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The Stupidest (Successful) Path to A Profitable Side Hustle

Would you like to build a business with your friend to $120,000+ in revenue while keeping your full time job?

I’m sure many of you are screaming, YES.

Well, I’ve done it, and I’ve done it in about the stupidest way possible. Let’s talk about what to do, and what not to do.

You see, over the last 3 ½ years Parker and I have slowly built GoStudy  into a healthy side hustle. GoStudy is a study platform that combines notes, notecards, and video with insight and attitude about how to cram and be incredibly efficient at passing the CFA exams. We aspire to much more, but that’s for another day.

GoStudy has been a crash course in business lessons. One after the other.

So, without further ado, here’s an incomplete list of things to avoid, followed by some of the better lessons in what to do.

What Not To Do When Building A Side Hustle

1. Pick a small AND crowded market that’s hard to escape

We started with a tiny market (180,000 potential individual customers anyone?).

That market is filled with large competitors like Kaplan. Three years later we’re still in that tiny market. You try bidding on a long-tail keyword search with like 20 monthly hits and entrenched competitors. It’s fun.

2. Build something that requires constant maintenance

I’ve literally written two 500 page books covering the 6,000+ pages of the Curriculum, over 2,000 notecards each meticulously tagged, built an entire 40+ hour video course, and graded hundreds of Candidate problem sets for the class we run on top of writing over 120 blog posts. And that’s after spending 18 months and 900+ hours just to pass the three exams in the first place. I still don’t dream about financial exam material, but it’s getting dangerously close.

What makes it even worse…the exams change every year. Sometimes not much, but always some.

3. Work in Fits and Starts

We worked night and weekends and didn’t quit our jobs which has definitely slowed us down.

We’ve tended to do everything ourselves because we’re extremely careful with what we spend money on. Sometimes that’s a good thing, sometimes its inevitable, and sometimes its just stupid

We didn’t invest in design for years. Until the end of Year 3 we were pretty embarrassed by our home page. But mostly, we’ve taken time off. The inevitability of incremental progress is easy to dismiss but powerful when you can get it going.

4. Don’t Focus 100% on Your Core Competencies

We built our first platform on mobile, which, despite his many skills is definitely not Parker’s core tech competency. That alone cost us 6 months of extra time and hundreds of dollars in outsourced work we could have avoided. And let’s be clear, this is when we were still selling PDFs out of the back of our truck (website).

So yeah, we made a lot of mistakes. But obviously we’re still plugging away. So we’re either masochistic, delusional, or feel like we’re heading down the right path (or all three). So what’s been good?

What To Do When Building A Side Hustle

 1. Work with Someone you Love

Working with Parker is first on this list. Really GoStudy has all been a conspiracy to keep that going. I just didn’t know it’d be this painful. Note: I say love above, not like, because as everyone will say, having a co-founder, a fellow dreamer in the journey is HARD, and that’s no different if its not full-time. Indeed, it’s a whole different set of sacrifices and balances that must be struck.

2. Be real. Care about your Customer.

We have a damn good reputation in the space. We get a lot of word-of-mouth traffic and clients. I think that’s because we actually care about helping people, and we bring a voice and perspective to financial exams. Some people actually like reading what we write, or at least they pretend to when they write back. We love the 10,000+ people on our newsletter because they make all the bad stuff a little bit less painful (and because we learn from them about what we should be doing).
It’s worth pointing out though, that once you have customers, you have to be very serious about treating them well, and that means maybe some of the side hustle freedom wraps into becoming a real business. It’s rewarding, but worth thinking about.

3. Embrace the Journey. Value Learning. Use Your Constraints.

It’s rewarding to build something out of nothing.
It’s even more rewarding to do that without spending any money.
To date,  we’ve funded every single penny of development, marketing, and third party help from our sales, and we keep banking money. On an annualized basis we’re growing like 250% a year. Oh the power of a small base. We could great a seriously impressive looking “up and to the right” growth chart if we ever wanted to put a pitch deck together.
Finally, there’s the things we’ve learned and the personal growth this journey has facilitated. From incorporating a business and filing business taxes to hacking our growth (yes we got a few cease and desist orders we can tell you about) and having difficult conversations we’ve stretched ourselves and gotten better.

4. Make time for Dreaming Big

We have a vision for GoStudy.
  • We want to build an integrated study experience that uses predictive analytics to tell you what material you struggle with
  • We want to build a platform for others to use to learn any Curriculum
  • We want to move to a more open source network of content creators

That part is really exciting. Especially because we think we can keep doing that as we build out new verticals to increase the cash flow. But maybe its all still in the realm of the practical. We also take time a couple of times a year to think bigger. For example what would a world of true VR/AR look like in education and learning? The dreaming helps take a step back and puts the day-to-day slog back in perspective.

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