Listen in as Jason Mezrahi of Win Daily DFS joins Knup to talk about his new book along with his new website, where he is helping people win at daily fantasy sports and life.

Show Notes

Ryan Knuppel: 00:00 In today’s show, we talk to Jason Mezrahi of WinDailyDFS.

Recording: 00:04 This is cray, this is cray, this is crazy.

Ryan Knuppel: 00:06 Everywhere you turn, it’s the same old sports talk, the same headlines, the same news and the same boring information. This podcast is here to change all of that. We bring you hot sports takes, winning sports betting strategy and pics, reliable gaming industry news and breaking interviews with some of the biggest names in sports business. My name is Ryan Knuppel. Welcome to the Knup Sports Show.

Ryan Knuppel: 00:26 Hey, what’s up guys? It’s your host, Knup, with episode number 52 of the Knup Sports Show. I appreciate each and every one of you tuning in, listening to this show when we bring it. Today we have a special guest. We have Jason Mezrahi of WinDailyDFS. He is with us. He joins us and he talks all about his start in this industry and what WinDaily is. Man, it’s a great interview and actually, it’s kind of a funny story.

Ryan Knuppel: 00:49 We actually recorded this interview probably, three weeks ago, several weeks ago, and with all my travel and some of our stuff going on, I know I’m making some excuses here, but we have not got this thing published until now. But guess what? It’s getting published now and it’s no better time than now, because Jason has announced a live event that wasn’t covered in the interview, as you listen. But I wanted to make sure I gave a little shout out to it now and I’ll actually put it in the show notes, as well.

Ryan Knuppel: 01:16 He’s having a live event. He’s joining up with another guy, Scott of BallStreet Trading, and him and Jason, Jason and Scott are putting on this awesome event in downtown New York, at Brother Jimmy’s, on June 7th. So Friday, June 7th, coming up couple of days. If you’re listening to this, this week, it’s June 7th at eight o’clock they’re going to do a live event where they do some trading and they use the BallStreet app. And then also, some of the DFS tools from WinDaily and a really put on a great event with some free food, free drinks, some drinks specials. All sorts of stuff going on at this event.

Ryan Knuppel: 01:50 If I lived in New York, I’d be there in a heartbeat. I don’t, so I probably won’t be able to be there. But if you do live in that area, I urge you to check it out. Go talk to Scott, go talk to Jason and just get to know those guys. Really good guys in this industry and I think you’ll enjoy this event. So wanted to give a little plug for that. Again, the details will be in the show notes, so you can check that out later.

Ryan Knuppel: 02:12 But yeah, so this interview with Jason took place a few weeks ago, but I think you’re going to enjoy it. You’re going to hear a little bit about his daily fantasy adventures, getting into this industry. And then he released a new book, a WinDaily book. And then a website and a platform and all this good stuff to help you win at your daily fantasy sports and in life, as he likes to say. So without further ado, let’s jump into the interview.

Ryan Knuppel: 02:40 All right, I’m here today with Jason Mezrahi of WinDaily. Jason, are you with me?

Jason Mezrahi: 02:45 I’m with your brother. How you doing, Ryan?

Ryan Knuppel: 02:47 Oh, I’m doing great today. Hey, thanks a lot for joining me, Jason. I appreciate it. For all of you listeners out there, Jason is a big time DFS player, has been doing this for a long time and recently launched a project where he actually wrote a book around what he did and some of his experiences. And that’s what we want to talk about today. Jason, explain a little bit about WinDaily, where it came about and what you have going on in that space.

Jason Mezrahi: 03:12 So to be fully transparent, I’ve been playing DFS for a long time, basically since 2012, 2013. I’ve been lucky enough to have some life changing moments. And then about a year and a half ago, my wife had his crazy idea that I should write a book. And I looked at her like, why would I write a book? I’m not a writer, I have no passion to write. And I kind of just blew it off and didn’t really think twice about it. We talked about for maybe a minute or two and I said, “Yeah, I got some cool stories. I’ve been in the playboy mansion and the world around this is changing with sports betting and fantasy is, it is what it is at this point.” I said, “It’s a cool story, but I really don’t have that much passion to write.”

