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James Ashford sold GoProposal to Sage for an eight-figure sum. People hear that and picture a clean line from idea to payday. It took him two decades, several businesses that died along the way, and one moment where he couldn't afford the fee to shut a company down.

He started as a wedding magician, walking straight up to the rowdiest table in the room on purpose. What he learned there became the thing every later business ran on. The failures came too: an agency he loved, gone over a single decision. A marriage under strain. A debt a friend had to cover for him.

Then a mentor asked him one blunt question, and the answer changed how he built everything after.

The part people don't see coming is what the exit actually did to him. The win arrived, and so did something he hadn't planned for. He talks about it more honestly here than most founders ever will, including the redefinition of "wealth" he landed on at the end, which is not the one he set out chasing.

If you're building something you hope to sell, or you already have and it feels stranger than you expected, this one's worth your time.

What Alan and James get into:

• Why he targeted the worst table in the room, every time
• The agency that went under from one bad call, and what it cost him beyond money
• The liquidation he couldn't pay for himself
• A million-pound cheque pinned to a bedroom ceiling years before it meant anything
• The mentor question that rearranged his whole approach
• How he picked who would buy his company long before they knew they would
• The second Range Rover he ordered and sent straight back
• The thing nobody warns you about on the other side of an exit
• The definition of "true wealth" he arrived at, and how late it came

Connect with James

• Website: https://jamesashford.com
• LinkedIn: https://www.linkedin.com/in/jamesashford/
• Instagram: https://www.instagram.com/thejamesashford
• TikTok: https://www.tiktok.com/@fireproofjames

James's book

• Selling to Serve

Other Book Recommendations:

• Building a StoryBrand by Donald Miller
• The E-Myth Revisited by Michael Gerber
• The Psychology of Money by Morgan Housel
• Rich Dad, Poor Dad by Robert Kiyosaki
• The Richest Man in Babylon by George S. Clason
• Tony Robbins' Money: Master the Game

This podcast is produced by Tribunista

Sponsored by Capital Asset Management

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Nick Bradley has sat on the other side of the table for more than 50 acquisitions and 27 exits. He knows exactly how private equity firms assess a business, where founders give away their leverage, and why so many walk away from a life-changing deal with far less than they should have.

But this conversation is not really about deal mechanics. It is about the journey that got him there. From running a small gym in Adelaide to launching magazines in Sydney, to flying between London and New York every week for a job that was quietly costing him everything. It took a sudden loss, a stress injury he never saw coming, and an unexpected reunion to make him question the entire game he had spent a decade winning.

In this episode, Nick shares the framework he now uses to help founders build genuinely valuable businesses, the difference between the companies buyers fight over and the ones they pick apart, and the identity shift that has to happen before any exit is worth doing. He also opens up about the moment he put a resignation letter on the table, and how his definition of success looks nothing like it did ten years ago.

A candid conversation about ambition, reinvention, and what it actually means to build something worth selling.

This podcast is produced by Tribunista

Sponsored by Capital Asset Management

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Anton arrived in the UK with £500 in his pocket. Years later, he founded WealthOS. He recently sold it to one of the world's largest banks.

In this episode, Alan sits down with the founder of WealthOS to talk through what the journey from arrival to acquisition actually looked like.

We hear about the door-knocking days in suburban Surrey, and the decision to leave a senior corporate role with two children in private school and a mortgage to cover. He shares the framework he used to pick a co-founder, and why the person who scored highest was not who anyone expected.

We get into the angel rounds, the strategic investment from Barclays, and the Liz Truss-era fundraising window that nearly ended the company.

There is the November when the bank account was down to four figures and payroll was three weeks away. The conversation he had with his wife about pulling the kids out of school. And the call from JP Morgan that came when an exit was not on his mind.

He also shares the principle his former chair gave him about how good businesses get acquired, and his answer to what wealth actually means after you have built and sold one.

Links:

Wealth OS: https://www.wealthos.cloud/

Anton's LinkedIn: https://www.linkedin.com/in/antonpadmasiri/

Books:

"Dreams From My Father" by Barack Obama - https://amzn.eu/d/074kFId1

"Range" by David Epstein - https://amzn.eu/d/0iBX3kyj

"Build" by Tony Fadell - https://amzn.eu/d/06ueeONi

Podcasts:

"Invest Like The Best" by Patrick O'Shaughnessy - https://pod.link/1154105909

This podcast is produced by Tribunista

Sponsored by Capital Asset Management