How Jomboy Media Renews 90% Of Their Partners

👋 Welcome back to Sponcon Sports, a weekly newsletter dedicated to sponsored content strategy in the sports industry!

This week, Chipotle launched a sweepstakes giving fans a chance to win a Celebrity Card, which grants one free entree, side, and non-alcoholic beverage every day for a year, plus one free catering order for up to 50 people.

While Chipotle has done this before, what stood out this time was the ability to apply via LinkedIn Easy Apply. To enter, simply go to the listing (now inactive), tap Easy Apply, and attach a document with a link to your online submission.

If you have a partner like LinkedIn, Workday, or Indeed, this is a cool and native way to drive leads: entering sweepstakes, applying for grants, nominating community members for prizes, entering to win team experiences or merchandise, and offering exclusive internships or job applications at partners’ companies.

This framework not only engages fans but also drives traffic to your partner's platform. Repeatedly directing users there throughout the year reinforces their presence in fans’ minds when they’re listing or applying for jobs.

In Today’s Edition:

• Jomboy Media’s Partnership Strategy, A Breakdown ⚾️

• Wrexham Has A Sponsored Contract Printer 🖨️

• Man City Brings The Heat With Sure Sport UK 🔥

🏊️ DEEP DIVE
How Jomboy Media Renews 90% Of Their Partners

Jomboy Media has some of the best partner integrations in sponsored content within the sports industry. Here’s a taste of what has been done in the past:

• BlitzBall Battle 3 - Shady Rays, Set Design + Shady Vision Replay

• Captains’ Leagu Ball in Play - SeatGeek, Musical Seats

• BlitzBall Battle 4 - DraftKings, Draft King Ad

These integrations are seamlessly woven into their content but are also fun and creative, earning the appreciation of their fans.

Founded by Jimmy O'Brien, known as Jomboy, and his friend Jake Storiale, Jomboy Media is a creator-led sports and entertainment media platform dedicated to producing relevant content for a highly engaged community.

The duo launched the Talkin’ Yanks Podcast in 2017. Alongside this, Jimmy creates popular baseball breakdown videos where he narrates game footage, offering detailed commentary and lip readings. These videos often highlight unusual, controversial, or humorous aspects of the game.

In November 2019, The Athletic revealed the Houston Astros' system of tipping pitches. O’Brien shared a breakdown video that appeared to demonstrate how the Astros were stealing signs. This video went viral on social media, sparking exponential growth for the company.

As of 2024, Jomboy Media has expanded far beyond baseball content. It now features 26 personalities, 21 brands, 44 shows, and over 100 social media accounts.

The company's partnerships boast impressive statistics:

• Ninety percent of their partners renew.

• One in two fans have made purchases from partners.

• Seventy-five percent of fans have discovered new brands through Jomboy Media.

To uncover the secrets behind their success, I spoke with their COO, Courtney Hirsch.

In our conversation, Courtney delves into her role in monetizing content, building an in-house ad sales team, and the unique approach Jomboy Media takes with its partnerships. She explains how they have maintained a 90% renewal rate with brands like DraftKings and SeatGeek. The key? A perfect blend of fun, authenticity, and deep substance.

Courtney also shared insights into their innovative content strategies, like the Warehouse Games, and their evolving merchandising efforts. She explained how Jomboy Media navigates brand integrations while staying true to their community and delivering best-in-class sponcon.

Courtney's insights offer a fascinating glimpse into the world of Jomboy Media and its continued success.

Note: Questions and answers have been lightly edited for length and clarity.

ALEX: Can you briefly describe your role now and how that differs from when you started as the VP of Sales & Partnerships?

COURTNEY: My background was in advertising sales. I worked mostly in ad tech companies. This is my brother's company. He needed someone to help monetize what they were building and put some infrastructure around it.

That was a big decision, but I decided to come up because I filled his biggest need at the time: monetization from direct advertising partners.

I built the whole infrastructure of the team from the ground up. I did the rate card, was the analyst, prospecting, closed the deals, executed it, and then focused on hiring a team around me and building an in-house direct ad sales team.

Last April, I moved into the COO role. We realized that we needed someone to oversee the entire business. My main job now is to make sure that all the departments are working together.

