Over the years, I’ve had the privilege of speaking to many college classes.
It can be a humbling experience. I’m now more than twice their age and when I talk about the start of my career — which I swear was only yesterday — most of them weren’t even born yet. It’s hard not to feel like a real life Steve Buscemi “How Do You Do, Fellow Kids?” meme.
Still, it’s an opportunity I enjoy because I view it as a chance to teach the students about the realities of digital media and journalism. I’ve experienced a lot of highs as well as some lows. I’ve always viewed the lows as an acceptable tradeoff for the highs and I try to make the students understand they will have to make the same bargain.
I also like to think I can help them avoid some of the mistakes that I’ve made, which might help them enjoy their careers and achieve even greater success than I have.
So when they asked how to get started in the business, my first piece of advice never changes.
“Start an email list.”
When?
“Yesterday.”
What should I write about?
“It doesn’t matter if you don’t know what you want to write about.”
“Heck, it doesn’t matter if the only people subscribed at first are your best friends and your grandmas.”
Start the email list now.
If they’ve yet to identify a chosen interest or career path, I tell them to send out a list of books they’re reading. Or a recipe for their favorite chicken wings. Or a column on why they think Season Two of The Wire is the best or worst season of The Wire.
Send out anything.
Send it out tomorrow.
The best investment anyone they can make for their career is to get people invested in them and the earlier the better.
Also, if they’ve never seen The Wire, they should do that, too.
Here is a picture of me talking to a class from the University of Iowa on an unseasonably warm January day in the beautiful city of Chicago. No, I did not pay them to look interested.
Why an email list matters
The nice thing about this advice is that it takes less than 30 seconds to explain to a class of college kids and even less for them to make sense of it.
The explanation is this: Email is the only way to keep an audience over the course of your career. You may change employers many times. Social media platforms will come and go. Algorithms can change your visibility in an instant.
But email is forever.
And with an email list, you’re never starting from zero.
Plus, if your email list is big enough these days, you may no longer need to depend on an employer or fighting for attention on social media.
That’s the dream, anyway.
And so I tell the students to start gathering the best way to contact their audience as they start the journey.
Though not perfect, a healthy and strong email list is the backbone of success if you’re trying to build a YouTube channel, podcast network, website.
It will also grow into an invaluable way to push your various monetization channels (merch, events, memberships).
Newsletters are for anyone. Journalists, chefs, influencers, digital creators, politicians, engineers, teachers … anyone who goes through this life depending on the support of other people which is just about everyone.
Heck, even Tom Brady has a newsletter, though I cannot credit the newsletter with any of his seven Super Bowl rings. (I wish I could.)
Do As I Say, Not As I Do
And yet while I was preaching the virtue of the newsletter to impressionable young minds, it was not advice I was actually following myself.
I’ve built plenty of newsletters for my employers and even had my own moderately successful Chicago sports newsletter named Midway Minute that was acquired by my last employer. We used that list to launch our inbox communications with Chicago sports fans.
But as far as a newsletter designed for people interested in what I was doing or thinking? Nope.
I don’t have any excuses, particularly during these last 7-8 years when it has become exponentially easier for regular people to build email-focused platforms at places like Beehiiv, Substack or Kit.
At the time, I told myself that I was too busy. And I was. Building a sports media outlet from the ground up in Chicago was an all-consuming task as was innovating blogs, podcasts and newsletters at Yahoo Sports a decade earlier. Plus the paychecks were steady and I had little reason to worry. I got too comfortable in a field where the next paycheck should ever be taken for granted.
Both spots were exactly where I should have been building an audience of fans and communicating with them directly, even if I was just occasionally sending out links to my work with a simple greeting and stray thought. Both outlets were exciting products and featured sizable audiences, parts of which I could have seamlessly continued to address once market conditions changed and I was laid off, through no fault of my own.
But as I enter the latest stage of my career, it’s not a mistake I will continue to make.
So welcome to my email list.
The best time to start this was 15 years ago.
The next best time is now.
My plans for this newsletter are fluid — launch first, answer questions later! – but you can expect me to share lots of thoughts about building in the digital media space, what I’m working on and maybe even a thought or two about Season Two of The Wire.
You should really watch The Wire.
Best,
Kevin
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