Meet Trent
Trent Trailov
Founder & CEO, Trail CPA
What inspired you to start Trail CPA?
My parents were small business owners, and I grew up in a household that always encouraged entrepreneurship—so it’s been an aspiration for as long as I can remember. Over the course of my career in accounting, I paid attention to what worked and what didn’t, gradually shaping the vision that would become Trail CPA.
What is the core purpose behind Trail CPA?
I want to build a company that transforms the typically unpleasant experience of filing taxes into one that is easy, approachable, and—even enjoyable. At its heart, Trail CPA exists to help business owners feel calm, confident, and supported when navigating financial complexity.
What values guide your leadership and decision-making?
Strategic advice and perspective
Strong communication
Simplifying the complex
Client peace of mind
What’s the most rewarding part of leading Trail CPA?
For me, the greatest reward is seeing our team succeed. While I love helping clients directly, what excites me most is building a culture and a firm where talented people thrive—because that success naturally flows into the value we deliver for clients.
What personal or professional experiences shaped your approach to business?
My professional experience before founding Trail CPA helped build the framework for the business, teaching me lessons on both what to do and what not to do. Knowing I eventually wanted to start my own company, I’ve always made a point to learn from the organizations and leaders around me—those insights shaped the way Trail CPA was built.
What’s your vision for the future of Trail CPA?
I see Trail CPA continuing to grow and improve, powered by the strength of the team we’ve built. In the coming years, my focus will increasingly shift toward business development and sales, ensuring the firm grows in alignment with our values while delivering exceptional client experiences.
What do you enjoy doing outside of work?
Outside of work, I enjoy spending time with my wife and our two daughters (ages 1 and 3), who keep us busy and bring so much joy. My mornings start with fresh coffee, and I enjoy outdoor activities like canoeing, biking, paddleboarding, walking, skiing—and hanging out with Gus, our doodle and best friend (who’s mostly a good boy).
Connect with Trent on LinkedIn or Book a Meeting today.