That's content, sales, finance, e-commerce, events. We're all accountable to each other and I'm the one that integrates everything.

ALEX: How would you describe Jomboy Media's partnership strategy?

COURTNEY: We're trying to stay true to ourselves and true to our community.

When we think about our partnerships, we're always thinking about our community first, and how integrating this partner is going to impact our community. If it's negative, we don't move forward with it.

We're trying to find partnerships that align with our values and tone of voice.

We have a unique voice in the space where, someone said this once, and I loved it, they said “light in tone, deep in substance” because we know what we're talking about, and we work hard and we're thoughtful, but we are fun and all about having a good time.

We're trying to find brands that match that tone of voice and then we're trying to build long-term strategic partners. We've done this successfully from the beginning.

DraftKings has been our partners since 2020. We're going on four years strong now of partnership. SeatGeek, the same thing. We started working with them using their affiliate code at the bottom of our YouTube links and we drove so much revenue for them, they were like, oh, we need to have a legit partnership. Now we do year-long partnerships together.

So that's how we approach it. Building long-term partners, matching our tone of voice, and then we always try to deliver more than they expected and leave our partnerships wanting to come back for more.

ALEX: Jomboy Media has a 90% renewal rate, which is incredibly impressive. What's been the key to that success?

COURTNEY: I think it's the customer service we provide, and that is unique for the creator space. We're really lucky because Jimmy and Jake were creators and built that whole company.

Then they partnered with me early on who knew what it took to build an ad sales team.

A lot of people were just figuring it out, but I knew how to set expectations, how to showcase that we executed something, and how to go above and beyond and deliver more value.

That white glove service was really important to me and that is really impactful in that [creator] space because a lot of companies or creators are still learning how to do brand deals and manage relationships.

ALEX: What did the partnership process look like when you joined the company in 2020?

COURTNEY: When I walked in there were a handful of advertisers and they delivered for them, but what was missing was the communication piece and not knowing how far over-communication can go for relationship management.

ALEX: What is the biggest revenue opportunity right now? Do you have a prediction of where you think things are going?

COURTNEY: The biggest revenue opportunity right now is still direct ad sales and the relationships we're creating with our sponsors. I think where we're seeing revenue eclipse at a faster rate is merchandising and content licensing.

Merchandising is exciting for us because we started just like a t-shirt business. You see a lot of creator businesses do this, print-on-demand. We're making moment-based shirts about things that happen in sports, which is still very much a part of our strategy.

But in the future, we're excited about growing the merchandising around the content verticals where we fully own the IP like Warehouse Games, a creator-led sports league that we invented.

We made up our own sports. We made up our own league. We invented eight different team names. They all have different logos. We have different equipment that we use to play with these sports. So just thinking about where we can go in merchandising for the Warehouse Games, like all apparel, but then sporting equipment, like figurines and posters. The sky's the limit there.

The opportunities that we have in front of us now with content licensing and collaborating with more traditional larger media companies who have more resources. They have more distribution.

That's exciting because as creators, we spend so much time and resources investing in our content and we're always looking for multiple ways to monetize it. If we can create a piece of content, monetize it through AdSense, monetize it through direct ads, and then license that content to someone else, that's a really high-margin business for us because we've already paid to produce it.

ALEX: What is the rationale behind seeking a 360 partner versus someone who focuses on just one aspect of what you do?

COURTNEY: This is a big focus for us because that's how we deliver the most bang for a buck when brands come in and work with us across everything we do. We've been successful at that when we build a relationship at the client level.

All of our integrated 360 partnerships have a strong client-direct relationship. We just launched a couple of weeks ago with BeatBox. They’re a really fun party punch. They got a bunch of different internal teams involved.

They got their influencer team, their podcasting team, their events team, and they all have to come together and decide on Jomboy Media.

It's a little harder to make those happen because you don't only have one stakeholder now, you have three different stakeholders on the client side. But when it does happen, it's so worth it.

Beatbox is a premier sponsor for the Talkin’ Yanks podcast.

They get a custom segment, they get influencer posts with Aaron Boone, who’s on our podcast, and they just sponsored the Talkin’ Yanks at the Shore event that we did with a BeatBox slushy station there, which was really fun.

That's a key part of our strategy because it performs the best. We know what's going to work, but we have to do all the legwork to influence the multiple stakeholders at the company.

