“Here’s how the whole thing got started: In junior high, I found the one guy in town who would sell cigarettes to a kid.”
That was how Kirby Grines kicked off our pre-interview.
The question had something to do with his earliest memory of being interested in the business of sales. Like any good businessman, Kirby knows how to take the lead in a conversation and capture the attention of his audience. He does so in somewhat unconventional ways — recounting a story about buying tobacco off a delinquent adult, or rapping about streaming bundles in front of hundreds of C-suite and senior-level executives at an industry conference.
In many ways, Kirby is the total package — a naturally cool and charismatic person who knows how to take command of a room and win people over, and also a highly-intelligent thought leader who can help explain the complicated intersection of media, entertainment and technology at a time when everything feels super chaotic.
Kirby is partially responsible for that chaos. A designer by trade, an early point in his career saw him working with Roku to help them develop third-party streaming apps for their platform. We know how that story turned out: Today, Roku is one of the most-dominant players in the global streaming media space, with a commanding lead of connected TV devices in the United States and a growing presence in other countries. Today, most people can watch streaming content on smart screens in their living rooms, backpacks or pockets — or some combination of the three. The industries of traditional broadcast and cable television have been completely upended by connected video services that give consumers more programming, price and platform options.
For the past few years, Kirby has privately helped entertainment and tech companies stand out through his growth agency 43Twenty. More-publicly, he has helped executives, financiers, analysts, researchers and journalists make sense of the fast-paced business of streaming through his Streaming Wars newsletter, a curated digest of news articles that analyzes and contextualizes the problems, solutions and consequences of today’s media and entertainment business. Kirby understands that, to help someone know where things are going, you sometimes have to start at the beginning, and go on a little journey.
A newsletter can only get you so far — which is why, a few weeks ago, Kirby evolved his Streaming Wars newsletter into a full-fledged website that allows him and his contributors to take a deeper dive at the news and trends of the streaming industry. The website is impressive for another reason: For years, Kirby’s work helped build the foundation that lit the spark for the streaming wars, and now he’s assisting the soldiers in battle. If you’re in it, you want Kirby on your squad — he has proven himself capable, time and time again, of cutting through the fog and leading the troops to victory.
The Desk caught up with Kirby earlier this summer to discuss his career in design and technology, what led him to establishing his own growth agency and how that evolved into him becoming a tech publisher — and, also, why he raps at conferences.
This interview has been edited for clarity and flow.
Matthew Keys, The Desk: One of your first sales experiences was selling candy in middle school. What was that all about?
Kirby Grines, 43Twenty: Ah, we’re starting there. I was always interested in doing something with business. As a little kid, I would often have thoughts and wonder what I’d be like, look like as a grown-up. The picture that I often painted of “future me”, was a businessman eating lunch at McDonald’s. Ha. Let’s just say, I Iiked McDonald’s back then.
I always liked the idea of transaction-related commerce. Somebody needs X-Y-Z. And somebody else has X-Y-Z. Those two people decide to transact. There was something so cool about that.
I lived about a mile from my middle school. This was in the mid-1990s. I would either walk, bicycle, or skateboard. And on most days, I’d stop at the gas station for candy, a bag of chips, a cappuccino, or whatever.
Something clicked one day, where I figured, well, anyone can sell anything, right? I figured since I’m at the gas station every morning, where most kids are coming in on the bus, what if I could be the guy who takes snack orders for the kids in school?
So, I just went for it. If you needed anything from the gas station, I was your guy. Thinking about it, I was doing the GrubHub model 30 years ago.
I’ve always felt a connection with people, being able to help them get things. Jumping ahead a bit, it’s 2015 or 2016, at the time I was at Float Left, the TV app development company I co-founded in 2009.
One night, I’m watching “Million Dollar Listing,” and I’m watching these realtors who act as the middle man between a seller and a home buyer, with no attachment to the product, and I’m thinking, that’s so cool.
Even though a sales prospect would be saying “no” to something I built up from scratch (my company, my team, my services), I learned to not take a loss personally. However, as good as I was at actually doing that, I’m always attached. It’s my company after all.
