It’s a huge risk. A lot of “pretty successful” startups all sell at about the same point in time … about 5 years in. Because the founders get just too burnt out around Year 4 … and as Year 5 rolls in, they’ll sell. Often, as it’s just getting good.
My Top 10 suggestions:
- Hire than Extra VP — a True Owner. Don’t try to save a few nickels here. You’re responsible for everything as it is. But you have to own less as you scale. Find 1 or 2 or 3 truly great VPs that will own their functional area. That will take so much of the mental burden off your plate.
- Hire a COO. This is a quirky, odd hire, but try to do it anyway. Find someone that can own 20%–40% of the company’s operations.
- Fly Business Class, Stay in Decent Hotels (Once You Can). I know we all don’t want to do this. But travel takes its toll. The CEO shouldn’t have back pains after spending 3 weeks on the road. That doesn’t help. Making travel less literally painful is a high ROI investment, at least after you are at scale and have a few bucks in the bank.
- Take Your Vacations. Take 2 weeks a year and go somewhere. Check email twice a day, but that’s it. No Staycations.
- Find A Mentor, A Real One. Someone you can talk to this stuff about. For real. Pay them fairly (probably equity).
- Raise A Few Extra Bucks. If you are venture-backed, raise 20% more than you planned. This will destress your life a lot, IF you don’t increase your burn rate or spend it.
- Don’t Take It Home, After Year One. After the first year, the stress and drama of a startup will be too much on your family. Don’t overshare here after the early days. You need Home to be about your family and a place to destress. Your family — they can’t take the constant drama, it’s too much for almost anyone. They will tune out. Share what you need to share after Year One, but be careful about bringing it all home.
- Burn Less. Controlling your own destiny is something wonderful. Even if you can raise a venture round, don’t spend it all. Don’t be dependent on third parties for life support one day longer than you have to. This won’t turn a frown upside down, per se. But it will be incredibly liberating.
- Grow Faster (Sometimes). Sometimes, growing faster often is actually less stressful. If you grow too slowly, the resources won’t be there. Everything will slow down. Hiring gets harder. Press gets harder. Customer and partner attention get harder. Sometimes, growing slower is less stressful. But often, it is more stressful over the long term.
- Focus on Happy Customers. So many things are so hard. But everyone can improve customer happiness. Drive that up, including NPS and CSAT, even if you are out of other ideas. This in the long run will destress you. High churn is very stressful in the long run (although it doesn’t feel that way in the short term).