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Future of Work: What Everyone Can Learn from a Bootstrapped Business with Jeremy Clarke

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About the Episode

What does it take to run a business on your own that pulls in over $2 million in revenue per year? A lot of focus, time management, and grit. Jeremy Clarke shares his story of entrepreneurship that started in 8th grade and led him to launch multiple successful businesses. Get the backstory on Formstack Documents, originally called WebMerge, plus insights into how to run a business, why entrepreneurship can be so fulfilling, and how to build the life you want through strategic choices.

Episode Highlights

Meet Our Guest

Is there anything Jeremy Clarke can’t do? From software engineer to entrepreneur, the father, investor, and business owner has accomplished what seems like a lifetime’s worth in just a few decades. He founded WebMerge, now known as Formstack Documents, in 2011 and spent five years building the business all on his own. Once he hit the $2 million revenue mark, he hired his first (and only!) employee. After a successful acquisition by Formstack, Jeremy went on to write the book Bootstrapped to Millions: How I Built a Multi-Million-Dollar Business with No Investors or Employees.

Episode Transcript

Chris Byers: The future of work is being shaped by the advancement of technology and the evolving demands of talent. What changes could be in store for the workplace, the workforce and the nature of work itself? In this season of Ripple Effect, we're continuing our sub series on the future of work, exploring the answers to these questions. I'm Chris Byers, a former SEC. And joining us today is Jeremy Clarke, a father, an investor and entrepreneur. And we'll tell his story in just a second. But welcome to the show.

Jeremy Clarke: Hi, Chris. Thanks for having me.

Chris Byers: So to get us started today, I'll tell you a little bit of a story. Back in 2010, I took my job here at 4pm Stack and I was getting to know the software business is getting to know from Stack. And about a year in, I was looking for a software developer and somewhere along the way I got to meet a guy named Jeremy Clark. And over the course of a little bit of time, we struck up a friendship. And ultimately that kind of meant he joined our team. And what kind of started that way back 10 years ago became something pretty exceptional, a story that I think you're really going to enjoy hearing and hearing how Jeremy's thought about really building a business. So maybe, Jeremy, tell us what happened. And I met 10 years ago. Tell the audience a little bit about that story.

Jeremy Clarke: Yes, I remember meeting you, Chris, at just a tech conference in Minneapolis and just had randomly sat at a table with you and got to talking to you. And from there, just kind of struck up, as you said, kind of a friendship and kind of kept in touch. And then we were talking one day and you had this idea for Form Stack and you were looking for someone to help build out a website and kind of the whole leg of the business. At the time I was working on my own business, I had a Web development business where I had clients all over the country and I would build different websites and applications for them. We got to talking and sounded like a cool opportunity. We started working together on this new application called Form Concierge and it brought me into the form SAC office. I got to meet all the team and from there just really kind of enjoyed that whole process of being in an office environment. And from there, I just really enjoyed working. At 4pm Second that eventually turned into a full time position as an engineer at 4pm Stack.

Chris Byers: Well, I think it's funny you mention I remember those early days and you actually I think you were plenty successful actually in your own business, but just really want to get out of the house and experience being with other people. You tell a story in a book you wrote recently and we'll get into that in just a little bit. But you tell a great story that I don't think I ever heard until I read it. And you talk about how you got started really with your first business. I think people would love to hear kind of what was going on around you then and what got you started.

Jeremy Clarke: When I was in eighth grade, someone came into school. I forget his name, forget kind of his background. But I remember the story in general came in and he talked to us about game development software, building games. And it just really piqued my interest. I wasn't a huge gamer, but like the thought of building things on a computer always interested me in that kind of that interest kind of spiraled into building websites. I self taught how to build my own websites and from there just kind of building my own just fun websites. And at the time I played tennis during my middle school and high school years, and I decided one Christmas break that I was going to build a website for the local tennis club that I played at, and this was two thousand two thousand twenty two thousand one. So it was before a lot of smaller businesses had websites or even thought about them. After I got it done, I took it to the owner of the club and presented it to them and said, I think this would be good for your business. And he really liked the website and asked how much. And I kind of froze. And I was like, I hadn't even thought about it. And I just threw out two hundred and fifty dollars to sounded great to him. So it was a no brainer. He said yes and bought it on the spot. I think we had the website live the next week. That was kind of my first sale of something that I built myself and kind of that kind of piqued my interest in business in general, just like I can really go out and build something myself and sell it like I don't have to go work for somebody else to get a paycheck.

