Angel Portfolio Cira 2021-2023 Update

A few years back, I was in a position to make some small angel investments through SPVs, writing checks into early-stage companies with clear tailwinds from major macro trends. As I wrote in my original angel investing post, I focused on businesses I could understand, early-stage deals with sane valuations, and founders with advantages that mattered.

The thesis centered on companies positioned to benefit from lasting Covid-19 behavior changes, climate acceleration, space commercialization, and AI/ML improvements. After about 2 years, my role has made continued angel investing impractical, but those early bets have continued executing. This post summarizes how those companies have performed since investment, using only publicly available information. Nothing here constitutes investment advice.

In no particular order:

Scout Space: Autonomy + SDA in a Crowded LEO

When I wrote my Investment Review: Scout Space Systems about backing dual-use autonomy for a crowded low Earth orbit, the thesis centered on their ability to navigate the increasingly complex space environment. Since then, Scout has made significant progress on multiple fronts.

Blue Origin selected SCOUT’s Owl sensor for the first operational Blue Ring mission, targeted for spring 2026. This represents a high-visibility ride that should accelerate Owl’s on-orbit dataset and build customer confidence in the platform. Beyond commercial traction, the company won a $3.8M TACFI contract to build its first GEO flight unit, extending Owl into geostationary operations and signaling Space Force interest in their approach.

The flight-test momentum has been equally impressive. In August 2025, SCOUT and Dawn Aerospace completed a suborbital spaceplane test with Morning Sparrow aboard Aurora, reaching Mach ~1.0 at approximately 67,000 feet. This widened the training and data pipeline for very low Earth orbit space domain awareness, proving out the technology in increasingly realistic environments.

Switchyards: The Near-Home Third Place

My Investment Review: Switchyards focused on hyper-local membership and post-COVID work patterns, betting on the need for beautiful spaces near where people actually live. The network has continued expanding thoughtfully, now spanning 30+ neighborhoods with their “world’s first neighborhood work club” positioning clearly resonating.

Recent market expansion validates the model’s portability. Houston–Montrose opened in September 2025, while Dallas–Oak Cliff is live on the locations map. This demonstrates multi-metro expansion while maintaining the core “small, beautiful, near home” playbook that differentiates Switchyards from traditional coworking concepts.

Jericho Security: Human-in-the-Loop Security Training

The original thesis in my Investment Review: Jericho Security was about closing the last mile of AI security through user behavior modification. Jericho has expanded their product breadth significantly, with public materials now highlighting phishing simulation, remediation, policy training, and a user-facing Outlook add-in that lets employees report phishing attempts while feeding continuous learning back into the platform.

Flex: Owner OS Across Banking, Cards, AP/AR

Originally backed as Flexbase in my Investment Review: Flexbase, the company has undergone significant transformation. Starting with the rebrand to Flex and up to the recent launch of the Flex Visa Infinite Business Card.

The financing context tells the broader story. TechCrunch reported a $25M equity round alongside $300M in credit facilities, supporting the platform shift from construction-focused credit into a broader owner operating system. The M&A activity has been equally notable, with Flex acquiring Maza Financial in April 2025 to deepen payments and compliance capabilities while expanding team expertise.

Deep Sentinel: Pay for Outcomes (Deterrence > Footage)

My Investment Review: DeepSentinel emphasized their focus on deterrence over just footage capture. The company closed a $15M Series B in June 2025 to scale the AI plus human guard model and accelerate integrations. Product velocity has been strong, with the 2025 cycle emphasizing their Gen V Hub, broader third-party camera integrations, and on-demand guarding for business customers.

The “bring your own camera” motion has tightened significantly, reducing hardware friction that previously slowed adoption. Strategic integration with Digital Watchdog has broadened channel reach, validating the ecosystem approach to market expansion.

SeerAI: Decision-Grade Spatiotemporal Data

The thesis in my Investment Review: Seer.ai centered on providing decision-grade spatiotemporal data. Their Open Platform has matured significantly, curating high-value datasets like HIFLD while pushing schema standardization and live pipelines. This creates workflows that compress the typical “connect → explore → act” cycle that slows down geospatial decision-making.

