Today’s guest is Matthew Fenton, who lives in Oregon wine country with his wife and two cats. Matthew is the founder of Three Deuce Branding, a one-man consultancy with a simple mission: “to help good people build great brands.” Since 1997, he has helped hundreds of clients — including Fidelity Investments, Wrigley and Valvoline — to achieve what he calls “brand clarity” by better positioning, strategy, and messaging.

Matthew also spent seven years in client-side brand management, including two as a chief marketing officer. During that time, he launched White Mystery Airheads and led Trolli Sour Brite Crawlers to become the best-selling gummy worm in the U.S.

Matthew is also the founder of Winning Solo, a coaching business designed to help other independent consultants and creatives to enjoy longevity, balance and success on their own terms. 

Today’s conversation is divided into two halves: Matthew recently became a fractional chief marketing officer for a longtime client. A “fractional” role has become a buzzword, at least in the U.S. freelancing world, and Matthew is the perfect person to talk about what this means and how we might consider becoming a fractional “whatever” — the role is not limited by industry or service. 

Then, we talk about a conversation that he and I had started offline about the importance of improving both the quality of your work and how you are to work with from the client perspective. 

In this episode, we talk about: 

• How he was failing at the start of his freelance career. 
• How he is focusing on his physical and mental health in the chaos of 2025. 
• How his career took an unexpected pivot recently. 
• What a fractional role is — and what it is not.
• The three qualities you need before you market yourself as a “fractional.”
• How to protect yourself as fractional when it seems you might be putting “all your eggs in one basket.” 
• The benefits of being a fractional.
• How to set boundaries with a fractional client so you are not seen as an employee. 
• The importance of doing outstanding work and improving your craft every single day. 
• Strive to be in the top 5% of your craft.
• The problem with focusing on personal branding first and not your craft. 
• “Talent” is not a good enough reason to rehire someone if they are difficult to work with. 
• The four areas to evaluate so you can improve as a freelancer: core skills, adjunct skills, the work that brings in the work, and character traits. 
• Three ways to ask clients for feedback so you can continue to improve. 
• How time tracking has helped us improve our business — but also our craft. 
• Ways you can begin to improve your craft. 

Resources:

Deliberate Freelancer Facebook group

Support Deliberate Freelancer at Buy Me a Coffee

Book that Matthew mentions: “Playing to Win: How Strategy Really Works” by A. G. Lafley and Roger L. Martin 

Matthew on LinkedIn

Matthew’s consulting website

Winning Solo website