It was 10 years ago that Adam, Tareq and I came together to start SidePrize, the fantasy sports company that most know today as PrizePicks.
It seems like just yesterday that the six of us moved into the tiny 3-bedroom house in Marina del Rey. It was the hottest summer on record and the house had no air conditioning. Amazing that was a decade ago.
Recently, Adam invited Tareq and I to get on stage with him at PrizePick’s Summer All Pack—a week-long onsite for employees. We talked about the early days of PrizePicks—back when it was known as SidePrize.
PrizePicks might seem like an overnight success, but it has taken 10 years to get to this point. Along the way, there were several close calls where the business almost didn’t make it. Jay and Adam have done an amazing job weathering those storms.
The event was great—I loved revisiting those old times on stage. Plus, it was fantastic to see Adam, Tareq, and our early investors like Michael Cohn again.
In the days before we got on stage, I went through my old SidePrize files—designs, photos, sketches and other documents. I had a few calls with Adam and Tareq—that brought up several old memories.
You know, starting a business is all-consuming. SizePrize became a significant part of who I was for a long time. That’s often what it takes to even have a chance at success.
That flood of old memories—getting on stage and telling our story—it made me realize that I should write some of this down.
So here it is, what I remember about the early days of PrizePicks.
Fall 2014: Mobile, AL
In early 2013, I took a job at Red Square, an advertising agency in Mobile, AL. Our clientele varied, but we had an increasing number of gaming and casino clients.
I worked as the digital producer for those customers. Casinos can be challenging. They prefer things fast and cheap, which leaves little room for quality. Even with those constraints, we managed to create many cool websites and even a few games.
Here’s one we built for Hard Rock Tulsa—If you watch the commercial closely, you might even spot a handsome guy you know.
Shout-out to my friend Kevin Zengel who published this video. If you’re in need of a sharp Creative Director, he’s your guy.
There’s something about working in an agency. You get a project to a certain point, then hand it over to the client. And, usually, that’s the end of it. There are no opportunities for improvement because the client doesn’t want to pay. In the agency world you create things and then let them go.
That never sat well with me.
After two years of agency work, I decided it was time for a change. I was done with agencies and was trying to figure out what was next.
Reflecting on it now, I pushed myself extremely hard the years I spent in Mobile.
I’m already a pretty intense person, but I recognized that I didn’t want to live in that town forever. And that sentiment nudged me into doing things like publishing interviews.
I had started an online publication called Signal Tower. I’d record conversations I was having with designers, and entrepreneurs then publish them. It was mostly an excuse to have conversations with people I thought were interesting or working on interesting things.
In July 2013, I recorded an interview with a guy named Adam Wexler, who later I’d start SidePrize with.
At the time he was the founder and CEO of Insightpool, a social analytics company. Adam came highly recommended from Jon Birdsong, a friend in the Atlanta tech community.
Anyways, when trying to think of people I could reach out to for leads, I decided to send Adam an email.
I didn’t necessarily think he was looking to hire, but I figured he probably knew someone in Atlanta with an early stage company who did.
Hey Adam,
I’m planning to leave the ad agency and come back to Atlanta sometime in the near future. Curious if you knew of a company looking for a UI Designer or Product Manager? If the company team is small, I could also do frontend.
Any leads would be appreciated!
All the best,
Sam
And then 15 minutes later I get this one line response from Adam.
you a fantasy football guy?
Adam and a guy named Tareq Dowla had started working a league management tool for fantasy football called Virtual Commissioner.
They were looking to build a tool to help people facilitate side bets. In many of the Virtual Commissioner leagues that was happening.
Could we build a product around it though? They needed someone with a design background to help paint that vision. Adam was calling the concept SidePrize.
I was hyped about the idea. I love football—I love fantasy football. It seemed like there was a ton of potential. Coming from the casino and gaming industry, it was obvious to me that the market was ready for something like this.
Christmas 2014: The Pink Startup
Adam and Tareq were headed to a fantasy sports conference early in the year and wanted a few screens to show people at the conference. Tareq had some rough user flows that were a great starting point, but they were not something to get excited about.
I remember being at my parents’ during Christmas that year. I spent most of the week at the kitchen table building an interactive prototype that Adam and Tareq could show people on their phone.
