Hobby to Side Hustle
APRIL 1ST, 2022
Welcome to Hobby to Side Hustle! I hope you find this article interesting, entertaining, and informative as I recap what I have learned playing MLB DFS over the years that led me to a very profitable 2021 MLB season.
Let’s get the introduction out of the way so you know a little bit more about me. My name is Brandon Leach, aka PresidentLeach on Twitter, Draftkings, Fanduel, and Yahoo. Growing up in Braves country, I have always been a huge baseball fan. I started playing MLB DFS on Draftstreet back in 2014. Draftstreet, what the heck is that? All I remember from those days was wondering if I was going to roster a closer in one of my three pitching slots and spend up for two aces. From 2014-2016, I spent way too much time diving into advanced stats and trying to build the perfect 2-2-2-2 stacks to take down the $1 Solo Shot on Draftkings. I was sweating every pitch, every AB, determined to make a couple dollar profit. Well thanks to a new Alabama law, my DFS career was cut short in 2016 as DFS was banned in the state. Fast forward to 2019, and we are back! Draftkings is now considered a game of skill and Alabamians can now get back in the DFS streets. This gave me a new set of goals: to truly learn how to be profitable in DFS and scale up my play to turn my hobby into a profitable venture. Well if you want to be profitable in MLB DFS, you got to have the best projections and that’s without a doubt The Bat from Derek Carty. Through grinding the low dollar lobbies, I started to become a profitable player and learning how to build solid MLB lineups.
It is now 2020, time to really commit to a bankroll strategy and see what kind of ROI I can achieve. My starting bankroll was $100, with a plan to play 90% cash and 10% GPP. Although the season started later than we all expected, I was able to turn a profit while continuing to learn the right way to build cash and GPP lineups. But is all this work and research really worth turning $100 into $500? That all changed one night in August. I was suppose to be golfing, but it got rained out. So last minute, I decided to build a lineup for that night to have a little sweat. The Chicago White Sox against Jon Lester were popping in all of the top lineups with The Bat. So with little preparation, that seemed like my best route to take. But to make the lineup somewhat unique, I added in the bottom of the order 2B I had never heard of, Danny Mendick. 10 runs and a Danny Mendick HR later, I would find myself at the top of the lower dollar single entry contests. I finally had it, a four-digit profit day. Now I feel on top of the world and ready to go all in on the 2021 season.
In total, I made $3600 in the 2020 MLB season. Not bad for a starting bankroll of $100. It’s time for a new set of goals, however.
Turn $1,000 starting bankroll into $10,000
Track performance across different cash and GPP contests (I was too cheap for Rototracker. In hindsight, that would have saved me a lot of time)
Have a 5 figure day
Qualify for the FBWC live final
So with $1,000 in my Draftkings account, I was ready for the 2021 MLB season. I still planned to follow my 90/10 rule of cash versus GPP. My cash contests were mainly split between double-ups and head to heads, with a sprinkle of triple ups. For GPP, I planned to enter the SE contests between $1-$12 with a single dart in the $1 or $4 20-max GPPs. I got off to a hot start in both cash and GPP and made a $1,800 profit in April. As the bankroll grew, I scaled up my play to continue entering about 10% of my bankroll every night. I started to lean a little heavier on the GPPs as I felt like I had an edge in the single entry contests. In most cases, ownership tends to consolidate more in the single entry GPPs, which played perfectly into my style of building contrarian lineups. Little did I know what was in store for me in May.
May 10th, 2021. A little 5-game Monday slate. I entered my usual contests, about $200 across different cash lineups and about $50 in different SE, 3-max GPPs. A lot of ownership was going to Red Sox in Baltimore and the Angels against the Astros. But I took a different route. The Reds in an interesting spot in a not so hitter friendly PNC Park against a hyped up young arm in Mitch Keller. With a 5-man Reds, 2-man Angels stack, I took down the $25 Single Entry Skipper for a $1,500 win. All in all, I won $3,500 that night, what a win! I felt like my $10,000 profit goal was attainable. Later that week, I withdrew a little over $1,000 to recoup my initial deposit to start the season. But I am having success at this single entry thing, maybe I should step it up to the next level. And that brings us to the following Monday.
May 17th, 2021. A larger slate than the previous Monday, but the ownership is heavily condensed. The White Sox (here we go again) are popping in all the optimizers because of a matchup against JA Happ. Gerrit Cole (80% pOWN) and Yu Darvish (50% pOWN) are carrying the pitching both in easy matchups. So how do I build a unique lineup on this slate. As I start to build lineups one thing becomes apparent, getting off the White Sox, Cole, and Darvish is going to be extremely difficult. But there he was again, staring right back at me, my guy, Danny Mendick. A 4% owned player on the team I want to stack. With this, I feel like I can roster the two aces. Add in a Shohei Ohtani, Taylor Ward chalky 2 man, that leaves one position left on my roster. Did I mention I grew up in Braves country? As a Braves homer, a 1% owned Austin Riley looked like the perfect 3B to round out this somewhat chalky team. I enter this into my usual SE contests, but decide its time to scale up. A $121 entry into the SE battery, first place $10,000.
