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, exclusively invests in product companies, and prefers to invest in organizations with one or more U.S. military veteran founder(s). Shawn is also an LP and Advisor to CrossCut Ventures (https://www.crosscut.vc) located in Los Angeles, CA (6+ years). Mr. Carpenter is a globally respected cyber security expert with a broad range of successful early-stage investments, including Compass, GroupSense, White Ops (acquired by Goldman Sachs Merchant Banking), Dark Cubed, uSTADIUM, PeerNova, MILLIE, Rumi Spice, Awake Security (acquired by Arista Networks), Privateer Holdings (acquired by TILRAY), ThreatGRID (acquired by Cisco Systems), RideScout (acquired by Daimler AG), InAuth (acquired by American Express) and Efflux Systems (acquired by NETSCOUT Systems). Mr. Carpenter is known for his acumen for advising early stage innovators. He has successfully helped raise capital, navigate rough waters, acquire key talent and customers, and help develop short and long-term strategies for portfolio companies and startups that he advises. He is currently an Advisor to CrossCut Ventures, Trinity Cyber, TruSTAR Technology, GroupSense, uSTADIUM, MILLIE, Blackwatch Digital, and Netswitch Technology Management. He has held key positions at startups where he was an early employee — Principal Forensics Analyst at NetWitness Corporation (acquired by EMC/RSA), Chief Technical Analyst at iSIGHT Partners (acquired by FireEye), Chief Strategy Officer at Invotas (aquired by FireEye), and Senior Vice President of Cyber at Cybraics. One of his greatest 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 non-profit is applying modern technologies like artificial intelligence and data science to the foster care system in the United States to improve placement outcomes -- finding forever families for thousands of children in the system. 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 U.S. Navy, and qualified as a nuclear operator and chemist during his six years of service in the U.S. 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. He discovered one of the first documented penetrations of U.S. Government networks. After joining NetWitness as one of the first employees, he helped architect, implement and stand up the Justice Security Operations Center (JSOC) — at the time the largest deployment of NetWitness gear for a federal client. Mr. Carpenter also worked as a Principal Senior Analyst at the U.S. 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 (https://apps.nsa.gov/iaarchive/programs/rowlett-awards/recipients.cfm). Mr. Carpenter has been tinkering with computers since his mother bought him 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, harmonica, banjo and trumpet, metal detecting with his kids, building forts high in tall trees, lucid dreaming, experimenting with brain/machine interfaces, building robotics projects with his kids, 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 being the first money in at Rumi Spice (https://www.rumispice.com), a sustainable saffron growing enterprise founded by three West Point graduates, to PeerNova, a blockchain startup founded by his CS251 instructor from University of Nebraska. Five years after investing in Rumi Spice, it is now the largest private employer of Afghan women in the world, with over 2000 women employees. In May 2017, Mark Cuban became an investor in the saffron startup. 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 Mother, high school marching band instructor, David Haugen, South Dakota roots, and industry mentors and friends like Aaron Walters, Amit Yoran, Dug Song, Gary Golomb, Chris Lukas, Sean Catlett, Richard Stiennon, Paul Garrett, Fraser Verrusio, and many others for his scrappiness and successes.

Shawn Carpenter

Founder

23 past transactions

KeyCaliber

Seed Round in 2021
Developer of an automated security program assessment and optimization platform designed to identify mission-critical assets and the pathways to and from these assets. The company's platform leverages existing cybersecurity telemetry and advanced data science techniques to automatically identify and classify critical assets, determine the cyber risks and security controls for these assets, and recommend ways to reduce risks and minimize costs associated, enabling clients to replace spreadsheets and manual processes with data science and automation.

