Microstartup Stories: Initial Thoughts

A while back I read this post saying that you should write a business plan. Previously I thought business plans were dumb. I recall that being the conventional wisdom in the tech world and hearing people like Paul Graham and David Heinemeier Hansson say so. But that blog post changed my mind. And it opened my eyes to the idea that business plans don’t have to look like stereotypical business plans, just like how essays don’t have to look like the things you wrote in English class.

Basically, writing is a great way to think. I’ve found this to be true myself, and I’ve heard various smart people who I trust say it as well. So then, before pursuing some sort of business, why not write about it? I think it makes sense, so that’s what I am going to do here.

I am going to write about a new podcast I am launching: Microstartup Stories. The idea is to interview founders of companies that are making less than $5k/month. The interviews will be very long and wide ranging. 2-4 hours probably. And they will loosely follow an outline.

Costs

Overall, the costs of pursuing this seem almost negligibly low.

Money

This shouldn’t really require me to spend any money. I’m using Anchor which is free. I already bought a nice microphone a few years ago.

Time

A few days ago I listened to this interview of Courtland Allen of Indie Hackers. Courtland talked about a lot of great things in this episode, but one thing in particular that stuck with me was this:

Maybe two or three months into it, I was like, this is an endless slog of coding. This is going to take me forever. I don’t see like the end of the rainbow. I need to just call it quits right now. At the time where I was working on that, I saw a couple stories on Hacker News that people who would come up with new ideas and we’re already making five or ten grand a month, and I hadn’t even launched my thing yet.

So I was like, okay, this is like a dud. I should scrap this and go back to the drawing board and figure out what are all the different lessons that I’ve learned after years of doing this? Let me make sure I’m systematic in how I approach this so I’m not just going to make the same mistakes again.

I had repeatedly made this mistake that a lot of software engineers make where we just spend way too much time coding. I think the biggest lesson at the top of the list was only work on things and you can build in a few weeks. You know, I went from idea to basically launching with Indie Hackers in exactly three weeks, and it didn’t require very much code at all. It didn’t require a lot of marketing or anything. It was just super, super easy.

I really like that. Only work on things that you could build in a few weeks.

Well, it’s not a perfect rule. I think about it, like everything else, through the lens of costs and benefits. Some projects take years to build. That means the cost is higher, compared to something that only takes a few weeks for instance. But having a higher cost doesn’t automatically mean that it’s not worthwhile. Maybe the benefit is really huge too. This is an extreme example, but something like SpaceX comes to mind. Just because SpaceX took more than a couple of weeks to build doesn’t mean it wasn’t worthwhile.

I do think it’s a good heuristic though, to focus on things that you could build in a few weeks. Especially given the goals that I have of bringing in some side income. I’m not trying to take over the world. At least not yet.

This podcast satisfies that heuristic of taking a couple of weeks to build. Hell, it really will only take a couple of days. So in that sense, the downside is small. If it doesn’t work out I won’t have lost all that much.

As for the ongoing amount of time I spend on this, I don’t expect it to be much. Maybe I release an episode once or twice a month. Call it two episodes and three hours of recording per episode. I don’t plan on editing. It’ll take some time to email potential interviewees and chat with them. Maybe an hour of emailing per episode? That sounds pretty conservative but let’s go with that. That’s eight hours a month so far. Maybe there’s another two hours of miscellaneous stuff I’m not accounting for. Call it ten hours a month as a rough estimate of the time commitment that is reasonably planning fallacy proof. That’s 2.5 hours a week. Not bad at all.

And time is costly in proportion to its opportunity cost. If I was going to be doing something else with those 2.5 hours that, I don’t know, was going to make me $10k/hr, then consuming 2.5 hours/week of my time would be a pretty big deal. But the opportunity cost is not nearly that large. Currently I spent too much time procrastinating on the internet watching YouTube videos and I expect that it will be that time that is replaced with podcasting time.

