The “Rise” & The “Grind”
I remember coming into the office every day to an electric environment. So much energy, surrounded by super smart people. Everyone was excited. Crazy busy but excited. Hours felt like minutes. The feeling of tremendous growth and momentum. The promise of a bright future.
Contrast this with the “Grind”, where growth and momentum has disappeared. And regaining momentum is VERY hard. Just ask any startup or big company where this has happened. Turning this around is brutal. You are coming into the office where everyone is tired or worn out. You are in survival mode. People you respect are leaving for other places. You dread coming into work because you know there is probably more bad news. Or that you have to fix so much stuff that’s broken due to “startup debt.” This is the cultural, the organizational and technical issues that were overlooked during growth.
I was very fortunate to experience both in my career multiple times. The “Rise” at Alibris from May 1999 to September 2000 where we went from 18 people to 150 people. The “Grind” from September 2000 to February 2001, when we went to 110 people with the first lay off due to the Dotcom Bubble popping. I did not survive the 2nd culling which happened at the end of January 2001 where the company went down to like 75–80 people. Lesson learned, first things that get cut are marketing and customer service roles.
I experienced the “Rise” at Yahoo! Inc from 2001–2008 at the company overall and for my specific business group and region from 2008–2011. Unfortunately, what I learned here was that even if your P&L (Profit & Loss) of your Business group was great, it did not matter when the rest of the organization was in free fall. Yahoo!s nadir really started around 2009 with the loss of a tremendous amount of top talent at all levels and groups. It’s really tough when so many smart friends you have worked in the trenches with end up leaving. Looking back in retrospect, the end of Yahoo! was clear back in 2009. I remember the loss of momentum, and painfully low level of energy vividly whenever I was in our HQ in Sunnyvale. This was a MASSIVE contrast from my first 7–8 years there.
3rd times the charm right? I joined 500 Startups when we were ~30 people and saw this place boom to 150 people by mid 2017. This corresponded with a crazy amount of startup investment activity. Incredible time. All the learning, excitement, growth, surrounded by smart mission driven folks. Well, then mid-2017 hit and we were in survival mode. Those “Grind” years were really tough & stressful. I admit that. I am still processing this even after 9 months being out of the place. (This is why “Fallow Time” is important)
Both of these kinds of experiences are important to your career. You learn so much when a company scales quickly (and usually poorly). Most people are not lucky enough to see such crazy fast growth in their career. It’s like drinking from a firehouse. And it’s why you see people jump around to different companies and chase this growth throughout their careers. It’s not just about monetary rewards, although that is a very possible outcome. It’s about the excitement, the learning and fun from working with the tailwinds behind you.
But i would argue you probably learn as much from the “Grind” too. Maybe even more. You learn what you are made of. You learn what your values are and “What” matters to you. And as an executive you see all the things broken that were ignored during the high growth years and then you have to fix them. I don’t respect people who don’t stick around during the tough times to try to make things work. It shows a lack of commitment.
On the other hand, don’t do what I do and stick around much longer than you should. Loyalty only goes so far and you don’t want to go down with the ship. From a career perspective, you risk having your brand tarnished by staying at a sinking company too long.
This is where the “Goldilocks principle” comes into place: the “just about right” point in time to leave. This is something I have gotten wrong several times. And this is not a dig at any of these companies. Sometimes you just are not a fit anymore for where the company is going, or you are just too tired or burned out. And other times the company is also clearly toast and you see the writing on the wall. So take action accordingly and move on.