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Insurtech’s big year gets bigger as Metromile looks to go public

In the wake of insurtech unicorn Root’s IPO, it felt safe to say that the big transactions for the insurance technology startup space were done for the year.

After all, 2020 had been a big one for the broad category, with insurtech marketplaces raising lots, rental insurance startup Lemonade going public, Root itself debuting even more recently on the back of its automotive insurance business, a big round to help Hippo keep building its homeowners company and more.


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But yesterday brought with it even more news: Metromile, a startup competing in the auto insurance market, is going public via a blank-check company (SPAC), and Hippo raised a huge, unpriced round.

So let’s talk about why Metromile might be plying the public markets, and why Hippo may have have decided to pick up more cash. Hint: The reasons are related.

A market hungry for growth

The Lemonade IPO was a key moment for neoinsurance startups, a key part of the broader insurtech space. When the rental insurance provider went public, it helped set the tone for public exit valuations for companies of its type: fast-growing insurance companies with slick consumer brands, improving economics, a tech twist and stiff losses.

For the Roots and Metromiles and Hippos, it was an important moment.

So, when Lemonade raised its IPO range, and then traded sharply higher after its debut, it boded well for its private comps. Not that rental insurance and auto insurance or homeowners insurance are the same thing. They very most decidedly are not, but Lemonade’s IPO demonstrated that private investors were correct to bet generally on the collection of startups, because when they reached IPO-scale, they had something that public investors wanted.

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Pay-per-mile auto insurer Metromile is heading to public markets via SPAC

Metromile, the pay-per-mile auto insurer that earlier this year laid off a third of its staff due to economic uncertainties caused by COVID-19, is taking the SPAC path to the public markets.

The company, which was founded in 2011 and is led by CEO Dan Preston, said it has reached a merger agreement with special purpose acquisition company INSU Acquisition Corp. II, with an equity valuation of $1.3 billion.

Metromile said it was able to raise $160 million in private investment in public equity, or PIPE, in an investment round led by Chamath Palihapitiya’s firm Social Capital. Existing investors Hudson Structured Capital Management and Mark Cuban, as well as new backers Miller Value and Clearbridge participated. Metromile will have about $294 million of cash at closing.

The company plans to use those proceeds to reduce existing debt and accelerate growth, specifically to hire employees to support its consumer insurance and enterprise businesses, and grow beyond its eight-state geographic footprint to a goal of 21 states by the end of next year and nationwide coverage by the end of 2022.

Metromile is credited for disrupting some of the inefficiencies of the auto insurance business model, notably how consumers are charged. Instead of a standard flat fee, Metromile charges customers based on their mileage, which it is able to measure via a device plugged into the vehicle. Some two-thirds of U.S. drivers are considered low-mileage, according to Metromile. By charging per mile, Metromile says its customers save 47% on average compared to their previous insurer.

The company developed a mobile app, which besides allowing users to file claims, offers other features such as alerting the driver of possible parking violations due to street sweeping activity. Now, with three billion miles of driver data, the company is able to make predictive models that help lower customer costs and improve their overall experience.

The company also built out an enterprise division in 2019 that offers a cloud-based software as a service to large legacy insurers. Metromile licenses components of its platform, including claims automation and fraud detection tools.

The COVID-19 pandemic created initial headwinds for Metromile, which had been one of the fastest-growing startups in the Bay Area. Metromile ended up laying off about 100 people as it aimed to pare back its workforce. The company said at the time that its business was affected by pandemic-related stay-at-home orders, which caused its customers to drive less. The pandemic also prompted U.S. drivers to shop around for insurance and look for deals that supported their shift to lower mileage.

Investor Cuban said in the company’s SPAC announcement sees an upside for the business.

“During these times of financial hardship, unemployment and work from home, Metromile provides an important insurance alternative,” Cuban said. “The option to pay for insurance by the mile is a game changer and why I’m incredibly excited about Metromile’s future!”

Social Capital’s Palihapitiya is equally bullish on the company, tweeting Tuesday “Buffett had Geico. I pick @Metromile.”

