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Lessons Learned From Management Conversations Involving Jimmy Pitaro and Dave Portnoy

Portnoy takes a very different approach to running Barstool than Pitaro does at ESPN. Both work because their companies employ people who understand the culture, fit, approach, and vision.

Jimmy Pitaro spoke last week with Don Yeager on the Corporate Competitor Podcast. The timing of the episode couldn’t have been better for yours truly. I learned a lot. Managing a company as I do, I juggle a lot of things. I have consulting projects to manage, advertising pitches to participate in, conferences to build, and content to oversee and promote daily through our website, newsletters, and social media platforms. There are never enough hours in a day to get things done, but somehow we manage.

For all of those things to run smoothly, a strong team is necessary. But that team has to understand how the company operates, and what’s required to create success. One person or department not doing their part or producing sloppy work hurts the brand and all involved. That then impacts performance and credibility, and potentially, business.

Whether it’s my current operation or my teams during my programming days, I always picture a crew working together to build a car. Everyone has a role to play in getting that car into the showroom, and eventually on to the road. Without the breaks or muffler, the car won’t run right. That leads to a loss of consumer confidence, the brand’s reputation damaged, and business lost.

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Pitaro used an even better example, referring it to the huddle in sports. Plays can’t be executed, scores can’t be made, and games can’t be won if the players involved don’t execute their assignments. It’s what separates winning teams from losing teams. You may want your number called, but when you line up, you’re expected to execute the play whether it benefits you or a teammate.

Jimmy says his meetings with ESPN’s management team are the closest he’s gotten since school to a huddle. He brings his team together to discuss plans, ideas, and important decisions, and they’re invited to debate before calls are made. Once a decision is set, alignment and execution are expected. He refers to their process as ‘Discuss, Debate, Decide, Align’. He also wants well rounded executives not programming leaders, sales managers, and digital bosses. I loved hearing that. Too many outlets employ specialists, not executives with a full grasp of the company’s business.

Assuming a team buys into the vision and process, the other part of organizational success is culture and fit. Different talents and personalities exist everywhere. Some fit, and some don’t. If Dave Portnoy was employed at ESPN it’d be a bad marriage. The same would be true if Mike Greenberg worked for Barstool Sports. Knowing who and what you stand for, how a company or brand operates, and how two sides blend is essential to future success and sustainability. If the pairing isn’t right, regardless of talent and intentions, things won’t work.

After absorbing Pitaro’s leadership lessons, I watched a podcast featuring Dave Portnoy, Kirk Minihane, and Ryan Whitney. Portnoy takes a very different approach to running Barstool than Pitaro does at ESPN. Both approaches work because their companies employ people who understand the culture, fit, approach, and vision.

On this particular podcast, Portnoy shared that he fired Minihane for less than five minutes recently before cooler heads prevailed. Kirk and Ryan took Dave to task for making a rushed decision, and Portnoy explained what set him off. Some passionate exchanges followed, and ultimately, everyone landed in a good place.

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Some in the corporate world might find it odd to hear two hosts/employees spar with their boss on a podcast, but that’s what makes Barstool unique. Dave has built a brand that’s known for candor, passion, and brutal honesty. Because open communication is provided consistently, the audience feels included in the process, and employees know that everything they say is potential content.

Barstool talent have many passionate exchanges, with and without the boss. There’s an us against the world mentality permeating throughout the brand, which is a reflection of Portnoy’s grind, hustle, and conquer approach. Because the staff understands Dave’s vision, it isn’t a surprise when details come out that Portnoy canned Kirk, and then changed his mind. It’s just another day at the office.

As a leader, your track record on decision making is never going to be perfect. You’ll hire people who make an impact, and make you look smart. Others will come on board who don’t mesh with the team, and require having to change direction. Sometimes you’ll find a great fit, but they make a mistake, leaving you no choice but to move on. The sooner you accept being uncomfortable, and understand that your best intentions may still result in things not working out how you hoped, the easier it gets.

I believe that a leader must have good character and can’t waver on his or her vision. If you don’t stand for something, and have evidence to support a way forward, why would you expect anyone to follow you? Many companies have different expectations and approaches, but speaking for the ones I’ve run, I always sought people who are passionate about their work, respect and trust others, understand and buy into the brand’s mission, consistently perform, and give maximum effort. Expecting to win also matters. If those things don’t exist, results suffer, my blood pressure rises, and internal frustration and dissension follows.

Nobody likes to make moves and have them not work out. But the reality is that sometimes things just don’t click. It isn’t ideal, but if you’ve built a good team, have ongoing discussions with them, deliver a quality product, and possess a good reputation, the business will be fine the next day, even as you begin your process to find the next right fit.

Help Wanted

We’re trying to strengthen our coverage of the industry every day, but to do that we need people with a passion to write, relationships, experience in TV, radio, digital, sales/advertising, and familiarity and interest in our brand. With the holidays approaching, interviews will slow down, but I am planning in January-February to add a Music Writer/Editor, Social Media Assistant, and possibly a sports reporter or site editor. Much of that will depend on what we think gives us the best chance possible to grow our company.

