Bill Clawson is a seasoned executive and financial strategist with a strong track record of leadership across multiple industries. He currently serves as CEO of Endeavor Financial Insights LLC, where he guides businesses and individuals in navigating complex financial landscapes with clarity and foresight.
Raised in Missoula, Montana, Clawson’s early achievements foreshadowed his future success. A decorated athlete, he was an All-State high school wrestler and a member of the Amateur Trapshooting Association’s All-American team, earning the prestigious ATA Hall of Fame Scholarship. He graduated as the top male student by GPA from Sentinel High School in 1988.
Clawson continued his education at the University of Montana, where he became President of Sigma Nu Fraternity and graduated with honors in 1993. His academic and leadership experience laid the foundation for a diverse and impactful career.
Professionally, Clawson served as President of Clawson Windows, a company known for its dedication to craftsmanship and innovation. He went on to lead regional industry efforts as President of the Missoula Building Industry Association and later as Chairman of the Timber Products Manufacturers Trust, where he championed sustainable business practices and small business advocacy.
A strong supporter of free market capitalism, accountability, and strategic planning, Clawson is deeply engaged in conversations around accounting, small business growth, and long-term financial health. His philosophy blends practical insights with values-driven leadership.
Outside of work, Clawson is a dedicated supporter of Habitat for Humanity and remains active in his local community. He enjoys Montana Grizzly football and basketball, attending concerts and sporting events, and traveling with his family, who remain central to his life and motivation.
What is your typical day, and how do you make it productive?
My day starts early—usually around 5:30 AM. I like to start with some quiet time and a short walk to clear my head. By 7:00 AM, I’m reviewing client files or preparing for the day’s meetings. I block my mornings for focused work—planning, reviewing numbers, or working on strategic issues. Afternoons are more flexible and usually filled with team check-ins or industry calls. I don’t over-schedule. That’s key. Leaving space in the day allows me to handle issues that come up without derailing everything else.
How do you bring ideas to life?
I test ideas in small, real-world ways. At Clawson Windows, if we had an idea for a new product line or service approach, we’d prototype it with one or two clients before going wide. I still do that. I believe in starting local, gathering feedback, and adjusting fast. Good ideas don’t need a billboard; they need a blueprint and honest input.
What’s one trend that excites you?
The growing interest in trades and vocational education. For years, we pushed every kid toward a four-year degree, but now there’s a shift happening. People are seeing the value of practical skills and essential industries. That excites me. We need builders, welders, and planners just as much as coders.
What is one habit that helps you be productive?
I take notes by hand. It slows me down just enough to think clearly. I keep a simple notebook on my desk for meetings and planning. Later, I scan it and tag it digitally. There’s something about writing that helps me connect with what I’m thinking.
What advice would you give your younger self?
Don’t rush to prove yourself. It’s easy to get caught up in titles or recognition early on. But what lasts is how you treat people and how you carry yourself. If I could go back, I’d remind myself to listen more and talk less—especially in rooms where I felt I had something to prove.
Tell us something you believe almost nobody agrees with you on?
I believe boredom is underrated. Some of my best thinking has come when I’m not stimulated—on a walk, sitting in traffic, or just staring out a window. We’ve trained ourselves to avoid boredom with constant input, but there’s value in letting your brain wander.
What is the one thing you repeatedly do and recommend everyone else do?
I review the week every Friday afternoon. Wins, losses, what didn’t get done, what I’m carrying forward. It’s not a performance review—it’s just a rhythm that helps me stay honest with myself and plan smarter for the week ahead.
When you feel overwhelmed or unfocused, what do you do?
I get outside. That might be a walk along the Clark Fork River or driving outside town for some air. Movement and space help me reset. I’ve learned that sitting longer doesn’t solve mental clutter—stepping away does.
What is one strategy that has helped you grow your business or advance in your career?
Show up to the meetings nobody else wants to attend. Early in my career, I volunteered for committee work or off-hour obligations at the Missoula Building Industry Association. Those spaces—where few were paying attention—built my reputation as someone dependable. Eventually, those small moments led to bigger opportunities.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
In the early 2000s, I expanded Clawson Windows too quickly into a market without testing it first. We assumed our systems would scale, but they didn’t. It strained cash flow and operations. I pulled back, restructured, and doubled down on core regions. The lesson: grow with control, not just ambition.
What is one business idea you’re willing to give away to our readers?
A mobile mentoring platform that connects retirees from trade industries with young people entering those fields. Many skilled tradespeople have deep knowledge and want to give back. A system for paid or volunteer micro-sessions could pass along insight that’s currently being lost.
What is one piece of software that helps you be productive? How do you use it?
I use Trello to manage personal and professional tasks. It’s visual, flexible, and easy to maintain across projects. I keep one board for Endeavor, one for family goals, and one just for reading and learning.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
The Boys in the Boat by Daniel James Brown. It’s about the 1936 U.S. Olympic rowing team. I love the themes of grit, timing, and unity. It reminds me that success comes from teams that row together, not stars who go it alone.
What’s a movie or series you recently enjoyed and why?
Longmire. It’s grounded, has strong characters, and takes its time. I like stories that aren’t in a rush to impress—just like leadership.
Key learnings
- Small actions build lasting results. Productivity often comes from low-tech habits like handwritten notes and weekly reviews.
- Real-world leadership starts early. Showing up for less glamorous roles can create long-term credibility and opportunities.
- Mistakes are valuable teachers. Scaling too fast without testing led to one of Clawson’s biggest lessons: growth must be earned, not assumed.
- Discipline is transferable. Lessons from sport, like consistency and focus, shape behaviour and decision-making well beyond the mat.
- Planning isn’t paperwork—it’s peace of mind. Reviewing your week and tracking your ideas builds clarity and momentum over time.