Chris Baus

Beyond the technical start-up, meet Chicago's king of the question

Although Dan Burns’s Whaddayaknow?, by Paul Graham’s definition, isn’t a high growth start-up, the company has carved out a niche hosting pub trivia nights at bars in the greater Chicago area. Whaddayaknow? isn’t battling it out for Series A funding, but not every company is destined to be the next Facebook. That’s ok. Success comes in many forms, and his customers don’t mind.

I met Dan on a recent trip to Chicago and was intrigued by his business and passion for it. The conversation proved to be a classic lesson in entrepreneurship. If you see a need, address it.

When trivia is your stock-in-trade, the hunt for the perfect question is never-ending — every conversation holds the potential of new ideas. As we talked, I was a surprised by how much pub trivia has in common with the capital-light, but knowledge-intensive, businesses I am most familiar with. Dan kindly agreed to answer a few of my questions about Whaddayaknow?.

If you have any questions of your own, Dan can be reached at:


Hi Dan, can you tell us a little bit about yourself, your business, and its scope?

I grew up just outside Boston, MA, went to school at Boston College, and lived in the city for several years after that, so I am a true Bostonian (go Bruins!). I worked in the Boston Public School system for several years before deciding a few years ago that I wanted to try switching it up since I had been in the city my whole life, and decided to come on out to Chicago as I thought it would be a good fit. It was tough leaving my friends and family, but I had the itch for a change of scenery.

I moved to Chicago in September of 2007 and began hosting my first couple of bars (Waterhouse Tavern and Cans Bar & Canteen) in October of that year. My company now hosts weekly trivia nights at 40 locations in the city and suburbs and continues to grow. We hold 2 major “Tournament of Champions” events each year (one in the winter and one in the summer), with our 5th one coming up next month in July. Each has been bigger than the last and we expect close to 100 teams for this next one, and are currently looking for a bigger venue in the city to be able to accommodate us. These events include all of the top teams from every one of our locations, who compete in a “Qualifying Round” to get an invitation. We give a ton of prizes away to the Top 20 teams including $1000 cash for the overall winner.

How did you get involved with pub trivia?

Pub Trivia has been big in Boston for many years now, and my friends and I used to attend every week at a local spot near us and loved it. It was a great weekly tradition for us; we always had a lot of fun. The host was a great guy who we got to know pretty well, and one night he asked me if I wanted to take over hosting at the venue, and I was happy to do it. To me, it was a great chance for a fun part time job as well as to get a little help paying the bills.

Did you move to Chicago specifically looking for business opportunities?

Not specifically for my own prospective business opportunities — I actually moved out here to get into sound engineering. Music is a huge passion of mine, and recording has been hobby of mine for a long time. Chicago is a great city for the field — better than Boston — so I wanted to see if I could get into it out here. I started the trivia business as a side thing to meet people and make some extra money, and once I realized its potential with its quick success, I decided to try to put more time into it and pursue if full time.

How did you go from having an idea, to actually pitching it to business owners?

When I saw the potential in Chicago, I was confident I could make it happen. Very few places were running a trivia night, and Chicago is really the perfect city for it — with endless bars and restaurants, and great neighborhoods that lend themselves perfectly to the concept. I literally walked into a handful of bars/restaurants that I thought would be a good fit for trivia, asked for the manager, and simply told them about the idea. I had seen it work in Boston and I was confident I could make it happen out here.

Was there a tipping point when you realized your business could sustain you financially or did you have to take a leap of faith to quit your day job?

It was a gradual process; I had an internship at a great recording studio that was unpaid for 6 months and only became a paying gig after that — and by that time I had seen the potential in the trivia business. Successful results from the trivia became apparent almost immediately. I was generating a great amount of weekly business for the bars on their off nights, and the managers were telling other people in the industry about my product, so I had a great chance to expand it.

Was there ever a time when you thought the trivia business wasn’t going to work out, and you’d have to go back to a straight job?

It’s funny. I never once for a second thought that it wouldn’t work. I just knew it would; it is something that plays to strengths and interests of mine, and I knew I’d be able to pull it off. The cliché of never underestimating the power of positive thinking is one that I believe is true.

When we met you talked a lot about your product and the importance of having a good product. What differentiates your product from your competitors?

The key to a good trivia night is the material — period. Of course many other factors affect the overall experience — the host, the venue, atmosphere, prizes, specials, etc. — but the bottom line is that the customers who are into trivia and enjoy it (my market) will come back regularly if they like the actual game and the material.

I have a fun, proven format that people like a lot — it involves point wagering, strategy, and wide range of different types of rounds. I keep it consistent and the regulars appreciate that. I write questions that lend themselves to discussion. I am trying to create a fun weekly experience for groups of friends that use it as the perfect excuse to get together, stay in touch well, and foster relationships of all types. I always like to boast that there are 3 couples now married that met at my trivia nights, and the best feedback I constantly get is when regulars tell me it’s given them something to look forward to every week, the perfect excuse to get together with friends, etc.

Since the startup costs are so low in your business, it would seem you have a lot upstarts. How do you maintain competitiveness and pricing integrity in such a market?=

The market has certainly become much more competitive in recent years with several new companies trying to get into it. I stand by the fact that consistency with the material is the key. Our regulars like the style of the questions, the wide range of categories, and the format of the game.

