MILCOM Founders Podcast – Episode 32: From Campaign Trail to Headshot Excellence with Jon Meadows
Join host Rod Loges and guest Jon Meadows as he shares his journey from political communications to founding High-End Headshots, a premium photography business specializing in professional headshots. Jon discusses how getting fired became the catalyst for building a thriving business that serves executives, professionals, and veterans across the DC area.
In this episode:
- Jon’s transition from political campaigns to full-time photography entrepreneur
- How a $20/month online mentorship transformed his career trajectory
- Getting fired with a 9-month-old at home and launching a business the same day
- Building a premium pricing strategy that values quality over volume
- The importance of hyper-focus and single-mentor learning systems
- Giving back through annual $50,000 headshot giveaways for veterans
Key takeaways:
- Specialization creates competitive advantage – Jon focused exclusively on headshots rather than general photography
- Pricing psychology matters – aspiring to be “the best and most expensive” creates client respect and work-life balance
- Faith and stewardship drive business decisions, not just profit
- Following one proven system beats collecting advice from multiple sources
- Professional headshots create human connection and trust before you ever meet someone
- Being a “net exporter” means using your gifts to produce more than you need so you can give to others
Guest: Jon Meadows, Founder of High-End Headshots, Former Political Communications Professional
- LinkedIn: https://www.linkedin.com/in/highend/
- Business Website: https://highendheadshots.com/
Jon Meadows runs High-End Headshots, a premium photography business in the Washington DC area with over eight years of experience. Known for his facial expression coaching approach, he’s earned the reputation as “the last hope for the non-photogenic” and helps clients “wow themselves” with professional imagery that creates trust and human connection.
Jon’s path to entrepreneurship began on political campaigns, where he worked long hours in communications roles. After his mom noticed his compositional eye from study abroad photos, he picked up photography as a side pursuit. When he was unexpectedly fired from a nonprofit job in 2018 with a 9-month-old daughter at home, Jon went full-time with his photography business that same day. He found mentorship through the world’s best headshot photographer for just $20/month and built a thriving business based on premium pricing, hyper-focus, and exceptional client experience.
Beyond his business success, Jon is a husband to Katie for 10 years, father to four kids under nine (two boys and two girls, “which was the master plan”), and an avid racket sports player who’s recently gotten into pickleball tournaments. He’s also a man of deep faith who views his business as stewardship – using his gifts to be a “net exporter” who can give generously to his church, school, family, and community.
Looking ahead: Jon continues to refine High-End Headshots while maintaining the work-life balance that allows him to be present for his young family. Each year, he gives away approximately $50,000 worth of headshots to veterans and those transitioning out of military service, turning his craft into a way to serve those who served.
The MILCOM Founders Podcast champions and celebrates military community business owners. Each episode brings practical insights and lessons learned from successful veteran entrepreneurs and those who serve the military community.
Sponsored by One Degree Financial www.onedegreefinancial.com
Want to support veteran entrepreneurs? Learn about the Dick Loges Veteran Entrepreneur Scholarship Fund at https://www.milcomfounders.com/