Jonathan Miller: Making Good on his Commitment to Ensure Soldiers’ Welfare

Welcome back! Spiffy here, your interplanetary journalist reporting from Planet Earth with an eye on entrepreneurs impacting the world of work. Today’s rockstar is giving back to the soldiers that risked their lives to serve their country. I’m thrilled to introduce Jon Miller, US Army veteran and founder of Outlaws Inc.

Spiffy: I’m eager to learn about Outlaws Inc., Jon! What challenges are you addressing?

Jon: I founded Outlaws Inc. for the explicit purpose of serving two at-risk populations that I care deeply about and are central to American society — young transitioning veterans and skilled-trade small businesses. Through our dual mission, we help young veterans chart a path to long-term success, and we strengthen small businesses and the communities they serve. When we think holistically about our approach, we also hope our efforts will contribute positively to addressing a broader set of problems affecting these two communities. 

Spiffy: Wow, Jon, that must have required quite a vision. What motivated you to tackle this?

Jon: Well Spiffy, I served in the Army for eight years as an infantry officer before pursuing my MBA at the Yale School of Management. During my first year of graduate school, one of my former soldiers committed suicide.  At the funeral, I reunited with many of my former soldiers and noticed that, with few exceptions, they were all struggling with their transitions to civilian life.  I wondered if I could combine the leadership lessons of my service with a mission-driven business model to create pathways to success for the youngest veterans. When I returned from the funeral, I founded Outlaws Inc., named in honor of the platoon I served with. I have been working on this startup as a solo founder ever since.

Spiffy: That’s amazing! Tell me more about how Outlaws Inc. is making the world a more equitable place.

Jon: We empower veterans to build wealth, learn new skills, and gain experience in resilient industries. Our immediate goal for employers is to increase the economic potential of their small businesses. Grounded in strong values and committed to people, we aren’t just filling vacancies; our aim is to contribute to addressing broader societal problems facing the communities we care about. While our mission is focused, we hope that our services can contribute to reducing persistent joblessness, substance abuse, homelessness, and suicide among veterans. 

Spiffy: What kind of recent milestones have you achieved?

Jon: We recently completed our first veteran–employer match, chronicled by this video. This proves that our model of tailored mentorship for veterans and employers is worth pursuing, even if it takes longer to turn a profit than conventional business models.

Spiffy: Tailoring is not a thing of the past, that’s for sure! Have you experienced any failure? And what did you learn from it?

Jon: I've applied to about a dozen grants and funding sources and was only accepted to one. Most people want to know how I'm going to scale, and I've remained committed to the mission first. All told, I'd say that I've failed more than I've succeeded thus far, but that's just the nature of startups.

Spiffy: Is there anything else you’d love for our audience to know?

Jon: Yes, Spiffy! If anyone wants to learn more about Outlaws Inc., they should check this out.

Spiffy: I’m going to head there right now! Thanks for sharing your vision and exciting work with us, Jon. It’s been an honor.