The Bootstrapped Founder

The willingness to take risks and to gamble with your own money, that already needs a specific mindset that is hard to explain in a way. Hey there. I'm Arvid and this is the Bootstrap Founder. Earlier this week, I came across a quote that resonated deeply with me. I was kinda surprised by it.

The quote was, I can accomplish anything, but I won't really be worthy until I accomplish the next big thing. And this sentiment shared in a hacker news conversation about similarities between founders and their weird self perception, it got me thinking. It got me thinking about the self limiting beliefs that we entrepreneurs often grapple with and especially when we're running solo businesses. There's always some kind of balance to strike. It's never clear cut.

It's always in between something. And as a serial entrepreneur myself, having done this multiple times and experienced more and more of that over time, I've seen this kind of strange cognitive dissonance firsthand. After selling FeedbackPanda back in 2019, a SaaS business that I built for 2 years and then sold to a private equity company, I found myself in a void of purpose because 2 years of work was now somebody else's and with the whole business, which was great to be paid for, my purpose went somewhere else as well, and I couldn't find it. I was gonna lost. And despite joining the small group of people who had successfully sold a business, and I'm always well aware just how few people there are have done this, I felt like a newbie who had to prove himself all over again, but better this time for some reason.

I felt like I had graduated, and now I was the beginner again. And, interestingly, this feeling isn't unique to small scale successes either. I had a conversation with Patrick Campbell who sold his business ProfitWell to Paddle for $200,000,000. I talked to him on the podcast, and that's a record breaking acquisition for Bootstrap Business, let alone for him, like this is generational wealth. And even he could feel it.

He felt that it could have been a fluke that he just got lucky, and he had to do it over again, but bigger this time, which is hard to do if you're already one of the biggest ones out there, but this sentiment of luck is very pervasive in entrepreneurship. This feeling of, I just got lucky or even worse when somebody else tells you, oh, you just got lucky, because it's often used to diminish others' achievements or explain away success by people who just think, they're at the right place at the right time. Big deal. But here's the thing. Entrepreneurship is incredibly complex, and it makes it very difficult to track cause and effect of anything that you do.

Right? It starts with ideation, and it goes all the way to operations. Ideas come at random times, and sometimes the big business idea is is a consequence of 10 other random ideas that happened before that, and sometimes what you do aligns not so well with what people need and sometimes it aligns super well with market conditions, the willingness to take risks and to gamble with your own money that already needs a specific mindset. That is hard to explain in a way because you need this this kind of character in yourself that is both simultaneously optimistic enough to start and realistic enough to keep going. Now you have to kind of curb your optimism once you're in the field and you're trying to sell, you still think every sale of your every attempt at a sale is gonna happen, but you know that most of them will fail, so you need to have this weird balance between being hyper optimistic that this can totally work and then be perfectly fine with the fact that most of it, most of the time will not work.

It will all kinda aggregate into a win in the end, but when you look at it from inside the process, it looks like really, really, really small steps, and small steps that feel like you're not doing anything. Sometimes it feels like you're going backward, and as founders, we kinda challenge oriented people. We love solving puzzles, right, that's one side of it. We wanna just figure it out and get it fixed, but fixing, that's the other side of it because if we just wanted to do puzzles, we would just do Sudoku professionally or play chess or whatever, like, as a professional. That would also be a career, but founders have an additional thing.

We wanna fix it not just for ourselves, but for others. We're building things. We're creating solutions to help others solve similar problems. There's a creative side, right? You have this analytical problem solving side and then you have the turn the solution into something usable by other side, which is a highly creative process, even for developers who think they're hyper analytic, like what you do is creation.

And I think this also requires this delicate balance between being this excellent product person to create a thing and being wildly interested in the underlying often almost theoretical nature of the challenge itself. And I feel this in entrepreneurs who become successful in particular, like, not only do they care to build a really cool thing, like, to build a SaaS that is amazing, that looks cool, that integrates well with other things and it just works, but they are super curious about why things need to be solved. Like my example here is again Patrick Campbell, but Patrick Campbell lives for pricing. This man knows so much about how pricing works, how budgets work, how you can communicate prices, how you should analyze just revenue numbers and turn them into the perfect pricing model. He lives and breathes pricing and he really cares about it and then he also cares about turning all this knowledge, all this insight into a money making and money generating machine.

That's what an entrepreneur is. It's a balance of the analytical and the technical, the technical and the product and the product and the social that you need to have to get marketing on the road and to talk to people through sales, all of this needs to be in a balance. I wanna talk about luck again a little bit because it feels like often the outcome looks very simple and very clear cut, but I think there's also this dissonance within us as founders between acknowledging the role of luck or as I kind of prefer to call it more a contingency, like the random arbitrariness of things and recognizing on the other side that our choices and our curiosity pushes us into the path of that luck, right? Things happen in the world. AI just happened.

Like it wasn't me, I didn't build NVIDIA, I didn't build GPUs that could run these tensor operations or whatever. That technology, I had nothing to do with it, but I'm curious about it and I wanna see what it can do and I wanna then take my understanding of it and turn it into something that other people need help with and through that solve their issues, right? The luck is that it's happening right now, but what I do is be curious and be in the path of what is happening. So when someone dismisses success as being at the right place at the right time I can't help but think yeah sure but they put themselves there, Right? They they followed the trends, they experimented with emerging technologies and they allowed themselves to fail a lot while figuring things out.

And you see there's so much in founders right now. If you look at Twitter just as a as a example here and you look at the path that Peter Levels and Danny Postma have been taking with their own AI centric businesses, you will see that both of them, they are in the communities that are developing the tech. They are actively participating in the process of the technology that is underneath all of the stuff that they're building with the AI businesses. They're curious, they whenever a new version of the AI comes out, they have 2 choices. The first choice is to say, I have just figured out the last version, leave me alone.