The slate begins as me and my wife head to the gym. As we head that way, I start to notice the White Sox putting up some runs. Sweet! Could be a good night but I know they are pretty chalky. As I get ready to start hitting the weights, I give the MLB app another update. And BOOM! Danny Mendick grand slam! MY GUY! That instantly catapulted me up to the top of the leaderboards. I had never seen “Winning $10,000+” on the top of my DK app before. But slow down Brandon, it’s 7:30 central time, still a lot of baseball to be played. I don’t even know if I actually worked out or if I just refreshed my MLB app after every pitch. As I bounced around the top 5 of the contests all night, I knew I had a chance. As we get home, I turn on MLB Network, and what do I see? A live look at the Angels game as Ohtani goes yard! A few minutes later, Yermin Mercedes takes the Astudillo 3-0 lollipop deep! (Side note, if you don’t want someone to jack a 3-0 bomb off you, don’t put in a position player to pitch.) My team is popping off! But dang, the Braves are getting completely shutout by the Mets. I tune into the local Bally broadcast to see Austin Riley’s last AB, and I can’t believe what happens next. I stare in awe as Austin Riley sends a shot into the right field Chop House in a meaningless 3-0 game. I am clear in first at this point, except for one problem. That 80% owned Gerrit Cole stunk. And there is one guy who can chase me down that faded him and went with Casey Mize. Although my players are done, the sweat continues as Mize is dealing in a late west coast game. Not giving up a run through 7, it looks like Mize may run me down. But thank goodness for kid gloves and pitch counts, because Mize gets removed with 2 outs in the 8th. Even with the soon to be Mize win bonus, it looks like I am going to hold off and take down the $121 Battery for the $10,000 top prize! Are you kidding me? Profit goal, 5 figure day goal, all reached and its still early May. What a season so far!
After a $10,000+ withdraw to secure my profit goal, one goal still remained, qualifying for the FBWC. The lure of a live final to me was getting the chance to meet some of the GOATs of MLB DFS and having a shot to go toe to toe with them on the biggest stage. With about $5,000 left in my DK account, my goals for the remainder of the season would be to get back to $10,000 in my account by the end of season and to secure a ticket to the FBWC. Well, that didn’t go as planned.
The dog days of summer hit hard. June was a terrible month GPP wise for me. With no top finishes, I suffered about a $2,000 hit on GPPs alone in June. My edge in cash was also fading as the fish started to filter out of the MLB season. A small profit in cash helped lessen the downswing as I had to learn to cutback on my nightly contests. The $121 single entry was now out of my budget, as I refocused back to the $1-$25 single entry contests. July started off about like June. On nights I went contrarian, the chalk popped off. The nights I went chalky, they busted. Confidence was at an all-time low as I slowly watched my DK account balance drop each night. But nevertheless, there I was entering contests every night, over and over again.
July 7, 2021. Matt Harvey, in Baltimore, against the Blue Jays. If that isn’t a recipe for chalk, I don’t know what is. If you have made it this far, you have learned my strategy for the most part. Eat a little bit of the chalk but find ways to make a contrarian team around it. Ownership was extremely condensed, especially for a 9-game slate. A 60% owned Zack Wheeler and a Blue Jays 3 man seemed fine as along as I could build around them. The Nationals against Chris Paddack were showing as one of the highest leverage stacks and were coming in at basically no ownership. The perfect compliment to balance out what was going to be a 50% owned Vlad Jr in my Blue Jays 3 man. As the night started, the Blue Jays did exactly what everyone expected them to do. Took care of Matt Harvey early en route to hanging 10 on the Orioles. But I got just enough of that chalk as my 3 Blue Jays combined for 9 hits. I am sitting solidly in the money with my huge leverage still to play. The Nats came in about as expected. Less than 5% on all players with my 8-hole Victor Robles at 0.35% owned. The Nats come out hot as Chris Paddack continued his puzzling disaster of a season. 15 National runs later, and there I am again, on top of the SE leaderboards for a $4,000+ night. My third $25 Skipper win of the season! I have new energy and ready to complete those final 2 goals: regain $10,000 in my DK account and qualify for the FBWC.
