Business Truth Teller
I help business owners face the truth, fix what’s broken, and finally grow with purpose.
I’m Jonathan
…founder of Underpin Consulting, a strategic operations consulting company focused on helping service-based business owners master the foundational disciplines required to run a successful business.
Drawing from my signature “10 Hard Truths of Business Ownership,” I deliver unfiltered insight into what it really takes to build a business that lasts. Whether I’m keynoting a conference, leading a mastermind, or facilitating a hands-on workshop, I blend storytelling and strategy, weaving in lessons learned from the trenches in a style that is direct yet relatable, showcasing my deep understanding of the emotional and operational demands of business ownership.
My sessions are known for their clarity, candor, and impact. I offer real tools — along with inspiration — providing tangible takeaways that audiences can apply to their lives. I leave every audience with renewed confidence and the courage to take meaningful action in their own business.
Reasons to Book Me
Business ownership is hard. Most people don’t talk about that part. But I do. I show up with real talk, real insight, and real support. As someone who’s been in the trenches and stood beside hundreds of entrepreneurs, I know how to speak directly to the heart of business ownership, and help audiences walk away ready to act.
“We all work so hard and sometimes all we need is to have someone that’s in our corner who can give us that little bit of oomph.”
-Jonathan Kaylor
When you book me, you get The Business Truth Teller, ready to stand in your corner and:
- Deliver unfiltered truth with empathy, humor, and heart
- Speak the language of small business, because I live it every day
- Combine strategy with storytelling to make lessons stick
- Create safe, energized space for learning and transformation
- Offer tangible takeaways, not vague inspiration
- Be easy to work with, on-time, professional, and committed to making your event a success
Reviews
Jonathan gave a hell of a keynote talk. It was inspiring, engaging and full of energy and gave me tangible takeaways that I could apply to my life.
—Lila S.
Absolutely I would hire Jonathan – over and over and over again. He did what he said he was going to do, he showed up in a positive manner and easily made the whole day flow naturally.
— Kimberly K.
Stirring. Informative. Insightful. Jonathan gave participants clarity about what to expect from the rest of the conference.
— Jacki G.
Signature Keynotes
Reality Check
In this keynote, Jonathan delivers a much-needed reality check rooted in his 10 Hard Truths of Business Ownership. With a mix of heart, straight talk, and hard-earned wisdom, he dismantles the myths that keep entrepreneurs stuck—like “passion is a business model” or “failure is something to avoid”—and replaces them with practical, actionable truths.
Whether your audience is made up of seasoned founders or first-time solopreneurs, Jonathan meets them where they are, shines a light on what’s really holding them back, and gives them the clarity and tools to move forward with confidence.
This talk is a wake-up call—and a rallying cry. Because once business owners understand the rules of the game, they can finally start winning on their own terms.
Audience Takeaways:
- Learn the 10 truths that separate struggling business owners from sustainable ones
- Reframe failure as a required ingredient for success
- Gain clarity on the difference between activity and progress
- Walk away feeling grounded, capable, and ready to lead with intention
The Customer is Not Always Right
What if everything you thought about customer service was wrong? In this provocative keynote, Jonathan challenges the long-held mantra that “the customer is always right,” not to dismiss the customer, but to reframe how we serve them. The truth is, customers are emotional, not logical. They make decisions based on how they feel, not what we explain.
This talk explores the psychology of customer behavior and the vital importance of emotional connection. Jonathan shows how win/lose dynamics on the front lines lead to burnout and turnover, while businesses that prioritize empathy and perception-based communication drive loyalty, retention, and long-term profit. It’s time to stop trying to win the argument and start building real relationships.
Audience Takeaways:
- Learn how perception shapes the customer experience
- Understand why emotional connection, not information, is the key to retention
- Shift from reactive customer service to relationship-driven growth
- Build a culture where everyone wins: customer, employee, and company
Reviews
I keep coming back to Jonathan’s masterminds because we’re having really driven conversations about what goes on in my head day to day and how I can develop and grow my business.
—Jessica R.
Jonathan helped me create the mindset I need to visualize what’s possible in my business to achieve success!
— Dee T.
Jonathan always delivers! He strikes the perfect balance between actionable insights and just the right amount of humor to keep you fully engaged.
— Paul S.
Workshops
Topics Include:
• Leadership Development
• Effective Communication
• Customer Service Essentials
• Successful Goal Setting
• Team Building
• Change Management
• Public Speaking
Reviews
I highly recommend Jonathan’s workshop. I would attend again anytime!
— Dominika T.
Absolutely Amazing!
— Marty M.
Jonathan is excellent at translating dreams and passion into success for small business owners.
—John B.
Underpin Consulting 