In this episode of The Thoughtful Entrepreneur, host Josh Elledge speaks with Andrew Poles, Founder and CEO of Andrew Poles Executive Coaching. Andrew is an executive coach who helps startup founders and small business owners build leadership capacity, navigate high-pressure growth, and scale their ventures effectively. With a background in entrepreneurship and a passion for personal development, Andrew brings practical insights to leaders striving to grow not only their companies—but themselves.

Andrew works with two key audiences: high-growth startup founders (particularly in tech and medtech), and small business owners navigating more stable, bootstrapped environments. For tech founders, challenges often revolve around investor pressure, scaling quickly, and transitioning from doing everything themselves to leading others. These leaders must rapidly establish culture, process, and structure in what Andrew calls a “pressure cooker” environment.

Small business owners face a different set of obstacles. Without investor capital, they're often bootstrapping their operations and must maintain long-term stability while building sustainable growth. Andrew supports both types of founders with customized coaching that helps them sharpen leadership skills, foster emotional resilience, and drive strategic clarity—even amid chaos.

He also discusses how systemic disruption—especially through AI—is reshaping how companies build, operate, and scale. While software companies can now move faster with leaner teams thanks to AI, product-focused businesses face greater uncertainty from external factors like tariffs and supply chain instability. Andrew’s coaching helps founders stay grounded and make smart decisions amid uncertainty.

Andrew Poles is the Founder and CEO of Andrew Poles Executive Coaching, where he helps entrepreneurs grow as leaders while scaling successful businesses. With a background in startups and a deep understanding of leadership psychology, Andrew guides founders through personal and organizational transformation.

Andrew Poles Executive Coaching offers 1-on-1 coaching, leadership development, and strategic guidance tailored to entrepreneurs, founders, and executives. Andrew specializes in helping leaders in high-pressure, high-growth environments build the clarity, confidence, and capacity needed to scale both themselves and their companies.

• Andrew Poles Website
• Andrew Poles LinkedIn

• Startups vs. Small Business: The different leadership challenges faced by tech startup founders vs. bootstrapped business owners.
• The AI Shift: How artificial intelligence is changing the way software companies operate and compete.
• Leadership Pressure: Why transitioning from self-management to team leadership is one of the hardest leaps for first-time founders.
• Personal Development: Andrew’s philosophy that a founder’s growth directly shapes the company’s trajectory.
• Holistic Success: The importance of blending business goals with personal growth to create long-term fulfillment and impact.

Josh Elledge’s conversation with Andrew Poles delivers valuable insights for entrepreneurs navigating high-stakes leadership roles. Whether you're building a unicorn startup or growing a steady...