About Cultivate

Meet Nate Wolfson, Founder of Cultivate

Nate Wolfson  Founder, Cultivate

Nate Wolfson
Founder, Cultivate

What our clients say


“Our best decision in the last 7 years was starting our business. Second best was hiring Nate. “ 

-Matt Naimoli,
President & Co-Founder
G&N Insurance

Certified EOS® Implementer & Successful Entrepreneur

A lifelong entrepreneur who has built two successful companies, Nate Wolfson has stood in your shoes. He knows what it’s like to work 80-hour weeks, feel incredibly stressed and excited at the same time, and how lonely it can be at the top. 

Nate first discovered EOS when he implemented it in his own business. Everything he teaches comes with his experience and war stories from his own successes and failures.

As one of 200 carefully selected, continually trained Professional EOS Implementers around the world—and the longest-tenured EOS Implementer in New England—Nate is part of an extraordinary community of business experts who are completely committed to helping business leaders get more of what they want from their businesses. Nate’s demonstrated mastery of EOS has earned him the highest level of certification from EOS Worldwide.

A Powerful Change Agent

Gaining traction requires change, and that’s not in everyone’s comfort zone. Nate is courageously confident in asking tough questions that cut to the heart of the issue. Those questions help leadership teams open up and have meaningful conversations, enabling them to create solutions together. Nate leads teams to this alignment based upon his deep belief that “empowerment and accountability are two sides of the same coin."

Your Trusted Confidante

As a Certified EOS Implementer, Nate has fused his passion for building great companies, his deep desire to help others grow, and his strong experience with EOS into a single, incredibly meaningful career. His intentional and lively style, his tactfully candid approach, and his reliable expertise will win your trust.

Start seeing your business in a whole new light.


2000-07:  Nate starts and grows IT services firm Thrive Networks to $10M in revenue before selling the company to Staples.

2008-15: Nate buys into the web development firm Digital Bungalow and restores stability and profitability in two years. He implements a strategic growth plan—leveraging EOS—to grow Digital Bungalow into one of Inc. Magazine’s 5000 Fastest Growing Companies in America for 2012, 2013, and 2014, before selling the company in 2015. During this time, he starts mentoring and coaching other business owners.

2015-present: Nate becomes a full-time, Certified EOS Implementer dedicated to helping entrepreneurs and their leadership teams achieve amazing results. He helps more than 60 companies achieve their potential. 

2019-: Nate begins training new EOS Implementers as co-leader of one of our two quarterly Boot Camps.