If you know the media business, enjoy our work and telling stories about brands and individuals in the industry, have strong writing and/or creative video/graphics skills, and think you can help us, send your resume and writing samples to Jason@BarrettMedia.com.

Thank You, WWE

I don’t share many personal things in my columns but I’m making an exception this week. I got a phone call Saturday night from my son, Dylan Barrett, who reminded me of how awesome this business can be. Dylan spent the evening shadowing the WWE digital team for Saturday Night’s Main Event at Nassau Coliseum. He learned a ton, and was inspired, excited, and determined to work even harder on his craft after watching WWE’s social team create, edit, and turn around content in timely fashion.

WWE’s digital execution across all platforms generates millions of views and engagements. It’s why they’re among the very best in sports social. My thanks to WWE VP of Digital Steve Braband for allowing Dylan an opportunity to learn.

Dylan Barrett with WWE VP of Digital Steve Braband

By the way, Saturday Night’s Main Event on NBC was excellent. Attention to detail is everything, and WWE’s retro show hit all the right notes. From the promos leading up to the event to the show open, old logo, 80’s music playing in between matches, referees dressed in older attire, Joe Tessitore paying tribute to ‘Mean’ Gene Okerlund with a red bow tie, Cody Rhodes repping the old title, and Jesse Ventura adding commentary for the main event, it was well done. Pat McAfee returning to the broadcast table alongside Michael Cole was another cool surprise.

Brandon Thurston tweeted that 26.6 million people watched the 1988 show featuring Hulk Hogan and Andre The Giant. That was a very different time for television, and the ratings for this past Saturday’s show won’t likely reach that level, but if you look at total reach across TV and social media, I’d bet WWE passes that number.

Quick Hits

  • Congrats to Jim Rome. A big announcement regarding Rome’s show will be made today after 12pm ET. It’s a good move for Jim and all involved in the success of his program. Between the move to X and this next announcement, Jim is showing he’s hungry to add to an already established and successful brand.
  • Kevin ‘KFC’ Clancy is hosting a live stream with Opus AI today at 2pm today to demonstrate how AI can revolutionize content creation and distribution. Those interested in checking out the live stream can click here to register.
  • If you haven’t watched Dan Orlovsky dissect NFL action using Next Gen Stats’ Status Pro Visualizer, watch this. His breakdowns have become some of the best content on television.
  • I’ve really enjoyed Drumeo‘s music video series where drummers are brought in to play songs from other bands that they’ve never heard before. It’s a cool concept that shows how talented musicians think and approach unfamiliar content. I can see a fun spin off of it on sports radio or television. Decision makers, put your thinking caps on.
  • If the reports are accurate, I’m glad to see Amazon Prime Video bringing back Al Michaels next season. Al and Kirk Herbstreit have worked well together, and though I know its fashionable on Thursday night’s to bitch and moan about Al’s play calling, I still think he’s performing at a very high level. It’s good to see that Amazon agrees.
  • Netflix is focused on making a strong first impression on the NFL. 22 broadcasters from 6 networks will be part of the company’s two Christmas games between the Chiefs-Steelers and Ravens-Texans. They’ve lined up some of the best football analysts, reporters, and talkers in the business. Now let’s just hope the actual streaming of the game is better than the Jake Paul-Mike Tyson fight.
  • The Michael Kay Show signed off Friday after 22-years on ESPN New York. The crew told tons of great stories during their last show but one in particular stood out. Michael and Don shared how Michael was nearly arrested while broadcasting live at Shea Stadium. WFAN complained to the Wilpon’s about Kay being on the air at the stadium despite not being contractually allowed to. ESPN New York former PD Mike Thompson dared the police to take action, and once he saw that they might, he got Kay out of there and had Don LaGreca do the rest of the show solo back at the studio. Sports radio drama never disappoints. Neither did Michael, Don, and Peter.
  • The Stephen A. Smith vs. Shaq three point shooting contest was comedy gold. Kenny Smith deserves praise for delivering the line of the event ‘I’ll give 10K to your charity if you hit rim”. If you didn’t see it, click here.
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Jason Barrett
Jason Barretthttps://barrettmedia.com
Jason Barrett is the President and Founder of Barrett Media since the company was created in September 2015. Prior to its arrival, JB served as a sports radio programmer, launching brands such as 95.7 The Game in San Francisco, and 101 ESPN in St. Louis. He also spent time programming SportsTalk 950 in Philadelphia, 590 The Fan KFNS in St. Louis, and ESPN 1340/1390 in Poughkeepsie, NY. Jason also worked on-air and behind the scenes in local radio at 101.5 WPDH, WTBQ 1110AM, and WPYX 106.5. He also spent two years on the national stage, producing radio shows for ESPN Radio in Bristol, CT. Among them included the Dan Patrick Show, and GameNight. You can find JB on Twitter @SportsRadioPD. He's also reachable by email at Jason@BarrettMedia.com.

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