Personal blog of Yzmir Ramirez

It was easy to wonder what would become of Docker after it sold its enterprise business in 2019, but it regrouped last year as a cloud native container company focused on developers, and the new approach appears to be bearing fruit. Today, the company announced a $23 million Series B investment.

Tribe Capital led the round with participation from existing investors Benchmark and Insight Partners. Docker has now raised a total of $58 million including the $35 million investment it landed the same day it announced the deal with Mirantis.

To be sure, the company had a tempestuous 2019 when they changed CEOs twice, sold the enterprise division and looked to reestablish itself with a new strategy. While the pandemic made 2020 a trying time for everyone, Docker CEO Scott Johnston says that in spite of that, the strategy has begun to take shape.

“The results we think speak volumes. Not only was the strategy strong, but the execution of that strategy was strong as well,” Johnston told me. He indicated that the company added 1.7 million new developer registrations for the free version of the product for a total of more than 7.3 million registered users on the community edition.

As with any open-source project, the goal is to popularize the community project and turn a small percentage of those users into paying customers, but Docker’s problem prior to 2019 had been finding ways to do that. While he didn’t share specific numbers, Johnston indicated that annual recurring revenue (ARR) grew 170% last year, suggesting that they are beginning to convert more successfully.

Johnston says that’s because they have found a way to turn a certain class of developer in spite of a free version being available. “Yes, there’s a lot of upstream open-source technologies, and there are users that want to hammer together their own solutions. But we are also seeing these eight to 10 person ‘two-pizza teams’ who want to focus on building applications, and so they’re willing to pay for a service,” he said.

That open-source model tends to get the attention of investors because it comes with that built-in action at the top of the sales funnel. Tribe’s Arjun Sethi, whose firm led the investment, says his company actually was a Docker customer before investing in the company and sees a lot more growth potential.

“Tribe focuses on identifying N-of-1 companies — top-decile private tech firms that are exhibiting inflection points in their growth, with the potential to scale toward outsized outcomes with long-term venture capital. Docker fits squarely into this investment thesis [ … ],” Sethi said in a statement.

Johnston says as they look ahead post-pandemic, he’s learned a lot since his team moved out of the office last year. After surveying employees, they were surprised to learn that most have been happier working at home, having more time to spend with family, while taking away a grueling commute. As a result, he sees going virtual first, even after it’s safe to reopen offices.

That said, he is planning to offer a way to get teams together for in-person gatherings and a full company get-together once a year.

“We’ll be virtual first, but then with the savings of the real estate that we’re no longer paying for, we’re going to bring people together and make sure we have that social glue,” he said.

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The insurance industry, sleepy and ancient, is ripe for disruption. We’ve seen companies like Lemonade, Hippo and Rhino get in on that opportunity. Today, an insurtech company focused on small business insurance has raised $18 million to keep growing.

Meet Huckleberry, whose Series A was led by Tribe Capital, with participation from Amaranthine, Crosslink Capital and Uncork Capital.

Huckleberry launched in 2017 to offer business insurance, including workers’ compensation and general liability, all through an online portal.

Small business insurance coverage is not like car insurance or renters insurance. It’s not as simple as filling out a few forms and getting a quote. Even if a few platforms do have algorithms for providing quotes, you can’t really close the deal unless you get on the phone.

It’s an incredibly tedious and stressful process. In fact, Huckleberry co-founders Bryan O’Connell and Steve Au first came up with the idea for Huckleberry when they were seeking out their own small business coverage for a previous startup idea.

The industry itself is incredibly fragmented, which is caused in part by the fact that small business coverage underwriting varies wildly from business to business. For example, the policy for three or four restaurants might look relatively similar. However, a fast food restaurant might be identified as a higher risk with regards to workers’ compensation than a Michelin-star restaurant, where workers might be more eager to get back to work and take home their tip money. These differences come in the form of location, operations and many other factors, as well as business vertical.

Huckleberry has worked to build out myriad coverage verticals, including food and beverage, fitness, retail, legal, healthcare, hair and beauty and more.

The firm offers worker’s comp, as well as a package policy that includes general liability, property and business interruption insurance. Customers also can purchase add-ons like hired and non-owned auto insurance, employment practices liability insurance (EPLI), liquor liability insurance, employee dishonesty coverage, professional liability insurance, equipment breakdown coverage and spoilage coverage.

Huckleberry isn’t itself an insurance carrier, but does have the authority to underwrite and sell policies on behalf of the carrier. That said, Huckleberry’s expansion both by vertical and geography is more difficult than your average software startup. The regulatory landscape of insurance in the U.S. goes state by state.

“Our biggest challenge is navigating 50 states’ worth of extremely complicated regulations on something that is much more complicated than a software product,” said O’Connell. “We’re trying to protect individual workers and businesses all while staying fully compliant in every market.”