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Boris Pfeiffer, CEO at Riddle, advises startups and young entrepreneurs to avoid external funding and influence for as long as possible. Click here to find out why

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Boris Pfeiffer Riddle

First of all, how are you and your Family doing in these COVID-19 Times?

Boris Pfeiffer: Thank you so much for asking. We feel very lucky – none of our team or their families got infected. Riddle has also continued to grow and thrive because so many brands, events, and sports are moving online during the pandemic, so we haven’t had to make any painful choices about our team’s size.

Tell us about you, your Career, how you founded Riddle

Boris Pfeiffer: I feel like everything I have done in my life has eventually led to my founding I started my career in banking, working for the German head office of Société Générale, learning the ropes of trading, deal-making, and dealing with high net worth individuals. 

From there, I moved on to starting my first company, selling it to a, which I joined as the European General Manager, and taking it public on NASDAQ. Unfortunately, the bubble burst, so we had to close the shop. 

I went on to join other successful startups that got sold, then had my last big corporate job as the E.U. General Manager for one of the leading mobile games companies – – before starting Riddle back in 2014. As part of my journey, I also ran the European operations for – a quiz portal back in the early 2000s, which was the 28th biggest website in the U.S. at the time before being sold to for over $100 million.

 You could say, Riddle represents the culmination of all my experience – from running a quiz portal to working in the games industry for a long time. It’s all about making quiz creation and lead generation fun for both the users and their audience – our intuitive the user interface was heavily inspired by game development and breaking complex tasks into easy to handle steps.

How does Riddle innovate?

Boris Pfeiffer: My co-founder Mike and I have a lot of experience when it comes to quiz creation as we both worked for That helped us create a solid foundation for our product – we knew what features and capabilities were critical. But we made a key strategic decision – from the first day, we decided as founders that we were going to handle all support ourselves, and not outsource it.

This has been key – we get to hear firsthand where our users are struggling and which features they like the most. We have made it a habit to use that feedback to inform our product development cycle as well as validate potential new features with our audience before we start development. 

Innovation happens automatically when you have the chance as the CEO to speak to your paying customers on a daily basis.

How the Coronavirus Pandemic affects your Business, and how are you coping?

Boris Pfeiffer: When the virus started getting really bad (around March), we saw a huge dip in new subscriptions sold and also got a lot more cancellations than usual. That was fully understandable, of course, and we immediately made adjustments to counter this effect. 

First, we added a ‘take a break’ function to allow our customers to pause their payments for three months instead of canceling right away. We’re very customer-first, and made ensured that this pause wouldn’t hurt their business – any quiz content they created and embedded on their websites would still work while the account was in pause. 

I next got our product team together – and we shifted our product roadmap to focus on features that would help our existing customers most. This focus on retention over acquisition was key – as we did not expect many new businesses to sign up. 

We also re-focused our marketing to target more pro sports teams as a key growth area. With the cancellation of all live sports, pro sports teams needed a steady stream of interactive content to keep their fans engaged. Quizzes and personality tests worked really well for them, and quite a few pro teams and leagues generated whole microsites powered by Riddle quizzes and other content (like these by the NFL’s San Francisco 49ers and the N.Y. Giants).

Did you have to make Difficult Choices, and what are the Lessons Learned?

Boris Pfeiffer: I was very fortunate to avoid facing any big difficult decisions. Sure, we immediately decided to stop all discretionary spending like free lunches and held back on some investments, but overall, my co-founder Mike and I have always run our businesses as lean as possible, which really benefited us during the height of the pandemic. 

I also don’t think we are even close to done with COVID, so we are still very cautious with our expenses. The lesson for other founders – being a small and lean company can be a huge asset in a crisis as it allows you to quickly alter course on the cheap while having the resources to get you through a crisis. 

I would think that a VC-backed startup, expected to grow exponentially each month, would have had a very hard time during the crisis. 

How do you deal with Stress and Anxiety? How do you project yourself and Riddle in the Future?

Boris Pfeiffer: It actually takes a lot to stress me out. The only times I do get stressed is when too many Slack chats, phone calls, and people all want my attention at the same time. The best way to deal with that for me is to drop everything and simply go outside for a few minutes to breathe and to remind myself that everything can be dealt with one at a time.

The good news is that Riddle has been on a solid and steady growth path for quite some time, and I do not expect that to end. I can see myself running the company for the foreseeable future and maybe passing it on to my kids one day.

Who are your Competitors? And how do you plan to stay in the Game?

Boris Pfeiffer: There are quite a few quiz makers in the market – as more and more companies recognize that quizzes and personality tests are the best way to both get high engagement rates from site visitors and also generate insane opt-in rates for leads (40% and higher). 

We have seen a few of our competitors like and (now re-branded as shift their model from targeting a broad market in the $50 to $200 range a month $10,000 a month or more.

I firmly believe that while there is a huge market for quizzes and interactive content, you have to stay realistic with your pricing and allow the customer to make money from the quiz content. We will stay in the game against these two on price and value delivered. 

Other competitors include,, and Their model is similar to Riddle, but in this era of increased privacy regulation, we already have a huge advantage by making our quiz embed 100%compliant with the E.U.’s GDPR and California’s CCPA. 

This includes hosting everything on our own server farm in Frankfurt, Germany, with backups in Luxembourg and (most importantly!) not including any kind of trackers in our quiz embed codes. Re-targeting our customers’ users or re-selling data from the quizzes has never been part of our business model – we think it’s bad karma, and legally dubious besides.

Looking at the insane amount of cookies and trackers that other quiz makers put on their customers’ websites, I don’t think that they take the same approach. With this global focus on data privacy, we will stay a few steps ahead of our competitors by adding more privacy-related features to our quiz maker. We also will continue having everyone in the company help out on customer support, with my co-founder Mike and myself at the forefront. This will allow us to keep innovating with Riddle – and becoming ever-more integrated into our customers’ marketing strategies.

Your Final Thoughts

Boris Pfeiffer: My one tip for other founders? I wish I knew this when I launched my first startup so many years ago. 

If you’re reading this and considering starting your own business or are in the early stages of growing your own company, avoid taking outside money and influence for as long as you can – unless you are in a hyper-growth market. 

Venture capital is great – but if you have to continually focus on short-term exponential growth to satisfy your investors, you will miss out on building an amazing product. In the long run, really good products that allow customers to make money will survive any crisis. 

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Kokou Adzo is the editor and author of He is passionate about business and tech, and brings you the latest Startup news and information. He graduated from university of Siena (Italy) and Rennes (France) in Communications and Political Science with a Master's Degree. He manages the editorial operations at

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