Unlocked with Kristyn Drennen

Fewer than one in three companies that go to market actually close. It is rarely about the deal terms. It is about what is happening inside the owner between signing the letter of intent and walking away for good.

 In this candid conversation, host Kristyn Drennen talks with Denise Logan, therapist-turned-attorney-turned-exit expert and author of The Seller's Journey, about the emotional side of selling a business that almost no one prepares owners for. Denise shares her own story: building a 50-lawyer firm, burning out, and exiting on her own terms after years of advisors telling her to double down instead of listening to what she actually wanted.

 Together, Kristyn and Denise unpack:

• Why seller's remorse is the single most underestimated risk in any exit
• The two dependencies that have to be decoupled before a business is truly ready to sell: the business's dependency on the owner, and the owner's dependency on the business
• Why owners should start preparing three to five years before they plan to exit, not just financially, but emotionally
• The question Denise asks every client: what does work give you besides money and financial security?
• Why the right advisor is one who listens to the owner's voice instead of dominating the process
• A glimpse into family business transitions, and why vague promises like "one day this will all be yours" quietly damage both companies and families

 This conversation is a companion piece to TransformCXO's core belief that a business becomes more valuable, and more transferable, the less it depends on the person who built it.

Key Highlights:

• Denise's own disaster exit from her 50-lawyer law firm, and what she would tell owners not to repeat
• The difference between a transaction and a transition, and why most owners only prepare for one of them
• The 85 million dollar sailboat story: how an unrelated spousal conflict nearly killed a deal at 6.2x EBITDA
• Owner dependency and identity dependency, the two-way trap that keeps businesses unsellable
• Why getting a large payout does not solve the real question owners are afraid to ask
• A preview of Denise and Kristyn's upcoming follow-up conversation on family business transitions

Links and Resources:

• TransformCXO Exit Planning: https://www.transformcxo.com/art-of-the-exit-framework
• Denise Logan's website: https://deniselogan.com
• Book: The Seller's Journey by Denise Logan
• Connect with Denise on LinkedIn: https://www.linkedin.com/in/deniselogan/
• Explore more episodes: https://www.transformcxo.com/the-unlocked-podcast

Culture is easy to talk about and much harder to live. In this episode of Unlocked, Kristyn Drennen is joined by Sara Myers and Kelli Oberndorf, co-founders of Ekatā Group, for a grounded conversation about team health, leadership, accountability, and what it really takes to build a connected, high-performing company.

Sara and Kelli explain the meaning behind Ekatā, a Sanskrit word connected to unity, and how that idea shapes their work with leadership teams. Through their VIBE framework, which stands for Value, Integrity, Belonging, and Empowerment, they help teams move from vague culture language to real conversations, practical behaviors, and shared agreements that can actually be practiced inside the business.

Kristyn connects their work directly to TransformCXO’s mission of building sound businesses, steady leaders, and strong families. When a company has structure, clarity, and accountability, leaders are more stable. When leaders are stable and teams are healthy, people are able to do better work and go home with more capacity for the people they love. That is where operational transformation becomes deeply human.

This conversation is especially valuable for business owners and leadership teams who sense that something feels off inside the business, even if performance looks fine from the outside. The episode explores the warning signs of unhealthy teams, including burnout, role confusion, duplicated work, low trust, lack of candor, silence in meetings, and turnover. It also offers practical language for building accountability without fear, encouraging innovation without chaos, and creating a culture where people are willing to raise their hands before small issues become expensive problems.

Key Highlights

• Why team health is more than employee engagement, team culture, or another leadership buzzword.
• How Ekatā’s VIBE framework brings Value, Integrity, Belonging, and Empowerment into practical team conversations.
•  Why accountability must be clearly defined in action, not just used as a word leaders repeat.
• How psychological safety supports candor, ownership, problem solving, and better leadership decisions.
• Why healthy risk-taking requires clear boundaries, standards, and defined spaces for experimentation.
• The warning signs that a team may be less healthy than the owner or leadership team believes.
• How operational clarity and team health work together to create steadier leaders and more scalable companies.

Links and Resources

Learn more about Ekatā Group: https://www.ekatagroup.com

Contact Ekatā Group: [email protected]

Explore TransformCXO: https://transformcxo.com

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo

From the outside, success can look polished, beautiful, and almost effortless. The thriving business. The strong family. The bold life decisions. The meaningful work. The opportunities people dream about. For business owners and visionary leaders, it can start to feel like everyone else has somehow figured out how to scale, lead, parent, travel, serve, and build a beautiful life without carrying the same weight.

But that is never the full story.

