SEASON 2 Ep. 20 - James Ashford on Richard Branson, Necker Island, Gary Vee & an 8 Figure Business Exit
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In this episode of the Alchemy podcast , I sit down with entrepreneur and investor James Ashford, whose incredible business journey includes building and selling a SaaS company from zero investment to a life-changing 8-figure exit.But behind the headline numbers was a complex and s…
#89 The 20-Year Overnight Success: Failed Businesses, Crippling Debt, and Building GoProposal Into an Eight-Figure Exit
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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…
1.30 DramaWave - Cheerleader and The Beast
Most modern retellings of fairy tales stay safe — this one flips the script with a dark, revenge-fueled twist on Beauty and the Beast, blending horror, drama, and deep character transformations. Megan unpacks how a high school rivalry turns into a story of shattered identities, scars both seen and …
E370 | James Ashford, 8-Figure Founder: The Person You’re Protecting Is Destroying Your Business
In this episode, James shares his challenging beliefs about sales (selling is service, not commission-driven), hiring (fire high performers who are dickheads), business problems (everything is connected—you might think you have a sales problem when it's really a marketing problem), and alignment (y…
Roadway – The Podcast: Episode 17 – Brigade, AI and the Future of Road Safety
The End of Reactive Vehicle Safety: The Role of AI
In this episode of Roadway – The Podcast, Richard Smith is joined by Peter Squire and James Ashford from Brigade Electronics to explore how artificial intelligence is transforming vehicle safety and helping operators move from reacting to incidents…
The Brutal Reality Of Building A Business To Sell - James Ashford
How to sell your business: James Ashford built GoProposal from a WordPress plugin and exited to Sage. This is the full story.
For founders, agency owners and accountants who want a business that runs, grows and sells without them.
James Ashford turned a pricing problem in one accountancy firm into …
Building Software, Scaling Fast and Selling Big: James Ashford’s Business Journey | Episode 67
James Ashford always wanted to be an entrepreneur, but the journey wasn’t a straight line.
After trying different businesses, taking on different jobs and learning from other entrepreneurs, James eventually found his way into the accounting industry. He built a piece of software, bootstrapped the …
James Ashford Part 2: Sold My Business. Then Money Became the Problem.
What happens when the business exit you worked towards finally happens and the money creates a completely new set of problems?In Part 2, James Ashford gives Adam Carolan an unusually candid account of financial planning from the client’s side. Before building GoProposal, James describes himself as …
Xero's Epic Fail Week: Influencers, Micro Accounts & Broken Features | Ask the Accountant #201
In a sudden storm of controversy, Xero has managed to upset its partner community with a series of major blunders. When a paid influencer post suggested replacing accountants with Xero and AI, the industry erupted. This was compounded by the launch of a controversial £120 "micro accounts" filing se…
How to Turn Business Mistakes Into Valuable Lessons - James Ashford
Originally aired: April 2025
Episode Number: 231
Business failures can teach you some of the most valuable lessons in entrepreneurship, forcing you to reflect, adapt, and rethink your approach.
In this episode highlight of North Star Conversations with Will Polston, entrepreneur, investor, bests…
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