Chris Byers: I think it speaks to something that is clearly a little bit in your DNA. But I think a way that you think about things that maybe other people don't and maybe a way that's not even as complicated as people sometimes make it about how you can just get started because you took something that you really knew probably somebody needed and you could have gone in and you could have pitched it and they could have said, yeah, we'll do it. And then you come back weeks later and you've accomplished the task. But it sounds like there's something pretty valuable. All about here's the here's the thing I'm delivering and it's already done, like you don't have to wait for it. I'm curious if there's something that feels like a way that you think about things that you don't think other people always do.

Jeremy Clarke: When I was in college, I had many other clients, but I had one client from California reach out to me, a person. He wasn't a client yet. A person from California reach out. He had this website and he was having trouble with his developers and he just was looking for someone to take it over. And we had a couple of calls. And at the end he was like, OK, my my developers have promised me that they're going to fix their issues. We're going to get this going. So for now, I'm just going to hold off on kind of making any changes. And I said to him, I was like, well, like, I'd like to just kind of show you what I can do. And so I went out and I built kind of a special project that he was talking about getting done, that he was having trouble with his developers to get done. Over the weekend. I built out this project for him and I showed it to him. It was like, hey, I just did this just to kind of show you what I can do. And he was blown away and like he basically replaced his developers with me that day. And so I think that's another just going above and beyond what people expect and just kind of delivering, as you said, it's already done. It's just like giving them such an easy decision to make. Like they don't have to wait for you to go complete whatever you're discussing. It's it's just they're they're they're ready to buy on the spot. I think there's a ton of value to that.

Chris Byers: I think you're exactly right. Well, take us back to you. I mean, we're talking about the future of work. Back in 2011, you saw a problem as you were working at 4pm Stack that customers were facing and decided to solve it. Talk to us about that.

Jeremy Clarke: So kind of all started with form concierge. And again, that the concept was, we'll take your paper forms and we'll provide a service that automatically converts those into online forums. And then you can start collecting data from your customers through your website rather than emailing them a form, having them printed off and then mail it back to you, whatever that inefficient process is kind of using online forums to really streamline the process. That was all good. Everybody loved that. But one thing that the businesses weren't ready to kind of change was their internal process that they had. Once that data came in, they still wanted that data to be spit out on those paper forms so that they could pass it along to any department within their business that is used to that paper process already. And they can continue their thinking through that. I built a tool that allowed someone to build a template on our system and then it would feed in data from the form to create populate that same paper form that they had a couple of customers that we had really enjoyed that kind of process and that flow. And as I got to know those forms that customers more, I saw a bigger opportunity that this this isn't just for these small subset of customers that we're targeting for form Cáceres forms that cost thousands of customers that are collecting data online and likely are already using some type of paper form process. And this could be beneficial to them as well.

Chris Byers: And so tell us about those early days. You had this idea that turned into really a business that is continuing to grow today. What was that? How did you get it started? And what were those early days like

Jeremy Clarke: with that kind of seeing what I saw working with the form concierge's customers, I decided that there could be a business here. And so I went off and I built the separate product that was called Web Merge. And kind of the name was based off of where its mail merge, but for the web. So a similar concept. So I built out the first early version of that product that solved a specific problem, allowed someone to set up a template within our system, allowed it to connect with a form stack form. And then it would every time a new submission would come in on their form, they would email them a copy of that PDF. So it converts their template to a PDF email, then the document and then inside the document would be the data that they had kind of outlined in the template. And within the first couple of months, I had a handful of users try it out. We were able to do some cross promotion with form stack a couple of blog posts to show people how it was used. And really, it was a slow growth process once I had people signed up. I worked really closely with them, learning about their business, learning about what their paper process or just the reform process in general looks like, and really listening to their feedback to look for new features and ideas to expand the Web search product over time.

