Anthony Chiaravalloti
About

Who I Am

Entrepreneur. Investor. Systems Thinker.

I’m an operator and strategist focused on building companies, scaling people, and helping founders turn complexity into clarity. My work sits at the intersection of finance, systems, psychology, and execution, where clear structure and disciplined decision-making drive sustainable performance.

I’ve built and led multiple professional service businesses, working closely with founders on growth, capital allocation, operations, and talent. A core part of my work has been partnering with leadership teams in a fractional CFO and finance leadership capacity, helping them design financial and operating systems that support scale. I’m particularly interested in how accountability, incentives, and organizational design shape behavior and outcomes inside growing companies.

Today, I lead Liberty Horizons, a fractional finance and operating partner to founders, where my focus is helping leadership teams build financial clarity, operational discipline, and scalable internal systems. I also lead King Street Media, working alongside founders on growth strategy and execution while applying the same system-first, accountability-driven approach to scaling teams and performance.

I believe scalable companies are not built through constant heroics, but through well-designed systems and people who are empowered to think clearly and act responsibly. I’m especially focused on organizations where thoughtful structure, strong culture, and aligned incentives create long-term enterprise value.

I partner with founders who want clarity, leverage, and long-term freedom.

‍Operator by nature. Strategist by training. Focused on people, systems, and decision-making.

When I left university, I realized something uncomfortable:
Four years of education had taught me everything about theory, and almost nothing about life.

I studied science and finance, yet the moment I stepped into the real world, I saw how disconnected most people, even the most successful ones, were from the systems that actually shape their lives: money, time, health, and decision-making.

At 21, I was working as a financial advisor, helping clients who were surgeons, executives, and professionals far older than me, yet many didn’t know how taxes worked, how credit systems operated, or how to make their money grow. That moment flipped a switch.

I realized the real curriculum of life starts after school ends.
And I’ve been studying, building, and sharing those lessons ever since.

Over the past decade, I’ve built ventures that help entrepreneurs grow, scale, and reclaim freedom through smarter systems in finance, operations, and creativity. My work now revolves around three pillars:

  • Building companies that help entrepreneurs scale.
  • Investing in the next generation of founders.
  • Exploring how technology, psychology, and philosophy shape human progress.


I’m driven by one idea: If we can understand how the world really works, we can build better ones.

Active Ventures

  • King Street Media — A creative growth marketing agency helping founders turn brand vision into revenue. We focus on strategy, creative, and media execution for growth-stage companies ready to scale.
  • Liberty Horizons — A full-stack fractional finance team to growth-stage Canadian businesses. We don't just do your books. We embed ourselves as long-term strategic partners that build your business alongside you, handling everything from bookkeeping to CFO-level strategy.
  • CreatorClub — A private creative community and full-service content creation hub focused on leveraging, helping operators grow their business, audience, and influence through systems and storytelling.
  • What They Did Not Teach You In School — A podcast & content platform born from my curiosity about the lessons life teaches that classrooms don’t. Through conversations with entrepreneurs, academics, and professionals, I explore how people design lives of freedom and purpose by thinking differently about value, time, and mastery.

Companies I Partner with Often

SocialDrop, Foundation Capital, Equivesto, Category Comms, FullPortDEV, Scocco Law, Swift Outbound

My History

My History

2009
TD - Financial Service Representative
Student - York University
Rugby Player - York Lions
2010
Student Mentor - Health Aid Network
2011
2012
2013
Ainova Robotics - Chief Financial Office
2014
IG Welath Management - Consultant | Wealth Manager
CrossWing Inc. - Business Development Manager
2015
2016
The Wise Investor - Host
King Street Media - Managing Partner, Director of Strategy
2017
2018
Veme.ly - Fractional Financial Officer
2019
Liberty Horizons - Managing Partner
Rac N Roll - Chief Financial Officer
2020
Wealthable.ca - Resident Tax Consultant
ONMEN - Chief Financial Officer
2021
2022
CreatorClub - Co-Founder & CEO
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Simon Says - General Manager
2023
Dreamcrust Inc. - Chief Financial Officer
2024
2025