Recently, I spent several hours with a new but great friend who has been on a vaguely similar journey to me. This friend is one of the hardest working people in the industry. 20×7, near as I can tell. On jets. Investing at a breathtaking pace. Innundated with calls, Slacks, emails, and all the rest.
And he made an observation to me that I’d been thinking about for a very long time, but didn’t know how to express.
That we do all this for the Quality of Life.
But what does this mean? Start-ups are so, so hard. So hard. If you haven’t been a founder before, you really just can’t know how hard it is to create something from dirt and drag it to the first $1m in ARR. And then drag it right up that hill to $10m ARR. And then realize there — it’s just begun. You really can’t know how hard it is, even if you were a VP at a great start-up, even if you were the first employee, even.
In many ways, your Quality of Life will simply be awful. The pay is terrible. The risk isn’t worth it. You lose one critical employee, the world is over. Your competitor can destroy you in one release. You can’t raise the minimum capital necessary. There are never enough customers.
And yet …
When I look back at my professional start-up and founder life, there are three moments when my “Quality of Life” was the highest:
- First, for a brief window, when my first start-up as an exec IPO’d. I wasn’t a founder, but I’d been there since Day 0, and I felt like I’d made a real contribution to the success of something, that at least for a little while, was a Unicorn.
- Second, for the entire history of my first start-up as a founder. My first start-up, NanoGram Devices, was the hardest thing I’ve ever done in my life on every single level. Every day was impossible. We were doing something that truly had never been done before. And an industrial-grade CO2 laser was sitting just a few feet from my head, that if misaligned, would blow a hole through it and the entire building (I took that particular cube on purpose).
- Third, my second start-up as a founder — once we had a great management team. The phase from $2m to $12m ARR … once I had a great VPS, VP Product, VP Marketing, and VP Customer Success … that phase … and man it was hard … and I worked 24×7 … but my “Quality of Life” was so very, very. Very. High. Then … I sold.
And for the most part, these were incredibly stressful times, when I was very underpaid, overworked, and worked to the bone.
So what is Quality of Life, then, for folks like us at least?
I think maybe it’s the following:
- Getting to pick who you work with. This is just so, so much better than not getting to pick.
- Having a great founding team, and then, a great management team, to work together with. Sharing this adventure with an A+ team is just the most amazing thing. If you haven’t experienced this yet, you don’t know. In my first start-up as a founder, I had a great CTO and VPE and a pretty darn good VP Ops from the very beginning. I had a pretty excellent, extremely committed co-founder AND management team on Day 0. That made all the difference. That made the insane trips, the near loss of all our customers, the devastating failures … all still somehow consistent with a High Quality of Life. My second time as a founder, it took me 36 months to put together a true, real management team. That was an epic mistake. But once I did … Quality of Life became very high. Even though the challenges were just as great.
- Being great. Not just being part of something great — but, Being Great. We have to be great. In some way. A great company. A great team. A great investor. Whatever. We’re the type of folks that need to be in an environment where we not just make decent money, not just have a “good job” … but an environment where we can be Great.
I know this type of High Quality of (Start-Up) Life can also be incredibly trying. But once you’ve experienced it … you can never go back.
And if you haven’t had this experience yet … three pieces of advice, that we’ve touched on before:
- One, if you don’t have a great co-founder yet (even if she’s great on paper) … WAIT. Do not pass go. Be more patient. Your quality of life will simply be awful if your co-founders aren’t as committed as you, and if they aren’t at least close to as good as you.
- Second, hire the best management team you can as early as you can. SaaS is so cross-functional. Yes, you need to sell it first yourself. You need to prove out your MSP. But don’t wait a moment after that to hire the best senior help you can.
- And third, find something you, your company and your product are truly great at. I know a lot of your product isn’t great yet. But make sure there’s one thing everyone believes you are 10x better than everyone else in. We can all rally around that, and fix the rest of the stuff. Because real start-up people want to work at something great. Even if the definition of “great” will change at each stage, and over time.
I know this isn’t sitting-on-the-beach in Kauai Quality of Life. It’s nothing like that.
But deep down, beyond the pain and struggles … maybe it’s even better.
For people like us, at least.