Navigating the Emotional Rollercoaster of Entrepreneurship with Brian Smith

In this episode of the Traversing Entrepreneurship podcast, host Derek Dall'Olmo sits down with Brian Smith, an entrepreneur who’s seen it all—from humble beginnings washing boats and launching a college photography business to navigating the highs and lows of real estate. Brian’s story is one of grit, growth, and ultimately, reinvention.

Burnout pushed Brian to make a life-altering decision: selling his businesses and stepping back to reassess his purpose. That pivotal moment led him to coaching and founding the Founders Organization, where he now helps fellow entrepreneurs thrive.

Brian opens up about the emotional challenges of building a business and how critical decision-making is to long-term success. He dives into the culture shocks of moving to Mexico, the realities of starting a new agency during COVID-19, and how identifying market gaps can lead to unexpected opportunities.

Throughout the episode, Brian shares insights on building a resilient mindset, fostering a strong company culture, and why consistency is non-negotiable in the pursuit of business growth. If you’re an entrepreneur looking to learn from someone who’s been in the trenches, this episode is packed with practical wisdom and relatable stories.


In This Episode:

Entrepreneurial Journey: Brian's early ventures included washing boats, starting a photography business, and later transitioning into real estate, leading to significant growth and community involvement.

Overcoming Burnout: Burnout led Brian to reassess his life and ultimately pivot into coaching and supporting other entrepreneurs.

Resilience and Decision-Making: Entrepreneurship requires emotional resilience, decisive action, and the ability to adapt to changing circumstances.

Team Building and Scaling: Successful business growth involves building a strong team, leveraging expertise, and fostering a positive company culture.

Adapting to Change: COVID-19 prompted Brian to start a new agency, highlighting the importance of adaptability and seizing new opportunities.

Mindset and Sales Discipline: Maintaining a resilient mindset and treating sales as a daily non-negotiable are crucial for sustained success.

Connect with Brian:

Email: [e-mail]

Website: http://strategyladders.com/

About TreMonte and Traversing Entrepreneurship Podcast

Traversing Entrepreneurship is a show for and about business owners in Traverse City, Michigan and beyond. In each episode, host Derek Dall’Olmo sits down with local business owners and the professionals who serve them to talk about business building, life, money, taxes, family — and all the ups and downs that come with doing something different. Join us to hear their stories and lessons learned — and to get inspired about what might be possible in your own business.

Derek is the founder of TreMonte Financial Consultants, LLC and TreMonte TreMonte Tax Solutions, LLC (together referred to as “TreMonte”). TreMonte works with business owners and entrepreneurs to develop a proactive tax strategy that maximizes after-tax profits. It is TreMonte’s goal to bridge the gap between Financial Advisors and Accountants by serving as CFO to their clients.

This show is for informational purposes only and should not be viewed as personalized financial, investment, tax, or legal advice. You should always consult an attorney or tax professional regarding your specific legal or tax situation.

Please email Derek Dall’Olmo at [e-mail] with questions and comments or to schedule a one-on-one conversation.

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