If I Had To Start Over Investing in 2026, I’d Do This.

Introduction – Getting Started with Investing (0:00)

Bo: If you’re just starting to invest, you probably have a lot of questions, but luckily, we’ve got a lot of answers. We’re going to break down the whole process for you today to get you up and running on your wealth building journey. This is a topic that gets me so excited. So, let’s dive right in. As with any topic, there are really five broad questions you want to ask to get started. That’s who, what, when, where, and why. We’ll throw how in there at the end as well. So technically six questions, but when it comes to investing, we’re going to start with why.

Why Should You Invest? (0:29)

Bo: Why should you invest? Well, let’s look at two examples, both 25 years old. Over a 40-year working career, they’re each going to save $500 a month or $240,000 in total. Remember that number, $240,000. When they both reach retirement age at 65, one of them is going to have $240,000, but the other will have over $3.1 million. Not only that, but that $3.1 million can generate $124,000 a year in retirement income. If the other person tried to do the same thing with the $240,000, they would run out of money in less than 2 years. The one with $3.1 million invested and they end up with way more than the one who simply saved and socked that money away into their mattress.

Bo: So compound interest can allow your wealth to grow exponentially rather than linearly. It can generate sustainable income to fund retirement and it can actually protect your dollars against inflation. The biggest trap to avoid is thinking you need to wait until later to start. Maybe you think you’re too young or you don’t have enough money or whatever the excuse may be. If you’re watching this and have not gotten that wealth-building train rolling, let this be the wakeup call. Because when you’re young is when those dollars are the most powerful. Those dollars have more time to compound and grow upon themselves over and over until it’s literally a runaway train that you couldn’t stop even if you tried.

Small Amounts Make a Big Difference (1:58)

Bo: And if you think you don’t have enough money, know this. A little can go a long way. Let’s go back to that original example. Let’s say you don’t have $500 a month to invest when you’re starting out. That’s okay. Let’s say that you can only manage $50 a month. Investing over that same time frame still lands you with over $524,000. So, don’t think that those early dollars aren’t doing any work in your portfolio. They’re literally your heaviest lifters.

When You Shouldn’t Invest Yet (2:26)

Bo: But, we did have that caveat that we said not everyone should invest. Everyone should invest once their immediate needs are taken care of. This means that you have an emergency fund saved in something like a high yield savings account or it could mean that you’ve knocked out all your high-interest debt if you have any. We know that investing is exciting and we want you to get started as soon as possible. However, it’s important not to sacrifice your current or near-term financial security in the pursuit of long-term wealth. Doing so can front-load risk and leave you worse off if you commit money before you’re truly ready.

What Do I Invest In? (3:02)

Bo: But with that comes our next question. What do I invest in? We suggest the vast majority of folks keep it pretty simple and we do that through index funds. Index funds are investment funds designed to track the performance of a section of the market like the S&P 500 which are the 500 largest companies in the US. Instead of trying to pick the individual winners, they spread your money across many companies all at once. For investors who want broader diversification, index target retirement funds can offer a simple solution. These funds bundle US stocks, international stocks, and other asset classes like bonds into a single portfolio and automatically adjust the mix over time as retirement approaches.

When to Invest: Always Be Buying (3:40)

Bo: When it comes to when to invest, we like to keep it pretty simple there. Also, we have a phrase that we like to use around here. Always be buying. Always be buying means investing on a regular schedule, such as every paycheck or every month, no matter what the market is doing. By investing this way, you naturally practice what is called dollar cost averaging. Sometimes you buy when prices are high and sometimes when they’re lower, which smooths out your average purchase price over time.

Where to Invest: The Three Bucket Strategy (4:07)

Bo: But all of this information isn’t super helpful unless you actually have a place to invest the money. So, we need to answer the question of where to put all this money you’re investing. Where you put your money to invest can depend on a ton of different factors: your employment situation, where you’re at in your financial journey, and even things like your tax situation. Broadly speaking, we are a fan of what’s called the three bucket strategy. The idea is that your investments are spread across three distinct tax buckets. Tax-free, tax deferred, and after tax.

Bo: Tax-free accounts like Roth accounts grow and can be withdrawn without future taxes. Tax deferred accounts such as traditional 401(k)s or IRAs give you a tax break today, but you’ll pay taxes later when you pull the money out. After tax accounts like brokerage accounts offer flexibility and they have favorable capital gains treatment, even though you don’t get a tax deduction on the front end. The core idea behind this strategy is flexibility. It gives you more control over your tax rate in retirement. Instead of being forced to take income from a single type of account, you can choose which bucket to draw from each year, helping manage how much you owe in taxes and avoid unnecessary tax spikes.

Asset Location Strategy (5:14)

Bo: It also allows you to be intentional about asset location, placing investments in the accounts where they’re most tax efficient when you’re managing diversification yourself rather than using a target date fund. For example, higher growth assets like equities often work best in tax-free accounts such as a Roth IRA where future gains won’t be taxed. Lower return or income producing assets like bonds or fixed income may be better suited for taxable brokerage accounts where the tax impact is more limited. This approach can improve efficiency while still maintaining proper diversification.

How to Actually Do It: Forced Scarcity (5:48)

Bo: But all of this information is useless unless we talk about how to actually do it. And one way we suggest people get started investing is to create what is called forced scarcity. Forced scarcity means paying yourself first by investing before you have a chance to spend the money elsewhere. This typically starts with automatic payroll contributions to accounts like a 401(k) or health savings account, followed by scheduled transfers from your checking or savings accounts into like a Roth IRA or a brokerage account. What this does is ensure that investing happens consistently without relying on willpower or memory. By removing the money from your available spending balance before you see it, you’re less likely to rationalize spending it elsewhere. This creates a healthy constraint that trains you to live on what’s left and prioritize your future self.

Set It and Forget It (6:33)

Bo: Once the money reaches an investing platform like Fidelity or Schwab, you can set rules for how much to invest, what to invest in, and when those investments occur. By automating the entire process and adopting a set it and forget it approach, you can remove emotion and decision-making from investing and help yourself to achieve more consistent progress over time.

Closing (6:54)

Bo: If you want to know more about the rules of investing, click right here. And as always, keep building towards your great big beautiful tomorrow.