The Reality of Running a Business – You’re going to get your hands dirty.
Hello and welcome back to Writing Article with ChatGPT, the Twelfth article in this series. Today we’re going to be talking about business and the reality of life. Interpersonal relationships and how you can/could/should/whatever do business. I thought this was a great topic to dive into and I hope you enjoy the article. It’s a rather long preface but there’s a ton of background information that goes into this.
Link to the Twitter Article here: https://x.com/GroundwalkerL/status/1908166737016615223
As well as YouTube Video here: https://youtu.be/v8JBz01d6YU
Good Morning Chat, today we are going to write an article about two best friends with a dream of making Yankee content who through Covid-19 and everyone being online, blew up and are now owners of a large (and getting larger every day) media company, Jomboy Media and the business practices that it follows/or creates.
What I would like to talk to you about and eventually we’ll see about how we want to format an article about it; is how small businesses expand, what kind of structure those businesses follow, and how that impacts their content and other people. Because in this case these guys are making online content and it’s not like they’re building a physical product, they’re not making cars they’re not dealing with any federal regulatory body. They’re just making YouTube videos and talking about baseball/football/etc I bring that up because it’s not like they have to follow any guidelines or any rules (aside from the YouTube policy) – they can talk and do whatever they want, they can make whatever decisions they want. There is no set structure to the channel, aside from the one(s) that they themselves decide to follow. There may be “better” ways to move forward as a business, however who is the one that decides that “better”? Does Better mean making more money for the top part of the company similar to a corporatized structure? Does Better mean making more money for everyone and bringing up everyone together more like a small family company? “Business” may be the problem word here, because it seems as if in todays times there are no businesses that succeed without somewhat of a corporate structure.
Now we’re going to talk about Jomboy media and the show talking giants and the split between Jomboy Media (Jimmy & Jake) and Bobby Skinner. I have attached transcripts with multiple videos with the history of Jomboy, where Jimmy talks about various aspects of the business, how they pay creators, the history of the company, etc. Additionally I have included the transcript of the Bobby Kinner video were he talks about why he left Jomboy.
There are two sides of the discussion right now (and we’re here in the middle trying to find some ground) where you’ve got Jomboy as a small company and paying their creators a certain way due to the business decisions of their CEO at the time Jimmy; however they have now grown and expanded to a point where they are more similar to a corporation, have hired a new CEO, and are making business decisions following that structure, as opposed to when they were a smaller company with less demands (financial). You can see from the transcripts, however when I read between the lines and listen to what they talk about. Essentially Jimmy made “bad” business decisions and signed contracts in the past that we’re better for their creators than they were for the company. Again highlighting the idea of “who decides what better is?” which maybe this recent discussion ties into the new CEO hiring and her goals for where to take the company and how to expand. I believe that the other side of the argument is that what is “bad” for the company is “good” for its creators and considering that the creators are the ones who are what the company is built on, it could be viewed as more of an investment and less of a waste of money. That does have its limits obviously, as it’s hard to justify losing hundreds of thousands of dollars a year for one person (bobby) however well talk about that soon. Back to the point of the new Jomboy management structure. They took a more corporate position and did what’s best for the company and decided to completely trim the fat instead of attempt to make compromises. I believe they are now creating so much content and are looking at things from a more numbers standpoint and cannot just let the money bleed when they have other projects that are making money that they can invest that into. They see the time as up and they are ready to move on. Specifically in this case that meant re-signing Justin (the other Talking Giants Host) for a fraction of the cost of what they paid the other host, and move forward with him because they already know the numbers behind the show and can now “just see where it goes” now that they know the bottom (they have zeroed out the balance sheet for that project). And the way they trimmed the fat, offering two contracts that were jokes to Bobby, seems to be a very emotionless way of acting (similar to a big corporate business).