Those realtors in the show? It wasn’t their house. They’re just the one executing the deal between buyer and seller. There’s no attachment. I envied that on some level.
While we’re talking about Float Left, it’s important to call out that when I’d follow up with my clients post app launch to see how everything’s going, I’d often here something along the lines of, “Kirby, the app looks and feels and does the things we asked. However, people aren’t nearly as engaged in our app as we had hoped.”
The struggles were engagement and retention and I’d hear this over and over, whether the client was a start-up streaming service or a household name.
This drove me mad as a UX designer. And while I’ve worn virtually every hat you possibly could in this space, with the exception of filming a movie, UX and visual design is what I’m classically trained in. It’s what I went to college for. The rest is school of hard knocks.
My business partner Tom and I had several conversations over the years about whether we could offer some sort of service to help our clients solve engagement and retention through UX.
Launching client apps across dozens of connected TV and mobile platforms was already a super tough business. So every time, and there were at least three serious conversations about it, the smart thing was to stick in our lane.We couldn’t take more on.
So while Float Left had to stick to developing and launching apps, perhaps another entity could come in post launch, and optimize UX and solve around engagement and retention.
While I was on a sabbatical, I thought perhaps I could start something new. But I really didn’t really want to start another company.
At the same time, companies were approaching me to see what I’m doing and if I could lead their sales and business development teams.
As a salesperson (one of my hats), I realized that whether you’re in sales or not, you’re always selling. All of us are in sales, like it or not. Whether you’re pitching a SaaS product to a prospect, trying to get a raise, or convincing your kids to take a summer vacation in the mountains, we’re all in sales.
So I thought, If I’m going to have to sell, I might as well sell the idea of what I want to do for work, and that’s helping streaming video services solve their engagement and retention problems through user experience. That was the genesis behind 43Twenty.
The Desk: What was the issue, in a general sense, behind their low retention and engagement?
Kirby Grines, 43Twenty: At the time, many legacy media organizations were driven by a mindset where engineering teams assured executives that simply building an app would naturally attract users — a sort of “if you build it, they will come” mentality. However, that approach is more suited to Hollywood scripts than reality.
The truth is, creating an app is just the beginning. Many companies launch apps, but user adoption doesn’t follow automatically. Success hinges on a variety of factors, including strategic promotion, effective marketing, and well-crafted user journeys. There are countless nuances involved in turning an app into a thriving platform.
Yet, for nearly a decade, companies operated under the assumption that the act of building was enough. It’s a perspective that, in hindsight, clearly missed the mark.
The Desk: There also seemed to be the sense that, you could build any app and people would use it. I remember when CBS All Access debuted in 2014. I did one of the first reviews of a streaming TV app, back when “cord-cutting” wasn’t much of a phrase. CBS All Access seemed like an interesting idea at the time, and embraced the direction that things were going. But, it didn’t work particularly well. It didn’t feel like a finished product. Dish launches Sling TV about a year later, and it also feels a little half-baked, mostly on the programming side. But all of these services felt like they were building up to something. And, I’m sure there were moments where the engineers and marketing teams and all the stakeholders got together, went back to the drawing board, and improved upon what they built.
Chronicling the streaming industry over the past decade has been an interesting endeavor for The Desk. You also have a platform where you aggregate news reports and analysis on the business of streaming, called The Streaming Wars. How did that come about?
Kirby Grines, 43Twenty: It was kind of an accident. Or happenstance.
When I launched 43Twenty, our primary focus was on solving engagement issues for streaming apps and services. It became clear that content marketing could play a crucial role in our strategy. During that time, I was meeting with various departments, but it seemed like no one knew exactly where I fit within the organizational structure. However, my insights on user experience, engagement, and retention were resonating, so I decided to start sharing those thoughts externally.
Initially, I intended to write an article every week, and I think that lasted about three weeks. Come week four, I had writer’s block and was heads-down in project work. So for a lack of not thinking of anything original to write, I grabbed a handful of industry news, riffed on each story and packaged it up as an article, and also sent it out as 43Twenty’s first newsletter campaign.
