Month 1: From startup to small business

Figuring out what I'm doing, starting an Etsy store, and getting my first customer.

What’s this Substack about?

Back in 2020, I raised pre-seed VC investment and founded a startup. It failed unspectacularily.

Since then, I’ve been working as a Product Manager at another startup. It wasn’t long before I felt that nagging itch to build something of my own again.

I didn’t want to repeat the same mistakes I made last time — I documented those in my Medium article “I’m Starting a New Business After My Last Startup Failed — Here’s What I’m Doing Differently”.

One of those mistakes was not sharing the journey. So here we are.

The idea

The idea itself has been on my mind since at least 2019 when I created a hand-illustrated picturebook for my nephew’s first birthday. It featured him in his iconic outfits, with all his different food experiences. It was hyper-personalised and unique to him, making it that much more special for him and his parents.

I wanted to see if other people were as interested in ‘hyper-personalised children’s books’ like the ones I created for him. This isn’t a novel idea at all — there are plenty of businesses selling personalisable storybooks. But this time I’m happy to focus on entering an existing market, instead of attempting to create a new one (like I did with my failed startup).

I don’t see competition as a deterrant — but as proof that a market exists for my product.

What’s my goal?

If you were hoping to hear about my next “billion dollar idea” then I’m sorry — this blog probably isn’t for you.

I’m happy to admit my goals are (a tad) humbler now. Some people will say I’ve lost my ambition — I wouldn’t disagree. But right now, I’m preoccupied with the idea of building a purposeful business that gives me freedom — creative freedom, freedom from relying on a 9-5, and ideally one day, financial freedom. My plan is to build this business while managing my day job as a PM.

Along the way, I’m curious to explore how AI will play out in the creative industry. I think it’s fair to say AI tools like Midjourney and Dall-E have so far left a net negative impact among the artist community. Something about it feels… soul-less and wrong. Why are we so intent on using AI to replace artists rather than empower them? What’s the happy medium here?

Unfortunately I have no answers (yet)— but I’m hoping I’ll figure it out along the way.

Starting on Etsy

Putting in the 50-100 hours to create an entire hyper-personalised children’s book before having a single customer ready to buy it felt like a recipe for disappointment. I needed to figure out a distribution channel first. Etsy came to mind as a good starting point.

I decided to niche down and settle on a simple “custom cartoon digital portrait from photo” listing. This would require no logistics, was repeatable, and I knew I could do a decent job. I also saw other Etsy sellers getting decent sales from similar ideas — but none that was similar to my particular style, so at least I would have a differentiator.

My first Etsy listing

Services felt easier to sell than products at first. The idea would be to start with high-effort hands-on digital portraits, and over time, automate and use templates as I built up more of a portfolio.

My first real customer 🚀

My guess was I’d need to build some social credibility before anyone would be willing to buy from me. So, I did what most people probably do — I asked my friends and family to be my first customers and leave me some 5* reviews to bootstrap my ratings. From there, my plan was to trial ads to get traffic to my store.

Instead roughly ~3 weeks after my listing going live, I unexpectedly got my first sale!

😱

There’s no feeling quite like making your first sale.

What I learnt from my first sale

To be honest, it was a $20 sale for ~2.5 hours of my time, which makes for a terrible trade on paper.

However, my goal here is simply to build traction (following the infamous YC “Do things that don’t scale” advice, if you will). Traction not just for my Etsy store, but also my timid self who hasn’t put herself out there in the creative world for quite some time, and had been sheltered from real feedback from real customers for the last year with a 9-5 job.

P.S. I also think new shops are given a big ‘boost’ by Etsy. I had a flurry of people adding my listing to their ‘Favourites’ in the first week, but visits to my shop dropped sharply after that.

Where else could this lead?

The irony is my “best” ideas only seem to come after I’ve already committed to starting a project, and end up threatening to distract me from it.

Some of these included:

• Baby Board Books — these are a very simple trending category of children’s books that I discovered via the Etsy marktplace. It also seems to be a non-competitive category, with very few listings that offer any customisation beyond a name.

• Physical prints — provided customers are willing to absorb the extra cost.

• Etsy OS — build out my own systems, integrations, and content related to selling on Etsy, and sell those.

• Design Agency — using the landing page I’d build for my own site, I could also have it promote my Webflow design services and open up options to work as a freelancer.

How am I feeling?

I’m most excited about the process of optimising and experimenting — with the listing, products, marketing channels, pricing etc. I’m truly enjoying the feeling of “living off the land” — making and spending money (however little) that was directly made off of my skills.

Truth be told, I don’t have a clear step-by-step plan on how to build this business — just a goal of where I want it to head.

For now my plan is to write monthly retros here on Substack, and figure things out as I go.

Until next month 👋

Joy