Building a Technical Content Agency in 2021

• consuming, testing, and updating clients' external-facing documentation
• writing technical blog posts/tutorials/how-to's
• creating explainer and demo videos

Challenges

• Finding Qualified Writers

One of my biggest worries was whether I would be able to find enough qualified contractors to fulfill work as I grew my business. I knew the cheaper option was to take writers and try to teach them about programming. The more expensive option was to take developers and teach them how to write. Initially, I went with the first option.

I ran a two-week course up-skilling nontechnical writers into technical writers. My hypothesis was that it was possible to teach trained journalists how to build a Flask webserver in two weeks. This turned out to be...incorrect. It'd been so long since I learned how to code that I think I just forgot how much knowledge is assumed...even things like using the terminal, or what a "string" is.

Eventually, I discovered that it was easier to go in the other direction, by tapping into non traditional pools of talent like graduate students in computer science and new moms and developers on “sabbatical”. What I could offer these people were two things: flexibility and public bylines. And I paid better than some competing tech writing programs that companies have set up. (Usually something like $700/blog post.)

• Standardizing Pricing

I had trouble figuring out the best way to do pricing. Should it be per project, per hour, per monthly retainer? At this point, I largely try to do per project, but it's still a bit of a hodge-podge.

• Operational Overhead

Maybe this is because I'm still early on, but many of my contracts are relatively short durations and they're frequently being renewed. This creates a lot of operational overhead, in terms of renegotiating, drawing up contracts, sending invoices, etc.

• Being Part of the Team

My clients will often plug me into their Slacks, which is great because it feels like you're part of the team, but then what are the expectations in terms of availability, attending weekly meetings, etc?

• Client Management It's only now that I'm in a client-facing business that I realize how spoiled I was working infrastructure, where there were basically no deadlines, and no external customers. Some things I still struggle with include:
• What to do if your client wants X but you actually think the right course of action is Y. Should you stand your ground or give your clients what you want?

• Truly modern docs tooling
• Companies like Stripe and Twilio that are well known for their docs have entire engineering teams devoted to building docs tooling. If you can't afford to do that, your off-the-shelf options are basically Gitbook, ReadMe, or Docsaurus. None of these are, IMO, really great products.
• I recently learned about a new templating language called MDX that allows you to embed React components in Markdown. I would love a docs tool that is MDX on the frontend, headless Ghost on the backend
• For a lot of developer-facing projects these days most of the action is actually happening in Discords/Slacks. That's where a lot of questions get answered. There should be a way to automatically parse all the questions that are posed/answered in chat communities and lift them into proper documentation threads that can be indexed by Google.
• None of the have good analytics for what works and what doesn't
• Better Managed Ghost
• I've spent a lot of time working with Ghost sites. I like the product and respect the team. The core product is open-source, the managed service is a non-profit, and in a world where $10 billion is the new $1 billion, it takes a huge amount of integrity to not run after that.
• That being said, I think the existing managed ghost service, Ghost Pro, lacks customizability. In order to change the email templates or translate the transactional emails, you have to edit the core files (which are not accessible in the managed service), and self-host. I think there's room in the market for a better managed Ghost service, or even a build tool that does some of the upgrades/config stuff for you. Mostly, I'm bullish on the Ghost ecosystem. If you think of the number of sites online right now that are hosted on Wordpress, and if you think of Ghost as the new Wordpress, that's probably a half trillion dollar market.

Next Steps For Frindle

• Raising a venture fund that's attached to the agency and invests in client companies
• The fund would invest expertise and help with docs/content in addition to capital
• Form Capital does something similar with design help. Not Boring Capital is another example where Packy basically writes long profiles of the companies in his newsletter in exchange for allocation.
• Taking client equity as payment. Writers, videographers, engineers would work part-time for the agency and get a cut of that equity. This is a way for "regular folks" (not accredited investors) to build a diverse portfolio of startup equity, by lending their skills and expertise part-time to a bunch of companies, rather than full-time to a single one.
• a crypto spin on this is the agency helping protocol projects with documentation/content and being paid in tokens. Freelancers are entitled to a share of those tokens. This might actually be easier to implement because I think the idea of "sweat equity" is a lot more accepted in crypto. For example, rabbithole.gg's business model is getting paid entirely in the client protocol's tokens. Another good model to follow in crypto is VectorDAO, a collective of designers helping crypto projects and making investments alongside. I’m thinking about doing something similar for content.
• something that inspired this line of thought was reading Packy's post on the cooperation economy, in particular this passage:

Liquid Employment

Maybe because I’m a full-time newsletter writer and don’t work for a company anymore, but I can’t shake the idea that careers will become a lot more fluid in the years to come.

Pre-COVID, showing up to the same office every day made it hard to work for a second employer. But when another job is just a Slack workspace away, it becomes much easier to work multiple part-time jobs.

This flexibility will significantly increase the opportunity cost of choosing an exclusive employer. Every decision to spend four years vesting at one company will mean shutting off hundreds of other opportunities.

Investors would never choose to invest in just one company; the risk is too concentrated. Instead, they build portfolios. Over time, workers will invest their time in a similar way.

Currently, liquid employment is largely impractical for workers and employers alike. But the same thing could have been said about remote work at one point. Spreading risk over a few companies makes sense for employees. That means that the companies that want an edge to hire the best people for a given role will eventually adopt it.

When I wrote that, I assumed that people would work for multiple companies at once, in a role somewhere between contractor and full-time employee, and I still think that’s a possibility for many people. But I now think my view was too limited.

What Liquid Work provides above all else is optionality. That may mean working for a couple of companies simultaneously, but it might also mean working for yourself, teaming up with others for time-bound projects, investing as a group, and contributing to a DAO in an area of interest. It’s fluid.

When I was reading this, I really felt that Packy was writing for me. I've always been a generalist — a developer, a writer, community-organizer — in a way that felt both extraordinarily powerful and wildly unsuited to traditional work. I sort of compromised by working full-time as a developer and pursuing a side hustle in journalism. But it always felt like I was wasting some of my talent, or making a suboptimal financial decision. One of the things I want to explore with Frindle is whether some of the tradeoffs we take for granted in our careers — ownership for flexibility, for instance — are really so inviolable.