is your operating system. Here's what you need to discuss. Here's what you need to focus on. And so it's like, it's just out in front of you thinking for you, cause there's like so much of a mental load now that it's really easy to get overwhelmed with that. Shawn Sundsvold: Yeah, yeah, definitely. Kelly Sundsvold: Yeah, the jumping is definitely a reality. In fact, right after this call, I have a doctor's appointment and then we jump into another meeting and it's reality, it's comical, but again, like so relatable. You you touch a little bit on how like you balance building new ventures while still growing. Caleb Zimmermann: Yeah. ⁓ Kelly Sundsvold: and supporting the ones you already have in motion, ⁓ the, ⁓ was the transcript tool that you talked about, like ⁓ you were developing. What are other ways that you guys are balancing building those new ventures while you're still supporting the ones that are already in motion? Caleb Zimmermann: you have to have really good people around you, which has probably been my focus. think my role is kind of unique and I get to sit in this weird spot of like, kind of sit in all of the teams. And so I think the thing I'm super fortunate to have is just like really talented operators and business partners in each of those places. And so I think it's a pitfall that I see, or maybe not a pitfall, it's a choice that some business owners make right now in the tech world. like, they just want to grow. own skill. with as few people as possible because managing people is like, it's people are going to people. It's, tough, you know, and like we, had, you know, the last company was our biggest. had scaled to like 65 people in just that one business. And, you know, I had a team of like 25 and like that, that's a lot of people to figure out and to manage, but, maybe I'm weird, but like, I love ⁓ actually to figure out how do I hire ⁓ as people as possible? because I think it's so fun because I think every person is this unique skillset that they bring. And so. ⁓ I think that's one of the things we're particularly good at just in our businesses is like finding the right people, figuring out how they fit in and how does one plus one equal 10 when you combine the right mix of people. so without, ⁓ I could go into specifics on that, but like that truly is it, is that it's like we have really incredible people that we work with that make it easy to do that. ⁓ Katie Sandquist: Well, and would say, would you add we invest the time to understand each other and to utilize the strengths that each person has. So we're not trying to do something that's outside of our wheelhouse or our gifting that would be and they find joy in it. Why would I take that if that's something they're great at and they love it? Shawn Sundsvold: Yeah, I think. Yeah, that process is so hard too, because bring somebody into a role, right? And they get started and sometimes maybe they're not quite the right match, right? Like maybe they're in 70 % towards the skill set, but ⁓ it becomes a question, can we find a better seat for them ⁓ the company to do things? ⁓ And of the things on that is like you mentioned that ⁓ really you're doing now, you're building forever companies instead of exiting, right? How does building a company that way shift the way you're making day-to-day decisions? Caleb Zimmermann: would you answer that Katie? I have strong opinions on that, but how would you answer that? Katie Sandquist: I would say it effects. It deeply affects the decisions you're making and how you align people to the ultimate vision and mission. You're, you know, one of the things we practice is always keeping a vision board out in front of you, a picture of what you want it to look like in the future so that when you sit down and you're actually making decisions, it's right in front of your face to say, does this support what we said we wanted to do? Are we taking action with intention to the North Star that we have out there? can we keep integrity with our people ⁓ we say this is the decision we've made and they hold us accountable to this is what you said we were heading towards, this is what we believed we were building. ⁓ I think if you have that mindset, you're taking decisions like a downturn in revenue. ⁓ The choices you make during that time really show, are you committed to that vision? Are you staying with it or not? And it can get really easy to get distracted if don't keep that vision and north star in front of you. It can really tempting to take the short win. Our experiences with some of the firms that acquired our previous companies. Shawn Sundsvold: Yeah. Katie Sandquist: really helped us to see the difference when we were making decisions to help our people in investing in what they were great at and helping them. Like you said, maybe they came in for one role and there were 70 % of it they loved and were great at. The long-term goal is showing them how can we be invested in building skills and knowledge to get them more and more into