Shares of Navan closed at $20, down 20%, in first-day trading on Thursday, indicating lackluster investor demand for the long-awaited debut.
Navan, which operates an expense management platform with an emphasis on travel, had priced shares for its offering at $25 each late Wednesday. It was formerly called TripActions, with the company pivoting to a broader platform when revenue reached zero right after the COVID pandemic hit.
The offering raised $923.1 million for the company, whose shares are trading on the Nasdaq under the ticker NAVN. It set an initial valuation of around $6.2 billion.
The move to the public markets has been a long time coming for Palo Alto, California-based Navan, which reportedly first submitted confidential paperwork for a planned offering more than three years ago.
The company had raised $1.2 billion in debt financing and $1 billion in equity funding from venture investors and credit providers, per Crunchbase data. Major venture stakeholders include Andreessen Horowitz, Lightspeed Venture Partners and Zeev Ventures.
Growing revenue
Navan had revenue of $329 million in the first half of 2025, up 30% year over year. Growth comes as the company has been investing in developing its agentic AI offering, Navan Cognition, to automate more cumbersome tasks around travel planning and reporting.
Still, the company remains far from profitable. Navan’s net loss for the first half of this year came in just shy of $100 million — up about 7% from the year-earlier period. The loss comes amid higher spending on both R&D and sales and marketing — common for companies on the IPO track — looking to appeal to growth-hungry investors.
Per its IPO filing, Navan has incurred net losses in each year since its inception in 2015 and “may not achieve or, if achieved, sustain profitability in the future.”
It was 2021 and Jonathan Rat was tired of seeing his wife, a dentist, struggle to maintain the tech stack at her practice.
Rat, who had served as a product manager at companies including Uber, Meta and SurveyMonkey, dug into the problem and discovered that “most of the software used in the industry” was more than 20 years old and still required physical services onsite.
“Most lacked integration with other platforms, were slow and buggy, and impossible to train new employees on,” he recalls.
Archy Founders Benjamin Kolin and Jonathan Rat
So Rat teamed up with Benjamin Kolin, a former director of engineering at Uber, to start Archy, an AI-powered platform that aims “to put dental practices on autopilot.” The pair previously led the rebuilding of Uber’s payment platform that’s still in use today.
“I realized there was a massive need and opportunity for a modern, cloud-based software platform and set out to build that,” Rat told Crunchbase News. “I also realized bigger tech players have been building software for the larger healthcare market but overlooked the $500 billion dental industry.”
And now, Archy has just raised $20 million in Series B funding to help it grow even more, it told Crunchbase News exclusively. TCV led the financing, which also included participation from Bessemer Venture Partners, CRV, Entrée Capital and 25 practicing dentists who wrote checks as angel investors. The raise brings Archy’s total funding to date to $47 million, Rat said.
The company raised a $15 million Series A led by Entrée Capital almost exactly one year ago. Rat confirmed the Series B was an up round, but declined to disclose Archy’s valuation.
All-in-one tool
Archy claims to replace more than five existing tools to handle scheduling, charting, billing, imaging, insurance, payments, staffing, messaging and reporting “from one login.”
It is now building AI agents “to handle the busywork” such as checking eligibility, filing and following up on claims, writing notes, managing patient communications and scheduling, and “turning raw practice data into clear answers,” according to Rat.
The startup processes more than $100 million in payments annually across 45 states and has seen roughly 300% year-over-year growth, he said. It currently serves 2.5 million patients and has processed over 35 million X-rays through its platform.
The company claims that mid-sized dental practices report saving around 80 hours a month by using its technology, and are able to avoid “big hardware costs.” For example, Rat said that one practice saved about $50,000 in its first year of using Archy.
Dual-revenue model
San Jose, California-based Archy operates on a dual-revenue model that combines subscription-based fees with payment processing services, and offers tiered monthly subscription packages. In addition to its subscription fees, Archy serves as a merchant processor for its clients, generating revenue from a percentage of payment transactions processed through the platform.
“This hybrid approach allows us to remain aligned with our clients’ success while providing flexible options that scale with their business needs,” Rat told Crunchbase News.
The company plans to use its new capital to “hire aggressively” across its engineering, AI and go-to-market teams. Presently, it has 57 employees. It plans to expand internationally starting in 2026.
Austin Levitt, partner at TCV, told Crunchbase News via email that his firm had been looking for a way to invest in the dental space “for a long time” but didn’t find a company that was “appropriately tackling the root of the problem — the core PMS (practice management systems)” until it came across Archy.
He added: “We consistently heard that Archy was supremely easy to use, requiring almost no training in contrast to others, providing a seamless ‘iPhone-like’ experience, and reducing what took 10 clicks in other software to one or none in Archy.”
Every founder knows the thrill of the moment: the first term sheet lands, the product is live, the market is opening up. But in 2025, there’s a new line in the sand: Did you clear the regulatory path before you scaled?
