logo
episode-header-image
Aug 18
28m 3s

Episode 780: The Ten Best and Worst Deci...

JAMES WEDMORE
About this episode

What is a "bad decision" if not a lesson in disguise? And what do you do once you've learned that lesson? Today, I'm sharing the ten worst decisions I've made across my 18 years in business and life. From costly business partnerships and legal missteps to personal regrets and missed financial opportunities, I'm pulling back the curtain on my biggest screw-ups so you don't have to make the same ones. 

This isn't a conversation about regret; it's about reflection. Tune in now and to let us know which of these you can relate to the most, and make sure to tune in next week for Part Two, where I’ll be revealing the best decisions I’ve ever made! 

If you haven’t yet signed up for my free weekly newsletter for online experts, The Digital CEO Weekly, you can sign up now and get it delivered straight to your inbox every Monday morning at www.jameswedmore.com/newsletter

Hey there, Digital CEO!

If you’re loving this episode and you know this is your year to finally build, launch, or scale your digital business the right way — then I’ve got something for you.

Business By Design, my signature program that gives you everything you need to design a leveraged, profitable digital product business, only opens once a year… If you want to be the FIRST notified when doors are open, you can get on the waitlist for BBD 2026 right now. That way, you’ll be the first to know when we open enrollment again (and trust me, you do not want to miss it!).

Head to www.businessbydesign.net/ and join the waitlist today!

Before you go, snap a screenshot of the episode playing on your device, post it to your Instagram Stories and tag us, @jameswedmore and @jeunejenni. 

In this episode you’ll hear:

  • Why doing it yourself is sometimes the best option, and how I learned this lesson the hard way through multiple business partnerships

  • The crucial importance of getting every agreement in writing

  • Why you should invest in yourself sooner and the single decision that changed my business trajectory after years of struggling 

  • How the habit of investing, no matter how small the amount, is more critical to financial success than how much money you make

  • What I learned after selling Bitcoin and passing on real estate opportunities out of fear

  • Why the desire to "improve" something that's already working can lead to costly mistakes and how I learned this lesson the hard way 

  • The importance of keeping your guard up and not trusting easily 

  • Why a bad decision is only a true mistake if you don't learn from it and apply the lesson to future choices

For full show notes and links, visit: https://www.mindyourbusinesspodcast.com/blog/780 

Up next
Oct 6
Episode 788: The Most Common Traits of Today’s High-Performers and The Most Pesky Subconscious Blocks Preventing Your Success with Brad Bizjack: Part One
Why does it feel like only a few entrepreneurs are able to continually produce quantum leaps of success in their business, while most struggle year after year, despite how hard they work or how many strategies they try? Today, Jenni and I are joined by our good friend, Success an ... Show More
1h 5m
Sep 29
Episode 787: The Most Powerful Strategies for Un-Bottlenecking Yourself
Are you feeling bottled up in your own business? If it seems like the very success you've achieved is now holding you back from growth, then this episode on “un-bottlenecking” yourself is just what you’ve been looking for! Today, we cut through the noise to expose the real reason ... Show More
51m 34s
Sep 22
Episode 786: 11 Non-Business Habits That Actually Help You Grow Your Business
What are the habits of a truly successful entrepreneur? Is it all about the grind, working 24/7, and constant hustle? The truth is, it's not. Today, Jenni and I share some of the most surprising and impactful non-business habits that have been crucial to our success and happiness ... Show More
1h 2m
Recommended Episodes
Jun 2025
MicroVee: The Worst Business Advice I Ever Got — And How It Made Me Win or
Today’s MicroVee is a powerful reminder that bad advice can lead to great outcomes — if you trust your gut.I sat down with Massimo Marioni from Fortune and shared one of the worst pieces of business advice I’ve ever been given… and how ignoring it helped me build a massive retail ... Show More
7m 31s
Jan 2025
SPI 853: Ranking the BEST and WORST Business Ideas for Beginners (2025)
#853 Focusing on the wrong business idea might slow your growth if you're just starting out. So what are the top opportunities to prioritize, and which ones should you save for later in your journey? Listen in on today's session because I'm ranking the best and worst monetization ... Show More
55m 46s
Sep 16
I Wasted $20,000 (Here’s the Lesson I Still Use Today)
Your Fear Of Wasting Time And Money In Course Creation Is Costing You (+ A Hack To Fix It Fast) If you’ve been sitting on a course idea for months (even years), telling yourself you’ll do it “someday,” chances are fear is in the driver’s seat. Maybe you’re worried it will take to ... Show More
24m 55s
Sep 17
914: The 5 Business Mistakes I Learned the Hard Way (So You Don’t Have To)
When I think about those first few years as an entrepreneur, I see a woman who was so full of fire and determination, but honestly had no idea what she was walking into. And I love her for that! Now, after years of growth, evolution, and yes, plenty of beautiful failures, I can s ... Show More
29m 48s
Sep 9
Our Funniest & Most Cringe Mistakes as Entrepreneurs (+ How to Recover When Things Go Sideways)
Some mistakes feel so big in the moment that you wonder how you’ll ever recover. Trust me, Chris and I have been there more times than we can count. In this episode, we share the behind-the-scenes bloopers that used to feel catastrophic but actually taught us how to lead, laugh a ... Show More
21m 15s
Jul 2021
How to Decide Whether You "Should" or Shouldn't
Here’s the truth: the number of business decisions that you're going to need to make as your business grows is only going to increase. ‍‍Cut your lead gen costs in HALF with my $37 mini-course–NOW only $17!Visit The Art of Online Business website for Facebook Ads help‍‍ ‍‍ ‍ ... Show More
25m 3s
Mar 2025
219. Which Investing Platform Should I Choose? Advisor vs. Robo-Investor vs. DIY
Register for our free investing workshop: https://herfirst100k.com/secrets  Investing your money is one of the most powerful ways to build wealth—but before you even buy your first stock, you’re faced with one of the biggest questions: Which investing platform should you choose? ... Show More
47m 10s
Sep 10
The 7 Biggest Mistakes People Make in Retirement (And How to Avoid them!)
In this episode of the Personal Finance Podcast, we are going to talk about the 7 biggest mistakes people make in retirement. How Andrew Can Help You: Listen to The Business Show here. Don't let another year pass by without making significant strides toward your dreams. "Master Y ... Show More
53m 47s
Apr 2025
228. The Most Important Financial Decision You'll Ever Make (That NO ONE Talks About)
Worried about the stock market or a possible recession? Register for our FREE 'Don't Panic' workshop for your 3-step plan for financial security in 2025: herfirst100k.com/SOS We spend so much time stressing over budgets, investments, credit scores—basically, all the numbers. But ... Show More
48m 56s