What happens when the business you thought would set you free starts to feel like a prison? In this episode of Independence by Design™, I sit down with Jean Moncreiff, a seasoned entrepreneur turned coach, to unpack the hard lessons he learned scaling businesses, juggling cash flow nightmares, and realizing he was building a job, not independence.
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Jean’s story is packed with insights for owner-operators who feel stuck in the daily grind, questioning if all the hustle is worth it. We dive into his pivotal realization that revenue growth alone doesn’t create freedom and why being intentional with your ownership goals is the key to creating a business—and a life—that serves you.

Jean also shares how he learned to tie together strategy, cash flow, and leadership to escape the operational chaos and focus on building sustainable value. If you’ve ever wondered how to stop being owned by your business and start owning it, this episode is for you.

Jean Moncrieff is an entrepreneur, coach, and advocate for intentional independence. With over 20 years of experience scaling businesses and navigating growth challenges, Jean now helps business owners align their operations with personal and financial goals. As a certified Metronomics coach, he empowers leaders to build sustainable, purpose-driven companies that provide freedom and independence.

Chapters:

• (00:00) Intro - Jean’s path from apartheid to independence as an entrepreneur

• (10:15) Challenges of rapid business expansion, mistakes and complexities in business growth, partner conflicts in business

• (14:00) The turning point: realizing revenue ≠ freedom, building business growth and independence

• (21:00) Building systems for cash flow and value creation, intentional and independent growth, balancing short-term gains with long-term asset building

• (28:00) Complexities of managing a business amid financial pressures and ethical dilemmas, a strategic shift towards improving business structure and leadership, cash flow and ethical dilemmas

• (39:26) Learning from business mistakes and resilience, overcoming setbacks and the importance of persistence, balancing profit and freedom

• (46:15) Advice for owners: how to be intentional about independence, understanding entrepreneurial vision and growth, rethinking entrepreneurial goals and personal intentions, aligning business growth with personal lifestyle desires

• (50:39) Exploring strategic business growth methodologies, adapting new frameworks for rapid business transformation, choosing business methodologies for effective growth, evaluating Metronomics over EOS for strategic success

• (1:02:04) Exploring growth through partnerships, importance of partnerships and collaboration, building purpose-driven companies through meaningful connections, leveraging AI and collaboration for business success, redefining relationships and collaboration in the digital era

• (1:07:13) Decoupling income and strategic business growth, balancing operational roles with financial objectives

• Share with the owner/operators you know!

Ryan Tansom is a seasoned entrepreneur, speaker, and the founder of Independence by Design™, a transformative ownership framework for growth-oriented business owners. After turning around and selling his family business in an eight-figure exit, Ryan spent over a decade dissecting the lessons learned from his journey. His mission is to help other business owners avoid the pitfalls he encountered by providing them with the tools and knowledge to align their business operations with their personal and financial goals.

With a deep understanding of the challenges faced by owner-operators, Ryan developed Independence by Design™ to empower owner-operators to create sustainable cash flow, grow their company’s equity value, and achieve true independence. He has shared his insights on hundreds of stages, including Vistage, EO, and industry associations, and has reached over 500,000 listeners through his podcast.

Ryan is passionate about helping business owners get unstuck from the day-to-day grind and design a business that serves their life, not the other way around.

Resources:

JeanMoncrieff.com

Jean Moncrieff LinkedIn

Twitter: @jeanmoncrieff

Finish Big by Bo Burlingham

Traction by Gino Wickman

Metronomics

Small Giants 2025

Independence by Design™ Workshop: https://ryantansom.com/independence-by-design-workshop

Independence by Design™ Ownership Coaching: Ryan Tansom’s Ownership Accelerator programs and coaching https://ryantansom.com/coaching

Ryan Tansom Website https://ryantansom.com/

Ryan Tansom LinkedIn https://www.linkedin.com/in/ryantansom/

Ryan Tansom Twitter https://twitter.com/RyanTansom

Ryan Tansom YouTube https://www.youtube.com/@ryantansom

Ryan Tansom 30-Minute Ownership Strategy Call https://calendar.app.google/tsKk7z6ohugDchWq8

Sound Bites:

"I thought more revenue would solve my problems, but all it did was create bigger ones." – Jean Moncreiff

"When I realized my business wasn’t worth what I thought, it forced me to rebuild with a new perspective." – Jean Moncrieff

"Revenue is vanity, profit is sanity, but cash flow is freedom." – Jean Moncreiff

"Business isn’t about more hustle; it’s about aligning your business’s operations with your ownership goals." – Ryan Tansom