Great Sky Selected for DOE’s Genesis Mission

This is such an amazing accomplishment by the Great Sky team!

Natty Zola
7/29/2026
57% of enterprises traced a wrong AI answer to missing business context — Credible bets portable, open-source semantic code beats proprietary metadata

We are excited about what the Credible team is building!

Natty Zola
7/29/2026
Green Project Technologies Acquires Optera to Build the Leading AI Climate Management Platform

Green Project Technologies announced the acquisition of Optera a Matchstick Fund II company. Together they form the industry's leading AI climate management platform, uniting Optera's decade of enterprise carbon management with Green Project's category-leading supply chain engagement and renewable energy procurement infrastructure. The unified solution is a true end-to-end platform for companies of any size, geography, or climate maturity, with AI at the core.

‍

‍

Natty Zola
7/17/2026
We're hiring an Investment Analyst

We are hiring for a Investment Analyst who will be responsible for sourcing, researching, and building relationships with the ambitious founders we back across our core markets between the coasts. This relationship-driven role will strengthen and expand the top of Matchstick's funnel, helping us find and connect with exceptional founders earlier and more often than anyone else. This role requires forming genuine relationships across our ecosystem, sharpening investment judgment through hands-on analysis, and experimenting with new AI tooling to make how we source and work smarter.

Sound like something you or someone you know would like to tackle? If so, check out our Investment Analyst Job Posting.

‍

Shannon Shroyer
7/17/2026
Apax Digital Funds Invest in Inspectorio to Further Accelerate Growth at Leading AI-powered Supply Chain Quality and Risk Management Platform

Inspectorio, a production-chain management platform from Matchstick Fund I,  announced a growth investment from the Apax Digital Funds, the growth equity arm of Apax. Congrats to the entire team!

‍

‍

Ryan Broshar
7/16/2026
LA’s first luxury gas station set to open in 2027

The Matchstick team can't wait to be the first customers at Maggie's! Congrats on the first location!

Shannon Shroyer
7/8/2026
Warmly was acquired by HubSpot!

Warmly has been acquired by HubSpot! We are proud to have been a part of the Warmly company journey.

Natty Zola
6/30/2026
Dalton Mills raises $9.2M!

Dalton Mills has raised $9.2M to help the trades build software that works the way they do.

For too long, contractors and skilled trades have had to adapt their businesses to rigid, one-size-fits-all software. Dalton Mills is turning that model on its head—enabling companies to create bespoke, AI-powered workflows without writing code.

As software evolves from systems of record to systems that do the work, Dalton Mills is helping bring the next era to one of the most important sectors of our economy.

Congratulations to the Dalton Mills team on the raise and on the mission to let the builders build.

‍

Natty Zola
6/8/2026
Our investment in Entravia

We are thrilled to share Matchstick's investment in Entravia, a workflow platform modernizing the Professional Employer Organization (PEO) sales process. The company is Minneapolis based and growing fast!

Ryan Broshar
5/29/2026
Our investment in Dalton Mills

We are thrilled to announce our participation in Dalton Mill's launch! 

Natty Zola
5/13/2026
Fun Raising from VC Sheet featuring Natty Zola

Catch Natty Zola on the VC Sheet podcast where he breaks down his thoughts on Founder and VC dynamics, fundraising, early stage hiring and more! 

Shannon Shroyer
4/21/2026
Two Boxes Accelerates AI-Powered Returns Processing Platform with New Funding Led by Assembly Ventures

A huge congrats to the Two Boxes team who raised a $3.2M round, bringing their total funding to $13M as capital-efficient platform scales to $1B in inventory value processed across three continents.

Ryan Broshar
4/7/2026
CometChat secures $6.5M from Run Ventures

Congrats to the CometChat team on this next raise.

Natty Zola
3/18/2026
Our investment in Great Sky

We are excited to announce our investment in Great Sky! The team spent a decade developing a superconducting optoelectronic network, or SOEN, which uses light to communicate data, while GPUs use electrons. This chip can process videos more than 1 million times faster than conventional models running on standard GPUs, with less energy.

Natty Zola
3/13/2026
Orijin Acquires Honest Jobs to Create the First End-to-End Education-to-Employment Pathway for Justice-Involved Individuals in the U.S.

We are thrilled with the opportunites that are made possible with Orijin's acquisition of Honest Jobs.

The acquisition unites Orijin’s education, rehabilitation, and workforce preparation platform with Honest Jobs’ national employer network and reentry technology, creating the only comprehensive end-to-end pathway connecting incarceration to meaningful employment.

‍

Natty Zola
2/26/2026