I’ve always wanted to run my own business. Now that I’m 33, I’ve realized that I need to start actually trying if I want to achieve this goal.

What if this were a TV show? I would quit my job to create a startup. I would also be 22 and a lot hotter. Maybe I dropped out of college. The details aren’t important. “TV Jake” would drive himself to the edge of ruin. At the last second, everything would turn around and my startup would be the next big thing. But “Actual Jake” has a mortgage. At this point, “Going big or going home” isn’t as fun since it means “Go big or lose your home.”

The good news is that it doesn’t have to be that way. I’ve been introduced to online communities that view business differently. Podcasts like “Startups for the Rest of Us” and “Under the Radar” are run by independent developers that run small companies. They build smaller products at a more sustainable pace. The term “lifestyle business” also gets kicked around for these, since you’re exchanging some of the salary and comfort of a big company for the lifestyle you want.

I like the idea of starting out building small projects. This is similar to I learned how to program. I’d start tons of ideas. I made mistakes. I failed repeatedly. I’d try anything that sounded interesting. I wrote command line games, programs that solved my math homework, modifying WinAmp plugins to see what would happen. Eventually it started to stick.

I like the idea of failing on small ideas and building up. It maximizes what I can learn with a limited time budget. This approach has been informed by a lot of third parties. For instance, Rob Walling calls this the “stairstep approach“. David Smith of “Under the Radar” often talks about how he has a portfolio of products rather than going big on one.

So I’d like to learn business, and I feel like my first goal is very achievable:

Make $100 of profit, not counting the value of my time, on a business idea by the end of March, 2019

My first business goal

I’d like to do a few things to try to achieve this goal.

• Incentivize myself. Ultimately I’d like to pay off my mortgage. BAM! Incentivized.
• Hold myself accountable. I’m going to write a blog post once a week about what I have been doing in order to achieve my goal. I’ve heard this go both ways: “telling people about your goals feels like an accomplishment, which makes you less likely to actually accomplish them” versus “telling people about your goals adds a social pressure to actually complete them.” I’m choosing the method that involves filling out this domain with more content.
• Work at least 5 hours a week on it. I believe that I will be working more than this on average. But setting a floor will mean that I will continue to make forward progress while giving myself the option to take some time off if I start to burn out.

So, let’s get started!

What did I do this week?

This week was all about ramping up! I split my time between doing introductory reading from people who run small businesses. I also started gathering data to look for the first opportunity that I want to do.

Side note: my first goal, “$100 of profit without factoring in the value of my time,” is low enough that it enables a lot of options. If the weather warms up, “selling umbrellas in Manhattan when it rains” could even be a way to do that. But I’d like to practice working on businesses with scalable economics. I’m not going to look for these kinds of opportunities unless I start to run up against my March 31 deadline.

I partitioned my research so that I wasn’t reading too much up-front. There’s no reason for me to read an article about improving my conversion rate if I don’t have conversions. So I divided up TODOist into a few really coarse categories, “Research”, “Setup”, “Validate”, and “Build”, and divided interesting articles into those buckets. I didn’t look at anything that ended up in a bucket past “Research.” Then I skimmed the articles that ended up in the Research buckets for ones that seemed particularly good. I took notes as I went, organized by category. This makes it easy to find the relevant article when I start something new like designing an onboarding flow.

The best article I read this week was a set of notes on the talk “Blind spots of the Developer/Entrepreneur” by Ben Orenstein. I thought it had a lot of really pragmatic advice for trying to make money on info products. This inspired a few of the ideas that I had this week.

I also started brainstorming and investigating niches that I could start using to make small products. I had the following three ideas:

• Trivia questions. There are tons of existing companies that do things like run trivia nights or sell packs for you to run your own. I could pick a really narrow niche of trivia and sell questions for it, and slowly expand into being a trivia generalist. I’ve been going to a trivia night every week for the past 5 years, so I feel like this can inform the decisions I make. Plus, it means I know a few people who I can talk to about it – the trivia jockey, the bartender, and my friends.
• Info product for Google Docs. I was a Googler that worked on Google Docs for over 4 years, and additionally I answered our internal feedback list. I’m one of the best positioned people in the world to write an info product on how to get the most out of Google Docs. This would be done as a Squarespace site designed to sell the info product. This would also give me an avenue to expand into other products and services, and would provide passive income.
• Info product for how to get ramped up on PhpStorm, which is an editor that actually requires a license to run past the trial period. Since it has professional users, I’m more likely to be pre-qualified to users that are willing to spend money.

I vetted each of the ideas with the AdWords keyword tool. It may be a mistake, but I’m basically starting with a channel that I’d like to succeed with and comparing based on what has the highest demand.

The results were surprising to me. An unbelievable number of people look for trivia questions, and the search results for a lot of popular queries don’t really seem to serve the domain that well. In comparison, not many people were searching for Google Docs at all except for very high-level questions like “what is Google Docs?” Any approach here would have to be built around long-tail queries, which I think would be difficult to validate without any experience. And almost nobody was searching for PHPStorm anything. It was hard to justify doing either of the info product businesses even with some generous assumptions about conversion rates.

What am I doing this week?

This week I’m going to look closer at the trivia idea. I want to identify a segment within the search data that I can target. My current thinking is that I can try to validate whether holiday-based trivia is a good idea by targeting some upcoming holidays. MLK day is too close; I’d prefer to run a test for the 2 weeks before a holiday. But next month has both Valentine’s Day and President’s Day, so I could try to prepare trivia questions for each as a validation step – will people buy it at all? These are a month in the future though, so I’d also like to try to identify a second segment that I can start to target either this week or next week.

Interestingly, the government shutdown has also been on my mind. I wanted to start up an LLC with Stripe Atlas since the also automatically start up a bank account. However, I know that there’s a chance I won’t be able to get an EIN from the IRS while the government is shut down. So I’ve been holding off actually forming the LLC as much as possible.

That’s everything. See you next week!

Next week on “Learning about business” – I still haven’t learned about business.