Enterprise Weekly #545: Capital One Buys Brex, Importance of Humility & Clarity for Founders, and More
Work-Bench is a NYC-based $160M enterprise software Seed stage VC fund. If you are or know anyone thinking about founding an enterprise software, SaaS, or infrastructure software startup - we’d love to meet! Please reach out to chat.
Happy Friday!
We didn’t have to wait too long for our first M&A splash in the world of enterprise software. On Thursday, Capital One acquired Brex for $5.15B. It’s full circle, given that Capital One also acquired Ramp co-founder Eric Gylman’s first company, Paribus.
Some interesting data points:
The acquisition represents 3.5% of Capital One’s market cap.
Brex brings with them 25K customers. While the company started off selling to startups, 25% of revenue is now enterprise.
As of last fall, they were at $700M of revenue and growing 50%.
This is the marriage of two founder-led companies, as Capital One’s founder Richard Fairbank is still running the company as CEO today!
There’s a number of lessons to be learned from Brex. The company started in 2017 and set the fastest record to $100M in revenue back in 2018, in the days pre-AI. They entered an industry (corporate cards) where early stage startups didn’t normally sell, being first of their kind. They are reflective of the fact that startup journeys are never always up and to the right; there are good times and there are bad times, and the fortitude to stick with it is nontrivial.
There’s been a lot of talk in recent days about the valuation Brex got bought at. It’s interesting to hear the perspective of Brex CBO Art Levy:
“With Brex, because we had this meteoric rise and then we had a few years of figuring things out and then a turnaround, what that meant is that we are actually pretty well positioned to understand how public market companies are valued. We understood what great businesses, businesses like Shopify and Toast and Adyen and Affirm and Navan, trade at. And when looking at those multiples and those gross profit multiples, this is actually an insanely premium deal and a very, very well-priced deal for everyone.”
Having the humility to acknowledge being in a state of figuring things out (every company experiences this!) and the clarity to align with the new reality are traits that all companies can learn from Brex. Congrats to them on a great outcome!
🎤 Founders & Falsettos | A New Year NYC Karaoke Jam (Jan 27th): Work-Bench is excited to co-host a New Year karaoke night for NYC founders and operators, alongside our friends at Flybridge, Next Wave NYC, The Venture Collective, Mercury, and Ramp. Join us for an evening of karaoke, drinks, and conversation with people building and operating some of NYC’s most interesting companies. Whether you’re stepping up to the mic or just enjoying the crowd, it’s a relaxed way to connect with the broader startup community and kick off the new year together. Sign up here.
🚀 From Engineer to Founder: Building and Selling Developer Tools with Extend (Feb 12th): Work-Bench is hosting an intimate fireside chat with Kushal Byatnal, Co-Founder & CEO of Extend, for a candid conversation on building and scaling enterprise software. We’ll dive into Extend’s founding story, Kushal’s transition from engineer to founder, and the real lessons behind product-market fit, go-to-market, fundraising, and building with AI. It’s a small, curated gathering designed for thoughtful conversation and high-signal connections with NYC founders and operators. Sign up here.
📚 Read more news:
WSJ: We Have No Idea How to Code. So We Got Claude to Code This Article for Us.
TechCrunch: Are AI agents ready for the workplace? A new benchmark raises doubts
VentureBeat: Everything in voice AI just changed: how enterprise AI builders can benefit
CNBC: Workday CEO calls narrative that AI is killing software ‘overblown’
Reuters: Intel struggles to meet AI data center demand, shares drop 13%
🧵 Read more threads:
Jessica Lin: Why the New B2B launch Playbook is...B2C
Proby Shandilya: Sandboxes for Agents
Erik Yao: Testing AI Like It’s 2015
OpenAI: Scaling PostgreSQL to power 800 million ChatGPT users
Company: Courier Health
Role: Customer Engineer
Technology: Patient Engagement Platform
Funding: $20.5M from Work-Bench and Norwest Venture Partners
🌟 Company of the Week 🌟
AiStrike raises $7M led by Blumberg Capital
Risk / Security - Seed - Pleasanton, CA
Founders: Kayzad Vanskuiwala, Nitin Agale
Dam Secure raises $4M led by Paladin Capital Group
Risk / Security • Seed • Sydney, Australia
Blockit raises $5M led by Sequoia
Collaboration / Productivity • Seed • San Francisco, CA
Asymmetric Security raises $4.2M led by Susa Ventures
Risk / Security • Pre-Seed • San Francisco, CA
Stilla raises $5M led by General Catalyst
Collaboration / Productivity • Pre-Seed • Stockholm, Sweden
Yuki raises $6M led by Hyperwise Ventures
Data / AI / Machine Leaning • Seed • Tel Aviv, Israel
Legato raises $7M led by S Capital
Infrastructure / Dev Tools • Seed • Tel Aviv, Israel
Furl raises $10M led by Ten Eleven Ventures
Risk / Security • Seed • Los Angeles, CA
Artie raises $12M led by Dalton Caldwell
Data / AI / Machine Learning • Series A • San Francisco, CA
Ditto raises $12.2M led by Craft Ventures
Collaboration / Productivity • Series A • San Francisco, CA
Stoïk raises $23.4M led by Opera Tech Ventures and Impala
Risk / Security • Series C • Paris, France
TitanX raises $27M led by Updata Partners
Sales / Marketing • Series A • Knoxville, TN
Benepass raises $40M led by Centana Growth Partners
HR Tech • Series B • New York, NY
Ivo raises $55M led by Blackbird
Future of Work • Series B • San Francisco, CA
Datarails raises $70M led by One Peak
Collaboration / Productivity • Series C • New York, NY
Emergent raises $70M led by SoftBank Vision Fund 2 and Khosla Ventures
Infrastructure / Dev Tools • Series B • San Francisco, CA
Applecart raises $100M led by Blackstone
Sales / Marketing • Private Equity • New York, NY
DealHub.io raises $100M led by Riverwood Capital
Sales / Marketing • Private Equity • Austin, TX
Railway raises $100M led by TQ Ventures
Infrastructure / Dev Tools • Series B • San Francisco, CA
Claroty raises $150M led by Golub Growth
Risk / Security • Series F • New York, NY
Inferact raises $150M led by a16z and Lightspeed
Data / AI / Machine Learning • Seed • San Francisco, CA
Upscale AI raises $200M led by Tiger Global, Premji Invest, and Xora Innovation
Infrastructure / Dev Tools • Series A • Santa Clara, CA
Baseten raises $300M led by IVP and CapitalG
Data / AI / Machine Learning • Series E • San Francisco, CA
ClickHouse raises $400M led by Dragoneer Investment Group
Data / AI / Machine Learning • Series D • San Francisco, CA
humans& raises $480M led by SV Angel and Georges Harik
Data / AI / Machine Learning • Seed • San Francisco, CA
Yelp acquires Hatch for $270M
Future of Work • Acquisition • Richmond, VA






Wow, the part about Brex's record-setting growth in the pre-AI days really stood out to me; it makes one reflect that the grit and fortitude you highlighted are still the most crucial algorithms for success, even before the big neural networks arrived, and your insights are truly brilliant.