I am trying to think of other projects I could pursue that would be even more valuable, but so far I haven’t really thought of something. If I do and the 2.5 hours a week or whatever it is becomes an issue, I could always pause or quit the podcast.

Granted, there is the risk that I get sucked in to the podcast even if it isn’t the best thing for me to be doing. That happened to me when I worked on Premium Poker Tools. I like to think that I will be able to resist it though.

Bad at interviewing

I think this is probably encapsulated by the previous section on time, but you can think of one potential cost here of me being bad at interviewing and this going poorly.

Let me back up a bit and provide some context. I tried starting a podcast a few years ago. It didn’t really go well. The idea was to dive really deep and be really comprehensive. To utilize Socratic Grilling. I didn’t feel like I was able to do that though. If you think of conversations as path traversal, I felt like we were jumping from point to point on the road instead of traversing through the path how I wanted to traverse it.

This might make more sense when you contrast having a conversation with someone to writing. When you’re writing, you are in full control. You can structure the post however you want. But when you’re having a conversation with someone, things just kinda head in whatever direction they head in, and you don’t necessarily have control.

Maybe this doesn’t sound like a bad thing. Maybe conversations are more fun when they’re free flowing. Maybe it’s more interesting to follow the lead of the interviewee than the interviewer.

Maybe. It’s not the hypothesis I want to test here though.

What I want to do is have an outline. An outline that says here are the points I want to hit on, here are some sub-points, and here is the order I want to proceed through them. It doesn’t need to be adhered to exactly. Some deviation is ok. And as we’re going through it, we can take “pit stops” and go off on various tangents. As long as the high level outline is roughly adhered to, it’s fine.

I’ll expand on this approach more in a follow-up post, but yeah, the high level outline is what I want to utilize here. I expect I’ll be iterating on it a lot, but not outright ditching it.

And speaking of iterating, that’s what I see myself doing here with my second stab at starting a podcast. Again, I was inspired by that interview with Courtland Allen. He was saying how Indie Hackers was like his seventh attempt at a business I think. Before that he tried six different ones, and none of those six had gotten him to the point of ramen profitability where he was able to live frugally and pay his bills from the money he made off his business. So yeah, just because my first shot at a podcast didn’t work doesn’t mean that my second, third or fourth shot won’t work. Let’s see what happens.

Benefits

Overall, the benefits feel really layered here. Maybe I just get the benefit of A. But maybe on top of A I also get B. And maybe on top of A and B I also get C. It’s not as linear as that, but this layered analogy still feels useful.

Fun

I think this is a great place to start. I might find this to be fun. I think there’s a pretty solid chance of that actually. And if I did find it to be fun, that’d probably be more than enough to make this worthwhile. Like I said before, the tradeoff is probably spending 2.5 hours a week passively watching Wendover Productions on YouTube or actively^[1] talking to microstartup founders about their stories. I think the latter sounds more fun by a pretty wide margin.

Educational

I plan to start startups throughout my life. I see it as a skill that can be improved on. Interviewing startup founders and diving deep into their stories will probably teach me a thing or two. That alone probably outweighs the costs, but especially when you combine it with the benefit of fun it probably outweighs the costs.

Networking

Talking to all of these founders might yield some sort of networking benefits. I don’t really have a concrete idea of what that would look like, but hey, I’ll take it.

I also have some startup ideas that involve selling to startup founders, so meeting people through the podcast would be helpful for those startups ideas that sell to startup founders, as well as developing the audience of listeners.

And if this podcast ends up being not a total flop, I guess it’s a thing to throw on my resume, which might impress people and make them more eager to work with me on future projects.

Money

Wow, I’m this far down into my “business plan” and this is the first place that making money has appeared. It looks to me like this would be worth pursuing even if there was zero chance of making money off of it, but at the same time making money would be really awesome.

