Jan. 13, 2026

Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System

Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System
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In this episode of Sales & Cigars, Walter sits down with Alan Ward, CEO of Securely.io, for a thoughtful conversation that spans entrepreneurship, sales, leadership, and the realities of disrupting long-entrenched systems.

Alan shares how his worldview shapes the way he leads and sells, why transparency is missing in traditional payment systems, and what it takes to introduce truly revolutionary ideas into the market. From cutting a house in half at 19 years old to building a fintech platform designed to serve businesses—not extract from them—this episode is about values, conviction, and selling change the right way.

In This Episode:

  • Why Who Not How shaped Alan’s approach to leadership and business

  • The Golden Rule as a foundation for sales, culture, and decision-making

  • How worldview influences leadership and organizational behavior

  • Alan’s entrepreneurial origin story and early risk-taking

  • Why businesses don’t truly understand their payment costs

  • What “open banking” means—and why it’s a game changer

  • Evolutionary vs. revolutionary change in technology and sales

  • Why education—not pitching—is required to sell disruptive ideas

  • Selling vision to customers, teams, investors, and boards

  • The role of trust, transparency, and alignment in long-term success

  • Celebratory cigars and the moments that make business memorable

Key Takeaways: 

  • Sales is often about helping people see what they couldn’t see before

  • Transparency builds trust—hidden systems create resistance

  • Entrepreneurs are always selling, even when they don’t realize it

  • Revolutionary ideas feel risky until they become obvious

  • Values-driven leadership scales better than tactics alone

Connect with Alan:

Connect with Walter Crosby and Sales & Cigars:

Website: Helix Sales Development

LinkedIn: Walter Crosby

Instagram: @wcrosby248

Facebook: Helix Sales Development

 

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Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.