At the time that I read the question, our team was about a month away from closing on our seed round of investment after having bootstrapped for the past few years, so I definitely had a few thoughts about what it would take to bootstrap out to investment.
So many times we want the dream but don't want what it takes to get there. It isn't just about having a great idea for a business or being talented or smart enough to make that idea into reality. It's also about being scrappy enough to survive the valleys and determined enough to remove the barriers that inevitably arise.
So here is my letter to future entrepreneurs who want to know how to pay bills without a day job while building their company:
Whether you're actually broke or not, live like you are. Stop going out to eat, cut perks and recurring bills that aren't vital, and decide that streaming Netflix is the closest you are getting to a movie date night.
Put off expenses for repairs for things that are conveniences. Unless you're handy with fixing appliances, if the dishwasher stops working, know that bleach, dish soap, and elbow grease work just fine.
And when you are actually broke, get a job that covers the bills but doesn't leave you so exhausted or with so little time that you can't work on your startup.
If you have co-founders or a team and are preproduct and prerevenue, find work for hire and contracts that are still within your industry to pay overhead and your burn rate while some of your team continues to focus on the work of your startup.
Decide the lifestyle you want is the one where you spend every possible moment getting out to revenue--and understand that getting out to revenue is not always on the same path as getting out to investment.
Unless you are certain your team and product are ideal for investors, go for revenue first. It will defray expenses and prove your business concept or drive you toward necessary pivots to find the revenue in your proposition.
If you have a family, yes, it is stressful to continually say no to family vacations, shopping trips, or nice presents, but it will also help your kids get real really fast. Your teens will learn they can live without a continual stream of new stuff and that they can get a job to buy the stuff they do want.
If you're married to someone who isn't willing to deal with this kind of sacrifice (because it will always take longer and cost more to launch a startup than you ever think it will), weigh it long and hard before you start your company.
Understand your spouse's fears are valid and that the financial sacrifices your family will have to make will create strain in the relationship--as will your own lack of emotional and mental reservoirs for your personal relationships owing to the pressures and worries you now have about building your business.
And if you're dating, well, good luck with that. If you find someone willing to take the leftovers of your time, not get nice gifts, or go to nice restaurants, who is happy with all of your conversations being about whatever problem you're currently trying to solve, well, you've either found the perfect person or you're dating someone who doesn't want to be alone but is just as emotionally and mentally unavailable as you are now that you're focused on your startup.
A lot of founders give up their day jobs too early, not having realized the extent of the personal and financial toll entrepreneurship can take. It is a huge sacrifice, financially and personally. You have to want to succeed, to see your idea to fruition worse than you want anything else.
But the truth of it is this: Most who survive the trial by fire we call entrepreneurship wouldn't ever trade it for the security of a day job working for someone else.