
What Is Winning Solo?
It takes courage to bet on yourself. But being an expert in your field is only one part of the equation. Success means mastering a whole new set of skills.
I’m not going to pretend that it’s easy. The average freelancer in the US makes less than $60,000 a year, and the path is filled with challenges.
In the words of some independents I’ve surveyed:
- “The new-business wheel is slow to spin but very quick to stop.”
- “It’s tough to balance prospecting and delivering.”
- “Cash flow is a rollercoaster, usually not a fun one.”
- “My self-doubt ties me up in knots, especially during the slow times.”
And perhaps the most troubling words…
“Running the business will run your life if you let it.”
Does any of that sound familiar? I’ve wrestled with it all in my 20+ years of independent consulting. And I’ve realized there’s a better way.
Start With Different Questions
Freelancing, self-employment, knowledge working, soloism – whatever you call it, it’s best viewed as an exercise in lifestyle design. It’s your chance to build the life of your dreams.
One of my core beliefs is that there’s no such thing as “work-life balance.” There is only life balance, and work is one part of life. So we must design our work to fit into our larger goals.
So while Winning Solo will necessarily address topics like “writing effective proposals” and “how to sell without being a sleazebag,” we’ll also go much further.
Winning Solo is for you if:
- You value your independence, and you intend to keep it.
- You want the freedom to pick your clients and projects, and to do meaningful work on your terms.
- You value control – of your calendar, your income and your physical and mental health.
- You’re good at the work you do, but struggle with some of the other aspects of flying solo.
- You’re willing to put in the work.
If that sounds like you, I hope you’ll subscribe to my twice-monthly newsletter, check out my coaching services, or just reach out to say hello.

Customized Coaching
Whether it’s positioning yourself, pricing your projects, defining your offer, reclaiming your life balance – you name it, I’ve probably found an answer to it in the 20+ years I’ve been flying solo.
Click below to learn more about our coaching & advisory services.
I may be an expert in marketing and brand strategy, but when I decided to go out on my own, I quickly realized I didn’t know anything about being a consultant or running my own business.
Matthew was fantastic in sharing best practices and providing his perspective to guide me through this roller coaster of a journey.
Jeni Golomb, Founder & CEO, Bamboo Branding

Hey, I’m Matthew. Welcome!
At age 27, I started my one-man strategy consultancy, Three Deuce Branding. I still run it today, over 20 years later. During that time, I’ve reached some very high highs, made plenty of mistakes, and survived at least three economic downturns.
I’m not going claim that I have some “secret” that will triple your revenue by Tuesday or give you a 10-minute workday. Leave that nonsense to the scammers in your spam folder.
On the contrary, I’m a Midwestern guy who has earned 94% of my consulting revenue via repeat & referral, working with brands you’ve actually heard of, for over two decades.
Self-determination has created all the good things in my life. My mission with Winning Solo is to share what I’ve learned with you – the good, the bad and the counter-intuitive – so that you may enjoy the freedom and balance you deserve.
I hope you’ll join me.
When I went out on my own as a freelance consultant, my first call was to Matthew, who helped me determine my services’ value and position my offering for long-term success.
Years later, that conversation continues to play a critical role in who I am, what I do, who I do it for, and how much I earn.
Tina Kunkel, Principal Consultant, Tina Kunkel Consulting