There is no “I” in team

Trust me, as an entrepreneur I struggled to build and scale a team. I always ran bootstrapped companies, so it wasn’t always the team I wanted, it was the team I could afford. It is not an unusual dynamic and probably not that special to me. 

When I hired people in the past, I always warned them that eventually the business will move fast. It will be like a wave. The surfers that are prepared will stand up and ride an amazing wave and make it all the way to shore. Many will wipe out, and some of those will be prepared, yet external forces out of their control will

wash them out. For my company, when we acquired other companies, it wasn’t that my people always stayed. If we had duplicated skills, like a controller, we had to pick one. In a lot of cases it wasn’t black and white. For the unprepared, it was simple. They missed the wave and either got left behind or drifted out to sea. This analogy served me well as the CEO of my own company. As an investor, it’s more about coaching the founder. 

This past weekend I was messaging with a founder. He shared that he is really struggling with hiring and when I asked what type of people he wanted to hire, he sounded like I did as a young entrepreneur. High expectations with very little budget, but that he could train them. He may or may not be reading this, but felt my thread to be meaningful, but maybe I was being self indulgent. Of course via messaging, profound concepts don’t always land. 

He is a fit person. I asked him (with no context), had he ever run a marathon. He said yes (I was unsurprised). I told him that I am aspiring to run a marathon and could he train me. I asked him if he had ever trained anyone, he said no, but was optimistic that if I followed the method that worked for him that I would be fine. So then I asked, how long do I need to train, I don’t have a lot of extra time. He said we would have to figure it out. Well, my thumbs were hurting at this point so I let him in on it. 

Dude, I’m a 53 yo fairly sedintary

man that has no business training for a marathon and if I did, it would take him years. Why? I am not him and I have no ambition to run a marathon. So what’s the point?

If you are starting a marathon team (not sure if that exists), would you bring people on board that have never done it, you have no experience training and whose ambition could be suspect?

Hiring for your startup is not that different. Many people, especially me have made poor hires. Sometimes it was because I didn’t really understand what the position needed, but a lot of

times it was what I could afford. Another dynamic with less experienced people that are willing to join, may in fact be ambitious. Their ambition is that you are going to invest in them and give them new opportunities. A person with great experience has many options and will join you because their ambition is in being wildly successful leveraging what you have built so far. 

As we enter the holiday season, maybe you can find space to think about your team. If you are working for a founder, maybe now is the time to be realistic as to why you haven’t been as successful as you thought you would at the startup.