Clocr

Pre Seed Round in 2021
Clocr is a comprehensive digital legacy planning and disbursement platform designed to help individuals secure and manage their online accounts and digital assets. The platform allows users to organize vital documents and information in a secure manner, enabling them to designate beneficiaries who can access these assets in the event of an emergency or death. Clocr features a digital safety deposit box that employs advanced encryption and security measures, ensuring that sensitive files are protected. Its user-friendly interface facilitates estate planning, including the creation of wills and the execution of necessary documents, all while adhering to legal compliance. Clocr's unique, patent-pending security approach utilizes innovative technologies to safeguard encrypted files, distributing them across multiple cloud storage locations to enhance protection against unauthorized access. This all-in-one solution stands out by offering extensive legacy planning features and robust security, streamlining the process of passing on digital assets to heirs.

BarTrack

Seed Round in 2019
BarTrack Inc. designs and manufactures sensor-enabled smart tap to pour beer. Its platform uses a beverage sensor that standardizes draft systems by continuously monitoring beer-specific variables and alerting when anomalies occur. The company also provides a smart faucet. The company’s products help to avoid wastage of beer due to over-pouring and foam filling. Its products are used by bar owners, managers, and bartenders to standardize draft beer quality. The company was founded in 2018 and is based in Sterling, Virginia.

Awake Security

Venture Round in 2017
Awake Security, Inc. specializes in network traffic analysis, providing a platform that autonomously identifies, assesses, and processes threats within network environments. The Awake Security Platform utilizes advanced technologies, including federated machine learning and threat intelligence, to analyze extensive communications, enabling it to discover, profile, and classify every device, user, and application on a network. This capability allows the platform to detect malicious intent from both insiders and external attackers while offering full forensic context for behavioral and compliance incidents. Additionally, Awake Security delivers security strategy, operations, and advisory solutions. Founded in 2014 and based in Santa Clara, California, the company operates as a subsidiary of Arista Networks, Inc. since October 2020.

Falls Church Distillers

Pre Seed Round in 2017
Falls Church Distillers is licensed in Virginia to be an active distiller. In addition to straight bourbon, the 3,400 square-foot family operation makes premium traditional gin, citrus-infused gin, and pineapple-flavored gin as well as regular and pepper vodka. The premises also has the unique arrangement of their own ABC on-premise store, where patrons can purchase bottles of spirits. Also on tap are local beers and a selection of Italian wines paired with small plates like antipasti, bruschetta, panini sandwiches and honey mascarpone fig gelato.

Dark Cubed

Seed Round in 2017
Dark Cubed brings security to the more than 99% of companies that do not have the resources to implement security today. Our SaaS solution augments existing firewalls to provide enterprise-grade security capabilities at a fraction of the cost and complexity of other solutions. We partner with MSPs and service providers to secure their customer base, increase revenue, and capture new customers.

GroupSense

Seed Round in 2016
The intelligence space is filled with search tools, feeds, and briefings. It is difficult to measure the value and sift through the noise. GroupSense offers a unique partnership based approach to an intelligence program tailored to your mission. Our Cyber Reconnaissance solution is a combination of highly scalable technology with experienced intelligence analysts, providing only meaningful, high fidelity, intelligence data. Groupsense is changing the way cyber intelligence is delivered and operationalized across mid to large enterprises and governments. Our Recon Services provide critical action oriented data that helps protect the worlds largest networks, critical intellectual property, and election integrity.

Efflux Systems

Seed Round in 2016
Efflux Systems, Inc. provides cyber security solutions. It offers Threat Discovery System that turns the tables on hackers by arming network defenders with an integrated toolset that automates threat discovery processes. The company was incorporated in 2013 and is based in Millersville, Maryland. As of July 12, 2017, Efflux Systems, Inc. operates as a subsidiary of Arbor Networks, Inc.

Actev Motors

Pre Seed Round in 2016
Actev’s first product is a very cool electric go-kart for kids, but that’s just the beginning. Leveraging the technology and supply chain we developed, we’re now creating a modular drivetrain for robots. The drivetrains in most of today’s robots are inadequate for high volume manufacturing and emerging safety standards. Our rugged and cost-effective drivetrain modules will be used to build a wide range of robots and small electric vehicles. Just as Bosch became the leader in automotive drivetrains, Actev aims to become “the Bosch of Robots”.