Chris Byers: I'm curious, I think for people listening, fast forward just a little bit. There was a time just a couple of years ago in twenty eighteen where full circle formed Stack actually came back into the picture. You had left and gone on to make web merge a super successful business and actually form stack bought the company. And what's fascinating about that is plenty of people who know the back story know that Jeremy and I had many conversations about this. Should this be something formed seconds and way early on? And, you know, in those early days, it wasn't like there was just endless cash coming out of the business. That was kind of a long slog, really, to get to the point where you really knew, like this could be a good profitable business. What were those first years like? Let's say the first couple of

Jeremy Clarke: years it was, as you say, like it was slow growth. We were tripling revenue, but off of small numbers. So you saw the growth there, but it wasn't enough to where I could quit my job and be 100 percent secure in Webers being the future of kind of my livelihood. And so those first couple of years, I really I played it slow. I didn't spend a lot of money to get customers. I really wanted to prove out the business about the product and make sure there really was good product market fit there. So over time, over those first couple of years, I slowly kind of built it up. And eventually after a couple of years, I was making enough money that I could feel comfortable kind of stepping away from form stock and focusing 100 percent of my time on Web search. But it really was kind of a slow process and a lot of nights and weekends. So it's having essentially two jobs. I made sure that form stack was my focus during the day, but at night and weekends, Web search was my entire focus and handling customer emails and product development. I was doing it all.

Chris Byers: One of the stories you talk about in part of the journey really speaks to the fact that you did everything. And I think that's an entrepreneurial journey often. But it's a lot to say that you did all of the marketing, all of the engineering, all of the customer support, all of the just basic business stuff that you have to do. And had you do all that, how did you keep it all together? I think it'd be easy to kind of let a bunch of those things slide.

Jeremy Clarke: Yeah. And I think it is easy to let them slide. And you really have to focus on you have to figure out what matters and what's going to give you the best and results. In the beginning, you know, I had a lot of marketing to do. And if I had special projects, I, I would hire consultants to come in. If I needed to redesign the website, I would hire a consultant to come in and kind of help me do project based work. Bu t a lot of the day to day stuff, it really came down to what's going to have the most impact. If I focus on trying to reach out to 20, 30 new trailers a day, that might take me a couple hours and I might have one conversation a day, which might result in one sale maybe. Or I could focus on the customers that are already have that are having support issues and like they're already paying. I know they're going to convert in really comes down to just figure out what's going to have the biggest impact. And I think it comes back to why I didn't focus a lot on sales and partnerships in the beginning is I just didn't see the value of putting in that time. I didn't think the juice is going to be worth the squeeze for that specific effort. And I think those are just some of the harder decisions that you have to make when you're a team of one is just really finding out what's going to push your business to the next level and just being hyper focused on that. And sometimes stuff falls through the cracks and you just have to make sure it's not something that's going to come back to get you in the end.

Chris Byers: Well, you know, in twenty, twenty one now we're back to that crazy stage of raise a bunch of money. Somehow you can become a billion dollar company overnight. But that does work at times. I'm curious what your advice is to to be the young entrepreneur, somebody thinking about starting a business.

Jeremy Clarke: Yeah, I mean, it really comes down to what type of business do you want to run for me? It was I enjoy running a business, but I also enjoy having flexibility and freedom and being my own boss, not having investors like bootstrapping my own business, like the only people I have to answer to my customers. So as long as they're happy, I'm happy and everybody's good once you start. Taking other people's money to help grow the business, they're always going to be expecting you to grow their investment and so you essentially are working nonstop to make sure you get a return on their money. And so personally, I feel more shackled to the business and where it's just like if I if I want to take an hour off to go do something, I feel like, oh, well, I need to get Johnny's money back. Like, I need to be working harder and harder and harder. And to me, that just wasn't the type of lifestyle that I wanted to lead. So by bootstrapping, I'm able to make sure that I have full control over the business, how it grows, how we spend our money and really kind of focus on what matters. When you're bootstrapping, you don't just throw a bunch of stuff at the wall to see what sticks like. You really do small experiments, see what works, and then pick the big ones, the big successes and really double down on those.

Chris Byers: We have learned a lot, and I'm sure you've had plenty of people reach out over the years to get some advice. You've written a book actually probably for a little bit of that idea. But if somebody did reach out to somebody, an aspiring entrepreneur or whoever. What's the advice you might give them about kind of how to be successful?

