Guy founded Squadra Ventures in 2019 with the goal of building the world-class venture fund and partner that he wished had existed when he was raising capital. He leads Squadra’s investment and portfolio operations efforts and serves as board member for Squadra’s portfolio companies.
He was the founder and CEO of Red Owl Analytics, a Baltimore cybersecurity analytics startup focused on mitigating insider threat risk, which was acquired by ForcePoint, a Raytheon subsidiary in 2017. He was also founder and CEO of Berico Technologies, a Virginia consulting firm that delivered innovative, technology-enabled cloud engineering, data analytics, and IT modernization solutions to customers in the Intelligence Community. Berico was acquired by Novetta in 2018.
He began his career as a US Army intelligence officer, serving in Korea, Italy, Germany, and Afghanistan, and at the NSA. Guy holds a B.S. in Economics from the United States Military Academy (USMA) at West Point, and received his B.A. and M.A. in Philosophy, Politics, and Economics from Oxford University, where he studied as a Marshall Scholar.
He is Chairman of the Commit Foundation, a non-profit focused on veteran transition, and serves on the board of the National Cryptologic Foundation.
Margaret leads the Squadra Portfolio Operations team, working with portfolio companies to accelerate and resource key strategic initiatives, support as an internal expert consultant, and develop the leadership capacity of the teams. She also manages fund operations and administration.
She was a co-founder Yet Analytics, a data interoperability and analytics company that provides software products to enterprise learning and training organizations across government, industry, and academia.
Margaret began her career as a whitewater kayaking instructor turned teacher in Baltimore City Public Schools, and was then part of the startup team at the Digital Harbor Foundation. It is through these experiences that her obsession with the development of organizations as teams of leaders formed and continues to grow.
An avid writer, Margaret’s work has been featured in leading industry publications, at national conferences, and in a regular founder-focused column for Technical.ly. She received a BA in English & Environmental Earth Science and an MA in Teaching from Johns Hopkins University.
Margaret serves as the Board Chair of the Emerging Technology Center, an initiative of the Baltimore Development Corporation.
John leads Squadra’s finances, compliance, and fundraising efforts. He is responsible for working with investors, valuing the Squadra portfolio, and supporting our founders as they professionalize their financial reporting and prepare for future raises.
John brings deep venture capital and private equity expertise to the fund with 13 years of experience in management, mergers & acquisitions, corporate finance, investment management, and strategic planning.
He previously served as the Director of Business Development at Camden Partners and a Portfolio Manager at Cornerstone Advisory.
He received his BA focused in Business Management and Economics from Washington College. John spends time trying to lower his golf handicap and cheering his kids on at sports games.
Dan leads Squadra’s National Security practice, sourcing and evaluating companies for investment and supporting post-investment work on federal go-to-market strategy.
Dan served as the Mid-Atlantic Regional Director at the National Security Innovation Network, the Department of Defense’s national security technology accelerator. He previously was a senior policy analyst at the RAND Corporation, conducting capability development and campaign assessment studies for the Department of Defense, helping to inform the Department’s modernization and planning efforts.
Prior to these efforts, Dan was an artillery officer in the United States Marine Corps, worked as military legislative assistant to the Oversight and Investigations Chair on the House Armed Services Committee, and served as special assistant to an Under Secretary of Defense. Dan is a visiting scholar at Columbia University's Entrepreneurship Program, and an adjunct associate professor at Columbia University’s School of International and Public Affairs.
He received a BA in English Literature from the US Naval Academy, a MA in Political Science from Columbia University, and a MA in Comparative Politics from University of California, Davis. He loves hiking with his family and reading military history.
Adam leads Squadra’s Cybersecurity practice overseeing the sourcing, diligence, and investment decisions in cybersecurity technology startups and supporting go-to-market and product roadmap strategy post-investment.
He is an evangelist for good product management and loves helping founders align engineering capacity, market demands, and business goals.
Adam was co-founder and chief product officer of Morta Security which was acquired by Palo Alto Networks in 2014, and co-founder and COO of Efflux Systems which was acquired by Netscout in 2017. He most recently served as the Global Head of Third Party Cyber Risk Products & Services at Maryland cybersecurity unicorn BlueVoyant, where he led product expansion and market growth acceleration.
