The Paths of Fantasy Businesses

Lots of people want to start a fantasy business. Because fantasy is fun, and making money doing something you enjoy is the dream for lots of people.

So, what do successful fantasy businesses do? I don’t have any inside information, but I’ve been trying to pay attention to the paths of other people. Especially those who have grown something that produces value that people are willing to pay for.

(I should warn you: I’ve probably mixed up some details here and there. Maybe I’m misjudging who is successful. But it has still been helpful for my own thought process to work through this.)

Fantasy businesses involve either fantasy content or fantasy products, or both. Think of every fantasy site in existence and you’ll see they all fit into one of those categories.

Most people start with one or the other, and perhaps expand to do both. So we can work through the choices one at a time.

Content First

The most common approach is to start out with producing content. Content is easy because every day you are given a whole new pile of games to write or talk about. Content is hard because everything you said yesterday becomes less useful today.

I think about this approach in four major phases.

Phase 1: Finding an audience

In the olden days, there were gatekeepers (USA Today, ESPN, etc.) and this path was only available to a chosen few. The rise of blogs gave everyone a chance to put out content. Later, podcasts gave a set of folks with different skills the chance to do the same.

Whatever the medium, you are adopting the role of Fantasy Analyst. Fantasy Expert? Sure, why not.

Most people drop off somewhere along the way. Their blog goes silent. This, in fact, happened to me on my first attempt a decade ago, and my blog is filled with “Sorry for being quiet on here lately” as I struggled to put out consistent content.

To prevent this tailing off, it helps to start your business with friends for accountability. That seems to have been a successful formula for RotoWire, Razzball, and others.

Anyways, a few people show the persistence to keep up the content production for multiple years. After a few years of hard work, you may find you have a following. An audience. And that opens up the doors to Phase 2.

Phase 2: Bringing in others

Once you have an audience, you’ll find that there are people in that audience who want to be like you. Some of them even want to write or talk like you.

If that’s the case, you can welcome them as part of your staff! Now you have a fraction of the content production duties you had before. Or, maybe you still expect yourself to produce the same amount of content, while also dealing with the stresses of managing a team. Whichever you choose, your business is growing.

Bringing in others always involves expanding to other sports. The overlap is irresistible.

Now, everyone knows that making money off of fantasy content is really hard. So your new staff members’ expectations for pay are probably pretty low. They know the alternative is starting on their own and going through Phase 1 making nothing, and something from you is better than nothing.

However, even if adding staff is cheap, it’s still not free. If ad revenue isn’t cutting it, you’re going to be looking at Phase 3.

Phrase 3: Closing the community

At some point along the way, a community ethos has formed.

It’s easy to spot the ethos for some popular sites:

The ethos of your community seems to be fairly static, shifting only with the aging of the community. Twenty years ago, BaseballHQ’s community probably looked like today’s PitcherList as the place where people were exploring cutting-edge stats. But today I would guess it’s identified partly by the features of its heyday: more rotisserie than points, more auction than draft. (I don’t really know, I’m just looking in from the outside.)

It’s somewhere around this point where a monthly subscription comes into play. The fantasy site subscription works like membership dues to a club or tithing at a religious institution. People aren’t so much paying for the content as for the sense of belonging. (And that’s just fine with me.)

Phrase 4: Building products

The final stage is building products. There is a chasm of skill here: Producing content and building products are skills without much overlap, and your media company has gotten really good at cranking out content.

And, sorry, a Draft Kit is not a product. It’s well-packaged content.

So not everyone makes this jump, and it’s probably not necessary. You can succeed with your unending stream of content.

But look at the product line that RotoWire offers:

And there’s probably more. But there’s a progression there from content-like products (rankings, projections, auction values) to pure products (league hosting).

Razzball is also a fascinating case study in using low-code technology to build impressive tools. I mean, as a developer, I’m rolling my eyes at their WordPress monstrosities and their Google Sheets. Instead of building real customization they just copy-pasted the same thing into 10, 12, and 15-team versions!

But it sure seems to be working. And their audience doesn't care the slightest.

Product First

I can think of a couple examples of people who have built a product and skipped the content grind. But there aren’t many.

The trick, it seems, is that you must link to some existing audience. If you’re not willing to lead a community yourself, you need to find someone who has that following.

Let’s run through some examples to illustrate this pattern:

The NFC - Greg Ambrosius had a following from writing for the gatekeepers in the early days. A friendly relationship with RotoWire (and SiriusXM) provides mutually-beneficial content.

Ottoneu - Connected with FanGraphs at the right time, which provided like-minded players and Ottoneu-specific content.

RotoLab - Starts from within the BaseballHQ community and incorporates BaseballHQ’s projections. It’s maybe a more modest success than the fantasy platforms, but it has accomplished that with almost zero promotion.

On the subject of modest successes, you can also see this with draft tools created by people on Reddit. The community is quick to promote those tools whenever a question about tools comes up.


What have we learned? Since I’m writing for my own clarity, I’m thinking of personal applications here.

I'm beginning to accept that I don’t have the demeanor for the content grind. I have trouble focusing for the entire season, let alone trying to do something year-round.

But I’m always drawn into the rhythms of draft season. Every year, after a little offseason (and sometimes late-season) break, I can’t help but to dive back in.

If I’m being honest, the product-first route is what suits me best.

And I need to acknowledge that that is a risky route, with few success stories. Or, perhaps, it just has fewer successes and fewer failures than the content-first approach?

Now, if I'm going to try the product-first route, I need to be thinking about existing audiences where my products and their content provide a win-win. Real synergy.

And when you start thinking in buzzwords like those, you realize that fantasy business is really no different from any other kind of business.

DraftKick is available now!

If you're still tracking your draft with a custom spreadsheet or even just pen and paper, you need to try DraftKick.

It is packed with features to help you succeed on draft day:

  • Projected availability
  • Keepers
  • Salary cap (auction) drafts
  • Custom league configuration
  • Editable projections
  • ...and more

It's completely free to try out!


I'm Mays. I've been playing fantasy since I was in high school (over two decades ago).

My speciality has always been player valuation—converting player stats into rankings and salary values. VBD for fantasy football? Rotisserie z-scores? We go way back. In 2009, I started Last Player Picked, a site that generated fantasy values customized for your league.

These days, I'm building DraftKick and Projectile, a fantasy baseball site with in-season projection visualizations.

You can find me on Twitter at @MaysCopeland or email me at