The prototype was originally built in Invision, which no longer exists. However, I was able to pull the screens into Figma and recreate the experience. I showed off this short clip during our talk at the PrizePicks offsite.
When I showed Adam and Tareq an early iteration of my work, they were skeptical about the brand. I had chosen pink as the brand color. Neither of them could get past it.
I showed them the website Tareq designed. Then we looked at several other sites in the space—they looked identical. Every product was dark gray with green or gold accents. They all used these tacky mockups of money or bags with dollar signs.
Every brand looked the same.
Pink was not just a little different, it was strikingly different, and people would notice. Years ago I wrote about that decision in a post called The Pink Startup.
I could have chosen red, or orange or blue, and there would have been no questions. But the color I chose was pink.
There’s no hidden meaning. I chose pink, because it was different.
That’s it.
Pink stands out in stark contrast to the sea of gray backgrounds and green accents of other fantasy products. It’s an easy way to differentiate ourselves, and that’s good enough for me.
Adam and Tareq reluctantly agreed to move forward with the brand and prototype I had built. They’d show conference attendees and get their feedback.
It was an enormous hit.
Both the product and brand were compelling. It went a long way in validating where we were going. From that point forward, I got a lot less pushback on my design choices.
March 2015: Take a Leap
It looked like we were onto something.
We hired Dan Cunning, a talented software engineer, to help build the MVP of this thing. The two of us started building the first version of SidePrize early in 2015. Our goal was to get a product ready for fantasy baseball in the spring. If we could do that, we would be able to work out several issues before football season.
We probably should have built a native app. I had no experience developing android or iOS apps though. So we went with mobile-first web.
In March 2015, I took the leap. I left my job at the agency and moved back to Atlanta to work on SidePrize full-time. We had no revenue, so the pressure was on to build a working product and raise money.
At the time, I thought we were a few weeks away from getting our first seed check so we could pay ourselves something. That wasn’t the case, though. Several weeks went by, then a month, then another month. It was discouraging.
In retrospect, I was lucky. I was living extremely frugally—even before leaving my job. Mobile has a very low cost of living. I was well-paid and saving a ton.
It was rare when I bought things. Friends would come over and they couldn’t believe that I had no furniture. For years, my home desk was a cheap fold-out banquet table and a steel chair—just like our hacker den in Chicago.
My parents paid for college—an enormous advantage that meant I had no debt. All of those things put me in a position where I was able to work on SidePrize without needing to collect a paycheck.
Things were tough though. March turned to April, April turned to May. It wasn’t clear when or if things were going to get better.
In June 2015 I began considering if I needed to take on freelance work.
June 2015: Squatting in the ATV
Startups have to be scrappy. Adam, Tareq and I had spent a couple of months squatting, working in conference rooms in the Atlanta Tech Village.
Technically, we weren’t paying tenants yet. We had reserved one of YikYak’s office spaces and were waiting for them to move out. Luckily, they were slow, which gave us an alibi.
Things turned around quickly. We finally got to move into our own office. And a couple of weeks later, we received our first seed check from the Akers family. It was a huge relief.
Then a few checks followed—from Atlanta Hawks CEO Steve Koonin and Cloud Sherpas Co-founder Michael Cohn. We were finally able to start paying ourselves and could hire a full-time engineer or two.
The following week, we headed to the Summer 2015 Fantasy Sports Trade Association conference in New York. There, we won just about every award they had—the Elevator Pitch, Shark Tank, and Hackathon.
We came out of June with great momentum. Once again, it felt like we were on to something.
Not long after moving into our office we brought on a handful of interns.
Adam wanted to have them on the ground doing guerilla marketing. We had them go to places and handout cards with promo credits on them.
We’d send them to college football tailgates with pizzas. We only needed one person in each league to sign up. So a slice to onboard an entire league seemed like a bargain.
Also, it was about this time I tried to start an online fantasy sports community called Fantasy News. I had hoped it would be a way to introduce and onboard users to SidePrize. I built the application with Meteor and Telescope.
The community never really gained any traction though. Running a community takes a lot more investment than people realize. The idea was right, but I wasn’t really able to execute on it.
