Founder & Managing Partner

Jonathan Gattman founded Western Trail Capital after a 25-year career in value investing, during which he diligenced thousands of companies and led investments across public and private markets. He brings a disciplined, fundamentals-driven approach to evaluating and supporting specialized outsourcing businesses.

Before Western Trail, Jonathan founded and managed Cloverdale Capital, a $200 million small-cap value hedge fund that consistently outperformed its benchmarks. Earlier in his career, he served as a Managing Director at Highside Capital Management, a Dallas-based multi-billion-dollar hedge fund, where he invested in technology, business services, healthcare, and consumer companies.

Jonathan also has a decade of experience applying value-investing principles to private businesses, working directly with founders to improve operations, strengthen financial discipline, and support long-term growth. His perspective is shaped by a broad operating background—including blue-collar jobs, service roles, and entrepreneurial experience—which enables him to relate comfortably to both rural and urban business owners.

He holds a B.A. in Government from Harvard College. Jonathan lives in Dallas, where he is active in several charitable organizations. In his spare time, he enjoys exploring new restaurants, traveling, hunting, scuba diving, and playing backgammon.