Watchlist: June 2026 Edition.
Starcloud raises at a $2B+ valuation, OpenRouter becomes a billion dollar company. Six prospects join the watchlist.
Today marks the end of Q2, and there are a number of developments to catch up on. First, Starcloud rides SpaceX tailwinds into a $2B valuation, officially the most valuable company listed on Watchlist this year.
Starcloud becomes a unicorn, twice.
On March 30, 2026, Starcloud announced their $170M Series A at a $1.1B valuation, led by Benchmark and EQT. The company is now in the process of raising a $200M Series B round valuing Starcloud at $2.2B, reportedly led by Manhattan West. Caplight’s pricing engine is showing lots of secondary demand from investors, with an implied $3.3B valuation based on the flurry of bid action. Starcloud was previously covered in the January edition, and at the time, the company was only a seed stage prospect, having raised $24M from Sequoia, Y-Combinator, and In-Q-Tel. When the Series A round was announced in March 2026, Starcloud became the fastest company to reach unicorn status in Y-Combinator history. Starcloud’s primary goals now are to develop large, low-cost deployable radiators and make high-performance chips work in a higher-radiation environment. Multiple second movers are now raising fresh capital to try and take advantage of the influx of investor interest:
Orbital raised a $5M pre-seed round from a16z speedrun to build AI data centers in low Earth orbit.
Cowboy Space Corporation raised a $275M Series B round at a $2B valuation, led by Index Ventures. Cowboy was originally Aetherflux before pivoting from space-based solar power delivery to orbital data centers. Led by Robinhood co-founder Baiju Bhatt, Cowboy Space is actually building their own rockets to launch space data centers, as they believe rocket availability is the true constraint.
It will be interesting to watch how the competitive dynamic unfolds, specifically between Cowboy Space and Starcloud; Cowboy’s vertically integrated approach could either pose a threat or prove unsustainable in contrast to Starcloud’s reliance on SpaceX. Nonetheless, true commercial scale eludes the category for the near future.
OpenRouter breaks through to unicorn status.
On May 26, OpenRouter announced their $113M Series B at a $1.3B post-money valuation, led by CapitalG, Google’s growth equity arm. OpenRouter provides developers access to over 400 AI models, claims over 8 million global users, and processes 100 trillion tokens per month. Their revenue has more than doubled since February. The company’s focus for the rest of the year is to develop their enterprise (B2B) business, as many large technology companies are overspending on AI and OpenRouter’s product allows access to a wide range of models for a low price. OpenRouter was previously covered in the January edition.
Benchmark Makes More Moves.
A few months ago, we wrote a short memo about Benchmark slowly breaking away from their old ways by adding Jack Altman. The brand evolution has accelerated in real time; two weeks ago the firm raised $2B in new funds, by far its largest ever haul, including a $1.25B growth fund for a thirty year old firm that has never done a growth fund before. The early stage fund ballooned to $725M, nearly double the firm’s typical $425M fund size. Venture capital’s most disciplined high profile fund has opened the floodgates, a sign of the times if there ever was one. Andreessen Horowitz, Thrive, Founders Fund, Battery Ventures and Lux have collectively raised $36B in the first quarter of 2026, about 80% of venture capital raised in that time period. The top venture firms have significantly expanded in fund size over the past few years, forcing Benchmark to reassess their historical position on deliberately smaller sized vehicles. Paired with the Altman hire, all signs point to Benchmark intentionally shaping a new era for the platform going forward.
On a related note, Jack Altman made his first investment as a Benchmark partner in May, leading a $50 million Series B into Monaco, an AI company building “the future of sales” for startups, and also joining the board. More on that deal below.
June 2026 Watchlist.
Monaco
Company Overview: Monaco is an AI native sales engine for startups, built by former Brex CRO and Founders Fund investor, Sam Blond. Monaco launched in February 2026, announcing both its $10 million seed and $25 million Series A, both led by Founders Fund. The company has reportedly been adding seven figures of annual recurring revenue each month since launch. As mentioned previously, their latest fundraising round was a $50 million Series B round led by Benchmark, with Jack Altman taking a board seat.
