Confessions of an Implementer – S2E22

Beyond Revenue: Redefining Success In Business with Michael Richman
Host: Ryan Hogan
Guest: Michael Richman
Release Date: November 12, 2025

Episode Overview

This episode explores the true meaning of business success beyond just growing revenue, as Ryan Hogan interviews Michael Richman—serial entrepreneur, EOS Implementer, and current President of EO Los Angeles. The discussion covers Michael’s entrepreneurial journey, lessons learned building and selling a family business, the transformative power of EOS, evolving definitions of success, and insights into facilitation, legacy planning, and adapting to new technologies like AI.

Michael reveals the realities of working within a family business, the pivotal role of community through EO (Entrepreneurs’ Organization), and offers practical advice on implementation, partnership, exiting a business, and embracing what it means to "get more of what you want" from your company.

Main Discussion Points and Insights

What Does Success in Business Really Mean?

• Success Isn’t Just Revenue:

  • Michael emphasizes that business owners often seek more than money—such as freedom to travel, peace of mind during vacations, or time with family.
  • "What EOS is, is it gives you more of what you want from your business… Some of them it is to grow revenue, and that’s great. But some of them it’s not." – Michael [00:00], [33:23]

• Redefining Metrics:

  • Owners may prioritize personal freedom, operational independence, or building a legacy, rather than simply chasing top-line growth.

Entrepreneurial Journey: From Family Business to EOS

• Origins in Entrepreneurship:

  • Michael’s family history spans milk delivery (with a legendary mob connection) and awning manufacturing.
    • "Entrepreneurship, I think, was in the blood in the family." – Michael [08:59]
    • Anecdote: His grandfather’s role in bootlegging during Prohibition for Meyer Lansky. [09:00]

• Entering the Cabana & Awning Business:

  • Initially a commercial banker, Michael moved into his father’s business after another acquisition fell through.
  • He bought out one partner, becoming 50-50 co-owners with his father. [11:09]

• Lessons in Running/Niching Out Business:

  • Focused on scaling through process and relationships (e.g., landing accounts like Carl’s Jr. and Panda Express), not technical expertise in manufacturing.
    • "We knew how to run a business and how to grow a business. We knew how to look at new products and bring those into the business." – Michael [13:13]

Implementing EOS: Self-Implementation vs. Professional Support

• Self-Implementation Experience:

  • Michael implemented EOS himself after reading Traction, finding immediate clarity—“it turned the lights on" in his business.
  • Realized later the value of having a third-party facilitator for honest conversations and team health.
    • "Having a third party in that room changes everything." – Michael [04:00]
    • Example: Closely evaluating roles revealed a beloved staff member was underperforming, leading to positive and honest transitions. [21:27]

• The Value an Implementer Brings:

  • Third-party EOS Implementers ask tough questions, force candid dialogue, and help dig into root causes.
    • "We’re all implementing the same material, but the differentiating factor is the way we facilitate and we’re able to ask those hard questions." – Michael [04:48]

• Common EOS Outcomes:

  • Turnover on leadership teams is common as right people/right seats are clarified.
    • "I see it definitely a lot more being an implementer now… there’s major turnover in teams when we start really implementing." – Michael [24:51]
  • Businesses become far more valuable and ‘turnkey’ through process documentation and strengthening core values.
    • "When they were able to come in and buy the company, all of a sudden we had everything documented... All the processes were written down and it allowed the new ownership to come in and say, okay, here are the keys, we just need to put in the ignition and drive." – Michael [23:36]

Navigating Family Partnerships and Exits

• On 50-50 Partnerships:

  • Michael insisted on an equal split to prevent feeling like an employee.
    • "I refused to buy the business unless we were 50/50 partners, because otherwise I’d always feel like an employee… I didn’t think that was healthy for the business." – Michael [18:26]
  • Decision-making as equals (sometimes one wins, sometimes the other).

• Building To Sell:

  • Focused on building value through great service and product, knowing this would lead to acquisition interest.
    • "We knew that if we did that, we’d have an acquisition." – Michael [17:14]
  • Their sale emerged from an EO connection—consultants preparing them for sale ultimately became buyers.

• Biggest Lesson from the Sale:

  • New owners quickly veered from established processes and failed, leading to bankruptcy.
    • "Try not to deviate from the processes too quickly… Really going into a business and understanding why certain things were done is really the way it should be done." – Michael [36:01], [37:31]
  • Ryan notes many new owners can’t resist “tinkering,” often at the business’s peril.

