Tennis with a Frying Pan (Feat. Adam Levitan)

It’s no secret I like prop bets with friends—usually as a useful motivational tool, but sometimes as a good spot to make money, or even just for fun (since going through life without risking your hard-earned money on how much McDonald’s someone can eat in 36 hours isn’t a life I want to live).

Some recent prop bets:

Workout Props with CSURAM88 and Adam Levitan – Motivation to work out

Donald Trump to Win Election – Make money

Length of Best Man Speech – Fun

Employee Talks in British Accent – Awful freeroll

Joe Ingram Book Prop – Motivate a friend to write a book

BTW, I’m going to make some new workout prop bets soon since I’ve spent the last month traveling, drinking, and eating 12 meals a day, so get at me if you want to book something.


Frying Pan Tennis

The newest prop bet within my circle of degenerate friends is maybe my favorite. Sometime this weekend, Adam Levitan will be playing a tennis match against former tennis pro Stephen Bass. Bass played at Notre Dame and recently won some other high-stakes tennis matches in which he had to win every game. He’s a good friend of Peter’s and was part of his bachelor party at the Playboy Mansion.

The tennis match is straight up at even money, except Bass needs to play with a frying pan. This bet has been done before, but we came up with the idea to replicate it in Miami after Bass had just beaten a really good tennis player 6-0, 6-0 (multiple times). I asked Peter if he thought Bass could beat a normal “good” player with a frying pan. Believe it or not, most of the gamblers we talked to initially like Bass in this situation.

Here are the official rules:

  • Bass can select two frying pans, but cannot hit a tennis ball with either one until the day of the match.
  • He gets a normal warmup period and can select which frying pan he likes best.
  • Must be a standard frying pan

The bet will take place this weekend in Denver; I don’t know when, but I’m sure there will be a live stream of it. I honestly have no idea what will happen. Bass is an amazing athlete and won’t get tired, so it’s really just a matter of if he’s capable of hitting the ball with any sort of accuracy since it’s unlikely Levitan will be able to hit winners. Bass is also super sharp and will adjust appropriately to maximize his odds of winning.

On the flip side, the main thing Levitan has going in his favor is that his opponent will be playing with kitchenware.

That Time We Paid an Employee $500 to Talk in a British Accent

A few months ago, I recapped the FantasyLabs company trip and my workout prop bets with CSURAM88 and Levitan. The post was so long that I kind of glossed over something that didn’t get enough attention, which was that the three of us paid FantasyLabs Editor-in-Chief Matthew Freedman $500 to talk to his wife in an accent.

Here’s the recording he delivered:

40 Counterintuitive Tips for Building a Business

I have a little bio on the landing page of this site. Here’s part of it:

Who cares where I went to school or what’s on my resume? I also don’t want to reveal the fact that I’ve never had a real job, because that would make me look #inexperienced—unless you consider the following things I did to be jobs: tried to become a famous artist, sold a lot of stuff on eBay (including my soul, which I think I still have because eBay removed the listing), bought a whole bunch of glass after receiving horrible advice from my grandfather to “buy all the glass you can get your hands on, trust me,” became a magician, bought an acre of swampland in Louisiana for the investment potential, became a competitive eater (retired three hot dogs in), and started a few other businesses I’ve been advised by my lawyer to not even talk about. Talk about a fucking resume.

So if you’ve arrived at this post and you’re asking why I’m qualified to talk about building a business, there’s your answer. They say the greatest entrepreneurs are the ones who fail the most—idk who ‘they’ are or if anyone actually says that, but it seems like it could be true—and so I’m more qualified than anyone to talk about this stuff because almost everything I’ve ever done has been a colossal failure.

You don’t know business until you’re knocking on strangers’ doors at 5am to convince them to sell you their glass…or working on inventing new card tricks as a career move…or marketing yourself as a famous artist halfway through your first ever oil painting…or trying to sell a plot of land in a fucking swamp you’ve never visited.

Now that I’ve established ultimate credibility, you’re probably very interested in learning from me. “Look at his history of failure! He must be an amazing entrepreneur with all those fuck-ups,” you’re likely saying to yourself. Really though, I’ve learned so much over the years by messing up. Figuring out what not to do is sometimes the most valuable information you can gather.

I was initially going to title this post “Tips for Building a Business,” but as I jotted down some thoughts, I realized that pretty much everything I was writing was the opposite of how you’re “supposed” to do things. My typical day is evidence of that. Everyone is taught the same sort of stuff for how to “succeed” in life or make money or start a business, and for the most part, we just blindly accept it even though 1) the advice sucks ass and 2) there’s inherent value in doing things differently.

So my list of ways to succeed in business (even if you aren’t self-employed or an entrepreneur) is for the contrarians out there who don’t want to follow the rules.


Do stuff.

“Fuck, I gave this guy the benefit of the doubt after reading through that shitty intro and his first tip is to do stuff.”

Every time I see how most businesses operate, I’m dumbfounded by how much time is spent either working on meaningless stuff or not working at all. The truth is most people prioritize feeling like they’re accomplishing things over actually being productive.

When in doubt about how to proceed, do actual work related to improving the core part of your business. Stop with the phone calls and aesthetics of your logo and monitoring Twitter every 30 seconds. You’ll have the most success focusing on a few items you know will have a major positive impact.


Get distracted.

It’s okay to go off on a tangent.

In a recent FantasyLabs podcast, DFS player BeepImaJeep (Jay Raynor) talked about how he’s trying to find buried treasure in the Rockies. No really, he’s leaving this month to try to find this treasure.

Jay was the main subject of the Dan Barbarisi book on DFS—Dueling with Kings—and I recently saw Dan and we started talking about Jay’s quest for this treasure. Dan mentioned Jay will sometimes go down a rabbit hole researching something, and many times it ends up being fruitless and feels like wasted effort. But sometimes it’s not, and Jay’s tendency to get “distracted” in the right way is why I think the kid is going to find $2 million dollars of buried treasure.

