Most entrepreneurs are secretly scared of the risks involved in buying a business—even when it could transform their lives. In this eye-opening episode, Elliott Holland, a seasoned deal-maker with over 15 years of experience in private equity and business acquisition, shares the counterintuitive mindset that separates successful buyers from the rest. Discover why the biggest hurdle is often your own mindset—and how embracing risk, scrappiness, and imperfect progress can lead to extraordinary rewards. Elliott reveals the real story behind his first deal, the lessons learned from a messy SBA transaction, and why luck still plays a starring role in business success. You'll uncover concrete strategies like leveraging SBA loans, thinking creatively about deal risks, and how to avoid falling into W2 employee traps that keep most from ever buying their first business. Plus, he breaks down the surprising mindset shift necessary: risking less can sometimes mean winning bigger. You'll learn why most people miss out on lucrative opportunities because they approach business buying like a job—playing by rules that work only in employment, not entrepreneurship. Elliott emphasizes that resilience, curiosity, and a willingness to make imperfect decisions often outperform the smartest tactics. If you’re contemplating your first acquisition or trying to build a life of freedom through business ownership, this episode is your wake-up call. Perfect for aspiring buyers, seasoned entrepreneurs, or anyone tired of the status quo—this episode inspires practical action and mindset adjustments that can make the difference between staying stuck and winning big. Dive in to understand how to operate in the gray, embrace the messiness of deals, and truly leverage the power of risk, effort, and excellence.

Guest Credibility:

Elliott Holland is an expert in small and mid-sized business acquisitions and private equity, known for helping first-time buyers avoid costly mistakes and execute deals with confidence. His experience spans private equity, independent sponsorship, and self-funded search strategies, making him a trusted voice in the entrepreneurial acquisition space.

Elliott Holland LinkedIn: https://www.linkedin.com/in/elliottholland/

Hire Elliott Team at Guardian Due Diligence: https://www.guardianduediligence.com/

Why do we rush to set new goals without first reflecting on what God has already done?

In this episode of Think On These Things, we discuss the importance of starting the year with gratitude and praise, rooted in Philippians 4:8. Instead of focusing only on what went wrong or what still needs to happen, we reflect on God’s faithfulness through both the good and the difficult moments.

From personal growth and patience to marriage, expectations, and learning to trust God’s timing, this conversation highlights why remembrance and gratitude are essential for spiritual and emotional growth.

If you’ve ever felt discouraged because your goals didn’t fully come to pass, this episode offers encouragement, perspective, and hope for the year ahead.

Most agency owners don’t fail because they aren’t working hard.
They fail because they’re building the wrong things at the wrong time.

In this episode, we sit down with Jesse P. Gilmore, founder of Niche Control and creator of the Leverage of Growth Framework, to unpack why so many agency owners get stuck — and how to break through without burning out.

Jesse has coached 500+ agency owners, and in this conversation he shares real, practical insights on:

• Why hustle culture eventually breaks agencies
• The first systems founders must build to scale
• How thinking must change at each revenue stage ($0 → $1M+)
• Why sales clarity beats marketing in the early stages
• When (and who) to hire as your first key team members
• How to build an agency that doesn’t depend entirely on you

This episode is especially valuable for agency owners, consultants, freelancers, and service-based entrepreneurs who feel stuck, overwhelmed, or unsure what to focus on next.

If you want better systems, clearer offers, stronger leverage, and less chaos, this conversation will give you direction you can actually apply.

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