Founders: Sam Blond - co-founder and CEO of Monaco, former Partner at Founders Fund, former CRO at Brex; Brian Blond - co-founder and Chairman of Monaco, Investment Partner at Human Capital, former Managing Director at Sutter Hill Ventures; Abhishek Viswanathan - co-founder and CPO of Monaco, former CPO of Apollo, former CPO of Qualtrics; Malay Desai - co-founder and CTO of Monaco, former Senior VP of Engineering at Clari.
Investors: Benchmark, Founders Fund
Amount Raised: $85M+ (Series B stage)
Headquarters: San Francisco, CA
Probook
Company Overview: Probook is an AI operating system for home services. The company uses one AI system to optimize bookings, leads, and onboarding for home services businesses in HVAC and plumbing. Their desired outcome is to increase customer EBITDA post-installment. Probook claims their engineering team “is more talent dense than early Ramp,” with ICPC World Finalists and IMO Gold Finalists.
Founders: George Eliadis - co-founder and CEO of Probook, Wharton graduate; Lewis Zhang - co-founder and CTO of Probook, Senior ML Engineer at Roblox, UC Berkeley graduate; Ben Cervantez - co-founder of Probook, Wharton dropout.
Investors: Andreessen Horowitz, Sequoia
Amount Raised: $40M+ (Series A stage)
Headquarters: San Francisco, CA
Ploy
Company Overview: Ploy is a marketing platform that turns startup websites into a growth engine. Founded by former Webflow co-founder, Bryant Chou, whose experience building a multi-billion dollar website platform will prove useful. Ploy raised $27 million in a seed round after participating in Y-Combinator’s Spring 2026 batch.
Founders: Bryant Chou - founder and CEO of Ploy, former co-founder and CTO of Webflow ($4B private val.), former senior software engineer at Intuit.
Investors: First Round, Y-Combinator
Amount Raised: $27M+ (seed stage)
Headquarters: San Francisco, CA
Caplight
Company Overview: Caplight is building the institutional standard for private markets pricing. With $5B in daily live secondary transaction opportunities and 700+ institutional market participants on the platform, Caplight has built both the leading secondary trading marketplace and price discovery platform. The company recently announced a $16M Series A led by BlackRock and Fin Capital with participation from UBS. The investment from BlackRock unlocks collaboration across its private markets ecosystem, specifically Aladdin and Preqin.
Founders: Javier Avalos - co-founder and CEO of Caplight, former Deutsche Bank Investment Banker, former Forge Senior Vice President of Marketplace; Justin Moore - co-founder and CTO of Caplight, former Engineering Manager at Forge.
Investors: BlackRock, Fin Capital
Amount Raised: $26M+ (Series A stage)
Headquarters: San Francisco, CA
Critical Energy
Company Overview: Critical Energy is building modular power plants that convert heat into electricity, starting with geothermal. The systems ship in standard containers and install in weeks instead of years. The first power plant is scheduled to be completed by 2027 and will be installed at an existing geothermal site much like the ones in Northern California or Iceland. Founded by former SpaceX propulsion engineer Spencer Jackson.
Founders: Spencer Jackson - founder and CEO of Critical Energy, former Senior Propulsion Engineer at SpaceX, Rose-Hulman Institute of Technology graduate.
Investors: Susa Ventures, Upfront Ventures
Amount Raised: $22M+ (seed stage)
Headquarters: Los Angeles, CA
OffDeal
Company Overview: OffDeal is an AI-enhanced investment bank for small and medium sized companies, focused on sell-side M&A advisory. OffDeal equips young mid-level bankers with technology systems to run sell-side processes for businesses that are too small for traditional investment banks. Their proprietary tech finds 1,000+ relevant buyers on average and the company services profitable, owner-led businesses ranging from $5-100 million in revenue. A 5% success fee is applied when a transaction closes, but no retainers or upfront costs are dedaucted from sellers. OffDeal recently closed the sale of LG Logistics Solutions to Fura, an AI powered logistics service provider.
Founders: Ori Eldarov - co-founder and CEO of OffDeal, former Investment Banking VP at RBC, UBC graduate, HBS graduate, Y-Combinator W24; Alston Lin - co-founder and CTO of OffDeal, former Meta software engineer, University of Waterloo graduate, Y-Combinator W24.
Investors: Radical Ventures
Amount Raised: $17M+ (Series A stage)
Headquarters: New York, NY