their seat of what they love and they're great at and finding other people to take the things they don't love and they're not great at and building a all around that and investing in that person who's different. One of my favorite stories is Caleb was running a team and we had to build these forms. And he's like, ⁓ just like who would even ever want to do this? I was like, game on. There are people out there. We're going to find them. And we did. And we ended up with a team of eight people who, that's all they did all day long, and they loved it. so the long-term approach invests in people, finds the person that loves that, helps them to continue to grow in their gifts and their talents, and gives them skill and knowledge around that. Versus some of the things we saw where you prioritize the short-term win, cutting people because it matters to your bottom line and a story you want to tell investors. That's a very Shawn Sundsvold: Okay. Katie Sandquist: approach. Caleb Zimmermann: Yeah, the quick way I always explain it to people is I learned the difference between no money, no mission and money is the mission. And because no money, no mission is you're not a business if you're not profitable. Like that is a tool that you should be using to support the mission of where we're trying to go versus money is the mission. It's just you're making all your decisions around making money, which wouldn't argue is inherently bad. It's just a very different philosophy of how to run businesses. And we just happen to be persuaded that we love to build for the vision in the long term because we just think it's Shawn Sundsvold: Mm. Caleb Zimmermann: better for people. Kelly Sundsvold: Yeah, definitely. So kind of shifting a little bit and talking about entrepreneurship kind of as a whole. What's been some of the hardest lessons that you've learned as an entrepreneur? Caleb Zimmermann: Hmm. Gosh, nothing happens as fast as you want it to. You you have these vision sessions and you get super excited and you're like, all right, here we go. And then you just go back to, you know, staring at your computer, trying to make it happen. I think that's, you know, we can have these really fun grand ideas and we're still very much in the infancy of what we're building. ⁓ You know, there's like. five of us who have all kind of committed to each other that we're in this thing for the long haul. And then we have a handful of other people that work with us full-time and in other kind of like contracting capacity. like we've got a lot of momentum, we've built a lot of cool stuff and yet it's still a grind. ⁓ it's, think there's that element of like, know, again, it's not overnight successes. It takes a lot of work. even with all the incredible experience and talent that we have, it's just, It's a lot of work ⁓ I think a lot of people getting into entrepreneurship don't understand that right away. Shawn Sundsvold: Yeah. Katie Sandquist: I think I would say it too, just the curiosity element. Entrepreneurship takes a lot of curiosity. What did I learn from that? What can I take from that and move forward? There's a lot of pivoting, feel fast. So the more you can stay curious about what other people are doing, what problems could we solve, what really resonated with others, how might we learn from that venture, kill it, and try something different? Shawn Sundsvold: Mm-hmm. Katie Sandquist: And I think that's where it truly starts to stick. One of the things I loved about our businesses that we've built in the past the people would say, I don't care if we switched ⁓ we're doing. I just love this team. And so the strength you can build in the people that are around you to be resilient and that, curious collaboration to continue to search and grow and learn. ⁓ think that's, are truly the entrepreneurs who end up thriving. Shawn Sundsvold: Yeah. I'm curious, you know, because you guys have been around multiple businesses and, know, done this process, like, you know, three, four times now at least. And every business is different, but is there like a magic number where once you guys got to like three years, four years, five years, eight years in a business where you felt that process get easier versus like, you know, at the beginning you're it's just you or maybe a small team and every day is a grind, right? But there comes a point I think where you start see it starts feeling different, right? Because you've got a little bit more establishment, you've got a little more knowledge on your team. Do you see like a magic number for businesses like that or kind of a certain growth point that really starts to make a difference? Caleb Zimmermann: I would, my quick rule of thumb is 18 months that it takes because it takes about a year for you to just figure out what the heck you're doing and get your name out there and get in front of the right people. And then there's another six months for the people you talked to a year ago to come back and be like, Hey, you're still doing that thing. I