In this episode of Startup School Radio, host Aaron Harris started by sitting down with Danielle Morrill, the co-founder and CEO of financial data platform Mattermark.
Earlier in the episode Harris interviewed Peter Reinhardt, the co-founder and CEO of Segment, the startup that provides a customer data hub and analytics API.
One especially interesting part of the episode was hearing Danielle discuss how she made the difficult decision to leave her job as employee #1 and director of marketing at Twilio, and how taking that big risk ultimately led her to found Mattermark.
This portion begins at 41:50 of the podcast:
Aaron Harris : Twilio was going well, you’re on the ground floor there, you’re building up all these teams. Why leave? It’s such a cool product, it’s a cool company from what I can see from the outside. It has great culture, great support. It’s always been a company I’ve admired.
Danielle Morrill : It is a wonderful company. All those things are true. For me, I think, my motivation still comes from more leverage on my time.
I was about three and a half years in. I had just moved to London opened up the office in Europe and figured out how to do all that stuff. I came back, and I was in the car on the way back from the airport, and I called Jeff [Lawson, Twilio’s founder and CEO] and I was like, ‘I’m done man. I’m done. I mean, we have time, I can spend four more months, it’s not like [I need to leave] right now. But I just know that I’m done.’
I wanted to end things on a high note, at the top of my game when I’m contributing the most, instead of this long taper I see people take in their work, where you realize you don’t want to be somewhere anymore. It’s like in relationships, when people stay in the relationship even when they kind of know they can see the end. For me, I want to leave as soon as I can see the end, and set things up so that the next people coming and taking over are starting with a happy person that can onboard them, that cares, who is not checked out. I don’t like to do anything halfway, and being mentally checked out is the most painful thing I can imagine. Being bored – I just can’t stand it.
…I could have made other changes. You know, we’d been playing around with my role. Discussing maybe having me go into Corp Dev… I know I could have picked any piece of those responsibilities and gone deep on that. But I think there’s also sometimes a need for a little bit of creative destruction in your own life. If I take all this away and I’m free, what would I actually choose if I didn’t have constraints? It’s a fairly risky thing to do, I guess, for most people. But to me, it just lets you be the most creative, because it gives you space to ask, ‘What if it was completely different? What if my life was completely different?’