Podcast Summary: Confessions of an Implementer

Episode: "Leading with Compassion: Why Empathy Is A Leadership Superpower with Chris White"

Host: Ryan Hogan
Guest: Chris White (former EOS implementer, co-founder of 90, System and Soul, Micro Business Academy, Profit Pro)
Date: September 17, 2025

Main Theme Overview

This episode explores the power of compassionate, empathetic leadership through the experiences of Chris White—a serial entrepreneur and executive coach known for co-founding several influential business operating systems, such as 90 and S2 (System and Soul). Chris shares his journey from SaaS entrepreneur to pioneering implementer and thought leader in business operations, emphasizing that true leadership means genuinely caring for people, fostering healthy conflict, and continually learning and growing. Central to the discussion: empathy is not a soft skill but "a leadership superpower" tailored to today's work environments.

Key Discussion Points & Insights

Chris White's Entrepreneurial Journey and Partnerships

[01:15]–[08:23]

• Chris credits his success to great partnerships, not solo achievement.
• Background: grew up in an entrepreneurial family as one of eight brothers, initially disinterested in entrepreneurship.
• Got involved with EOS after witnessing its transformative power in a $10M company—a life-changing moment.
• Leveraged SaaS experience to help digitize EOS tools, leading to the creation of 90 (a leading EOS software).
• Left 90 due to health issues; notes importance of choosing partners with complementary skills and shared passion.
• Pride in building “two operating systems” (90 and S2), both serving different market needs.
• Quote:

  "All I ever wanted to be was a teacher and a coach. This book changed my life because it allowed me to become a teacher and a coach...just at the executive level." —Chris [07:11]

The Nature of Enduring Partnerships

[08:23]–[13:29]

• Effective partnerships require both alignment on mission and willingness to engage in healthy conflict.
• Seek partners smarter than oneself and embrace “same page” meetings to resolve friction.
• Clear roles, radical candor, and trust are fundamental.
• “Ignoring stuff is the beginning of the end”—never avoid difficult conversations.
• Quote:

  “Great leaders get out of the way of people. They let them move.” —Chris [11:36]

Healthy vs. Unhealthy Conflict in Leadership

[13:29]–[20:21]

• Healthy conflict focuses on the issue, not attacking character; prepare the other for “a sting” but never cross lines.
• Sharing stories of personal mistakes—learning from failing to be self-aware as a leader.
• Recommends being “inwardly sound and others focused” (Tim Spiker, The Only Leader Worth Following).
• Importance of understanding the impact you have on others, especially for big personalities.
• Memorable Story:
  After an angry outburst, Chris’s coach pointed him to a key book on leadership. Realized he was unconsciously intimidating, learned to reflect:

  “You just didn’t realize the impact you are having on others.” —Chris, recounting his coach’s advice [18:44]

• Created a TED talk and workshop on self-awareness in leadership as a result.
• Quote:

  "Even at the age of 60, I still have something to learn." —Chris [19:49]

Evolving Leadership and the Value of Empathy

[20:21]–[27:33]

• Good leaders invest in continual learning; formal training is essential (e.g., storytelling, psychology).
• “Pitch Anything” and “Radical Candor” recommended reads.
• Empathy and care are the foundation—tough conversations must come from a place of genuine concern.
• “Fundamentally have to care about your people…and be willing to piss them off a little bit because you’re going to challenge them to be better, but in such a way that it’s appropriate.” —Chris [24:45]
• Set expectations up front, clarify career paths, and use regular coaching conversations to build trust.

Practicing Compassionate Leadership in the Workplace

[27:33]–[31:58]

• Empathy starts during the interview; clarify role, responsibilities, and what support looks like.
• “Live open and honest”—leaders must model transparency for the team.
• Coach employees rather than “manage to the basics”; address underperformance quickly but compassionately.
• Quote:

  "If you can be a compassionate leader and show empathy...and be willing to be tough and candid, but be human—nobody wins from this or berating. Nobody wins in any of that leadership styles anymore." —Chris [31:32]

The One-on-One Debate: Frequency & Method

[31:58]–[37:40]

• Mixed opinions on the value of regular one-on-ones—some say “don’t do them,” others see value.
• Chris advocates for quarterly performance reviews, frequent team/cadence meetings, and encourages bringing issues directly but with boundaries.
• Shares the “1-3-1” method: For every 1 problem, bring 3 solutions and together select the best one. This discourages dependency and encourages ownership.
• Quote:

  "For every one issue you have, in order to see me, you must bring three solutions so that I can help you pick the best one." —Chris [36:26]

Boundary-Setting and Protecting Leaders’ Time

[37:40]–[40:50]

• Open door policies can backfire; repeated interruptions can sap productivity.
• Leaders must learn to protect their own time and teach others to solve problems at the appropriate level.
• Train well, trust, and “get out of the way” without abdicating responsibility.