You’re going to have ordinary results if you have a conventional process. Give yourself freedom to be creative, even if it doesn’t always lead to short-term results.

No one ever found treasure in the middle of a popular trail; it’s hidden in the areas yet to be explored.


Don’t plan much.

It’s good to have a vision, but excessive planning ends up being inefficient because 1) things change and you need to adapt, and 2) you want to be nimble with no unnecessary hurdles that could jeopardize your ability to switch course.



You’re going to have lots of bad ideas. Most of your ideas are probably awful. Mine are. Give up on them. Don’t see them through. It’s a waste. For the most part, when an idea is a winner, you know it pretty quickly. Whether it’s a single feature of your business or the entire concept, if it isn’t working early, you shouldn’t actually stick with it unless there are additional signs it will improve.

They say you should quit while you’re ahead, but you should also quit while you’re down only a little (money, time, energy). Quitters win.


Collect emails before making money.

If you’re starting a business and unsure of where to start, spend time finding creative ways to get emails from your target audience. There’s everlasting value in those emails as a primary avenue of communication with potential customers.


Don’t save money.

You should save money until you have some safety—whether it’s operating capital for a business or just cash in the bank personally. After that, saving money is for suckers, in my opinion. No one gets rich by saving money; they get rich by making more money. I think that’s really, really important, so I’m going to repeat it: if you want to get rich, figure out ways to make a lot more money. Seems obvious, right? Invest in yourself and your business and don’t hoard money unless it’s part of a long-term play to make more money.


Don’t work on cultivating your “brand.”

Just be yourself and if people like and connect with it, that’s great.


Don’t be a good boss.

Don’t be a boss at all. Be a leader. The best leadership comes when people don’t even know they’re being led.


Don’t always compete.

I hate to lose. Hate it. Any success I’ve had stems from wanting to crush anyone who thinks they can do something better than me to the point that they’re demoralized and give up.

But you have to know when it’s smart to compete. If you focus too much on winning, it’s easy to forget that what you should really be doing is making new rules for how the game should be played.


Don’t listen to customers.

Just kidding. Sort of.

You should listen to your customers at times when it comes to small features. If an aspect of your product/service is “off,” they can tell you that.

But, there are other good reasons to not listen to customers (and, generally speaking, I think you should ignore them more than you listen).

One reason is because the types of customers who speak up generally aren’t representative of all customers. At FantasyLabs, a disproportionate amount of our support is provided to free users. Some of them pay us nothing, have no intention of ever paying us a dime, and bitch about literally everything they could possibly bitch about. It’s bananas. At the other end, you have super hardcore users who might want very advanced features that could be cool, but won’t really help the business.

Another reason is because most people don’t actually know what they want or need. If we listened to customers, we never would have built Player Models, which was a totally unique concept. You can and should adjust minor things you’re doing based on customer feedback, but don’t just build out everything customers say they want because they’ll typically just give you minor variations of things that already exist.


Take lots of risks.

Don’t take risks for the sake of it, but generally, most value comes when you’re not afraid to take on risks others are avoiding.

SUCCESS Magazine did a story on risk with a really, really, really ridiculously good-looking male model as the subject.


Don’t optimize your day.

You should be striving to be as efficient as possible, but who says it needs to be done over the course of 24 hours? If you’re trying to help your business as much as possible in any particular day, you couldn’t do anything that provides long-term benefits.

I wrote about this concept in my post on working for free:

The merits of working for free change based on your timeline. I’m a big believer in the long game. I think most people optimize for right now and it’s +EV simply to make decisions based on what’s most beneficial down the line.

Simple examples: reading, sleeping well, and working out. All stupid uses of time if your goal is to optimize your day, but all some of the most vital aspects of creating long-term happiness/wealth/well-being. If the question is “How can I extract maximum value out today?” you probably shouldn’t work out, for example. It sucks ass. I’ve tried it. Not fun. But if the question is “How can I create the most value for myself (happiness, money, however you want to define ‘value’) in, say, 2019, then you should probably create a long-term foundation for success, with reading, working out, and getting rest being among the most +EV things you could possibly do.

In many ways, this is what we’re trying to do at FantasyLabs. Not just in creating long-term customers by providing a foundation for solutions instead of one-off “answers,” but also in terms of the basic philosophy and structure of the company (which uses a “freemium” model).

At FantasyLabs, we give so much away for free. Almost all content is free. Most of the tools are free. I love free. Are we maximizing revenue right now? No. Our subscription is quite underpriced (in my opinion), even though it’s among the highest in DFS. We don’t try to squeeze money out of people to artificially inflate monthly revenue. We’d rather give away too much for free than too little because “too much” really doesn’t exist if you have “the longest view in the room,” as Sam Hinkie said.

Fundamentally, I think we’re all trying to strike a balance between maximizing money/value/happiness right now versus creating a sustainable foundation for long-term value generation. At one end, working for free makes no sense. At the other, you should work for free all the time because it provides value to the maximum number of people.

The optimal balance, then, is completely dependent on time—for when you’re trying to optimize.

Think about how to build the best possible business in five years. Do things that will lead to that result.


Work for free.

Speaking of working for free…here’s the full post.


Think about how you’re supposed to do things…and then say “fuck that.”

It’s okay to act in a conventional way at times. Sometimes it’s faster and, especially in non-competitive situations, there’s no downside to doing things like others do them.

But in the same way you shouldn’t be contrarian for the sake of it, you shouldn’t follow all the rules for the sake of it, either. And if you’re not sure which direction is right, chances are it’s the one others don’t pursue because it makes them uncomfortable.


Don’t start a business in the real world.

I’m biased, but I prefer online businesses as opposed to those out there in the “real world.” First, it’s scary out there. You have to leave the house. You have to talk to people. No thanks. Second, you can track everything online. And third, it’s easier to scale, say, an online boutique as compared to a physical one.


