It was a beautiful feeling.
We had just raised our first after-seed round of investment, bumping my salary as cofounder and CTO from a voluntary $24k a year to a healthy six figures, while simultaneously driving up the value of my stock equity. The rest of the team, my comrades in arms, were similarly bumped and positively impacted.
Flash back to around 2011 at my previous company.
We had a great team, a solid product, and even some paying users. We’d all been slaving away at sub-market wages for quite some time, putting in sweat equity to build something real. To reward ourselves for our wisdom and hard work, we went on a well-deserved shopping spree at the Apple store and bought ourselves the latest Macbook Pros, with bells and whistles.
I would have thought you insane if you suggested to me, back in that day, that we were at the top of a rollercoaster. And yet approximately two years later, we were at the bottom, broke, with no real shot at getting back up. What the hell happened?
“Fail Fast, Fail Often” and “Fail Better” are phrases that startups always hear from their mentors, and many live by (especially after reading The Lean Startup). Here at Digsy, failing fast gets mentioned at least once a day. Even though we’ve fully embraced the “fail fast” mantra to help our business succeed, the fear of complete failure is still there. Any startup has fears of failure. At Digsy we have gone through our set of failures, but it’s how we push through to the other side of our failures that keeps us going. Failing fast and quickly learning from our failures helped us get closer to product-market-fit before we went down in flames.
This is going to sound crazy, but one of our biggest failures occurred when we listened to our customers.
We’re a startup in the commercial real estate industry so we built our product based on many, many conversations with our potential customers: commercial real estate brokers. In every conversation, we would ask them about their pain points, business processes and how technology could help them accomplish their goals more easily. We would hear the same things over and over, so we decided to build a product that solved these pain points and addressed their wants and needs. We did this twice, and we crashed and burned. Twice.
It was ugly.