Metromile has hired back staff and returned employees that it placed on furlough this spring. Today, the company has more than 230 employees and doesn’t expect any reductions in the workforce in the future. Instead, the company told TechCrunch it plans to hire additional staff on the expectation that both its consumer and enterprise businesses will grow “considerably” in the next few years.

The transaction is expected to close in the first quarter of 2021. The combined company will be named Metromile Inc., and is expected to remain listed on NASDAQ under the new ticker symbol “MLE.”

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3 lessons from Root’s IPO pricing

Last night neo-insurance provider and former startup Root priced its IPO at $27 per share, $2 per share ahead of its $22 to $25 target price range.

According to Root, it sold 26,830,845 shares in its IPO, including 24,249,330 from the company itself. Its underwriting banks have the option to buy another 4,024,626 at the IPO price, less “underwriting discounts and commissions.” The remaining shares are being sold by existing shareholders.

At $27 per share, Root raised $654,731,910, but that figure will rise to $763,396,812 if its underwriters exercise their option in full, using the full $27 price for our calculation. Per its S-1 filings, both Dragoneer and Silver Lake will purchase $250 million of Root stock at the IPO price once the IPO has closed.


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Root will therefore raise north of $1 billion in its IPO, once all shares sold are counted. Doing some loose math, Root is worth around $6.8 billion at its IPO price, though Renaissance Capital, an IPO specialist, puts the figure at $7.1 billion on a fully diluted basis.

For the Midwest, Ohio-based Root’s IPO is a win. The company shows that it is possible to build high-growth technology companies worth billions of dollars far from coastal hubs. For the broader insurtech space, Root’s IPO is a win. The company follows Lemonade to the public markets, setting a strong valuation mark again for the neo-insurance startup market.

For similar companies like Clearcover, MetroMile and all startups that related to Root and Lemonade, it’s a good day. Let’s get into what we can learn from Root’s pricing.

Three lessons

Insurance multiples are hot. Key from Root’s IPO is the fact that we can now see insurance revenue being treated similarly to software revenue. How so? In multiples terms. Let me explain.

Root generated $245.4 million in revenue during the first and second quarters of 2020. That’s a run rate of around $491 million. At $7 billion, that’s a 14x revenue multiple. For an insurance provider with scant gross margins! Wild. Given Root’s weak-looking Q3 2020 revenues, that number isn’t going to fall anytime soon.

For companies that are not pure-play software outfits and want to go public, Root’s strong, above-range pricing makes it plain that there is investor demand for more than one type of revenue growth.

Investors are betting that Root’s history of growth will continue. In the first half of 2019, the company’s revenues were a mere 42% of what it pulled off during the same period in 2020. If the company can more than double again next year, then, hey, maybe all the numbers work. But to see public shareholders take such a growth-and-valuation flyer on an insurtech player is notable.

Kyle Nakatsuji, co-founder and CEO of Clearcover, another neo-insurance provider, explained to TechCrunch via email what he thinks is going on: “It’s clear that the market is aware of the massive opportunity for technology-enabled disruption in the category and it is rewarding those companies that focus on customer-oriented, digital innovation. The rapid growth of key players in the space is now proving this will play out and the winners will be consumers seeing lower prices and investors seeing better returns.
”

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Root targets $6B+ valuation in pending IPO, a boon for insurtech startups

This morning Root Insurance, a neoinsurance provider that has attracted ample private capital for its auto-insurance business, is targeting a valuation of as much as $6.34 billion in its pending IPO.

The former startup follows insurtech leader Lemonade to the public markets during a year in which IPOs have been well-received by investors focused more on growth than profitability. In the wake of Lemonade’s strong public offering and rich revenue multiples, it was not impossible to see another, similar startup test the same waters.

Root’s $6.34 billion valuation upper limit at its current price range matches expectations for its bulk. The company is targeting $22 to $25 per share in its debut.