Bet on yourself.

I like prop bets like these. Anything that gives you an incentive (with personal downside) to accomplish your goals.


Don’t advertise.

Not advertising seems pretty extreme, but what I really mean is you should sell not by buying traditional ads and being blatantly obvious you’re advertising, but rather by genuinely helping people and becoming trustworthy within your space.

Don’t buy ad space on a website. Do a guest post.

Don’t purchase social ads. Become a valuable follow for your target audience.

Don’t advertise via someone else’s email list. Build your own by giving people things they want.

Don’t tell someone why they should give you money. Show them by writing a minimum of 19 books.

Show people how you can help them by actually doing it instead of just shouting it at them.


Skip meetings.

I mentioned this one earlier, but I think it’s really important. Meetings suck. They’re almost never worth the time. Communicate via email—where everything is tracked and can be viewed at any time—and hold meetings only when absolutely essential.

Related: FantasyLabs uses Slack and Sprintly for communication and project tracking.


Read and write.

Here’s a list of some books I like. Reading is time-consuming, but perhaps the most beneficial thing you can do long-term. When you read a great book, it can fundamentally change how you think about the world and solve problems.

Reading also leads to better writing, which I think is an undervalued asset for pretty much anyone who needs to communicate via email. Clear writing is a sign of clear thinking.

Side note: I was thinking about writing a book on how to communicate effectively via email to get whatever it is you want. Who’d buy it?


Don’t be second-best.

Being No. 2 is really bad because you’re in a really tough spot with pricing. I’m really interested in pricing psychology and there’s a ton of evidence that people really have no idea what most stuff is “worth”—it’s completely relative—and they mostly base their decision off of certain cues or anchors.

Well, if you’re second-best and the top company charges, say, $100 for whatever it is they’re selling, you can’t get too close to that price because customers will then have an apples-to-apples decision of which product/service to choose. If you’re No. 1, however, you set the going rate for what something “should” cost.

Plus, you should be building the best thing you can anyway and shouldn’t be satisfied being No. 2 just because who the hell wants that?


Charge more money.

I’ve learned this lesson through experience. It’s much easier to come down in price than it is to go up. Once you set the expectation of what something is worth, good luck trying to get people to pay more.


Don’t be balanced.

I’ve already written about balance and why I hate it.


Don’t multi-task.

Do one thing at a time and focus all of your attention on that one specific thing. Then take a break. Focus on something else and put all your energy into that. Take another break. Trying to solve multiple problems at once leads to solving none.


Don’t worry about competitors.

While you shouldn’t be naïve to real competition, don’t worry too much about what others are doing. If you’re focused on unique solutions and being as innovative as possible, it really won’t matter what anyone else is doing. FWIW, this is probably truer for small businesses than like McDonald’s or something. So if the CEO of Ford is reading this for pointers, I apologize for the poor advice, Mark.


Don’t work long hours.

Working 12-hour days is fine at times, but those who brag about working ridiculous hours are either not working very productively (most likely) or going to burn out. I’m a big believer in working intensely for shorter durations—“sprints”—and the timing of those should be fluid based on when you’re in a “flow state” of intense hyperfocus. Not only do I think this is best long-term, but I also think you only have so much energy to give over a specific period of time such that extended periods of truly efficient, productive work are impossible.

Show me someone working non-stop at peak efficiency for an entire day and I’ll show you someone on Adderall.

Also, take Adderall. (That’s a joke.)


Don’t read resumes.

Read the email they send and how (or if) they sell themselves in it.


Overcompensate employees.

In the same way optimizing for today leads to sub-par long-term results, underpaying employees is a poor long-term strategy. You’ll more than make your money back by ensuring employees are happy, feel fulfilled, have creative freedom, and have upside in the future.


Find complementary pieces.

There are certain things I do well, and other things at which I’m terrible. While I’ve naturally improved some of my weaknesses over the years, the smartest thing I did was find a business partner—CSURAM88—who complements my skill set and fills in the gaps. The areas in which I naturally struggle—verbal communication, networking, building relationships—are where Peter kills it. Similarly, the other founders at FantasyLabs are complementary to me and one another, and so my only objective is to just not terribly fuck up the whole dynamic.

You should certainly patch up your weaknesses so they aren’t huge leaks, but sometimes the best way to do that is with the right teammate so you can focus on making your strengths that much better. Again, trying to manufacture personal balance when it isn’t there typically won’t help you as much as being the absolute best in a couple areas and working hard to intensify and market those strengths. I don’t care what it is; if you’re the best in the world at it, you can make money and be successful.


Be selfish.

Be selfish, but as a means of helping others. You aren’t going to be a good leader, friend, relative, or whatever if you’re unhappy and unfulfilled.


Say no.

If you’re unsure of whether or not you should do something, don’t do it. Take only the most obvious offers—the no-brainer deals.

The exception to this is if you’re not in a position of power or have no leverage. If you have no credibility or you’re just starting in a particular niche, you should say yes a whole lot more often. At one time, I was writing for like 15 sites because I just said yes to anyone that offered me anything. That was bad for short-term income (I accepted any deal anyone offered…literally anything…they could have offered two bags of shit sent to my doorstep once a week and I would have politely asked for one bag of shit…or no now wait, three bags of shit? I don’t know which is better. Jesus this is going to be a long sentence.) and mental health, but a net positive for gaining credibility and setting a foundation for the future.


Don’t worry about money…kind of.

Money is good. I like money. You like money. Everyone likes money. I think I saw a study that money makes you happier up until a point (which was a fairly low annual income). I kind of buy that, but I also believe there’s probably a selection bias with the types of people who generally make a lot of money. Maybe they naturally aren’t happy. Maybe they pursue money for the wrong reasons and will thus never be happy no matter how much they have.