Jason Mezrahi: 03:51 So then, another thing happened to me and somebody else crossed a social media platform, just randomly approached me and said, “What do you think about writing a book?” And not really knowing my personal story, he asked me the question regardless, and I kind of said, “Wow, my wife’s telling me about it, now this random guy on Instagram is telling me to write a book. He doesn’t even know me.” So I put two and two together. I said, “You know what? The universe was talking to me.”

Jason Mezrahi: 04:21 So I called my wife. I said, “Listen, I guess I got to write a book.” So from there, I just kind of jumped all in and I went about the project. I got people around me to help me out, friends, family members, professionals, and we set out to write this book.

Ryan Knuppel: 04:38 Man, that’s crazy. So I mean, to write any kind of book, you’ve got to have some, like you said, you have some experiences, but you have to have some knowledge. You have to have some experience. You have to have some real life experience in this. I mean, tell us about your DFS experience. I mean, have you been a professional player or are you just a hobbyist? I mean, tell us a little bit about, I guess, how you were credible to write this book in the first place?

Jason Mezrahi: 05:00 So basically, I started off when I started seeing all these commercials on TV, on the radio, on the internet. Basically saying, FanDuel and a couple other sites at that point, were out there. And when I first heard about it, nobody told me about it personally. I just saw a random ad and I didn’t really know anybody who was doing it. And I jumped right in and said, “This was made just for me. I love competition, I love sports and I love money.” So it combined all my passions.

Jason Mezrahi: 05:26 So I dove right into it and what the DFS slate looked like in 2012, 2013 wasn’t anything like it is now, where there’s a hundred different websites giving you all these optimizers, articles, podcasts. So, I was out there on my own and there was a learning curve. It took me about a couple months to put together a couple of dollars, turn a profit. Then seasons change, you go from one sport to the next sport, you got to learn all over.

Jason Mezrahi: 05:54 But then after the first year I got my learning curve past me. Baseball came back around and FanDuel was launching their biggest, first prize pool ever and first place was $155,000. Over a course of a couple of weeks, I basically got a couple qualifier tickets to this tournament. It was a pretty big tournament. It was the biggest tournament that I ever really took part in at this level, at this point in my career. And I was lucky enough, when the night was over, to cash the first place ticket that was over $155,000.

Jason Mezrahi: 06:31 From there-

Ryan Knuppel: 06:31 Wow! Congrats.

Jason Mezrahi: 06:32 Thanks, bud. So from there, I basically qualified to a Playboy Mansion event and was able to take one of my best friends from college and take him out to the Playboy Mansion. And then, basically playing every day for the past six, seven years, I’d qualify for another event. Didn’t have the best showing at a DraftKings World Championship and then, most recently, about two years ago, I qualified again for a DraftKings Basketball World Championship this time. And I was lucky enough to take home second place, which was $300,000.

Jason Mezrahi: 07:05 So at that point, I really didn’t have the idea to write this book. I was never a big touter. I wasn’t on Twitter or on social media saying I’m the best, I’m the best, I’m the best. I just knew I worked really, really hard and I put the time in. And then, when the universe kept on pointing in my direction, said, “Hey, you should write this book.” I just went all in and did it.

Ryan Knuppel: 07:26 That’s crazy. So, you and I do have one thing in common and I want you to talk a little bit about this. I actually made it to the Playboy Mansion as well, through FanDuel, and it was unbelievable experience. But I want to hear your experience at the Playboy Mansion. You kind of glossed right over that, but that’s kind of a big deal. Right? That’s something that I would say, very few people in this world can say that they’ve done, is hung out at the Playboy Mansion. So give us a one or two minute teaser about what it’s like at the Playboy Mansion.