Jeremy Clarke: Yeah, I think it comes down to a couple of things. I mean, you have to have a good work ethic. You have to be able to be willing to put in the time that it's going to take. If it was easy to start a business, everybody would do it and everybody would be super successful. And a lot of businesses, unfortunately, fail for many reasons. But I think one of the kind of core aspects is just being willing to have that drive, of being willing to do whatever needs to get done, wear many hats, don't kind of rely on, well, this is not my problem. And somebody else, like, they need to fix it. Even if you have employees and other people, like, be invested in the business and make sure that you kind of know every aspect of what's going on. I think that's one of the biggest things, is just that drive and then just be open to different ideas and not opinions, but just kind of aspects of the business from other people. One thing I've struggled with personally is I have a very I have a mind that I can think of solutions very quickly. And I'm very opinionated and I can be stubborn at times in how confident I am in those solutions and ideas that I have. But I found over the years that someone that comes into your business from an outside perspective, even a customer, investor, whoever it may be, they don't see the business the way you do. They see it the business in a different way. And so if you're able to listen to them, hear them out and frame your ideas around what they're seeing, I think you'll kind of discover a lot of cool opportunities there.

Chris Byers: Jeremy talks about his experiences in entrepreneurship, and it inspired him to publish his first book. It's called Bootstrap Tamilians How I Built a Multimillion Dollar Business with no investors or Employees. Jeremy, what do you want people to walk away from when they read your book?

Jeremy Clarke: I like telling my story. I like people seeing that journey of you don't need to go out and hire a bunch of people to have a successful, even a large business. You can get to millions of dollars in revenue with a small team and really just kind of want people to learn how the different aspects of that business that I think of successful really focusing on the customer being efficient with your time automating as much as possible, really just aspects of the business that I was able to grow it to a large size with having no employees for a number of years and then eventually set up hiring one employee. But as I said at that time, it was it already grown to millions in revenue. And that was kind of a cool journey.

Chris Byers: The things that you think people believe in, it's kind of misconceptions about what it takes to be successful because you've had a mindset that's just different than I think a lot of people adopt. And that is you built a multimillion dollar business and that's like millions of dollars of revenue, real dollars. And you mentioned your first hire, but that was also basically your last hire seat. How'd you do that?

Jeremy Clarke: So when we sold the business to form SAC, it was just two people, me and a friend called Gabe. And from there it was really, you know, as you get that slow growth in their early years, are you focus on just making sure you're delivering a good product to the customers, making sure they have a good experience. And over time, when you're running a business where they're paying you every month and if you're doing a good job, they're going to remain a customer. So over time, your revenue just kind of compounds on top of itself. And before you know it, you have this this large business that it really doesn't take a whole lot of effort to keep a customer. You already have, especially one that's been with you for a while. And so just because you double the number of customers doesn't mean you need to double the number of employees that you have, like you're able to keep up with those customers that. You already have. They can do everything on your own. That's really what was key to kind of allowing farmers to grow and to stay as a team of one for five years. And when I hired Gabe, we were doing almost two million dollars in revenue. And I was it was just me. I was the only employee doing almost two million dollars in revenue. And from there, you just have to really optimize that customer journey so that you give your customers as much control as you can so that they don't need to be constantly reaching out to you for help. And you really just need to scale your time. And if you can do that, you can grow a very large business with very few employees.

Chris Byers: Well, talk to us about that idea around the customer that's clearly important to you. So you've described this idea that you wanted to not be shackled to a business because you've raised money. But funny enough, in a way, you you allow yourself to be shackled to your customers. You are maniacal about customer service. What drives you to say or what kind of motivated you to stay so focused on customers?