need it now. Cause I think that's, that's the other thing is you think you go start this incredible thing, but not everyone needs your, they don't need the solution to that problem. Like right in that moment. And so I think that's like, that 18 month, from like a time standpoint, if you can stay in it that long, you'll have a pretty good sense of like, this is gonna work or not gonna work. But that would be with the giant asterisks of like, but if you're doing the wrong thing and it's not gonna work, then you should have kind of gates that you're like, how quickly can we make this thing fail and find out if it's right or wrong? Because you can waste a lot of time just grinding on something that no one's ever gonna pay you a meaningful amount of money for. but 18 months is my quick rule of thumb. Shawn Sundsvold: Yeah. Katie Sandquist: And I would just say as an entrepreneur, there's different stages of your business growth, much like a child has stages of development. And there's different things that become easier. And then there are different things that become harder. So in the beginning, really finding your place, finding your product or service. Caleb Zimmermann: or just Katie Sandquist: to get to the right people at the right amount can be really challenging. As you add people, there's different elements of even just social structure and communication that can get really challenging as you grow beyond three people. You hit that five to seven. Now you have to learn new communication structures and making sure you're not stepping on toes. And then you can get to that 15 to 20. And then once you really get to that 50 mark, now you're in a whole different social space. necessarily know you as an owner as closely anymore. So there's just different things that become easier and different things that become harder. Kelly Sundsvold: Yeah, first, so we have a lot of business owners, entrepreneurs, people starting out, people really experienced listening to this podcast and as our audience. For someone who's just starting out, what do you think they're over-complicating right now? Caleb Zimmermann: Hmm. I think you can spend a lot of time. ⁓ know, sharpening the ax is how I've heard someone else talk about it, but like, can spend a lot of time sharpening the ax versus just chopping trees down, which is like, just get out and sell and talk about it. And I think that is, mean, I've even relearned this in the last ⁓ months is like, I can spend a lot of time like working with my AI tools that tell me every one of my, of my ideas is incredible. ⁓ but until I get out there and actually ⁓ to people and say like, Hey, would you use this or would you not use this? Do you like that? Do you not like that? Like, I do this or could I do like, that's where all the learning happens. And so you just, you have to get out and talk to people. And if you don't, I think there's very few businesses that are actually successful where you can just sit in your computer and just buy and code it away. And you never have to pick up the phone or hop on a call and actually talk to someone. So even like, I, got the chance to work with, ⁓ West Bush. He runs product led.com, which is a really cool resource. If you're starting, ⁓ kind of in the software space, but he even says like, he's the product lead guy. was like, you're. Kelly Sundsvold: Right. Right. Shawn Sundsvold: Yeah. Caleb Zimmermann: product should sell itself, you shouldn't have to talk to anyone. He's like, but you should talk to your first 100 customers because you're going to learn more in that like first 100 that sets the stage for the rest of it. So you have to pick up the phone and talk to people and it doesn't have, you don't have to have it perfect. People are so gracious. Like if you're just like, Hey, this is like, you know, this is where I'm at right now. I'm looking for feedback or would you, you know, whatever, just like be an open book and people I think really respect that. And if they don't, and there'll be some who get not like this sucks. would never, whatever, just. off the back, you just got to keep going. You got to really thick skin as an entrepreneur, but you just got to get out and talk to people. Shawn Sundsvold: Yeah. Katie Sandquist: Yeah, that process of refining your idea through testing it with others. And you get better about talking about it every time you iterate it to someone new. And I always admired that about my previous visionary. would talk to people. And by time it came back around to me, I was like, whoa, that changed. What happened? Well, I talked to so-and-so who helped me think that through. And then they brought up a good point, right? That idea really gets refined as you talk to more people. the collaborative knowledge of the whole. Shawn Sundsvold: Yeah, Man, wise thoughts. Something curious of too, you know, because we, think we're all in this, right? We've all been ⁓ small business leaders. We've grown businesses to some level. ⁓ For leaders who were, they