Tipping over — The Bootstrapped Founder 335


Dear founder,

These last weeks have been a bit much. What do they say? “Take a break before the break takes you?” Well, I got quite close to that this week.

🎧 Listen to this on my podcast.

I’ve been quite active working on Podscan in many different ways, and it has been overwhelming at times. I found a way to cope with this, and I found a way to still get done what I needed to get done, so I wanted to share the whole journey and the whole emotional state that I was in and am in now, because somebody else might feel equally overwhelmed or somewhat incapacitated by the scale of things in their own business.

There’s generally a problem in running a software business: that it’s a lot. Not only do you have to fight for something that doesn’t exist anywhere else, because it’s a new thing, and nobody else has ever built the exact same business as we have. We have this baseline level for needing to justify it, and there are so many things that you initially never even thought about that may or may not happen during the process of building such a business. And then they tend to swamp you when they occur in rapid succession or all at the same time.

For me, the last couple weeks of Podscan have been both very productive and very taxing at the same time. The biggest thing that has been occupying my mind has been the Paddle AI Launchpad demo day which I was fortunate to be invited to. I joined the AI Launchpad cohort a couple of months ago because my friend KP asked me if I was interested, and I thought that even though I had just received some funding already, it was time to kind of spread the word a bit more and hang out with my founder peers that are working with the same technology that I use.

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So I joined the Paddle Launchpad, and it’s been a wonderful experience. But the big thing (after all the wonderful lectures and founder huddles and the interaction with the community in Slack) was the Demo Day, where 10 out of 130+ companies were invited to pitch their business and product to a larger audience: the cohort, journalists, Paddle employees and anyone willing to listen. In the end, Paddle reported over 500 registrations for demo day. That’s a lot of attention.

And it requires a lot of work to participate.

Besides running Podscan, dealing with customers, building features for them, making sure their integrations work, and also thinking about what Podscan needs next, like prioritizing features on the roadmap and having customer discovery conversations, and dealing with improving the existing system — all of these things now were overshadowed by the need to create a pitch deck and to rehearse a presentation and to record a showcase video.

If you know me, you know that I tend to talk a lot when people allow me to, because that is my process of thinking. I think a lot while I speak, and things open up in my mind as I verbalize them. This is great if you have a podcast like this that can go on forever. But it’s not that great if you only have two minutes to actually pitch your whole product and the business around it, plus a one-minute video that you might want to pre-record.

So all in all, the pitch was a three-minute opportunity for me to talk about Podscan, and I kid you not, it took me days to get my thoughts under control.

Only with the help of Danielle, my partner and co-founder of a previous business, was I able to create a coherent pitch. She took over the design of the slides and the narrative within, and presented me with a pitch deck that I only needed to write a couple lines of story for. Then I had the baseline, the foundation of my talk, and I recorded the video for the showcase.

And then, I rehearsed. A lot.

It was the first time I ever pitched anything of mine. I’ve been participating in pitches for other businesses that I had co-founders for, but I’ve never pitched anything that is a brainchild of mine, and that was stressful. It was anxiety-inducing, and it took me days to get my head wrapped around these three minutes, and I rehearsed for many days and nights.

But I wasn’t alone. Besides Danielle’s heroic efforts, the people from Paddle were extremely accommodating, too. They were very helpful with going through the slides and going through the video and giving feedback and allowing the founders time to rehearse on the platform that the event would be on. It was a really nice experience.

On the day of the pitch, I was extremely anxious. My heart was racing right up until the moment that I was called to go on stage.

And then, I felt serenely calm.

When I started the pitch, I just fell into what I would call my camera presence, or my “the recording light is on” state of mind, something that I’ve been doing for hundreds of times over the last couple years, speaking confidently into a microphone or looking at a camera while doing it.

Of course, I’m technologically equipped to deal with this. I had a teleprompter going, I had everything set up, and I tested it multiple times before.

So when I started my pitch, it all went great. It went spectacularly well. People were really happy to see a polished pitch with a great pitch deck and a good video that had everything, had captions baked in, and made it easy to follow along. I brought my stage presence to it, and I explained Podscan to people, what it can do and what it’s for. I got good questions from the judges, too.

All in all, the pitch was great. And the cohort that I was part of was also spectacular. There were so many interesting projects — three or four podcast-related projects in an AI cohort to begin with — which were very interesting.

Ultimately, I didn’t win the pitch. Another project, Vanna.ai, won the pitch. But I did win the People’s Choice Award where the audience voted for the non-winning project that they liked most, which is nice. Paddle sent me some swag, which was really kind, and generally felt like this whole experience was a massive benefit for Podscan.

Even though it cost me a lot of extra effort and a lot of mental anguish to get to the point where I felt confident in it, I have to say that being able to pitch to somebody else —the elevator pitch version of Podscan— made me much more confident in what it is, what the business means, what Podscan can do, what I want Podscan to be.

That felt much easier after I had all of these crisp slides, the words that went with them, and particularly the important numbers, like market size, the total addressable market, the reachable part of the market, the reasonably reachable part — the TAM SAM SOM slide. That was all very useful to have looked into.

But it came at a price.

I noticed a couple of days into working on the pitch that I was quite physically overwhelmed. At that point, Podscan had a couple of technical issues that I needed to iron out for it to run in a stable fashion. So there were things that kept me up at night, quite literally.

And I had a couple of very intense days last week. Usually, I start the day at 7:30 in the morning, then I walk my dog, and I come back and I get started with work, and then I tend to stop around four or five, leaving room for an evening with the family. But there were several days that week where after dinner, I would go back right to work and grind until 10 pm — so it would be a 7 to 10 kind of day, which is 15 hours — that’s a bit much, right?

