Started as a 'Project'...Now We're Here: Announcing Boost's $20M Series B wanted more blogs, huh?

Pretty soon, I’ll be relegated to being one of those perma-blogger/Twitter founders in order to add some value around here, so I’d better step up my blog game. The good news is that it’s been well over a year since my last post, and that was an absolutely insane year, so it’s well past time for about 2,000 words of catching up.

To those of you who asked for more blogs, just remember that you literally asked for this. To those of you who don’t care, feel free to read something even more clickbait-y.

Sure, I could take that personally...but why bother? ;)


  • $20M Series B led by RRE Ventures with FinVC, an amazing global reinsurer we couldn’t announce publicly (mysterious, huh?), and a few other new and friendly faces (Press Release!)
  • >10x customer growth (Join Us!), 6+ proprietary products (Products!), and the best API platform in the game (API Docs!)
  • How a ‘Project Boost’ PowerPoint transformed into a leading fintech (Spoiler: Our Team!)
  • More capital means more fuel for our mission – to not just improve the way insurance is purchased by consumers, but to fundamentally change how assets and risks are transferred across the insurance marketplace

Now, let’s get started...

What a difference a year or two makes, huh?

Boy, does it feel good to say this…

Today, I’m thrilled to announce the close of Boost’s $20M Series B, led by RRE Ventures with participation from FinVC, Gaingels, Hack VC, along with a strategic investment from a leading global reinsurer (bet you wanna know, huh?). I couldn’t be happier to welcome this group to the party, and we’re all incredibly grateful for the continued support from our longtime partners Greycroft, Coatue, Conversion Capital, and MetLife’s Chairman Glenn Hubbard.

Not only is that a Murderers’ Row of a cap table, but these investors also don’t just express their conviction about their investments - they actually work to help build and grow their portfolio companies. Like, for real. It’s awesome.

30+ employees, dozens of amazing insurtech and embedded partners, a tech platform that has expanded almost as fast as my BMI during Covid. Now, to top it all off, a $20M Series B with a group of amazing investors to give Boost one heck of a…boost (okay, I know, that was terrible).

Wait, back up, who is Boost and what do you do?

We make it simple for any company to build, launch, and manage insurance programs, and then offer those solutions to their customers through a fully embedded digital experience. Boost follows in the footsteps of companies like Plaid, Affirm, and my personal favorite Marqeta.[1]

Back when they were getting started (call it 2010-2015), these now-Goliath fintech leaders were transforming the fintech landscape by providing picks and shovels for innovative companies across all segments. We now recognize what they were creating as “Fintech Infrastructure” or “X-as-a-Service” or “Embedded Finance.” That approach will drive significant value to insurance as well – and that’s where Boost lives.

Screen Shot 2021-05-19 at 8.08.05 PM (1)

Boost’s platform is built to power this fintech revolution for insurance. We’re the picks and shovels of insurtech, we live in the background of our clients’ businesses, and we like it that way. If you want to learn more about Boost, you can get familiar with our company here, our API here, or just reach out here.

or, just read on for some more hot air from its founder. Your pick.

Okay, first things first, Boost would still be a ‘Project’ without this incredible team…

As I said, there are now 30+ incredibly talented people building this Boost machine – and we are on-track to at least double that number over the next 12 months. That’s a surreal thing to be part of, and holy hell, is it exciting. Our team is one of the few things that I’ll shamelessly take some credit for, because helping with its assembly, development, and growth is my proudest professional achievement – like, by a mile.

Boost-SeriesB-ThumbsUp (1)

By far, the most instrumental part of Boost’s success has been the people (way smarter than me) who’ve jumped in to build what was effectively a fever dream. And they’re not crazy, they’re confident. The people I have the privilege of working with every day at Boost are at the top of their respective fields, and they’ve traded comfort and security for this extreme challenge, because they want to build something special, and they know that something special is Boost.

Even I’m not crazy enough to diminish how risky that decision was for all of them, and their families. Holding up my end of the bargain for my team is the only thing that ever keeps me up at night. I’m eternally grateful to each and every one of them.

That’s why today’s announcement and any celebration around it isn’t about me, or our investors, or any APIs or buzz words – it’s about this incredible group of people on the Boost team who have literally built Boost from the ground up, day in and day out, for nearly five years now.

Today isn’t just about them. It’s because of them. They’re the ones who built this and they did it all the hard way – because it was the right way…

Let me tell ya, building this the hard way was REALLY painful in the early days – but boy is it paying off now…

Over the last 18 months, Boost has transformed in such a massive way, and it has been absolutely incredible watching this team execute. Not too long ago, we were still mostly an early-stage startup with a huge idea, on a mission that was still just “a little early” for many of the VCs we met.