ALEX: As you continue to achieve success and build credibility in the sports media space, does it get easier to gain buy-in from brands, or do you still need to provide a certain level of education?

COURTNEY: I think there's still a certain level of education you have to do and it's mostly over how we actually execute the ads because we do post-read, integrated, baked-in ads.

The creator not only gets you to the community that you want to speak to, but they are also delivering your message.

For a lot of brands, that's a little bit nerve-wracking because they're used to handing over a TV commercial, a pre-roll spot, or a display ad, and saying, run this.

You need to build trust to allow them to hand over that control.

ALEX: Jomboy Media often emphasizes that you’re not just making ads; you're creating content. How do you approach making brand integrations feel natural within the content you're already producing?

COURTNEY: This is our favorite thing to do and we excel at this with the Warehouse Games commercials.

We made these 30-second commercials for our brand partners where our creators are in the commercials themselves.

We're constantly thinking about how to make this content not feel like an ad so that listeners and viewers want to tune in for the next one.

We start by creating barriers, actually. That has helped us to be more creative. For example, it has to be 30 seconds long. We need to get SeatGeek’s messaging across. We want this to be sequential in that you want to watch every commercial that we make. So you don't skip over it from game one to game two to game three.

We're going to be delivering something unique each time. We sit in a room and the team is really creative.

I love the one we did for SeatGeek where it was Musical Seats. You were watching a game within the game. Then you wanted to keep on watching to see who was going to win musical seats. There's always a storyline or a through line in the commercial itself and adjacent to the gameplay.

ALEX: Do you think that approach is why one in two people redeem offers from your partners? Or is there anything else that has led to that?

COURTNEY: I think that's a piece of it. It's really that our community is so loyal and they're rooting for us.

When our sponsors go all in for us, our community can tell they’re letting us be ourselves.

Then our community wants to show up for those sponsors. They want to support us and ask us, “what code do I use? I can't find the code. I want to buy Farmer's Dog, but I want to make sure you get credit.”

They believe in us. They know our grassroots start and they want to support us. They know by supporting our brands, they're supporting us.

ALEX: In your L10 meetings, you focus on revenue, community growth, and community engagement. How do you measure success in each of these areas?

COURTNEY: We have goals across all of our lines of revenue and we track week-over-week where we are and if we're on or off track.

We also have profitability goals that go on the top-line financial metrics that we're tracking and then for community growth, we are so granular. We check every single social media account, and YouTube account. We have growth goals for every account so we can see which ones are lagging and which ones are ahead.

We're really trying to focus on the big five for our social media and get those to a million followers or more. Then for engagement metrics, we break out shorts versus long-form videos and look at the YouTube benchmark. We always want to make sure that we're 10% above the benchmark and if the YouTube benchmark’s going up that means we have to go up and step up our game too.

ALEX: How do you communicate with partners about the difference in value between YouTube views (30 seconds or more) versus other social views that are just two to three seconds long? Is there a need for education on this?

COURTNEY: I think advertisers mostly know that. They know that YouTube views have a higher weight to them. A lot of them just want to focus their ad buys on YouTube because they know it's a more dedicated audience.

Since our ads are baked into the content itself, we don't just sell one platform. If you want to sponsor a breakdown, your integrated sponsorship goes out on YouTube, TikTok, Facebook, Instagram.

What we do is we proportionally weight the CPM based on the platform distribution.

So YouTube will have a higher weighted CPM than if it goes on Twitter or Facebook. We value those impressions not as strong or high quality as the YouTube impressions.

Our advertisers appreciate that because we're not counting everything the same.

I think that's refreshing for them. They're like, oh, they're not just trying to sweep for every impression that they can get.

ALEX: When you introduce new inventory, such as Slapball, do you first launch the concept, assess the results, and then pitch it to brands? Or do you aim to sell it immediately once the idea is fully developed before it goes live?

COURTNEY: We focus on building the content, growing an audience, growing engagement, and then we'll take it to advertisers.

Usually, programmatic revenue will be your first form of monetization, and then depending on the growth, it will be direct ad sales.

From there, you could start merchandising it if people are really leaned in. And then, it's content licensing if other platforms find value in it.

