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Masters of the Turnaround: “We need to remain optimistic, even in the face of shocking setbacks” with Kate Stillwell and Jason Crowley

Kate Stillwell is the founder and CEO of Jumpstart, a new type of natural disaster insurance that helps families and individuals bounce back through an immediate payout initiated via text message. For the past two decades, Kate has served as one of the most prominent earthquake risk consultants in the San Francisco/Bay Area. She holds an […]

Kate Stillwell is the founder and CEO of Jumpstart, a new type of natural disaster insurance that helps families and individuals bounce back through an immediate payout initiated via text message. For the past two decades, Kate has served as one of the most prominent earthquake risk consultants in the San Francisco/Bay Area. She holds an MBA from the Haas School of Business at University of California Berkeley, a M.S. in Civil Engineering from Stanford University, and a B.C.E. in Civil Engineering from the University of Minnesota.


Jason Crowley: Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to this specific career path?

Kate Stillwell: I realized that if an earthquake hit my hometown of Oakland, California, it could easily cause physical and economic repercussions as severe as the aftermath of Hurricane Katrina in New Orleans. As a structural engineer I experienced a professional crisis — designing buildings to stay secure during an earthquake is only one piece of the resilience puzzle. One of the biggest missing pieces is getting enough money to flow in after an earthquake, so each of us can get our needs met and our lives back on track, thus the genesis of Jumpstart.

I realized the need for Jumpstart was dire — even though the US Geological Survey reports a 99 percent chance of a magnitude 6.7+ earthquake somewhere in California within the next 30 years, only about 11 percent of California households in 2016 purchased earthquake insurance, which is not required by residential mortgage lenders. As a result, only a fraction of needed rebuild funds are likely to flow into post-quake California. Jumpstart intends to upend this status quo by appealing to significantly more people than those who currently buy earthquake coverage. To do so, Jumpstart, which officially launched on October 2, 2018, created an unorthodox product that keeps what people love about insurance — receiving money when it’s needed — while eliminating what people hate — high costs and complicated claims processes.

Crowley: Can you share your story of when you were on the brink of failure? First, take us back to what it was like during the darkest days.

Stillwell: It was eight days before Jumpstart’s initial planned launch, in late summer 2017. The team was eight people strong, and we’d been working closely for 16 months with our reinsurance partner (the source of capital reserves needed to pay out Jumpstart’s future customers). I was just about to sign the agreement that would authorize Jumpstart to start selling policies. Then my phone rang and I received the bad news from our main contact there — someone up the chain got cold feet and they were removing themselves from the deal. We lost backing worth $100 million. Jumpstart could no longer launch, I had to let my staff go and I had to start from square one to find a new backer.

Crowley: What was your mindset during such a challenging time? Where did you get the drive to keep going when things were so hard?

Stillwell: I was completely blindsided at the time. Though in retrospect, I realized I had been wearing rose-colored blinders throughout the whole process with this partner. There were many warning signs that I didn’t want to believe — several months of delay after our original launch date and a barrage of constant, repetitive issues.

After a very emotional couple of weeks, I realized I needed to get back up and practice what I preached. The core value proposition of our product is personal resilience. That’s what we’re fundamentally selling. Jumpstart is meant to provide the resources to tap into inner strength and adapt to the new normal after a shock. That’s what gave me the drive to build myself back up and make a new partnership happen.

Crowley: Tell us how you were able to overcome such adversity and achieve massive success? What did the next chapter look like?

Stillwell: If I was going to talk the talk, I had to walk the walk. I decided to take a major risk. Five weeks after that initial call, myself and my two remaining teammates went to a major insurance conference in Las Vegas and spent Jumpstart’s last dollars on a flashy publicity stunt. We brought a “shake trailer” that simulates an earthquake. 400 conference attendees participated and one company said it was the best part of the event. Not long after that, that company became our partner, and we ultimately launched with them a year later (this past October).

Crowley: Based on your experience, can you share a 3 actionable pieces of advice about how to develop the mindset needed to persevere through adversity? (Please share a story or example for each.)

Stillwell:

1. Enough with FOMO, Time is your Friend.

There are definitely times when fast action is needed, but there are other times when it actually turns out better if you wait or refrain from taking action. Once I heard this described as “constructive procrastination.” I’m not saying you should wait until the last minute for everything, but there are some things which, if you do them now, the situation might change and it might nullify your work — or, someone with more time might step in. Here’s a little example: we’ve been collaborating with a prospective partner to explore possible international expansion. During one call, I agreed we would propose a pricing scheme. It was no small chunk of work, and I would need to write detailed requirements for a teammate to execute. The more I delayed, the more shame I felt for not following through. Then, after about a month, the partner told me that someone on their side had developed pricing. What a relief, not because someone else did it, but because if we had done the work, it would have been overridden anyway.