Life After Exit: Coaching, Facilitating, Giving Back

• Transition to EOS Implementation and Facilitation:

  • Inspired by coaching and supporting others (EO, USC, Mastermind groups), Michael leaned into helping business owners find fulfillment—not just profit.
    • "I love coaching. I love helping business owners. So what should I do with the rest of my life? I should help business owners get more of what they want from their business." – Michael [26:32]

• Facilitating Mastermind Groups:

  • Leads both high-net-worth and industry-specific (e.g., T-shirt printers) groups to tackle issues from legacy planning to technical troubleshooting.
    • "A group of people getting together and understanding what they do and being able to help each other." – Michael [28:23]

• Common Challenges Post-Exit:

  • What does success mean? How to leave money to the next generation? What comes next?
    • "What does my legacy look like? What am I gonna do next? I’m antsy after owning a business and selling a business." – Michael [30:15]

The Art of Facilitation and Listening

• Keys to Great Facilitation:
  • Curiosity and the skill of asking questions that dig deeper.
    • "Curiosity. You have to want to know the next piece of information… really force them to dig down into what does this mean?" – Michael [31:04]
  • Ryan shares the importance of not scripting your next question in your head, but being present in the conversation. [31:56]

Technology, Change, and Looking Ahead

• On Implementing Change as a Buyer:

  • Michael cautions new owners—observe first, act slowly (90-180 days) to avoid unnecessary disruption.
    • He shares real-world consequences of switching from handwritten orders to computerized systems prematurely.

• Reflections on AI:

  • AI’s pace is unprecedented; many business owners fear being left behind.
    • "We’ve never lived in a time period like this… four years ago, three years ago nobody knew what AI was and now everybody feels like they can’t get by a day without using AI." – Michael [43:05]
  • Recommends business owners focus on integrating AI in meaningful, practical ways relevant to their operations; don’t follow AI hype if it doesn’t fit.

• Looking for Businesses to Buy:

  • Sees opportunity in niche, boomer-owned businesses lacking succession plans.
    • "These are businesses that are wildly successful… There’s a lot of them out there that don’t know what to do next and how to graduate or retire." – Michael [41:07]

• Business Acquisition Advice:

  • Recommends old-school outreach (cold letters, networking) over high-tech or AI-driven searches when looking for acquisition opportunities.

Notable Quotes & Memorable Moments

• On Value Beyond Revenue:
  • "What EOS is, is it gives you more of what you want from your business. Some of them it is to grow revenue, and that’s great. But some of them it’s not." – Michael [00:00], [33:23]
• On Partnerships:
  • "I refused to buy the business unless we were 50/50 partners, because otherwise I’d always feel like an employee." – Michael [18:26]
• On Honest Conversation:
  • "Having a third party in that room changes everything." – Michael [04:00]
• On the Risk of Fast Changes:
  • "Going in there and changing things out… Try not to deviate from the processes too quickly." – Michael [36:01]
• On Curiosity and Facilitation:
  • "Curiosity. You have to want to know the next piece of information…" – Michael [31:04]
• On Legacy:
  • "What does my legacy look like? What am I gonna do next? I’m antsy after owning a business and selling a business. How do I kind of itch that scratch?" – Michael [30:15]

Key Timestamps

• [00:00] – Redefining business success: what EOS truly delivers.
• [02:02] – Michael’s EO journey and initial foray into entrepreneurship.
• [04:00] – Realizing the limitations of self-implementing EOS.
• [08:59] – The Richman entrepreneurial legacy: milk distribution in NYC.
• [11:09] – Structuring family partnerships and leadership roles.
• [13:13] – Scaling niche manufacturing: strategies that work.
• [18:26] – 50/50 partnerships: dynamics and lessons.
• [21:27] – EOS as a tool for “turning the lights on” in business.
• [23:36] – The value of process and documentation in a sale.
• [26:32] – Michael’s “second act” as a facilitator and coach.
• [30:15] – Universal challenges for entrepreneurs post-exit.
• [31:04] – Facilitation as a skill rooted in curiosity.
• [33:23] – The real result EOS offers: freedom, clarity, choice.
• [36:01] – Lessons from a failed handoff: don’t rush change post-acquisition.
• [41:07] – Opportunities in boomer-owned niche businesses.
• [43:05] – On the rise and reality of AI adoption in traditional business.

Final Takeaways

• Business success is as much about fulfillment and freedom as about growth—define what “more” means for you.
• Honest facilitation (internally and externally) is crucial for clarity, health, and value in leadership teams.
• The best time to make changes is after you understand the business’s history—don’t “tinker” prematurely after a sale.
• There are still rich opportunities in traditional, overlooked businesses, especially those with looming succession gaps.
• AI is powerful, but practicality should drive implementation—not fear or hype.

Connect with Michael Richman

• Website: MichaelRichman.me

(For clarity and readability, some quotes are lightly edited for length while preserving the original language and tone.)