So I do think money makes you happier, but if your goal is to make a lot of money for the sake of it, it will probably be pretty hard to be content. If you want to make a lot of money as a vehicle for being free and doing more things that make you happy—traveling, entertainment, eating out, whatever you like—I think you’ll find more sustainability and fulfillment.


Get really lucky.

Most people you regard as “successful” probably got pretty lucky to be in their specific situation. Almost everyone I know who is crushing in business has a story of “if I didn’t meet this person…” or “this random choice was my big break.”

Usually, though, they got “lucky” to be in their particular role because they put themselves in a position in which they could get lucky in the first place. In daily fantasy sports, the best players always seem to get the luckiest because they’re consistently putting themselves in spots to benefit from randomness. The same is true in most pro sports drafts, with sharp teams generally acquiring more picks and giving themselves more ways to get lucky.

And so the easiest way to get lucky is to take a lot of shots. If something is failing, give up quickly and do something else. You only need to hit one time.


Ignore advice from almost everyone.

Do your own thing and figure it out on your own. Don’t pass up advice from obviously high-quality sources of knowledge—it’s not like I’m ignoring Mark Cuban’s emails—but the majority of people aren’t going to know better than you how to control your business or life. If you make a mistake, who fucking cares? Just learn from it and move on to the next thing.


Don’t raise money.

Yes, FantasyLabs raised money from Cuban, but we didn’t necessarily “need” it and the move was all about the strategic partnership; there is no better investor we could ever have.

Otherwise, don’t take money until it’s absolutely essential. There are obvious companies that need money to scale—DraftKings, Uber, etc.—but, especially early, you should be trying to hold onto as much equity as possible by doing everything you can possibly do on your own.

Also, there’s value in having total control and not needing to answer to anyone. If you want money to be free and raising money could lead to feeling caged in or creatively restricted, then what’s the point?


Write a book, but don’t worry about sales.

Books are the most effective marketing tool I know of.


Don’t take your time.

Entrepreneurs can’t be perfectionists. Work quickly, test things, and put more resources into the things that work. You never want to work so much on something that you hit the point of diminishing returns with a losing idea. Take your time only when you know you or your company will benefit in accordance with your level of attention to the details.


Don’t always do what you love.

Sometimes, it’s okay to keep a hobby a hobby. Not everything is meant to be turned into a business and it’s pretty easy to lose your passion for something when your income is tied to it. I forget where I saw it but I recently read a quote that you should do one thing in your life that makes you money, one thing about which you’re very passionate, and one thing that keeps you healthy. If your goal of making money is to live a free life so you can do what makes you happy, don’t sacrifice the things you do that already give you that happiness.


Don’t talk about being an entrepreneur.

Unless you’re writing a blog post about it.


Build a business that doesn’t need you.

From the start, build a company that would operate just fine (or suffer as minimally as possible) if you were to disappear.


Don’t give a shit.

Perception is very much based upon expectations. One of the worst feelings as a DFS player is having massive equity in a tournament and then falling because you feel like you “lost” money. You could have a 10% ROI that feels like a huge win or a huge loss depending on your expectation.

If you lose those expectations, you become free. You can take more chances. Spend money more aggressively when needed. Hold more leverage in negotiations.

There’s a Taoist story about an archer who can hit a bullseye with every shot in practice, but crumbles under the pressure of competition. If you want to hit a bullseye, or get the job, or start a successful business, free yourself of expectations by negating the influence of external factors.

The guy who gets the girl is the one who doesn’t care if he gets her or not.

Final Results from My Workout Prop Bets (Plus A Look at the FantasyLabs Company Trip)

Near the beginning of the year, I booked some workout prop bets with Peter Jennings and Adam Levitan. The reasoning was simple: to give us motivation to get in better shape. When your daily commute is from your bed to the living room – and many times not even that far – it makes sense to work toward the goal of not having a heart attack by age 35.

We didn’t have much time to get prepared for this – about six weeks – but decided to compete this past weekend since we’d all be in Florida for the annual FantasyLabs company trip. And what a trip it was. We went to Orlando. Why Orlando? Because apparently you can book mansions there for the same price as renting a studio in Manhattan.


We were initially planning a trip to Miami, but once you factor in the size of our team (16 people went to Florida) and the cost of hotels/houses, it was obvious this was actually one of the cheapest options available. Yeah, one of the cheapest options we could find had a movie theater, bowling alley, lazy river, and at least two kitchens I never even saw.


The House

I’m really big on working remotely – no commute, fewer costs, etc. – but it’s important to get the team together every so often, and this was a good place to do it.

Outside of the workout props, other highlights included:

  • Dunk contest


  • Beating Levitan in Ms. PacMan
  • Winning $4,300 in my first attempt at NASCAR DFS (definitely 100% skill, no luck whatsoever)
  • Meeting a few of our employees for the first time and hanging out with the wily vets
  • Peter justifying getting into the pet industry by claiming “Dogs is up 30%”
  • Convincing (bribing) Freedman to talk to his wife with an accent for a full 10 minutes

The last one was an idea I had while at IHOP, which seemed like a natural place to go when you’re staying in a house with 20 pinball machines and an orange gym. On the flight home, I laid out the rules for the bet:


And Freedman delivered:


His name is matthew-freedman-6 on Venmo if you want to send your appreciation.


The Prop Bet Results

As far as the prop bets, the idea was a huge success. Even if I had lost every bet and a decent amount of money, it still would have been worth it. Both the money and the competition aspect of it were extremely motivating; all of us exercised very consistently – nearly every day – and worked harder than we ever would have without the bets. I didn’t want to lose money, but I really didn’t want to lose to Levitan and Peter. I can’t recommend enough how much of a proponent I am of using prop bets for motivation by giving yourself personal downside if you don’t work toward whatever goals you have and upside if you achieve them. Even since returning, I don’t have motivation to work out and won’t really push myself to do it until I create another challenge.

