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As your executive copilot, our mission is simple: we help incredibly successful people and firms become their absolute best.  As individuals.  As leaders.  As teams.  As organizations.

Image: Tech. Sgt. Hans Deffner.  F-15E Eagle refueling over Saudi Arabia during Operation Desert Shield.


Choate is a boutique executive coaching firm specializing in the financial services, real estate, and investing industries.  We work exclusively with exceptionally accomplished professionals and teams to provide a confidential sounding board and thought partner, utilizing objective assessment and feedback. 


In a competitive world, it is inherently challenging, complex and lonely at the top.  It is challenging, complex and lonely getting to the top.  Leading is difficult.  Navigating interpersonal and group dynamics is complicated.  Winning, however defined, is arduous.  At Choate, we walk side-by-side with our clients as they face complex challenges every day.  With a proven, highly-rated track record, we bring decades of experience to every engagement across the venture capital, private equity, real estate, investment management and investment banking landscape.


Image: Emily Harrington in Peru. Taken by Matty Hong.

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Choate was founded by Jonathan Shepherd and the firm’s roots trace back to the Harvard Business School MBA coaching program.  In 2007, following over a decade of finance and investing success, Jonathan joined the HBS Career & Professional Development office where he had oversight of the finance, investing & real estate industries.  In this particularly unique role, Jonathan spent the next fifteen years coaching several thousand HBS alumni and students, leading group programs, and building hundreds of recruiting relationships with the top venture capital, private equity, investment management, investment banking and real estate firms in the world.  Through every one of his interactions, Jonathan developed a broad and deep repertoire of coaching and industry knowledge.

Jonathan began his career in investment banking at JPMorgan Chase before moving to investment management at Morgan Stanley.  Immediately prior to joining HBS, he was the CFO of TCP Communications, a private equity-backed wireless tower company that was sold to Global Tower Partners, a Blackstone Group portfolio company.  Since 2007, Jonathan has learned and benefitted from HBS’s wide array of specialized coaches, who convene regularly to share best coaching practices.  Additionally, he is an ACTP Certified Executive Coach and ACSTH Certified Career Coach.  He is ICF certified, Hogan certified and MBTI certified.  When appropriate, Jonathan utilizes his strong network of elite coaching professionals to meet clients’ needs.

Jonathan received his MBA from Columbia Business School and BA in Economics from Middlebury College.  He resides in Boston with his wife and daughters.  When he is not cheering on his girls, you are likely to find him skiing, golfing or enjoying the Maine coast.


We leverage the expertise and competence gained through thousands of coaching sessions with extraordinary professionals facing real-time situations and obstacles.  We have partnered with individuals who are currently or formerly working at hundreds of preeminent firms, including:



On May 23, 2021, Phil Mickelson won the PGA Golf Championship, the 6th major championship of his career and his 55th professional win.  At the time, he was the oldest person to ever win a major championship.  In his Wanamaker Trophy acceptance speech, Mickelson began by thanking his wife and brother, Tim.  The third person Mickelson thanked was his coach, “Andrew Getson, who has taken me from not swinging well to swinging pretty, pretty good, and [I] just really appreciate all of the hard work that he has put in to helping me achieve this.”


Think about that: Phil Mickelson is one of the best golfers to ever walk the planet.  He knows the mechanics and feel of the golf swing as well as anyone.  Yet at nearly 51 years old, the person that he thanked immediately after his wife and brother was his coach, “for helping me achieve this.”


At Choate, we have a history of helping some of the absolute best maximize their performance.  What potential victories are you or your firm losing?  Let’s talk, without any commitment or cost, to explore if Choate is the right fit for you and your organization.  Jonathan Shepherd can easily be reached at 917-673-4213 or

Image: Geoff Burke-USA TODAY Sports

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