Cambrium Bio: AI-Designed Molecules (Vegan Collagen → Polymers)

Since my Investment: Cambrium Bio post, the company achieved a significant distribution unlock. Brenntag signed on in January 2025 to distribute NovaColl™ across the UK, Ireland, Iberia, France, and Italy. This provides key channel leverage for personal-care adoption and validates the commercial viability of their AI-designed molecules.

The pipeline narrative has expanded as well, with Cambrium’s “Supermolecules™” positioning spanning from personal care into polymers. This hints at multi-product expansion beyond the initial vegan collagen wedge, which could significantly increase the total addressable market.

Beyond Aero: Hydrogen-Electric Light Jet (Luxury Beachhead)

My Investment Review: Beyond Aero focused on their luxury beachhead approach to hydrogen-electric aviation. The company closed a €20M Series A in October 2024 toward developing the BYA-1. Their 2025 communications outline an 800-nautical-mile range using battery-free fuel-cell architecture, with a 2030 certification target that positions them well ahead of traditional aviation timelines.

Alga Biosciences: Methane Cuts in Cattle at Feed-Additive Cost

The Investment Review: Alga Biosciences thesis was built around achieving massive methane reduction at feed-additive economics. Company materials continue citing up to ~97% methane reduction with low-inclusion additives, while maintaining an intentionally light press footprint. Academic literature and land-grant coverage through 2024–25 have kept algae-based methane mitigation in focus, with Asparagopsis pathways gaining broader recognition and supporting the category development.

SemiCab: Orchestrating Freight Networks (India Scale-Out)

My Investment Review: Semicab argued that orchestration beats spot marketplaces in freight. The corporate structure evolved significantly when Algorhythm Holdings (NASDAQ: RIME) acquired both SemiCab U.S. in 2024 and SemiCab India in May 2025, consolidating the network TMS and marketplace into RIME’s AI logistics platform.

Commercial momentum in India has been particularly strong. Recent releases highlight new wins and expansions, a supply-chain finance facility with Bank of America for SemiCab India receivables, Kellanova India expansion, and a new win with Bajaj Electricals. This represents healthy enterprise validation in a market where logistics orchestration can have outsized impact.

Homeroom: Higher-End Roommate Living (Now with Bungalow)

The original Investment Review: Homeroom focused on roommate living to expand attainable housing supply. Bungalow acquired Homeroom in April 2025, with Bungalow now hosting a Homeroom landing page that explains migration paths and model differences. This represents category consolidation amid broader affordability tailwinds in urban housing markets.

Retrospective: What Worked, What Didn’t, What I Learned

Looking back at the original thesis, the macro trend framing held up better than I might have expected.

The Covid-19 behavioral changes I bet on: near-home work patterns with Switchyards, the Homeroom roommate living model—proved reasonably durable even as the immediate pandemic panic faded.

The climate-related bets like Beyond Aero’s hydrogen-electric aviation, Cambrium’s AI-designed molecules, Alga’s methane reduction have had less tailwind from things like IRA than I had expected, but I think I was right that premium beachheads matter. Climate solutions need customers who’d pay regardless of government mandate or subsidy. These are brutally hard problems to tackle and I was investing at the earliest stages so I expect these to be patience games.

The “AI where outcomes matter” cluster: Deep Sentinel’s deterrence, Jericho’s behavioral defense, SeerAI’s geospatial decisions, SemiCab’s freight optimization has been a clear win. I wrote many of those memos before the ChatGPT moment, focusing on AI that solves measurable problems rather than pattern-matching for engagement. That framing aged well. What I missed was how fast and how much many of those era of AI companies would grow, I passed on some that I’m embarassed about in hindsight but that seemed too highly valued at the time.

The hardest lesson for anyone dabbling in angel investing is patience. You won’t get and shouldn’t expect information rights, and if you’re investing at the pre-seed you should plan on a decade of being a fan and not knowing a ton. I check up on all of these companies weekly to see if there is any interesting news but for the most part I don’t know any more than you would.

If I were starting this portfolio today, I’d keep a similar macro trend framing but be a bit looser on the valuations I was willing to tolerate given more recent AI premiums. Particularly at this very early stage I think getting into great companies at the right time that I understand is a more important measure. I’d weight more heavily toward companies where AI creates measurable outcomes rather than efficiency gains. And I’d be even more ruthless about the “I need to get it” filter.