Who we are


Our mission is simple: protect you and your clients.

Pinnacle Risk Strategies, PLLC, is a specialized law firm that helps those who work in the outdoors manage risk to maximize reward. With over 40 years of combined experience in the outdoor industry, we know where you’re coming from. Our directors have unique backgrounds as practicing attorneys with deep roots in outdoor logistics, medical response, operations, and risk management. 

Through comprehensive, 21st-century legal and consulting services tailored to address the industry’s needs, we are here to help you create and maintain a strong, dynamic, protected organization.


Chad Olcott


Chad brings fifteen years of legal and outdoor-oriented business experience and risk management to Pinnacle Risk Strategies. A practicing attorney and director at a thriving outdoor adventure company, Chad is a graduate of Bowdoin College and the University of Maine School of Law. During and after college, he led small-group hiking, backpacking, and mountain-biking trips in New England and the American West before working in adventure programming and logistics.

Following law school, Chad served as a litigator and command advisor in San Diego and Sardinia, Italy while serving in the US Navy. After leaving the Navy, Chad practiced corporate law with a midsize firm in Portland, Maine, before joining Apogee Adventures, a youth-oriented outdoor adventure and experiential education company, as a full-time company director in 2009. Since joining Apogee, Chad has served as the company’s in-house general counsel, guided Apogee through the accreditation process, and developed a comprehensive risk-management program.

Chad lives in Brunswick, Maine, with his wife, Susan, and their twin daughters.


  • Bowdoin College, A.B., Philosophy, cum laude

  • University of Maine School of Law, J.D., cum laude


  • Maine


Ben Tettlebaum


Ben grew up on a farm in Missouri and has loved the outdoors ever since. He has been involved with the outdoor industry for over 20 years. In addition to owning his own adventure travel company, Ben has worked for some of the most prominent organizations in the industry, including NOLS and NOLS Wilderness Medicine, Appalachian Mountain Club, Student Conservation Association, REI, and Second Nature.

A lifelong pragmatic idealist, Ben left full-time teaching and administering outdoor programs to broaden his impact on conserving the natural world through the practice of environmental law. After clerking for the Hon. Judge Duane Benton in the U.S. Court of Appeals for the Eighth Circuit, Ben became a Rhodes Fellow, helping create a sustainable agriculture program for Conservation Law Foundation (CLF) in Maine. He advocated for resilient agricultural policy, lobbying at the local, state, and federal levels. Ben remained with CLF, launching a statewide legal services organization for startup and established food and agriculture businesses. He also worked extensively in CLF’s Clean Energy and Climate Change Program, overseeing cases involving electric utilities, natural gas companies, and the clean energy sector.

With Pinnacle Risk Strategies, Ben combines his passion for connecting people with the outdoors and grappling with complex legal issues to help outdoor organizations achieve a new and higher standard of excellence.


  • Bowdoin College, A.B., Philosophy

  • Cornell Law School, J.D. cum laude

  • NOLS Wilderness Medicine, WEMT


  • Maine

  • Missouri