Know Your Enemy: How Three Years at McKinsey Shaped My Second Startup

Summary

“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”I worked as an Associate Partner at McKinsey for three years before starting Meanwhile. Folks often find that surprising. I wasn’t the only YC graduate there but there weren’t many of us. I did this for both practical and aspirational reasons. Let me get the practical reasons out of the way: I wanted to make money and provide stability to my family after having worked four jobs in three years. McKinsey is prestigious.{1} I had never worked at a traditionally recognizable company, so I wanted to derisk my resume by working somewhere with high signaling.{2} The work was more interesting than {insert name brand tech company, and the people were, on average, more curious. Let me unpack the aspirational reason I joined. I wanted to understand my competition. I thought McKinsey would be a great way to see many concrete challenges inside large banks and insurers. I could then pick a problem to tackle in my next company. That didn’t quite work out exactly but I learned deeper truths about where startups can win and compete. A common criticism of McKinsey is that clients hire them to give answers they already know. It’s all just cover-your-ass. I am sure that happens (perhaps a lot), but in my ~25 engagements at McKinsey, I can honestly say that not once did I think the client already knew the answer. Most of my time was split across two types of projects: building new things inside incumbents and helping incumbents address deep-seated risk/compliance topics around or through technology.On the first, McKinsey has this practice called “Leap by McKinsey,” where a client hires them to build a new business unit, a new division, or a new “startup” within the company. I would go in and be the “entrepreneur in residence...