In this episode, we dive into Never Enough by Andrew Wilkinson — a brutally honest memoir about the highs and lows of entrepreneurial success, the dark side of ambition, and the endless chase for more. Wilkinson, co-founder of Tiny and one of Canada’s most successful entrepreneurs, takes listener...
In this episode, we dive into Never Enough by Andrew Wilkinson — a brutally honest memoir about the highs and lows of entrepreneurial success, the dark side of ambition, and the endless chase for more. Wilkinson, co-founder of Tiny and one of Canada’s most successful entrepreneurs, takes listeners behind the curtain of building wealth and influence, exposing how the pursuit of money and status can leave even the most outwardly “successful” people feeling empty.
Never Enough is not just a business memoir; it’s a cautionary tale. Wilkinson reflects on his rise from scrappy beginnings to becoming a multimillionaire investor, all while struggling with dissatisfaction, anxiety, and the constant feeling that no achievement was ever truly enough. This book challenges the cultural obsession with growth, success, and wealth, while asking the deeper question: what really makes a good life?
✅ What you’ll learn in this summary:
- How Andrew Wilkinson built his businesses and investment empire
- The hidden costs of relentless ambition and entrepreneurial hustle
- Why chasing money and status rarely leads to true fulfilment
- Insights into redefining success beyond wealth and work
- How to balance ambition with wellbeing, purpose, and happiness
Why this book matters: In a world that glorifies hustle culture and growth at all costs, Never Enough offers a refreshing and vulnerable perspective. It’s a must-read for entrepreneurs, leaders, and professionals who want success without sacrificing their health, relationships, and peace of mind.
Who should listen:
- Entrepreneurs and business leaders chasing growth and ambition
- Professionals struggling with burnout, stress, or “never enough” thinking
- Investors and creatives seeking balance between money and meaning
- Fans of candid entrepreneurial memoirs and real-life lessons
- Anyone questioning the trade-offs of success and what it means to live well
✅ Key Takeaways:
- Ambition has a shadow side — chasing more can leave you feeling less.
- Money isn’t the answer — fulfilment comes from purpose and relationships.
- Success needs balance — health and happiness matter as much as wealth.
- Culture glorifies growth — but not all growth is good growth.
- Redefine “enough” — true success is finding peace with where you are.
By the end of this episode, you’ll understand Wilkinson’s hard-won lessons about success, money, and meaning — and how you can avoid falling into the “never enough” trap yourself.
Keywords: Never Enough summary, Andrew Wilkinson book, entrepreneur memoir, business book podcast, success and fulfilment, money and ambition, hustle culture critique, entrepreneurial burnout, redefining success, life beyond wealth
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