April 27, 2026

Mistakes Were Made

1 hour 8 minutes

Even financially independent people have lost fortunes to bad investments, high-fee funds, and speculation. Brad Barrett, Alan Donegan, and Katie Donegan lay bare their most expensive mistakes—from Alan's 90% dot-com crash loss to Katie's near-£1 million fee trap to Brad's decade-long real estate nightmare—proving that catastrophic errors don't prevent you from reaching FI if you learn the right lessons.

Key Topics Discussed

[00:00:00] Introduction: Why Share Mistakes?

Brad introduces the episode concept, explaining why sharing financial and life mistakes can help others avoid similar pitfalls on their FI journey.

[00:03:30] Alan's Dot-Com Bubble Disaster

Alan shares how he lost 90% of his £7,000 life savings investing in high-tech managed growth stocks right before the dot-com crash, and how this scared him away from stock market investing for 13 years.

[00:08:45] Brad's Early Investment Mistakes

Brad discusses investing in WorldCom and other 'top picks' that went bankrupt, plus getting sold a mutual fund with horrible loads, highlighting that there's no secret investment knowledge reserved for the wealthy.

[00:13:20] Katie's High-Fee Fund Trap

Katie reveals how a financial advisor convinced her to invest in actively managed funds with 2.71% ongoing fees plus 3% entry charges, a mistake that would have cost her and Alan £1 million if they hadn't discovered index investing.

[00:18:50] Brad's Real Estate Speculation Nightmare

Brad shares his biggest mistake: speculating on golf course community properties with interest-only loans right before the 2008 crash, causing over a decade of stress and significant financial loss.

[00:28:15] Alan's Career Mistakes: The Book Incident

Alan reveals how he wrote a book called 'How Not to Run a Business' about his boss on the company laptop, got fired, and learned about speaking truth to power and the importance of FI for workplace freedom.

[00:32:40] Katie's Confidence and Comparison Struggles

Katie discusses how her fixed mindset and comparison with others held her back from pursuing opportunities like netball and football, and how building confidence is as important as building net worth.

[00:42:30] The Power of Saying No and Setting Boundaries

The trio discusses the difficulty of being direct and honest, the importance of saying no, and how people-pleasing can create more problems than it solves.

[00:48:20] Business Mistakes: Email Lists and Sales Fear

Alan shares his regret about never building an email list for his successful business and letting fear of rejection prevent him from scaling, emphasizing the importance of owning your platform.

[00:54:10] Salary Negotiation and Final Thoughts

Brad discusses not negotiating his salary when changing jobs, the hosts wrap up with reflections on learning from mistakes, and encourage listeners to share their own mistakes in the community.

Notable Quotes

Brad Barrett: "You can make mistakes and you can make catastrophic mistakes, and you can pick yourself back up and you can move on with your life. You're stronger and you're wiser."

Alan Donegan: "Your success in life is directly related to how many mistakes you can make as quickly as possible and learn from them."

Alan Donegan: "Spend as much time building your confidence as you do your net worth, because it is so powerful in everything you do going forwards."

Katie Donegan: "To rinse the value out of the mistakes, it's a lot more valuable if we share them. I would love you to get the value out of my mistake because I've already paid the price."

Brad Barrett: "There's no secret. There's virtually no genius. Don't get caught up in wild speculative behavior."

Key Takeaways

Invest in low-cost index funds like VTI instead of actively managed funds or individual stocks to avoid high fees and poor performance

Build an email list from day one if you're starting a business—don't rely solely on social media platforms you don't control

Always negotiate your salary when changing jobs or getting promoted

Work on building your confidence alongside your net worth—practice saying no, setting boundaries, and being direct in difficult conversations

Learn from others' mistakes rather than making them yourself

Avoid speculation in real estate, stocks, or any investment—stick to boring, proven strategies like index fund investing for long-term wealth building

Make mistakes quickly and learn from them—failure is part of the path to success as long as you extract the lessons and keep moving forward

Resources and Links Mentioned

50 Ways to Say No by Elizabeth Andrews

ChooseFI Episode 454 - Salary Negotiation with Financial Mechanic

ChooseFI Episode 147 - Salary Negotiation with Tori Dunlap

Rebel Finance School

JL Collins and The Stock Series

Vanguard Total Stock Market ETF (VTI)

ChooseFI Community Platform

Support the Show
We work hard to keep ChooseFI ad-free for a clean listening experience. The easiest way to support us is to use our Top Recommended Cards page when signing up for your next travel rewards credit card.

...more

View all episodes

By ChooseFI

4.8

50485,048 ratings