I recently took a seat in the red chair with @karaswisher to chat all things from operating and investing to micromobility, the next wave of social and Midwest culture.

1/ NEW from Roam⚡️ Millions of homeowners are stuck. They locked a ~3% rate, but moving means jumping to ~6–7%. So they wait. Roam now gives them a better way. 🧵

To everyone out there born today (like me), check this out … we’re #1!

One of the primary career inspirations I had at @Opendoor was around the ability to make the buying and selling of homes frictionless. Why can't you buy a house in one single click? Now you can. We're excited to launch "Buy now" on Roam.

Today is the biggest product launch in Mutiny's history. Every B2B CMO I talk to says that AI has turned their marketing playbooks upside down: • Outbound effectiveness is plummeting as AI spam floods inboxes • Ads that used to work are now just more noise • Inbound leads are down as LLMs hijack their SEO traffic But what if instead of spamming buyers with AI, we used AI to deeply understand our buyers and build genuine relationships with them? That’s why we built 𝗔𝗜 𝗳𝗼𝗿 𝗘𝗻𝘁𝗲𝗿𝗽𝗿𝗶𝘀𝗲 𝗚𝗧𝗠, the fastest place to launch breakthrough campaigns for target accounts. We use AI agents to: • Research accounts to identify needs and uncover themes across accounts • Create personalized landing pages and ads based on what’s relevant for each account • Arm sales with personalized content and engagement insights for their accounts Companies like Uber, GitLab, Twilio, and LaunchDarkly are transforming how they connect with enterprise buyers with Mutiny. Early results are insane! In just 60 days, LaunchDarkly used the product to: • Book 45 enterprise meetings with Fortune 500 accounts • Exceeded pipeline goals by 50% • Operated at 12X the average ABM productivity Even established enterprises with more complex workflows like BMC Software have hit the ground running, launching breakthrough campaigns in hours. We're building a world where go-to-market teams can move at the speed of thought, executing every creative idea instantly without dependencies. Link to the launch blog post: mutinyhq.com/blog/ai-for-ent… #B2BMarketing #AI #EnterpriseGTM #ABM

Good lore: In 2018, Christina estimated the entire SOC2 compliance market at just $100M. Vanta alone now does far more revenue than that. They made compliance easy, so customers started demanding it. Some early investors didn’t buy the TAM either- They bet on Christina, thinking she’d pivot into something bigger. Instead, by the Series A, Vanta was doing ~$10M ARR (w/ only $3M seed) and raised $50M at $500M from Sequoia. Also, a score for VCs-turned-founders: Christina worked at USV. Congrats @TrustVanta & @christinacaci!

Today, we’re announcing @TrustVanta's Series D and new valuation – $4.15 billion – led by @Wellington_Mgmt alongside @sequoia, @ycombinator, @CrowdStrike, @GoldmanSachs, @jpmorgan, @craft_ventures, and @Atlassian. Vanta’s mission is to help businesses earn and prove trust.

We caught up with @christinacaci (Co-Founder & CEO of @TrustVanta) right after they announced a $150M Series D at a $4.15B valuation, and asked how it all started. "We started with SOC 2 for startups, because in 2017, no one got SOC 2. Now you get it when you’re two founders. That wedge gave us the access to help with more and build trust." "That was the seed pitch. It was literally the 2018 deck. And now we're here, a little later, actually doing it."

I'm excited to share that Ashby has raised a $50M Series D! In just over a year since our Series C, we've scaled from 1,300 to over 2,700 customers, grown revenue by 135% year-over-year, and maintained best-in-class efficiency (burn multiple <1x). A huge thank you to our customers—you’ve shaped our journey and continue to influence the product we're building for thousands more to come. And of course, a massive shoutout to our team 💜. We recently crossed 220 team members, and the talent bar and quality of execution remain exceptional. I've written a longer memo outlining the shifts we're seeing in TA and our strategic focus moving forward—doubling down on AI (and product velocity broadly), operationalizing Quality of Hire, scaling Enterprise Adoption, and investing in Customer Success and Community: ashbyhq.com/blog/culture/ser… There's plenty left to do - onward, upward, and back to work! 📈

With @windsurf_ai now owned by @cognition_labs, the story that needs telling is how @apartovi and @neo have amassed a venture stake in almost every major vibe-coding / AI-coding platform: Replit Devin (Cognition) Codeium (Windsurf) Cursor (Anysphere)

Fireflies has crossed the $1 billion valuation mark with our recent tender offer! We’ve done this while staying profitable, growing rapidly, and without raising primary capital since 2021. This milestone means a lot, not just because of the number, but because it allowed us to recognize the early team members who helped build Fireflies and placed their trust in us.

