After Losing a Partnership, Laying Off Her Team and Dealing with $100 Million at Stake
Kate Stillwell, founder and CEO of Jumpstart, a natural disaster insurance startup, built her company back up after a devastating blow.
Photo: Alex Tran, Plug and Play InsurTech
As appearing in Women Entrepreneur
In the Women Entrepreneur series My Worst Moment, female founders provide a firsthand account of the most difficult, gut-wrenching, almost-made-them-give-up experience they had while building their business — and how they recovered.
Jumpstart, which launched on Oct. 2, 2018, is a new type of natural disaster insurance that helps families and individuals bounce back from earthquakes through an immediate payout initiated via text message. Jumpstart connects the insured person to the insurer.
Founder and CEO Kate Stillwell said she believes her company is, at its core, about resilience — ensuring more money comes into the system after natural disasters and creating an upward spiral of recovery. But when natural disasters occur, everyone experiences losses at the same time, so insurers themselves need insurance (“reinsurance”). She tells us about her worst moment, when Jumpstart unexpectedly lost a partnership and up to $100 million was at stake.
My worst moment was eight days before Jumpstart’s initial planned launch, about a year ago. We had built up a team of eight people. For 16 months we had worked shoulder-to-shoulder with our reinsurance partner, in preparation to sign the agreement that would authorize us to start selling policies on their behalf (and fund us with six months of runway).
But someone got cold feet, and up to $100 million — the entire pot of money we had in capital reserves to pay out our customers — was at stake.
I was in our office in a coworking space in Oakland, meeting with my team as part of our weekly “sprint.” My phone rang, and since I recognized the number calling was our partner’s account manager, I excused myself and walked into the common space.
The account manager had been my primary point of contact for the past 16 months, and I could hear that he was close to tears. I remember him saying that he wished he wasn’t the one who had to give me the news but that it had been decided that our two companies were no longer going to be working together. They had called off the partnership.
There was silence for about 10 seconds.
