Real business coaching so you can
dream with courage, grow with confidence, and shine with clarity.

See How

The courage to break free.

Let’s face your fears, the unknown, the crammed calendar. No more draining your energy. Instead, let’s roll up our sleeves and build something sustainable and incredible.

The confidence to grow—wisely.

Together we’ll:


who you are, and what you’re the best at.


how to inspire your team to be cohesive, curious, and excited.


big to get where you really want to be.


a clear roadmap so you can step on the gas and go.


with measurable goals and learn how to count your success.

Clarity for others…

“After a work session with Keith, I leave so much smarter, and clear about where I want my business to go and what steps I need to take to get there. I feel comfortable bringing him the big scary problems that keep me up and night, and through his calm nature, large toolbox of resources and thoughtful approach he helps me discover a path forward. I can’t say enough about what Keith has done to help me bring my dream business to life!”

Mary CecchiniFounder, Living Big

“Keith has helped us make incredibly tangible progress as a company. We've gone from reluctance, to mild hesitancy, to eagerness, to a kind of passionate commitment to the work we are doing with the Keith Upkes Coaching. Our firm has made enormous, positive changes as a result. None of them was easy, as change never is. But they are critical things that wouldn’t have happened without the strategic vision and guidance Keith has provided.”

Zach HyderPartner, Quinn Thomas

“Keith recently took our leadership team through a customized planning workshop. We left the workshop all in alignment with our One Page Strategic Plan complete! Because the workshop was custom for our company, we got so much out of it! ”

Brandy CallahanArea Floors

“Keith has helped our company face the challenges inherent in such significant growth by coaching us through tough decisions, keeping us accountable and focused, and helping us implement the necessary changes to transform from a small entrepreneurial company to a leader in our market that is stronger and more focused. Having Keith as a coach and mentor has enabled me to experience more personal happiness.”

Kevin LewandowskiFounder, President & CEO of Discogs

“Keith has been a wonderful addition to our team. With his guidance, perspective and encouragement we are in a much better position as a company than we otherwise would have been. ”

Lance KillianKillian Pacific

“Bringing Keith on was a turning point in our business! Ever since we incorporated Keith and the Rockefeller habits, we consistently post 30%+ growth of top line revenue and profitability year over year. It’s no coincidence! Keith has challenged us to deal with the challenges that come with such significant growth by coaching us through those decisions. We have moved from a small entrepreneurial company to a leader in our market. ”

Travis DillardInflow Communications

“In 2015, when my company was going through the culture issues that come with fast growth, I felt like I was at a loss. I hired Keith to help me align my team and move past the issues at hand. With Keith, I got a partner dedicated to my individual success as a CEO, the success of my executive staff, the success of each employee, and the overall success of my company. Keith pushes us all to become better people. My company has grown by leaps and bounds and it's thanks to the tools that Keith has provided and continues to provide us each time he works with us! ”

Amy BallietKiller Infographics

Meet Keith.

I believe in different paths to success. In my 30 years of business management, I’ve coached many clients toward their dreams—whether that’s more profitability, more free time, or a more mindful growth plan. We always get from Point A to Point B. But how we get there is always different.

I personally know what it’s like to break free from fear. To have time to do your best work. Live your best life. It’s amazing how your attitude toward your work, your family—everything—changes. Knowing that, I can’t stop sharing what I know. It’s just what I do.

I’m genuinely passionate about getting to know my clients, and helping them discover their unique path towards success and the freedom to live well.

Tips from Keith

May 14, 2018

Is your strategy a “Wild Ass Guess”?

Start with a dream Strategy starts with a dream that becomes a 10-30 year goal.  Why do so many companies not achieve their dream?  It is because most companies are…

Execution Exercise Execution
May 10, 2018

3 execution steps to quickly solve any challenge

Working with a recent client we uncovered that revenue had rapidly started to fall off.  They realized that they would quickly have a cash flow challenge if they didn’t solve…

September 29, 2017

Laws of Leadership: Make Yourself Replaceable

As a leader or entrepreneur, you’ve probably heard some of these phrases before: “Train your replacement.” “Name your number 2.” “Who’s in charge if you get hit by a bus?”…

Let’s Connect

I’m excited to meet you.

Tell me about yourself. Then together we can figure out where you want to go.

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