In this episode of Unlocked, Kristyn launches a new recurring series arc: IG vs. IRL. The purpose is not to tear down success or minimize the beautiful parts of a full life. It is to tell the truth about what success actually requires behind the scenes: the pressure, trade-offs, logistics, lonely moments, family conversations, leadership decisions, and emotional discipline that rarely make it into the highlight reel.

This conversation explores what it feels like to build a meaningful life while carrying real responsibility. Kristyn and Amanda Barkey discuss business ownership, family rhythms, travel, resilience, reframing “busy,” and the intentional systems that help leaders keep moving with clarity instead of chaos. Amanda brings a rare blend of honesty and practicality as she talks about building and scaling businesses, navigating a major life move, raising five children, applying EOS tools in her family life, and learning how to stay present in whatever season she is in.

For business owners, this episode speaks directly to the private question many leaders carry: Why does success seem so easy for everyone else, when mine feels so full, complicated, and heavy at times? The answer is not that you are behind. It may simply be that you are finally seeing the real version of leadership, growth, and life design.

This episode is an invitation to stop comparing your behind-the-scenes reality to someone else’s curated version of success. The truth is, simple does not always mean easy. Full does not always mean wrong. And the life you once prayed for may still require structure, resilience, faith, communication, and intentional choices to sustain it.

Links and Resources

Learn more about Amanda Barkey: AmandaBarkey.com
Amanda’s EOS Worldwide profile: Amanda Barkey, Certified EOS® Implementer
Connect with Amanda Barkey on LinkedIn

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo

At some point in every business, the question isn’t “can you manage the finances?”
It’s “should you still be the one doing it?”

In this conversation, Kristyn sits down with Ryan Baer of CFO Selections to unpack a pattern they both see every day: high-performing business owners who have successfully delegated nearly every function… except finance.

Not because they love it. Not because they’re the best at it.
But because it feels too important to let go.

The problem? What once worked becomes the very thing that limits growth, clouds decision-making, and quietly erodes the value of the business.

This episode challenges you to take an honest look at your finance seat and whether staying in it is truly serving your business anymore.

What You’ll Learn

• Why so many business owners stay stuck in the finance seat longer than they should
• The difference between having financial data and actually having clarity
• How strong finance leadership turns numbers into simple, actionable decisions
• The behavioral side of finance and why control is often the real issue
• What “owner dependency” really looks like (and how it impacts value)
• The most common blind spots when owners think they’re ready for an exit
• How to identify the right level of financial support for your stage of growth
• Why process, controls, and structure matter more than most reports
• The real signals that it’s time to step out of the finance seat

The Hard Truth Most Owners Avoid

You didn’t build your business by accident.
But you may be holding it back without realizing it.

Many owners stay in the finance seat because:

• “I’ve always done it this way”
• “I don’t fully trust anyone else yet”
• “I should understand this before I hand it off”

The Reality: 

If you can’t clearly explain what’s happening in your numbers and what to do about it, 
you’re not leading your business from a position of clarity. You’re reacting. Over time, that gap shows up in slower decisions, missed opportunities, and increased risk.

A Better Way to Think About It

The goal isn’t to remove yourself from your financials. It’s to elevate how they serve you. Great finance leadership doesn’t just produce reports. It answers three questions:

• What’s happening?
• Why is it happening?
• What should we do next?

If your current setup isn’t doing that, it’s not a reporting issue—it’s a leadership gap.

Connect with Ryan Baer & CFO Selections

• Email Ryan:[email protected]
• Connect on LinkedIn:  Ryan’s LinkedIn Profile
• Learn more about CFO Selections:  Website Link

Resources & Next Steps

• Sign up for the TransformCXO Sound, Steady, and Strong Newsletter
• Take the Founder Freedom Score
• Connect with TransformCXO: Contact TransformCXO

Many founders start their businesses because they love building, creating, and solving big problems — but somewhere along the way, they become the bottleneck. In this episode of Unlocked, Kristyn Drennen is joined by EOS Implementer Charlie Rhea to break down the leadership structure that helps founders scale without burning out: the visionary–integrator partnership.

Charlie explains the critical distinction between an EOS Implementer and an Integrator, why those roles are often confused, and how they work together to support healthy execution. Kristyn shares real-world examples from her work as a fractional integrator, including why asking a visionary to also lead, manage, and hold a leadership team accountable almost always backfires.

Together, they dive deep into the visionary seat — what it is, what it is not, and why so many founders struggle to step fully into it. From protecting culture and casting vision to creating space for strategic thinking, this conversation gives founders a clear picture of what leadership looks like when it’s functioning well.

This episode is especially timely for leaders heading into annual planning, navigating growth complexity, or feeling stuck between strategy and execution. If you want your business to grow beyond you — without losing control — this conversation will give you practical clarity on what needs to change next.