The startup will raise over $500 million from the shares it is selling in its regular offering. Concurrent placements worth $500 million from Dragoneer and Silver Lake raise that figure to north of $1 billion and could help boost general demand for shares in the company. Snowflake’s epic IPO came with similar private placements from well-known investors in what became the transaction of the year.

Will we see Root boost its target? And what does Root’s IPO price range mean for insurtech startups? Let’s dig into the numbers.

Root’s numbers

We’ve dug into Root’s business a few times now, both before and after it formally filed its IPO documents. This morning we will merge both sets of work, snag a fresh revenue multiple from Lemonade, apply it to Root’s own numbers, observe any valuation deficit and ask ourselves what’s next for the debuting company.

Will we see Root’s IPO price rise? Here’s how to think about the question:

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As tech stocks dip, is insurtech startup Root targeting an IPO?

During the week’s news cycle one particular bit of reporting slipped under our radar: Root Insurance is tipped by Reuters to be prepping an IPO that could value the neo-insurance provider at around $6 billion.

Coming after two 2020 insurtech IPOs, Root’s steps toward the public markets are not surprising. But they are good news all the same for a number of insurance startups that have raised lots of capital and will eventually need to prepare their own debuts if they don’t find a larger corporate home.


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Programming note: The Exchange column is off starting tomorrow through next week. The newsletter will go out as always on Saturdays. I’m taking a week to sit and do nothing.

The Root IPO will also help clarify Lemonade’s own public offering and ensuing valuation. Lemonade’s debut brought a strong price to the rental-focused insurance provider, leading to a more buoyant attitude toward the valuation of its class of startups. More precisely, the public price assigned to Lemonade when it floated was, no bullshit, very bullish.

If Root can repeat the feat it would cast a warm light on the yet-private players in its niche that will have their eyes pinned to the flotation. Names like MetroMile and Hippo could be next if Root’s IPO goes well.

But, first, does Root make sense at a $6 billion valuation? We can do a little digging on that this morning, using Lemonade’s present-day valuation to get a handle on the figure. Let’s go!

Root’s valuation in a Lemonade world

Before we get into the numbers, bear in mind that we’re going to compare apples and oranges today, and that we’ll have to use some dated numbers as well. That said, we can still get somewhere about what Root could be worth. So, roll with me but don’t take every number as engraved onto an obelisk.

Back in July of this year, in the wake of the Lemonade IPO and Hippo’s latest funding round, a $150 million investment at a $1.5 billion post-money valuation, we started to do some math. Lemonade’s valuation was much richer than Hippos’ when you look at their multiples, which got us thinking about private and public neo-insurance provider valuations: Why was Lemonade worth so much more than its peers per dollar of written premium?

To better understand the situation, we dug up some 2019 data on the dollar value of gross written premium Hippo and Lemonade wrote and found new valuation multiples for them based on those numbers. Lemonade was worth 28.4x its Q1 annualized gross written premium, while Hippo was worth just 5.6x its own.

Then we also found Root and MetroMile gross written premium numbers for 2019, which allowed us to calculate their own effective valuations (albeit using dated numbers).

As before when we found that Hippo’s private valuation looked light compared to Lemonade’s public valuation when we contrasted their valuation/gross written premium multiple, we discovered that MetroMile and Root also looked cheap. Very cheap.

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Are insurtech startups undervalued?

On the heels of Hippo’s funding round and our exploration of how the private markets appear to be more conservative than public investors at the moment, we’re asking a new question: are a bunch of insurtech startups undervalued?

Hippo — an insurtech startup focused on home insurance — put together a $150 million round at a $1.5 billion post-money valuation after growing its gross written premium to $270 million “in the past 12 months.” At that valuation, and at pre-adjustment premium scale, Hippo is super-cheap compared to Lemonade, another venture-backed insurtech startup that just went public.


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There’s no need to relitigate Hippo’s valuation and how the private markets have valued the firm. But our work yesterday does give us the chance to do some fun math on other players in the neo-insurance space, namely, Root and MetroMile. Using data accrued from financial filings and valuation data from Pitchbook and Crunchbase, we can grok how much the two firms are worth using Hippo’s and Lemonade’s current premium multiples.