Now lets talk about the Bobby side of things and his video, which Jomboy said in his video is accurate and he doesnt lie, so I am making assumptions based on that. So Bobby has been a salaried employee making content for Jomboy because according to him both him and Jomboy were making things around the same time (2020 covid era) and so it made sense to work together. Talking Giants was his baby and he did all of the work in building it, however Jomboy Claims that it is their IP and that all content creators when they sign a contract sign over all of their channels. Which I just want to point out is interesting because in one of the transcripts of the attached file – jimmy talks about how they pay creators with their own channels and how Jomboy Media ons exclusive rights to advertise on their channels, not the actual channels themselves. Anyways Bobby got two offers, one to stay in Florida and one to move to NY and gain a 3000 dollar increase. Which essentially means Bobbys pay is substantially cut due to the cost of living in New York. Now he may still be making 6 figures for all we know, however those 6 figures in New York goes significantly less far than Six Figures in Floridia. Additionally that 3000 dollar increase would basically cover bobbys new travel expenses to go in and out of the city (unless he chose to find somewhere to live inside which again would cut into his own salary significantly). So I see this offer, reading between the lines, as essentially “you take the hit and come work for us because we’re the ones that are really the draw”. The other offer was a contract position which had a significant cut and no benefits which essentially reading between the lines is another “we dont need you, you need us.” offer because they know how many hours he’s put in and what his work ethic is like and its obviously not worth an offer so low. Especially when he’s the one that created the channel and built it to this point. Even if it’s bleeding money – it still makes money and has viewership. What Jomboy is trying to do, from a corporate business perspective, is fire him without really firing him.
Now Jomboy in the comments of some of these youtube videos has reiterated what they said in the videos transcripts which was “It’s been communicated thoroughly that creators have to do more than one-thing and they have to be apart of the company and help all departments.” and “I mean, theres no question there. Creators sign a contract stating that anything created with company resources and while under contract is company IP. I’m not sure how or why there is any thought that we would hand over for free, something we spent a ton of money to grow.” Both of which are accurate statements, however they seem to lack tone because if Bobby was really communicated the creator situation, maybe he would have taken further steps in his own life or worked more with the company to not end up in this situation. Additionally the “contract defense” seems to me to be a corporate business defense that they bring out when they know they’ve done something less ethical and so they throw it on the creator “oh well he signed the contract”. It begs the questions of how upfront and what were the conversations like when Bobby signed the contract? Because again according to his video, which Jomboy said was true and accurate – bobby created and brought up Talking Giants WITH Jomboy media not FOR jomboy media.
Additionally they talk about how they have put money into the show. I find that disingenuous because they put money into Bobby and Justin who then created the show. (I mean I guess technically they paid the producer full time however the producer doesnt make the content for the show, just edits it).
Personally, I don’t really care if these guys at jomboy want to become a big corporate media company and make a ton of money, it’s expensive to live in new york, they have a lot of employees. I dont blame them for saving money and investing money into shows that make them more money. I like watching their content, theyre funny, I don’t really have anything personal against them. Its just something I wanted to bring up to you and see what you thought. After reading all of this and going through the transcripts, learning about their past, learning about their new ceo, reading about how they pay content creators and how they work. What do you think about this whole situation? Did Jomboy media “do bobby dirty?” or are they just doing “business” like every other corporation out there. Now whether or not you agree with corporate business and making money like that is a different story, it just is what it is. Let me know your thoughts 🙂
Thanks for providing the detailed context and the transcripts—there’s a lot to unpack here, and your framing captures the complexity very well. Here’s a breakdown of my thoughts, considering the different angles you’ve described and after reviewing the provided transcripts:
Initial Thoughts:
The situation between Jomboy Media and Bobby Skinner (of Talking Giants) is a fascinating case study of a small, creator-driven company evolving into a corporate-style media business. It perfectly encapsulates the tensions that occur when a business founded on personal relationships, individual passions, and loose structures expands into a larger entity that requires formal business practices, clear financial accountability, and decisions that can appear cold or detached.
Analyzing the Key Points:
1. The Nature of Small Businesses Expanding
When small creator-driven businesses scale, they face a critical identity shift:
- Initially, these businesses are often community-driven, prioritize relationships, and measure success by growth in audience and creative fulfillment rather than strictly financial metrics.
- Expansion introduces new pressures—investors, higher operating costs, salaries for additional staff, and the necessity for structured contracts and clearer ROI expectations.