Since then PrizePicks has invested in community a ton and it’s paid off. The PrizePicks discord has almost half a million members.
July 2015: LA Dodgers
With additional seed money and recognition, we made our first full-time hires—Dan Kaplan, Brett Norris and Stephen Reid. The six of us would become the core SizePrize team.
In July, we had a decision to make. We had been accepted into the LA Dodgers R/GA sports accelerator. Adam was skeptical about whether or not we would need it. This was not his first business, and he was unsure if the program would be worth it.
We decided that it was the right move for the business. That summer, we packed up and moved to Los Angeles.
On our first day of the Accelerator, we had the opportunity to meet Magic Johnson, who is a part owner of the LA Dodgers. We even got the fantastic picture above with me in his armpit.
As I mentioned at the beginning of this post. The team rented a three-bedroom house in Marina del Rey. It was a nice neighborhood and not far from R/GA’s office, where we would work.
Living conditions were extremely tight though. All six of us were in that tiny house without air conditioning. Those first couple of weeks were especially tough. LA was experiencing a heatwave with some of the hottest temperatures on record.
With football season around the corner, we were racing to get ready. There was a huge amount of work to do.
September 2015: Disney Theme Parks
SidePrize, the product, worked by having players connect their fantasy sports leagues. We would pull weekly scores and settle any outstanding side challenges based on those scores. We only needed one player to connect a league.
With Yahoo!, it was pretty straightforward. Hit the API, get final scores, and settle the challenges.
On the other hand, ESPN Fantasy was just as popular as Yahoo!. We had been signing up ESPN Fantasy leagues for months. We had hundreds of ESPN fantasy football leagues signed up. However, we had a pretty large problem—we had no way to connect to those leagues.
ESPN had no API. And not only that, they worked hard to discourage non-human logins. We had no automated way to settle challenges. As the regular season crept closer, we became more and more nervous.
We had a backup plan, but it was going to involve us manually logging in and settling challenges after games ended. That would be fine for a handful of leagues, but it was going to take an enormous amount of time at our scale. I was worried it would kill the business before football season.
Then, about a week before the regular season, we had a breakthrough.
Someone (maybe Tareq or Stephen?) had the idea to see if we could log in through a different Disney property. Maybe they shared an authentication system? Disney theme parks was an older application—seemingly irrelevant to anything sports-related. For whatever reason, it did share authentication with ESPN Fantasy. You could log in to your Disney theme parks login to get to ESPN and vice versa. This trick gave us an automated way to settle scores.
It was an enormous win for us.
Now, I’d like to pause for a second. I recognize that this isn’t a great way to build software. But when you’re trying to prove a concept and are up against the clock, you have to push the limits sometimes. That’s where we were 10 years ago.
And man, it was such a relief not to have to manually go through hundreds of leagues and settle scores.
We also made a few fantastic brand and UI updates based on input from R/GA’s designers. I’ll always love the suggested headline for our website—This week you win 9 games, not 1.
October 2015: The Daily Fantasy Rollercoaster
DraftKings, Fanduel—by October 2015 everyone knew who they were. Both companies were setting records by spending hundreds of millions on advertising—outrageous amounts of money.
They were buying so much ad space that it was inflating advertising costs for other businesses. For better and worse, they attracted a huge amount of interest in fantasy sports.
It looked like we were positioned to benefit from these daily fantasy companies. Investors saw the growth rate of these businesses and were looking at other operators in the space—like SidePrize.
However, there were signs of trouble. A DraftKings employee won a few hundred thousand in contests using internal, non-public data. They could see what players were being picked up and at what prices. This gave them an edge in selecting high-value players.
Over the course of the month, a few other stories broke about employees winning contests. The controls and policies were either not in place or not being enforced. In either case, it was concerning to those of us in the industry.
November 10, 2015: Demo Day
The LA Dodgers had organized a demo day for the startups in its accelerator. The founders would get on stage at Dodger Stadium and pitch to investors and media.
Adam was all set to go on stage at 7:00 pm. I had worked with an R/GA designer to build the SidePrize pitch deck.
I felt good about where we were. Our plan was to come out of the accelerator and raise a Series A. Despite the recent negative stories about DFS, we were confident.
That all changed quickly.
