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:
Investing in personal presence.
Amidst all these valuable lessons, No. 5 resonated with me the most. So in 2017, I'm making an effort to "dress one level up." As a serial entrepreneur, I’ve recently been thinking about how I can establish a more mature image. Last year, I spoke at more than 10 conferences and traveled two to three times a month to attend 100-plus client and investor meetings.
I know it’s paramount to develop a personal presence that commands authority and respect. Still, style isn’t something I think about very often. Lucky for me, I got introduced to Bombfell -- a convenient subscription service whose professional stylists hand-select clothing based on a client’s profile and taste. All the items fit within my price range, and I spent zero time worrying about what to wear. The experience has changed the way I think about my style.
Seeing and feeling the difference it makes.
A recent industry event in New York presented the opportunity for an in-person meeting with the CMO of Neiman Marcus and the CIO of DSW. These are experienced senior executives at large companies, and I wanted to make sure I presented myself in the best possible way. I sought Bombfell’s help again to ensure I’d “dress to impress.”
This time, the stylist combined colors and patterns I’d never considered. I was surprised to discover I felt even more confident for my meetings. I wasn’t the only one who noticed. At the same event, I ran into Bob Schwartz, Nordstrom.com’s former President and someone I’ve known for several years. “What happened to you?” he asked. “Looking sharp!” I couldn’t stop thinking, “This is going to be a great day.”
Inspired by the differences I was seeing (and feeling), I uploaded a new profile photo on LinkedIn. Check out the progression.
Prioritizing the personal brand.
The Bombfell makeover felt transformational -- especially for someone who’d never thought too hard about personal presentation and cut his own hair. I never would’ve suspected that better-fitting suit jacket would make me look more energetic and “CEO-like.” There were psychological benefits, too. I noticed that I felt more confident and prepared when I also thought, “I look good!”
For many entrepreneurs, dressing a level up might not rank very high on the list of priorities. I get it. Building a company demands an incredible amount of energy and emotion, not to mention time. It’s easy to think, “I have more important things to worry about.”
I’m telling you, it matters.
Learning from those who do it right.
One of my biggest realizations is that looking the part helps others see me in the leadership role I'm striving to attain and promote. If you want to be an influential decision-maker in your organization, dress like one. There’s a lot of truth in the old saying about dressing for the job you want, not the one you have.
Today’s most successful leaders dress one level up. Need an example? Prior to Facebook’s IPO, founder Mark Zuckerberg was known for his hoodie. When’s the last time you saw a photo of him wearing one? I’ve asked my sales team to pay extra attention to their professional presence whenever they have an in-person meeting. We can help shape how others perceive us, if we make the effort.
Thanks to a friend's advice, my 2017 is off to a good start. I’ve got a new profile pic, several good meetings behind me and a new wardrobe to help project the persona I want others to see.
I challenge you to do the same. It will do wonders for your career in the year ahead. Don’t be surprised if you feel different – like a better version of yourself. Good luck!