It’s weird realizing someone I’ve never met has been a regular part of my life longer than my wife, but that’s the case with Bill Simmons.
I wasn’t even in college when I first heard Simmons’ old ESPN Podcast called The B.S. Report in 2007. A few months later, I picked up reading his column and became glued to any project he worked on: 30 for 30, Grantland and eventually his own site and podcasting network, The Ringer.
At that time, I got my sports knowledge from the main sources – ESPN, Sports Illustrated and the New York tabloids – but Simmons sticks out because he’s the first writer I can remember following that closely.
Sure, I remember some of the names that appeared on Around the Horn, listened to the guys on P.T.I. and caught the occasional Stephen A. Smith column in the Philadelphia Inquirer when I was in college, but Simmons was a ritual.
I became a Simmons disciple because he was real. In college, a few of us (who gave ourselves the nickname “The Braintrust” for some reason) would shoot the shit on sports and I always felt like Simmons would’ve fit right in.
On Tuesday, Simmons gave an hour-long talk as part of a weekly series presented by Inside the NBA host Ernie Johnson. Naturally, I was hooked to the Periscope. While many of the questions talked about different ideas for The Ringer, his thoughts on Tom Brady’s new home and when he’ll be streaming more video games with his son, Simmons offered advice that extends beyond the journalism industry.
Here were my takeaways:
Bet on yourself
“You’re going to hit points in life and hit forks in the road … If you believe you have something to offer, then you should bet on yourself.”
Maybe it’s because I’ve seen him do this for a decade or maybe it’s because of my current situation, but this hit home. Bill’s bet on himself a bunch of times – most recently when he started The Ringer after leaving ESPN in 2016.
If he could do it, why can’t I?
Try everything
“Not everything you do is going to work and that’s OK. Go full out into an idea when you have it… If we’re going to do this, let’s f***ing do this.”
*Checks my background*
A mini-concert series to highlight new artists? Check.
Different ways to present annual stories? Check.
An Instagram based on food in a fast food-obsessed county? Yup.
I’ve failed at things, too, but I’m proud of my approach here.
Be versatile and be you
Simmons is a great writer, an amazing interviewer and one of the top creative minds of my generation, but above all else, the Boston native is unapologetically himself. It might dilute a podcast when he spends 25 minutes on the Celtics, but if he were at the bar, I imagine he’d pull up a stool and give the same takes.
As a leader of two major publications, he took that brand identity and extended it to the groups’ content.
At The Ringer, he identified the company’s strongest subjects (sports and pop culture) and honed in on its niches (basketball and football as topics, well-written features for story formats). It’s what’s made the site a success for the last four years.
Simmons also mentioned how versatility became an attractive skillset in his hires.
“Learn how to do a bunch of different things – cut video, take photos, lead projects. Versatility is important behind the scenes… the more you are, the more valuable you’re going to be.”
It’s after he said this line towards the end of the recording that I found my “a-ha” moment.
For years, I felt like my versatility was a weakness – that opportunities were given to others because they were a strong writer or videographer and I was the utility piece.
But my versatility is a strong asset – something that separates me from the group and that makes me who I am.
Wherever it is that I work next, I plan on being me: The guy that when it hits the fan, people turned toward to get the job done because I can be plugged in and not miss a beat.