What if being “delusional” is the only reason he made it?
In this raw and revealing episode, Tobi Oluwole shares how he built his life with intention, storytelling, and a level of delusion he believes every successful immigrant needs. From moving across continents to quitting Shopify the day after buying a house, to generating over 300 million impressions on LinkedIn, Tobi explains the mindset, strategy and frameworks that transformed his life.
We talk about designing your future through writing your own eulogy, applying delusion where the odds actually work, why immigrant founders succeed at higher rates, and how storytelling became the engine behind every opportunity in his career.
In this conversation, you’ll learn:
Why Tobi believes delusion is a strategy, not a flaw
How writing his own eulogy changed every decision he made
The truth about immigrant pressure, sacrifice, and ambition
How storytelling on LinkedIn built a global business
Why fear of judgment stops 99% of people from succeeding
How to design a life you can actually live, not escape from
If you’re an immigrant, an entrepreneur, or someone trying to build a life on your own terms, this episode will shift your perspective forever.
Subscribe for more conversations that challenge how you think and inspire how you live.
Chapters
00:00:00 — The Anomaly in the Room
00:01:06 — Growing Up on Three Continents
00:02:19 — The Football Dream Meets Reality
00:03:54 — Accepting Limitations Without Losing Ambition
00:05:35 — Why Quitting Can Be a Skill
00:07:41 — The Power of Delusion (Used Correctly)
00:09:27 — The Strategy Behind His Delusion
00:11:00 — Raised by Builders: The Family Influence
00:13:00 — Laid Off, Broke, and Rebuilding
00:14:42 — Why Shopify Became His MBA
00:16:36 — Buying a House, Then Quitting the Next Day
00:18:38 — Writing a Eulogy to Design His Life
00:20:34 — The Identity That Drives Everything
00:22:30 — Living in Your Own Design, Not Society’s
00:23:40 — Does He Believe in Manifestation?
00:25:10 — Being a Seed Sower, Not a People Pleaser
00:27:14 — Harvesting Without Apology
00:28:40 — How Shopify Taught Him the Storytelling Framework
00:30:03 — The LinkedIn Post That Changed Everything
00:31:39 — Becoming a Magnet, Not a Hunter
00:33:00 — The Real Reason People Don’t Post Online
00:35:45 — Pushing Past Judgment and Execution Barriers
00:37:45 — Why Personal Branding Feels So Hard
00:39:26 — Why LinkedIn Is a Cheat Code
00:41:09 — Why He’ll Never Be a ‘Content Creator’
00:43:26 — One LinkedIn Lead vs Twenty Social Leads
00:45:32 — Building Businesses from Attention Alone
00:47:08 — The Toronto Conference: A New Chapter
00:49:38 — Immigration Is Not the Problem You Think It Is
00:52:50 — What No One Says About Immigrant Sacrifice
00:55:07 — Solving the Problem Instead of Complaining
00:57:48 — Need-trepreneurs vs Want-trepreneurs
01:00:47 — What He’d Tell His Younger Self
01:02:55 — Gratitude, Grounding, and the Long Game