maybe feel stuck the weeds of their business, right? And I know we've all been there. Where should they start to start getting out of the weeds? Caleb Zimmermann: Hmm. Shawn Sundsvold: And I know that's a hard one because every business is different and every leader is different and how much they're willing to sometimes let go of. But, you know, what are a couple of places that maybe they can start getting out of the weeds and delegating off some information, some, some work. Caleb Zimmermann: I'll just say this is, I mean, this is what Katie is a master at. So I'm gonna defer to her, but this is what she's incredible at. Katie Sandquist: Goodness, okay, so if they're just starting, is that your question? Shawn Sundsvold: It can be like a growing business, right? mean, you when somebody's starting out, it's one thing, but when they're two or three years in and they're still holding on to things that maybe they shouldn't be, where are, what can they do when they're in, how can they start getting out of the weeds in those situations? Katie Sandquist: Hmm. Caleb Zimmermann: imagining that visionary CEO or founder who's got like, you've got a handful of team members, you you're maybe like three to 10 people, but like ⁓ are the linchpin for everything in your business. ⁓ Like that kind of person. Yeah. Shawn Sundsvold: Yeah. Yeah. Katie Sandquist: Yeah. Yeah. OK. I always talk about, first foremost, holding time and space to think about working on the business versus in the business. And you to be very protective. of the time and space, however that looks for you, because different personalities, different flavors need different ways. So ⁓ personally ⁓ going to a coffee shop where there's lots of external background noise, and then I can actually quiet it out and focus in on my own thoughts, which seems counterintuitive to others. So find your space in your place, but you have to protect that to ⁓ about working ⁓ your business. And once you have that perspective and that time away, you have to get real with yourself about what do I love and I'm great at? It brings the most value to the business. And what activities am I holding on to that bring the least amount of value to the business? Who's really great at that? And how can I engage them to begin to take those things on? Sometimes it's a virtual assistant that can be a really easy, great win. who are very disciplined and can take things off of you, but you have to be committed to ⁓ And that could be a whole separate podcast ⁓ or employees and like team members helping them really take that on. And I always preach the apprentice model. So they're going to watch you do the work. They're going to then help you do the work. Then you're going to help them do the work. Then you're going to watch them do the work. Then you need to let go. And during that process, you're teaching them, and then you're coaching them, and then you need to let go. Through that process, they can build the confidence that they're aligned with you in the way that you think about this work and doing this work. You should be building the confidence to have trust in them. too often, I see leaders throw things. They get so fed up. with the work, they can't handle it anymore, they throw it across the fence and then they are confused because it's not happening the way they wanted it to, the expectations aren't being met and then they claw it all back. and you go through this continual, almost seesaw effect back and forth, and then they truly start to ingrain this pattern of, cannot let go because no one else could do it, when in reality it's how we let go of the work that leads to lasting impact. Shawn Sundsvold: Yeah. Kelly Sundsvold: thank you so much ⁓ for taking the time to share your as an entrepreneur and a growing business. How do people find out more about you guys? ⁓ Caleb Zimmermann: You can go to our main website is stableco.io. So hopefully pretty easy to spell and find. So, that's kind of where we share a lot of our... like current thinking and tools and ways to get in contact with us. And then, you know, I'm probably on LinkedIn way too much. So can also go find me by just searching my name. I'm the only Caleb Zimmerman with two ends at the end of his name out there. So you can go find me there. I always, ⁓ I do love to send people hats. So I know if we have video on this or not, but this turndown hat that I'm wearing, I've got about 30 more sitting in my basement. So if anyone wants a cool corduroy hat, that's it's limited out of a hundred. ⁓ It's got whole story to it. So if Kelly Sundsvold: Yeah. Caleb Zimmermann: want one of these, let me know and I'll throw it in the mail to anyone who reaches out to me. Kelly Sundsvold: place. Shawn Sundsvold: Nice. Nice. Kelly Sundsvold: Love it. Well, thank you guys so much, Caleb and Katie. Thank you so much for being a part of this podcast and ⁓ look to staying connected. Caleb Zimmermann: Awesome. Thank you both. Katie Sandquist: you guys. Shawn Sundsvold: Take care.