Matchstick Ventures

I’m thrilled to announce our $3.3M seed fundraise and the launch of Slant, the AI-native CRM for financial advisors. We’ve seen firsthand how automation can transform an advisor's business, and we are excited to take it to the next level. Over 1,000 advisors use Pageport every day, and as we worked with our customers, it became clear that everyone was working inside outdated legacy CRMs— forced to buy dozens of add-ons to get their job done efficiently. It’s time for an upgrade to advisor CRMs— Slant is built with AI front and center, designed to help advisors build better relationships at scale. If you’re an advisor or want to be part of the team helping 20 million Americans get the financial advice they need, schedule a demo or apply to one of our open roles!

🔍✨ Platform Spotlight: Shannon Stobbe Shroyer, Head of Platform & Operations at Matchstick Ventures From professional ballerina 🩰 to VC operator, Shannon brings precision, adaptability, and grace to everything she builds. As Matchstick’s first and only Platform hire, she’s designed systems, communities, and processes that scale—without ever losing the human touch. In this week’s #SoYouWantToWorkInPlatform newsletter, Shannon shares: – Her path from the world of fine art and ballet to venture – What it means to build Platform as a one-person team – Why every founder touchpoint—big or small—can be meaningful – How the role has evolved year to year, and her experiments with AI to scale lean Read the full interview here 👇

I'm excited to share that Juno has raised a surprise $4 million Seed round. We hadn’t planned on raising more capital so soon after the initial $2 million round we closed just a few months ago, but this opportunity allowed us to strengthen Juno’s balance sheet—ensuring we’ll be here to deliver for our customers no matter the market conditions. Our founding team still maintains full control of the business, which means we get to build in the way we believe will best fulfill our mission: solving the gnarliest, most stubbornly offline workflows in corporate travel. We started with guest travel—our bread and butter—but Juno is now expanding into four additional, equally offline categories: life sciences, higher education, and production travel, with more verticals to come later this year. We’re fortunate to welcome some incredible partners to the table this round—most of whom have been with us since the Pana days. Huge thanks to Tali Miller (who sourced the Pana deal for BVP) and Addie Lerner Katz for leading the round, and to Nicole Glaros (who served on Pana's board and helped us navigate both the good times and the COVID times) and the Matchstick Ventures crew for participating. I’m also deeply grateful to Steve Singh, Matthew B. Ziskie, David Ambrose, and Reed McBride for continuing to double down on the business and supporting us in all the ways you do. We wouldn’t be here without our insanely talented team. Thank you to Jason Tudor, Michael Hottman, Danny Glunz, Stacy Moore, and my wonderful cofounders, Devon Tivona and Kate Porter. We’ve got some exciting things lined up for the rest of the year—I can’t wait to share more soon.

We just announced $5.6M in new funding and the general availability of Freeplay, with a new free tier. 🎉 We’re building Freeplay to help software teams optimize their AI products, with easy-to-use tools for evaluation, experimentation, and observability. Now any team can start building the data flywheel they need to make great AI products and agents. We’ve been fortunate to build the product with amazing customers who love Freeplay, and now I’m excited to get it in the hands of more teams. "I can't even express how much easier it is to debug our system now. Y’all have built a truly excellent product." - Principal ML Engineer at a Fortune 100 company "Today we ship and iterate on AI products with real confidence about how any change will impact hundreds of thousands of customers." - Ian Chan, VP of Engineering at Postscript “As soon as we integrated Freeplay, our pace of iteration and the efficiency of of prompt improvements jumped—easily a 10x change.” - Michael Ducker, Co-founder & CEO at Blaide "The time we're saving with Freeplay is invaluable" - Luis Morales, VP of Engineering at Help Scout The best part of building the company is our incredible team and investors. Eric Ryan has been an incredible partner on the journey since day 1, and we’ve got an amazing team building together in Boulder, CO. (PS: We're hiring!) We were fortunate to meet Roseanne Wincek and Renegade Partners last year. They led the round, and Roseanne has already proven to be exactly the partner we hoped for. Our amazing existing investors Sarah Guo at Conviction and Natty Zola at Matchstick Ventures joined, along with the great folks at Next Frontier Capital, PWV (led by Tom Preston-Werner, GitHub co-founder), Ashley Smith's Vermillion Cliffs, and an awesome crew of individual investors and advisors with backgrounds at places like GitHub, Atlassian, Dropbox, Roblox, Scale AI, and more. If you're building an AI product and working to improve your prompts and evals – or just getting started thinking about evals! – I'd love for you to try Freeplay and let me know what you think. The demo below shows how easy it is to get started. Link to the full post in the comments 👇

Can’t believe it’s already been a week since we were in Boulder for the Lit at Boulder Startup Week party! Still buzzing from the energy of getting the OG crew back together and connecting with so many friends in the community. Big highlight: celebrating the newest member of the Matchstick Ventures team, Nicole Glaros! What a way to welcome her 🎉 Thanks to everyone who came out—it was lit. #BoulderStartupWeek #StartupCommunity #MatchstickVentures #LitByMatchstick

Congratulations to our founder and CEO, Jane Mosbacher Morris, for being named to Inc. Magazine’s 2025 Female Founders 500 List as one of the top innovators! 🎉 This list honors the most innovative women in business—leaders who are tackling some of the world’s biggest challenges head-on. Jane’s work at TO THE MARKET - driven by our software, TRACERA - is reshaping global supply chains, proving that responsible sourcing isn’t just the right thing to do—it’s the smartest way to reduce risk and build long-term value.  We’re beyond proud to see her recognized among such an incredible group of female founders! View the full list here: https://lnkd.in/gEb9rQb9 Join us in celebrating this moment and tag a female founder who inspires you!