Bankrupt to “Cowboy Closer”: The Truth About Making Money Online — No Bollocks with Matt Haycox

Most people don’t fail because they’re “lazy”. They fail because they keep waiting to feel ready.

In this episode, Matt Haycox sits down with Connor Western, better known online as The Cowboy Closer, to talk about the messy middle: financial mistakes, bankruptcy, rebuilding from zero, and what it really takes to make money online when motivation disappears.

Connor breaks down how he tried to escape the rat race by starting five businesses at once, what that taught him about option paralysis, and why he now believes the real game isn’t a “side hustle”, it’s mindset, psychology, and environment design.

What you’ll learn in this episode

Why Connor says he had to learn financial literacy the hard way.
The bankruptcy story, and the risky “0% balance transfer” spiral that helped trigger it.
“Option paralysis”: why starting five businesses was his way of forcing momentum.
The truth about remote sales (and why “getting the job” isn’t the hard part).
How “Cowboy Closers” became a brand, and why Connor’s marketing is built to polarise.
Why Connor sees content as the long game: “film everything” and let the business catch up.
What he’d do differently now (spoiler: one thing, not five).

Timestamps:

0:00 — Intro: Meet “The Cowboy Closer”
0:45 — Bali, Dubai, UK: designing your environment
10:13 — Environment vs discipline vs motivation (what actually works)
17:02 — Mental health: depression, suicide, and the cost of “pushing through”
24:57 — Online coaching + remote sales: why Connor’s model wins
28:41 — Ambition, ego, and what success really means
33:37 — Mentors, influence, and the personal development industry
40:57 — Connor’s business model: mindset-first sales training
44:59 — The moustache, final truths & where to find Connor

Follow Connor Western:
Instagram: https://www.instagram.com/connorwestern_/
YouTube: https://www.youtube.com/channel/UC1aRUmUvyPfWGidVeFpaIlg

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Connect with Matt Haycox, No BS Business Podcast Host & 8-Figure Entrepreneur.

I’m Matt Haycox, entrepreneur, investor, and your straight-talking guide to building a business that actually works. I’ve raised over £750M, built (and rebuilt) 8-figure companies, and learned the hard way what it really takes to win.

On No Bollocks with Matt Haycox, I cut through the bollocks to bring you raw conversations with 7–8 figure founders, investors, and experts who’ve been there, done it, and got the scars to prove it. No hype, no theory, just actionable strategies you can use today to start, grow, and scale your business.

Whether you’re stuck in your 9–5, building your side hustle, or trying to hit your first £100k month, this is your go-to podcast for entrepreneur tips, startup growth strategies, raising capital, building a personal brand, and avoiding the costly mistakes most founders make.

📩 Get Matt’s free business newsletter for weekly strategies, mindset shifts, and behind-the-scenes lessons → https://nobollockswithmatthaycox.beehiiv.com/subscribe

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