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We need more posts like this. The nuts and bolts of bootstrapping. Too many articles talking about what to do at step 43, need more about steps 2-5.

Speaking of, has anybody had success with rather than dumping the 9-5 and jumping straight into your startup, tried going contractor for a while and use the down time to work on the start-up?




Yes, me. Been doing it for a couple of months, although I started contracting 3 months ago.

Key points:

1. It's hard. Get a calendar and worship it.

2. It works only if:

A. Your contracting is earning enough to pay the bills. Otherwise you'll be stressed beyond belief (because you'll be failing at 2 things simultaneously).

B. You force non-contract time to do startup. Doing it on the side/evenings/weekends doesn't work. I average 3-4 days a week contracting and working on startup a bit daily with guaranteed 2-3 full days a week. Yes it eats into the weekend, but you'll be 100% ok with that!

Happy to talk more if you want by email. Drop me a line.


> The nuts and bolts of bootstrapping. Too many articles talking about what to do at step 43, need more about steps 2-5.

Step 1: Sell. Step 2: Sell. Step 3: Sell. Step 4: Build a little bit. Step 5: Sell some more. I made this mistake so fucking badly when I started in business, I'd build something then try to sell it. Don't do that. Get users, ideally paying users ASAP. Or at least get people to give you an email. Something. Anything. Don't build then try to sell, you're bringing a world of hurt upon yourself if you do (and getting locked into design/feature decisions that aren't what people want).


I consulted to pay the bills. It worked for me.

I think the three toughest things with the contracting approach are: 1. Being disciplined and actually working on your business. I don't have a great answer for this one. Just knuckle down. 2. It often takes a fair amount of time to generate consulting business. This is time that you aren't making money. 3. When consulting gets busy you eat into the time you have for your project and stop making progress and loose momentum.

What I did to deal with items 2 and 3 was get a long term, part time contract (3 days a week). I then had two full days a week to work on my business and rarely struggled with burn out or time conflicts.

I think this approach is a lot easier than straight up freelancing.




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