Jason Mezrahi: 07:55 So it’s basically like going, we went with StarStreet. They were the first ones who did it and a lot of people who are listening to this, right? Never heard of the website, StarStreet. But they were the ones smart enough to work the deal to get a Playboy Mansion qualifier and it took me a long time to get there. But getting there, they put us up in a beautiful hotel in LA and then they took these shuttle buses over to the Playboy Mansion.

Jason Mezrahi: 08:22 And what I can compare it to or the best analogy I can give it to, is when you go on those middle school trips and all your friends are getting together and you’re going to the aquarium or you’re going to a baseball game. It’s like the adult version of that, but it’s a lot better. You get those butterflies like, oh my god. You see all these different mansions and you roll up to a mansion that you’ve heard about and you’ve seen on TV, you see on MTV Cribs. And Hugh Hefner to me, I would probably trade my life for maybe, a couple of professional athletes or Hugh Hefner.

Jason Mezrahi: 08:59 Entrepreneur did what he wanted to do in his life and he really lived a long, successful life. He actually, he had some perks to his setup, but from an entrepreneurial standpoint, he pushed the envelope when nobody was supporting him and he kept on going at it and going at it. And he was a perfectionist and he put the work in and he built an empire, with his dream and his hard work. And rolling up there, everything was, we had access to everything. We had access to the grotto, we had access to his little zoo, there was peacocks walking around.

Jason Mezrahi: 09:36 There was girls, there was a bar, there was beer pong tables, top notch food, everything that you can imagine for a grown man to enjoy, was at your disposal. And my wife was nice enough, she was busy, she had plans. That I was able to take my best friend to the event. And so now my best friend when he introduces me to people, that don’t know me, he’s like, “This is Jay. The guy who got me to the Playboy Mansion” and then it’s a whole conversation like, “You went to the Playboy Mansion? How? How did this happen?”

Ryan Knuppel: 10:07 Very cool.

Jason Mezrahi: 10:08 We’re the only ones that have proof of each other being there, because we were there with each other.

Ryan Knuppel: 10:14 That’s awesome. That’s such a cool story and I’m sure you have more stories like that throughout this book, but we’re speaking of Hugh Hefner and some big names and things like that. And one thing that really stands out, when you look at just the cover of this book and the back of this book is, you got some pretty good endorsements here, some pretty big names endorsing you on this. That’s pretty cool. You got guys like Pete Rose, Warren Moon, Adam Schefter. I mean, some pretty big names here. So congrats on that, I guess, is all I wanted to say in that realm. I mean, how’d you go about doing that? I guess you don’t have to go into how you go about doing that, but I mean, Pete Rose, come on man. I mean, how’s Pete Rose on the cover of your book?

Jason Mezrahi: 10:52 You know, it’s simple things, man. When I first set out to write the book, I said, there’s one guy that I’d really love to be a part of this. If I can have one person to be a part of this, it would be Pete. And I simply asked. I thought maybe I had a 10, 15% shot at max, but I was able to speak to his team and I just asked. And I did have to ask more than once, I’ll give it that. But I asked and I still have, people are asking me, are you going to do an Audible version? I said, “Listen, I don’t have the voice to do Audible, but I have a person in mind.”

Jason Mezrahi: 11:30 I’m not saying I’m going to get them. I haven’t even thought about how to approach him and, but I think the funniest person I can get to read the Audible, if I can make it happen. So if you’re listening, listening right now, Charles, I would love to get Charles Barkley to do the Audible, but I’m not saying. Maybe if I had the 10% chance of Pete, maybe I’ll give myself a 5% chance of Barkley because he’s busy on TV. But if I can have one person read the Audible, I think it’d be pretty hilarious if me and Barkley did it together and maybe share some commentary together, while it was recording. That would be cool things [crosstalk 00:12:05]. And the way he goes about his thing, so it’d be pretty cool to have him on.