Two key components of our strategy at Boost were intentionally contrarian (ill-advised?) relative to the unofficial ‘startup playbook’ best practices. First, we went with the dreaded ‘horizontal’ (unfocused?) platform model and are stubbornly committed to that. Second, we took a slow and bottoms-up (unscalable?) approach with our go-to-market plan, which started by addressing an equally ‘risky’ or ‘a bit too early’ insurtech startup market to boot.

But despite skeptics, our team firmly believes in our long-term plan, and I’m incredibly proud that we’ve resisted countless urges to rush it or take short cuts. It was so hard (dumb?) that it damn near killed us twice, but you know what?

Totally worth it.

Since then, we’ve been honored to play a small role in dozens of other startups’ journeys as they build, launch, and scale meaningful insurance businesses on our platform. We work tirelessly to do one thing: make it simple for our partners to shake things up in their businesses, and we’re firmly committed to our role as their picks and shovels.

Doing so allows them to focus on the important stuff, like providing superior insurance products and delivering them through experiences that the modern consumer deserves - and that’s what matters.

Progress is never a straight line, but jeez, it’s been one heck of a ride already…

Everyone knows that working at a startup is like living a movie in fast forward, so it’s already been one hell of a journey for the Boost Squad. Closing our Series B after such an insane year is an awesome milestone for a lot of reasons, but I for one am glad that it means we can finally look back at some of the things we’ve been through together and laugh.

You know, things like...

The Ugly

Our original logo that was clearly just a blue Beats by Dre logo

(Thanks, freelance design platform...I want my $200 back!)



Back when we almost called the company a “virtual carrier”

(Fun fact: that was a dumb idea. Thanks, regulatory counsel!) 


Our randomly orange and purple website, the two grossest colors in the history of colors

(which is a universal truth and indisputable fact!)


The Bad

That time we looked each other in the eyes and made a really hard decision, one that would sacrifice a whole lot of short-term value in the interest of the long-term mission

…and did it together with the utmost trust and confidence in each other

...during a global pandemic 

…in the midst of black swan-level macroeconomic uncertainty 

…while teaching me how to use Zoom

(that wasn’t fun, but it feels like one heck of a special moment now)

The Good


Then there was the period after that hard decision, when we all buckled down and proceeded to 10x the company in nine months 

...swatting away all of the external headwinds and attacks that came our way

...because why not get all the hard stuff out of the way early – just to be sure, right?

And, finally, now a $20M Series B to put a bow on that horrible yet incredible experience

…that we got through together 

…not just to survive, but to thrive with momentum that can’t be stopped.

That last one brought me back to the days when we were in the “sweatbox” that we called home on Day 1. It was yet another reminder about why I’d gladly run through any wall or take any bullet for this team. And always will.

So now, everyone please keep your hands and feet inside the vehicle…

Today, Boost is quickly transforming into the machine that we dreamed of building, and its engine is humming louder and faster every day. We’re at that stage where you find yourself thinking “okay...I should probably be a little scared now, but it’s working so let’s just keep going.” Luckily, none of our investors or commercial partners want to slow down either. I’m pretty sure we forgot to install a brake pedal in the first place - and this capital is even more fuel for the machine.

The machine that is Boost has 10x’ed its customer base over the last few months, has launched six proprietary products (and counting) which are available through its full-feature policy admin API platform, and is consistently doubling every major financial KPI.

Plus, we get to work with some of the most innovative companies in the world – startups and enterprise alike – every single day. How awesome is that?

Like any startup, we’ve basically lived five lifetimes over the last five-ish years. There have been countless super high-highs and plenty of super low-lows, but it’s been incredible to watch our team work together to navigate it all, every step of the way. The lows are always hard, but we’ve always been hard to kill, and the highs can be fleeting – but it’s starting to feel like we’re getting pretty damn close to unstoppable.

I can’t wait for what’s next.

So, time to get back to work – but before we go...

For anyone crazy enough to have read this far and eager for more, we look forward to welcoming you into the Boost family. Join us as a Boost MGA partner (Get Started), a reinsurer (Contact Us), a member of the team (We’re hiring…a lot!), or as a friend of the company (Follow us on social).

Today, we’re going to celebrate in true Boost fashion – with a nice mix of aggressively unapologetic enthusiasm and gratitude for everyone that supports us...and maybe, just maybe, even a few drinks.

Tomorrow, we’ll wake up, dust ourselves off, and refocus – locked, loaded, and as always, just a little bit dangerous.

We have a ton of work to do, but we plan to keep that party going strong for a very, very long time.

Bring it on.


[1] Humblebrag Disclosure: I helped lead Marqeta’s Series C back in 2015, when I was still a VC. They were (and still are) one of the biggest inspirations for Boost. Such a kickass company all around.

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