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#107 To Win You Must Suffer.

BigDeal

Dec 15, 2025

20 min

Description

Most people think success comes from talent, timing, or luck. The brutal truth? It comes from suffering. After building multiple seven and eight-figure businesses and investing in hundreds of companies, I've learned the one thing nobody wants to tell you: to win, you must be willing to endure more pain than everyone else. This isn't about motivation or manifestation — it's about the cold, hard reality of what it actually takes to build the life you want in 2025 and beyond.

In this raw, unfiltered episode, I break down the four brutal truths that will either make or break your success: why four-hour work weeks are a myth (the data shows 85-90% of businesses require daily founder involvement), why everyone is trying harder than you think they are (and hiding it), why there's more competition than you want to admit (305 million startups launched globally last year alone), and why most people will never communicate honestly. I reveal the six types of people you'll face as a leader — from the reactive responder to the strategic warrior — and why only one of them actually wins. You'll learn about effort concealment, survivorship bias, and why 80% of people think they're above average (spoiler: they're not).

But this isn't just about what's broken — it's about what actually works. I expose why the passive income dream applies to less than 1% of the population, why 95% of Shopify stores never make a single sale, and why comparing your reality to someone else's highlight reel is killing your progress. If you've ever felt like you're behind, or wondered why success seems easier for everyone else, or if you're ready to stop believing the lies and start doing the hard work that actually matters, this episode will change how you think about winning forever.

I say it all the time: building real wealth doesn’t require a flashy startup — it just takes one boring, cash-flowing business. Join me at Main Street Millionaire Live to get my exact playbook for finding, buying, and scaling a business. Stop wondering how ownership could change your life, and come find out: https://contrarianthinking.biz/MSML26_BDYT

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00:00:00 Introduction
00:00:54 To Win You Must Suffer
00:01:36 The Six Types of People You'll Face as a Leader
00:04:25 Becoming the Strategic Leader
00:06:32 Everybody Is Trying Harder Than You Think
00:08:12 The Highlight Reel Deception
00:10:30 More Competition Than You Want to Admit
00:13:09 The Startup Gold Rush: The Math Behind Competition
00:14:18 Four Hour Work Weeks Do Not Work
00:16:21 The Contrarian Boardroom Solution
00:17:28 Stop Comparing Your Worst to Others' Best

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