Top Investing Mistakes to Avoid in 2026

27 Dec 2025 · 10 min · 5 chapters

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Earn Your Leisure Podcast Episode Notes: Top Investing Mistakes to Avoid in 2026

Episode Overview In this episode, hosts Rashad Bilal, Ian Dunlap, and Troy Millings discuss the critical investing mistakes to avoid in 2026 and provide practical strategies to navigate an evolving financial landscape. The conversation is designed for both novice and seasoned investors aiming to refine their investment strategies.

Key Themes and Discussions

Major Investing Mistakes to Avoid

  • Not Acquiring Enough Shares:
  • Ian Dunlap stresses the importance of aiming to acquire at least 2,000-3,000 shares of stocks.
  • Emphasis on the belief that 2026 will present significant investment opportunities.
  • Ignoring Your Freedom Number:
  • Investors should focus on defining and working towards their "freedom number," which represents the amount needed to achieve financial independence.
  • Gossip Trading:
  • Troy Millings discusses the pitfalls of making investment decisions based on hearsay or hype instead of thorough research.
  • He highlights the need for discipline and careful analysis in trading, contrasting it to gambling.

Practical Strategies for 2026

Rashad Bilal outlines 10 essential steps for investors

  1. Create a Budget: Utilize budgeting apps like YNAB, Rocket Money, or Monarch Money.
  2. Set Up Systematic Monthly Investing: Implement dollar-cost averaging to invest consistently.
  3. Maximize Retirement Contributions: Take full advantage of tax benefits available through retirement accounts.
  4. Review Beneficiaries: Regularly update beneficiaries in bank and brokerage accounts.
  5. Commit to Continuous Education: Aim to watch one documentary weekly and read one book every 60 days.
  6. Map Out Accountable Goals: Use the "12 Week Year" strategy to break down annual goals into manageable segments.
  7. Stay Informed and Adaptable: Constantly review financial markets for shifts.
  8. Avoid Impulsive Trading: Maintain a disciplined approach to investing.
  9. Build Knowledge: Understand the companies and assets you invest in.
  10. Network and Partner: Engage with others to stay accountable and share insights.

Key Takeaways

  • Planning is Crucial: The biggest mistake investors can make is failing to have a clear investment plan and the discipline to follow through with it.
  • Shift in Financial Landscape: 2026 is positioned to be a transformative year for investors, necessitating a proactive approach.
  • Education and Research: Continuous learning and understanding the fundamentals of investing are essential for long-term success.
  • Community Engagement: Sharing knowledge and strategies with peers can enhance investment outcomes.

Call to Action Listeners are encouraged to define their freedom number for 2026 and share the steps they are taking to secure their financial futures in the comments.

Conclusion This episode serves as a valuable guide for investors looking to navigate the complexities of the financial market in 2026, providing both practical advice and a clear roadmap for success.

*Be sure to subscribe for more insights on wealth-building and financial mastery from the Earn Your Leisure Podcast!*

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Investing Mistakes to Avoid

4:14 to 6:10

Discussing critical investing mistakes to avoid in 2026.

“I want to be very honest and get back to the old style of how I used to be things and super blunt about it.”

Exploring NLP and Mind Control

7:05 to 7:44

Discussion about NLP and its implications on behavior and persuasion.

“If you could control the behavior of anybody around you, what kind of life would you have?”

Financial Planning for 2026

9:16 to 10:48

Tips and strategies for effective financial planning in 2026.

“A new year doesn't mean erasing who you were.”

Budgeting Strategies and Education

10:48 to 14:00

Advice on budgeting, setting up financial systems, and continuous learning.

“that short-term success can lead into long-term wealth strategy.”

Commit to Continuous Learning

14:00 to 16:04

Learn the importance of committing to education through books and documentaries.

“insurance, but also even like your bank account and brokerage account and anything that you have that's going to get passed on to somebody, review the beneficiaries, keep the beneficiaries updated because you never know.”
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Transcript

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0:00This is an iHeart Podcast. Guaranteed Human.

0:31Can you hypnotize someone into sleeping with you? Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, a.k.a. neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hello, hello, all my people. What's up? It's Questlove. Recently, I had the opportunity to sit down with the one and only A$AP Rocky. He reflects on his journey from Harlem roots to global icon status and discovering the hip-hop origin of his name.

1:14The ledge was on the TV. Rakim had the Buckethead Kangol join on. Pops was like, that's Rakim. That's who you named after. I just, damn the f***ing f***ing swag. But listen to the Questlove show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you.

