Ranking the Sports Betting Apps By UX From Great To Awful

A Deep Dive On All the Engagement and Conversion That Happens Outside the App

Joe Procopio
9 min readApr 4, 2024

I know. This isn’t like me. This isn’t my thing. Rest assured, I’m not going to do a bullshit listicle. I see the title of this post as ironic, a ruse maybe.

The truth is, a once in a lifetime series of events converged for me last month, and they conspired to create a keg of UX lessons that I can pass on to you.

If you know me, you know my strengths are in maximizing how technology hits the user. I have a knack for figuring out how to turn a business model into a technology that becomes a win-win for both company and customer.

For instance, while I never set out to help build the first iteration of GenAI, that’s exactly what happened back in 2010 with Automated Insights, where we were one of the first companies, if not the first, to turn data into useful stories (Yahoo Fantasy Football, NFL.com, Associated Press, etc.).

That has relevance to this story because Automated Insights started in sports, so the algorithms I developed were always looking for “the edge,” which led to some interest in predicting sports outcomes, which led to some interest in sports betting. Only thing is, in 2010, sports betting wasn’t happening. Not here in the US anyway.

That changed, for me, last month, and I got turned loose on the entire sports gambling app ecosystem.

Sorry, DraftKings

In the second week of March, the state in which I reside finally opened up sports betting, just in time for the ACC Basketball Tournament. Turns out, the school that was kind enough to give me a degree happens to be perennial ACC middle-dweller North Carolina State. So there was interest right off the bat.

Then, a number of the betting apps started throwing free money at the long-dormant-gambler citizens of my state. That meant I had a free almost-all-you-can-eat ticket to a playground of apps and sports and math and numbers.

Anyone who follows tech will tell you that the true innovators in the industry are in porn, gambling, and sports, in that order. And while the use cases in porn are obviously limited, sports betting technology is the SFW cutting edge of mobile UX and revenue generation theory.

Now, I’ve dabbled in sports betting. I hit casinos when I can for the poker rooms. A close-by state legalized sports betting last year so I already had an app and a lot of familiarity, but very little experience in real time.

That all changed in the space of a week when the once-in-a-lifetime part congealed, and North Carolina State, the Wolfpack, made a(n) historic run in the ACC Tournament, setting themselves up to enter the NCAA “March Madness: Tournament the following week.

I watched every game. I bet on every game. I bet dozens of different combinations and permutations and parlays and props on every game. By the time the Wolfpack cut down the nets and earned their automatic berth in the NCAA Tournament, I knew exactly what I was doing, and had near unlimited access to do whatever I wanted to try.

So I apologize to DraftKings not because they’re the worst, but because they’re the best. And thanks to my Wolfpack, I took a lot of their money. And I learned a shit-ton about how transactional UX needs to happen outside of the app UI.

The Rules of Engagement

I told you this wasn’t going to be a listicle, it’s barely a ranking. And in an effort to not waste your time, I’ve already given you the goods. DraftKings is #1. Learn from them.

Now, back to my normal beat. This is what you’re going to learn.

There’s a lot of documentation on the internet about UX and UI as it relates to engagement. These are fine for the first phase of standing up an app in a market, but in the real world, in any crowded field of consumer-facing transactional apps, your UX must be focused on these rules of engagement — and awareness and conversion and retention.

  • Awareness — get customers using it, give them a reason to use it, not just the app, but whatever transaction is behind why the app exists.
  • Conversion — Not just creating an account, but executing a meaningful transaction.
  • Engagement — give them reasons to come back and make YOUR app and YOUR transaction a part of their routine.
  • Retention — Turn “want to use” and “nice to have” into “need to use” and “can’t live without.”

The truth is, very little of this can be influenced by the UI of the app itself, and that’s where a lot of app startups fall on their face. They wind up building a perfect and beautiful app that no one knows that they want or need. While bad UI can definitely hurt engagement, most of what is going to encourage engagement happens outside of the pixels and taps of the UI.

That said, I can bucketize the quality of UI across the apps. DraftKings and FanDuel, and I think it’s because they’ve been doing it the longest with the broadest feature set, have the superior UI, with only taste separating the two.

Signup and deposit are instant and forgiving and they hold your hand along the way. Placing and tracking transactions is also simple, and although no one has tracking progress nailed, they both make it clear how you’re doing if you’re paying attention.

Then I’d say ESPNBet (Penn) fell into an above-average bucket, with BetMGM and Caesars in an acceptable bucket, and Bet365, while not painful, was far from enjoyable.

A side note. BetMGM initially forced me to 2FA every time I logged in from either mobile or web, and because sports betting apps log you out within 5–10 minutes, this made live betting nearly impossible and would have meant their UI destroyed their UX. To their credit, I got on with support and, being exactly THAT guy, laid this out for their poor support rep. While they gave me the boilerplate “for your protection” response, the constant 2FA prompts stopped the next day.

Did I make that happen? Meh.

Anyway, with the mechanics of UI out of the way, let’s talk about the top of the funnel.

Awareness: Three is a Crowd, Six is Noise

If you live in a state that has just legalized sports betting, you can not get away from sports betting app commercials. And then you’ll realize that very little separates those commercials beyond the caliber of the celebrity.

But even that really doesn’t matter.

Advertising, ultimately, doesn’t make a huge dent in a hyper-crowded market. The way those commercials repeatedly followed one another was actually kind of comical.