I started to reenter the $121 SE tournaments and mix in different FBWC qualifier and satellite contests. But to no avail. Red night after red night, even in cash. All that work building a cash lineup to have a 2% ROI in double ups in July. As the calendar turned to August, I made the decision to completely stop playing cash for the remainder of the season and focus more on the SE GPPs and FBWC qualifiers. Well, August began the same way July ended. Devastating losses to barely miss out on winning satellites and qualifiers. As the downswing since that $4,000 night continued, I questioned if it was time to hang it up for the season. And then the night that changed my life.
August 12, 2021. After a disappointing early slate, I figured I would pass on the late night 3-game slate. Besides, the Padres and Yu Darvish were insane chalk in Arizona. But as my wife left for her night shift job, and I was feeling burnt on MLB The Show, I wanted to have some action this night as I had all night to chill and watch my favorite non-Brave, Shohei Ohtani. As I started to build lineups, the chalk construction became pretty apparent. Even on a night with Ohtani, German Marquez, Logan Webb, and Jose Berrios, Yu Darvish was going to be 80% owned against the Diamondbacks. The Padres hitters were about just as high as there weren’t many good hitter spots on this slate. After building 50 lineups on LineupHQ resulted in 100% Darvish and Padres stacks, I decided to exclude them to see what The Bat preferred as the next best spot. There was some Blue Jays stacks in there as Ohtani had a few high walk performances, putting his control in question. But I noticed one other team was mixed in the 50 lineups. The Diamondbacks. Huh? That doesn’t make any sense. I thought Darvish was the lock of the century against them. But The Bat was really liking the Diamondbacks relative to the other teams on this slate. I have already lost consistently for the past month, what’s another slate. So I decide to go contrarian and build the Diamondbacks against the 80% Darvish. Darvish can be so good, but when he’s bad, he’s really bad. I figured anyone fading the Padres likely are going with the Blue Jays, so I decide to add in Ohtani as direct leverage against those builds. And just like that, my lineups is set. Webb, Ohtani as the pitchers, 5-man Dbacks stack, chalky Machado and Cronenworth, and Jared Walsh as a oneoff 1B with HR upside. I like my strategy for the night. I enter the $12 and $5 SE contests, and the $15 large-field GPP. Because my lineup is so unique, I decided to also enter the smaller $15 GPPthat opened up right before lock. $47 of entries seemed like a fine total for a night I was taking some big risks.
The slate starts off about as expected. Darvish carves up the Dbacks with 4 K’s in two innings. Well, looks like another losing slate, as I close my DK app for the night. And then Darvish fell apart. After a leadoff hit to the pitcher, the Dbacks started to hit Darvish hard and baserunners reached one after another. Capped of by a David Peralta 2-run blast into the hot tub, Darvish would face one more batter before being removed for injury. Everything was set up for me now. Dbacks off to a good enough start to get Darvish out of the game, Ohtani pitching well against the Jays, Logan Webb carving up the Rockies, and German Marquez giving up 7 runs in 4 innings. But if I had learned anything from my season so far, you cannot refresh the DK app after every pitch. The emotions of seeing one event swing you thousands of dollars is too much. The night concludes with Webb and Ohtani both getting the W, and the Dbacks putting up 12 runs against the Padres. My remaining players did pretty well, but there is some doubt as I know my 2 points from Machado may be my downfall. I tell myself I will not look until the final pitch of the night. I have a feeling I am in the top 10 in most contests, making a profit of anywhere from $500-$2000. What I saw next I still can’t believe. I opened my DK app to see the biggest number I had ever seen before, “Winning $71,750”. I fell to my knees in shock. My team had done it. First place across all 4 contests I had entered! As I sweated potential stat corrections, I lie awake trying to figure out how I am going to tell my wife. I decided a screenshot would suffice. That text was quickly followed up by a return call with the only person in more disbelief than myself. She knew I enjoyed DFSand was always supportive of my hobby. And after the first 5-figure night, she was extra supportive as I clearly was able to make us some more vacation money.
I decided to tweet out my performance the next morning and was quickly bombarded with friends checking the legitimacy of my posts, trying to learn how they could get into DFS. They didn’t see the daily podcasts, 2x listening to Jordan Cooper’s Theory of DFS audiobook, over 100 days of consistently playing multiple MLB slates a day. But I was happy to provide advice and willingness to teach them some of the things I had learned. I guess that’s why I am writing this today. I am no DFS pro. I am just a diehard MLB fan with a desire to be good at DFS. It’s not all sunshines and rainbows. The nights where your hundreds of dollars of entries result in one $1.80 H2H win really teach you not to let the downswings get to you. But the reward of grinding a profit and hitting big after months of playing daily makes it all worth it. I plan to write more of these posts as we move through the 2022 MLB season. I will break down my goals and plans for this season, strategy on slates, and who knows I may be able to land that elusive FBWC ticket after all.