We follow that flow. There are small cases where what we want to do lines up with a big tentpole event of theirs or a big initiative, and they will sponsor custom content or this new initiative, but it's mostly the other first one.

ALEX: With so much content across various channels, how crucial is it to plan out your calendar and provide your sales team with a runway to capitalize on these opportunities?

COURTNEY: At first, we were not planned out at all. We were just going video to video and selling it. We had some weekly series like Talkin’ Yanks, where you knew the schedule.

But then a lot of what we did was sporadic and we realized we wanted to step up our sponsorship game. We wanted to get these year-long sponsors that were ingrained in the content and integrated into the sets.

We needed to be more planned out. We started planning out Warehouse Games, for example. We had the whole 2024 season planned by August or September 2023, down to the whole calendar year, everything we were going to post.

But I think what we've realized is what's just as important for this business is the ability to react to moments in sports. You can't be so overplanned that a creator can’t talk about the hottest thing that's going on in sports right now.

They can't react to this play. Or they can't just do a passion project that then motivates them, energizes them, and creates a new audience. We're trying to do a better job of having our planned stuff, but then having the free form, which is going to lift up everything else if the creators are energized and talking about topical things.

ALEX: Last year, you set goals for brand awareness, audience growth, and building out a website. How are you progressing towards those goals? I was surprised to hear brand awareness was a focus—I thought everyone already knew about Jomboy Media.

COURTNEY: That's the cool thing about our community if you know us, you know us and you ride for us, you go to bat for us. And then if you don't know us, you're like, wait, I heard of that. What is that?

It does require a lot of education. Community-wise, we're crushing it. We're crushing our community growth, we have not missed the community engagement goal. Revenue-wise, we're really excited that we just brought on some blue-chip advertisers. We've closed T-Mobile in the past couple weeks, we just closed Captain Morgan.

We are stepping up our game from the sponsorship perspective.

Then the website, some of these bigger projects, they're more challenging to get off the ground than I thought. We're building a video-first website, it’s Netflix-style. We’re excited about it, we're going to launch it soon.

But it's really the first step to something. What we learned is that for so many years, we were just going, doing, creating, posting, posting, posting. We were not organizing, or structuring the content. We didn't have a nice little home for it.

We had to re-download everything from YouTube. It's just a beast of a project that we're working through, but we're still very excited about it.

ALEX: I noticed your LinkedIn account four months ago, and I see you've been investing more time and effort into it. What prompted that decision, and have you noticed any business impact from posting regularly and being more transparent on the platform?

COURTNEY: I was so nervous to do it. I was like, I'm not the creator. I'm not in front of the camera. I'm the business person.

Then I got talking to people and just me realizing myself, that LinkedIn is such a great place to create free awareness for your brand, for your company, and for your personal brand.

It has opened the door for so many connections, like hiring, and partnerships, we've had inbound leads come through advertisers. I've just learned so much from other people that are putting themselves out there and sharing stuff.

I was terrified to do it, but I've been consistent with it for the past year and it's really made an impact. So now I'm trying to encourage everyone else to do it.

ALEX: Do you have any advice for sports organizations looking to build a successful content offering?

COURTNEY: You have to be where the audience is and where the attention is. I think about it as consumers’ attention. How do you get into those conversations? Don't get tied to, I just want to do this format or I just want to focus on this platform.

That's where you get stuck. You have to step back and think, where are people spending their time and then integrate yourself into those platforms and continue to evolve.

💼 CASE STUDY
Sponsored Content of the Week

Thousands of Wrexham AFC fans, including me, spent part of their Saturday staring at a printer.

Why?

The Red Dragons teased a contract signing on their social channels, with the news coming from their HP Smart Tank printer via live streams on YouTube and Instagram.

The live streams began with the HP printer front and center and a 4:20 countdown. When the clock struck zero, a player contract for goalkeeper Arthur Okonkwo was printed. If you couldn’t see his name clearly enough, a picture of Okonkwo was printed after the contract.

Using an HP printer as the star of this content made perfect sense.

According to the club’s press release, “as Wrexham's global technology partner, HP supports club operations - including the exclusive printing of new signing contracts.”

While Wrexham could have used HP to announce any news, it’s fitting here because you need a printer for players to sign their contracts at the facility.

