#35 - CEO of Barstool Sports Erika Ayers Badan
Jan 30, 2024
The CEO of Barstool Sports Erika Ayers Badan is on Guyset today!
This episode is filled with some of the most honest and genuine career advice I’ve ever heard in a way that will truly resonate with anyone. We talk about Erika's announcement that she’s leaving as the CEO of Barstool Sports, first jobs, Dave Portnoy, how to approach conversations with your boss, Call Her Daddy, what to do if you’re not getting job interviews, her upcoming book “Nobody Cares About Your Career", what’s next for her after Barstool, and so much more.
How to Actually Build a Career in Your 20s: Lessons from Barstool Sports's CEO
From Guyset Podcast - A Guy's Guide to What Should Be Talked About
What if I told you the CEO of Barstool Sports spent an hour sharing her most honest career advice? That's exactly what happened when Erika Ayers Badon, CEO of Barstool Sports, sat down to discuss everything from finding your first job to knowing when to quit.
This isn't your typical sanitized business advice. This is real, unfiltered wisdom from someone who built her career by taking risks, making mistakes, and never being afraid to fail.
It Doesn't Matter Where You Start
Erika's First Job Reality Check: Started as a legal assistant at Fidelity making $50,000. Had an office. Looked successful on paper. But she was miserable.
The Bold Move: Left to join the advertising group. Took a massive pay cut from $50,000 to $17,000. Racked up debt. But it was the best decision she ever made.
Why It Worked: She ended up in a creative environment, worked with inspiring women, and got assigned to "the internet" because nobody else wanted it. Sometimes the job nobody wants becomes your biggest opportunity.
The Lesson: Don't get trapped by what looks good on paper. If you're not learning and growing, "you have to get the fuck out."
Knowing When to Leave (And How to Do It)
The Internal Signal
"You know inside of you when to leave a job. Everybody knows. It's like when do you leave a relationship? You know how you feel about your stuff."
The hard part isn't knowing—it's acting on what you know.
The Real Work
Looking for a job is "a second job on top of your first job." Most people are too lazy to make a change. That's what separates winners from the status quo.
Having "The Conversation"
Before you talk to your boss:
Get your shit together
Don't be scared of your boss
Build a relationship first through consistent, proactive work
During the conversation:
Show gratitude for opportunities given
Explain your decision with respect
Share your vision for what's next
Never bash the company or people
What NOT to do:
Don't go in small
Don't say you hate your boss or coworkers
Don't trash the company
Building a Relationship with Your Boss
The Foundation: Don't be afraid of the person you work for. Work your ass off, get in front of them, deliver value.
The Mindset: Don't be about yourself. Be about whatever your boss is trying to create or do.
The Benefit: When you establish this rhythm, leaving becomes a more comfortable conversation.
The Reality of Your 20s Career
Work Your Ass Off
"I think in your 20s, you should work your ass off. Make sure you're getting as much opportunity as possible and learning from as many people as possible."
Embrace Failure
"If you do not fail and try so much in your 20s and 30s, you will become calcified by the time you're in your 40s. The people around me who are afraid to fall—they're dead."
The Promotion Myth
The expectation that you get a raise and promotion every year is "kind of a new phenomenon." Be realistic about what you deserve.
Before asking for a promotion:
Stack rank yourself against peers
Be honest about whether you deserve it
Consider the company's financial state
Come prepared with what you've accomplished
Have a vision for future work, not just recognition for past work
Content Creation and Standing Out
Volume is Key
"You have to be a volume shooter. You have to post, you have to be insanely prolific."
The Sacrifice
"If you are the Red Sox guy and the Red Sox are playing, you gotta be home covering the Red Sox. You lose your credibility on the internet instantly if you're not on it."
Breaking Through the Noise
Getting hired at Barstool (or any competitive company):
One application won't cut it
People have sent resumes on pizza boxes, made fan accounts, showed up singing
"If you really want something, writing the email and sending the resume once isn't gonna cut it"
Handling Difficult Conversations
When Your Boss Gives You Hell
Don't cry in front of them (hold it together)
Put your ego aside and actually hear what they're saying
Take time to process without getting emotional
Use your "10th grade math teacher voice"—monotone, unemotional
Follow up with what you heard and how you'll address it
The Reframe: "When someone gives you feedback, they're putting their arrows into your quiver." Use that information to become more powerful.