I have all of my hosts constantly plug our website and Facebook page every week as well, which teams can check out for bonus point chances, and that has gone a long way. In an age saturated with social media, getting our regulars to join the Facebook page is huge, as it is a constant reminder of trivia going on and how much fun they have at it. I have the hosts take pictures of the winning teams and encourage them to tag the photos, upload a daily trivia question, and keep everyone posted with daily updates on new venues we start, tournaments for big prizes, etc.

We run 8 week “Qualifying Tournaments” twice a year (summer and winter) in which the top teams from each bar qualify for a big event we call the “Tournament of Champions” for a $1000 cash prize and much more. We had 90 teams at our last event (and would like to grow it — it’s been tough to find a big enough venue that works in the city). The teams really enjoy it and it helps weekly business as well as interest in the product.

What constitutes a good pub trivia question?

I think there are 2 basic keys to a good trivia question. First, it has to be just the right level of difficulty. If 1 is too easy and 10 is way too hard/obscure, then it should be about 6–7. Being on the slightly challenging side is where you want to be; there is more satisfaction for teams in getting the answer right to a more challenging question. You get a better reaction in general from the crowd.

Secondly, the answer has to be accessible from the clues in the question in a way that a well rounded group of people on a team can arrive at the answer after discussion — even if they might think they have no idea upon first hearing the question. I never write questions like “What is the capital of Norway?” and give teams a full song to come up with the answer. That is either something you know or you don’t, and there is nothing fun about the process of arriving at the answer. The question would be more along the lines of “What 3 films, each released in the 1990s, won Academy Awards for … one starred [this actor], one starred [this actor] … etc. etc.”

As I mentioned, the material is the key, and questions that provoke discussions between teammates are more fun and is exactly what we go for. Pub Trivia is foremost a very social, fun activity, and the experience is dictated by the material, which should provoke that type of atmosphere.

When talking with you, it seemed like you were constantly considering new questions, do you have any tricks to spur creativity?

I have some basic go-to tricks as far as the formula I’ve created for a good trivia question, but that is always evolving. There are probably about 50–60 good websites I go to often to get basic information for my most used categories, and I’ll grind out a good question by combining information from them. A big part of the reason I enjoy what I do is that it really is a huge creative outlet.

The product will only be successful if you can keep it fresh, and so I am constantly looking for new ideas and continuously try have it evolve. I will get ideas for different questions and bonus rounds by just observing the world around me in day to day life, talking to friends/new acquaintances, and trying to read as much as I can, watch movies, listen to music, etc. It’s a great business to be in as far as developing a deeper appreciation for the world around you — the arts, sciences, etc.

You mentioned that Wikipedia is not a good source for verifying the answers to trivia questions. What do you consider as a primary source when researching questions?

Wikipedia is a great source for the nuts and bolts of a question (ie. dates, places and names, etc.) which are used in many types of questions, but before using more intricate details from wikipedia pages as clues in questions, I try to back them up with other websites and sources. I have several trivia books that I will get trivia leads from, but mostly use specific information websites on the internet that fit my style of question well.

Do you have idols in the business or trivia world who provide inspiration?

I really don’t. I don’t aspire to be any type of game show host or trivia game show contestant; I just enjoy obtaining information and learning about the world we live in. In no other type of field do you have a full appreciation of how much you DON’T know.

The world is a big place, and there is so much to take an interest in, and it’s enjoyable to continue to expand your interests and appreciation/respect for more and more. This business is also a great general look into what the 20–30 something demographic in the U.S. knows about and what they don’t. The product I try to create is geared toward a well rounded group — it has nothing to do with education and degrees, but moreso having a team of people that compliment each other as far as interest and knowledge base.

I know some people take pub trivia pretty seriously, what happens when an answer is in dispute?

It certainly taps into the natural competitive spirit in people, and it also lends itself to situations were pride is on the line, etc. Early on, I definitely had a few instances of teams challenging the accuracy of questions, and I made a few mistakes. I learned the importance of how to word questions clearly and make sure they lend themselves to the possibilities of other answers, etc. I haven’t had an issue in a very long time, but when I do, I double check my sources (I have my laptop with me at all times and a portable wireless internet device) and will give a team the benefit of the doubt if it is warranted. If not, then I won’t.

It sounds like a fun business to run, are there any downsides?

It is not a typical 9-5 obviously — it is quite the opposite. I have a strange schedule. I have always been a night owl type person, and I can get most of my work done at night. I love being able to work on my own time and hours, and enjoy holing up in coffee shops to get work done during afternoons, but since I’ve been hosting most every night for the past several years, I have limited time for some simple weekly “typical” activities for someone my age — weeknight dinner with friends, primetime television shows, etc. I also fall victim to the conveniences of bar food and drink since my venues comp me — which is nice — but because of that I probably don’t have the healthiest diet in the world, and perhaps fall victim to imbibing more often than I should from time to time.

Any final words of advice for anyone who might be interested in starting a business that might not meet the common start-up profile?

You have to be confident that you do something that is indispensable. That is — you personally have to bring something to the table that no one else can. What you do has to set you apart from any competitors, and it has to be something that only you can do. If you can find a niche like that, and do something that you enjoy and plays to your natural talents, then you’ve found something that you will be successful with.


Thanks to Dan, Kathryn Tanner, Thomas Becker, and Dirk Hobman for their feedback.