The Orchestration of Solo Bootstrapping

Getting COVID this week left me with a lot of time to be productive over the weekend. I spent a sizeable chunk of that time finishing setting up this blog, and most of the rest of it reading and watching Star Trek: The Next Generation.

As is often the case, despite my other plans and feeble attempts at mental discipline, my reading took on a will of its own. Fortunately, I think that immersing myself in https://www.indiehackers.com for multiple hours helped me knock out some cognitive cobwebs and overcome some mental blocks, and since I have this new shiny thing I thought I'd share my insights.

The Orchestration of Solo Bootstrapping

It's easy for devs who are trying to bootstrap a software business to think of programming as being the main thrust of the business with various bolt-ons: sales and marketing, design, customer support, accounting and legal. That was my mental model until today, and I often found myself thinking something along the lines of, "I've got the main thing ... Now if I can just figure out sales and marketing I'll be good."

Unfortunately, I'm realizing that this mental framework is actually pretty inadequate. Building a business is not "creating a thing of value and then making money". Rather, building a business is actually a big list of disparate concerns each requiring different deep skillsets. In an established business, this is a problem that we'd solve by hiring people with the right skillsets. But, if we're building solo, how can we get to that point?

The usual way to solve these problems is to simplify everything that's not directly related to our value proposition (in other words, Do Things that Don't Scale). We can use standard legal forms and keep our accounting simple by avoiding elaborate legal structures. We can use templates and generators to achieve quality designs and then fit our content to them. Thus, we can bypass a lot of the nuances that a larger business would address; many potential buyers will forgive us as long as the core value proposition is there, and we don't need to convince everyone to buy — markets are large and a tiny slice of the pie is enough to get our little business bootstrapped.

Here's the problem: that approach doesn't really work for marketing and sales. That's because the way that you sell and market your product is inherently unique to the time that you're selling it and the value proposition it presents and therefore approaches to sales and marketing do not generalize well. We cannot look at the approach that Reddit or some other company took and then rewind time and apply their marketing strategies verbatim because they don't apply anymore. Reddit's unique value proposition is theirs and we cannot sell their product. We especially cannot sell their product to their exact audience. Therefore, sales and marketing is inherently an adaptive thing which means that in order to be successful at it we need to be better at it than most of the other business skillsets that we're covering as a solo founder.

What's more is that sales and marketing are unequivocally the most important part of our business. Without sales, we cannot make any money. Once we can make money we can hire people into other roles with appropriate skillsets and therefore scale the business. So, there is no chance of bypassing the sales process nor is there any real chance of succeeding without some understanding of it. Further, since it is a deep skillset (selling stuff is hard), we know that we'll need to invest some real time and study into it in order to do it successfully. And, we know that once we can sell our product we can scale the other parts of the business effectively. So, we need to commit time to studying sales willfully and get good enough at it to actually sell our product and generate enough profit to get the business going.

In order to sell anything, we need an audience. We can buy access to audiences through ad purchases, but I hypothesize that this is not generally nearly as effective as building our own audience, particularly while we are teaching ourselves how to sell. Buying access to an audience gets us a lot of exposure very quickly, but it does not surface meaningful feedback (which is primarily what we need when we're learning), since most people are not going to comment on an ad campaign that they see on social media. We can use things like surveys to solicit additional feedback, but the reality is still that most people are not going to go out of their way to engage with and ad that they didn't find compelling and tell you why.

On the other hand, if we cultivate an audience organically by consistently engaging with different communities on topics that actually interest them then we can learn about them and establish a genuine rapport. If we then work our product decisions in the direction of our audience's needs, we will have genuine common ground for discussion and a real feedback loop that we can use to learn how to sell. In this way, we can try sales and marketing experiments in unobtrusive ways without burning through a ton of cash in the process (when we're not attempting to sell, we can pretty much post wherever we want which means no ad buys). Then later when we have a better understanding of our target demographic and their specific concerns, we might be able to run ad campaigns more effectively.

This approach also particularly makes sense for me since I sell developer tooling and developers tend to be less interested overall in traditional forms of advertising and tend to be more responsive to content that provides them genuine value (blog posts).

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