#511 - Bill Squires - What Challenges Do Business Owners Face?
Fri Feb 06 2026
Business Owners have plenty of challenges. We thought it would be helpful to invite Bill Squires to share his knowledge of those challenges, and more importantly, what to do about them in the next 100 days. Bill has a keen eye for commerce and finances. He wants to help individuals, teams, and businesses achieve their full potential. He has coached business owners (all with challenges), executives, and teams in all aspects of building rapid growth and profitable companies.
Summary of PodcastBill Squires' background and coaching approachBill Squires discussed his background, including his experience in the oil industry, getting an MBA, and then transitioning into business coaching about 8 years ago. He emphasized the importance of helping clients develop a clear vision and plan for their business, rather than just jumping into execution. Bill shared his 90-day planning process and the value of accountability in driving results.
Challenges facing business ownersBill outlined some of the key challenges he sees business owners facing, including finding enough leads and customers, hiring and retaining good people, and getting their team to be more accountable. He noted that many business owners are working long hours but not seeing the financial rewards they expect.
The role of planning and goal-settingThe discussion explored the value of long-term planning, with Bill advocating for 5-year plans that get broken down into 90-day and weekly goals. Kevin challenged whether 5 years is too long to plan for, but Bill shared examples of clients who have achieved their ambitious 5-year goals by sticking to the plan.
The evolution of coaching with technologyGraham and Bill discussed the potential for AI-powered coaching tools that could scale Bill's expertise, while noting the continued value of in-person coaching and the importance of accountability that a human coach provides. They explored how technology and human coaching could complement each other going forward.
Bill's coaching offerings and exit strategyBill outlined his various coaching programs, including one-on-one, group, and community-based offerings. He also shared his plan to eventually step back from the business by bringing on additional coaches and a business development manager to sustain the community he has built.
The Next 100 Days Podcast Co-HostsGraham ArrowsmithGraham founded Finely Fettled eleven years ago to help businesses market to affluent and high-net-worth customers. He's the founder of MicroYES, a Partner of MeclabsAI, providing AI Agents, Workflows and phone-to-agent delivery systems. Now, Graham offers Answer Engine Optimisation so you get found by LLM search and Enterprise-level AI Solutions.
Kevin ApplebyKevin specialises in finance transformation and implementing business change. He's the COO of GrowCFO, which provides both community and CPD-accredited training designed to grow the next generation of finance leaders. You can find Kevin on LinkedIn and at kevinappleby.com
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Business Owners have plenty of challenges. We thought it would be helpful to invite Bill Squires to share his knowledge of those challenges, and more importantly, what to do about them in the next 100 days. Bill has a keen eye for commerce and finances. He wants to help individuals, teams, and businesses achieve their full potential. He has coached business owners (all with challenges), executives, and teams in all aspects of building rapid growth and profitable companies. Summary of PodcastBill Squires' background and coaching approachBill Squires discussed his background, including his experience in the oil industry, getting an MBA, and then transitioning into business coaching about 8 years ago. He emphasized the importance of helping clients develop a clear vision and plan for their business, rather than just jumping into execution. Bill shared his 90-day planning process and the value of accountability in driving results. Challenges facing business ownersBill outlined some of the key challenges he sees business owners facing, including finding enough leads and customers, hiring and retaining good people, and getting their team to be more accountable. He noted that many business owners are working long hours but not seeing the financial rewards they expect. The role of planning and goal-settingThe discussion explored the value of long-term planning, with Bill advocating for 5-year plans that get broken down into 90-day and weekly goals. Kevin challenged whether 5 years is too long to plan for, but Bill shared examples of clients who have achieved their ambitious 5-year goals by sticking to the plan. The evolution of coaching with technologyGraham and Bill discussed the potential for AI-powered coaching tools that could scale Bill's expertise, while noting the continued value of in-person coaching and the importance of accountability that a human coach provides. They explored how technology and human coaching could complement each other going forward. Bill's coaching offerings and exit strategyBill outlined his various coaching programs, including one-on-one, group, and community-based offerings. He also shared his plan to eventually step back from the business by bringing on additional coaches and a business development manager to sustain the community he has built. The Next 100 Days Podcast Co-HostsGraham ArrowsmithGraham founded Finely Fettled eleven years ago to help businesses market to affluent and high-net-worth customers. He's the founder of MicroYES, a Partner of MeclabsAI, providing AI Agents, Workflows and phone-to-agent delivery systems. Now, Graham offers Answer Engine Optimisation so you get found by LLM search and Enterprise-level AI Solutions. Kevin ApplebyKevin specialises in finance transformation and implementing business change. He's the COO of GrowCFO, which provides both community and CPD-accredited training designed to grow the next generation of finance leaders. You can find Kevin on LinkedIn and at kevinappleby.com