The Moment of Truth
It was early 2012. My cofounder and I were huddled around a laptop nervously pitching yet another investor (that’s right folks, remote pitches existed long before Covid). But this wasn’t just any VC. Staring back at us from the screen was Brad Feld, cofounder of Foundry Group and TechStars.
It was the early days of DataHero and we were trying to raise our Pre-Seed round. Our vision was to create the world’s first cloud-native business intelligence platform. We believed that the shift to software-as-a-service would lead to massive demand for analytics solutions capable of unlocking insights across those services. Key to achieving this goal was the ability to identify and standardize data regardless of where it came from. To prove out our concept, we had created a prototype that could take any CSV file and automatically identify and normalize the data it contained.
Of course, it was the early days, so our prototype had lots of bugs.
DataHero 0.8 — aka why DataHero’s first hire was a designer
Brad Feld was the “final boss” in our quest to secure a term sheet from Foundry Group. We had already spoken with his three partners, Ryan, Seth and Jason, each of whom had given us a thumbs up. So there we sat, dutifully answering Brad’s questions before transitioning into a demo.
Brad’s eyes lit up as we showed him our prototype, importing a variety of CSV files that were automatically turned into beautiful charts. He then jumped into more questions,
“Can your system really take any CSV data and understand it?”
“Yes!” replied my cofounder and head of product, sharing more about how the underlying technology worked.
“Does the data need to be in a specific format?”
“No,” replied my cofounder, “DataHero can figure it out automatically!”
At that point, I started to get nervous. Brad was asking what were starting to feel like leading questions and my cofounder was getting caught up in the excitement.
“So…you can literally take any CSV file and load it into DataHero right now…?”
Before I could kick my cofounder under the table, he excitedly blurted out “Yes!!” as I watched a mischievous smirk pass across Brad’s face.
“I just emailed you a CSV export from my Withings scale. Can we try it?”
Actual photos of Brad Feld on a startup pitch call
Cue the record scratch.
At that point, we faced a choice: do we try loading Brad’s file, knowing that there was a high likelihood something would go wrong (seriously…our prototype had a lot of bugs), or do we back pedal and try to escape the corner that we’d painted ourselves into?
We took one look at each other and, without saying a word, answered, “absolutely!”
I then found the CSV file in my email, loaded it into DataHero and…
…it completely broke.
We desperately looked through the errors in front of us and figured out pretty quickly what went wrong. We told Brad that we knew what the issue was and asked if we could email him the results later that day. He agreed.
We got off the call frustrated and deflated.
We figured that we’d just blown our chances with Foundry, but nonetheless got to work fixing the bug in our prototype. A couple of hours later, we sent Brad a PDF with the charts that DataHero had generated from his data.
The next morning, we received an email from Ryan McIntyre with a term sheet to lead our Pre-Seed round.
A few weeks later, we went to Boulder and met Brad in person for the first time. I asked him about our experience and what made him decide to invest in us.
“The way you answered,” he responded, matter-of-factly.
“Look, I knew it would probably break,” Brad continued. “I didn’t care if it worked or not, I cared about how you answered. I would have invested even if your response was ‘we’ll send it to you the next day.’”
“The fact that you were willing to try it live — right then and there — told me that you guys believed it would work. That you believed in what you were pitching me. The way you responded told me everything I needed to know about you guys.”
Over the years, I’ve learned an incredible amount from Brad and his partners at Foundry, but this lesson always stuck out:
When the moment of truth arrives, how you respond matters as much as what you say.