How This Entrepreneur Bounced Back After Losing a Partnership, Laying Off Her Team and Dealing with $100 Million at Stake

How This Entrepreneur Bounced Back After Losing a Partnership, Laying Off Her Team and Dealing with $100 Million at Stake


Kate Stillwell, founder and CEO of Jumpstart, a pure catastrophe insurance coverage startup, constructed her firm again up after a devastating blow.

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Within the Girls Entrepreneur sequence My Worst Second, feminine founders present a firsthand account of probably the most troublesome, gut-wrenching, almost-made-them-give-up expertise they had whereas constructing their enterprise — and the way they recovered.

Jumpstart, which launched on Oct. 2, 2018, is a brand new kind of pure catastrophe insurance coverage that helps households and people bounce again from earthquakes by way of a right away payout initiated by way of textual content message. Jumpstart connects the insured particular person to the insurer.

Founder and CEO Kate Stillwell mentioned she believes her firm is, at its core, about resilience — guaranteeing extra money comes into the system after pure disasters and creating an upward spiral of restoration. However when pure disasters happen, everybody experiences losses on the similar time, so insurers themselves want insurance coverage (“reinsurance”). She tells us about her worst second, when Jumpstart unexpectedly misplaced a partnership and as much as $100 million was at stake.

What follows is a firsthand account of this particular person’s expertise. This interview has been edited for size and readability.

My worst second was eight days earlier than Jumpstart’s preliminary deliberate launch, a couple of yr in the past. We had constructed up a workforce of eight folks. For 16 months we had labored shoulder-to-shoulder with our reinsurance associate, in preparation to signal the settlement that will authorize us to start out promoting insurance policies on their behalf (and fund us with six months of runway).

However somebody acquired chilly toes, and as much as $100 million — all the pot of cash we had in capital reserves to pay out our clients — was at stake.

I used to be in our workplace in a coworking house in Oakland, assembly with my workforce as a part of our weekly “dash.” My telephone rang, and since I acknowledged the quantity calling was our associate’s account supervisor, I excused myself and walked into the widespread house. 

The account supervisor had been my major level of contact for the previous 16 months, and I may hear that he was near tears. I bear in mind him saying that he wished he wasn’t the one who needed to give me the information however that it had been determined that our two corporations had been not going to be working collectively. They’d known as off the partnership.

There was silence for about 10 seconds.

I requested if he may inform me why, and I bear in mind listening to that it was a mix of the excessive dangers and the truth that we had been a startup. Ultimately, we hung up.

Since Jumpstart pays out in earthquakes, the place everybody wants cash without delay, we’d like entry to a big pool of capital. However a startup doesn’t have thousands and thousands of dollars in reserve, so we associate with a number of established corporations who’ve deep pockets to make the payouts. There’s a David and a Goliath dynamic; we’re mutually dependent. The product can solely be offered if we cooperate. The distinction is, for “David” (us), that is the one product: cooperation is life or loss of life. For the “Goliath” (the associate), that is considered one of many merchandise — they produce other revenue streams.

In my earlier startup, we had an ideal partnership with this explicit Goliath, so towards the number-one piece of recommendation from nearly everybody within the trade, I had agreed to be unique. That was my first mistake — let’s name it an error of optimism. One other of my errors? I took at face worth a declare that the associate would make us an funding price a number of months of runway. I ought to have raised funds sooner from different sources.

I felt blindsided, however that’s solely as a result of I used to be carrying rose-colored blinders. I ought to have seen the indicators — months of delays, creating new hurdles every time we cleared the final one, the fitting hand not speaking to the left hand, causes that didn’t fairly add up.

I returned to the workforce and pretended like nothing had occurred as a result of they had been nonetheless in the course of the assembly. That day it was my flip to drive the carpool of children residence from college, so I picked them up after which texted my mom about what had occurred. I used to be very withdrawn. I keep in mind that my mom gave me what I needed to listen to — “You don’t deserve that!” — whereas my husband had a unique mindset: “Effectively, you knew this might occur.”

With out the authority to promote, we couldn’t launch — and we had been at detrimental runway. The day after I acquired the decision, I needed to break the information to eight totally different folks on the workforce individually.  

Certainly one of my teammates was leaving the subsequent day to settle her late mom’s property. I requested if I may drive her to the airport within the morning. She knew one thing was up. On the best way, I bear in mind telling her how sorry I used to be however that we’d must let her go. We’d each identified going into it that working for a startup is dangerous, but it surely was exhausting as a result of we’d simply employed her about six weeks earlier than, and it was her first job after a profession change.  

I went again to the workplace and met with our principal developer, who was a contractor, and advised him the dangerous information. I bear in mind saying, “We’ve no extra money. The launch is now many months, if not years, away. We don’t know what the way forward for the corporate is, and I’m going to be shedding all people else.” He spent the subsequent two to 4 hours buttoning issues up and left. After that, I advised one other co-worker what occurred — and that I didn’t have to put him off that day, however we had been in danger, and I didn’t know precisely what would occur over the subsequent two weeks. I advised him it could be a good suggestion to start out searching for different jobs. And that night time, I had dinner with one other teammate and advised her the identical factor.

That’s how the workforce went from eight to 6 in sooner or later. There we had been: no launch, workforce gone, out of cash, no foundation of elevating cash. I used to be offended, humiliated and simply plain unhappy. However I used to be nonetheless optimistic: We had fallen off the proverbial cliff, however we didn’t die.

The core worth proposition of our product — what we’re basically promoting — is private resilience. It’s sources to faucet into the internal energy that’s already there and adapt to the brand new regular after a shock. So, as an organization, I assumed, we’d higher be capable of stroll that discuss.

5 weeks after that preliminary name, me and two of my remaining teammates — individuals who knew their jobs would probably be gone quickly — took an enormous danger. We determined to spend the corporate’s remaining funds on a flashy publicity stunt at an insurance coverage convention in Las Vegas. We introduced a “shake trailer” — which simulates an earthquake — and 400 convention attendees took a journey in it. Certainly one of them known as it “good advertising and marketing” and the “most enjoyable factor” on the convention. About eight months later, his firm would find yourself being our subsequent associate. 

However that was months away. On the afternoon of the convention’s second day, I needed to sit down with each workforce members who had accompanied me. I bear in mind telling them, “I can’t pay you after in the present day. I’ve to put you each off.” Certainly one of them burst into tears.

It took us over a yr to make a comeback, however we survived by the grace of some trade insiders who offered sufficient funding to tide us over. I bear in mind them saying, “We all know what occurred to you, and it sucks. Nobody ought to must undergo that. We wish to be sure you come out alive.”

From this expertise, I discovered that there’s no different alternative than to be optimistic. Entrepreneurs are creating the long run — not only for ourselves however for our communities and our collective youngsters. That’s an enormous accountability and an enormous alternative. Having the braveness to be optimistic — within the face of setbacks, despite shock — is the check of being a real entrepreneur.

To others going by way of one thing comparable, my recommendation is to remain optimistic and make selections assuming the most effective. I relied solely on optimism and didn’t have sufficient of a security web or plan B, so together with optimism, make a freaking backup plan!

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