« Back to News

boldstart 2025 recap

  • 12.30.2025

Founders and Friends,

2025 was a foundation-setting year for enterprise AI. The market matured, buyers became more discerning, and founders were forced to build with greater clarity around value, trust, and durability. As AI reshaped how software is built, sold, and deployed, we witnessed the fastest company formation cycle in our 15-year history. Founders returned to first principles, and we doubled down on what we do best: partnering with technical founders from Inception.

This year also marked a major milestone for boldstart: we announced Fund VII, a $250M fund dedicated to inception-stage investing in the autonomous enterprise. This brings our total assets under management to over $1B, affirming our unwavering commitment to being the first institutional partner for the next generation of category-defining companies.

We also closed the first exit in AI security history with Protect AI being sold to Palo Alto Networks for over $700M, backed 15+ new founding teams across cybersecurity, AI infrastructure, and agentic automation, and watched multiple portfolio companies cross the $100M ARR threshold. From San Francisco to Tel Aviv to New York to London, the boldstart Inception model continued to prove its edge in the most competitive market in a generation.

Looking ahead to 2026, we are more excited than ever about the opportunity set for the autonomous enterprise. At the same time, we believe the market is entering a decisive sorting phase. Too much capital flowed into too many companies across increasingly crowded categories, and the rising tide that once lifted early momentum is receding. In the year ahead, winners and losers will separate. Some companies once perceived as early leaders will face pressure, while others opt for early acquihires. The very best teams, those delivering real execution, real outcomes, and real revenue, will continue to attract outsized capital on compelling terms. In markets like this, discipline wins, execution compounds, and the foundation for the best companies is built from Inception.

A heartfelt thank you 🙏🏼 to our founders, limited partners, co-investors, and friends for making this one of our strongest years yet.

We’re just getting started.

Time to build 🏗!

The boldstart team


Portfolio Company Activity

2025 was a breakout year for the boldstart portfolio, with major exits, follow-on rounds, ARR milestones, and product launches across the board. Here are the highlights:

🌎 Global coverage: 🇺🇸 🇮🇱 🇬🇧 🇨🇦

🤝 Inception rounds led: 15 new founding teams (mix of stealth and announced) spanning cybersecurity, AI infrastructure, domain-specific foundation models, and agentic automation

  • Initial check sizes: $500K to $10M across Discovery 6, Classic 4, and Jumbo Inception rounds 5
  • Categories: Cybersecurity: 3 | AI Infrastructure: 5 | Physical AI: 2 | Agentic Automation: 5

🏆 From Inception to Exit:

  • Protect AI acquired by Palo Alto Networks for $700M+, marking one of the earliest and largest outcomes in AI security. We partnered with Ian Swanson and the team in late 2021, co-leading their Inception round and supporting them through their journey to becoming the leading AI/ML security platform.
  • Superhuman was acquired by Grammarly and renamed Superhuman, creating an $800M+ ARR, profitable, AI-native productivity platform
  • Cycle was acquired by Atlassian to unlock AI-powered feedback in Jira Product Discovery
  • Auxon acquired by Ford to join Ford’s Advanced Electric Vehicle Development team.

💰 From Inception to Follow-On Funding:

  • Clay raised a Series B at $1.3B valuation and a Series C at $3.1B valuation, continuing its exponential growth trajectory after surpassing $100M ARR in just two years from $1M and create the category for GTM Engineering
  • Keycard raised $38M total ($8M Inception + $30M Series A) to become the trust layer for AI agents
  • Humanix raised $18M ($6M Inception + $12M Series A) to expand AI-powered protection against social engineering
  • Hypernative raised $40M Series B to expand real-time threat prevention across crypto and TradFi
  • CloudQuery raised $16M Series B, acquired Tailwarden, and 4xd ARR
  • Waldo announced $10M Series A led by Footwork and an inception round led by boldstart ventures
  • Kustomer raised $30M Series B led by Norwest Venture Partners to lead the AI native CX future
  • Reco raised $25M after growing ARR 5x to lead the shift to Dyanamic SaaS Security

🏗 From Inception to Product Launch:


FUND VII ANNOUNCEMENT 🎉

In 2025, we announced boldstart Fund VII: $250M dedicated to Inception-stage investing in founders building the autonomous enterprise. 

Read more from our launch here.

TL:DR 

We are in the earliest stages of a platform shift that will surpass both cloud and mobile, and it is already beginning to reshape the enterprise. This next wave is not just about automation. It is AI-native, agent-powered, and autonomous by design.

