Whenever I wear a button-down shirt to the office, someone asks, “Jerry, do you have an important meeting today?”
It’s a fair question. My wardrobe reflects where I’ve been — as founder of three companies and part of the startup community for the past eight years. My day-to-day look is a mix of T-shirts from my own businesses and those created by colleagues or friends. In fact, I have four of the same Retention Science t-shirts in my closet, and I wear one almost daily.
Not long ago, I got a wake-up call on the topic of “dressing up” to the next level. Mark Suster, a two-time entrepreneur-turned-prolific-venture-investor, shared with me how important it is to act and look the part I want to play. Here’s an image of his handwritten note: