Inside Startups: Tools, Tactics, and Takeaways

Veteran Entrepreneurship: Women Veterans Leading the Way

Written by Jeremy Willis | Jun 20, 2025 8:30:00 PM

Dive into the remarkable journey of retired Lieutenant Colonel Johanna Wynne—a visionary US Army veteran redefining what’s possible in startup entrepreneurship. Experience firsthand how she navigates and overcomes the distinctive challenges of this path, inspiring a new generation of leaders.

The Rise of Women Veterans in Entrepreneurship

Women veterans are increasingly becoming a significant force in the startup world, leveraging their unique experiences and skills gained during military service. These trailblazers are not only breaking barriers but also setting new standards in entrepreneurship.

With a mission-driven mindset and a capacity for adaptability, women veterans are well-equipped to navigate the dynamic landscape of startups. Their stories of resilience, leadership, and innovation serve as powerful examples for aspiring entrepreneurs everywhere.

Lessons from Army Futures Command: A Startup Within the Army

One of the most fascinating insights from the recent Startup Anthology episode comes from Johanna Wynne's experience with the Army Futures Command. This initiative was akin to running a startup within the vast and structured environment of the military, emphasizing innovation and breaking down silos.

Wynne shared how the command's culture encouraged new ways of thinking and operating, akin to the entrepreneurial spirit found in civilian startups. This environment required comfort in discomfort and a willingness to challenge the status quo, qualities that are essential in both military and startup settings.

Navigating the Transition: From Military to Startup Life

Transitioning from military life to the startup world can be challenging yet rewarding. Johanna Wynne's journey exemplifies this transition. After serving 20 years in the Army, she jumped into the startup ecosystem, bringing with her a wealth of experience and a fresh perspective.

Wynne's story underscores the importance of finding a role that aligns with one's values and passion. While her initial foray into a startup didn't go as planned, the lessons learned were invaluable. This transition phase is crucial for veterans, offering them an opportunity to redefine their career paths and apply their military-honed skills in new, impactful ways.

Overcoming Unique Challenges: Insights from Johanna Wynne

Women veterans face unique challenges as they transition into the civilian workforce and entrepreneurial roles. Johanna Wynne highlighted how her military background sometimes led to heightened scrutiny, but also how it equipped her with resilience and a strong sense of purpose.

Wynne emphasized the need for passion and buy-in when joining a startup. Her experience taught her that being fully invested in the mission is critical for navigating the inevitable ups and downs of entrepreneurial life. Her insights serve as a valuable guide for other women veterans looking to make their mark in the startup world.

Building a Supportive Community for Women Veteran Entrepreneurs

Creating a supportive network is vital for women veteran entrepreneurs. Events like the Military Connected Mentorship Meetup, co-hosted by Jeremy Willis, provide a platform for veterans to share their experiences, learn from each other, and build valuable connections.

Wynne’s story also highlights the importance of community. She has found solace and strength in connecting with other women veterans who understand the unique challenges faced during and after military service. These communities offer not just support but also opportunities for collaboration and growth, helping women veterans to thrive in their entrepreneurial pursuits.