Mile run: Levitan winner (6:22), Bales 2nd (6:28)


The fact that over 11,000 people watched that is both awesome and disturbing. If you told me I’d run 6:28 in the mile, I’d be broke right now because I would have bet every dollar I own on winning that race. Amazing job from Levitan. If it weren’t on Periscope, I would have just stopped a little over halfway through because I could tell it was over, but I didn’t want to disappoint all the fans who tuned in to see a nail-biter.

Pullups: Bales winner (25 reps), Levitan/Peter 2nd (6 reps)

I had to go first in this event, which required the pullups to be from a complete hanging position and then all the way up with the chin above the bar. If you’ve ever done pullups, you might know the difference between a total lock-out and going 90% of the way down is substantial. I did only 15 (nearly 16) in training for this, so these results are what you’d call being a gamer. I actually didn’t know I’d win before the event, but I did know I was a lock once I got to about 15 and still felt pretty good.

Jumps (over bench, most in 2 minutes): Bales winner (95), Levitan 2nd (76)

Levitan went first in this, which was a big advantage for me. I tried to push myself at the end so we could get a realistic idea of the spread if we were to bet on it again. This exercise is sooo much harder than you might think. We had to jump off of two feet over the bench without touching it.

Bench Press: Peter winner (11 reps), Levitan 2nd (9 reps)

I was not able to compete in this because on the 10th day of training I partially tore my biceps tendon. I did 10 reps of 225 on the set before that injury. I actually couldn’t do pullups for a couple weeks, but I still trained for that by just holding myself up on the bar (from the highest possible position) and doing partial bent-over rows and other similar exercises.

Racquetball: Five stitches for Peter; Levitan and Bales big winners

I ended up winning two of my three events and would have been a mortal lock in the bench press.


My Strategy


Going in, my initial strategy was actually to lose weight. The reason for that is because lighter weight (assuming the same strength) would benefit me in everything except the bench press. Of all the events, I thought the bench press was going to be the most likely win for me and it really didn’t matter too much what I did there. Thus, if I could gain strength and lose, say, five pounds, it would help me in every other exercise.

Like I said, I tore my biceps tendon on the 10th day of the competition and had to drop out of the bench press. I was extremely incentivized to drop some weight at that point, so naturally I checked in around two pounds heavier than where I started. I think it just ended up being hard to not gain muscle from lifting weights for the first time in awhile, and I wasn’t going to force it.

The plan was to do all strength workouts until the Tuesday before the trip and all cardiovascular items up until Wednesday.



I thought I was a huge dog in this, which probably ended up being the case. On my first attempt at the mile, I had to stop. The first time I finished it in early January, it was somewhere around 9:30. That was outside and slightly up and down, but still – not good.

In terms of training, I ran a full mile only five times, I think. The way I trained for it was by instead doing sprints for as long as possible, stopping for a bit, then going again. Sprint. 30-second break. Sprint. 30-second break. And so on. The other thing I did was run up and down the stairs 50 times (up and down being one) as quickly as possible, which was my “light” training. My thinking was that I was probably so far behind that doing anything with moderate intensity wouldn’t be smart. I also wanted to improve my cardiovascular fitness more so than my muscular endurance, which was mostly fine, so I tried to really improve how long I could work at high intensity and still breathe properly.

Assuming I was an underdog heading into the race, my strategy was actually not to run as fast of a time as possible (which I was probably close to doing), but rather to get Levitan to run as slow of a mile as I could. I thought if I were near even in the final quarter-lap or so, I’d win.

To get him to run slower than he should, I figured I’d need to fuck up his pace. That was the reasoning behind firing out off the line; I wanted to get out to a lead and make him decide if he wanted to run at his pace or, preferably, try to keep up with me. He did the latter, which was good. I wanted him to think, “Oh shit, this is going to be more difficult than I thought,” and sort of freak out about how fast I was setting the pace. The first lap was around a five-minute pace – totally unsustainable.

Then my goal was to gradually slow down and hope that he’d do the same because of being more tired than he anticipated and just wanting a break. I really slowed down around the start of Lap 2. When he passed me, I died a little inside. I could tell by his form and breathing he was a huge favorite at this point. I was seriously struggling the second and third laps to keep pace. Since I set the pace so quickly, I had nothing left to give at the end. I tried sprinting full out for about three strides before my legs buckled; if I had kept going, I would have just fallen over.

Knowing his ability now, I should have let him set the pace. My only hope was to let him pick a pace that would be sustainable for me, too, and then blow by him at the end. However, without knowing he was capable of a 6:22, I actually think I did the right thing, sans perhaps going slightly too fast to start.

Nonetheless, dropping three minutes from my mile time in six weeks is a win. (Not really though since I lost the race, money, and pride.)



Like I said, I partially tore my biceps tendon (long head) while doing the bench press in training. That injury sounds really bad, but it didn’t really hurt too much and you don’t even fucking do anything for it; just ice and let it heal. The problem is you lose all strength in your shoulder, especially with any sort of pushing movement. Even shortly after the injury, I could still do certain things and had full range of motion, but I couldn’t do a pushup or hang all the way down on the pullup bar without pain, so I adapted the training to instead hold myself at the top for as long as possible. I also did bent-over rows and Superman extensions (idk what these are really called?). I could do full pullups again around two weeks before heading to Florida, so I went absolutely nuts training for this at that point. I mostly used an overhand grip because that’s what we did in the competition, but I occasionally worked in neutral and underhand (much easier).

With every exercise, I experimented with different approaches and tracked the results. With pullups, you can pull yourself up more with your mid-back (sort of leaning back), your arms, your delts, etc. I found the most success just going straight up and down, primarily because we had to put our chins above the bar, but also because that allowed for the best rhythm and no rocking. My rhythm during the actual event was perfect.

