Whetstone Mastermind Groups

Sharpen Your Thinking. Strengthen Your Leadership.

Better businesses begin with better thinking.  And better thinking happens when leaders challenge assumptions, share perspectives, and learn from one another.

Over 10+ Years of Impactful Peer-to-Peer Advisory Leadership

Leadership can be lonely.

You’re making the big decisions, but without a trusted circle of peers, it’s easy to feel stuck, second-guess yourself, or struggle to scale. Not because you’re alone. But because fewer people challenge your thinking. Whetstone exists to change that.

Whetstone Personal Board of Director

A whetstone doesn’t replace the blade.

It sharpens it.

Whetstone exists to sharpen leaders through thoughtful challenge, honest conversation, and shared experience.

Better Questions. Better Decisions. Better Leaders.

Accountability

Structured groups ensure you follow through on your goals, so you can stop overthinking and start executing with confidence.

Strategic Insights

The best leaders aren’t the ones with the fastest answers. They’re the ones surrounded by people willing to ask better questions. 

Thinking Partners

Every leader needs a place where they can think openly, challenge assumptions, and grow alongside peers committed to becoming better leaders.

What to Expect from Whetstone

01

Attend a Visitor Day

Experience a live Whetstone session and see firsthand how peer accountability and strategic problem-solving drive real results.

02

Engage in Meaningful Discussions

Join high-impact conversations with successful leaders who will challenge your thinking, share insights, and offer support.

03

Grow Faster with Peer Accountability

Gain clarity, confidence, and a trusted network to help you make better decisions and scale your business with less stress.

Unlock Your Potential

Helped Me Scale

“Joining Whetstone was one of the best decisions I’ve made. The support, accountability, and strategic advice have helped me scale faster than I thought possible.”

Bryant Jones, COO

Pro Moto Billet

Got Me Past Roadblocks

“My Whetstone group has been very helpful in getting me past my roadblocks, challenging my thinking and keeping me on task and accountable.”

Terrie Trevino, Sales Executive

PayneWest Insurance

Invaluable Feedback

“Sometimes I get stuck looking at things only through my industry lens. The feedback from my Whetstone group has been invaluable. I highly recommend Whetstone if you are looking to take your business to the next level.”

Eric Leigh, VP of Mortgage Lending

Guaranteed Rate

Hear about Whetstone Members' Experiences

Clarity, Connection, Momentum

Meet four Whetstone Mastermind members. Hear what it’s like to join a peer group where trust runs deep, perspectives shift, and breakthroughs are the norm.

Avoiding Crucial Mistakes

 “There were a lot of mistakes I was able to fix and a lot of mistakes I would have made that I didn’t because of Allison’s help. All of the different people in Whetstone come from different industries, so it helps me to get a different perspective than what I would get with just my healthcare mind.”

Kellie Northam, Owner

MOMMA, Inc.

Better at Setting Goals

“Now that I’ve spent time working with Deliberate Directions, I’m better at setting goals. and having them be in pieces that I can check off. I’m better able to allocate my time to the things that actually matter in my business and the things that actually earn me money.”

Alex Lundgren, Business Advisor

Tree City Advisors

Mastermind Group Features

Whetstone ✅Other Masterminds ❌
AccountabilityFollow through on your commitments and execute your plans.No real structure or follow-up.
Peer InsightsLearn from experienced business leaders and their proven strategies.Limited perspectives from your internal team.
Growth-Oriented DiscussionsTackle real business challenges and find solutions.Unstructured networking with no real takeaways.
Confidential & Trusted EnvironmentSafe space for honest, confidential conversations and deep problem-solving.Superficial business connections.
Personal & Professional GrowthChallenge yourself and refine your leadership skills.Staying stuck in the same patterns.

Frequently Asked Questions

What if I don’t have time for this?

High-performing leaders make time for strategic thinking. Just a few hours a month in a Whetstone group can save countless hours by helping you avoid costly mistakes and make smarter decisions faster.

Your return on investment includes better decisions, valuable connections, and accountability. These lead to business growth, increased efficiency, and higher profitability.

Even successful leaders like Warren Buffett, Bill Gates, and Elon Musk surround themselves with trusted advisors. You don’t have to navigate everything alone when you can learn from those who have already been where you are.

Whetstone groups operate under strict confidentiality, ensuring a safe and judgment-free space where you can discuss challenges openly and get real solutions from experienced leaders.

The best way to find out is to attend a Visitor Day. There’s no commitment—just an opportunity to experience how a Whetstone group can help you grow.

Who Sharpens Your Thinking?

Sit in on a Whetstone session.