Investing 101: Jack Doshay Explains How to Start with Confidence

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Building wealth starts with a single decision: to invest. But for many first-timers, that first step can feel overwhelming. Between market volatility, confusing acronyms, and fear of losing money, it’s no wonder so many delay getting started. 

The good news is that you don’t need to know everything to begin. What you need is a clear, structured path, and the confidence to follow it.

Here’s how new investors can start smart, minimize mistakes, and build long-term momentum.

Start with the Foundation

Before investing a single dollar, it’s essential to shore up your financial base.

According to the Federal Reserve’s 2023-2024 report, only 63% of U.S. adults could cover a $400 emergency expense with cash. That statistic alone underscores why an emergency fund, typically 3-6 months of essential expenses, is the first step toward financial security.

Credit card debt is another priority. With average APRs exceeding 20% as of early 2025, high-interest debt can quietly sabotage even the best investment strategy. Paying it down first gives your investments room to grow without friction.

Choose the Right Investment Accounts

Where your money goes matters just as much as what it goes into. Tax-advantaged accounts can help you keep more of your gains.

For example:

• The 2025 IRA contribution limit is $7,000 (or $8,000 if you’re 50+).
• 401(k) plans allow contributions up to $23,000, not including employer matches.
• If you’re enrolled in a high-deductible health plan, an HSA offers a triple tax advantage with contribution limits of $4,300 (individual) and $8,550 (family).

Jack Doshay, a financial education consultant, puts it plainly: “Don’t let tax drag eat away your returns. Maxing out the right accounts early, even in small amounts, makes a big difference over time.”

Pick Investments That Align with Your Goals

Once the account is chosen, the next decision is what to buy. Many beginners benefit from keeping it simple.

Consider these beginner-friendly options:

• Target-date funds: One-stop portfolios that automatically adjust as you age.
• Three-fund portfolios: A blend of U.S. stocks, international stocks, and bonds.
• Broad-market ETFs: These offer built-in diversification and lower fees.

It’s not about beating the market; it’s about building a reliable plan that reflects your risk tolerance and timeline. According to the 2025 Global Investment Returns Yearbook, global equities delivered an annualized real return of 5.2% over the past 125 years (1900–2024), significantly outperforming bonds (1.7%) and Treasury bills (0.5%) over the same period.

Keep Costs Low and Stay the Course

Expense ratios may look small, in terms of fractions of a percent, but they gradually increase.

Morningstar reports that the asset-weighted average expense ratio in the U.S. dropped to 0.34% in 2024, while index funds average around 0.11%. Every tenth of a percent you save in fees is a direct gain to your returns.

That said, the real challenge isn’t picking the right fund; it’s sticking with it. The “behavior gap” describes how investor returns often lag behind fund performance by nearly 1.7 percentage points, simply due to poor timing and emotional decision-making.

“Confidence doesn’t mean always being right,” says Jack Doshay. “It means having a plan, automating where you can, and tuning out the noise when things get bumpy.”

Automate, Rebalance, and Recheck

Confidence grows when investing becomes routine.

Set up recurring contributions each month, which is known as dollar-cost averaging, to reduce emotional decision-making. Even though lump sum investing historically wins about two-thirds of the time, automation helps you build discipline and stay consistent.

Rebalancing 101:

• Once or twice a year, revisit your portfolio.
• Shift funds back to your target allocation if needed.
• This helps manage risk, especially after market swings.

Studies show that annual rebalancing provides a solid balance between cost, control, and long-term performance. Threshold-based rebalancing can also slightly improve outcomes for experienced investors.

Know Tax Efficiency and Account Safety

If you’re investing in a taxable account, basic tax knowledge is critical.

• Capital gains taxes apply when you sell investments at a profit.
• You can’t deduct a loss on a security sale if you repurchase the same or a substantially identical investment within 30 days before or after the sale. This is known as the wash-sale rule.
• ETFs tend to be more tax-efficient than mutual funds due to their unique structure.

And yes, your money is safe from fraud, too. Brokerage accounts are insured by SIPC up to $500,000 (including $250,000 for cash), and FDIC insurance protects bank savings up to $250,000 per depositor.

Still, investors should remain vigilant. Scams targeting new investors, particularly those involving crypto or fake advisors, are on the rise. Tools like FINRA’s BrokerCheck help verify credentials before you commit funds.

You Don’t Need a Lot to Begin

The idea that investing is only for the wealthy no longer holds. In 2025, 62% of Americans own some form of stock, a sign that access has widened significantly. Today’s platforms are built for inclusion, not exclusivity.

Thanks to fractional shares, you can now invest in major stocks or ETFs with as little as $1. Firms like Fidelity, Schwab, and others let new investors buy small slices of companies like Apple or Google without needing hundreds of dollars upfront.

This shift removes one of the biggest barriers to entry: affordability. It’s not about timing the market or hitting home runs. It’s about starting early, investing consistently, and growing your portfolio one piece at a time.

Final Thoughts

Starting with confidence doesn’t require market mastery. It requires clarity. When you focus on the basics, including clearing debt, setting up the right accounts, choosing simple investments, and automating your contributions, you give yourself space to learn and grow.

The path to financial independence is long, but the starting point is surprisingly straightforward. Build your plan. Stick to it, and let time do the rest.