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From Failure to Success: Lessons from Brian Will's Entrepreneurial Journey

March 22, 20253 min read

In a recent episode of the Hammer and Grind podcast, host Brad welcomed a special guest, Brian Will, a seasoned entrepreneur with a wealth of experience in various industries. Brian's journey is a testament to resilience, adaptability, and the power of learning from failure. Here, we highlight the main points from their conversation and provide actionable steps for aspiring entrepreneurs.

Brian Will's Unconventional Path

Brian Will's story is far from typical. He describes himself as "one of the most unconventionally educated guys in business." His journey began with academic struggles, failing out of high school at 16 and barely graduating with a D+ average. After being kicked out of his house, Brian joined the military, serving four years in the Air Force and another four in the Army.

Post-military life presented its own challenges. Brian struggled to hold a job and faced repeated firings, which led him to start his own business. At 21, he ventured into the landscaping industry, believing that anyone could mow grass and dig holes. Over eight years, he built this business into seven franchise locations. However, this initial success was short-lived, and the business eventually collapsed.

Learning from Failure

Brian's first major business failure was a turning point. He transitioned to the insurance industry, where he built and sold multiple companies to venture capital and private equity firms. His career further expanded into consulting, sales, and management with Fortune 500 companies. Along the way, he authored three books, got involved in politics, and pursued personal interests like becoming a pilot and dive master.

One of the key lessons Brian shares is the importance of managing personal finances. During his early entrepreneurial days, he made the common mistake of increasing his lifestyle expenses in tandem with his rising income, often spending 110% of what he earned. This financial mismanagement contributed to the downfall of his first business.

Action Steps for Aspiring Entrepreneurs

Brian's journey offers valuable insights for anyone looking to succeed in business. Here are three actionable steps based on his experiences:

1. Embrace Failure as a Learning Opportunity

Failure is an inevitable part of the entrepreneurial journey. Instead of fearing it, embrace it as a learning opportunity. Analyze what went wrong, identify the lessons, and apply them to future endeavors. Brian's ability to bounce back from his landscaping business's collapse and find success in other industries is a testament to the power of resilience and adaptability.

2. Manage Your Finances Wisely

One of the critical mistakes Brian made was living beyond his means. As your business grows and your income increases, it's essential to manage your finances prudently. Avoid the temptation to inflate your lifestyle expenses. Instead, focus on saving and reinvesting in your business. Maintaining financial discipline can provide a safety net during tough times and ensure long-term sustainability.

3. Seek Continuous Learning and Growth

Brian's diverse career path highlights the importance of continuous learning and personal growth. Whether it's through formal education, self-study, or hands-on experience, always seek opportunities to expand your knowledge and skills. Diversifying your expertise can open new doors and help you navigate the ever-changing business landscape.

Brian Will's entrepreneurial journey is a powerful reminder that success is not a straight path. It's filled with ups and downs, failures and triumphs. By embracing failure, managing finances wisely, and committing to continuous learning, aspiring entrepreneurs can navigate their own journeys with greater confidence and resilience. Take these lessons to heart and apply them to your own entrepreneurial endeavors.

Resources

Grab Brad's tell-all book: The Contractor Profit Blueprint

https://thecontractorprofitblueprint.com

As a former Marine from Southern Indiana, Brad understands the importance of leadership, grit, and determination. After the Marines, Brad worked various jobs until he founded a successful construction business specializing in high-end Handyman and Residential Remodeling, completing over 2,500 jobs for 900+ customers. 

Now focused on coaching, Brad helps contractors break free from the crazy cycle of struggle, driven by a passion to support those striving to build businesses with integrity, ensuring they don't give up on their dreams. 

He believes everyone has the opportunity to create abundance in their life, business and community, but oftentimes they fall short due to a lack of knowledge. His mission is to grow people, create community and live abundantly.

Brad Huebner

As a former Marine from Southern Indiana, Brad understands the importance of leadership, grit, and determination. After the Marines, Brad worked various jobs until he founded a successful construction business specializing in high-end Handyman and Residential Remodeling, completing over 2,500 jobs for 900+ customers. Now focused on coaching, Brad helps contractors break free from the crazy cycle of struggle, driven by a passion to support those striving to build businesses with integrity, ensuring they don't give up on their dreams. He believes everyone has the opportunity to create abundance in their life, business and community, but oftentimes they fall short due to a lack of knowledge. His mission is to grow people, create community and live abundantly.

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