The Startup Sit Down’s Trep Takaways: Biggest Startup Surprise (Good Or Bad)

Since the first Startup Sit Down session with DuckDuckGo founder Gabriel Weinberg, there have been some pretty amazing tips, advice and experiences shared with some successful startup entrepreneurs. I’ve gathered some great “trep takaways” from the founder’s  “biggest startup surprise, good or bad.”


Andrew Follett of Demo Duck: Competition is Good.

When I sat down with Andrew back in June, he told me that competition means there’s a market. This can be a good thing:



“When we launched Concept Feedback, we thought we were being innovative and making something new b/c there was no one out there with anything like it, but in reality, we were creating something no one had a real need for. Competition is usually a good sign of a market…and while there are definitely cases where people create a market for something new that people never knew they needed (think iPad), it can be an expensive (i.e. marketing and promotion) and risky proposition.”


Alex Kutsishin of FiddleFly: Ignorance is not bliss.

The very enthused CEO says ignorance by agencies to move to mobile have really surprised him:


“Agencies wait to be reactive, “Is social media going to be that important?” or “Until my client starts to ask for it, why should I even think about it?” The agencies that take on mobile and spearhead the project have a lot happier clients and have a lot more success moving forward.



“I kind of like that it’s going slow because it’s an opportunity to become better. But, ignorance is definitely one of the biggest surprises for me.”



Mike Lewis of Kapost: An unexpeced market


Mike was surprised how Kapost’s original market targeted at media companies, grew:


“The biggest and best surprise we’ve had is that the practice of content marketing emerged and instead of having a product to sell to only media companies, our product could now be sold to anyone who is a content marketer. And anyone can be a content marketer from brand to agency. So the scope of our business turned out to be much bigger than we had originally thought.”



Rich Linden of Mynextgig: Fading funds



Rich thought his angel funding would last forever. Boy, was he wrong:


There have been 100 surprises, good or bad, but I would have to say the first surprise is when you land your angel funding and you think, I’ve got hundreds of thousands in this account, but you don’t realize how quick it goes. I could live on that amount for 5 years! All I need is a beach apartment and a couple surf boards. But, we had a staff of 13 at one point, payroll, marketing, T1 infrastructure, etc. You don’t realize how much everything costs and how quickly the money goes.”



Andres Barreto of Onswipe: Rapid market growth

After securing $5 million in funding for his new project, OnSwipe, Andres told us it was due in part by the surprising rapid tablet market growth:


“When I started getting into the Tablet market, and the touch and ad world, I originally thought there would be growth and opportunity, but I didn’t know it was going to be that fast. It was March, and we had already landed the NY Times and they said “Cool, we love what you’re doing, we want to use the ad stuff and we want it in two weeks.” We said, “Uhh, great!” The market grew so fast and we had to grow so quickly. For us, it’s been an amazing opportunity, but it hasn’t been a walk in the park. So far though, we’ve been able to keep up, and I think that was reflected in our first two rounds of funding – we closed both deals in around 30 days.”


So, whether it’s a market surge or funding follies, entrepreneurs are always in for surprises, no matter how much pre-planning is involved. Advice? Expect the unexpected.


Photo Credits

Demo Duck / Onswipe / Mynextgig / Kapost / FiddleFly