KEY HIGHLIGHTS

• The difference between an EOS Implementer and an Integrator — and why confusing the two creates friction
• Why visionaries struggle when they try to lead, manage, and hold their teams accountable
• What the visionary seat actually owns when it’s working well
• How the visionary–integrator relationship drives leadership team effectiveness
• Practical ways to keep vision alive inside the business — not just on paper

LINKS & RESOURCES

• Discover your Founder’s Freedom Score! Free tools, instant results: Founder's Freedom Score
• Learn more about EOS Worldwide: https://www.eosworldwide.com
• Connect with Charlie Rhea on LinkedIn
• Recommended Books:
  • Traction by Gino Wickman
  • Rocket Fuel by Gino Wickman
  • Living Forward by Michael Hyatt & Daniel Harkavy

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo 

What actually makes a business operating system work — and why do so many fail to deliver the clarity leaders expect?

In this episode of Unlocked, Kristyn Drennen is joined by John Kitchens, a seasoned business coach with deep experience in EOS, Scaling Up, and operational leadership. Together, they unpack what operating systems really are, when a business is ready for one, and why the “install and forget” mindset leads to disappointment.

The conversation goes far beyond frameworks. John and Kristyn explore the intersection of operating systems, financial acumen, AI, and leadership development — including the growing divide between transactional businesses and those built on experience and long-term value. John also shares why mentorship and leadership pipelines matter more than ever as AI reshapes entry-level roles.

This episode is a must-listen for founders, integrators, and leadership teams who want structure without rigidity — and growth without burning out.

Key Highlights

• What a business operating system really is (without the jargon)
• How to know when your company is ready for EOS, Scaling Up, or another framework
• Why financial ownership is critical in the integrator role
• AI as a thought partner — not a crutch
• The future of leadership, mentorship, and experience-driven businesses

Links & Resources

• Connect with John: https://johnkitchens.coach
• John Kitchens Coach Podcast
• Follow John on LinkedIn & social platforms: @JohnKitchensCoach

Book Recommendations from this episode

• Traction – Gino Wickman
• Scaling Up – Verne Harnish
• The AI-Driven Leader – Geoff Woods
• Unreasonable Hospitality – Will Guidara
• Hug Your Customers – Jack Mitchell
• Raving Fans – Ken Blanchard & Sheldon Bowles
• Giftology – John Ruhlin

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo 

In this deeply personal and practical conversation, Kristyn Drennen sits down with TransformCXO co-founder Paulina Walters to unpack what it truly means to operate a business as a ministry—without sacrificing performance, profitability, or accountability.

Drawing from Paulina’s journey through C12 and her evolution as a leader, the conversation explores how faith, stewardship, and intentional leadership practices shape healthier organizations. Together, they discuss how leaders often operate from depletion rather than purpose, and how shifting that posture can radically transform culture, retention, and results.

Kristyn and Paulina also share the framework that anchors TransformCXO’s mission: Sound Businesses. Steady Leaders. Strong Families. The episode highlights why leadership steadiness creates organizational calm, how people-first cultures outperform over time, and why profit and purpose are not competing priorities—but reinforcing ones.

This episode is for business owners and leaders who feel stretched thin, are questioning how they show up at work and at home, and want to build something meaningful without doing it alone.

Key Highlights

• What “business as a ministry” actually means in practice
• Why leading from depletion undermines both people and performance
• How people-first leadership improves retention and long-term profitability
• The role of peer advisory groups like C12 in leadership formation
• The ripple effect from steady leaders to families and communities

Links & Resources

• Connect with Paulina Walters on LinkedIn
• Explore TransformCXO: https://transformcxo.com
• Get your Founder’s Freedom Score: https://transformcxo.com

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo 

Mergers test everything: leadership, communication, trust, and culture. Many organizations focus on systems, contracts, and integration plans, but overlook the human experience inside the transition.

In this episode of Unlocked, Kristyn is joined by Sara Hoffman, Managing Partner at Conexus Insurance Partners, for a candid conversation about designing a people-first organization in the midst of growth and change.

Sara shares how Conexus approached their merger with intention, using clear leadership rhythms, consistent communication, and shared accountability to keep people aligned. Rather than relying on slogans or values statements alone, the leadership team focused on building structures that reinforced trust and clarity week after week.

You’ll hear how separating ownership conversations from leadership execution created psychological safety, why predictable communication rhythms reduced uncertainty, and how peer-to-peer recognition helped bring core values to life in a tangible way.

This episode is especially relevant for leaders navigating mergers, acquisitions, partnerships, or rapid growth who want to protect culture while still driving execution.