There were seven apps competing for my attention, six that mattered (and I’ll get to that), and four that drilled their commercials into my brain. Three of those — DraftKings, FanDuel, and BetMGM — were constant, but while three is a crowd, the six apps competing for my awareness were more than competitively noisy enough to drown out any boost from advertising. Ultimately, this is one of the most densely crowded markets that I’ve ever seen. So the advertisements just became noise.

That said, BetMGM probably had the best campaign theme with Vince Vaughn and Tom Brady and a populist angle, but again, it didn’t provide a boost to their overall UX. ESPNBet, the fourth most blitzing of the advertisers, along with non-blitzers Caesars and Bet365, could have done more to make me aware of their existence, but they didn’t need it. I found them.

Conversion: Free Money!

If you can figure out a way to make a prospect feel like they’re getting free money for becoming a customer, whether through discounts, gifts or whatever, you will convert them. In this case, the apps actually gave out free money.

New customers in my state got free money from almost every app. Fanatics (7th place), a clothing company that also has a sportsbook attached, made two critical mistakes. For one, they didn’t list their offer anywhere in their own domains, and secondly, their actual offer was convoluted to understand and kind of useless. So much so that they’re the seventh-place app that I never truly considered a contender.

If everyone is giving away free money or discounts or whatever in a market share land grab, and your free money offer actually drives prospects away, that’s a major unforced UX error.

Now, DraftKings did something really clever here. Since they were established in fantasy sports and already had a bunch of customers, they relied on promotions in which anyone in the state could bet up to a max on events which would always happen, like a point being scored in a game, and pay even money. They made that available to all customers, not just new customers.

This did three things. First, it kept current customers in the DraftKings universe regardless of how much money the competition was spending. Second, it turned on customers and prospects to prop bets, the deeper transactional elements of sports betting that drive retention. Third, it made DraftKings seem like they were the most customer-friendly of the apps, by actually giving money to customers, win or lose.

That said, FanDuel had the most useful and easiest-to-access free money offer. ESPNBet probably gave away the most, but gave it in chunks, limiting how much action you actually undertake.

Engagement: Promotions

I’m in with six of seven apps at this point, turning their fake fives and tens into real twenties and fifties.

How do they keep me?

Make me bet.

Look, I’m not much of a gambler. I like skill contests, like poker, where I have some control over the outcome. But I am an entrepreneur, and I love a good risk/reward ratio. Sports betting is half-skill, half-luck. So the promotions the apps use to keep customers engaged will mean a lot more for me.

DraftKings and FanDuel are easily the best at this, offering boosts and bonuses with an impact and a rhythm that makes me want to transact where I wouldn’t otherwise. The boosts are meaningful, the bonuses aren’t terribly hard to earn. It’s a de facto rewards and loyalty program that I don’t have to keep track of because they track it for me.

This is where Caesars falls down. I’m a Caesars loyalty member and they rely way too much on their existing “brick and mortar” empire and loyalty program within their sportsbook. Sports betting is the first gambling experience in which the digital UX far outweighs the physical UX, and Caesars has not caught up.

ESPNBet over-indexes their promotions on their programming and personalities, as you might expect. BetMGM is fixated on in-app experiences like mini-games and a lot of do-this-get-that, which feels to me like a bifurcation and bad choices. Bet365 really doesn’t offer anything outside of some always-running promos which are more like features which are easily forgotten.

Honestly, this took Bet365 (6th place) and BetMGM (5th place) out of the running. And note that it happened outside of the app UI/UX, and included the app that had the best ads.

Did BetMGM spend too much money on Vince Vaughn and Tom Brady and not enough on decent engagement promotions? Meh.

Retention: Selling my Soul?

Obviously, the intent here is to make me into a full-time sports bettor. And while the implications of that are sticky, with gambling being a seriously dangerous addiction, I’ve been enough on the inside of the sportsbooks to know they don’t want their customers heading down the addiction path either. That’s lose-lose.

Thus, retention is a balance. Where does that balance get struck?

This is the other big mistake most apps startups make. The UX and UI that drives retention usually doesn’t happen within the app or even within the company itself through promotion and communication.

For instance, with sports betting, it happens in sports. When the Wolfpack ends their run, I’ll be somewhat back on the sidelines, until the next sportsy thing that grabs my attention. The apps can offer me all kinds of boosts in the meantime, but if I don’t have the sport in front of me in my day-to-day, I’m not going to bet on it.

This is where the genius of DraftKings and FanDuel staking their claim in fantasy sports a decade ago is paying off. Caesars, MGM, and Penn (ESPN) are brick and mortar casinos with digital sportsbooks. ESPN is 100% all about sports, but are very far behind on the transactional aspects of it.

So while DratKings is at the top of the UX list, for retention and promotions alone I would put FanDuel second. I will continue to use Caesars (third) and ESPNBet (fourth) for at least a while, because the in-app experience doesn’t hurt the overall experience.

It’s a lot like Uber and Lyft, or the five fast-food apps I have on my phone (don’t judge). There is no guarantee that all seven betting apps, or five or even three, will become dominant.

I will say this though, when it comes to video streaming services, these days I’m only paying for Netflix, and I’m on the fence about them too. And it has nothing to do with their app UI/UX.

Hey! If you found this post honest, insightful, or actionable, please join my email list at joeprocopio.com, and I’ll send you brief emails whenever I post to Inc., Built In, Medium, or whatever.



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building TeachingStartup.com & GROWERS. Write at Inc.com and BuiltIn.com. More at joeprocopio.com