5 years later, I never thought I'd be renewing my business license
I was really inspired by Lynne Tye's post about being a lurker and thought I'd share a recent experience.
Five years ago I went to city hall to register a new business. It felt like a bit of a lark: I've got this app, it seems like it's got legs, let's check administrative boxes.
...and now, 5 years later, I just renewed that business license for another five years 🤘
I run Day of the Shirt. It gives super powers to super t-shirt shoppers. It started as a hobby project to help me find cool (and inexpensive!) pop-culture t-shirts and has grown up.
I never even set out to make money: a user emailed me to ask why I wasn't running affiliate links (I didn't know!) and that was the impetus to go from hobby to project to "product". Reframing that in my mind was also an impetus to think through customer support and monitoring and advertising. It required a major mindshift to go from bootstrapping (I built soooo many fire-and-forget projects in Drupal on shared hosting) to actually like, paying for stuff (Heroku, Intercom, Sentry).
I got lucky that my day-job evolved to track my side business skills as I went from a decade of doing Americorps and nonprofit management to being a San Francisco software engineer. It also kinda skewed my "how much money is enough money?" mindset, but I try to keep my focus on "am I still learning and feeling fulfilled?"
This is my first post 🎉 and I'd love to chat more about my experience. I see the form is telling me to consider making this an article, but I'm not sure what to focus on. Would love the feedback. Thanks!
Hi Ben, Lynne here 🙋🏻. Congratulations on everything!!! Leaving your lurker status behind, renewing your license, having a hobby transform into a product!!! I'd love to hear more about how you transitioned from a project to a product, what challenges you faced and overcame, and what you're currently working on. Are you going to work on Day of the Shirt full time? How did you transition from Americorps to SF software engineer?
Ps. I'm always asking, "Am I still learning and feeling fulfilled?" I swear, this is the key to happiness and therefore success. 🙌
Hey!! 🙋♂️
Great questions!
Transition from "project" to "product" was interesting. At that time in my life I was doing tons of little scratch-my-itch projects. My passion is UX, so I put a lot of polish into the experience of using them, and not so much technical complexity. I think this helped in that I could put something together over a few weeks, and then let it just continue running on the internet.
The big shift from project to product was seeing a feedback loop develop between other people who were using it (not me), their suggestions, and then me making a change in response. That was things like "oops, a typo", to "it's broken" to "These two shirts appear to be the same price on your website, but one merchant has free shipping and the other has $10 shipping. That's annoying."
My ability to respond to these things then evolved with how I ran the website. From moving from a bunch of PHP scripts to rebuilding on Ruby on Rails. And going from email to Intercom. And becoming more deliberate in collecting feedback in a backlog.
I think the biggest challenge has been in prioritizing and emotion. When building for myself, there isn't much emotional labor about whether I'm spending time on the right thing or framing it correctly or even "should I be coding or marketing?" But now people are asking things of me and I want to please them, and sometimes (often?) I can't both because of my scale (one person and the occasional contractor and my wife) or where I perceive the sweet spot of the product to be.
I'd love to work Day of the Shirt full time, but financially I think it makes more sense to keep it as supplemental rather than primary. (oh and the fear of course).
Transitioning from nonprofit to software engineer was interesting. I'd always been geeky; I grew up in the era of geocities websites and as I entered the workforce I kinda went from being the young guy who could help with the website, to the person pushing for strategic communications, to the person who would build out the project tracking systems. I did some contract work too, but I identified with the mission and getting the work done. The technology was just the tools I used to help me as a program manager.
Then I lost my job and was looking at various options and there was a fellowship in San Francisco that was "tech for good" so it seemed in my wheelhouse. I moved out there with my girlfriend (now wife). I think she was actually the biggest motivator to reframe myself as a software engineer. She got a job in technical recruiting and learned a lot about the tech industry and was like "Ben, you know all the stuff these people do; and the pay and benefits are great." When my fellowship ended, she was able to help me rework my resume (emphasizing the tech stuff) and a couple interviews later I was a software engineer. 🚀
Just followed you on Twitter 👋
Ps. You just wrote the first draft of your first IH article 😉
This is a great story. I echo your sentiments re: building for others.
On Sunday, I'm launching a weekly newsletter where I combine a powerful story with an inspirational quote to serve as motivation -- do you mind if I share your transition to kick off the series?
Whoah! Yes! 🙌
Sign me up! 💌
Excellent -- if you happen to turn it into an article before the weekend, I'll link to that versus this thread.
I will do that! Are you interested more in the project -> product story, or in my "how I went from nonprofiteer to software engineer?"
Feels greedy to say, but both? I think if you appended this response to your initial post with a suitable transition to connect the two, it would be an excellent read.
If I had to pick one, I like the latter -- specifically the "Ben, you know all the stuff these people do" aspect of the journey. A lot of times we need an external reminder of how far we've already come.
Hey Ben.
I'd love for someone on IH to do a really deep dive on how they manage their side business in a structured way. I haven't run a true "side business" since starting a similar eCommerce business in university a bunch of years back.
how much time do you need to carve out every week to work on the business
any tips for staying on top of customer service as the business grows
any thoughts about how to manage the business finances alongside personal finances? Do you just leave it all in the business, pull some out as a "bonus" once in a while, etc.
how to not feel like you're leading a double life at work
Just some thought starters in case they inspire more writing.
Thanks for sharing!
Whoah, those are awesome questions!
I just wrote up a long braindumpy draft. Would you mind taking a look and leaving some comments? Then I could post it as an article for further discussion.
https://docs.google.com/document/d/1R7Ciru6vluRwxSSPYu2UJTwGF7_z2-yE4OdghmLeaDc/edit?usp=sharing
Done. Have a look.
Quick question, did you scroll down below the graphic on the 2nd page of the doc? I noticed all of the comments were focused on the first page and I just wanted to double check that you saw the other
4 pages 😊
whoa..... totally missed that. Will drop some more comments in. You probably have a bunch of articles, blogs, etc. tied up in here. It's cool to help tease it out.
Congrats on your first post - and happy new year!
I am curious to learn more about the mechanics of your app. I see on the about page that you're sourcing shirts from 40+ sites. How are you going about collecting the data? Are they providing you with feeds or are you scraping from the "popular" sections (for example)?
Thanks! Happy new year! 🎉
It's all webscraping. I focus mainly on daily and weekly sales, so it's just checking a relatively small number of webpages and I don't have to do any true crawling.
Maybe as a datapoint, I also run Day of the Sock but turns out that's a totally different business. Most sock designs come out quarterly, so there is rarely something "new".
I'm always looking at how other daily deals websites curate and present products. Anything you check regularly?
That makes sense. And no, nothing that I check. I try to stay away from deals sites to save the few pennies I have lol.
Speaking of data, your insights feature is a nice touch. I'm sure you have some interesting data to play with.