September 21st, 2020
By Jenny Fielding, Managing Director of Techstars NYC
Nobody told me that building a startup was going to be the most challenging event of my life. I experienced this first hand when I left corporate American to pursue a crazy idea. Most founders I’ve met have had a similar experience, yet despite this reality, so much of what’s depicted in the startup Twitterverse and on Techcrunch is the glamour and prestige of starting up.
We all love a hero and tend to ignore the unsexy grind and roller coaster of emotions that most founders endure. It’s important to talk about what really happens behind the scenes to better support founders as they navigate the ups and downs of getting a business off the ground.
Working with hundreds of founders as an investor and Managing Director at Techstars NYC. I’ve seen my fair share of startup chaos, company dysfunction, and all around hard times. Many companies are not able to make it through. But I’ve also worked with some incredibly resilient and persistent humans who refuse to give up and are able to lead their companies from darkness into light.
Founder Rising is a podcast series of interviews that looks behind the scenes to expose some of the hard moments in running a business. From cofounder conflicts, to struggling to find product-market fit, to running out of cash, we’ll hear about those make-or-break moments when everything can either come together or go totally off the rails.
While you’ll have to listen to Founder Rising to hear all the juicy details, I want to share two stories that particularly resonated with me to give you a taste of what’s to come.
As I interviewed the founders, perseverance was a theme that came up again and again. One of my favorite interviews is with Ben Uretsky, the cofounder and founding CEO of DigitalOcean, because he opened up to me about the early days when most people thought he was totally crazy for launching a product competitive to AWS. What drove him to continue down the path and persevere? According to Ben, it was “customer love!” The DigitalOcean product really hit a cord with developers and “that kind of customer reinforcement allowed us to really persist with investors who were very skeptical of taking on Amazon.”
Another prevalent theme was around cofounder issues. I struggled with this while building my own startup and heard about it multiple times during my Founder Rising interviews. No one tells it straighter than Laura Spiekerman, Cofounder and CRO of Alloy, who recalls a yelling match in NYC’s Gramercy Park between her cofounders. She told me, “We are so different that I think we didn't really know how to talk to each other and we didn't know how to trust each other on company building things.” Even though their product visions and company mission aligned, how to get there was more contentious. As Alloy’s first investor, I was familiar with their founder struggles and am super proud to see how far they’ve come. After years of hard work, the Alloy founders are by far one of the highest functioning teams in my portfolio.
Listen now to my conversation with Ben, and subscribe to Founder Rising so you never miss an episode of Founder Rising.
Follow Ben on Twitter: @benuretsky
Follow Jenny on Twitter: @jefielding
Jenny Fielding is the Managing Director of Techstars New York and multi-time tech founder. Follow her on Twitter @jefielding.
Founder Rising: Finding Motivation by Battling Yourself – with Shastri Mahadeo
Give First: Susan Standiford on the five traits of leadership
Founder Rising: Hacking Resilience by Celebrating Small Wins — with Laura Spiekerman
Founder Rising: Take All Advice With a Grain of Salt — with Christie Horvath
Founder Rising: Jenny Fielding Hosts Techstars’ New Podcast That Goes Behind the Scenes of Starting Up