Ryan Knuppel: 12:10 Yeah, that’d be epic. And there you go, listeners, there’s a piece of advice just right out of his mouth. All you got to do sometimes, is just ask. You never know, just ask. So, all right, one more thing about the book and then I want to shift gears here a little bit. One of your, I guess it’s not a quote, but a thing that really stood out to me, and this is really from playing myself, and it’s so true. And I don’t know if, if some of you listeners haven’t played DFS this statement was so true.

Ryan Knuppel: 12:36 And it’s on the back of your book. It says, “I’m not sure what’s more painful, losing a bunch of money or being so close to winning a bunch of money.” And that is like DFS to a tee because you go through those nightly grinds, those nightly sweats, where you’re so close to winning, you’re winning, you’re losing. Next thing you know, your first, now your 20th and you see your bank roll going up and down, as that happens. I mean, if you haven’t experienced that as a DFS player, Jason, explain the thrill of that or the let down, a lot of times, of that experience. When okay, you didn’t lose the money, but man, it’s like missed opportunity. I had it and now I don’t. Explain how that feels.

Jason Mezrahi: 13:16 Yeah, I did a whole chapter about it. It’s my Buster Posey story. I’m not going to share with you because it would take too long to share.

Ryan Knuppel: 13:23 A little teaser. Yeah, that’s okay.

Jason Mezrahi: 13:26 But it’s definitely true to me. I’ve dealt with it so many different times. So if I start a night and say I got, 1000, 2000, 3000 dollars at risk and within the first 10 minutes my pitcher just gets blown up or a football player has a concussion or gets hurt or a basketball player turns an ankle. I just take the punch to the gun and go [inaudible 00:13:50], I’ll get them back tomorrow.

Jason Mezrahi: 13:53 The most painful nights are the nights where you’re, like you just said, you’re winning and you’re doing good and your team’s doing better. And these tournaments are so top heavy where first place can be $50,000, especially in these qualifiers. And second place can be a box of steak knives. You basically get your money back. And so, it really comes down to those nights that are the most painful, because it’s the opportunity that you lost, that ticket that you didn’t get.

Jason Mezrahi: 14:24 And these tickets are so hard to come by and these big [inaudible 00:14:27] to come by. And when you have that optimal lineup and you’re really in contention, it’s a really big blow to deal with. But I think the bigger lesson that people like myself and Ryan have witnessed, is when you deal with these daily defeats and they consistently happen to you, it’s kind of like your coat of armor. And it’s kind of like you are a little bit tougher the next time around and the next time around. And now I can laugh about the Buster Posey story and I can laugh about all the bad beats I had. And the last second changing of thousands of dollars going from one side to another side.

Jason Mezrahi: 15:05 So I think they’re easier to stomach when you had a couple of big ones. If you’d never had a big one and you just had a lot of those defeats, you can’t laugh about it as much. But it’s definitely tougher to me when that happens and it’s a tough thing to swallow.

Ryan Knuppel: 15:21 For sure, definitely. Okay. Well, I urge everyone to get a copy of this book. It’s out on Amazon. I’ll let you talk about it here at the end of this discussion, Jason. But definitely go grab a copy of WinDaily. It’s a great book. But on top of the book, now you have another project going on. You’re not only on a book, you’re bringing this onto the web. Is that correct? What do you have in terms of a website around this?

Jason Mezrahi: 15:46 Yeah. So when I was done with the book, I patted myself on the back for 30 minutes and I realized, wow, if I don’t back this up with anything, the brand, the movement, the mantra of win daily and having these small daily victories and winning at life and everything else is going to fall to the side a little bit. Because there’s so much going on in everybody’s lives.