If you aren’t familiar, the cohort of startups we’re looking at have raised well over $1 billion as a group; VCs really believe in them. How they are priced then, and how they exit, will help determine the results of many a venture fund.

So, are other players in the startup insurance market cheap at their last private price when compared to Lemonade and Hippo? Did their venture backers overpay? Let’s find out.

Cheap? Expensive?

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As 5 more startups join the $100M club, are we just making a pre-IPO list?

Hello and welcome back to our regular morning look at private companies, public markets and the gray space in between.

Today we’re adding five names to the $100 million annual recurring revenue (ARR) club and listing all preceding members in a single post. This series, which was a bit of an accident, if I’m being honest, has included more than a dozen companies that have reached $100 million ARR, along with a handful more that are close.

Today we’re adding Seismic, ThoughtSpot, Noom, Riskified and Moveable Ink to the list. As always, we have funding histories, growth metrics and interviews below on the new group. But at this juncture, as we head toward the two-dozen company mark, it’s a good time to ask, what is this list that we’re compiling?

At first, the goal of the jokingly-named “$100 million ARR club” was to highlight companies that were of real scale, an idea designed to gently push back against the “unicorn” moniker. As more and more unicorns were born and the private-capital world became adept at getting startups of all maturity levels over the requisite $1 billion valuation threshold, the term began to feel too diluted to have much signaling value.

While, in contrast, $100 million in ARR felt much more “hard” to the valuation metric’s comparable squishiness. But, since that first post, more and more companies have written in, sharing hard metrics and the series has continued. Perhaps we’re really just compiling an IPO watchlist, a grouping of firms that will probably go (or should go) public in the next 18 months.

Let’s dig into our new additions. Then, we’ll list all our prior entrants with links to our preceding coverage in case you are playing catch up. With that, here’s the entire $100 million ARR club a list of companies that we think could go public inside the next six quarters.

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Optimizely raises $50M Series D round for its experimentation platform

Optimizely, a platform that offers tools for A/B testing and personalization on the web and in mobile apps, today announced that it has raised a total of $105 million. This includes a $50 million Series D round led by Goldman Sachs Private Capital, with the participation of Accenture Ventures, as well as a $55 million line of credit from Bridge Bank.

Goldman Sachs’s Michael Kondoleon will join Optimizely’s board of directors as a board member.

“We’re excited to reach this milestone because these investments cement our leadership position in the market,” Optimizely CEO Jay Larson told me. “We can invest more in products to put an even bigger gap between Optimizely and our competition. We can expand geographically. And we will continue to grow our team of world-class digital optimization experts. This is a big day for Optimizely and a big day for the experimentation and personalization industry.”

The company notes that about a quarter of the Fortune 100 currently use its services. The company says it now handles more than 6 billion events a day and that its customers have tripled their investments in digital experience optimization in the last two years. Current customers include the likes of Gap, Visa, IBM, StubHub, Metromile, Lending Club and Sonos.

In total, Optimizely has now raised more than $200 million, excluding the line of credit. The additional $55 million from Bridge Bank is a bit unusual, but not completely out of the ordinary for companies at this stage. “Bridge Bank is proud to continue working with Optimizely, a global leader at the forefront of the digital experience optimization market,” said Mike Lederman, senior vice president and western region director of Bridge Bank’s technology banking group. “Optimizely is on a path of substantial growth and the additional capital will help them continue to build market-leading products that are used by an increasing number of top global brands.”

As is pretty much standard for companies at this stage, Optimizely will use the new funding to drive growth.

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Startups want to change what you insure and how you insure it

 In an insurer’s ideal world, there’d be a profitable policy for every conceivable risk. Click once, and you’re covered. But in the real world, insurance hasn’t kept up with the changes of recent years. The millennial generation has entered adulthood intent on completing — online — any complex transaction in a couple of minutes. But insurance policies look… Read More

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