Jeff Stewart backed one of my companies about a decade ago, so it was great to have him on this week to share what he’s been building toward ever since. He’s the founder of GPO Fund, a growth-stage venture firm launched in 2018 with a specific mandate: back growth stage founders who want to expand … Read more
Carta has done 13 acquisitions in 14 years. Four of them happened in the last 15 months. Davis Thacker has personally led or helped lead 11 of those deals. So when I sat down with him to talk M&A strategy, product vision, and where Carta is taking its platform, there was a lot of ground … Read more
Lindsay Kaplan co-founded Chief, built one of the most talked-about communities in tech, and then left to go on a year of soul-searching (and like many founders, angel investing). Coming out of that walkabout was Lindsay joining up with our friends at Bullish as a Venture Partner. In her new role, she’s hunting for “weird” … Read more
Chieh Huang has seen disruption cycles before. As co-founder of Boxed (the bulk shopping app that went public via SPAC), he built a company that employed thousands of warehouse workers. Now he’s betting that AI will trigger the biggest workforce transition in a generation. And he just launched Pelgo to help people land on the … Read more
I just wrapped up a conversation with Andrew Pignanelli, co-founder and CEO of The General Intelligence Company of New York. His story of closing an $8.7M seed round from Union Square Ventures is one of the wilder fundraising journeys I’ve heard in a while. Big thanks to Yohei Nakajima, who was a seed investor in … Read more
I just had a great conversation with Datum CEO Zachary Smith. His latest venture, Datum, just announced a $13.6 million funding round to tackle something most of us don’t think about: access to the fundamental primitives of the internet. While hyperscalers like AWS and Google have built massive empires on cloud infrastructure, there’s a whole … Read more
The team at Reducto closed their Series B in 48 hours. The seed round? Five days. Series A? One day with each investor. Warp speed timelines like this are incredibly rare in a single fundraise. Let alone across 3 different fundraises. So who wrote the checks? Why did the founders take those checks? And what … Read more
Two big names in the private markets technology space just made two big moves, all in the same week. First, Juniper Square announced the acquisition of Tenor Digital, an AI-native platform for private credit automation. Two days later, Carta announced their own private credit related acquisition, of Sirvatus, a tech-enabled loan administration platform. Why the … Read more
By Venture5 Team | September 24, 2025 Most AI companies are struggling with a brutal stat: 95% of enterprise AI projects are failing. But Distyl AI just closed a new $175 million Series B (including participation from Lightspeed, Khosla, DST, and others) with a very different story—100% production success with Fortune 500 clients, 5x growth … Read more
Yesterday I grabbed Flybridge GP Jesse Middleton on the day they announced their 7th fund for a quick interview. Excited to share what we learned with you! First, the tl;dr: The firm now has most of its investment team based in NYC, with Jesse flying to Boston monthly while the Boston team comes down a … Read more
