Team

With a deep appreciation for leadership, team-building, and the soft side of hard tech, Squadra Ventures is itself a team of founder-operators who believe that exceptional teams are the key to outsized success.

After nine years as an Army intelligence officer, with deployments to Iraq and Afghanistan, five years as a Founder-CEO of a bootstrapped IT services firm, and five years as a Founder-CEO of a venture-backed cybersecurity product company, Guy Filippelli started Squadra Ventures in 2019 with the goal of building the world-class venture fund and partner that he’d wish existed when he was raising capital.

As a result, we invest in highly vetted early stage deals, from our expansive network, and only when we know we can make an unfair contribution beyond capital — where we can dominate, create value, and grind. We do that as a squad.

Meet your people.

Guy Filippelli

Managing Partner

Founder, investor, mentor, and board member. Former Army intel officer with a deep sense of patriotism and a strong believer in integrity. Obsessed with helping entrepreneurs build and run great companies — and making the connections that truly move the needle. Passionate about food, wine, and all things Italian. Perhaps one of the world’s greatest Italian genealogists. Epic bread baker.

Margaret Roth Falzon

Chief Operating Officer

Spent six years building a customer-focused analytics startup and developing the process, tools, and culture needed to scale the business. Ready to work with our portfolio companies as they grow and scale while fostering diverse, equitable, and inclusive cultures. Reader of science-fiction, lover of puppies, consistent arguer that all you need to know about starting a company is contained in Cameron Crowe’s masterpiece Almost Famous.

Chip Gaskins

Principal, SPV

Entrepreneur, founder, investor, partnership driver, team member, M&A, little league baseball coach. Buxton Capital, DigitalBridge, HiBeam, Mainstreet Broadband, AOL, Intel Capital, Cortland Advisors, Veretus. Living in DC with his two children, volunteer with Special Olympics of Montgomery County, Thrive DC women’s shelter, and helping assist students at American University and Georgetown University with new business ventures. Tar Heels not Dukies.

Dan Madden

Principal, National Security

Former Marine, Congressional staff, and think tank alum. Passionate about bringing outstanding tech to those going into harm’s way. Focused on supporting startups ready to do something big for our national security. Side hustle teaching at Columbia University. Hiking with the family or reading military history with the obligatory glass of scotch whenever I can.

Heather Strelczyk

Portfolio Operations Associate

Spent the past six years in asset and operations management working with dynamic companies to create meaningful change, including non-profit fundraising for a relief organization. Excited to expand portfolio operations, cultivate and grow our advisor network, and help our portfolio companies reach new heights. Military spouse who loves to travel and explore, get immersed in local culture and cuisine, and host of the book club Random Readers.

Isaac Carp

Investment Associate

Spent four and a half years in financial services on the sell and buy-side as a trader and an analyst. CFA charterholder, now earning his MBA at Georgetown University’s McDonough School of Business to enter Venture Capital. Transitioning from stocks and bonds to investing in extraordinary people and ideas. From Boston, but does not pronounce “car keys” as “khakis”. Sports lover, charcuterie connoisseur, dog whisperer. Strong believer that energy is contagious.

Div Goel

Investment Associate

Spent five years consulting banks, FinTechs, and payment providers on performance improvement and strategic growth initiatives. A persistent learner who is driven by innovation and passionate about supporting entrepreneurs in taking their company to the next level. Dog lover, aspiring world explorer, and occasional poet who keeps an assortment of sneakers and basketballs in the trunk of his car.

Leo Holland

Portfolio Operations Analyst

Recently graduated from Wesleyan University with majors in Economics and History, and currently a Venture For America Fellow. A passion for entrepreneurship and innate intellectual curiosity helps motivate growth amongst portfolio companies and cultivate a keen eye for disruption. A Cleveland native that thinks every year is the Browns year. Skier, Lego master, and local history buff.

Heather Ichord

Venture Advisor

Loves serving people, and leading operations and logistics (planes, trains, and automobiles). Big believer in cumulus-cloud-thinking turned color-coded sticky notes. Curious about innovations that drive us forward, together. Completed grad degrees part-time on Saturdays and at 2 AM to Hans Zimmer soundtracks. Ultra-runner. Fiercely devoted to two sweet Labradors.