I wanna use what I know, I wanna use and make it good. That's that's the choice they have. There's another choice, and that's the one that they take that is saying, cool, what new thing could I build with this new version that is better than the one that was here last year or that is better than the one that was here, like, 2 weeks ago. That is the choice that they make. This is curiosity applied to an idea and a movement towards a goal and as often as financial security or just making a dent in the world, but this curiosity is key and it's part of the balance that we need to strike as founders.

This is the theme, right? That I have in my mind this week is to kind of balancing to very opposing choices, and through this comes adaptability. If we can balance, we will kinda steer clear of the problematic polarizing extremes and find a way through the middle, which is often a zigzagging, I guess, if you wanna speak metaphorically. Sometimes we tend to be more kind of conservative in what we do, we kinda protect the things we already have, and sometimes we're more progressive in experimenting with what's out there. But it's always constant exploration of the field we're in, and there's always experimentation either in a progressive or in a traditional sense.

And I think that is a crucial skill for founders and a crucial paradigm just to understand that that is the way that things almost optimally done. This approach being adaptable, being able to make distinct choices and often opposite choices in quick succession that allows us to navigate this ever changing landscape of market demands and consumer expectations, particularly in fields where the future is uncertain, like anything AI, anything web 3, like even SaaS. We never know where it's gonna go. And most of entrepreneurship is really about striking this balance between long term decisions for the business and short term choices that you need to make today or tomorrow. And I'm experiencing this firsthand with my current project PodScan.

At its core, PodScan is a podcast data platform. It's generating transcripts, it extracts entities and summaries for every podcast out there that is being released, but what I'm actually selling to my customers, at least to most of them, is a product built on top of the platform. It's an alerting and a mention tracking tool. It's Google alerts for podcasts. That's what I kinda call it to make it really clear what it's for.

And I often find myself torn. Again, striking or trying to strike a balance between working on the underlying platform and the customer facing product. Right? The data platform versus the alerting product. Because the platform is complex and super promising.

Right? What things could be built from having access to the text of all podcasts out there, but that is harder to sell. While the product was simpler, it tracks things and alerts you, easier to sell, generates immediate revenue. So short term choices, long term perspective. And balancing this potential of short term sales against this long term promise of building an unparalleled podcast data platform, for me at least, is a constant struggle.

This balancing act extends way beyond just product development. It's about prioritizing my tasks and deciding between cold outreach or improving data quality, 2 very distinct and different things, between spending time with my family and creating the income that sustains them, everything in entrepreneurship and life is about striking a balance. It's kind of about striking a balance anew every single day. And what I've come to realize is that this constant need for balance is kinda unique to entrepreneurship, at least from my own experience being employed, being a freelancer and all of that. When you're not an entrepreneur, most choices are pretty much clear cut.

They're not easy. They're not always completely obvious, but most of the time when other people are involved, they have well defined scopes and outcomes that they want, But as an entrepreneur, the choices that you make today, they will affect your work tomorrow, next month, and even years down the line. And often, the effect tomorrow might be good, but 2 years from now might not be so good or the other way around, it might really suck tomorrow, but in a year, this has just changed everything for the better. Often you don't know which one it's gonna be. And I had a conversation about this with my founder peers in a in a small group and the consensus particularly around PodScan and what it should be was pretty clear.

I'm just gonna share this with you because I thought it was an interesting insight that I myself had not really come to understand this much. What all of them said pretty much was that revenue is king at this point, money matters. Particularly, as I'm still trying to become profitable with the business. And the easiest way to generate revenue while staying aligned with the ultimate goal of the business, you know, in the future should be the priority. Easiest way to generate revenue.

For PodScan, this means focusing on the alerting product for now, even though I know the underlying data platform has much more potential, but I have countless ideas for PodScan and I cannot do them all, right? I want to do trend forecasting and sentiment analysis across different industries, so much more. I have so many ideas and I guess everybody on Twitter has had a couple more ideas that I just added to the list because there's just so much it could be done on all transcripts of all podcasts everywhere in real time too. But for now, I have to remind myself that I'm always striking a balance. I'm committed to building an amazing data platform throughout this process that will eventually be mind blowingly useful for 100 of thousands of people.

I know this is where it's gonna get. But to get there, PodScan will primarily have to be an alerting tool on the outside for now, while still offering API access for those who see the potential in the data once they've looked into the alerting or who find their way through other means into this whole system. And that's the balance that I'm choosing to strike right now. Like I'm making this bargain with myself because I know I need some kind of accountability because everyday I need to make a new choice in the thing that I do and I have to have this lifeline, this kind of goal, that thing aiming at the goal. I don't really know what exactly the goal is, but I need to have a direction here and I need this pragmatic approach to turn POD scan into something profitable enough to eventually pivot into its full potential.

It's not always easy, but that's the nature of entrepreneurship to me. It's a constant balancing act between present needs and future possibilities, And I think that's quite exciting. And that's it for today. Thank you so much for listening to the Bootstrap founder. You can find me on Twitter at Abid Kal, a I v I d k a h l, and you'll find my books in my Twitter core set too.

And if you wanna support me and this show, please tell everybody you know about PodScan dot FM if they need an API for all kinds of podcasts or maybe they need alerting and mention tracking and leave a rating and a review by going to rate this podcast.com/founder. It makes a massive difference if you show up there because then the podcast will show up in other people's feeds. Thank you so much for listening. Have a wonderful day, and bye bye.