The Culture vs. Performance Balance
At Barstool, talent gets protection to say controversial things because:
They have diverse revenue streams (not just advertising)
They never positioned themselves as "perfect"
They believe people should be able to make mistakes and learn
The Business Lesson: Build multiple revenue streams so you're not beholden to just one constituency.
Salary Negotiations
If asked "What do you want?":
If you have a number: Say it
If you're not prepared: "Let me be thoughtful and come back to you"
If your number feels high: "This is what I'd like to make. I'm obviously willing to be flexible"
Come prepared with:
The specific number you want
Why that's your number
Context about market rates
First Day of Work Survival Guide
What to Expect: First days suck. You're awkward, can't access anything, don't know where to eat lunch.
What to Bring:
Notebook and pen
Pack of gum (bad breath is your enemy)
Comfortable outfit
What NOT to do:
Don't decorate your space on day one
Don't eat anything that gets stuck in your teeth
What TO do:
Write down three things you want to learn/accomplish
Introduce yourself to people
Keep that vision visible so you don't forget your goals
The Path Forward
Your 20s Investment Strategy
Think of your 20s as an apprenticeship. You're not owed success because you have a degree. You earn it by getting in the trenches and learning.
The Compound Effect
Every job teaches you something. Every failure builds resilience. Every difficult conversation makes you stronger.
The Long Game
"The stuff you leave with—you're not going to remember all the conference calls. You're not going to remember all the marketing decks. You're just going to remember the people."
Key Takeaways for Your Career
Location doesn't determine destination - Where you start isn't where you'll end up
Trust your gut - You know when it's time to leave, the hard part is acting
Relationships matter - Build them before you need them
Failure is education - Every mistake teaches you something valuable
Work is apprenticeship - Your 20s are for learning, not entitlement
Volume beats perfection - Consistent effort outweighs sporadic excellence
Feedback is fuel - Use criticism to become stronger, not bitter
Final Thoughts
Erika's advice isn't about playing it safe or following a traditional path. It's about being honest with yourself, working relentlessly, and never being afraid to take the harder road if it leads to growth.
Your career isn't a straight line. It's a series of choices, risks, failures, and recoveries. The people who succeed aren't the ones who never fall—they're the ones who get back up and keep moving forward.
The Bottom Line: Your 20s are for figuring it out, not having it all figured out. Work hard, fail fast, learn constantly, and don't be afraid to bet on yourself.
Want more unfiltered career advice and insights on navigating your 20s? Listen to Guyset - A Guy's Guide to What Should Be Talked About on Apple Podcasts, Spotify, and all major platforms. Join the conversation at josh@guyset.com
Timestamps:
3:13 First jobs
5:41 How to know when to leave a job
7:17 How to have the leaving conversation with a boss
9:37 How Erika made the decision to leave Barstool
13:09 Erika talks Dave Portnoy
14:48 How Erika keeps up with all the Barstool content
17:21 Her recommendations for staying above the noise
19:32 Erika talks about Barstool’s personal brands
22:11 Erika talks about Call Her Daddy and Alex Cooper
23:28 Erika talks about Barstool’s creator protection
25:47 How she deals with advertiser complaints
26:56 Erika talks about Penn
30:13 Erika talks about her favorite time at Barstool
31:52 Erika talks about her upcoming book “Nobody Cares About Your Career”
35:58 When did she find time to write the book
37:21 We’re doing 1 on 1s with Erika
37:43 What should I do if I’m you're getting response to applications or interviews
41:50 How to approach the promotion conversation
45:44 The salary conversation
46:45 Advice for starting a new job
48:04 What to do after a bad conversation with your boss
53:17 Erika talks about what’s next for her
53:51 Will we see the Token CEO podcast again?
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See you next Tuesday!