StealthWorker

Seed Round in 2016
Stealth Worker specializes in Cyber Security. Rather than hiring for full-time employment roles, their Stealth Workers are contractors. You can hire them for projects or long term roles, from as little as 5 hours to as many as 40 hours per week.

CityVest

Convertible Note in 2016
CityVest is an on-line marketplace providing individual accredited investors with access to institutional quality real estate investments. The goal is to provide the simplest and best real estate investment process for individual investors, as well as providing efficient access to capital for sponsors. The CityVest.com website provides individual investors with the opportunity to browse real estate investments, conduct due diligence on the properties, and review investment documentation. The on-line closing process is simple and safe. By pooling investments of as little as $10,000 with other investors, individuals can now gain access to high return institutional quality deals. CityVest targets providing investors with relatively safe real estate investments with a 7% to 10% preferred return and a 15% to 25% IRR. Sponsors who are seeking capital for their deals also benefit as they can raise capital for their transactions in less time and without several layers of fees. Their existing investors include the Chairman of JP Morgan Private Bank Asia, the Chairman of a NYSE company, the Chairman of a NASDAQ company and the former President of a Goldman Sachs subsidiary. There is huge interest in real estate crowdfunding which has attracted real estate moguls such as Larry Silverstein, Andrew Farkas, Simon Ziff and Jared Kushner, as well as real estate firms SLGreen, Vornado, and Guggenheim. The market is massive with over $20 billion raised each year through traditional Reg. D private placement syndications for real estate deals. The 2,000 annual private placements are still done the old method of syndicators calling equity investors, sending pdfs of documents, and laboriously managing wire transfers. CityVest makes raising equity capital for real estate deals easy and fast.

Rumi Spice

Seed Round in 2015
Rumi Spice is a Boston-based company founded in 2014 that specializes in producing and selling saffron and other spices, including black cumin, spice blends, and gift sets. The company is committed to ethical sourcing and social responsibility, directly connecting consumers with Afghan farmers to promote sustainable rural economic development. By providing employment opportunities for women who harvest and process the spices, Rumi Spice aims to empower local communities and foster economic growth in Afghanistan. The company reinvests its profits to enhance agricultural and manufacturing infrastructure, contributing to a foundation for peace and prosperity in the region. Products are available through an online retail portal, allowing customers to access high-quality, culturally significant spices while supporting meaningful change.

Privateer Holdings

Series B in 2015
Privateer Holdings, Inc. is a private equity firm based in Seattle, Washington, with additional offices in San Francisco, Newport Beach, and Denver. Founded in 2010, the firm specializes in investments in the legal cannabis sector, focusing on incubation, seed funding, and various stages of venture capital, including emerging growth and buyout opportunities. Privateer aims to build a portfolio of global brands that will define and legitimize the future of cannabis, with notable investments including Leafly, a leading cannabis information resource, and Tilray, a prominent producer of medical cannabis. The firm represents a coalition of investors committed to advancing the legal cannabis industry while addressing the social issues associated with cannabis prohibition.

AgentHero

Seed Round in 2015
AgentHero, Inc. operates an online platform specifically designed for military families to assist them in their home search, particularly during Permanent Change of Station (PCS) moves. Founded in 2014 and based in Arlington, Virginia, the company connects military families with a network of experienced real estate agents, including veterans and military spouses, who are committed to providing honest and reliable service. AgentHero offers various support services, including assistance with long-distance rentals and homebuying consultancy, ensuring that military families can make informed decisions about their housing needs. The company's approach emphasizes collaboration with multiple brokerages to access a diverse range of agents, highlighting their shared values of integrity and dedication to service.

