Building a Million-Dollar Business After Multiple Failures | How to Design Your Life | Build a Business you won't hate

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In this episode, I spoke with Tobi Oluwole — an entrepreneur who retired from corporate at 28From getting rejected 6 times by Shopify to building a 7-figure business helping others do the same, Tobi now works 3 days a week, travels the world, and takes summers off. He’s proof that freedom isn’t just a dream, it’s a design problem.Whether you’re stuck in a 9–5 or building a business, this episode will stretch your definition of freedom. Tobi breaks down how to build a business that funds your lifestyle, not one that becomes your new 9–5. He shares frameworks, mindset shifts, and numbers to know what's possible.📌 Timestamps0:00 – Intro 1:31 – The lesson that blew up Tobi’s life and his LinkedIn 8:07 – What shaped Tobi’s risk tolerance from a young age14:04 – “I was the worst employee” – and why Tobi had to be an entrepreneur 19:38 – Knowing when to quit vs. when to keep pushing 24:13 – Is Entrepreneurship About Luck or Strategy? 24:50 – Business #13: Why this one actually worked after many failed attempts 35:21 – The wildest income a founder has made in his accelerator 37:52 – Why some people never make it: the #1 thing holding you back 40:38 – Investing in startups and boring businesses – a wealth strategy 43:32 – The power behind business partnerships and co-founders 47:38 – Lessons from six-figure+ monthly earners 50:29 – Modern wealth creation: raising the ceiling for entrepreneurs 55:26 – Ideas and naysayers: pushing beyond doubt and opinions 58:51 – How to build a business that funds your dream lifestyle (aka how to design your life) 1:05:15 – Redefining success and the true feeling of freedom 1:10:50 – If you’re stuck right now… listen to this part -------------------------🎙️ About Wealth on Your TermsWealth on Your Terms is a podcast about building wealth, freedom, and impact — in ways that actually work for your life. Through unfiltered conversations with builders, unconventional thinkers and investors, we break down the real playbooks behind modern wealth building and freedom living. Hosted