Confessions of an Implementer

S2E20: Systems Create Freedom: EOS and the Art of Letting Go with Dave Borland

Host: Ryan Hogan
Guest: Dave Borland (Certified EOS Implementer)
Date: October 29, 2025

Episode Overview

This episode dives deep into the personal and entrepreneurial journey of Dave Borland—a multi-time founder turned EOS Implementer. Host Ryan Hogan and Dave explore themes of entrepreneurial growth, the transformative power of business operating systems like EOS, and hard-won lessons about leadership, hiring, and truly “letting go” to achieve both business and personal freedom.

Key Discussion Points and Insights

1. Early Entrepreneurship and Learning Through Experience

• Dave’s Background:

  • Started in software training in the 1990s, moving into web and database development as technology shifted.
  • Initial ventures: self-taught, highly entrepreneurial, driven by the example set by his entrepreneur father.
  • Early businesses started almost accidentally, often due to necessity (“The dude left town without, you know, he's like, you want to buy it? And he didn't even wait for my answer. He just took off.” – Dave, 05:10).

• Influence of Family:

  • Dave’s father emphasized sales as the foundation of business.
    • “Sales is the first thing he said. Sales is number one. The product is secondary.” (09:17)
  • Entrepreneurship for Dave was about seeking freedom, despite the struggles and risks.

2. Sales Mindset Evolution

• Early Mindset:

  • At first, Dave was focused on selling whatever product was in front of him, not customer needs.
  • “When I first started selling, it was, I can sell it, and it wasn't thinking about you, the buyer, as much. And I think it translates to what I do now...” (00:00, reiterated at 14:41)

• The Big Shift:

  • The breakthrough came with learning curiosity-based sales—asking questions to uncover real needs.
  • Adoption of Sandler Sales concepts: “There's a method but really it's a bunch of questions. It's all questions... questioning works but not questions to force...” (18:08)
  • Realization: Relationships are more important than “just” closing deals.
  • Advice evolved for younger entrepreneurs, focusing on help-first mentality rather than pure numbers game.

3. Challenges of Scaling and Leadership

• Moving from Founder to Leader:
  • The transition from sales-focused entrepreneur to leader “with mouths to feed” was a huge turning point.
  • Early mistakes included hiring based on gut feeling and optimism—often resulting in mismatched hires.
    • “My gut was optimism gut... ultimately three out of four would come in and they would be poor hires. Not because of them, because of me.” (29:15)
• Team Intervention:
  • At one stage, Dave’s team staged an intervention to get him out of direct hiring and operations, focusing instead on his strengths—leadership and vision.
    • “The team sat me down. They had an intervention once. The team that was kind of good. They're like, get out. Right?... you can sell, you can lead... that's it, you get out.” (30:49)
• Letting Go:
  • He learned the hard way about the need to delegate, trust others, and put the right people in the right seats—core EOS concepts.

4. The Pain and Process of Hiring

• Hiring Mistakes:

  • Both Dave and Ryan share stories of hiring blunders, often due to founder bias and making emotional, not process-driven, decisions.
    • Memorable metaphor: “You don't know which way their toilet paper rolls or they have a preference until you move in with them.” (34:15)

• Improved Processes:

  • Both discuss evolution towards structured, team-based hiring processes (e.g., panel interviews, peer feedback).
  • Ryan summarizes hard-won wisdom: “It's always been because of people. Like, we have succeeded or we have failed based upon the people.” (39:22)
  • Critical realization: Founding entrepreneurs must “get out of the way,” or the company will stagnate at the “lava lid”—a ceiling created when everything runs through the founder.

5. The EOS Discovery and Transformation

• Discovery of EOS:

  • Dave’s business hit a wall after merging with another firm. They tried “Scaling Up” (Rockefeller Habits) but lacked execution and structure.
  • EOS was introduced, initially with skepticism, but quickly proved transformative.
  • “Six months into that thing and we... we're making tons of money again. We had the right people in the right seats. I become like, this is that epiphany of like, why am I an EOS implementer? Because it worked for me.” (41:42)

• What Changed with EOS:

  • First step: Building an Accountability Chart to clarify structure and roles (“what structure do you need, not just who do you have?”).
  • Data-driven management, focusing on clear metrics (e.g., billable efficiency) and facing the need to make tough cuts for the health of the business.
  • Implemented core EOS tools (Accountability Chart, Core Values, People Analyzer, Data, IDS/level 10 meetings), prioritizing execution and healthy team dynamics.