What You’ll Learn

• Why most mergers struggle with culture, even when the strategy is sound
• How leadership rhythms and meeting structure shape the employee experience
• The importance of separating ownership dynamics from leadership execution
• How peer recognition reinforces values more effectively than top-down messaging
• What it really means to design a people-first organization, not just talk about one

About the Guest

Sara Hoffman is a Managing Partner at Conexus Insurance Partners, where she helps lead a growing, people-centered organization built on clarity, trust, and intentional leadership. Sara brings a grounded, practical perspective on culture, communication, and what it takes to lead well through change.

Links & Resources

• Learn more about Conexus Insurance Partners
• Connect with Sara Hoffman on LinkedIn
• Explore TransformCXO and fractional Integrator/COO support

In this episode of Unlocked, Kristyn sits down with organizational transformation expert Noel Andrews-Sotta to explore why change management is far more relevant and human than leaders realize. Noel introduces her Change Compass, a simple framework that helps teams navigate uncertainty with clarity, confidence, and stability.

Most leaders think change management is only necessary in the “big” moments: acquisitions, restructures, major system rollouts. But the truth is, the micro-changes happening inside your business every day have a far greater impact on performance, culture, and emotional bandwidth.

In this deeply practical episode, Kristyn and Noel unpack the subtle ways change shows up in an organization and how leaders can guide their teams through it with more empathy, steadiness, and strategic clarity.

Noel shares her signature framework, The Change Compass, built around four simple but powerful questions that reveal what’s truly shifting, what’s stable, what’s known, and what still needs clarity. This tool has helped executive teams calm chaos, align messaging, resolve issues faster, and rebuild trust in moments of uncertainty.

Listeners will learn how to apply this method during weekly leadership meetings, one-on-ones, process updates, team changes, and any moment where overwhelm or ambiguity begins to impact performance.

Whether you're scaling quickly, restructuring, adding new roles, or simply navigating everyday disruptions, this episode gives you a clear and human-centered way to lead people through change, big or small.

Key Highlights

• Why change management is underutilized in small, everyday moments
• The psychology behind why teams resist change
• How leaders unintentionally create more instability
• How to facilitate Noel’s Change Compass with your team
• The differences between “what is changing” vs. “what feels like change”
• How to rebuild trust when you don’t have all the answers
• Why the change curve matters and how to normalize it
• How to shift teams from a victim mindset to a hero mindset

Links & Resources

Connect with Noel on LinkedIn
Learn more about TransformCXO: https://transformcxo.com
Change Curve Toolkit (recommended resource): Link

Stay Connected

If this episode resonates, share it with a fellow leader who needs to hear it. And if you’re ready to unlock your capacity and lead from your zone of genius, book a conversation with Kristyn and the TCXO team.

🎧  👉 Subscribe to Unlocked with Kristyn Drennen on Spotify, Apple, or YouTube — and share this episode with a visionary leader who needs to hear it.

Learn more about TransformCXO: https://transformcxo.com

Connect with Kristyn Drennen on LinkedIn: Kristyn’s LinkedIn 

Follow Kristyn on Instagram: @kristyndrennencxo 

What if your biggest obstacle isn’t lack of drive, but the very habits that made you successful? In this candid and practical episode, host Kristyn Drennen talks with executive coach David Shrum about what happens when high achievers plateau and how Meta Performance™ Coaching helps leaders break through the invisible ceilings that keep them stuck.

David shares insights from his own leadership journey and explains how the shift from high performance to meta performance changes everything — from how you set goals to how you lead your team. Together, Kristyn and David unpack:

• The subtle “stuckness” that hides behind success.
• How curiosity, not advice, is the engine of great coaching.
• The athlete’s mindset — why growth requires getting back in the gym.
• The difference between performance at work and transformation through work.
• What to look for when hiring a truly great executive coach.

Whether you’re an executive, entrepreneur, or lifelong learner, this conversation will challenge your assumptions about growth and inspire you to pursue the version of yourself you haven’t yet met.

Key Highlights

• The “high performer problem” — and why doing more isn’t always the answer.
• How Meta Performance Coaching shifts focus from being the best to becoming limitless.
• Lessons from Amazon and Jeff Bezos on vision beyond success.
• The power of curiosity over advice in true coaching relationships.
• The connection between personal and professional transformation.

Links & Resources

• Learn more about TransformCXO Executive Coaching: https://transformcxo.com/coaching
• Connect with David Shrum on LinkedIn: https://www.linkedin.com/in/david-shrum
• Book Recommendation: Beyond High Performance by Jason Jaggard

Explore more episodes at TransformCXO.com/Unlocked