Instant Everything. Killer Prices. Big Heart: A Conversation With Lemonade’s CEO

Insurtech is a booming field, with startups rushing to innovate one of the nation’s most important industries. These are not your mama’s insurers. Instead, they use technology to make sure you get the best prices available to you.

You no longer have to pick up the phone and talk to an agent to take out a new policy. Just input some information into a web tool and, in minutes, you’ll have a quote for a new policy.

But some companies are revolutionizing the field, and one of those companies is Lemonade.

We recently sat down with Lemonade’s CEO, Daniel Schreiber, to discuss all the ways Lemonade is different from other insurers.

Why Lemonade?

Do you know how much you’re paying your insurer in fees?

Lemonade policy holders do.

Instead of disguising those fees while quoting a fixed rate for premiums, Lemonade takes a flat fee of each premium. That money is used for operating expenses.

What if those expenses don’t use up the full flat fee? Lemonade doesn’t pocket the money. Instead, the remainder is donated to charity.

The entire process, from start to finish, is built for ease of use. You can apply in minutes and, if you ever have to file a claim, that process is quick, as well, with payment issued quickly.

Once you’ve learned a little more about Daniel Schreiber, you’ll understand Lemonade’s slogan,

“Instant Everything. Killer prices. Big heart.”

If you’ve ever used a Powermat to charge your phone, you’re already familiar with Daniel Schreiber’s work. Daniel served as president of Powermat for the few years prior to joining Lemonade. During that time, the company expanded its innovative phone-charging technology until it became a standard feature in much of the technology used today.

Instant Everything. Killer Prices. Big Heart: A Conversation With Lemonade’s CEO - Daniel and Shai

Along with Shai Wininger, co-founder of Fiverr, Daniel founded Lemonade in 2015 with the goal of transforming the insurance industry. Daniel and Shai have always led with the mission to help transform insurance into a customer-friendly, technology-first industry.

Money Under 30’s interview with Daniel Schreiber

MU30: We’d love to hear more in-depth about how, when, and why you started Lemonade. Share with us more about the origins, beginnings, and the inspiration for Lemonade.

DS: Both Shai (Wininger, my co-founder) and I are veterans of the tech ecosystem and knew nothing about insurance when we first started. It’s precisely that outlier, tech-focused perspective that we brought to the insurance industry.

One of the factors that stood out most to us when building Lemonade was the lack of transparency and conflicted interests. We continued to ask each other, “Why can’t insurance be transparent?” It was mind-boggling that an industry that is performing such an important societal role is perceived so negatively.

Insurance fraud is a serious symptom of this.

That’s why we made transparency and overcoming conflicts of interest a significant pillar of Lemonade. 

MU30: What would you say to a Millennial who says that they simply don’t need insurance – that they’d rather save the money each month/year? That is, what is the best way to convince someone who does not have insurance that they should get insurance?

DS: I’d leave that to our Chief Behavioral Officer, Prof. Dan Ariely, who is a world-renowned expert on the irrational decisions we make all the time.

Specifically, for insurance, nobody really thinks of getting insurance as a delightful event or to-do task to check off your list. Dan explains that it’s so difficult to put our long-term goals first because we often let our ‘pebbles’ get in the way of our ‘big rocks.’

‘Pebbles’ are small tasks that come our way every day, while ‘big rocks’ symbolize long-term goals, such as planning our family’s future, paying taxes, making financial plans, taking care of our health, and getting ready to move apartments.

If our week was a glass jar, we could easily fill these jars with every pebble, grain, and small rock that comes our way. Without realizing, our jar would be full before there is any room for the ‘big rocks’ that are important to us.

But Dan says the best way to prioritize your long-term tasks (like getting covered for a rainy day bad luck situation) is to set aside time to achieve our ‘big rocks.’ Let’s say you’ve been putting off the task of purchasing insurance for your new apartment. This task has been sitting on your to-do list for months, but you haven’t found the inspiration to actually get it done. But, in fact, chances are you’d feel much more at ease in the long run if you did not wait for a “muse” – or a burglar – to motivate you to protect your things.

