He Built a Million-Dollar Business After Multiple Failures | How He Designed a Life of Freedom

Video Description

[Wealth on Your Terms Podcast with Tobi Adekeye] Epsiode with Tobi Oluwole. You don’t need to hustle 24/7 to build wealth, you just need the right blueprint. What if freedom wasn’t something you waited 30 years to earn, but something you could design now, on your terms? In this episode, I spoke with Tobi Oluwole — an entrepreneur who retired from corporate at 28 From 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. We cover: - How he used storytelling and LinkedIn to generate 300M+ impressions and built revenue - A few insights into what he teaches business owners that has helped founders collectively earn over $20M+ - His decision-making process before quitting his 6-figure tech job - Why he always has business partners and the mindset behind not owing 100% of something great - How to design a lifestyle business instead of chasing someone else’s success ------------------------- 🎙️ About Wealth on Your Terms Wealth 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 by Tobi Adekeye. 📧 For partnerships and business inquiries: [email protected] 📲 Follow us on Instagram: @wealthonyourtermshub Subscribe & tap the 🔔 so you don't miss the next episode. To allow us post more episodes, - Hit the like button to support this podcast and - Write a review and Rate us 5-stars on Spotify and Apple Podcasts 🔗 Listen on Your Favorite Platform - Spotify: https://open.spotify.com/show/1XfWOhFXOVgqurc3ubL6Ed?si=120a11990ec140c9 - Apple Podcasts: https://podcasts.apple.com/ca/podcast/wealth-on-your-terms/id1826415199 - Watch more episodes: https://www.youtube.com/playlist?list=PLiXreb5FVE9xxyOQ119CArRdWpRJf31vw ---------------------- 🏡For real estate inquires, I'm Tobi Adekeye. I'm a licensed realtor under On The Block Realty, Brokerage – Vaughan, Ontario - Book a call: https://calendly.com/tobiadekeye01/tobi-adekeye-real-estate-discovery-call?month=2025-07&fbclid=PAZXh0bgNhZW0CMTEAAae78aNVlFj9ctqVCTHfwu4bLfxTbSIOzAdCvFEOO-0deyxstAQj47f8Mn83jA_aem_x3KfybQQmrsC30wc7wpgBg - Follow my real estate page: @tobi.realestate ------------------------- 📲 Connect With Tobi Oluwole - LinkedIn: https://www.linkedin.com/in/thetobioluwole/ - https://www.tobioluwole.com - Attend Tobi's Re-create Summit 🎟️, A Private Gathering For Entrepreneurs Building Life On Their Terms: https://lu.ma/recreate2025?tk=Zcy3rG ✨ Connect with me, Tobi: 📷 Instagram: @tobi.adekeye 🎥 Tiktok: @tobiadekeye_ 👩🏾‍💻 LinkedIn: https://www.linkedin.com/in/tobiadekeye/ 🗞️ Newsletter: https://tobiderin.substack.com ------------------------- 📌 Timestamps 0:00 – 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 age 14:04 – “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 & 3 questions that has helped him close over $2 million in revenue 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 #wealthonyourterms Disclaimer: The information shared in this episode is for educational and informational purposes only and does not constitute financial or legal advice. Please do your own research or consult with a licensed professional before making any investment or financial decisions.