My Story as a Homeless Developer

Hey Jesse, pick up a solar panel. You can get waterproof two usb port that'll crank out 20-30 watts ~$50. I'd recommend an ARM laptop too. They're cheaper and Intel is generally too power hungry anyway. A Samsung Chromebook Plus used on swappa would be really nice. It has a really bright display so you can still see it outdoors in the sun. For data, T-Mo is unlimited for $30/mo pre-paid.

Put your panel in the sun, sit in the shade at a park, tether your phone for internet, and you're golden. You can strap the panel to your backpack and charge on the move too.

As a cleaner myself I'd suggest him building up a small round anywhere there's retired folks. He'd need a small ladder, a stepladder, squeegee and applicator, bucket, cloths. The problem isn't really the capital costs - just having attention to detail, observing for good working techniques, being patient, polite and once you're seen actively working in the neighbourhood people begin to start offering you all sorts of odd jobs.

I say this because I think some times people from middle class families identify so strongly as 'software person' it detracts from other possibilities when they're stuck for $$$.

Shelter: Get a van. Live in it. Boondocking is better than the cardboard box or couch surfing.

Food: Noodles. Vegetables. Rice. Chicken.

Tech: android tablets can run Linux and can support mouse and keyboard. Tablets are easier than laptops to charge. Laptops can do more. Trade offs.

Security: get some money into bank account ASAP. Make it a regular habit. Any money you’d put into alcohol etc put it into bank account. This is your safety net. Start from zero.

Street address: get a mailing address. Parents/friends may be able to help. You only need to visit. post office box can help as well but costs money.

Relationships: be careful. Your safety net is likely not strong enough to tolerate much failure. Counter argument: having someone else around can help in little ways.

Decisions: think critically. Need versus Want.

Mental health: read autobiographies. Read fiction. Read. Improve all gaps that seem easy to fix. Understand that homelessness is a hole you can dig yourself out of.

Health: teeth, hair etc hygiene is king. Drop any kind of drug other than coffee. Alcohol etc will make you an easy target.

Small steps.

I have a startup that went through some very low lows. I had just quit my cushy job and had saved enough money to last for 2 years, but not my co-founders. When we ran through our funding, things became harsh. I funded everything out of my pocket.

The CTO couldn't afford his apartment anymore so I paid for his rent. Not long after, I got a family emergency and couldn't afford it anything anymore. I told him to get a part time job to help out. He squarely told me no. "Every successful startup founder lived in a van and dined on Ramen."

I stopped paying his rent. He moved into the office. I urged him to get a job because I couldn't afford it anymore. He refused. I stopped paying the office rent. He went homeless.

He lived on the generosity of strangers, though he went days without eating. He refused to get a job. As long as someone was helping him, he wouldn't work. We had to trick him to help him, a friend gave him some space to live together, then later told him that he needs to participate on paying rent. Only then he started looking for work.

There are a lot of conflicts the OP only mentioned in passing and didn't go into details. There is a lot more to this story, maybe the mental health issue nullify anything I say here. But thinking your story is like that of every unicorn tech founder can lead you to make terrible decisions.

Sometimes you have to be humble and make sacrifices to be able to move forward.