Today, it’s not enough to disrupt the market — you have to anticipate the rule-set that will govern it.
Investors are shifting gears. After a decade of “move fast and break things,” they’re asking: Who built the compliance engine before the crash? Because the truth is, regulation has become a form of alpha — a competitive advantage for startups that think of law not as a hurdle, but as a moat.
The new era of smart compliance
The startup landscape has changed. High-profile failures — from crypto exchanges to wild valuations in fintech and AI — taught us that the regulatory cost of growth can be massive. Today’s investors and founders alike expect legal strategy from day one, not as an afterthought.
Consider the RegTech market: One recent estimate projects it will swell to about $70.64 billion by 2030, growing at a compound annual rate of roughly 23%. Another forecast predicts growth to $70.8 billion by 2033. The message: Companies are no longer asking if they need compliance automation and legal-engineering infrastructure. They’re asking when they can monetize it.
So when a startup designs its product around KYC, AML, data-protection or licensing from the outset, it’s not just avoiding risk — it’s building a moat others will struggle to cross. For founders, regulation isn’t just the cost of entry anymore — it’s the cost of exit-edge.
When the law becomes a moat
There are former unicorns, and there are regulation-ready unicorns. The difference hinges on when they built their compliance architecture, hired legal engineers and treated regulation as product.
Take payment infrastructure: Stripe built payment-security and licensing into its model early, as Stripe’s PCI Level 1 certification and multijurisdiction licenses (U.S. money-transmitter, EU/UK e-money) enabled it to integrate cleanly with Apple Pay, power Shopify’s native payments, and — per a 2023 announcement — expand its role processing payments for Amazon.
Or look at crypto: Coinbasebuilt a licensure footprint early, publishing its U.S. money-transmitter licenses and securing New York’s BitLicense in 2017. Its 2021 SEC S-1 repeatedly frames regulatory compliance and licensing as fundamental to the business.
In insurtech, from the outset, Lemonade hired senior insurance veterans (e.g., former AIG executive Ty Sagalow) and, per its S-1 and subsequent filings, expanded licensure across the U.S., operationalizing the 50-state regulatory landscape rather than trying to route around it.
These examples show a pattern: When compliance is built in from the start, the cost of scaling drops and competitors face much higher entry bars. Regulation becomes a moat — not a burden.
The rise of ‘legal engineering’
Welcome to the era of the legal engineer. The traditional model (sign contract, then lawyer reads, then flagged risk) is being replaced by code, automation and internal teams who speak both product and law.
And what’s happening in AI? Founders are hiring general counsels on day one to forecast imminent regimes — privacy law (GDPR, CCPA), AI transparency bills, emerging algorithms-as-infrastructure regulation.
The startup battle isn’t simply product vs. product anymore — it’s regulatory architecture vs. regulatory architecture.
Regulation-ready startups aren’t just surviving — they’re attracting smarter capital. Venture funds now assess regulatory maturity, legal runway and governance readiness early on. A startup that can show it isn’t “waiting to deal with compliance” but designed it, has a valuation edge.
Funds are no longer only assessing TAM or go-to-market speed; they’re asking: “What’s the regulatory runway? Who owns risk? Who built the compliance pipeline?” Because in sectors like fintech, climate tech, health tech and AI, the fastest growth path is often the one that avoids the enforcement arm.
The future: law as competitive advantage
Let’s zoom out for a moment. We’re moving into a world where regulation isn’t a ceiling — it’s scaffolding. It defines markets, enables scaling and filters winners from pretenders. Founders who see law as a source of architecture, not as chewing-gum-on-the-shoe, will be the ones writing the playbook.
Think about AI: Startups that design for regulatory change (data-provenance, audit trails, rights management) are already positioning for the future.
Think about climate tech: Companies that can navigate evolving carbon-credit regimes or ESG disclosure laws are building invisible advantages.
Think about fintech: Those that mastered licensing, KYC/AML, consumer-data flows early are the backbone of infrastructure.
The next wave of unicorns won’t just have better tech — they’ll have truly infinitely better legal DNA. They won’t just disrupt a market; they’ll help write the rules of the market before they scale.
Because in this new era, regulation isn’t a deadweight — it’s a launchpad.
In her new role, Haskaraman will focus on investing in “soon-to-break-out” AI infrastructure, cybersecurity, and applications companies for Felicis, an early-stage firm with $3.9 billion in assets under management.
During her time at Menlo, Haskaraman sourced investments in startups including Semgrep, Astrix, Abacus, Parade and CloudTrucks — zeroing in early on how AI is reshaping developer security and enterprise infrastructure.