If we simply set aside the time to achieve our ‘big rocks,’ we’ll be sure to thank ourselves one day. Taking steps to plan for our future can bring a sense of reward when we least expect it, and will also help us finally feel a greater sense of accomplishment at the end of our busy week.

MU30: What is the most misunderstood part about the world of insurance that you wish you could clarify once and for all?

DS: Not all insurance companies are built the same. Both traditional insurers and ‘insurtech’ companies could be considered competitors, but Lemonade is unique in that we view ourselves as a tech company doing insurance, and not the other way around.

This mindset allows us to iterate fast. Our engineers can code algorithms into our app on the go, our product managers can design features overnight. It’s precisely this agility that the traditional insurance industry struggles with.

Having said that, it’s clear that the incumbents are aware of the need to change, and become, at the very least, more customer-centric. We’re seeing quite a few carriers ‘digitize’ part of the insurance process, but the infrastructure and business model is the same, centuries-old framework. It’s genuinely hard to innovate under those conditions.

MU30: Lemonade is covered in 20+ states and the District of Columbia, and is coming soon to many other states. What have been some of the challenges of expanding across the United States, Germany, and now the Netherlands?

DS: As a fully licensed and regulated insurance carrier, we have to work with 51 different regulators in the US (50 states plus DC) and the EU has, of course, its own regulator, as well.

So while it’s been a more challenging road to pursue, becoming an insurance company (rather than an agent or broker) means being able to innovate from the ground up.

It has been a pleasure working hand in glove with all state regulators, and especially our ‘domicile state’ – New York. We chose to first launch in New York as it’s arguably the financial capital of the world and known to be a demanding regulator. We reasoned that if you can make it in NY, you can make it anywhere.

MU30: Your motto is that Lemonade is “Insurance powered by AI and driven by social good.” How do you decide which organizations should be on the list? And we know that you have the option to send in names of organizations – do people send in names frequently?

DS: Absolutely. As a data-driven organization built on transparency, we want to work with charities that know the impact of every dollar. So we work with a plethora of like-minded nonprofits who are data-driven but also know how to measure and communicate their impact.

Our customers constantly email us to recommend charities to partner with, so much of our Giveback partners today have come from the Lemonade community themselves. It’s been incredible to watch our community grow and make a significant impact: just last year the community gave back more than $630K to 26 charities they chose.

MU30: What are the limits to AI that Lemonade is still hoping to improve in the coming year?

DS: We’d believe AI can get even better at handling all kinds of things humans do today, and in so doing it can slash costs, while increasing customer satisfaction by removing wait times and hassle. All the while, AI and big data can help us get ever better at ensuring our customers have the right coverages for them, and that we are charging them a rate that matches what they need.

MU30: What is the future of the insurance industry and how do you see Lemonade changing in the next few years to be leaders in that change?

DS: It’s going to be a different, tech-heavy landscape. Insurtech is an extremely trendy field right now, and the rapid technological changes will impact every aspect of the insurance industry. The industry went largely untouched by technology for more than a century, and the incumbents, together with technology companies, are starting to accelerate innovation within their organizations, investing in insurance startups, and digitizing a lot of their operations.

Technology – and innovating on that technology constantly – is compulsory to survive. Lemonade is working – together with regulators – towards a future built on big data and AI.


With Lemonade, Daniel Schreiber is proving that technology can revolutionize traditional business models. In the coming years, consumers will see artificial intelligence playing more of a role in insurance – both in the way policies are issued and managed.

But perhaps the most important change Lemonade is bringing to the industry is customer friendliness. By making a commitment to provide transparent pricing and personalized service, Lemonade is winning over customers who never realized insurance could be so easy.

Money Under 30 thanks Daniel Schreiber for taking the time to talk to us about the future of the insurance industry. We’re excited to see how the industry will continue to evolve.

Learn more about Lemonade or read our Lemonade review here.

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