A related piece of advice is “you can do anything for a year.” This is the mantra that kept me going through the first year after my second child was born — which, for a nursing mother with a two-year-old and a full-time job, is sheer physical exhaustion.

2. Stay in the present.

This is about managing anxiety. Most anxiety is either related to the past or the future. Staying present doesn’t mean you shouldn’t plan or reflect; it’s more about maintaining focus at any one time, particularly when your to-do list is so long you feel overwhelmed or even paralyzed. It takes a lot of practice to stay in the present, but luckily, you can get that practice in many different ways. Regular meditation is one way to practice. Playing a fast-paced or competitive sport is another way. One more way is scheduling periods of time with no interruptions (really! turn off all email, texts, etc.).

3. Stretch yourself.

This is about developing faith that you will be able to persevere. When I was 18 I was diagnosed with lymphoma (cancer of the immune system). It wasn’t a “death sentence” but it meant major abdominal surgery followed by four months of radiation treatments that left me weak, bone-thin, and barely able to concentrate. This was on the heels of two other setbacks in my personal life. It felt like my grief and suffering would never end, but eventually, like everything, it did. That relief — the end of suffering — is a core memory that I regularly draw upon for reassurance, every time I’m in the thick of difficulty. Put yourself in situations where you might fail, where you’ll have to push yourself. Then you’ll know what it feels like to be forced to persevere. Specifically, what do you choose to do? It might be as straightforward as running a marathon. It might be as emotional as standing up to a challenging boss. It might be as complicated as moving to a new city, or changing your career. When you test the extent of your capabilities and endurance, you earn fortitude and confidence for yourself.

Crowley: None of us are able to achieve success without some help along the way. Is there a particular person who helped get you to where you are? Can you share a story about that?

Stillwell: One of the dirty little secrets about being an entrepreneur is that you can only afford it if you’re independently wealthy, which usually means one of the following three conditions is true: 1) you’ve already had an exit with your previous company; 2) you’re so young you have no expenses because you couch-surf and eat noodles from Styrofoam; or 3) you’re supported by your spouse or parents. For me, it’s number 3. For the first couple of years of my startup, the fact that I wasn’t making a salary and contributing to household expenses was a major sore spot in my marriage. But then my husband had a sudden change of heart, and I give him enormous credit for that. He recognized that I’m doing what I love — my “life’s work” — and in doing so, I am truly, deeply happy. And no amount of money can buy your spouse’s happiness. There’s no greater gift I could receive from him than such heartfelt support, and I’m so grateful. I encourage every spouse out there — especially the husbands — to think long and hard about the tradeoff between money and happiness.

Crowley: Are you working on any exciting new projects now? How do you think that will help people?

Stillwell: I’m still working on Jumpstart! Our next major initiative will be to expand beyond earthquakes. Our goal is to get 2x to 10x more money into communities than the status quo, and as a benefit corporation, that’s our specific mandate.

Crowley: You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Stillwell: I would create a “know your neighbor” movement. “Neighbor” from the smallest sense of the word to the largest. There’s an epidemic of personal loneliness and isolation at this moment in history. Most of us live in cities, surrounded by thousands of other people every day, and yet many of us don’t even know our closest neighbors. We need to find more balance between the good aspects of urban anonymity, and the personal connections that humanize us. The first step would be to introduce yourself to your neighbors — say hi in the stairwell, go out for coffee, hold a small gathering, get to know the “back-stories.” As I’ve been getting to know the 84-year-old widow who lives two doors down, I’ve learned more about World War II than I ever did during school, hearing stories of what it was like to grow up as a child in London when there were air raids every night. It gives me more empathy for everyone who has survived wartime. Resilience is getting a lot of attention these days, but I think the next characteristic to be considered indispensable will be empathy. And it all starts with reaching out.

Crowley: Any parting words of wisdom that you would like to share?

Stillwell: We need to remain optimistic, even in the face of shocking setbacks. As entrepreneurs, we’re driving the future forward and are leaving a legacy behind. However, it’s never a straight line and there will be major bumps along the way. Always build a Plan B but remain positive and agile all the while.

Crowley: How can our readers follow you on social media?

TwitterLinkedIn

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