Couverture de Cash Flow, Confidence, and Failing Forward (AUDIO)

Cash Flow, Confidence, and Failing Forward (AUDIO)

Cash Flow, Confidence, and Failing Forward (AUDIO)

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 Welcome to No Sugarcoat'n — where business leaders come for real talk, not rainbows. In this episode, Beth McClary-Wolford sits down with Jessy Cardenas, CEO of Century Roofing, to unpack the leadership misconceptions that only show up once you’re in the seat. Jessy shares how she found herself in roofing, what surprised her most about ownership, and why leading people is far more complex than “just doing it better than your boss.” They talk candidly about cash flow, staff development, long-term thinking, being a woman in a male-dominated industry, and the uncomfortable truth that leadership often means being disliked — not admired. Guest Introduction: Jessy Cardenas is the CEO of Century Roofing, a Chattanooga-based roofing company built on genuine care, accountability, and long-term community commitment. With over a decade in the industry, Jessy brings a rare leadership perspective shaped by operational grit, people development, and the reality of running a construction business as a woman in a traditionally male-dominated field. Her approach blends tough decisions with deep care — and zero sugarcoating. Key Takeaways:
  • Owning a business is significantly harder than it looks from the outside — and perfection isn’t part of the deal.
  • Leadership isn’t about being liked; it’s about making decisions that move the business forward.
  • Pouring into employees matters — but leaders must recognize when people are ready to grow beyond the company.
  • Cash flow isn’t a finance concept — it’s a survival skill.
  • Playing the long game builds trust, reputation, and real community impact.
  • Failure isn’t failure — it’s revision, learning, and momentum if you stay in motion.

Chapter Markers: 0:00 Welcome to No Sugarcoating 0:45 Meet Jessy Cardenas, CEO of Century Roofing 1:30 How Jessy found herself in roofing 3:00 From selling roofing to owning the company 4:15 The biggest surprises of ownership 6:30 Why leadership is harder than expected 8:20 Lessons learned from previous employers 10:00 Investing in people — and when to let them go 12:30 What makes Century Roofing different 14:45 Playing the long game in construction 16:30 Letting go of perfection as a leader 18:15 Advice for new business owners 20:30 Core values and building around your strengths 23:00 Writing a letter to her past self 26:00 Being a woman in the roofing industry 29:00 Rapid-fire leadership truths 36:00 Final reflections and closing thoughts Keywords: No Sugarcoat'n podcast, Beth McClary-Wolford, Jessy Cardenas, Century Roofing, leadership misconceptions, women in construction, small business leadership, cash flow management, people development, business ownership realities, construction leadership, community-based business, failing forward, long-term thinking
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