It will not happen overnight. But over the next decade, humans will do less and less, while software, agents, and machines will think, plan, and act on our behalf.

We are backing the core primitives of this shift:

AI-native infrastructure, orchestration layers, secure identity, optimized compute, and semantic interfaces.

The autonomous enterprise will require entirely new business models, robotic execution layers, and AI-native workflows built without a traditional back office. Crypto and smart contracts will unlock programmable money and permissionless automation, enabling trustless coordination across systems at scale. Systems will run at machine scale, continuously learning, reasoning, and operating in real time.

The Wall Street Journal also covered the launch.


TEAM & THOUGHT LEADERSHIP

We published extensively in 2025, helping founders navigate the AI-native era.

Ed Sim continued writing his weekly newsletter What’s 🔥 in Enterprise IT/VC with standout posts such as:

The Enterprise Agent Hunger Games #442” on the importance of delivering solutions for the last mile of the enterprise:

“And if you’re going in the enterprise, the demands are extremely high – you can’t vibe code your way into production – that last mile is everything – security, privacy, compliance, integrations, determinism and repeatability, accuracy, memory, cost, orchestrating swarms of agents, and even more security.”

The $5M Line That Is Redrawing Inception/Seed Investing #474” on the clear line that shows your round size picks your investors, and your fund size picks your battles.

Team Podcast Appearances:

Ellen Chisa:

Eliot Durbin:

Ed Sim:

Ed also continued to receive industry recognition as one of the top early-stage investors in enterprise technology as he was once again named to Business Insider’s Seed 100 and made the Forbes Midas Seed List for the fourth year in a row.

Finally, Fast Forward, led by Ron Miller, continued to grow as a publication focused on how CIOs and CISOs are approaching AI adoption in the enterprise. Through profiles and analysis, it complemented our work with founders by providing perspective on how large organizations are evaluating and deploying new technologies with interviews with IT Executives from JP Morgan, Goldman Sachs, Capital One, Salesforce and many more.


EVENTS

Charlotte Chapanoff, our Head of Marketing and Global Events, delivered another exceptional year of founder-first programming:

2nd Annual Enterprise Founders Summit – Miami 🌴

In January, we welcomed 75+ boldstart founders from the US, Israel, and Europe for two days of deep learning and collaboration. The theme: “Velocity is King” – in shipping, sales, and learning.

Key takeaways:

  • Momentum compounds: ship, learn, adapt, repeat
  • Trade $ for speed in sales velocity
  • If you’re stuck, figure out how to unstuck yourself – inertia is a powerful force
  • We’re on the cusp of a revolution none of us can fully comprehend

Read the full recap here.

First boldstart Inception Bootcamp – Boston

Ellen Chisa led our inaugural Inception Bootcamp in partnership with SVB. Over two weeks, 14 teams worked together in person, learning from ecosystem experts, spending 1-on-1 time with boldstart partners, and helping each other navigate the journey from idea to Inception.

Participants praised the hands-on approach, peer learning, and access to the boldstart network. We’ll be expanding the Bootcamp in 2026.

RSA 2025 Founders & CISO Event

We co-hosted our annual RSA event with IVP, featuring a standout panel with CISOs and security executives from:

  • Anthropic
  • JPMorgan Chase
  • Adobe

The central theme: securing AI and the evolution of AI security from experimental to mission-critical.

AI Dinners & Founder Gatherings

Throughout the year, we hosted intimate dinners and events across:

  • New York City (AI security, devtools)
  • San Francisco (AI infrastructure, foundation models)
  • Boston (Inception Bootcamp, cybersecurity)
  • Miami (Founders Summit, LP event)

LOOKING AHEAD TO 2026

As we close out 2025, we’re more convicted than ever in the Inception model. AI-native companies are redefining entire categories, and the technical founders building them need partners who understand infrastructure, security, go-to-market, and the unique challenges of selling into the enterprise.

With Fund VII, we have the resources and platform to support even more founders from Inception. 

Thank you again to everyone who made 2025 extraordinary. To our founders: your ambition, resilience, and execution inspire us every day. To our LPs: thank you for trusting us to back the earliest, hardest, and most important companies. To our co-investors and friends: we couldn’t do this without you.

Time to build 🏗!


If you’re a technical founder about to start a company and want a partner from Inception, DM boldstart or any one of us:

Ed Sim, Eliot Durbin, Ellen Chisa