Things I still don’t know after building a six-figure business

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⏱ Launched on

Mar 7, 2017

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6 mins

About 8 months ago I launched the Code-Free Startup, an education platform teaching non-technical people how to build apps without coding. Flash forward to today, and it's been a wild ride. I always thought once I passed $10k a month in revenue I'd have everything figured out, and from reading a lot of "what I've learned" posts I get that feeling that anyone with a 6-figure business must be just way smarter than me. So it's kinda refreshing that there's still a lot I don't know about.

When I write, I feel like an armless, legless man with a crayon in his mouth. - Kurt Vonnegut


Change the crayon to a laptop, and this is how I feel. I've probably wasted the most time on marketing, trying to figure things out that have little to no impact on people signing up. Most of my traffic today comes from Google.

I think the reason I'm ranked so high for searches like "code a startup" or "startup coding" is because 1) the name of the site is Code-Free Startup and 2) I launched on Product Hunt and Google seems to like them.

Through free signups on the site, my email list is probably the thing I spend the most time worrying about. Once you get a few thousand people on an email list, there's this weird pressure that comes out of nowhere. "Oh my god it's been two weeks and I haven't sent an email to them, they all must hate me."

I've been working on fixing this by segmenting my list using the marketing automation tool Drip. This way, I’ll be able to focus on different segments of my list based on their actions and content/engagement should improve.

Segmenting is great for engagement but requires more content, which could be an issue based on my production (more about that below). But because making content is something I know how to do and paid advertising still scares me, it's worth it.  


I've had a few articles drive traffic, but writing has so far been a somewhat inconsistent habit. My first few articles that did really well were published on Medium and each drew a few hundred signups that converted well. But now that Medium is floundering a bit, I think the only way to have a successful strategy is to submit writing to established publications.

Individual Medium feeds are filled up with a lot of "7 habits to be a millionaire!" type posts, so you'll have to find the editors of publications like The Startup or The Mission and email them with post idea to get traction. From what I’ve learned, the secret to great content is investing time, if you can swing it.

Writing isn’t worth pursuing unless your finished articles are at least 5x more valuable than what everyone else is writing. Speaking with some of my favorite writers, there seem to be two ways to accomplish this.

The first camp spends a long time on each post. The post is edited 5-7 times, ends up at around 2000+ words, and is packed with insight. The goal is to get a reader to have an involuntary "this is so valuable I need to share" moment. People like Tim Urban and Ramit Sethi fall into this category.

The second camp treats writing like a habit instead of a skill, delivering more value through better quality writing. They write 500-1000 words a day, publish more often, but over time strengthen their writing muscles to the point that even a first draft has a lot of value. People like Srini Rao and James Altucher are good to study in this area. There’s a great piece Srini wrote about his 1000 word a day habit. (sidenote: might be just a correlation, but a lot of writers in the second camp seem to be having success with Medium publishing).

Right now I’m in the third camp, which is basically the summer camp where bad children get sent by their parents to learn about manual labor. I’m spending less time per post and also not writing a lot. I think the trouble comes down to the actual act of writing and how difficult it is to feel okay about producing terrible first drafts.

A great book called “Bird by Bird” describes the first draft process as the only way to get any writing done, but spends most of the book teaching how to deal with the imposter syndrome that creeps in when producing drafts. To work on this “draft fear” (much different meaning in 1939), I’m testing out two things: dictation and Facebook. Dictation just means I’m using the speech-to-text feature in Google Docs to get first draft ideas out of my head and onto paper. It takes a bit of time getting used to, but seems promising.

For Facebook, I’m not actually using the platform (already have enough distractions), but I am writing articles in the “New Post” area, and it works. Even though I don’t hit “post”, writing in the share box seems to make my writing style more conversational and effortless.

It also prevents one of the more common distractions when writing, research: “oh, this sentence should link to this fact, let’s spend 3 hours on Wikipedia”. One of the best tips I’ve heard is “write like you’re writing to a friend” and the Facebook post box helps with that.  


This has been the most fun for me, mostly because it’s been working. There’s a section on my site where students can submit and upvote what kind of startups they want to build (ex. I want to build a marketplace like Airbnb, dating app like Tinder, etc).

Once an idea gets 300 upvotes, I go to work trying to build that app. Once I have it figured out, I record the learning process and turn that into a course. In 8 months I've released 7 courses and recorded just over 100 videos, each around 20 minutes long. That number blows my mind, and I think it's an undervalued benefit of starting a company: writer's block/creative block just disappears once you have paid customers. And it didn't matter whether I had 2 or 200 paying customers, I still felt the need to deliver on the promise of the company.

So I guess a takeaway is to get one paid customer, build for them and you'll end up building a lot more. The downside to building quickly, especially in a small company, is the product backlog. I have a long list of improvements to make to the platform. Finding the time to chip away at this list is easy.

The difficult part is being able to sleep knowing there is such a big list growing into a backlog monster under my bed. What helps manage this stress is the strategy behind the list. When a new feature/bug fix comes in, I label the source (I noticed it/a customer noticed it) and how many people it's affecting. Anything that impacts paid users is labeled urgent, and none of those remain on the list.

Looking at the list now, everything that remains is either an improvement or super obscure bug. What to do now: it's a weird spot to be in where you're comfortable running a bootstrapped business and there aren't any venture capitalists pushing you to scale. There's still that subconscious feeling of "oh no what happens if this business explodes tomorrow" but for the most part, things are good.

My goal this year is to continue to grow the business at a comfortable pace. I find myself constantly referencing Paul Jarvis' article on growth  to keep myself balanced. Especially living in San Francisco, there's a crazy energy around growth at all costs, even if it means deferring your happiness for 4-6 years until you get acquired by Google. A lot of people pop out on the other side of that trade-off and life isn't exactly as rosy as they expected. There are a lot of unhappy people driving Teslas in Silicon Valley.

On the other extreme is the lifestyle-business-at-all-costs crowd. They automate their business, head off to a beach somewhere in South America and expect all their problems to melt away. Then the loneliness and lack of purpose kick in. So instead of either path, I'm just going to keep shuffling along trying to build things that I enjoy building and learning the stuff I don't know yet. Let’s see how that goes.  

Why this post succeeded:

This is one of my most shared posts, and if I had to guess why, it's that way too many entreprenurs look back at what they've built and re-write history. That history always makes it look they knew what they were doing and everything lined up perfectly with their plan. It's a common cognitive bias, and I think people are yearning for success stories that are more transparent and honest. Every stage of growing a business is full of uncertainty and feeling like you're going so far in the wrong direction, so I don't want to edit that out.