Kenny
Stone
I'm a founder, software executive, and angel investor.
I found, build, and scale technology companies. I've been a CTO for two venture backed startups, including as cofounder of PlanGrid, where we raised over $100 million in venture capital from Y Combinator and Sequoia, and were acquired by Autodesk for $875 million in 2018. I have architected systems and managed software teams across a variety of industries, including construction, consumer media, and trading.
I live in the San Francisco Bay Area with my wife and toddler.
Angel Investing
I occasionally invest in technology startups, and I'm fortunate to be a small investor in some great companies listed below.
| Company | Description | Investing alongside... |
|---|---|---|
| Alpas | Helping procurement departments find suppliers. | YC, Harvard Endowment |
| Arcway | A real-time 3D engine where anyone can design a home. | |
| EverCurrent | AI-native platform aligning tools, processes, knowledge for hardware teams. | a16z |
| Handoff | Instant construction estimates and business operations for contractors with AI | YC, Initialized Capital, Greycroft |
| Hightouch | Customer data platform helps you collect and activate customer data alongside AI agents | YC, Amplify Partners, Rahul Vohra, Brianne Kimmel |
| Kanda | Affirm for construction. | YC, Liquid 2 |
| Mastra | All-in-one framework for building AI-powered applications and agents. | Paul Graham, YC |
| Merlin | AI-powered ERP for construction companies | YC |
| Monograph | The operating system for the built environment. | Homebrew, Parade VC, Index Ventures, Tiger Global, Base10 |
| Postscript | Messaging for Shopify stores. | YC, Greylock, Kevin Hale |
| Slope | Buy Now / Pay Later for B2B. | YC, Union Square Ventures |
| Toolbox | Debit cards for construction. | YC, Liquid 2, 1984 Ventures |
| Upcodes | Manage the complexity of building codes. | YC, Point Nine Capital |
| Walnut | Sales product demos made easy. | Liquid 2, NFX, SV Angel |
Some Investment Headlines
- Mastra announces $13M seed round from YC, pg, Gradient, and 120+ others (October 2025)
- Hightouch raises $80M on $1.2B valuation for marketing tools powered by AI (February 2025)
- Monograph raises $20M Series B+ from Base10 ventures (February 2025)
- Slope $65 Million Strategic Equity and Debt Funding (July 2024)
- Upcodes launches Copilot for building codes (May 2023)
- Postscript raises $65M Series C (June 2022)
- Slope raises $24M Series A from Union Square Ventures (April 2022)
- Walnut snaps up fresh capital after growing 700% in four months (January 2022)
- HighTouch announces $40M Series B (November 2021)
- Monograph raises $20M Series B (November 2021)
- 1build raises $19.5M Series A (September 2021)
- Walnut raises $15M Series A (August 2021)
- PostScript announces $35M Series B led by Greylock (March 2021)
Work History
I've been building software for over 25 years, often as a founder or CTO at early-stage startups. I love the earliest phases of company-building: learning a new business domain from first principles, talking directly with users, making hard tradeoffs, and shaping product, strategy, and architecture at the same time. I'm happiest when I'm close to the problem, the code, and the people.
Bedrock Energy2022–2024
In my fractional role as Head of Software at Bedrock Energy, I advised the founding team on software hiring, strategy, and execution, while building a vertically integrated geothermal energy company.
Geothermal has long been the most energy efficient, environmentally friendly way to electrify your buildings. Bedrock's novel technology makes geothermal borehole fields affordable, fast, and space-efficient to install, with predictable performance. Bedrock's mission is to transform the heating & cooling of buildings, using geothermal energy to radically reduce costs for people and the environment. Bedrock combines electrical, mechanical, drilling, and software engineering in a multi-disciplinary, fully vertical solution.
While delivering first of their kind products for the industry, I filled product, design, managerial, and architecture roles, recruited a software team, and helped raise a $12M Series A, scaling between 1 day/week to full-time over two years.
O.school2017–2018
I helped launch O.school, a health and wellness website centering women, non-binary, and LGBTQ community.
In my role, I architected and built a streaming video application for health educators across the country to lead interactive classes. The mobile friendly application included chat capabilities with real-time moderation and archival playback.
PlanGrid2012–2016
I cofounded PlanGrid, where we introduced mobile technology and machine learning to the $1 trillion construction industry.
While leading product development for 4.5 years, I grew the engineering team to 75, helped raise $85m+ in venture capital (Sequoia, Y Combinator, Sam Altman, others), and created a product more loved than Dropbox and Gmail. Today, PlanGrid is a leading software platform for construction and helps teams build the largest structures on earth.
PlanGrid was acquired by Autodesk in 2018.
Connamara Systems2007–2011
At Connamara, I built the platform that executed the first carbon auction in the United States, engineered high-frequency trading systems for hedge funds, and improved performance at the world's largest options exchange. During these formative years, I obsessively honed my craft across a wide range of projects, benefiting from exceptional mentorship while building mission-critical systems in the trading industry.
Tellabs2005–2007
I worked on the Tellabs Titan 5500, a carrier-grade digital switching system that cross-connected high-speed telecom circuits, dynamically allocating bandwidth and routing voice and data traffic between central offices with exceptional reliability and low latency. At its peak, the 5500 handled over 75% of all phone traffic in the United States, but I joined during its golden twilight, when it was still mission-critical to major carriers even as the industry was rapidly shifting toward a fully packet-based future.
Purdue University2000–2004
I graduated from Purdue University with a degree in computer engineering.