How To Properly Communicate With Your Employees With Dennis Crowley of Foursquare

Dennis Crowley is the former CEO and Executive Chairman of Foursquare – one of the most popular technology startups in the world. In our interview, the main theme is communication and the importance of over-communicating with your team; he stressed it repeatedly throughout our conversation, and it gives some insight into the type of person that he is. He is a fantastic leader that focuses on building and has dedicated his entire life to his mission of sharing & using technology to share your location. He also carries a book everywhere he goes that he tends to write in. He showed it off during our interview, which in my opinion, gives us a behind the scenes look into his thought process.

March 13, 2018 25 Mins Download (MP3)


01:33 How is your day going?
01:56 Imagine you just had the absolute best day of your life. Where are you going to eat, and what are you eating in order to make your day complete?
03:13 What were some of the ways you were able to achieve your first 100 customers?
04:45 Tell me about a time where you felt lost/blind in business. How did you overcome it?
05:51 Was there anything along your journey that has made you as focused as you are now?
10:00 Explain That Gram
20:22 The Blind Entrepreneur was created for those individuals that may be temporarily blind in business. To those individuals, what are 3 pieces of advice that you could share with them?

How Dennis Crowley is Obtaining His First 100 Customers

Well, for me, the answer would be to have a really clear vision on what you want to attain; you need to over-communicate that vision to your staff so that they can all be on the same page. Tweak the vision statement and strategy so that it can be repeated easily to anyone. That is what you want to aim for. Take this approach and you can steer the course in your business. Keep focus. Don’t forget to over-communicate to keep relevant persons on the same page.

Three Pieces of Advice From Dennis Crowley

The first piece of advice I have to share is to keep your focus. Over-communicating and not getting distracted are some of the best ways to achieve this. As a matter of fact, I have a little notebook that I carry around with me that I use to record every important thing that I need done; it’s like a to-do list of sorts. Secondly, sometimes it can feel like your best ideas are your craziest ones. People will oppose what you think. You hear that it’s a bad idea, it’s already been done, and so on. Do it anyway. You can learn something valuable from your own experience with this idea. And lastly, it is crucial to have that work-life balance. I personally have been a bit guilty of this during my time at Foursquare, but I have been able to figure it out now. Striking that balance can lead to increased clarity and happiness, to name a few.