The response was overwhelmingly positive. Although I’m my own toughest critic, always feeling things could be better, the engagement with those posts was strong. That response laid the groundwork for what eventually became The Streaming Wars newsletter.
The Desk: We’re talking just before the StreamTV Show in Denver (Editor’s note: Yep, it took me this long to edit and publish the interview…), and I keep seeing these social media posts teasing about a possible rap at the event? What’s that about? Are you really rapping about connected TV?
Kirby Grines, 43Twenty: Haha! Yes sir. Speaking of business, a little known fact is that my first serious-ish business was a record label I started in high school. Primarily, I did it as a way to distribute my own rap music. But we had a couple of artists signed, and I did some production projects.
Probably the coolest thing to a high-schooler is how all these different magazine publications would send you their magazines for free in hopes you’d advertise in them.
While I dropped the record label to go to college, I kept rapping. Every week, I’d go to rap battles around the city (Columbus, Ohio). Battle rapping was great. If you’re not familiar, it’s like roast comedy, but over music, and the sentences rhyme.
I have a Linkedin version of the Streaming Wars. And one day, I thought I’d try an experiment on my Linkedin post promoting the newsletter. I decided to put a line at the very bottom, something like “P.S., if this post gets 200 likes, the next version of the Streaming Wars, I’ll rap next week’s edition.”
A win-win, I thought. If I get 200 likes, that’s great. I’ll rap. No big deal. And if I don’t get 200 likes, I don’t have to rap.
Fast-forward a bit, and I’m having a conversation at NAB, and I was questioned about the line threatening to rap if I hit 200 likes.
I never got to 200 likes, but feeling fired up and motivated from the show, I decided to say “screw it” and started rapping about streaming industry news every week.
I figured it was a creative way to cover what’s going on in the streaming space — I can just rap about Venu Sports or whatever. I can do it because I have no qualms about putting myself out there, and it’s fun. It’s whatever.
The feedback has been a little inspiring, especially among people who are just putting stuff out — maybe they’re not rapping, but they’re thinking, wow, this guy raps, maybe I should create a content strategy for myself.
The Desk: So, let me take a step back here. You mentioned 43Twenty, which you founded several years ago. But, well before that, you started this company called Float Left, which was one of your early forays into the media and technology space, and it was eventually acquired by iMediaBrands. Can you talk about your experiences there?
Kirby Grines, 43Twenty: iMediaBrands was the company behind the home shopping network ShopHQ, and they wanted to expand their content delivery across streaming platforms. Float Left was selected to play a key role in this strategy by developing the technology and apps that would power their expansion.
When I started Float Left, it was me and my business partner as a side venture. We were actually working at a financial research firm, ahead of its time in the digital space. They offered a subscription newsletter and even produced web videos, which was quite innovative for financial news companies back then.
One day, the CEO of this firm called a meeting with the development and creative teams. In the middle of the conference room was a giant cardboard box, and when the CEO opened it, he pulled out this square device that looked like a cheese grater meets disc player.
It was the first Roku Digital Video Player (DVP) player. He said, “I want to get our video content on here. I brought you all here to figure it out.” The Roku DVP was originally supposed to be Netflix’s proprietary streaming device. But when Netflix decided to be platform agnostic, they spun the device out to Roku.
Long story short, we built some of the first apps for Roku. It was challenging — there was no SDK, not even specifications on thumbnail sizes or graphics. I called Roku probably every day or so asking them questions like “how do we get the content from Brightcove into this channel?” Early days type stuff.
The Desk: I think I had one of those early Roku boxes. It said Netgear on it. I bought it at Best Buy because it was the only way I could get Hulu Plus on my TV without connecting my laptop to it.
Kirby Grines, 43Twenty: So, fun fact, the Netgear model you had was actually the one that came later. The box we were shown at that time was only available through Roku.com or Amazon.
I played a role in facilitating the Netgear deal. Roku wanted to break into brick-and-mortar stores, but they struggled to secure shelf space because Roku wasn’t a well-known brand yet. However, people were familiar with Netgear. By putting the Netgear name on the early Roku box, we were able to get it into Best Buy and a few other stores. The rest is history.