Jeremy Clarke: I really just saw good results from working closely with those customers, both from product development. I mean, almost every feature I ever built inside of Web search was because a customer asked for it. I didn't go think of a bunch of ideas, go present it to potential customers, like, would you use this? I waited for a customer to come to me and request something, and if they did, then I would look into it and often, depending on the feature, I would build it as quickly as possible. And really it comes back to just wowing the customer. A lot of times in software, especially a larger business, like you asked for a feature, it might be months, it might be a year before something gets built, if ever. And I think if I could talk to a customer on Monday and have a feature ready for them on a Wednesday like that blew them away. And I think they were super impressed by that. And it created a loyal customer and I had really good relationships with them. And so over time, I really just kind of took that customer centric focus and just maximized it. How else could I while the customer and one of my biggest reasons for success was our customer support, we would respond as quickly as possible. So if I got an email and I knew a quick answer, like I would send them a quick answer back as soon as possible. Sometimes it was within minutes. So they were extremely surprised by that, that fast response. And I was able to build a lot of trust from the customers using that kind of I'm always there for them. Whenever they need us reach out. We'll be more than happy to help.

Chris Byers: Well, having dealt with many of those same customers, Jeremy, your name came up all the time. I'm here because of Jeremy. He made me successful one night in the middle of the night because I was trying to get a proposal built and what merge or whatever it happened to be. I'm sure you decided to write a book and assemble some of the story together. What kind of made you want to write about it and what do you talk about in there?

Jeremy Clarke: Over the years? As I was building Web merge, I, I would think back and I was like, I really wish I would have started some type of blog or something to kind of document the process of building web merge, just kind of like here. The problems running into here is how we solved it just over the time, just kind of talking about Web merging the growth. And for one reason or another, I never ended up doing it and never started it. And so after acquisition, it just decided, OK, that was a good and a good ending to the story. So what if I go back and retell the whole story and have a frame of both the story of what merge in general, but then also like what aspects of that story do I think contributed to his success and really highlighting the different areas of the business that I think were most valuable in kind of getting to that exit that we kind of got to it. Twenty, eighteen.

Chris Byers: What are some problems that you still see in the world that you think this really needs to get solved in the next couple of years?

Jeremy Clarke: I still see just a lot of there's a lot of opportunity for software. There's just even after twenty twenty everybody going digital overnight. I still see there's just a lot of wasted time, a lot of wasted time in business and or just in processes like I forget who we just got. I have a two and a half year old daughter and she's going to be going to school next year. And I, I found a piece of paper that my wife printed off yesterday, and it was an application to the school. Still, like we have to print off this application. We have to fill it all out. We have to mail them the deposit check. It just seems like entirely inefficient where they could just have a simple application on their website with a credit card form like the DONE. It just amazes me the inefficiencies and that's just the form paper world and I think it's 20, 20 has pushed a lot of businesses to rethink how how they do their own work and how they can make those processes better. But there's still a lot of inefficiency out there.

Chris Byers: Well, as we wrap up, I've got just a handful of questions to kind of bring it to a close. One is really just what do you think the number one soft skill is that people need in this new world that we live in?

Jeremy Clarke: I think the biggest skill is just time management, learning to where you are most productive throughout your day. If you're spending four hours a day working on the same repetitive project over and over again. Is there a way to automate it? Is there a way to cut that down to two hours? I think people a lot of times get stuck in a rut of where they work for the sake of working like they work 10 hours a day and 12 hours a day because they think that's what makes you successful is working a lot of hours and it's more on the results and how efficient you are in that workday. And so I think that's what I learned over time, is just better time management skills and focusing on things that matter.

Chris Byers: And as we look to, let's say, 20, 25, 20, 30, what's something you hope is true about the future of work in the future of technology?

Jeremy Clarke: I am a 20 30. I really hope that I never have to leave my house again to do anything business related. Everything is shipped to my house, which we're pretty close. But yeah, I think fruiterer workwise, you have interesting opportunity in this digitize workplace thing that's going on right now and it'd be interesting to see how that changes for business in general over the next couple of years as people start to think about going back to work, like what's that going to look like? And so are people going to be really just flexible, be able to live from anywhere or work from anywhere? I think it's going to open the world up to just full opportunities.

Chris Byers: Well, thank you for joining us today on this special episode of Ripple Effect on the Future of Work, to learn more about how people are reimagining their world of work. Head over to Forward practically dash genius, also linked in our show notes.

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Practically Genius is a show built for innovators championing digitization within their organization.

Hosts Lindsay McGuire and Ryan Greives host conversations with real-world innovators sharing stories of digital transformation while also providing helpful advice and insights to listeners.

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