  “The structure you have may not be the structure you need and the people in that structure might not be the right people, period.” – Dave (49:37)

  • The result: not just profitability, but a renewed sense of joy and direction as a leader.
  • Dave’s love for the system led him to become a professional implementer, eventually logging over 900 EOS sessions.

6. Transition to Implementing EOS for Others

• Dave’s EOS Implementer Journey:

  • After his own business exit, clients asked Dave to “do that thing” (EOS) for them.
  • Initially did so independently, before joining as a formal franchisee when EOS tightened their branding/licensing.
  • Found fulfillment in helping other businesses achieve clarity and freedom.

• Client Fit and Approach:

  • Dave seeks to work with entrepreneurial, open, honest, collaborative, and curious leaders—who are also up for a little humor:

    “If the owner is humble enough to hear it, that, hey boss, you suck, that's a good client for me. They also have to be kind of funny or at least enjoy my humor.” (55:23)

  • He emphasizes he gives away tools and help freely, even when it doesn’t result in paid engagement.

Notable Quotes & Memorable Moments

• On Outgrowing Old-School Sales:

  “At first, I failed...And I learned about this system called Sandler Sales...it's all questions...tell me, what are you hoping for?...when that change happened, it wasn't about price...it became about relationships.” – Dave, 18:08

• The Danger of Founder Bottleneck:

  “If you can't trust your team to do all that, you'll never grow past the lava lid. You can't grow past yourself.” – Dave, 35:15

• People Over Everything:

  “We have succeeded or we have failed based upon the people. And somebody would say, like, oh, well, it's process...Yes. But it's people that are building that process.” – Ryan, 39:22

• ‘Aha’ of EOS Implementation:

  “The structure you have may not be the structure you need and the people in that structure might not be the right people, period.” – Dave, 49:37

• On Client Selection:

  “If the owner is humble enough to hear it, that, hey boss, you suck, that's a good client for me. They also have to be kind of funny or at least enjoy my humor.” – Dave, 55:23

• Willingness to Help:

  “Even if people say, ‘Hey, Dave, I just want a couple tools, we actually don't want to hire you...’ I give it away. I have the joy of getting paid for it most of the time. But...I love to help if I can find the time, and if I can't, I'll find the time regardless.” – Dave, 60:44

Timestamps for Key Segments

• 00:00 – 09:17: Dave’s family background, early entrepreneurial journey, influence of father
• 14:41 – 21:13: Evolution in sales mindset, moving from “pushy selling” to curiosity-driven relationships
• 21:35 – 36:24: Scaling up, hiring mistakes, learning to let go, delegation & team interventions
• 40:46 – 48:24: Discovery of EOS, business struggles and turnaround, merging and exiting the agency
• 49:37 – 55:08: EOS implementation impact, rebuilding accountability, making hard team decisions
• 55:23 – 62:44: Client selection philosophy, giving back, maintaining joy and authenticity in the implementer role

Closing Style and Tone

Throughout the episode, both Dave and Ryan are candid, self-deprecating, and practical—leaning on stories, humor, and hard truths.

• Dave’s style is optimistic, relational, and direct (“I have to love them someplace else. Or maybe I don't even love them.” – 26:29).
• The conversation is rich in practical examples, making this a must-listen for any entrepreneur floundering in the “founder-bottleneck” or seeking to transform their own business structure with systems that create real freedom.

For Listeners

Connect with Dave Borland:

• [LinkedIn: Dave Borland]
• [EOSWorldwide.com: Dave Hyphen Borland]
• Open to questions, doesn’t charge for chats on tools or advice.
• Based in Albany, NY (prefers clients within a direct flight radius!).

Want to build a company that gives you actual freedom instead of just more headaches?

Start by asking: are your systems and people designed for growth—or are you the bottleneck? This episode offers both cautionary tales and a pathway out of the founder trap—with practical wisdom from someone who’s been on both sides.