Jason Mezrahi: 16:14 So I figured, what better thing to do then to launch a website, give more of my time and give more of my access? And basically, what I’ve built personally, with my projection models and my process, and give that back to the rest of the community that needs information daily. Because we all play, pretty much, every day. You know the pros do and you know a lot of other people who are just dabbling. They’re going to be playing two or three days a week regardless.

Jason Mezrahi: 16:41 So what I put together was a team of other DFS pros, that I know within the industry. A director of content, Scott Angle, who’s been in the industry for about 25 years. And with that, we have a team of about 14, 15 people. We have projection models that will help you hand select the right picks for those given days. We have four or five articles get published by professional DFS players and writers daily. And a podcast I get to shot every single day, on top of it.

Ryan Knuppel: 17:15 Very cool. I mean, that sounds awesome. Now you kind of touched on this, but I mean, what kind of player is the site and the book for? I mean, is this for the casual DFS player? Is this for the pro? Is this for anyone interested? Is this for somebody who’s never heard of it? Who’s going to enjoy this the most?

Jason Mezrahi: 17:31 I think it’s for everybody, I really do. I think it’s for the guy who wants to just come on, guy or girl, who wants to just come on and get some information about the MLB slate today. On the podcast that I recorded last week, I dropped some knowledge outside of daily fantasy sports.

Ryan Knuppel: 17:48 Nice.

Jason Mezrahi: 17:48 I dropped the stock tip that I thought was something that, I thought it was a good idea. It was an IPO that was launching, I don’t know how much your community or yourself follow the stock market, but I dabble from time to time. Pick some winners if I can. And I put that out there into the universe and the stock, IPO, I think they opened up at 45. I’m pretty sure it closed that day around $70 and now it’s trading around 75. It’s called Beyond Meat.

Ryan Knuppel: 18:19 Nice.

Jason Mezrahi: 18:19 So I’m going to try to bring as much to the table as possible, more from a mindset approach. Try to basically, yes, DFS is going to be a focus, sports betting will be a focus. We have people handicapping and giving you picks and giving you education. But I want to also teach the community how to have the right mindset, how to go about things. So I think, when people first come to the site, they’re going to get hit with a lot of DFS and horse betting tips. But I think if we’re looking six months out or a year out, you might get more mindset, process, education, from a larger scope, outside of just sports and fantasy.

Jason Mezrahi: 18:59 That’s where I’m hoping to take it, but we’re looking six months down the road, a year down the road. But it’s still only going to be a fraction, just throwing little gems in here and there on how to work different avenues outside of just daily fantasy sports and sports betting. But like I said, the focus will be to anybody who wants to get an edge, anybody who wants to get some free information. The articles, the podcasts, our models are mostly free. They’re free for now and they’re going to be free for, I would say 80% of the site is going to be totally free, forever. So if you want free content, if you want to join a community, you want access to pros within the industry, will provide that for you.

Ryan Knuppel: 19:42 Love that man. I love that you’re mixing in some life too. And you put it right on the cover of your book, “winning at daily fantasy sports and life”. So you’re mixing in some gems, as you would call them. That’s awesome. So let’s mix up this conversation just a bit and I wanted you to tell you, man, I really enjoyed meeting you at the Betting on Sports America Conference, that we went to here. What was that? A couple of weeks ago, as of today.

Ryan Knuppel: 20:06 Did you enjoy that conference, man? I thought it was awesome. It was unlike anything, I guess, I’d ever been to in terms of conferences. I thought the energy was amazing. I’ve been asking everybody, I just wanted to get your quick minute, two minute thought, on how that conference was for you, yourself.

Jason Mezrahi: 20:22 It was eye opening. It was eye opening to see everybody within one room, with shared passion for sports, for fantasy, for sports betting, for entrepreneur-ism. We’ve talked a couple times prior to meeting each other out there. But one of the biggest things that I loved about live qualifiers is, was you were able to see other people within the industry. And that’s what these conferences do.