I started at nine pullups and had to beat Levitan by seven and Peter by six. No idea how I got 25. I tried it again this morning and got 17. This is another reason I’m really high on competition versus goal-setting as a means of improving. If I had faced a challenge of increasing my pullups from nine to 25 in six weeks, I would have assumed that’s not possible and I wouldn’t even do it. If it were just me competing against myself to reach 15 reps, let’s say, I also never would have been able to get to 25. Competing without knowing the status of the opponents was really the only way to push myself to a near-optimal level.



I made up this exercise, which I thought would be a really nice combination of leg strength and endurance. Go ahead and try to jump over a bench for two minutes straight. I got 51 in my first attempt.

I tested a lot of different styles with this: starting as fast as possible, pacing myself, double-jumps, jumping from different angles, taking five-second breaks at different intervals, etc.

I basically found that it didn’t really matter all that much what I did. Since I started not being able to jump for two straight minutes, I would always be around the high-50s no matter what I did.

Like the mile, though, my strategy was to start fast while training – not 100%, but close – and gradually extend how long I could maintain that high speed. That worked really well, and I jumped non-stop during the actual competition. Levitan came out FIRING with like 45 jumps in the first 45 seconds or something insane, but then he died. Every time he stopped for a few seconds, I got so happy. Not that I wasn’t rooting for my friend, but I wanted him to lose so bad and for it to crush him mentally and send him into a downward spiral so bad it’d take months or even years from which to recover. That’s a joke, but I definitely had to win this. I hadn’t beaten his 76 jumps at all while training, but my max was 74 while training, so I figured I could get there with everything on the line.

By the way, one thing that’s interesting is how little we actually push ourselves compared to what we can really do. I truly tried as hard as I could to do these jumps and couldn’t get more than 74, yet got 95 in Florida and maybe could have been above 100 if necessary. The difference in how my muscles felt was so extreme; after all three exercises, I felt like I had done an entire workout. It really reinforced the idea that if you want unbelievable results, you should create incentives you know will entice you to do things you’d otherwise be physically and mentally incapable of doing.


Bench Press

This was a lock. In hindsight, my only goal should have been “don’t get injured.” I was training with 235 pounds instead of 225. I was fully warmed up when the injury occurred, so I’m not really sure what I could do differently here. I do think there’s maybe some merit in using dumbbells over a barbell as it relates to injury prevention, but not for this competition.



Levitan and I joined a gym that has racquetball courts here in Philly, so we were able to play a bunch and will continue to do that in the future. I’d say the biggest improvements I made didn’t come in playing, but just in watching YouTube videos of guys like Rocky Carson (we have Rocky Carson racquets now, nbd). It really sped up the learning curve to figure out where pros serve, for example. Obviously that will change as I’m comfortable knowing where I should hit each shot.



Ate a Dunkin’ sausage, egg & cheese on a croissant the morning of the mile. Read: no change to diet.


New Labs Hats

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Should You Work for Free?

Back in college, I tracked every play in every Cowboys game and charted them into like 50 different categories: every motion, audible, pass length, formation, personnel, and so on. It took me like 10-15 hours to break down a game. I’d do it right when the game was available on Game Rewind, which was usually at like midnight.

Here’s a screenshot of a few plays:

Did I mention I’m a complete psychopath? Didn’t need to, didn’t need to, got it.

I had all this data that could theoretically be very useful to the team—and perhaps quite valuable for me—so I made the logical move and emailed the entire thing to everyone in the organization for free. I’m talking everyone: Garrett, Jerry, marketing interns, offensive tackle Marc Colombo, writers, social media managers, event coordinators, sales consultants, a homeless man who slept outside the stadium…everyone.

How did I get their emails? I figured out a way to get one of them through some completely normal and not at all creepy sleuthing, then could easily reverse engineer the rest of their email addresses using the same structure.

It’s called grinding, look it up.

Another brilliant idea I had at the time that my lawyer told me probably not to mention but I’m gonna anyway because yolo was a form of writing arbitrage. Basically, internet content was becoming king around that time and there were a bunch of sites that would pay freelance writers decent money to write short (and shit) articles. Remember eHow and About and those sites? Stuff like that.

They paid enough that I thought, “Man, this is too much money, I bet people would do it for less.” So they did do it for less, for me. I advertised my own company on Craigslist that paid writers very handsomely—and by that I mean about 50% of what I would be paid to write through another freelance publishing company at which they couldn’t be accepted—to create short articles, which I’d then publish under my name (with permission, of course…from the writers, not the company). $25 out, $50 in, and we’re off. That idea worked for a bit until the site contacted me wondering how I was writing 100 articles a day.

“I started drinking a new coffee,” I said. “And I’ve been experimenting with various writing styles, some very different than others.”

In hindsight, none of this stuff was a good idea. Nothing I did before about 2014 was a good idea. Don’t be like me.

Now listen to my advice on working for free.


Working for Free

I wanted to write this post a couple weeks ago when there was some Twitter debate about whether or not you should ever work for free, but I figured I’d just wait until everyone lost interest. Actually, I was just busy with some other stuff (including this sick DFS ownership dashboard at FantasyLabs), but I knew I wanted to chime in.

Darren Rovell initially started the conversation by tweeting that working for free is one of the best ways to get a job. “Fastest way to a job today is provide a team, a player, an agency, great work unsolicited and for free. It’s hard enough to get paid to work in sports. You have to prove value more than ever.”

A bunch of people had some pretty hot takes on the matter, ranging from “never do anything for free” to “spend hundreds of hours collecting data and then just give it away to the one potential buyer who needs it most.”

