Jonathan Kaylor | SpeakerHub

Personal Details

Bio

Jonathan Kaylor is the founder of The Fractional Handyman, a growth consulting company focused on helping small and micro business owners turn passion into profit. With over two decades of experience leading high impact teams and problem-solving for businesses across different industries, Jonathan has seen, and fixed, just about everything.

Drawing from his “10 Hard Truths of Business Ownership,” Jonathan delivers unfiltered insight into what it really takes to build a sustainable business. Whether he's keynoting a conference, leading a mastermind, or facilitating a breakout session, Jonathan blends storytelling and strategy, weaving in lessons learned from the trenches in a style that is direct yet relatable, showcasing his deep understanding of the emotional and operational demands of business ownership.

Jonathan is based in Vancouver, WA and Portland, OR metro, so yes, he’s always armed with a good cup of coffee. And when he’s not untangling business challenges, you might find him cooking up something in the kitchen, strumming an acoustic guitar, or enjoying a solid craft beer—because work-life balance matters.

Current position (1)

Founder

Fractional Handyman

Degrees (1)

Communications

University of Dayton

1994 to 1998

Presentations

Presentations (1)

Reality Check: The Hard Truths Every Business Owner Needs to Hear

Starting a business is exhilarating. You’re driven by passion, fueled by talent, and ready to make your mark. But somewhere along the line you realize being good at your craft is not the same as being good at business.

That’s where the Reality Check begins.

In this talk, I uncover the 10 Hard Truths of Business Ownership and walk through how to become a better business owner, so they don't have to be learned the hard way. I explore topics such as the importance of building your business beyond just your passion, how to lean into failure, and developing the mindset you need to sustain a successful business.

But this talk isn’t about discouragement. It’s about calling things what they are and then showing you what to do about it. You'll leave this session with practical tools, a stronger mindset, and the clarity to approach the rest of the conference—and your business—with intention, openness, and a renewed sense of control.