Leadership Styles: Hands-On vs. Hands-Off

[40:50]–[43:27]

• Discusses differences between hands-off and intensely hands-on leaders (Elon Musk, Steve Jobs).
• Both approaches can be successful—what matters is clarity, brilliance of team, and alignment toward “changing humanity.”

Giving Back: Veteran & First Responder Initiatives

[43:27]–[49:02]

• Chris is launching an initiative (Micro Business Academy, ProfitFirstApp.com) to assist veteran and first-responder entrepreneurs with business basics, especially cash flow.
• Shares personal story of learning financial acumen the hard way—calls for demystifying business finance for all.

Digitizing "Profit First": The Next Venture

[49:02]–[57:45]

• Story of transforming the book Profit First by Mike Michalowicz into a SaaS platform for easier small business cash management.
• Describes the challenge: most small businesses and even many entrepreneurs lack clear, actionable financial habits.
• Explains the book’s shift from “Sales – Expenses = Profit” to “Sales – Profit = Expenses”—a simple but transformative mindset.
• Notes overlap between entrepreneur struggles and solutions that apply to all, not just business owners.
• Quote:

  “Entrepreneurs...get to the end of the year, ‘where’s all my profit?’ Where’s my money?...It’s the envelope method...My mom used to use it in our house.” —Chris [55:04]

Notable Quotes & Memorable Moments

• On leadership transformation:

  "This book changed my life because it allowed me to become a teacher and a coach just at the executive level."
  [07:11] —Chris White

• On partnership selection:

  “Surround yourself with smart people. That includes smarter than you.”
  [10:51] —Chris White

• On radical candor:

  “You fundamentally have to care about your people and if you do, then you’re going to be willing to piss them off a little bit because you’re going to challenge them to be better, but in such a way that it’s appropriate.”
  [24:45] —Chris White

• On being a leader worth following:

  "Even at the age of 60, I still have something to learn."
  [19:49] —Chris White

• Empathy in leadership:

  "If you can be a compassionate leader and show empathy and...be human—nobody wins from this or berating. Nobody wins in any of that leadership styles anymore."
  [31:32] —Chris White

• On conflict and ego:

  “Healthy conflict is like, ‘Hey, I’ve got to talk to you about a particular issue...it might sting a little, but I just want to get it out...’ unhealthy is when it gets personal.”
  [14:41] —Chris White

• Practical wisdom:

  "Train them up so good, right? And then get out of their way. That's what great leaders do."
  [39:23] —Chris White

Segment Timestamps

• Chris's Origin, Background, EOS Story: [01:15]–[08:23]
• Partnerships and Finding the Right People: [08:23]–[13:29]
• Healthy vs. Unhealthy Conflict: [13:29]–[20:21]
• Empathy and Building Trust: [20:21]–[27:33]
• Coaching, Setting Expectations, and Feedback: [27:33]–[31:58]
• One-on-One Meetings and "1-3-1" Framework: [31:58]–[37:40]
• Boundary Setting and Leader Productivity: [37:40]–[40:50]
• Leadership Styles—Hands-Off vs. Hands-On: [40:50]–[43:27]
• Supporting Veteran & First Responder Entrepreneurs: [43:27]–[49:02]
• Profit First App, Financial Acumen, and Personal Growth: [49:02]–[57:45]
• Closing, Ways to Connect & Final Messages: [57:45]–[59:15]

Other Resources Mentioned

• Traction by Gino Wickman
• Radical Candor by Kim Scott
• Ego Is the Enemy by Ryan Holiday
• The Only Leader Worth Following by Tim Spiker
• Pitch Anything by Oren Klaff
• Profit First by Mike Michalowicz
• "1-3-1" Problem-Solving Technique
• Micro Business Academy (microbusinessacademy.io)
• ProfitFirstApp.com

Summary Takeaway

Chris White’s career illustrates that enduring business transformation is always rooted in people—through partnerships, empathy, and a relentless commitment to self-improvement. He urges leaders to balance accountability and compassion, set clear boundaries, and never stop learning. His ventures continue to bridge gaps—from digitizing proven methodologies like EOS and Profit First, to empowering small business owners—including veterans and first responders—to succeed on their own terms. Perhaps most powerfully, Chris models the humility to learn from every mistake, making self-awareness and empathy not just leadership assets, but superpowers.