That afternoon, a few hours before Adam was set to pitch SidePrize, the state of New York outlawed all fantasy sports.
A few moments after I found out—I was still processing—I got a text message from my Aunt. The text message said, “Is this bad?” and included a link to a New York Times article—fantasy sports banned in New York.
That’s the moment I knew we were screwed.
My aunt is great, but she didn’t really understand SidePrize. She doesn’t care about fantasy sports. If she was able to draw that connection, certainly investors would.
The timing could not have been worse. To this day, it is still amazing how perfectly, comically terrible it was. If there’s ever a movie about PrizePicks, it will seem like this moment is exaggerated—but that is exactly how it happened.
Thanksgiving 2015: The End of the Beginning
Unsurprisingly, investors did not miss the news. We took only one investor on after demo day. It was also the smallest investment we received.
As the regular season winded down we continued to settle games for our users (not in New York). It wasn’t clear what was going to happen next though. I didn’t really know what we were going to do with the product.
The month following Demo day is a blur. I’m having a difficult time remembering exactly what happened. I was extremely disappointed, probably a little depressed.
We decided to stop taking our salaries again and let had to let the engineers go. It really sucked. We had become friends and had a blast woking together. Fortunately, engineers were in demand and they all landed in good places.
We had the house for a few more weeks. I stayed in LA through Thanksgiving. I think I was too embarrassed to go home. I knew there would be a lot of questions and I didn’t have any answers.
It was a weird time.
December 2015: Trustfuel
Back in Atlanta, I didn’t know what to do with myself. I was pouring everything into SidePrize. I had high expectations for the business a month earlier, but the reality was different.
I saw the best case scenario as a years-long legal battle. Uncertainty was going to be part of the fantasy sports business for a while.
After a year of taking little or no paycheck I needed a job. Adam suggested that I reach out to Trustfuel’s founder, David Klanac, and see if he needed any design or frontend contract work.
I liked David. He sublet space from us when SidePrize was in the Atlanta Tech Village. At the time he was building a Net Promoter Score survey tool.
Fortunately, David did want help.
Looking back on it—I think it gave me something to focus on. I’m not good at sitting still. Laying around, being depressed about SidePrize was not good for my mental health.
April 2016: Leaving SidePrize
Even though I was spending most of my time working with David on Trustfuel, I was still trying to figure out if there was another business opportunity for SidePrize.
I designed a few more concepts for SidePrize—an eSports product and side challenges for golf. We discussed building software for bowling alleys, but I wasn’t sure where to begin with that. Nothing sparked the same level of enthusiasm.
I held onto hope that there would be movement on the legal front. Could we return to the game we had designed? Could we create something similar? Unfortunately, there was no change.
On the other hand, it felt like things were moving quickly for Trustfuel. Customers didn’t really care about the NPS tool we had built, but we identified a potential opportunity to productize customer success workflows. I built a prototype to test the waters, and the response was overwhelmingly positive.
We quickly changed direction and began developing a workflow tool. Once again I was doing both design and development work. I had never worked on a SaaS tool before. It was challenging and had interesting problems. I was loving it.
If you’re interested, I’ve got some of my work from that period tagged Trustfuel on this site.
Anyways, things were going well. And in April, David offered me a full-time job at Trustfuel.
I told Adam and Tareq that I would still be available if they needed me, but I planned to accept David’s offer and work on Trustfuel full-time.
And that’s where my story ends.
Reflection
Since then, I’ve made a handful of contributions when either Adam or Jay has reached out. But the two of them absolutely deserve all the credit for the success of PrizePicks.
Looking back a decade, it is clear how great of an entrepreneur Adam is.
Adam is persistent. He never gives up, even when things look terrible. There were several catastrophic moments for the business over the last decade, but he pushed through all of them.
Adam is patient. This might seem like a contradiction, but he had long-enough vision to see where the fantasy sports world was heading. He waited and positioned himself and the business in the right place to capitalize when the moment was right. He found a fantastic partner, Jay, to help get the business there.
Last week, Adam announced that he is stepping down as CEO and handing the reins to former Blizzard President Mike Ybarra.
It has been an unreal run. I am excited to see what is next for both Adam and PrizePicks.
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