Feyza Haskaraman, partner at Felicis Ventures
Haskaraman, an MIT graduate who was born in Turkey, brings an engineering background to her role as an investor. She previously worked as an engineer at various companies at different growth stages, including Analog Devices, Fitbit and Nucleus Scientific. She is also a former McKinsey & Co. consultant who advised multibillion-dollar technology companies and early-stage startups on strategy and operations. It was after working with startups at McKinsey that her interest in venture capital was piqued, and she joined Insight Partners.
Her decision to join Menlo Park, California-based Felicis stems from a shared interest alongside firm founder and managing partner Aydin Senkut to build communities even in “unsexy” industries such as infrastructure and security, she said.
“Whether it’s connecting AI founders or bringing together technical and cybersecurity communities, the mission is the same: Believe in the best founders early and help them go the distance,” she told Crunchbase News.
Felicis is currently investing out of its 10th fund, a $900 million vehicle, its largest yet. More than 60% of its investments out of Fund 9 and 10 (so far) are seed stage; 94% are seed or Series A. In 83% of its investments, Felicis has led or co-led the round.
In an interview, Haskaraman shared more about her investment plans at Felicis, as well as why she thinks we’re in the “early innings” with AI. This interview has been edited for clarity and brevity.
Let’s talk more about community-building and why you think it’s so important.
Over the past few years in the venture ecosystem, just providing the capital is not enough. You need to surround yourself with the best talent. You’re seeing one of the fiercest talent wars in terms of AI talent.
So one of the things that I’ve spent a lot of time on in my VC career is building a community, going back to my MIT roots, surrounding myself with founders, engineers and operators, and also going into specific domains, like cybersecurity — just building a network of CISOs that I communicate with regularly and really support them however I can, and then obviously get their take on the latest technology.
That type of community-building effort is something that Aydin and I will be debating strategy for Felicis as well.
Yes, Aydin (Felicis’ founder) has said that he thinks the next generation of enterprise investors aren’t just picking companies, they’re building ecosystems. Would you agree with that?
Yes, we’re fully aligned on that. First of all, it’s a way of sourcing. Being able to source the best founders involves surrounding yourself in a community of people. You get very close to them, and you want to be the first call when they decide to jump ship and start a business.
As early-connection investors, we want to invest in the founders as early as possible. So that’s why we want to immerse ourselves in these communities that provide prolific grounds for the technical founders that are coming in and building an AI.
You were investing in AI before the big boom took off. Would you say there’s too much hype around the space?
You are correct that there is a lot of euphoria around AI, but if you look at the overall landscape, we haven’t seen a technology that can have such a large impact.
And we’re already seeing the results in enterprises that buyers of these solutions, and consumers of these solutions, including myself and our team, are seeing immense amounts of productivity gains. I remain immensely optimistic about the future and investing in AI, and that’s what we are paid to do, and what I also enjoy as a former engineer.
Are there specific aspects of AI that have you particularly excited?
I personally feel we’re still very much at the early innings. It’s been three years since ChatGPT came out, and the model companies really pushed their products into our lives. But if you take a look at what’s happening now, we have agents that are coordinating and automating our work.
What are ways in which we should be securing agent architecture? And that is also evolving across the board, and if you think about another layer down, like the infrastructure to support these LLMs and agents, I have to ask “What do we need underneath?”
I think there’s a lot more that will come, and there’s a lot of hope for innovation that will happen both across the infrastructure layer, as well as agents. There’s also the issue of “can applications actually be enabled?” I go back to the importance of securing our interactions with the agents and making sure that they’re not abused and misused. It’s a great time to be investing in AI.
What stages are you primarily investing in at Felicis?
We try to go as early as possible. But obviously, given our fund’s size, we have flexibility to invest whenever we see the venture scale returns make sense. But the majority of our investments are seed.
It’s such a competitive investing environment right now. How do you stand out?
Ultimately, what founders value is how you will work with them, your references. They value how you show up in those tough times, how you surround them with talent, how you help them see around the corners. That matters a lot.
I believe that winning boils down to the prior founder experiences that you left, people who can speak highly of you and how you work. I tend to be a big hustler. So, there’s a lot more value-add that we want to make sure we bring to the table, even before investments. And then after the investment we can continue to bring that type of value to a company.
Are you investing outside of AI?
I’m investing in AI infrastructure, cybersecurity and AI-enabled apps. We are also at the verge of a big overhaul in terms of the application layer, companies that we’ve seen prior to AI — that is all getting disrupted.
We’re seeing AI scribes in healthcare intake solutions, for example. We’re seeing code-generation solutions in developer stacks. We are looking at every single vertical, as well as horizontal application. I’m very interested in how all of these verticals’ application layers will get a different type of automation.
What’s your take on the market overall right now?
I feel like I lived three lifetimes in my investing career — just over the past few years. We as a VC community and tech ecosystem learned a lot, obviously, just in terms of what’s happening. We’re seeing new ingredients in the market, and that is AI, that did not exist during COVID.