This is similar to the outstanding product-moment fit of the NFL’s Draft Cam in partnership with New Era Cap. The product integration was already part of the action even without the sponsorship.

Because of the strong connection, fans weren’t just okay with it—they celebrated the sponsored content.

Wrexham was thoughtful in how this activation came to life, especially in such a short news window.

Played To Their Global Audience

The teaser graphic included both UK and US time zones for when the live streams would begin. This smart move, given the club’s popularity in the US as a result of their celebrity ownership and the success of FX’s Welcome to Wrexham.

It definitely helped me quickly understand when to look out for the live stream.

Leaned Into Native Features

Wrexham’s channel strategy was tailored to each platform.

They added a reminder to their Instagram in-feed post so fans could be notified when the live stream began.

Plus, they ran the YouTube livestream as a Premiere, building excitement among fans as everyone could see the announcement together in real-time. HP was active in the chat, saying, “Let us know if you need more paper, Wrexham AFC #HPxWxmAFC.”

Set Up Sponcon For Success

Not only was this the first signing of the summer for the Red Dragons, but it was also an important one that fans have been asking for since the end of the season.

Okonkwo first signed for Wrexham on loan from Arsenal on Transfer Deadline Day in September last year. He was crucial to the club's promotion to League One, making 40 appearances in all competitions last season and keeping 16 clean sheets.

With this move, Wrexham locked in the goalkeeper for the foreseeable future, as he agreed to a contract through the end of the 2026-2027 season.

Including HP in a big signing like this increased the odds the sponsored content would perform well. It also created the biggest predictable audience to watch their product in action, showcasing the printer’s speed and clarity of its color printing.

The Results

The HP-sponsored signing content generated over 700K views and 10.3K engagements across channels. The YouTube livestream had a peak audience of 1.5K fans.

It's worth noting that the YouTube livestream was two minutes behind the announcement on X. Despite the spoiler, fans didn’t drop off—they waited to see what would be printed. It’s a good learning for future live stream strategies.

We need to continue identifying opportunities for product-moment fit. They allow for heavier, authentic brand integrations that benefit both your partners and your content team.

🔍 SPONCONSPIRATION
Steal These Ideas

Man City and Sure Sport UK had a clever idea: Khiara Keating, Laura Coombs, and Ruby Mace played a game of Guess The Heat Map. This concept could easily be adapted for other sports using shot charts for basketball or spray charts for baseball. It also works great as a game on Instagram Stories using the question sticker. I can see this engaging fans across various sports and platforms!

Alex Morgan teamed up with Molecule Sleep for an episode of Pillow Talk, a this-or-that style game focused on the San Diego Wave Forward’s sleep routine. This collaboration produced 3.1M views and 82.3K engagements.

In the PGA Tour’s Outside The Ropes series presented by TruGreen, we got an inside look at Jason Day’s home, featuring major-inspired bunkers and an indoor virtual green.

Having Goat Fuel sponsor celebrity attendance at Chicago Sky games is a perfect match!

You're just a great name away from connecting a sponsor to content and reinforcing their brand messaging, like the NBA's Smooth & Buttery Plays presented by Ritz Crackers.

🚨 ICYMI
What To Watch For

Must See Activation: Betting and Beer, what a combination! Thank you to Dawid Prokopowicz for sharing this incredible case study of Cerveza Aguila’s Beer Lottery campaign with the Colombian National Team.

Athlete Partnerships Report: Sport Industry Agency of the Year, Ear to the Ground, dropped a new report about maximizing athlete partnerships with some helpful case studies.

Subway Sand-Rich: Speaking of athlete partnerships, Vox dives into why all the world’s best athletes do Subway commercials.

Brand Brothers Livestream: Jordan Rogers, Oren John, Ashwinn Krishnaswamy, and Bimma Williams discuss hot topics in branding and marketing. The series will continue weekly on Fridays at Noon PT via Jordan’s YouTube channel and Oren’s X account (on Spaces).

Chiefs Love Story: The Kansas City Chiefs are teaming with fellow KC brand, Hallmark, to develop Holiday Touchdown: A Chiefs Love Story, a movie that will be filmed entirely in Kansas City.

Tennis Kids Show: Wimbledon produces a show called Blade and Bounce on YouTube Kids where younger fans can learn about and explore The Championships.