Espresso Capital recently sat down with Roland Gossage, Founder and CEO of Groupby, to learn more about his startup journey and what being people-first means when building a great company.


EC: What inspired you to start Groupby?

RG: Two main elements. One, I like to solve really difficult problems, and obviously the issue of search and relevance was one of those. The other is working with amazing people. A lot of the original people are still here at Groupby, and the ones we continue to hire are just that.

EC: Tell me how you went about starting Groupby?

RG: I phoned six of the best people I’ve ever worked with and said – ‘I’m going to start this company called Groupby, I’d like to know if you’re going to join, and, by the way, can you start in two weeks?’. The first question everybody asked was ’What is Groupby going to do?’ to which I had to reply I didn’t know. But I am a believer in the principle that people come first, then you decide the chairs they sit in. That idea has contributed significantly to our success.

EC: So then my next questions is, what does Groupby do?

RG: Groupby is an e-commerce platform that looks after retail distribution, telecommunication and financial services. We provide a user experience platform where people can put the right pieces of content relating to their product or information in front of the right user at the right moment.

EC: As a founder, what obstacles do you face?

RG: I always say if it were easy to start a software company, everybody would do it. We are a people-first company and finding the right employees has probably been the largest challenge, and it’s critical because if you find great employees the journey becomes a lot easier. The other thing is we built Groupby in a slightly unconventional way. We bootstrapped versus going through a traditional institutional round to get a big cheque. It was the more difficult way but ultimately it ended up being much more rewarding and successful.

EC: You mentioned that you are a people-first company. Can you tell me what it is like to work at Groupby?

RG: Our corporate culture is a people-first culture. We like to be inclusive and allow everybody to have a seat at the table. I think that’s something most companies don’t do. It means being very transparent, whether it’s rounds of funding or what’s happening in the current sales quarter. It’s a very communicative and team-oriented sort of environment.

EC: Tell me what it has been like to find the funds you needed to grow Groupby.

RG: A lot of us who did join originally had exited another company. So we all had some money from that exit. We then realized we needed a little bit more money to help accelerate our growth and that’s when we had our first experience with Espresso. What we wanted to do was build out the company to a point that we were still the masters of our own destiny.After we paid Espresso back, we did a small friends and family round. This was probably better for us, versus a VC round, as it was less dilutive.

EC: What skills would you say drive success as an entrepreneur?

RG: I think to be successful, you have to be ambitious and have drive, but you also need other traits like empathy, and have skills that help others become successful as well along the way.

EC: What has been the biggest takeaway from your experience building Groupby?

RG: My biggest takeaway is that if you’re going to start a software company, you have to have very, very thick skin. Be prepared for a lot of challenges, very hard work, and dealing with a little bit of crazy.