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Leader Roundtable

Leadership gets quieter as decisions get heavier.

A private forum for leaders making consequential decisions.

The higher you climb, the fewer people truly understand what you’re navigating. Your board has agendas. Your team needs confidence. Your advisors speak to narrow domains. Where do you go when you need to think out loud without performing?

You're not alone in feeling alone.

The research is clear: executive isolation isn’t a character flaw—it’s a structural reality. The very skills that got you here (self-reliance, decisive action, carrying the weight) become liabilities when complexity outpaces individual capacity.

The cost isn’t just personal. Isolation degrades decision quality, increases blind spots, and leads to preventable mistakes that compound over time.

50%

of CEOs report feeling lonely in their role

61%

believe isolation hurts their performance

2/3

don’t receive outside leadership advice

2×

more likely to feel isolated than other employees

Sources: RHR International CEO Survey; Stanford Graduate School of Business & The Miles Group, 2013 Executive Coaching Survey; Perceptyx Workplace Research

What this is — and what it isn't

✔️ This is

A confidential space where uncertainty is allowed
Facilitated dialogue with peers who understand the weight
Honest feedback from people with no agenda
Strategic thinking time away from the daily grind
Accountability to the goals you set for yourself
A room where you don't have to perform

Ⅹ This isn't

A networking group or referral exchange
A lecture series or training program
Group therapy or a support group
A sales opportunity disguised as community
Another obligation on your calendar
Generic advice from people who haven't been there

The conversations we have

Real challenges. No easy answers. The kind of decisions that keep you up at night.

"

We’re at $12MM and I don’t know whether to pursue the acquisition or grow organically.

"

My board wants me to scale faster, but my gut says we’re not ready.

"

I haven’t taken a real vacation in three years. Something has to change.

"

My co-founder and I aren’t aligned anymore, and I don’t know how to have that conversation.

"

I’m the bottleneck in my own company and I don’t know how to get out of the way.

"

I need to let go of my COO, but she’s been with me since the beginning.

Sound familiar? That’s why the room exists.

How it works

Structured enough to create value. Flexible enough to address what matters most.

Monthly Sessions

2-Hour facilitated meetings, virtual for flexibility

Small Group

Limited to 8 participants for depth and trust

Confidential

What’s shared stays in the room, period

Facilitated

Expert guidance to ensure every session delivers value

Who this is for

Membership Criteria

~$10MM+

Annual Revenue (or) Leaders navigating growth-stage complexity — not those looking for a quick exit.

C-Suite

CEO, President, Founder, or Senior Executive

Non-Competing

Industries for candid discussion

This isn’t for everyone. If you’re not willing to show up, prepare, and engage—we shouldn’t work together. But if you’re tired of going it alone and ready to learn from others who’ve been where you are, let’s talk.

Dan Kent

Founder & Facilitator

Former COO

30 Years Business Leadership

Executive Coach

Finance & Operations Background

Host, Clearing Obstacles Podcast

I’ve spent nearly 30 years in business ownership and executive leadership—most recently as COO for a systems-integration firm serving municipal and industrial clients across California, where I navigated the complexities of cash constraints, growth decisions, and building teams under pressure.

I’ve been in rooms where I was the one making the consequential call with no one to talk to. I know what it costs. And I know what it would have meant to have trusted peers who understood the weight without needing it explained.

I’m the host of the Clearing Obstacles Podcast, where I’ve interviewed exceptional leaders on what actually works.

I created Leader Roundtable because the best leaders I know aren’t the ones who figured everything out alone. They’re the ones who were smart enough to surround themselves with people who made them better.

What leaders are saying

"

“I have worked with Dan Kent for five years. As the sole owner of my business, I have found his knowledge and experience to be invaluable in guiding me through complex decisions and supporting the continued growth and success of my company.”

Brian Kazak, CEO
Landforms Inc.

"

“Dan Kent has a rare gift for making you feel truly seen and heard. He meets you exactly where you are, and then gently helping you discover the “growth edges” that will move you forward. His listening is extraordinary, and he doesn’t just notice your strengths. He has a way of naming them so clearly that you walk away with more confidence and clarity than you came in with. I experienced his “magic” firsthand, and I’m grateful for the thoughtful, authentic way he elevates others.”

Meredith Bell, President

Grow Strong Leaders

"

“As a CFO in the construction industry, being a woman can often feel like you are on an island. Dan has consistently provided an objective outside perspective with honesty and clarity, advising both me and my team through numerous challenges and opportunities. I am grateful to have him as a valued part of our team.”

K.K.

"

“Fifteen years ago, I met a fellow business leader who would become one of my most trusted confidants. Dan has a gift for seeing the whole picture—and the whole person. His insights cut through the noise, but it’s his questions that change you. Above all, Dan genuinely cares—not just about your business, but about the person you’re growing into. And that makes all the difference.

Christina Ellis, Founder
Business by Intention, Business Development Strategist, Author, Artist, Speaker

What you gain

Beyond the intangible value of trusted peers, these are the outcomes that matter most.

Sharper Decision-Making

Pressure-test ideas before you commit. Identify blind spots before they cost you.

Accelerated Learning

Learn from others' wins and losses without paying the tuition yourself.

Genuine Accountability

Commit to action with peers who will follow up—not just nod along.

Sustainable Leadership

The weight doesn't disappear, but it gets lighter when you're not carrying it alone.

Investment

$10,000

per year

or $1,000/month

Your membership includes:

12 facilitated monthly sessions (Two-hours each)
Confidential peer advisory group of up to 8 leaders
Curated membership from non-competing industries
Direct access to Dan for between-session support
Structured accountability and follow-through

Limited to 8 participants. Once full, the group closes.

Good decisions don't start with answers.

They start with the right questions—and the right people in the room to help you think through them. Let’s have a confidential conversation to see if this is the right fit.