I’m excited to announce the public launch of First Harmonic. We are a small team of former operators who invest in early-stage companies and run what I believe is the world’s best go-to-market program for seed-stage founders. We have run six cohorts of the program to date with an NPS of 100 across the nearly 50 founders who have participated. Over a long career in tech, I’ve had the privilege of working with Steve Jobs and Ed Catmull at Pixar, of taking Twitter from $0 in revenue through IPO as the CFO and COO, and of mentoring hundreds of founders at all stages in 10 years as a YC partner. I’ve also been fortunate to invest as an early angel in several breakout AI companies, including Mercor, Decagon, and Cursor. I’ve seen the arc from inception to IPO many times and recognize what separates winning startups from the pack. It's this multi-stage experience as an operator and investor that is uniquely valuable to the founders in our program. What’s this program about? A common challenge that all founders face in the early days is defining their ideal initial customer. Great go-to-market strategy begins with narrow customer selection. Every important decision is downstream of customer definition: roadmap priorities, customer acquisition strategy, sales model, pricing, etc. If you don’t define your customer well, everything else becomes extra hard. In our program, we help founders nail early customer definition through intensive 1:1 work. It’s the point of highest leverage. Our cohorts are small (10 to 12 companies), and we don’t accept applications. Instead, we select founders who have been nominated by people we trust, increasingly by alumni of our program. The program requires a 3–4 hour weekly time commitment over 8 weeks and sets startups on the right go-to-market path for life. The program will always be free and non-dilutive to founders. In order to make this possible, we’ve raised an early-stage fund that covers the costs of running the program. But there are no investment expectations or strings attached to participating. If you’re an early-stage founder, you can read more about what we believe in the link in comments. If you’re a seed investor, we hope to collaborate with you.

This copy-trading app is tapping into the influencer economy to bring young investors into the stock market. f-st.co/CiIOLHK

Rick Song might be the most reluctant founder we’ve backed at @firstround—but also one of the most gifted. @Persona_IDV just closed a $200M round, and today we're releasing our long-form interview on the unconventional moves fueling Persona’s rise. Rick and Persona break most Silicon Valley norms—I hope more learn from their story.

If you think joining the public service is just taking a cut in salary, think again. See what Katie Stanton gave up! Super deep, thoughtful, emotional and interesting episode of Invested podcast with @KatieS. Link to full episode below. DO NOT MISS IT.

We are proud to support @Persona_IDV in their Series D funding round. From day one, we’ve believed that Persona and co-founder @rickcsong would power the digital transformation of identity verification through a software-native solution. Learn more: forbes.com/sites/rashishriva…

Thank you to @FortuneMagazine and @CatMcGrath5 for breaking this exclusive. And also @BusinessInsider and @arperelli for our featuring our deck & narrative on the finance x creator economy. Fortune link here: fortune.com/article/copy-tra… Business insider link here: businessinsider.com/pitch-de…

dub just raised a $30M Series A to change how America invests. People are bad at picking stocks. Instead, they should pick smart people to copy-trade. Here’s dub’s story:👇

@Neo just raised $320M after successful seed investments in Cursor, Kalshi, Bluesky, & more. Thank you to all the brilliant people helping Neo become tech's premier community for talent & startups. From Sheryl & Schrep to Sam & Satya, read more in this fab @Forbes feature.

Today, Roam announces our $11.5M Series A led by @rabois and @khoslaventures with @foundersfund to fix the broken housing market and help 75 million Americans afford a home. We're hiring to accelerate our mission to make homeownership 2x more affordable. Here's how we do it 🧵

🎉🎉 DIGITS IS LIVE 🎉🎉 After five years of heads-down building, and another year of intensive testing with hundreds of startups, it's launch time: Digits is the first end-to-end accounting platform for the AI era. Try it FREE at digits.com!