1:58Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Hey, it's Joel. And Matt. From HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

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3:11There's this West Indian spot right in our community that started with a small takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even started catering events across the city. That's the kind of growth that inspires us, and it's powered by Square. Square is built for all types of businesses, from the corner bagel shop that turned into a local chain, to the specialty market with thousands of unique items, to the stylist who's been holding you down for years. If you're a business owner or even just thinking about launching something soon, Square is hands down one of the best tools out there to help you start, run and grow.

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4:35I know some people want to say I don't have the capital to do it, but. find a way because i think next year is probably going to be the most interesting year in investing that we've had probably since 2020 um number two double down on what your freedom number is and put a lot of cash into making that a reality they just told you they're working like crates shout out to the interviews y 'all got coming out i won't say nothing but they're working hard. Magic Johnson told you at InvestFest. Gary V working hard. Every top entrepreneur is busting ass right now. And that's because there's going to be a seismic change that comes in 26 and 27.

5:19Now is not the time to play or get comfortable with every success you have accumulated from 2020 through now because you're going to need more than 26 and 27. Lastly, I will say you got to block out all the noise. All that noise online. I would say this, and Rashad and I talked about it on Blackout. Troy does an amazing job of it, of staying off social. You probably need to spend 60 % less time on social media in 2026. Jake Paul ran up$100 million. Anthony Joshua ran up$90, but he got to pay$45 in taxes. These big numbers are being thrown around for a reason. So I'm begging you right now, lock in for 2026.

6:04and I want everyone to put in chat what is your freedom number for 2026. What do you guys think? Biggest mistakes are. Let's just talk like it's us. Biggest mistakes? I think trading off of Hearsay. It's like that meme stop craze but a little bit more elevated than that. It's like, yo, I saw this company. I heard them say this company and let me just invest in it. Not really knowing anything from a technical side of the fundamentals. Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts than ad-supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined.

6:46So whatever your customers listen to, they'll hear your message. Plus, only iHeart can extend your message to audiences across broadcast radio. Think podcasting can help your business? Think iHeart. Streaming, radio, and podcasting. Call 844-844-iHeart to get started. That's 844-844-IHEART. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you?

7:20I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. NLP, aka Neuro Linguistic Programming, is a blend of hypnosis, linguistics, and psychology. Fans say it's like finally getting a user manual for your brain. It's about engineering consciousness. Mind Games is the story of NLP. It's crazy cast of disciples and the fake doctor who invented it at a new age commune and sold it to guys in suits. He stood trial for murder and got acquitted. The biggest mind game of all? NLP might actually work. This is wild. Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

8:08Hey, what's up, y 'all? This is Questlove. Recently, I had the opportunity to sit down with A$AP Rocky ahead of his album release, Don't Be Dumb. He reflects on his journey from his Harlem roots to global icon status, discovering the hip-hop origin of his name. The ledge was on the TV. Rakim had the bucket hat Kangol join on Pops was like that's Rakim that's who you named after I just was like damn that was I swear Rocky offers a window into not only a boundary breaking artist but as a man committed to fusing creative ideas community and remaining unapologetically himself have you ever gotten roasted for any of your outfits?

8:46for sure some people don't be getting the vision look they can roast me they can cook me they can deep fry me they can saute whatever they want there's nobody who can f*** with my fashion sense and my taste is impeccable. I'm just like, I impress myself a lot. It's an amazing conversation, one you definitely don't want to miss. So listen to the Questlove show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't mean erasing who you were. It means honoring what you've survived and choosing how you want to grow. It means giving ourselves permission to feel what we've been holding and knowing that it's okay to ask for help.

9:30I'm Mike Della Rocha, host of Sacred Lessons. This podcast is a space for men to talk openly about mental health, grief, relationships, and the patterns we inherit, but don't have to repeat. Here, we slow down. We listen. We learn how vulnerability becomes strength and how healing happens in community. not in isolation. If you're ready to let go of what no longer serves you and step into the year with clarity, compassion, and purpose, Sacred Lessons is your companion on your healing journey. Listen to Sacred Lessons with Mike De La Rocha on America's number one podcast network, iHeart. Follow Sacred Lessons with Mike De La Rocha and start listening on the free iHeart radio app today.

10:16New year, new goals, and in this economy, a better money plan is more necessary than ever. I am Matt and I'm Joel. We are from the How to Money podcast and every week we help you to spend smarter, save more and make sense of what's going on out there. If you want 2026 to be the year you finally feel in control of your money, we're here to give you the tools and advice to help you make it happen. Listen to How to Money on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts. I was doing it. I think a lot of times when people get early success, they think that that short-term success can lead into long-term wealth strategy.

