15 years in bookkeeping.
Every client loved me for the first 6 months. By year two? At each other's throats.


I ran a fractional bookkeeping business. In the beginning? I was great. New clients, 
new systems, new problems. But once the novelty wore off—same reconciliations, 
same reports, same emails asking for the same missing documents.
I thought the problem was the clients. The work. Me.
Then I got diagnosed with ADHD.
Turns out my brain runs on uniqueness. I need to feel like what I'm doing is special, 
different, mine. Repetition kills that. So I stopped fighting my wiring and started 
building around it.
Now I build AI tools that solve real problems for real businesses—starting with the 
industry I know cold.
First up: OnboardLy. It kills the document chaos that happens before bookkeepers 
can even start their real work. Because the worst part of a bookkeeper's job isn't the 
bookkeeping—it's hunting down missing bank statements at 11pm.
I work in 10-week sprints. Build, market, launch, rotate. It's the only way my brain lets 
me finish anything.
My white whale? The search tool Ezra Klein said newspapers need. Ask a question, 
get a syllabus—not a list of links, but a structured path through the archives with every 
source at your fingertips. I'm the one building it.
I'm documenting the whole journey here. Wins, failures, everything in between.
Fractional bookkeeper drowning in client onboarding? Let's talk.
Building software for an industry you've never worked in? I have thoughts.

Tim O'Rourke

The McFadden Group

~ Focused on developing emotionally intelligent individuals by aligning goals with core values, to drive their career development.
~ Team career coaching directed at evaluating dynamics, clarifying roles, and integrating core organizational values to align strategic goals, and build resilience within their organizations.

Founder & Career Coach

Fanshawe Toronto@ILAC

~ Developing and Delivering course plans and programs from Fanshawe’s course outlines  
~ Undergrad & Post-Graduate Courses include - Leadership, Ethics & Diversity, Food & Beverage Operations, Tourism & Hospitality Introduction and Innovation, Technology in Hospitality, Ethics in Hospitality, Sales & Customer Relations, Food & Beverage Service Management, Personal Wellness, Career Development.

Professor - School of Hospitality & Tourism

RL101

Restaurant Leadership 101 [RL101], a Restaurant Leadership Training program focused on Emotional Intelligence and Soft Skills for chefs and front of house managers.

Restaurant Leadership 101 Program - Co-Founder, Co-Creator, Instructor

Centennial College

Course content included 
- Leadership Behaviours & Traits, Knowing thyself, Values of Employees, Communication, Vision, Values & Culture, Contemporary Issues, Leading Teams, Motivation/Empowering Trust, Leading through Change, Diversity/Inclusion/Equity

Professor - School of Hospitality, Tourism & Culinary Arts

Executive Table Group

Hydra Estiatorio 

Relationship ended due to having to move to Ontario.

General Manager

Piva Modern Italian

General Manager & Wine Director

Canucks Sports & Entertainment (CSE)

Restaurant Manager & Sommelier

Hy's of Canada

Restaurant Manager & Wine Director

I’ve spent 25 years in hospitality, from the floor to senior leadership, including director and sommelier roles, and one truth has always held up: success comes down to people.

That belief is what drives my work today. When I returned home to Burlington, Ontario in 2022, I founded The McFadden Group to help both individuals and teams strengthen emotional intelligence, align goals with values, and create environments where people can genuinely thrive.

With individuals, I take a career coaching approach that blends emotional intelligence, self-awareness, and practical strategy. Together, we clarify what matters most, reconnect with personal values, and design a path forward that feels both meaningful and sustainable, whether that means rediscovering passion, growing in leadership, or navigating change with confidence.

With teams, I focus on building connection, trust, and accountability, helping people understand each other’s strengths, communicate more openly, and work together with purpose. It’s about turning shared goals into real results while creating a culture that feels authentic and alive.

At the core of it all is a belief I live by: “To truly be happy, one must achieve a better version of themselves to be better for others.”

That’s been my journey, and it’s the one I now help others take, one person, one team, and one honest conversation at a time.

taplio

The Battle

Tim O'Rourke

Christopher McFadden

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