🎓Lessons Learned From Two Years Building A Sports Betting Startup

A new week, a new Probly email! I realized before starting work on this email that we just cruised past Probly’s technical two-year anniversary at the end of April and I never discussed it. So, hey, kudos to us for still existing! To celebrate, let’s get into it in the intro…Here’s some lessons I’ve learned in these two years, about betting and startups in general:

1. The Power of Plus-Money 50/50ish Bets — Let’s start with an easy one that, if you read this email or watch our videos, you know I always point out: There is nothing more +EV in betting than a bet with a probability around 50% that you’re getting plus-money on. The biggest win for sportsbooks — particularly the aggressively pricing ones, like DraftKings — is constantly finding ways to make bets minus money. When you flip a coin-toss bet into plus money for you, you are the sportsbook for that bet. It’s no guarantee you’ll win an individual bet but you’ll give yourself a much better shot to win in the macro. Some of our best days with our content picks have come with a ton of 40-55% probability bets at plus money.

2. Withstanding Low Probability Bets Matters A Lot — We talk about responsible bankroll management a decent amount in Probly’s content. I’ll point out “If you don’t have a big bankroll, don’t take this bet” for things like a Home Run bet with a 10% probability. But your ability to transact longer shot bets — with the bankroll to sustain it — can be huge. Despite a 105-181 record in MLB bets this year, I’m up 25 units because of things like home run bets and longshot derivatives (and that’s with playing some less efficient odds with my bankroll being on DraftKings). Between that and a huge run on NBA underdog moneylines, I really believe these bets should be an important part of your process even if they are less frequently given out across content.

3. There’s A Real Lack Of Innovation Productwise — This one goes hand in hand with the betting part as well as the startup one. There are apps we studied in May 2022 that, no joke, have made zero changes or improvements in two years. They’re happy with the inertia of their signups, App Store rankings, and lack of value-add. You know by now that’s the opposite of how we try to do things. It’s the same for sportsbooks as well. The biggest innovation in this time period? PrizePicks and Underdog selling people on the joy and upside of largely -EV parlays. Those two products push the bleeding edge more (Underdog’s sportsbook is even offering a swipe-style interface like ours or Tinder’s now) but on all your largest marketshare apps, you’d be hard pressed to find a single innovation or deviation from expectation that has occurred in this time period.

4. You Need To Spend As Little As Possible — Onto our more startup-y lessons — and this is a big one. I’ve spent a lot of money getting Probly out and paying its bills to this day. More than an average American’s salary, by a decent clip. While we’ve now got things mostly lean, this includes a ton of money in development, occasional issues with overspending as we worked out our tech, and now our monthly payments for AWS and OddsJam’s data feed. I don’t know how you make a new data product without getting some of the “best of the best” data/tech in the mix — you can’t build something like Probly without some cost — but we could have been more meticulous early on in a way that would have saved me money and increased our burn rate. Finding customers and product success as early as possible with as little spent as possible should be the goal, for any startup.

5. You Can Never Stop Moving — This is broad but, really, the biggest thing in a startup for me this go-round is always staying busy. We juggle developing new products, content creation, marketing material creation, data analysis, updating and optimizing things, fundraising, email outreach, meetings, and all of that. When I’m not doing those things, I research things like how to make us convert better, App Store optimization, or how many price options you should have to increase sales (apparently it’s 1 or more than 2…so we screwed up there), I study competitors, I look at other successful non-betting startups or their decks or App Store graphics or ads. It’s a lot. But ultimately, the job is to keep moving and finding SOMETHING that will add value while prioritizing the urgency with which to do it. The same is true for product development. You can’t afford NOT to stay busy.

6. Ethical Marketing Is A Challenge — This one pains me to admit because I really do want to believe that you can be completely forthright with people and have it work. But, realistically, our approach will never translate as well as people on social media selling “locks”, some of which even make fake screenshots (or, similarly unethically, place a series of parlays in an attempt to generate a “big winner” screenshot at any cost). Then you have people who just provide “the last 10 games” type of data and have no track record of success to point to, yet sell customers on being able to research their way to profitability against the most powerful algorithms with key market data for sportsbooks. We’ve had a lot of investors ask us “What happens if someone makes a better model than Probly’s?” as if that’s the risk point for us. The risk point is not being able to cut through the noise of an industry of inflated success or outright obfuscated failure.

There’s a lot more I could include in here but these are some of the more interesting ones. I imagine there’ll be even more to reflect upon in another two years, hopefully with us having started to achieve all we’ve set out for. We’ve covered a lot here in the 81 emails I’ve put out, starting a few months after our initial Probly creation process began so it’s hard to totally distill everything down (and as you may have read throughout them all, I have feelings about a lot of different things).

Ultimately we’re grateful to still be chasing this dream two years later with now a good amount of you who are happy and seemingly getting great results from the product. Year one was all about the ideation and how to execute it. Year two was about making the product into something viable in the marketplace and starting to sell it. Year three will hopefully be about putting it all together, for the good of us and all of you.

Get 50% off your first month or year now — under $10 for a first month or under $100 for A YEAR — with promo code FIRST. Or get a seven-day free trial on the App Store version!

Today, we’ll take a quick jaunt through the day’s MLB bets, some bonus EMAIL EXCLUSIVE ones for the NBA playoffs, and our latest product and company updates at the end! It’s your Probly Email for May 10th, 2024! - @ChrisSpags

• 🏀 Top NBA Playoffs Bets and MLB Best Bets

• 🔓 Probly Updates: Quick Updates

Another week here and, with a ton of bets in MLB games tonight, these Top 10 (more like 15) bets from today’s video are all still looking good:

I like getting some more NBA action down along with you guys so we’ll keep rolling with our EMAIL EXCLUSIVE bonus NBA playoffs bets. Here’s a few of the top ones for the next few days of games as of me sending this email:

Of course our best bets, probabilities, and PROBLY Scores are always updated all night and day so get more for yourself at Probly.com or on the App Store.

^Here’s our video tutorial on optimal settings. Read our previous post on optimal settings before you dive in to betting with Probly’s data.

We’ll keep this section short since we had the long intro. Product-wise, we’re working through some updates on the backend that have been blocking our ability to ship new builds. I’m hopeful we’ll be clear them soon but it’s been kind of a drag on our usual “ship something weekly” efforts.

Besides that, we’re in a run of followups and new meetings on the investor front. I’ll keep that under my hat for now since, frankly, it bums me out to talk about stuff possibly incoming only to get rug pulled. But we’ve updated our deck pretty aggressively with an AI feedback tool (Fornax, if you’re curious) and we feel like the pitch is getting stronger. The bills continue to bill in the meantime, particularly as we wait for the App Store revenue from our killer April results.

If you guys encounter any issues not covered here or want to provide feedback, you can email me [email protected].

As always, thanks to all of you who read all the way down here. It’s nice to reflect on two years grinding Probly. I wish we had even more success — particularly since it’d really help us close the gap on fundraising — but there are so many startups that never earn a dollar of revenue. For us to have a good amount of paying customers, a lot of free users, a nice amount of people who regularly read this email, and some hope for the future…it’s a better place to be than my anxiety will allow me to give credit to. And a lot of that we owe to you. So thank you.

You know I have to do one more plug because we need it to keep the dream alive: It’s a great time to get your free seven-day trial of Probly+ on the App Store or use promo code FIRST to get 50% off at Probly.com/subscribe (under $100 for a first year or under $10 for a first month). Change your life in betting! I’ll see you guys next week!