BREAKING  Authentic closes $11M Series A led by FirstMark Capital Total raised to date: $16.5M Reached 1M+ small businesses through partners in year one Partners: Mindbody · Restaurant365 · PushPress · theCut Product: Captive in a Box launched Sept 2023 Founded 2022 · New York, NY BREAKING  Authentic closes $11M Series A led by FirstMark Capital Total raised to date: $16.5M Reached 1M+ small businesses through partners in year one Partners: Mindbody · Restaurant365 · PushPress · theCut Product: Captive in a Box launched Sept 2023 Founded 2022 · New York, NY
Company Profile · Insurtech · New York
Authentic company logo
AUTHENTIC — the wordmark and interlocking-loops mark used across the company's product and site. Photographed against its brand grid.

Authentic

The company that wants to turn every software platform into an insurance company - without asking it to hire a single actuary.

Captive in a Box · Program insurance infrastructure
Founded
2022
HQ
New York, NY
Stage
Series A
Team
~58
The Dispatch

Insurance, rebuilt from the balance sheet up

Most insurance startups redesign the quote form. Authentic went after something less visible and far harder to replicate: the machinery underneath. The New York company builds the infrastructure that lets software platforms, franchisors and associations launch their own insurance programs - captives - for the small businesses they already serve.

A captive is an insurance company owned by the people it insures. The model has existed for decades, but standing one up traditionally required lawyers, actuaries, reinsurance treaties and millions in capital. Authentic packaged all of it into software it calls Captive in a Box.

The result is that a gym-management platform or a restaurant software company can offer tailored coverage to its customers through a single integration - while Authentic runs the underwriting, rate filings, reinsurance, capitalization, regulatory compliance and claims behind the scenes.

Founder and CEO Cole Riccardi frames the opportunity bluntly: the way commercial insurance is bought and sold hasn't meaningfully changed in half a century. Authentic's bet is that distribution - reaching businesses inside the tools they already use - is where that changes.

$16.5M
Total raised
1M+
Businesses reached
10+
Platform partners
<$5M
Target member revenue
Who it's for

Built for Main Street

Authentic's members are the businesses too small for traditional carriers to court and too numerous to ignore: gyms, salons and spas, restaurants, barbershops, retailers and professional-services firms - typically under $5 million in annual revenue. It reaches them not directly, but through the platforms they trust.

The problem

Coverage that ignores small business

Commercial insurance is priced and sold for larger accounts. Small operators get generic policies, slow service and little say in how their risk is managed - and none of the upside when they run clean.

The problem

Captives were out of reach

The member-owned captive model rewards good risk, but building one meant actuaries, reinsurers, regulators and capital most communities can't assemble on their own.

Authentic's answer

Distribution where work happens

Partners embed coverage inside software small businesses already use every day, so buying insurance becomes part of running the business, not a separate chore.

Authentic's answer

Savings that flow back

Because members effectively own the program, when claims come in lower than premiums, the savings can return to them as dividends - aligning incentives around lower risk.

The way insurance is bought and sold hasn't changed in over 50 years. We're truly changing the commercial insurance industry.
— Cole Riccardi, Founder & CEO
Under the hood

What "Captive in a Box" actually handles

A partner integrates once. Authentic operates the insurance company that sits behind it - the parts that normally take years and a room full of specialists.

Underwrite & file

Actuarial analysis, rate setting and regulatory filings to bring a compliant program to market.

Capitalize & reinsure

Domiciling the captive, arranging reinsurance and putting capital behind the risk.

Quote, bind & embed

A unified rate-quote-bind engine lets partners sell tailored Business Owner's Policies inside their product.

Service & pay claims

Ongoing administration, claims management and customer service - plus dividends when claims run low.

Products & services

The lineup

Platform · 2023

Captive in a Box

The core end-to-end platform that lets a community stand up a captive program without a traditional carrier - underwriting, filings, reinsurance, capital, compliance and claims in one system.

Engine · 2023

Rate-Quote-Bind

An embedded operating system with an integrated quoting engine partners add via a single integration, so their customers can buy coverage in-product.

Coverage

Business Owner's Policies

Customized commercial coverage for gyms, salons, restaurants and barbershops - with member dividends when the program runs clean.

Roadmap · 2024

Workers' comp & beyond

Planned expansion of lines beyond BOP into workers' compensation, with additional coverage types such as health over time.

Where it fits

A $275B market, still run the old way

The U.S. commercial insurance market topped $275 billion in 2023 and is projected to nearly double by 2032. Insurance is famously recession-resistant - businesses keep coverage even when they cut elsewhere. Most insurtechs compete on a slicker front end for a carrier's product. Authentic's difference is that it owns the full captive stack rather than reselling someone else's policy. FirstMark Capital put it in stark terms: the platform can "virtually eliminate the need for traditional carriers."

Funding trajectory (USD, cumulative)
Seed 2023
$5.5M
Series A 2024
+$11M
Total
$16.5M
Bars scaled to total funding to date. Series A closed May 2024.
The cap table

Who's backing it

FirstMark Capital · lead Slow Ventures Altai Ventures MGV Upper90 Commerce Ventures
Distribution

The platforms that carry it

Fitness & wellness

Mindbody

Scheduling and business-management software for studios, gyms and spas - a channel into wellness small businesses.

Food & beverage

Restaurant365

Restaurant management software embedding Authentic coverage for food and beverage operators.

Fitness

PushPress

Gym operating system offering Authentic-powered insurance to gym and fitness owners.

Personal services

theCut

Barber booking app bringing tailored coverage to barbers and barbershops.

Origin story

From the racetrack to Main Street

Authentic's model traces back to an unlikely place: horse racing. Riccardi's family was involved with Big Stakes, a captive insurance program in the sport that shared unclaimed funds back with trainers - a design that rewarded safety by giving the insured a stake in the outcome. He recognized the same incentive structure could work for small businesses in commercial insurance, and built Authentic around it.

The record

How it got here

2022

Founded in New York

Cole Riccardi launches Authentic Insurance Services to bring the captive model to small businesses.

2023

Seed round and product launch

Raises $5.5M led by Slow Ventures and launches Captive in a Box in September 2023.

2024

$11M Series A

FirstMark Capital leads an $11M round (total $16.5M); signs 10+ partners, reaches 1M+ businesses and plans new lines.

Questions

Frequently asked

What does Authentic do?
It provides infrastructure that lets software companies, franchisors and associations launch their own captive insurance programs for the small businesses they serve - handling underwriting, reinsurance, capital, compliance and claims.
What is "Captive in a Box"?
Authentic's platform packages everything needed to run a captive program - actuarial filings, regulatory compliance, reinsurance, capitalization and claims - so a partner can offer tailored coverage without being an insurance company.
Who are Authentic's customers?
Software platforms and communities such as Mindbody, Restaurant365, PushPress and theCut, whose end users are Main Street small businesses - gyms, salons, restaurants and barbershops - typically under $5M in annual revenue.
How much has Authentic raised?
$16.5M total: a $5.5M seed (2023, led by Slow Ventures) and an $11M Series A (2024, led by FirstMark Capital with Slow Ventures, Altai Ventures, MGV, Upper90 and Commerce Ventures).
How does the member-owned model benefit small businesses?
In a captive, members share in the outcome. When claims are lower than premiums collected, the savings can be returned to members as dividends, aligning incentives around lower risk and fairer pricing.
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Profile compiled from public sources including the company website, its blog, AlleyWatch, FinTech Global, Coverager, Captive.com, Captive Insurance Times and Insurtech Insights. Figures such as revenue and headcount are third-party estimates and approximate.