The Desk: Did it seem to you or to Roku that they needed to be in a retail outlet like Best Buy if they really wanted to scale up their business?
Kirby Grines, 43Twenty: Absolutely, that was always the goal. While I don’t have specific stats, getting showroom floor space is invaluable for a device like Roku. The company was focused on getting into retail outlets, and the partnership with Netgear was key to making that happen. Netgear benefited by adding another product to their lineup, and Roku gained much-needed visibility in stores like Best Buy.
I may not have hard data on how successful it was for either company at the time, but considering where Roku is today, getting into retail stores undoubtedly played a significant role in building their brand awareness.
The Desk: And, also, it was $100. I did my research before buying it. Roku wasn’t a name I was familiar with, but they seem established, if not a little new. They had the backing of Netgear and Netflix and Hulu Plus, and at the end of the day, I figured, well, if this doesn’t work, I’m only out $100.
There were a few other companies in the space as well — Boxee, which was acquired by Samsung, and Apple started building out their Apple TV device to support many of the same apps. But Roku seemed to be a differentiator early on. Certainly, putting Hulu Plus on Roku devices was what sold it for me. Their willingness to work with third-party developers was probably a selling point for many, too. Roku definitely came out on top of the streaming hardware wars of the 2010s.
That war eventually transformed into one involving the apps themselves. For several years, the war was fought against one another — Netflix, Prime Video, Hulu, HBO Max, all battling it out for share and scale. Now, we’re seeing a new front open, one where alliances are being built through bundles. We’re also starting to see these companies straining to juggle their emerging direct-to-consumer businesses while maintaining and nurturing their legacy businesses like TV networks and theme parks.
The early part of the streaming war seemed to be, how quickly can we scale, and let’s compete on that — now, it seems to be, how can we survive?
Kirby Grines, 43Twenty: Right. At first, 43Twenty was working with media companies to leverage great UX to help grow subscribers and reduce churn. But as I got deeper into leveraging content marketing to promote my UX business, the market began to notice what I was doing with my personal and professional brand, especially after the Float Left sale. Companies were approaching me for help with their content and search engine marketing strategies. This demand grew to the point where I brought a few of my key team members from Float Left into 43Twenty and we built up a content marketing line of business, also offering search engine optimization, and paid media.
Over time, I decided to phase out the UX offering and focus entirely on the marketing side of things. Niching down allowed us to have a clear narrative on what we do, and it also made sense from a growth perspective — the marketing business scales, whereas the UX business did not.
The Desk: Backtracking a little bit, where did the name 43Twenty come from?
Kirby Grines, 43Twenty: The two things I hate the most about starting a business are logos and coming up with a name. 43Twenty is the result of many, many hours spent trying to find the right name for what I was building — a UX consultancy combined with a recommendation engine. Yes, there was even a recommendations engine, which is a story for another day.
I started thinking about display resolutions, and naturally, I considered 16:9, but the domain wasn’t available. When that option was off the table, I began exploring other display resolutions.
I realized that 8K video wasn’t going to become mainstream anytime soon, so I Googled the resolution for 8K. While I can’t recall the horizontal resolution, I found that the vertical resolution is 4,320 pixels. That’s where the name came from—it’s the vertical resolution of 8K video.
It might seem like an arbitrary choice, but there’s actually some significance to it. When I look at any streaming service across different platforms, I think of evaluating it from the bottom to the top — vertically — identifying areas where they need help, like engagement and customer retention.
Also, I don’t think 8K is likely to go away anytime soon, so it’s kind of future-proof. But, to be totally honest, 43Twenty — it was a name that wasn’t taken.
The Desk: I think it fits nicely — 8K resolution, it’s an improvement over the former standard, right? Everything is a bit sharper, it’s a bit clearer. And what you’re doing is, you’re going to these companies, and you’re helping them make sense of a really complicated industry. You’re making things more clear, making them more apparent, and helping them figure out what they should be doing.
