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.