I noticed, particularly during those days, that I needed a way to stop obsessing about all these little challenges. There was a lot of obsession with the stability of the product, and as I noticed that my mental energy was needed for the pitch and the work that would have to go into that (which is creative work, not maintenance work) I needed a way to suppress this obsession with technical perfection.

I did two things. The first thing was, I just said to myself, “I’m happy with things mostly working.” I’d been chasing a network error for a few days already, which happened maybe once in a thousand requests. Not critical, but annoying.

But it derailed my focus.

And the moment I suppressed the error, and it didn’t always flood my inbox anymore and I didn’t see it, it was like, “Okay, this really doesn’t matter.” My back-end service will retry a connection if it doesn’t work, and if the error comes up more than 1000 times over the next couple of days, I will get an error again.

Dealing with things by taking them out of mind was extremely useful.

This is something I recommend if you deal with lots of little issues that may not be relevant but appear louder than they are: just shut off notifications. Allow notifications only for critical things or for things in critical quantities. That’s what I implemented for Podscan.

On the other side, there’s something I returned to that I haven’t done in months.

I started literally stepping away from the computer and reading fiction again.

I’m a big fantasy and sci-fi guy, and I’ve been reading several novels over the last couple days. I think I got three or four novels done in like a week, just because I took the time to read them. I read a lot of Brandon Sanderson’s books. I also read Ready Player Two, the sequel to Ready Player One, which was turned into a pretty entertaining movie. It’s a very nostalgia-80s and nerd culture-driven book. So that was really enjoyable to read.

In a way, this sounds like escapism, which it kind of is — I intentionally escaped the tunnel vision that was looking at my metrics and looking at my logs.

But it also allowed me something else that I noticed: I started feeling more empathy with myself and with the needs that I have, not just as an entrepreneur or a developer or a marketer, but as a human being who needs variety and balance in my life.

This kind of empathy towards myself allowed me to step away more easily. It allowed me to pull out of the perfectionist tunnel vision that I had been in.

Because when you’re working on a thing that isn’t perfect yet, my mind, at the very least, often goes to “well, if I just spent a little bit more time, the chance for me to figure out how to get it right this time is going to be higher.” So I get into this loop of spending more and more time. And there is very little empathy for my sanity at this point.

Reading fiction, and putting myself into the shoes of others and seeing their ever-changing struggles and the changing scenery around them pulls me into a different place. That allowed me to leave my computer, to get out of the software world that Podscan lives in, and just visit a different world for a couple of hours and then get back. That made a big difference. And it made a big difference for something that I didn’t even expect to impact, and that was the pitch.

It made the pitch easier, because as I was developing more empathy for myself I also felt more grateful for others, for other people that are part of my journey. I didn’t just see them as customers or as peers or as other developers who helped me out, which I already value quite a lot, but I saw them as human beings who enrich my life just as much as I try to enrich theirs. And that explains why I had such an easy time switching into “Hey, this is my pitch, and my product is great. Let me share it with you” mode when all the anxiety of the lead-up was gone. It was like, “Okay, this is really just me sharing something great with great people.”

I think having been able to step away from the debugging, the maintenance, and the operational side of a business, which often involves errors and things not working, reading fiction and just taking time to myself allowed me to look at the things that are working and that are great and that are positive.

It’s a perspective shift, an intentional reframe.

And in a way, after the pitch, I’m still riding that wave. This whole self-empathy increase allowed me to more easily say yes to “boring” features like building stuff that is maybe not as challenging technically, but it matters more to the customers, the people that are actually using my product.

Yeah, I didn’t want to redesign my emails — HTML for email is not fun. It’s probably one of the most horrible ways of building software, because it’s incredibly hard to test. It’s unreliable, and it is technology mixed from the mid-90s up until today. It’s really bad.

But I felt like, “this is something that other people are going to see, so I might just as well make it nice for them.” It’s not a cool AI feature, it’s not a fancy marvel of technology. It’s just a boring old email, but it’s something that connects me with people, that connects Podscan with people, that leaves an impression with them.

So in working on emails and onboarding —things that don’t feel like the meat and substance of a product— I realized that this is how I connect with people. The first couple emails that I send, those are extremely relevant. Those are the first impressions that people get. And every time I send a notification because somebody was mentioned in a podcast, well, why not make it look intentionally nice? It’s an invitation to connect.

Pulling myself out of the technical rut and getting more into the empathetic world of fiction really helped with this. It prevented me from dipping over into burnout this week. I think it was pretty close to me just needing a break instead of wanting to take one. And it also made me focus more on things that ultimately make the business better, more approachable and more enjoyable.

So it has been a week of a lot, but it also has been a week of stepping a little bit back into my own sanity and fighting the impulse to obsess over the business. And I think in being more present outside of my office, this has also benefited my presence in my relationship, and it’s benefiting my level of self-awareness that as a founder who needs to do many different things. Not all of them are product work. Many of them have much bigger impact than adding another feature. And sometimes it’s okay to step back. Sometimes, it’s okay to stand still before you keep tipping over.

And then, read a novel.

I'll share a few updates about my SaaS on the pod, and if you want to track your brand mentions on podcasts, please check out podscan.fm — and tell your friends!

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Arvid Kahl

Being your own boss isn't easy, but it's worth it. Learn how to build a legacy while being kind and authentic. I want to empower as many entrepreneurs as possible to help themselves (and those they choose to serve).

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