For me at least, 3 things made a material impact:
Add an “ex-post facto co-founder” and/or upgrade the management team. In my first start-up, my co-founder and I met for 20 minutes at the end of every single day, and had lunch as often as we could. 50% of this was just dealing with stress and unscripted issues. It helped each of us so much.
In my second start-up, I found this help more in my management team. Find at least one person on the team, later, that can share at least some of the burden with you. That cares so much about the company, that she can carry some of the stress as well. Find two like this — then they’ll really help carry you to the next level.
And sometimes, one of these additions to your management team can take on so much of the burden, she becomes like an after-the-fact co-founder.
Get to cash-flow positive. At EchoSign, we hit cash flow positive around $6m in ARR. One could argue if it was the “right” play or not — by staying that way, arguably, we underinvested in the business. But. It way de-stressed my life, to not have to worry about raising money ever again.
At least having the option here, at least being “cash flow break never”, can dramatically de-stress things.
Don’t look to your family, after the early days. This will lead to less stress. This may sound counterintuitive, but it isn’t. Your family can only deal with so much. You can lean on them a lot in the first 6 months. Share all your fears, your worries, your stress. But after that, let them off the hook. Don’t burden them with your stress after the initial starting up period. They won’t be able to handle it forever — no one can — and if you try to use them to help you, it will create a negative feedback loop.