10:52And they start doing things like over-trading, start taking, you know, same-day options, trades, not having any idea, just trying to replicate the feeling of what they had in that short-term win. And that's when people lose money. And we're seeing that more and more. And I think if we don't get it right, if we're not disciplined, if we don't have a proper approach, if we don't have a plan, it's only going to get worse. because and even when talking to vlad and we're talking about predictive markets people are treating their broker's account like it's fanduel or it's draft kings and it's not um yeah so you you gotta you gotta be disciplined about this but you actually have to to know knowing is important like we can overstate it and we can it's important to know what you're investing in yes get to a thousand shares.

11:45Let's start with getting to five and understanding what the company you just invested in does. Right? Because the more understanding you have, the more education you have around it, the more conviction you have when people start to doubt what you're saying. I'm only speaking from experience. Like literally, you've seen this over the past six years. We say something, I'm not budging on that because I believe in what I'm saying. And if it's a great company that doesn't have a great year, fine. But a lot of times, these are great companies that are having great years because there's conviction education behind it so be disciplined in it don't gossip trade right really understand what you're doing and why you're doing it shawty what you think top mistakes uh that people can make in 2026 well i i'm wanting to do something i actually put together a list of things that people should do okay i love it oh yeah because um i think that that's important to kind of have some level of a blueprint.

12:40Biggest mistake I think is not having a plan. So with that being said, I put together 10 things I think everybody should do in 2026. And that's the first thing is put together a budget and a few budgeting apps for you if you're interested. YNAB, you need a budget, Monarch money, Rocket money, Capital money, every dollar, Pocket guard, good budget, and simplify by Quicken. so I mean you could what I used to do is just pen and paper yeah right I think that's the best way but if you actually want some level of like digital help in it um those are all sites that you can use or apps that you can use for budgeting that's the first thing the second thing is to set up a systematic dollar cost averaging plan um to invest every single month especially if you're first starting out.

13:34So whether that's the 15th, usually it should be around the time you get paid. So if you get paid on the 12th, then try to do it on the 15th. Set up a retirement account if you don't have one. And if you do have one, try to contribute more so you can benefit from the tax savings from that. Review all your beneficiaries. That's important. That's a good one. Not just life insurance, but also even like your bank account and brokerage account and anything that you have that's going to get passed on to somebody, review the beneficiaries, keep the beneficiaries updated because you never know. Commit to one, commit to your education.

14:15I recommend one documentary a week and one book every 60 days. So that would be, I don't think that that's too hard to accomplish, especially you can listen to an audio book, but that average person, they said, doesn't read any books a year. And I think the average CEO reads like two books a month. So if you start to really dedicate to one book every 60 days, that's six books a year. You're off to a good start. And like I said, the documentary, I think the documentaries, they just expand your horizon and have you think a little differently. And it's so many great documentaries that you can just find on YouTube and Netflix.

14:54So one documentary a week, one book every 60 days, map out your goal for the next 12 months, but do it in a, I think everybody should read the book, 12 Week Year. Yeah, it's a really good book. You don't just map out your goal and just say, I want to make$100 ,000. I want to make$500 ,000. That's not really a goal. That's a wish. There's actually a systematic way to actually go about that. We broke this down at EY University, but that book actually explains it. The purpose of the book is that you break the year into micro years. Yeah. And you have goals, like weekly goals, biweekly goals that helps you get to the goal quicker.

15:32And then you actually have to list the action steps of how you're actually going to accomplish the goal. Because like I said, I'm going to make$500 ,000 a year. What does that really mean? That's not a goal. Like I said, that's a wish. You got to actually list out the actionable steps that you need to take to make $500 ,000 a year. Then you got to hold yourself accountable on a short-term basis, preferably weekly to see if you're actually hitting those numbers or not. So everybody should commit to that. Or have accountability partners in there. Yeah, for sure. This episode is brought to you by PNC Bank.

16:07A lot of people think podcasts about work are boring. And sure, they definitely can be. But understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank. It might seem boring to save, plan, and make calculated decisions with your bank. But keeping your money boring is what helps you live a more happily fulfilled life. PNC Bank, brilliantly boring since 1865. Brilliantly boring since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association, member FDIC. What if mind control is real?

16:48If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings. Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, a.k.a. neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

17:50Just damn the f***ing sweat. Listen to the Questlove Show on the iHeartRadio app, Apple Podcasts, or wherever you get your podcast. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

18:31This is Dr. Jesse Mills, host of the Mailroom Podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

19:03Hey, it's Joel. And Matt. From How To Money. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.

From the publisher

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

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