Dan Sherwood

Sales Manager, Coach

Leadership, Sales, Mindset, 1:1 Impact Coach

Career Experience – In 2005 Dan launched a painting company serving the historic towns along the Atlantic coast north of Boston. He had zero professional experience in the trades and even less practical experience. 

Dropping $20k on direct mail, Dan sold work before he even had a crew to produce it. Applying the sales and marketing skills gained during his career in the action-sports industry, Dan quickly established himself in the market and built a seven figure business.

Dan joined The Contractor Fight in 2020 and became full-time in 2022.

The paint business continues, providing him endless perspective on the real world experiences of contractor life.

“Who dares wins.”

His Struggles – Professionally, Dan’s lack of direct trade knowledge required him to adapt his other skills in order to succeed. Once he saw this fact as an advantage rather than a liability the business began to thrive. Instead of relying on technical knowledge, he focused on the customer experience and building a unique brand in the market.

Personally, his biggest obstacle was believing that he was worthy of reaching his potential. Having been the middle of three brothers, two of which were quite ill most of their lives, Dan struggled with survivor’s guilt for years. This left him feeling greedy about utilizing simple blessings like his health, athleticism, business, family, and success. He never felt worthy to pursue his potential.

Thankfully through extensive personal development (Dan never stops working on himself), he was able to unfuck his mind and utilize his experiences for the benefit of others.

What Qualifies Dan to be a Coach? – Dan’s superpower is that he’s relatable and authentic. 

Seven years of being coached by Tom, in both individual and group programs, provided an understanding of both sides of the coaching conversation. He innately understands the mindset and plight of TCF clients and finds purpose guiding others down the trail he’s broken himself.

His TCF podcast, Friday Fails, delivers advice based on decades of experiences, both good and bad. 

Through interactions with thousands of contractors, in addition to personal experiences within and outside the construction industry, Dan offers a unique perspective. This allows those he coaches to identify and reframe their issues to overcome the obstacles in the way.