Think about the fact that this is not a structural change in the market driven by the economy. This is truly a new technology. I would bucket those waves as separate.
I’m very grateful to be investing at this time. What a time to be investing, because AI is truly game-changing as a technology.
Clarification: The paragraph about Haskaraman’s investments at Menlo Ventures has been updated to more accurately reflect her role.
Whatnot, a live shopping platform and marketplace, has closed a $225 million Series F round, more than doubling its valuation to $11.5 billion in less than 10 months.
DST Global and CapitalG co-led the financing, which brings the Los Angeles-based company’s total raised to about $968 million since its 2019 inception. Whatnot had raised $265 million in a Series E round at a nearly $5 billion valuation in January.
As part of the latest financing, Whatnot says it will initiate a tender offer where select current investors will buy up to $126 million worth of shares.
Funding to e-commerce startups globally so far this year totals $7.1 billion, per Crunchbase data. That compares to $11.3 billion raised by e-commerce startups globally in all of 2024. This year’s numbers are also down significantly from post-pandemic funding totals, which surged to $93 billion in 2021.
‘Retail’s new normal’
Live commerce is the combination of livestreaming and online shopping. Grant LaFontaine, co-founder and CEO of Whatnot, said in an announcement that his startup is “proving that live shopping is retail’s new normal.”
Whatnot co-founders Logan Head and Grant LaFontaine. Courtesy photo.
The company says more than $6 billion worth of items have been sold on its platform in 2025 so far, more than twice its total for all of 2024. Its app facilitates the buying and selling of collectibles like trading cards and toys through live video auctions. It also offers items such as clothing and sneakers. It competes with the likes of eBay, which currently does not offer a livestreaming option. It’s also a competitor to TikTok Shop.
“Whatnot brought the live shopping wave to the US, the UK, and Europe and has turned it into one of the fastest growing marketplaces of all time, Laela Sturdy, Whatnot board member and managing partner at CapitalG, Alphabet’s independent growth fund, said in a release.
The company plans to use its new funds to invest in its platform, roll out new features and “evolve” its policies. It is also accelerating its international expansion, adding to its current 900-person workforce by hiring across multiple departments.
On Oct. 21, the publicly traded crypto exchange announced that it is acquiring early-stage investing platform Echo for $375 million in cash and equity.
Notably, the acquisition marked the eighth buy for the San Francisco-based company in 2025 so far, according to The Wall Street Journal. Of those eight deals, three involved undisclosed businesses.
Overall, since its 2012 inception, Coinbase has acquired dozens of companies, per Crunchbase data. Besides Echo, it announced purchases of the following startups in 2025:
In January, it acquired Stryk, the Cyprus-based unit of BUX, as part of a European expansion. Stryk offers CFD trading services to European residents through an app. Financial terms were not disclosed
Also in January, Coinbase picked up Spindl, a 3-year-old San Francisco-based startup that developed a blockchain-based attribution system to help businesses accelerate user growth.
In May, it acquired Deribit, a 10-year-old cryptocurrency derivatives exchange offering options, futures and spot trading for digital assets based in the Netherlands.
Then in July, Coinbase acquired Liquifi, a 4-year-old San Francisco-based startup that helps crypto companies automate their token vesting and lockups, and manage their token cap table. Liquifi was a self-described “Carta for crypto.”
Now it has announced plans to buy Echo, an onchain digital platform that helps communities invest together and aims to give founders more options for their cap table.
Coinbase’s buying sprees seem to come in spurts, according to the data.
Crypto’s crash and recovery
For example, in 2018, it acquired eight known companies. And then in 2021, it picked up seven known companies. But most years, it acquired only one or two companies.
Interestingly, 2018 was defined by what has been described as the “Great Crypto Crash,” or a massive market sell-off after the boom that took place in 2017. Things had rebounded by 2021, which saw a bull market for crypto and the rise of NFTs and DeFi. That November, Bitcoin hit an all-time high of $68,000.
After a bumpy few years, which saw the arrests of FTX founder Sam Bankman-Fried and Binance CEO and founder Changpeng Zhao, Bitcoin has rebounded, surging to an all-time high in 2025. Prices reached $113,156.57 on Oct. 15.
In announcing its plan to acquire Echo, Coinbase said the two companies shared a similar mission of “democratizing early-stage investing, so that more people can support the next generation of breakthrough companies.”
The buy complemented its earlier acquisition of Liquifi, Coinbase said, noting that: “While Liquifi strengthened our ability to support builders at the start of their journey, Echo extends that support into fundraising.”
The largest of its acquisitions in 2025 so far, though, was its $2.9 billion buy of Deribit.
Meanwhile, Coinbase’s market cap as of Oct. 23 hovered just under $83 billion, while its stock is up over 25% year to date.
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