Meet United States’s 101 Top Founders in the Cannabis Space

Shawn Carpenter

Founder & Managing Partner of Three Tree Ventures

Shawn Carpenter is the Founder and Chairman of the Board at Three Tree Ventures, an early-stage technology startup investment fund that backs exceptional entrepreneurs that are applying technology to market segments with high caps that have had a historically incorrect, ineffective and/or insufficient level of technology application. Three Tree Ventures prefers to invest in startups as early as possible, has historically only invested in product companies, and prefers to invest in organizations with one or more U.S. military veteran founder(s). Since early 2014, Shawn has also been an LP and Advisor to CrossCut Ventures (https://www.crosscut.vc) in Los Angeles, CA. Mr. Carpenter is a globally respected cyber security expert with a broad range of successful early-stage investments, including Compass (IPO on NYSE #COMP 4.1.2021 @ $8.22B valuation), Privateer Holdings (acquired by Tilray), Awake Security (acquired by Arista Networks), Left Coast Ventures (acquired by Subversive Capital), GroupSense, White Ops (now known as “HUMAN” acquired by Goldman Sachs Merchant Banking) ThreatGRID (acquired by Cisco), RideScout (acquired by Daimler AG), InAuth (acquired by American Express) and Efflux Systems (acquired by NETSCOUT Systems). Mr. Carpenter is known for his acumen in advising early stage innovators. He has successfully helped Three Tree Ventures portfolio entrepreneurs and their companies raise capital for pre-Seed, Seed, and Series A investment rounds, navigate rough waters, acquire key talent and customers, and help develop short and long-term business strategies. He currently advises CrossCut Ventures, Trinity Cyber, TruSTAR Technology (acquired by Splunk 5-2021), AgentHero, GroupSense, uStadium and Netswitch Technology Management. He has held key positions at startups where he was an early employee — Principal Forensics Analyst at NetWitness, Chief Technical Analyst at iSIGHT Partners, Chief Strategy Officer at Invotas, and Senior Vice President of Cyber at Cybraics. One of his passions is being the Technical Advisor for a non-profit 501(c)3 founded by his wife, Dr. Jennifer Jacobs, and a close friend, Jessica Stern — Connect Our Kids (https://www.connectourkids.org). The organization is applying modern technologies like artificial intelligence and data science to the United States foster care system to improve outcomes. His experience and successful entrepreneurial background are coupled with deep technical skills honed while pioneering cyber security protocols for the federal government and working at NetWitness and iSIGHT Partners over the past two decades. Shawn is also a veteran of the US Navy, and qualified as a nuclear operator and chemist during his six years of service in the US Navy’s Nuclear Propulsion Program (NNPS Class 9203). Shawn also worked as a senior cyber security analyst for almost six years as a Member of the Technical Staff (MTS) at Sandia National Laboratories. After joining NetWitness as one of the first employees, he helped architect, implement and stand up the Justice Security Operations Center (JSOC) — at that time the largest deployment of NetWitness gear for a federal client. Mr. Carpenter also worked as a principal senior analyst at the US Department of State’s Cyber Threat Analysis Team (CTAD) from 2004-2007; he was a key member of the 2005 CTAD team that was awarded the prestigious Frank B. Rowlett Trophy For Organizational Achievement by the National Security Agency. Shawn has been tinkering with computers since he bought his first computer, a TRS-80 Model I, in late 1978 at the age of 10. He has been curious about almost everything since he was born, and enjoys playing slide guitar, banjo and trumpet, metal detecting with his kids, climbing tall trees, building forts, lucid dreaming, experimenting with brain/machine interfaces, building robotic banshees, and hacking all of the things. Mr. Carpenter has a particular affection for blues and jazz, and is an investor and minor partner in a John Coltrane biography — “Chasing Trane” (https://www.coltranefilm.com). His investments span everything from technology-enabled real estate, to being the first money in at Rumi Spice (https://www.rumispice.com), a sustainable saffron growing enterprise founded by three West Point graduates that served in Herat, Afghanistan, that three years later is the largest private employer of Afghan women in the world, with over 2000 women employees. In May 2017, Mark Cuban became an investor in Rumi Spice. In September of 2018, Rumi Spice’s saffron became available nationwide in all Whole Food Markets. Shawn is a native of Sioux Falls, SD, and credits his very patient wife — Dr. Jennifer Jacobs, his Mother, Jan, his brother, Shane, his South Dakota roots, and mentors and friends like Aaron Walters, Amit Yoran, Paul Garrett, Fraser Verrusio, Jeff Cesnik, Mischel Kwon, Kendall Millard, Gary Golomb, Paul Kurtz, Dave Haugen (his high school band director) and many, many others for his scrappiness, successes and ability to recover from failures.

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About CityVest, Crosscut Ventures, Crosscut Ventures, Global Foundry, InAuth, Left Coast Ventures, PeerNova, Privateer Holdings, Rumi Spice, StealthWorker, ThreatGRID, Three Tree Ventures, Tilray: Three Tree Ventures is an early stage VC firm that invests in startups that are applying technology to disrupt the market status quo.

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