Invest Time

The Best Time to Build Your Future Was Yesterday

May 01, 20256 min read

Let’s skip the sugarcoating.

I didn’t start investing until I was 27, and looking back, that was my first financial misstep. The second? I didn’t start with enough urgency. I dabbled. I tested the waters. But time doesn’t wait for you to get comfortable.

By the time I hit my 30s, my investment strategy had changed significantly. I became more calculated, more disciplined, and more aggressive. I diversified into land, stocks, ETFs, and protected-growth vehicles. And while I’m proud of how far I’ve come, there’s no denying one truth:

If I had started earlier, everything would be different.

💡 Pay Yourself First: The Principle I Wish I Lived by Sooner

If I could go back and talk to the 20-year-old version of myself, young, in uniform, focused on missions and next month’s schedule, I’d say this:

“Treat your financial future like it’s sacred. Pay yourself like a tithe, 10% of every paycheck, before anything else.”

I didn’t know it then, but that simple mindset would have been a game changer. I would have set up an automatic habit that scaled with my income. I wouldn’t have had to play catch-up later. I would’ve bought time, the most valuable asset in wealth-building. Back then, I thought I needed thousands to start investing. But what I really needed was a mindset shift: Start small, stay consistent, and begin now.

📊 The Cost of Delaying: Why Time Matters More Than Money

Let’s get real about what waiting costs you.

Imagine you receive a $10,000 enlistment bonus at 20 years old. After 22% federal taxes, you’re left with $7,800, real money you could invest.

If you invest that $7,800 at 7% annual returns:

  • At age 60, it could grow to approximately $116,753.¹

  • If you wait until 30, it only grows to about $59,331.

  • If you wait until 40, it drops to around $30,155.

Same bonus. Same soldier. Totally different futures, all depending on when you start. It’s not about how much you make. It’s about when you start making it work for you. The younger you are when you plant those seeds, the stronger your financial tree grows. The later you start, the more you’re playing catch-up, and the harder the climb.

🔄 How Waiting Changed My Path

Because I didn’t start until 27, and even then, not at the level I should’ve, I had to course correct. That meant taking bigger risks than I would’ve liked. It meant getting into investments I might’ve avoided if I had more time on my side. I had to hustle more aggressively, and I had less margin for error. Not because I was reckless, but because I was behind. Looking back, I regret that I never maxed out my TSP, even when I could have. I also often didn’t fully fund my Roth IRA, letting critical compounding years slip away.

One of the biggest missed opportunities? I never started an Indexed Universal Life (IUL) policy while I was young, healthy, and still growing my income. I missed out on tax-free growth, lifetime protection, and flexibility.²

The opportunities were there. I just didn’t seize them early enough.

📘 Bruce’s Story: What Starting Early Really Looks Like

Let me tell you about Bruce.

He bought his first duplex at just 19 years old and got this with a 7.25% interest rate. So do not tell me today’s interest rates are too high to get started. He made it happen.

That duplex? Completely paid off now.

Today, he owns that duplex plus three additional single-family homes. The total property value is around $1.4 million, and his equity in those properties is approximately $600,000.

Bruce did not start contributing to a 401(k) until age 27, and did not begin maxing it out until age 37. Even so, it is now worth about $225,000. He began investing in an IRA at age 20, had less than $25,000 in it by age 30, but started maxing it out at age 33. Now, his IRA is worth approximately $200,000. His wife followed a similar path; her IRA is now worth about $175,000.

And here’s the kicker: They did most of this on a single income. His wife worked off and on, but they lived below their means, stayed focused, and did not waste opportunities.

Bruce’s current net worth? Over $1.2 million and neither he nor his wife is even 40. This is what it looks like when you start early, stay consistent, and live with discipline. Bruce did not come from money. He didn’t get lucky. He didn’t win the timing lottery. He simply made smart, boring, repeatable decisions early, and stuck with them.

And as Bruce told me once: “Don’t wait to start investing. Live below your means, and it will pay off in time.”

Then he followed it up with this truth bomb: “The fastest way to destroy personal or family wealth is divorce. You’ve got to stay solid on the home front, too.”

Bruce’s story isn’t a flex. It’s a blueprint. One that any soldier, any spouse, any young earner can follow if they’re willing to get serious early and stay the course. I didn’t heed his advice when he bought his duplex.

🎯 My Challenge to You: Make Time Work for You

You don’t need a windfall. You don’t need a perfect plan. You just need to start and start now.

Ask yourself:

  • Can you set aside $100/month, less than a weekend of impulse spending?

  • Can you sacrifice a gadget today to buy yourself decades of financial freedom tomorrow?

  • Can you build a habit now that stacks dividends, security, and choice for your future self?

Because here’s the brutal truth nobody told me at 20: Every dollar you waste today isn’t just lost money it’s lost future freedom. You don’t just lose the $100 you spent at the bar; you lose the $1,000 or $5,000 or $10,000 that money could have grown into.³

You’re not just buying stocks or funds or insurance. You’re buying options. You’re buying freedom. You’re buying a future where you call the shots, not where you’re stuck reacting to life’s punches.

Every soldier knows: Complacency kills. It kills careers. It kills futures. It kills freedom. The same is true for your finances. Because every dollar you invest now isn’t just money, it’s future freedom your older self will either thank you for—or wish to God you had fought harder to earn.

🧠 Final Word: You’ll Either Be Grateful or Regretful

Start while you’re still learning. Start before you feel ready. Start while the military covers your chow, your housing, your healthcare and use that blessing to your advantage. Because someday, your 40-year-old self will look back and say either:

  • “Thank God I started,” or “Why didn’t I do this sooner?”

You get to decide which one it’ll be.

Start Early, Start Small, The Power of Compound Growth

📅 Want help getting started?

Book a call with me. I’ll help you figure out the smartest next steps, whether it’s building your TSP, funding a Roth IRA, or setting up a protected-growth strategy like an IUL.

You don’t have to figure it out alone.


Footnotes

  1. Jeremy Siegel, Stocks for the Long Run, 6th ed. (New York: McGraw-Hill Education, 2022), 23–27.

  2. John C. Bogle, The Little Book of Common Sense Investing, 10th ed. (Hoboken, NJ: Wiley, 2017), 34–41.

  3. Robert R. Johnson and Paul D. Kaplan, “The Long-Term Returns on the Original S&P 500 Companies,” Journal of Investing 29, no. 3 (2020): 25–33.

Guy Bester is the co-founder of DarkHorse Insurance Solutions, a veteran owned agency committed to empowering families with smart, lasting protection. With a strong background in financial services and legacy planning, Guy specializes in helping clients build wealth while protecting what matters most through tools like Mortgage Protection, Indexed Universal Life (IUL), and tax-free retirement strategies. When he's not educating homeowners or business owners about their options, he’s focused on helping fellow veterans and families create financial legacies that last generations.
#GetInsuredWithGuy

Guy Bester

Guy Bester is the co-founder of DarkHorse Insurance Solutions, a veteran owned agency committed to empowering families with smart, lasting protection. With a strong background in financial services and legacy planning, Guy specializes in helping clients build wealth while protecting what matters most through tools like Mortgage Protection, Indexed Universal Life (IUL), and tax-free retirement strategies. When he's not educating homeowners or business owners about their options, he’s focused on helping fellow veterans and families create financial legacies that last generations. #GetInsuredWithGuy

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