Matthew Berry, who I think has done a really phenomenal job of understanding the long game and the value of, well, providing value—he’s a fantasy sports analyst with nearly 1 million Twitter followers for fuck’s sake—commented on Rovell’s post:



I’ve gotten to know Matthew a bit over the past couple years, and one of the biggest things I’ve learned from him is to find success by helping people, not by trying to maximize short-term exposure. Just be authentic. A couple years ago—shortly after I first met him—we talked about fantasy football for an hour and he basically let me just ramble about my thoughts on uncertainty and projecting players probabilistically with a range of outcomes. Did he need to do that? I’m gonna go ahead and say no. He could probably charge someone lots of money to talk to him about fantasy football.

He has some really good career advice in this article, by the way, that’s relevant to this conversation and with which I agree almost across the board. In it, he talked about his path and working for free:

There are a ton of fantasy football websites out there. Offer to contribute to one of them for free. Just get your foot in the door. I know some people have started their own blogs and that’s certainly a way to go, but I prefer writing for someone else when starting out. Let someone else worry about traffic and the site and everything else. Just focus on honing your craft.

I prefer the personal blog route because I can say “for fuck’s sake” and be confident my editor—me—won’t remove it, but the idea is the same: develop skills—real, unique skills—demonstrate how you can help someone with those skills (however possible), then figure out how to make money from it.

This is sort of an aside, but in that same article, Matthew gave some other advice that really resonated with me:

Learn how to communicate in a variety of ways. I remember a famous agent once told me when I complained of writer’s block that, “Writers write. Period. Writers write.” You need to write and you need to hone your craft. The more you do it, the better you’ll be at it. You need to learn to be able to be comfortable in front of a microphone and a camera, be it radio, podcasting or video. When I was in Los Angeles, I took classes at the famous Groundlings Improv. Not to help my acting (there’s no help for that) but rather to get comfortable speaking and performing in front of an audience where I would have to think on my feet. The more platforms you are comfortable on, the better. Start a podcast. Do YouTube videos. You’re not worried about anybody watching or listening at this point, you just want reps.

Okay, I don’t agree with the whole thing. Improv classes? I get anxiety going to the grocery store. But the idea of communicating in different ways is something I really sucked at in the past and now I’m only moderately below-average. Really though, whether you work in media or not, your ideas are only as good as your ability to effectively communicate them. It’s on you, the communicator, to figure out the best way to do that with each specific audience. And they’re all different. Sometimes people say, “I only write for me.” Okay, then why is it online?

I’m rambling. Back to working for free…


Why Working for Free Can Be Smart

In typical I-need-to-finish-this-post-quickly fashion, I’m just going to sort of list some ideas/thoughts I have about free work and then hope by the end I can wrap it up in a way that makes you think it was all carefully planned.



Maybe the crux of the scattered argument I’m about to propose is that the merits of working for free change based on your timeline. I’m a big believer in the long game. I think most people optimize for right now and it’s +EV simply to make decisions based on what’s most beneficial down the line.

Simple examples: reading, sleeping well, and working out. All stupid uses of time if your goal is to optimize your day, but all some of the most vital aspects of creating long-term happiness/wealth/well-being. If the question is “How can I extract maximum value out today?” you probably shouldn’t work out, for example. It sucks ass. I’ve tried it. Not fun. But if the question is “How can I create the most value for myself (happiness, money, however you want to define ‘value’) in, say, 2019, then you should probably create a long-term foundation for success, with reading, working out, and getting rest being among the most +EV things you could possibly do.

In many ways, this is what we’re trying to do at FantasyLabs. Not just in creating long-term customers by providing a foundation for solutions instead of one-off “answers,” but also in terms of the basic philosophy and structure of the company (which uses a “freemium” model).

At FantasyLabs, we give so much away for free. Almost all content is free. Most of the tools are free. I love free. Are we maximizing revenue right now? No. Our subscription is quite underpriced (in my opinion), even though it’s among the highest in DFS. We don’t try to squeeze money out of people to artificially inflate monthly revenue. We’d rather give away too much for free than too little because “too much” really doesn’t exist if you have “the longest view in the room,” as Sam Hinkie said.

Fundamentally, I think we’re all trying to strike a balance between maximizing money/value/happiness right now versus creating a sustainable foundation for long-term value generation. At one end, working for free makes no sense. At the other, you should work for free all the time because it provides value to the maximum number of people.

The optimal balance, then, is completely dependent on time—for when you’re trying to optimize.


An Entrepreneur’s Mindset

Do you know who works for free all the time? Entrepreneurs. Do you know who never works for free and gets paid for every hour they put in? Employees.

Being an employee can be great. You can typically work only during set hours, get weekends off, don’t need to worry about problems that arise outside your expertise, etc. But, when you work for someone else, you (mathematically, at least in an efficient market) must take less money than you’re worth. And usually, you don’t get to participate in the upside if you (and your company) do an awesome job.

To be clear, I’m talking about the typical mindset (and pay) of your average employee/entrepreneur; you can be an employee with an entrepreneur’s mindset, or vice versa. Some business owners are total shmucks and would be better off working for someone else. But many people are sharp enough to absolutely crush it on their own and just aren’t going out and doing it. Today, and tomorrow, more than ever, it’s easy to go get it for yourself.

The big idea, I think, is getting paid on the value you create for others instead of getting paid for your time. Getting paid for your time can’t really scale, right? You can only work so much. It’s very linear—work X, get paid Y, work 2X, get paid 2Y. That stinks.

Maybe it looks something like this:


When you start to think about the value you can generate for yourself—again it can be happiness, freedom, money, whatever you want—I think you sort of start to realize that getting paid for your time is -EV if you have awesome skills and can better people’s lives.


The Right People

The upside of free work extends only insofar as it can increase long-term value in your life, so it should be obvious the person/company for whom you’re doing work is pretty important in determining whether or not you should work for free. If the industry leader in your field asked you to work for free for a week to prove yourself and there was a specific plan in place to acquire upside if things went well, that would be a no-brainer decision for you, right? If some guy from Craigslist asked you to write articles to be published under his name, maybe not as much.

