I'm a dumb ass. After some disagreements about my role, I quit my new position to pursue my dream in May 2020. As May set in, I convinced myself this was the moment I was going to become full-time self-employed. Damn was I ever wrong. Tried creating a few products. Either I wasn't invested in them properly, or didn't hit the right traction strategy. Only to end up messing around a bunch, and never really moving the needle. By now I realized I probably should been trying to build a freelancing business instead. Hindsight is 2020.

The first flop was a product idea I came up with after spending way too much time on the Indie Hackers website. I called it 'Statdesk' because the name sounded cool. My vision for this thing was for it to be an Intercom competitor. Seriously. I tried customer development and everything. Practicing cold out reach, asking strangers about their Intercom usage and grievances. Mostly, I just spent too much time on a particular website so my audience and market were the folks on this website. Bad idea. Only some people here make money, and they were pretty frugal. Frugality is a tough nut to crack, and I wanted to compete on price because, well, execution matters more than the product. I should have been executed for how naive I was, but everyone has to start somewhere. I did learn a couple things though. I got confident enough to talk to strangers, and learned how to do some cold, hard out reach.

For the second, slightly less floppy, product, I built a job board to cater to LGBTQ+ folks in tech. This idea was fucking exciting. (If you're wondering how a job board could cater to this audience, I'll come back to that). I had never been so thrilled, it definitely ticked the founder-fit box. Aside from the founder-fit, what was partially so energizing about it was pride month in places like Toronto and San Francisco. It would have real traction potential. All those companies capitalizing on pride with rainbow logos were perfect for trying to sell to. But, what was I selling? Nothing really. My strategy was to get companies on there and then the LGBTQ+ folks, and then start charging companies. Out in Tech has a similar job board for allied companies, and they have like one hundred companies, so was this like the first flop? No, my board actually did have a unique value proposition: I would require companies to tell me things relevant to LGBTQ+ people, for example, whether or not their USA health insurance plan would cover same-sex spouses. Just as I suspected, most of the companies in my opening pitch would be quick to jump on the website. Someone even asked about pricing! However, A LOT of companies would drop interest after I asked my questions about what they do to support LGBTQ+ folks which was disappointing to say the least. Even though some companies did partner with me to be on the website, I only got a few companies setup on the website. So what happened? Pride month ended, and the PR value of the product died until next year (at least). I'm actually undecided about this product's "flop status". I still think I could work on it and build some minor traction until June 2021 where I can really hit the gas pedal. So did I learn anything? Yes, sort of, while most of what I did was cold out-reach and tapping my network, I also started using LinkedIn to find decision makers at companies, and I should have just threw out numbers when asked about pricing.

The third flop was less a product and more of a service. While I had been mucking around with past two projects, I had a fiverr account. The reason I messed up here was simple: I wrote some copy, and I had no idea how good this copy was because leads kept coming in to my fiverr account, but I didn't build the sales relationship! I created the fiverr account as a sort of backup in case I needed some cash. One thing huge, glaring, common theme among successful Indie Hackers is a lot of them were freelancers before being full-time business owners. So maybe I could do that despite the freelancing market being kind of tough on account of the whole pandemic going on. Looking back this could have been some good opportunity to build a freelancing business from the very beginning of my sabbatical.

After three months of sabbatical (messing around), I got spooked. Cash in my savings was dwindling, so I hopped on the job hunt. Maybe I could work at a startup, and wear all those hats I like to wear, and really just focus on delivering business value. Well that's sort of where I am now, I took a full-time position with a fintech startup near the beginning of August 2020.

A week after starting a full-time position, I wanted to get into the habit of working on something every morning before I got cracking at my day job. I started working on a method to display documents relevant to a particular task. After proving the concept was possible, I was at risk of building a hi-tech to-do list. Motivation dwindled again. I 'pivoted' my product, and I was going to make it a Jira Cloud add-on. However, motivation was still low, so I joined an online community of women makers called, well, Women Make because they had a challenge for the month of October. The challenge was named "Just f***ing ship it". A good extrinsic motivation hack is to give yourself a deadline, so I busted my ass every morning hacking away at this Jira add-on. I decided to call it FastGrasp because I'm awesome at names, apparently. Lucky for me, I did some "competitor analysis", and found top-selling document management add-ons for Jira. I believe FastGrasp to be a better solution, and did all the non-tech stuff to get it on the Atlassian Marketplace. I'm currently waiting on approval before I start my traction strategy which I'm sure I'll write about in another blog post.

The key takeaways here are be consistent, talk to customers, plan ahead, and timing is everything. I'm beginning to feel like a walking cliche.

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