Happy Monday.

Most side hustles start on the weekend…but I’m a gambler.
My weekends are work. My Mondays are for doing figures. Which brings us to today’s topic: Sports betting as a service (SBaaS?!)

I’m @ArtParmann, and this is Rounders to Founders. Where I look at different businesses and money making ideas that interest me. Hopefully they interest you too.

So grab your coffee ☕️, load up your spreadsheet. And text your bookie that you’re sending USDT this week. Let’s get to it.

An NFL Hedge Fund?

Can you really be a professional sports bettor? Of course you can.

If an edge can be had, there are a million people out there pressing it as hard as possible. But whether it’s poker, blackjack, hustling slots, or betting sports…it takes discipline. And that’s why most of us lose betting sports.

In 2014 I was grinding $5/$10 No Limit at the Bellagio 5 days a week. And if you’ve played $5/$10NL at a casino in Vegas, you know it’s like watching paint dry. But when it’s NFL season and the games come on, at least there’s something to watch.

So between paint drying sessions I was spending a lot of time learning about the wild world of sports betting. I had just learned what a Wong Teaser was. And if I recall correctly they did very well that year. There were a few places in town to get the right odds (shout out to Jerry’s Nugget. Where walking in with $500 to bet on something feels like the riskiest thing you’ll do that week).

And I can’t remember if it was 2015 or 2016 but one week in December me and a buddy put in an 8-team teaser where every leg qualified*. One of the legs pushed which moved it to a 10 to 1 payout. I risked $2k on it. So a nice little $20k bonus check when I was playing $5/$10 was a solid boost to the bankroll.

* - Qualifying for a Wong teaser just means the line crosses the 3 and the 7. So if you’ve got Dallas -7.5 and Detroit +2.5 on the board that would be a Wong as you add 6 points to each leg and end up with a parlay ticket of Dallas -2.5 and Detroit +8.5. If they both cover, you win!

I must have profited $50k betting just Wong Teasers $500-$2k at a time that year. The funny thing about sports betting is that nothing lasts forever. You have to constantly be looking for new edges and tactics to win. I’d be shocked if Wong teasers still work today. I don’t play them any more because sportsbooks have all changed their odds to make it nearly impossible to have an edge. But besides that, the rules of the NFL have changed.

Since the year 2000 the odds of any NFL game margin of victory landing on 3 is ~15%. The other “key number” is 7. The game has landed on 7 about 9% of the time. But now the kickoff is different. The extra point is farther. Two Point conversions are attempted more often. And coaches are following analytics more closely, which probably creates more runouts where teams win by 1 and 6 or 8. 1 because teams go for 2 instead of the extra point to send the game to OT. And 6/8 because teams go for 2 when they’re down 8 after a touchdown in the 4th quarter now.

I just ran the math actually. Since 2024 Week 1 through whatever week we’re in for 2025 there have been 419 games played.

Margin of Victory = 3

Margin of Victory = 7

13.60%

7.40%

So I guess my intuition is correct there as both of these are down quite a bit from historical figures. I’d expect that to continue to diverge.

In fact look at this. 6 is the new 7 (pause for the kids to say…6, 7?!)

Here’s a chart with 2000-2025 margin of victory (I couldn’t find a chart that stopped after 2023) along with the 419 games from 2024-present:

6 has flipped 7. Meaning maybe don’t buy up to +7 if you’ve got +6.5 already. But buying +5.5 up to +6 might become a thing worth spending on. Strange times.

Anyways, I didn’t mean for this to turn into an edge-finding session for betting the NFL.

The point is this: From 2015-2017 I think I had a big edge betting NCAAF and the NFL. Like massive. Between Wong teasers, following sharp bets from a friend for NCAAF (Shout out to Lev!) and my poker results, I built up a nice little bankroll.

But the real unlock came when I made a connection between an under-followed fantasy football handicapper & totals in the NFL. I found that this fantasy football guru had a magazine, a crappy website, and weekly predictions for all player stats. I backtested all of his projections for several seasons back. And they were good. Very good.

All I had to do was add up the player totals for both teams and I could profitably bet any game that was 3+ points off that number. It was a money printing machine.

By the time the 2016-2017 football season ended I was regularly betting $15k-$20k on NFL totals per game. And because the NFL market is huge I wasn’t having any trouble getting down before the line would change. So I had a lightbulb moment.

I’ll start a hedge fund!

As poker players we’ve all heard it. “If I give you $500, can you turn it into $1,000?”

Well I could finally answer: “YES! (maybe)

In late August 2017 I raised $40k from 1 friend. And got another on board for $30k in early October. I took a little freeroll for myself and we were off to the races.

How did it go? Pretty darn well.

This investor hopped in when I started heating up in October

Not a bad little return for 6 months of work

After a banner season I’d found the golden hand of Midas himself! So I did what any aspiring genius would do. Scale it!

I focused my energy on raising capital for the 2018 season. And by focused, I mean ignoring it completely then scrambling like a mad man after the WSOP. I got 8 people to commit $50k each to my growing little fund.

I even incorporated it. I loved the name. Boundary Peak Capital. (Boundary Peak is the highest point in Nevada. Ok, end nerdiness).

A $400k bankroll meant I could bet $8k-$24k per game for the fund. Plus my $10k-$30k on top of that. Up to $54k a game? Holy shit. I was excited.

Spoiler alert: Boundary Peak ended up where many Vegas dreams end up. The bottom of Lake Mead. It was not a good season.

I’m not really sure what happened. I was doing most everything the same. I’m sure some of it was bad luck. But mid way through the season I was “finding” too many spots to bet. When I won before I would bet 3-5 games per week on Friday night when my projections came out. In 2018 I constantly had the charts up into Sunday morning when the lines are sharpest (read: worst for betting). Looking for something to qualify according to my numbers.

There’s a fine line between pressing an edge, and just pressing. I was doing the latter.

All told I lost around 30% for investors in the 2018 season. Not horrible. But enough for me to close the doors on the hedge fund idea. I was basing my own personal wager sizing off of all the money I had in the world. So I also lost 30-40% of my own bankroll too. That was a tough lesson in diversification that I still have yet to really learn.

At the end of the day I think this hedge fund for sports betting can work as a business model. But unless you’ve got a Billy Walters size network. I think you’re better off finding small edges and keeping them to yourself.

What do you think? Would you invest in a sports betting fund? Can sportsbooks really be beaten in the long run?

These days I bet for myself only. And I bet around $1k-$3k per game. I’m a small winner with the strategies I use now. I’m not looking to improve because the time commitment is just too high for the gains I expect to be able to make in the age of AI.

Speaking of AI, a fun fact about me: I cashed in the Circa Sports Million contest the first year that they ran it. We got 3rd place under the alias “The Bet Bot.” That paid like $40k and I split it with a partner. The idea was to be a tout without having to put my face on that space. But it never felt natural to tout. Not to mention I don’t think I have a big enough edge for that anymore. There are definitely some touts who win. But most are just marketing scammers like Vegas Dave and Sean Perry.

Stories for a future email. Alright, that’s enough for today.

Your favorite degenerate idea-man,
Art Parmann

“If you give me $500, I actually CAN turn it into $1,000!”

How'd I do?

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