Kirby Grines, 43Twenty: Right. Let me explain how I see the “Streaming Wars.” Initially, my newsletter was called The 20, focusing on about 20 items per edition. But as I began making media appearances on CNBC, SiriusXM, and others, I was frequently asked to comment on the “streaming wars.” So, the newsletter naturally took on that name. However, there’s some debate about branding it as a “war” because many don’t believe there will be just one winner. Some even argue that Netflix has already won, considering they have the most subscribers, which isn’t entirely wrong since a war often implies a race to the top.
But I view the “Streaming Wars” as a broader conversation about how these businesses can differentiate themselves and succeed on their own terms. There are many factors in play. Take the app store tax, for instance — will streaming services unite to avoid paying Apple or Google fees to be in their app stores? Or consider a service like HBO Max could launch without initially being on Roku or Amazon Fire TV, the two largest streaming platforms in North America? Or how and why Disney is teaming up with Fox and TNT for Venu Sports. These are the behind-the-scenes business decisions that aren’t always public but significantly influence a company’s strategy.
That’s what the Streaming Wars are about — these ongoing, often unseen, business decisions and tests that shape the industry.
To touch on what you mentioned about legacy companies and their streaming efforts, take HBO, for example. Yes, they have a streaming service, but they’re still in the content business at their core. Streaming and direct-to-consumer models are entirely different beasts. Previously, a company would create content, and another entity would handle the marketing. But when HBO launched their streaming service, they transformed from a content distributor to a consumer product. I doubt anyone at HBO previously had to think about acquiring customers in the way they do now. Today, you can purchase HBO through more than a dozen platforms — Roku, among others.
Two things that fired me up, when I got into the entertainment and media space in 2009, was the user choice — the convenience of being able to watch whatever you want. It was unbelievable. I can get Max more than a dozen ways today. That’s crazy. But the second thing was the business of direct-to-consumer — the idea that a company like Disney can cut out the middleman and have a direct relationship with consumers.
However, while companies might not want to relinquish their traditional relationships with Comcast, Charter, or other TV providers, they’re now dealing with new middlemen — Amazon, Samsung, Vizio, Roku, and others. That’s not inherently bad, but not every company is suited for a direct-to-consumer model. Some companies would be better off focusing on what works best for them and their products, rather than jumping into DTC just because it’s the trend. They need to ask themselves: What do we have, and how are we helping the consumer in this space?
My biggest frustration as a consultant was seeing companies make decisions that didn’t truly benefit the consumer or even their own long-term interests. Often, these moves seemed designed to appease Wall Street rather than to create sustainable growth. Decisions made based on market expectations often don’t pan out, and that disconnect is still a challenge today.
The Desk: Do you think some executives just fundamentally don’t understand the nuances of direct to consumer streaming?
Kirby Grines, 43Twenty: Absolutely — 100 percent. I get calls from executives who don’t understand the business they’re in. They just want to talk things through with me and my team because they’re clueless about how the space works. It’s mind-boggling. If you don’t understand the business, how are you even in it?
The Desk: You are branching out your Streaming Wars newsletter into a website that is launching this month. Can you tell me more about that?
Kirby Grines, 43Twenty: I was getting great feedback on the newsletter and realized it was an effective content marketing vehicle, but in its current form, it’s primarily a digest of content that exists elsewhere.
The website serves as a centralized information hub for media and entertainment executives. It features a mix of curated content, original articles, and in-depth analysis, with plans to include podcasts, directories for vendor services, and more. The site is a look into the tool I built in 2009, refined with AI and machine learning to filter content by themes and topics critical to business strategy, product development, and marketing.
The Desk: So, the idea behind the website is that it will offer a space, not just for you to expand on what’s already happening in the newsletter, but also to dive a bit deeper into certain topics — you’re able to do that a bit easier with a website than you are in a newsletter. You can go longer on a website. And it will give you an opportunity to connect with your audience and with thought leaders who are making things happen.
Kirby Grines, 43Twenty: It’s an evolution of the newsletter, yeah. The newsletter isn’t going anywhere, but the website will allow us to do more than the newsletter can right now. The format will remain consistent, but I’m not interested in writing 3,000-word newsletters or spending eight hours on a weekly recap. The website is perfect for diving deeper into think pieces and exploring topics in more detail.
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