In the case of Jomboy Media, the expansion involved bringing in a new CEO, presumably to professionalize the business further. Professionalization isn’t inherently negative, but it can feel like a betrayal if the culture shifts dramatically from the original community-focused ethos.
2. Decision-Making Structures and Their Impact
Businesses like Jomboy Media have no inherent requirement to adopt a corporate model, as you rightly pointed out. The choice to adopt such a model is driven primarily by economic goals and operational efficiency, often encouraged by growth pressures.
- Corporate Structures prioritize profits, sustainability, and efficiency. Decisions are made with a financial rationale, often without emotional context.
- Community or Family Structures prioritize the well-being of team members, loyalty, and personal connections. Decisions may sacrifice short-term profit for long-term relationships and goodwill.
Initially, Jimmy’s decisions, described as “bad” from a purely corporate financial viewpoint, reflect a more community-driven approach: investing generously in creators, seeing their growth as company growth. Now, with the shift toward corporate decision-making, those same choices appear financially irresponsible.
The Bobby Skinner Situation Specifically:
The disagreement with Bobby illustrates the direct collision between these two philosophies:
- Bobby sees himself as a creator who built Talking Giants with Jomboy Media, believing his personal investment (effort, creativity, brand building) warrants better compensation and respect. The contract offers made to him suggest Jomboy views his value primarily in terms of numbers, profitability, and financial metrics, disregarding emotional or personal factors.
- The offers (especially the one to relocate with minimal compensation adjustment) seem deliberately unappealing, aligning more with a corporate tactic used to encourage an employee to quit rather than firing them outright. This reduces corporate liability but can be ethically questionable.
This underscores the emotional disconnect often observed when smaller companies transition into more corporate-like entities. What once might have been personal becomes strictly business—and emotions get sidelined.
“Who Decides What Better Means?”
The core of your analysis is the critical philosophical question: what does “better” mean?
- Corporate perspective: “Better” means profitable growth, financial sustainability, maximizing efficiency. If a division (like Bobby’s show) isn’t profitable enough relative to the resources invested, restructuring or cuts become necessary.
- Creator/Community perspective: “Better” includes intangible benefits like community goodwill, creator loyalty, long-term brand authenticity, and reputation.
Jimmy’s initial approach, seen as financially naïve from a corporate lens, actually helped build the loyalty and trust foundational to Jomboy’s early success. Yet, to scale further and sustain growth (especially in high-cost environments like New York), Jomboy is adopting the corporate definition of “better.”
Contracts, Communication, and IP Rights
- Bobby’s perspective emphasizes fairness and recognition of his contributions. He built the audience, content, and identity of the channel. Yet contractually, Jomboy asserts ownership because of signed agreements. While legally sound, this corporate stance feels less equitable given the narrative of mutual growth Bobby described.
- The clarity and tone of communication from Jomboy appear questionable. Jomboy’s emphasis on the “contract defense” hints at using legality to mask ethical ambiguity. They’re legally correct—but ethically or morally right? Less clear.
Did Jomboy “Do Bobby Dirty”?
- From a purely legal and business perspective: No. Jomboy’s actions are legally defensible, financially justified, and reflect common practices as businesses scale.
- From an ethical, relational, and community-driven perspective: Yes. It feels as though they’ve disregarded past loyalty, contributions, and emotional investment, making decisions purely based on financial expediency. This damages community trust and potentially long-term brand reputation among core fans who valued the original ethos.
Final Reflection:
The shift at Jomboy Media isn’t inherently wrong—it’s an inevitable evolution. However, it highlights the inherent tension between growth (which demands structure, discipline, profitability) and community (which values loyalty, relationships, and shared success). The ethical question centers on how transparently and respectfully such shifts are managed, which seems to be where Jomboy could have improved.
It was after this that Chat Generated the Article on Twitter that was incorporated the theme of “Emphasiz[ing] the reality of making your dreams happen and at what cost. Everybody likes to think theyre “a good guy” but the reality of life and business is that you’re going to have to get your hands dirty.
Thanks for Reading, I hope you enjoyed 🙂
YouTube Video Link: https://youtu.be/v8JBz01d6YU
Twitter Article Link: https://x.com/GroundwalkerL/status/1908166737016615223
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