So, how much money could I make off of it? Well, let’s see. I remember Courtland saying he made something like $7-8k/month off of Indie Hackers before selling to Stripe. It took a while to reach that point though, and he was working on it full time. And it is probably the most successful startup podcast out there. So eyeballing it, maybe 1/10th of that would be plausible for me? Call it $1k/month?

Googling around, that seems like it’s in the right ballpark. Launchkit eyeballs it at:

Small podcasts: $150-550/month (1k listeners/episode)
Medium podcasts: $1,200-5,000/month (5k listeners/episode)
Large podcasts: $10k+/month (10k+ listeners/episode)

I could see up to a few thousand dollars a month for me. I could also see it being a total flop. Nothing inside that range would surprise me. I would be surprised to see it venture into that “large podcasts” territory. The target audience is a little niche, I don’t plan on putting that much effort into this, and I don’t see myself as a super talented interivewer, but hey, you never know.

Getting a bit more concrete and into the logistics, I think ad revenue is the most plausible way of making money here. The audience is potential startup founders^[2], so people who have something to sell to potential startup founders have a nice targeted audience. Places like Stripe, Vercel, maybe Fireship. Those are just some rough examples that come to my mind initially. I’m confident I could come up with better ones if I thought harder and did some more research.

Affiliate stuff is also possible. I really don’t want to do that for products I don’t totally believe in, but maybe if there are products I believed in I could explore that. Donations are another possibility. And paid content is another. None of those feel too promising to me, but they’re probably plausible enough to take a harder look at if the podcast starts getting large enough.

Thinking big

It is possible that this balloons into something genuinely big. I think people often underrate the possibility of that. I could see a large community forming around these sorts of founders, just like what happened with Indie Hackers. And Indie Hackers got acquired by Stripe for presumably something in the double digit millions.

It’s also possible that I turn out to be a great interviewer and people just love the content even though it’s kinda niche. Big podcasters make lots of money. Joe Rogan was the highest earner and made $30M in 2021. Bill Simmons made a more modest $7M. I’m not thinking I’d be that big, but it is as least possible that if things really work out here I reach something like, idk, $500k/year.

Going in a different direction, I wonder if this could ever pivot into something similar to Product Hunt, being a listing of products?

Logistics

Finding interviewees

Fortunately, there are already some communities popping up involving this idea of “microstartups”.

Microstartups.co is basically a listing of microstartups + some really brief text-based interviews. Perfect for me. I will probably email a bunch of founders listed there.
MicroFounder is another great one.

The above two are super targeted and perfect for me, but I can also find people to interview on places like Indie Hackers, Beta List and Indie Hackers.

So yeah, finding interviewees shouldn’t be very hard at all. It wasn’t hard for my previous podcast either. I think founders are generally pretty receptive. The incentives are well aligned. They want the free publicity and are also just frequently cool people who are happy to chat.

Recording

Anchor.fm does a good job of making this easy. I remember researching alternatives when I was doing my previous podcast and coming to the conclusion that Anchor is right for me. Same with the microphone I’ve got.

Finding advertisers

Anchor does help you with monetizing, but my hunch is that it’d be better for me to find my own advertisers and sponsors. I’ll probably have to do some research, think about what sorts of companies would want to advertise to my audience, and cold email a bunch of them. As an example, I came across Supabase yesterday and they seem like a good candidate.

I could also see who advertises on similar podcasts and contact those companies.

Conclusion

Overall, the benefits seem to pretty clearly outweigh the costs, and I think this means it’s time to get started! I am still eager to receive feedback though. I expect to iterate and change my mind on various things as I move forward.

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I really like this idea of active vs passive. It reminds me of something Paul Graham said about pursuing things that you could show to someone else and they’ll think it’s cool. Like if you write an essay you could show it to someone, but if you read a book you can’t. Err on the side of the former. I think something similar is true for having fun. Active things where you have something to show for might be something to err towards.
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Sort of. I don’t plan on becoming a chef, but I still watch YouTube videos about the lives of chefs.