PeerNova

Series A in 2014
PeerNova® is a digital transformation company with a mission to empower financial institutions to unlock their data, increase efficiency, and discover opportunities. Cuneiform® is PeerNova’s zero-code platform that automates data quality, end-to-end (E2E) visibility, and process correctness. Through continuous high-quality data and event lineage, the Cuneiform Platform enables firms to increase operational efficiency, improve business performance, and address executive, stakeholder, and regulatory inquiries confidently and promptly. Founded by entrepreneurs with deep expertise in data and financial infrastructure, PeerNova is a Silicon Valley technology company with sales offices in New York and London. For more information about PeerNova, visit https://peernova.com.

Compass

Series B in 2014
Compass is a real estate brokerage company based in New York City, founded in 2012 by Ori Allon, Robert Reffkin, and Ugo Di Girolamo. The company offers a comprehensive platform for residential real estate agents, equipping them with a suite of cloud-based software tailored for customer relationship management, marketing, and client service. This integrated approach enhances the ability of agents to provide exceptional service to buyers and sellers. In addition to its brokerage services, Compass has developed a mobile app for iOS and Android that facilitates buying, selling, and renting homes across the United States. The company operates primarily within the domestic market.

InAuth

Seed Round in 2014
InAuth is a digital device intelligence company for a mobile-first world. It delivers the most advanced device identification, risk detection, and analysis capabilities possible to help organizations limit risk, remove friction, and reduce fraud within their digital channels. With safer digital transactions, banks, payment networks, merchants, healthcare providers, governments, and other organizations are better positioned to capture new revenue opportunities and compete more effectively in an “always-on” world.

RideScout

Convertible Note in 2014
RideScout is a technology platform that provides a comprehensive solution for ground transportation by aggregating public, private, and social rideshare options on its free mobile applications for both iOS and Android. Users can search and compare various transportation modes—including transit, taxi, rideshare, bike share, carpooling, walking, biking, driving, and parking—through a single interface. This innovative approach allows for real-time access to multiple transportation options, making it easier for individuals to find the most suitable means of travel. Headquartered in Austin, Texas, RideScout also operates an office in Washington, D.C., contributing to its mission of simplifying transportation choices for users.

HUMAN

Convertible Note in 2014
HUMAN is a cybersecurity company focused on safeguarding enterprises from bot attacks, thereby enhancing digital experiences for genuine users. The company employs its advanced Human Verification Engine to protect applications, APIs, and digital media from malicious bot activity, which can lead to significant financial losses and degrade user experience. HUMAN verifies over 10 trillion interactions weekly for major companies and internet platforms, ensuring that digital engagements are legitimate. Its solutions cover a range of sectors, including advertising, publishing, and enterprise, addressing various threats such as automated fraud, data scraping, and account takeovers. Founded in 2012 and headquartered in New York, with additional offices in Washington, D.C., London, and Victoria, HUMAN continues to innovate in the field of online security.

Compass

Series A in 2013
Compass is a real estate brokerage company based in New York City, founded in 2012 by Ori Allon, Robert Reffkin, and Ugo Di Girolamo. The company offers a comprehensive platform for residential real estate agents, equipping them with a suite of cloud-based software tailored for customer relationship management, marketing, and client service. This integrated approach enhances the ability of agents to provide exceptional service to buyers and sellers. In addition to its brokerage services, Compass has developed a mobile app for iOS and Android that facilitates buying, selling, and renting homes across the United States. The company operates primarily within the domestic market.

ThreatGRID

Seed Round in 2012
ThreatGRID is the first unified malware analysis and threat intelligence solution that is revolutionizing how organizations use accurate and context-rich intelligence to defend against advanced cyber attacks. ThreatGRID securely crowdsources large volumes of malware and performs advanced analysis in the cloud, to identify key behavioral indicators enabling near real-time remediation. ThreatGRID empowers security teams with continuous real-time threat intelligence, enriched by global and historical context, to prevent future attacks. ThreatGRID’s API simplifies sample submission and intelligence integration with other security products to maximize the effectiveness of existing investments.