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Stuart Winchester: One of the Things That Brings Me Real True Joy Is Building Teams and Then Working as Part of Them

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Stuart Winchester

Stuart Winchester of Marble.

Tell us about yourself?

Stuart founded Marble in December 2019. Previously he worked as the General Manager, Insurance Product at Better.com, where he launched and led the company’s insurance practice, Better Cover. Stuart joined Better as the Director of Revenue, helping position Better for a successful $160MM Series C. Before this, Stuart worked as the Senior Manager and Interim General Manager for General Assembly’s flagship New York campus, leading a key turnaround across marketing, operations, sales, and student outcomes ahead of General Assembly’s successful exit via acquisition by the Adecco Group. Stuart started his career as a member of the founding team at Accordion, helping to grow the company from start-up consultancy to established portfolio operations partner to top global private equity firm. He is a graduate of Trinity College, Dublin University.

What do you think is the single biggest misconception people have when it comes to startups?

You can do one thing well and succeed. There’s a lot of popular literature and social media commentary that may give a soon-to-be founder the impression that, at the earliest stages, showing one or two great metrics or features will open the growth and fundraising spigot. This isn’t really the case — expectations are super high, both from users and investors, and you really need to have a cohesive and impressive story nailed down across every dimension (product, growth, fundraising, hiring, etc). The bar is high, as it should be!

If you could go back in time to any moment from your journey, and give yourself one tip, what would it be?

I would have slapped myself the moment I spent more than 20 seconds thinking about what domain name to buy.

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What makes you stand out as an entrepreneur?

One of the things that brings me real true joy is building teams and then working as part of them. From a brass tacks perspective I hope that investors, partners, and employees can see from my background that I have built and managed fairly critical teams at a few dynamic businesses. But really that’s just what I love to do, build teams, and I think I do it well.

What are some of the best working habits you’ve gained over the past couple of years?

At Marble we follow a pretty consistent, if somewhat flexible, format when it comes to writing up our work, ideas, blockers, or really describing anything we need a teammate to look at. The ability to quickly and thoroughly communicate an idea with a teammate who may not have much context is a real sign of respect and builds tremendous velocity and autonomy.

Give us a bit of an insight into the influences behind the company?

I spent a number of years building and running the insurance vertical at Better.com. In this seat, I saw a huge gap between how American consumers were able to interact and take control of their personal finances, compared to how little control they had over their insurance and risk. The digital landscape of insurance tools at the time (2019) were very siloed (i.e. carrier specific mobiles apps) or only optimized for distribution (i.e. online insurance aggregators/agencies). There was no solution that digitally unified every piece of risk and insurance in the household, and no insurance platform that offered much value besides “buy buy buy.”

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At the same time, I started to explore the opportunity to redirect the massive amount of insurance advertising dollars into a rewards program that would provide value directly to consumers for protecting what they love. With these two concepts: Single source of truth for all the risk and protection in your household, and rewards instead of Super Bowl ads, we started building Marble so you can earn rewards for protecting what you love.

Where do you see your business in five years?

Marble will be the personal insurance operating system for millions of American households. With one secure, beautiful account to manage every insurance policy, shop and lower your rates, add new coverages, make all your payments, track local weather risks, and view risk data from our integrations with telematics and wearables brands, Marble will be the one stop for millions of insured Americans.

What do you think the biggest challenge will be for you in getting there?

Insurance technology as a category is a few years behind the rest of fintech. We’re finding that we have to build a lot of what our customers want from scratch, which takes time. So, I think time will be our biggest challenge.

Talk to us about your biggest success story so far?

I’m most proud of our Ambassador program. We have well over a hundred Marble members who are so invested in the future of our platform that they contribute dozens and dozens of amazing ideas on a private request board. They also spend lots of time sharing feedback with our Product team.

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For such an early stage company, operating in a space like insurance, I’m thrilled that we are able to build a community like this.

How do clients and customers find you? Are you much of a salesperson for yourself?

People find us through our partner relationships, or just online generally, or most commonly via referral from another Marble member. 1 in 4 Marble members refer multiple other members which makes this all really fun. And I’m not sure if I’m “much” of a salesperson but if you’re a founder, you have to be!

What one tip would you give to fellow startup founders?

Take the money. As much as you can get and whenever you can get it. You may have people in your ear talking about strategic considerations from taking capital from so-and-so, but your most fundamental objective as an early stage founder is: Make sure your team can get up and fight again tomorrow. You’ll need plenty of cash to do that.

And finally, what do you hope the future brings both you personally, and your business?

I’d like my family to be healthy and I’d like for my business to keep providing opportunities for great people to flex and show off and build useful stuff.

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