FantasyLabs now has somewhere around 15 full-time employees and a handful of contractors/part-time workers. Exactly zero of them sent me a resume and were handed a job based on their qualifications. All of them proved their value in such a way that it became obvious we needed them; they gave us no choice.

Sean emailed us and did all kinds of amazing SEO/email/design work for free for like a month; he’s now our Marketing Director.

Ian worked for me personally for years collecting data, editing my books, and doing a variety of other tasks completely for free. I told him I was unable to pay him much, if anything, which was true, and he kept at it because he had confidence it would pay off; we hired him full-time before NFL.

Justin did projections at Basketball Monster and had thus built up a portfolio of work of which the DFS community was already aware. He was hired about a month after we launched.

Jay, Bryan, and Bill were three of our original admins who started with Labs almost right after the site launched; they were hired full-time within a couple months. Bill actually emailed me late in the process—the “process” being I told people on Twitter to email me if they wanted a job explaining why they’d be good for it—and we had actually already settled on using only three admins. Bill sent an incredible email (and sample article), both of which were logically sound and so well-written. Clear writing is a sign of clear thinking, so we brought Bill on too just because I thought he rocked. He’s so valuable to FantasyLabs now it’s insane.

Colin emailed me identifying an inefficiency in our product and offering a solution that would help us make more money and improve the value of our site immensely; he now runs PGA and is basically a Labs data scientist.

J.J. just sent over his signed contract yesterday to become a full-time Labs employee after absolutely crushing over the past few months, going above and beyond and never once asking for anything or complaining about the workload.

Even Peter, my co-founder and one of my best friends, helped me with my books for years—for free—because he liked the vision and maybe understands the long-term value of generosity more than anyone. The key is he’s just a genuinely nice person and not someone leveraging “kindness” for personal gain; it’s pretty easy to tell the difference.

I’m leaving people out, but the idea is that no one is going to just hand you something. Frankly, no one is really going to give you a chance out of the goodness of their hearts. I get lots of emails asking for work, and I’d say maybe 98-99% of them are some variation of “I love sports, I won my fantasy league two years in a row, hire me.” The others are almost always some form of “I think you could improve what you’re doing in these ways, here’s how and why it will benefit you, here’s why I’m in a position to help, and I’ll do it all for free.” Then they over-deliver on that promise.

My books are a form of the power of free work. I earn royalties from the books, but it’s not like I’m making life-changing money selling $9 e-books on a niche subject. The books are effectively marketing vehicles, though; they’re basically like sending the best email of all time to everyone in my industry (and interesting, sharp people outside it) demonstrating my expertise. I’ve had so many amazing opportunities stem from the books. Last week, I met the producer of one of my favorite TV shows because he read my books and began playing DFS. Is that going to help me down the road? Who fucking cares? It was cool. Even FantasyLabs was created through my books; the founder of SportsInsights was planning to start a site similar to Labs and contacted me after reading one of my books. That one single relationship led to the formation of an incredible company, which can be traced back to me at one time deciding to write a book (without knowing if I’d make any money) for the hell of it.

But it all comes back to providing value to the right people, meaning you’re the person who identifies them, and not vice versa. If someone asks you to do work for free, that might not be the best opportunity; your job is to spot the situation that’s going to improve your upside the most long-term—likely with someone who isn’t even necessarily looking for help—and then convince them you can improve their life by actually doing it.


Trading in the Sure Thing

In a nutshell, I think working for free is a form of gambling, but in a smart way. It’s +EV risk taking. It’s trading in the sure thing for a lower chance of short-term success—but disproportionate rewards when things go your way.

As an example, I could put hours into some very direct form of work—writing content for money, for example—and get paid for the work I complete. Or I could send, say, 100 emails to entrepreneurs, business owners, investors, whoever—emails geared specifically toward them and how each one might be able to improve what they’re doing—and 98 of them could go ignored, one of them looks promising but wastes my time, but that final one leads to life-changing happiness. Almost always, I think, the value is in thinking long-term and in taking risks—smart risks.

I actually think this idea the source of the “he got lucky” phenomenon. Mark Cuban got lucky to start and sell a company at the perfect time. Tom Brady got lucky to get drafted by the right team and get a chance to play because of an injury. SaahilSud—perhaps the best DFS player in the world—got lucky to finish ahead of everyone else in that DFS tournament. And that one. And that one.

This is true. All these people were lucky, but they also were bound to be successful no matter what. Making lots and lots of sharp bets—including betting on yourself by developing value-generating skills and leveraging them to help others, even for free—leads to short-term luck and long-term guaranteed success. Saahil is indeed “lucky” when he finishes 1st instead of 5th, but he exposes himself to so many opportunities to get “lucky” that it’s not really luck governing his success.

It’s not smart to take risks for the sake of it, but it is when everyone else’s risk-averse mindset means all the upside is in taking chances. If each of my emails or books or other “free” work takes as long to write as one article for which I could get paid $100—and they each have just a 10% chance of response—then anything above a $1,000 expectation from those responses would lead to more money. And that’s just right now. Two years from now, those articles pay you nothing. Meanwhile, those connections, my books, that free work are all paying dividends—exponentially increasing dividends. Look for the opportunities that pay off well into the future.

If you’re reading all this and saying “But I don’t have time to work for free,” yes you do. If you want something bad enough, you have time to do it. It’s always interesting to hear people say their dream is to do X, but almost always, they aren’t doing it. “I’m passionate about singing.” So why aren’t you singing? If you don’t have enough time (or opportunities, or contacts, or money), you probably aren’t really passionate about it. Passionate people don’t make excuses. They control their lives.

tl;dr The longer your view, the less concerned you should be with getting paid for your work and the more you should try to just help as many people as possible. Invest in yourself. Read books. Become an expert. Take chances.

And if none of that works, I have a cool little content business I’m starting if you’re interested in writing some articles for me.