Adam’s career started in the United States Air Force, where he spent more than two decades on both active duty and in the reserves, as an operator, technologist, and cyber warfare expert. His efforts began in predecessor organizations to US Cyber Command, later supporting Air Force cyber mission growth.
Adam received a BS in Information Sciences from the University of Pittsburgh and an MBA from the University of Maryland. In his spare time, he coaches his kids’ hockey teams and races old BMWs.
Arianne works with Squadra portfolio companies to design and execute their go-to-market strategy, grow their revenue, and increase relevance through media and government relations.
She spent the early years of her career on the Hill. She served as the scheduling and operations director for Senator Kyrsten Sinema's winning 2018 campaign, electing the first woman senator in Arizona history and raising over $30M dollars.
She most recently led operations for Squadra portfolio company Sicura and brings operations management and communications experience from her early career in government and political campaigns.
Arianne received her BS in International Affairs and her MBA from Georgetown University and enjoys seeing live music and theater, volunteering for political campaigns, and reading tarot cards.
Stephen works to grow the Squadra brand through content, PR and events. Working closely with the Squadra team and portfolio companies, he tells stories, builds audience and makes the creative a driver of value.
Stephen has built new media products across B2B and general interest news. Most recently, he built, launched and served as editor of The Current, a B2B media platform for ecommerce professionals, and supported the marketing and brand activities of parent company Incremental, a retail media attribution and measurement platform.
Over a 15-year career as a journalist across print and digital, he worked as an editor with outlets such as the tech news network Technical.ly, and a reporter with publications such as The New York Times, NOLA.com | The Times-Picayune, The Rio Grande Sun and The Patriot-Ledger.
He received a BS in Journalism from Northeastern University, and is a proud resident of Baltimore City.
Isaac co-leads deal sourcing, due diligence, and evaluation of Squadra investments with a focus on understanding company markets and opportunities and modeling out wins.
He previously worked on both the sell-side and buy-side as a trader and an analyst within equities and fixed-income in the public markets.
He received his BS in Management & Business from Skidmore College and his MBA from Georgetown University. A Boston native without the accent, Isaac is an avid runner and reader.
Amy manages Squadra’s events, calendars, and administrative processes, bringing order to chaos.
She previously spent 10 years supporting the President of All Risks, Ltd.
Amy received her BS in Business and Marketing from Colorado State University and will never stop calling Colorado home. She loves sports, whether playing volleyball or cheering on her kids at their games.
Navneet supports our investment team on national security and cybersecurity deals. A former strategy consultant, he has led modernization efforts for DoD stakeholders in transformation efforts across readiness, intelligence, industrial security, technology, and cybersecurity arenas.
Navneet has also worked with the National Security Innovation Network to jumpstart the development of regional technology ecosystems and create pathways for early-stage startups and investors to work with DoD.
Navneet received his BS in International Economics from Georgetown and is an MBA Candidate at Columbia University, and is an avid runner, golfer, chef, and Yankees baseball fan.
We stand by our teams, from the beginning to the exit. We think as “entrepreneurs first” so that we can understand their decisions from a place of empathy. We invest completely with our time, capital, resources, network, and community. We double-down on everybody.
We manage ourselves with a team of teams approach to invest, accelerate growth, and create value. With our strong internal team, expansive network of venture partners, operators, and service partners, we transform our companies through fierce loyalty, authenticity, and a drive to win over and over again together.
We communicate, document, and collaborate openly as a team internally and with our portfolio companies. We believe that sharing access to information and data in process, unfiltered, increases understanding, builds trust, expands the impact of our collective intelligence, and enables us to move faster with unparalleled accuracy.
We invent, iterate, and invest in tools, processes, and systems that enable us to have an outsized impact and unmatched influence in our communities and networks. We do the work. We do whatever it takes to win the right deals and grow our companies.
We recognize that the entrepreneurs are the ones holding the risk on their shoulders. We bring humility and positive energy in our role as supporters, observers, advisors and partners in the journey, even when we say no.
We dedicate our time and effort to the communities we care about regardless of the quantifiable impact they have on ourselves. We believe that when you put good out into the world it comes back one way or another, everything is one thing.
We hold ourselves accountable. We hold each other accountable. We hold our entrepreneurs and teams accountable. But we also enable our entrepreneurs to hold us accountable for what we say we are going to do. There is no hierarchy, we are jointly accountable.