career at Bain & Co. in traditional big company stuff. I was pretty committed to finding something I could be passionate about.
When we closed our first deal, which was a consulting deal two months into having the idea for Floored, I remember being so giddy that someone was going to pay us for something.
X: How did you land that first customer deal?
DE: I asked every person that I knew who had some familial connection to real estate to get me started. What you find is most enterprise people are pretty bored with their jobs so if you walk in as a potentially imaginative [person] talking about something exciting, the worst-case scenario was I would entertain them for 15 to 20 minutes. You do it well enough for a few meetings in a row and sometime this begets other meetings.
X: Did you have to walk customers through different use-cases for the platform? What did you tell them this was going to change?
DE: You have to be intellectually honest about what you’ve got and what you don’t have. Often times you want to spend these sales meetings talking as little as possible. As a chatty guy that was something hard for me to grok. You’ve got to let your customers tell you what they want so you can change your sales pitch in the middle of the meeting.
We’re homing in on very consistent needs across the industry. I’m also trying to listen for where these folks spend money on what seem to be anachronistic processes.
Often times, the overlap between software teams and people who know details about enterprises is very low. We’re trying to rapidly get as knowledgeable as possible on the real estate industry. Some of the best entrepreneurs I know in enterprise tech take an advantage in the vertical space in which they are operating and then marry that to unique software talent.
X: How did you gauge the size of the potential market?
DE: We tried to do as little research as possible that would still give us enough confidence to go through with this. We asked people who were willing to share with us “How much money do you spend on X? What does that look like across all your different properties?”
These individual customers were spending tens of millions of dollars on marketing services. With 500 big developers in New York alone, we had some comfort we could build a sizeable business if we just nailed this city.
What also moved the needle on my confidence was hearing real people say “I spent $5 million on this [process] and I wish I had a tool that did that and I would spend $4 million on it.”
X: Are you focused on commercial or residential real estate?
DE: We’ve started to branch out. We’ve wanted to build a brand and sales strategy in commercial real estate. We’re dabbling in retail, residential, and non-traditional real estate like restaurants and hospitals. Part of me wants to take money from everyone who is willing to give it to us. Part of me wants to have a strategy I can hand off to someone else to run enterprise sales within a specific vertical.
X: Operating your business in New York, how do you find talent?
DE: Trying to hire software engineers is hard because the problems themselves might not be that interesting to really talented folks. If you’re going to hire A-level quality folks, you better have an A-level quality problem.
There is a certain degree to which your early team really sets the sense of quality. I personally feel most days I’m the least talented person on my team, which is super scary but also really fun.
X: What has been some of the best advice and toughest criticism that you’ve gotten when you started to seek funding?
DE: The toughest criticism was when my best friend on the other side of the table said “I’m not going to invest in your stuff.” I was surprised and a little hurt but he’s good at what he does and had lots of valid criticism. It really hit home that we did not have a perfect business. Very few that raise capital do.
The best advice I got was to talk to customers with most of your time. If you’re not selling or recruiting as a CEO—I’m not on the [tech] building side—you’re probably doing something wrong.
