Sherpa founder Chris Kaye

SXSW Startups: Sherpa

The Forrest Four-Cast: February 25, 2019

Hugh Forrest
Published in
5 min readFeb 26, 2019

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Fifty diverse startups will aim to impress a panel of judges and a live audience with their skills, creativity and innovation at SXSW Pitch Presented by Cyndx. Winners in 10 categories will be announced at the Pitch Award Ceremony at 6:30 pm Sunday, March 10, at the Hilton Austin.

A finalist in Artificial Intelligence, which pitches at 11 am Sunday, March 10, the London-based Sherpa is a personal insurance solution for the world’s fastest growing workforce: the self-employed. First in the world to use a proprietary AI algorithm, the company is able to assess risk, lifestyle and requirements, and using a universal risk score, provide a tailored, unbiased (with zero commission) recommendation on the best insurance plan. Sherpa’s mission is to make insurance simpler, and accessible and affordable for entrepreneurs, freelancers, and contractors.

Co-founder Chris Kaye talked about his company’s plans and experience.

What’s one piece of advice you wish you’d had that you’d give to others wanting to join the startup journey?
Invest in your own health and well-being as your number one priority, as this is going to be an exhausting Iron Man — and sleep!

What is your competitive advantage?
We have built a new model for insurance that is more convenient (10 minutes vs. 10 days), more accurate and adaptable, and more affordable (20 to 40 percent more for most members).

However, our real competitive advantage is trust. We have built trust into the way we make money. Our monthly membership fee is transparent. It is a flat fee, so it doesn’t depend on how much insurance you buy. And it is paid by the member — not an insurer — so there is never ANY doubt about who we are working for.

What are your goals for Sherpa in 2019?
We are proud to be launching an important and groundbreaking new proposition at SXSW and begin our global rollout. In addition, we are scaling up our U.K. business for the self-employed, adding more risks to the Sherpa platform so that we can cover more needs. And, of course, we will be fundraising — looking to close our Series A at or shortly after SXSW.

Currently one in seven of the U.K. workforce is self-employed. This number is predicted to rise as Brexit moves forward. How do you expect this to influence the British insurance market?
Financial services and insurance in particular haven’t shown a lot of love for the self-employed. Our members have gone through the process of clicking “self-employed” on a mortgage or insurance application form, knowing the road ahead is going to be difficult. The government and providers need to acknowledge the five million (and growing) self-employed and keep up with the new world order, whose insurance needs aren’t being met. This is in addition to tax codes, credit scoring, underwriting rules, which all need to be adapted for this workforce. Brexit is a massive distraction, and it is our opinion that the government needs to focus on what’s actually important — making the fastest growing and most dynamic workforce more effective and productive.

How does a Sherpa customer know that their personal information is safe?
Our mantra is that we only use your data to help you. We live and die by the customer’s trust, in what we do with their data. One of the reasons I set up Sherpa was because I never wanted to give an insurance company access to my Fitbit, bank data, or location data. We created Sherpa as an interface between the consumer and the insurance industry. We keep your data safe with bank-level security. You can access it or wipe it at any time. We seek your explicit permission to hand over the minimal amount required to buy you the insurance you need.

Has Sherpa been involved with other pitch events and tech conference?
We are very proud to have been award winners and finalists at DIA in Amsterdam, TOA in Berlin, and MIT’s Inclusive Innovation awards in Europe. SXSW is our first outing in the U.S., and on a whole different scale to these European conferences. We have learned that you need to well-organized, passionate and willing to take a risk!

Tell us about the startup ecosystem in London.
London has a fantastic startup ecosystem, particularly for FinTech and Insurtech. As one of the major global financial centers, London has a great combination of in-depth financial and technical expertise. As the biggest entrepreneurial center in Europe, it is a hive for creativity, funding options, tech talent, and partnership opportunities.

Which tech trend is your team most excited about?
We are super excited about the advance of robotics, combined with AI, to genuinely move us towards the potential for intelligent androids. This felt 20 years away three years ago, and now feels only two to three years away.

Looking at the entire tech industry, what technology would you call the Myspace of 2019…in other words, something we won’t be thinking so much about in 2020 and beyond?
I think you need failures in technology so that successes can rise, phoenix-like, from the ashes. I believe cryptocurrency will die, but distributed ledger tech will be the big beneficiary from the investment in the underlying infrastructure.

What do you enjoy most and least about the startup experience?
I love and hate the roller coaster of startup life in equal measure. The excitement, constant change, thrill of success is as visceral as the despair, frustration, and lack of time. But wouldn’t change it for the world!

What has the startup experience taught you about life?
Investing in people and relationships will have the biggest payoff, both professionally and personally.

Name three people, in any field, alive or dead, you’d like to meet and tell us why.
Ernest Shackleton
— how on earth do you motivate a team through such incredible circumstances, and just keep going, despite all the odds — that’s leadership!
Sir David Attenborough — I admire his ability to find beauty and wonder in the world around us, and his indefatigable desire to share that with the rest of us, well into his 90’s — that’s passion!
Aristotle — someone who was dedicated to the search for unknowable answers to life’s biggest questions, still a reference point 2,500 years later — that’s lasting impact!

Look for more interviews with other SXSW Pitch finalists in this space between now and March.

Click here to see all 50 finalists for SXSW Pitch 2019, along with the links to their interviews on Medium.

Also, if you are an entrepreneur, check out all the cool panels and presentations in the Entrepreneurship and Startups Track, which runs March 8–12 at SXSW.

Hugh Forrest serves as Chief Programming Officer at SXSW, the world’s most unique gathering of creative professionals. He also tries to write at least four paragraphs per day on Medium. These posts often cover tech-related trends; other times they focus on books, pop culture, sports and other current events.

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Celebrating creativity at SXSW. Also, reading reading reading, the Boston Red Sox, good food, exercise when possible and sleep sleep sleep.