From Side Hustles to Startups: Dev Chandra’s Journey from Navy Vet to VC Builder

In this episode of TheMilVet Podcast, host Beau Higgins sits down with Dev Chandra, Founder of Startup Intros, Associate at Context Ventures, a U.S. Navy veteran, serial builder, and venture operator. Dev shares his entrepreneurial journey, beginning with side-hustling as a digital consultant while in the Navy, transitioning into government consulting with Booz Allen Hamilton, and later returning to the startup world with a focus on AI and early-stage ventures.

He reflects on the lessons learned from navigating a solo consulting business after military service, and how his time at Booz Allen provided valuable structure and insight. That experience, combined with a growing interest in AI automation, reignited his drive to innovate and build within the startup space.

Dev also explains how he became involved in veteran founder and investor networks, including his work with Start Venture and his engagement with the veteran-led community at Context Ventures, which supports military-affiliated entrepreneurs. Through these efforts, he has focused on bridging knowledge gaps for founders by leveraging AI-powered tools and expanding access to defense and dual-use markets.

Throughout the conversation, Dev emphasizes the importance of learning by doing, showing up to opportunities, and tapping into the power of veteran communities. His perspective serves as both tactical advice and inspiration for veterans interested in startups, venture capital, or defense technology.

Tune in to learn about:

• Dev’s path from Navy service to consulting and entrepreneurship
• How his time at Booz Allen helped shape his professional reinvention
• The role of veteran networks in supporting founders and innovators
• Insights into government consulting and private-sector transitions
• Ways AI-powered tools might reduce challenges faced by early-stage startups
• Practical steps for veterans interested in breaking into technology, venture, or startups
• Why showing up to conferences, hackathons, and coffee chats can change your trajectory
• The value of mentorship, collaboration, and building with community

Whether you're a transitioning service member, an aspiring founder, or curious about where military experience intersects with entrepreneurship and AI, this episode offers grounded insights and actionable advice.

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