Ask HN: Advice for turning my side project into a real business

Business Attorney Here.

I would speak to an attorney to see your next steps both in terms of setting up your business for success as well as making sure there are no issues with your current employment.

TinySeed only works with B2B companies, and based on your comment history it looks like this would be B2C.

I think your best bet would be trying to raise a pre-seed round if you wanted to bring in outside funding.

For any 20+ years-old readers here, if you ever think/dream about starting a business, you should learn from OP that cash and savings is paramount for freedom and creating a business later on.

> product-focused dev with 10 years experience at a-list startups [...] I don’t have enough cash saved up for significant runway. I’m 35 with family and living in the US.

The earlier you start, the more you accumulate, the more flexibility you have later. I had 12 months runway when I started mine, and it is so valuable not to look for investors and just work on your product/company when you feel pretty confident.

I did this. I grew my project, Buttondown [https://buttondown.email] from high three figures to low five figures while doing it as a nights-and-weekends thing at Stripe and then quit to work on it full time. It was a great decision and I'm happy I did it! (I also did it, frankly, with significant runway in the bank if I needed it, and no dependents besides my wife so the tail risk of "this goes to zero and/or I hate it" was not particularly painful.)

My advice would be: it reads like you're commingling two questions that really should be separate, which are:

1. Do you want to start a business and pursue independent employment?

2. What are the quantitative parameters and conditions under which such an enterprise is sustainable?

If the answer for 1. is yes (and interrogate yourself a bit! how many of the things that you are imagining are less "working on your side project full-time" and more "not working on the day job that you hate?"), get as concrete as possible with 2. What burn rate _is_ acceptable to you? How much savings are you willing to use during build-out, if you were to start now? What growth do you need to hit to feel like you're financially on the right track?

There are lots of funding tools (using the term 'tool' loosely) available to you — SBA, subsidy via full-time job, subsidy via contracting, lifestyle-friendly firms like Tinyseed. But you need to start with the numbers.

(Also always happy to chat more: I'm at justin@buttondown.email.)

I was you about a decade ago... I can't stress enough that if you don't have serious money in the bank or rich friends, you need to keep your day job and bootstrap. One approach I've seen work well even though it may be slow and frustrating - use the proceeds from your day job to hire a developer to do the work. You create the work plan, let someone else fill in the gaps. You focus on marketing / customer interaction to grow the product. Alternatively, keep burnin the midnight oil.

I do not recommend anything that smells like a "loan." This is speculative stuff you are doing, and a loan means you'll be on the hook to pay it back regardless of how it works out.