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Earn Your Leisure

Top Investing Mistakes to Avoid in 2026

Earn Your Leisure

iHeartPodcasts

News, Entrepreneurship, Business, Investing, Careers, Education, Business News

4.87.8K Ratings

🗓️ 27 December 2025

⏱️ 10 minutes

🧾️ Download transcript

Summary

Are you ready for 2026? In this Market Mondays clip, Rashad Bilal, Ian Dunlap, and Troy Millings dive deep into the biggest mistakes investors might make in the upcoming year—and how to avoid them. Whether you’re just starting your investment journey or looking to refine your strategy, this discussion delivers blunt, practical advice to help you prepare for seismic changes ahead. Ian Dunlap emphasizes the importance of accumulating shares, knowing your “freedom number,” and tuning out distracting online noise. He highlights how top entrepreneurs—like Magic Johnson and Gary Vee—are doubling down because the financial landscape is about to shift. Ian’s no-nonsense approach: find a way to acquire at least 2,000–3,000 shares and stay focused! Troy Millings warns against “gossip trading”—making investment decisions based on hearsay or hype, rather than solid research. He stresses the danger of treating your brokerage account like a gambling app, and why discipline, education, and conviction matter more than ever. Troy recommends starting small, truly understanding the businesses you invest in, and building knowledge for long-term success. Rashad Bilal brings a practical blueprint, sharing 10 essential steps every investor should follow in 2026:

  • Create a budget using popular apps like YNAB, Monarch Money, or Rocket Money
  • Set up systematic monthly investing (dollar cost averaging)
  • Maximize retirement contributions for tax benefits
  • Regularly review and update all beneficiaries
  • Commit to continuous education by watching one documentary a week and reading one book every 60 days
  • Map out actionable, accountable goals based on the “12 Week Year” strategy

The crew agrees: the biggest investor mistake is not having a clear plan and the discipline to stick to it. If you want to set yourself up for real financial success in 2026, this conversation is your actionable guide! 👇 Drop your freedom number for 2026 in the comments and let us know what steps you’re taking to lock in your future. *Be sure to subscribe for more Market Mondays insights on wealth-building and financial mastery!* #MarketMondays #Investing2026 #MoneyMistakes #FinancialFreedom #RashadBilal #IanDunlap #TroyMillings #WealthBuilding #PersonalFinance #StockMarket #InvestmentTips #FinancialPlanning

See omnystudio.com/listener for privacy information.

Transcript

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0:00.0

This is an IHeart podcast. Guaranteed human.

0:04.6

Earners, what's up?

0:05.5

You ever walk into a small business and everything just works?

0:08.7

Like the checkout is fast.

0:10.3

The receipts are digital.

0:11.9

Tipping is a breeze.

0:13.8

And you're out the door before the line even builds.

0:16.2

Odds are they're using Square.

0:18.9

We love supporting businesses that run on Square because it just feels seamless,

0:22.8

whether it's a local coffee shop, a vendor at a pop-up market, or even one of our merch partners.

0:28.4

Square makes it easy for them to take payments, manage inventory, and run their business with confidence,

0:34.1

all from one simple system. One of the things we love mostly seeing neighborhood

0:38.8

businesses level up. There's this West Indian spot right in our community that started with a small

0:44.0

takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even

0:49.8

started catering events across the city. That's the kind of growth that inspires us, and it's

0:55.4

powered by Square. Square is built for all types of businesses, from the corner bagel shop that turned

1:01.2

into a local chain, to the specialty market with thousands of unique items, to the stylist

1:06.5

who's been holding you down for years. If you're a business owner or even just thinking about launching

1:11.7

something soon, Square is hands down one of the best tools out there to help you start, run, and grow.

1:18.3

It's not just about payments. It's about giving you time back so you can focus on what matters most.

1:24.1

Ready to see how Square can transform your business. Visit square.com backslash

1:29.1

go backslash EYL to learn more. That's square.com backslash go backslash EYL. Don't wait.

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