Jason Mezrahi: 20:48 So I’m all about the conferences and I run a consulting business as well. So anytime I get to go hang out with other people within my industry, it’s a no brainer. I’m jealous that I’m not going to be able to make it next week to Boston. And I know that you’re going, right?

Ryan Knuppel: 21:03 Yeah, yeah. I’m going to make it. So I’ll be there again, yeah. You won’t be joining me this time around?

Jason Mezrahi: 21:09 But yeah, the conference. No, I’m not going to be there. I have a newborn. So pulling off these week, the weekend trips or these week trips are tough for me at this point. But yeah, the conference was amazing. It was in my backyard. I’m from New York, so just an hour drive to get to New Jersey and they really did it right too. To be able to go to Meadowlands, check out FanDuel’s sportsbook, check out everybody in the industry, where it’s going and it’s really going to a good place.

Jason Mezrahi: 21:39 There’s a lot of smart people behind the movement and to meet people like you and Mike and Scott, it was great to see everybody. It was overall, an eye opening experience for me, to see where everybody else’s head is at. But it looks like we’re all in this together and it’s a great, great movement that’s about to take place in America.

Ryan Knuppel: 22:01 Yeah. And it’s fun, like you said, to have a little community behind what’s going on here. And that’s what those conferences really provide. So yeah, that was awesome. And I’m sure there’ll be more in the future, even though you’re not going to Boston, we’ll definitely plan to meet up at a future one or something. So man, well awesome. I won’t keep you much longer. The only thing I really want you to talk about now, is how in the heck can somebody get a hold of this book? Where can they find you? Where’s the website? Just give us all the details, man. Where can we get all this stuff?

Jason Mezrahi: 22:33 Okay, so the book is on Amazon. 99 cents for the Kindle, 5.99 for the paperback. And just to let your listeners know, I’m not trying to monetize the book. Every dollar that came in so far from the book sales, I actually donated it back to the Jimmy V Fund. I’m not really trying to monetize this book for any reason. I’m trying to get it out there as cheap as Amazon will let me sell it. And every dollar that came back so far went to, like I said, the Jimmy V Fund.

Jason Mezrahi: 23:03 So just type in WinDaily on Amazon and it’ll pop up. We had a good launch. We’re, I think we’re the number one release in fantasy sports and gambling as well. We’re actually competing with Harry Potter somehow. That was considered a fantasy sport. But yeah, you can find it on Amazon and the website is All the content is free.

Jason Mezrahi: 23:27 You have people who’ve been in the industry for, like I said, Scot’s been in the industry for 20, 25 years. Other DFS pros, everything’s free. We’re publishing four or five articles a day, podcasts every day. Free access to a meteorologist on site, which is allowing you to see where the weather is at. So you don’t have to go searching for weather as well. So, everything’s there. The access is there and we’re going to consistently add more tools to the website and check it out.

Ryan Knuppel: 23:55 Well, so cool. So cool man. Thank you so much for joining me listeners. I appreciate you tuning in here and listening to what Jason has to say. Great guy, great book. I’ve already read through it. I got mine here. You’ll see me holding the picture if you’re watching this podcast, but awesome stuff, man. Keep up the good work and I can’t wait to connect again. So I appreciate you being here.

Jason Mezrahi: 24:14 Thanks for having me, Ryan. I really appreciate the time. You’re a great guy, doing great things and I’m excited to work with you in the future.

Ryan Knuppel: 24:21 Awesome. All right everybody, have a great night and thank you, Jason.

Ryan Knuppel: 24:24 Thanks for listening to this episode of the Knup Sports Show. If you enjoyed this podcast, please consider subscribing to our iTunes channel today. Plus visit us at for more pics, previews, strategy, and news. That’s K-N-U-P


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Ryan is a veteran to the sports betting industry. He owns and operates Knup Solutions where they provide the highest quality sports betting and igaming content to affiliates and operators. His contributions on Knup Sports show his pure knowledge and love for the sports and gaming industry.

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