Ask HN: Advice on Startup Career (and Betrayals)

6 points by throwaway68102 5 years ago | 2 comments

I write this at a time when I’m at the lowest point of my self-employed software career (thus far in my life at least).

Long story short: I developed systems and processes - while in college for Comp Eng - for various small businesses and enabled them to bring in over a million in revenue cumulatively. I always planned on running my own businesses and as such, have been through a handful since graduation. I learn more and more with each "failure", and get farther on the next venture each time as a result.

However... These days, I find it very difficult to not only go through the usual routines of checking+responding to email, nonetheless actually improving or finishing my projects to see what could result (success?).

With the latest venture, my cofounders are attempting to leave me with nothing despite investing low 6-figures in capital and having legal share ownership (per a contract we all signed).

I can tell in my blood that entrepreneurship is what I want to do. I feel as though if I had a mentor who could use a (no self-brag intended) ambitious software engineer and thinker to build/empower projects, and we support each other in some way, that would be the dream. I know I’m capable of much bigger things than current, but clearly need mental repositioning and perhaps even a complete switch on what I’m working on.

Given the above, do you have any advice for a 20-something (nearing 30) that is tired and has been betrayed more than once in the startup game? A long read, I know. Have been trying to figure out my future path for many weeks now honestly. I greatly appreciate it.

11thEarlOfMar 5 years ago |

One approach (I'm assuming you're not married, if so, disregard):

Make a plan to work at a regular company for 3(?) years. Live frugally and save as much as you can.

During those 3 years do these things:

- Meet people. Specifically, technical people who are in other technical areas. Learn a little bit about what each of them does and how they do it.

- Treat your time away from your day job as time you're working for yourself. Develop ideas, flesh them out, build prototypes, maybe an MVP.

- Learn about corporate financial statements: P&Ls, Cash Flow, Balance sheet. This is important for analyzing your business ideas. Once you have a product or service concept, build a pro forma financial model and convince yourself whether the idea can fly as a business.

Once the 3 years is up, you'll have seen a broader variety of 'real world' problems to be solved, you'll have met people who you might leverage in establishing a business, you'll have a handful of ideas to choose from, and, you'll have savings to sustain you while you put your shoulders into it.

Importantly, don't force it, be patient and remain objective.

Good Luck!

throwaway68102 5 years ago | |

Thank you for these recommendations and the fresh perspective.