Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

What if the “financially optimal” choice doesn’t actually lead to your best life?

This conversation explores the balance between optimizing money and optimizing happiness. We break down the Five Types of Wealth—financial, time, social, mental, and physical—and show why sometimes the decision that looks inefficient on paper may actually be the smartest for your overall wellbeing.

From real-life examples like paying...

Some choose to grind a few more years in a high-paying job they dislike, aiming for an early, full stop at retirement. Others step into more fulfilling work that pays less, but adds purpose to their days—and often still results in more wealth than expected.

Take John and Jennifer. Both start at age 50 with $1M saved and $150K salaries. John works five more years at a job he doesn’t enjoy, retiring at 55 with $1.62M. Jennifer switche...

Estate planning isn’t fun to think about, but skipping it can cost loved ones time, stress, and money. In this week's episode, Ari breaks down the essentials so you can take action with confidence.

Learn the key differences between wills and trusts, which states make trusts especially valuable, and why even residents of “will-friendly” states might still need one. Explore the “dead box” strategy, an annual practice that keeps i...

Money conversations fall short when only one spouse is at the table. It’s easy to treat financial planning like another household task to divide and conquer, but unlike errands, your financial plan is the blueprint for your shared future.

What we’ve seen time and again is that the person sleeping next to you often holds the key to your blind spots. They know what stresses you out, what brings you joy, and what dreams you’ve stopped ...

Estate planning doesn’t have to be complicated. This episode breaks down the essentials: wills, trusts, and what actually matters, so you can protect your assets and give your loved ones peace of mind.

Wills determine where assets go after death. Trusts do that and more. They can manage assets during your lifetime and help avoid probate, offering more flexibility and control.

In states like Texas, Arizona, and Florida, probate tends ...

What does soccer have to do with retirement? A lot more than you'd think. As a 5'5" former college soccer player turned financial advisor, I’ve learned it’s not about brute strength. It’s about smart decisions. That mindset guides the way I approach financial planning today.

At 29, people ask why I care so much about retirement. The answer is simple: good planning gives you time. And time with the people you love is t...

The hardest part of retirement isn’t always financial, it’s psychological. For many, stepping away from work isn’t a light switch, but a dimmer that adjusts over time. This episode of Root Talks unpacks what makes the retirement decision so complex, especially for high-achieving professionals whose identity is tied to their careers.

Through a real-life case study, the conversation explores how severance offers can become powerful “t...

Ready to feel more motivated about retiring early? These five research-backed stats reveal how early retirement can positively impact everything from health to relationships—and might be the nudge you need to take your financial independence plan more seriously. The benefits go well beyond just having more free time.

While many people delay retirement out of fear or uncertainty, the data shows that stepping away from work earlier ca...

Too many people delay retirement just to boost their Social Security benefits, often at the cost of time, energy, and joy. But at Root, we believe retirement planning should be about more than just maximizing one metric. It should be about maximizing your life.

If you're working extra years simply to avoid gaps in your earnings history or to earn a slightly higher monthly benefit, it's worth rethinking the bigger picture. ...

If you’ve ever found yourself wondering whether you really need a financial advisor, this episode is for you. James and Ari unpack the deeper reasons people seek financial guidance—and why the decision often goes far beyond dollars and cents.

Much like seeing a doctor for preventative care, working with the right advisor is about protecting your future, reducing stress, and reclaiming your most precious resource: time. From saving 2...

We often focus on the fear of running out of money in retirement—but what if the bigger risk is running out of health before you can enjoy it? After watching The Amazing Race, I was reminded of a client story we hear all too often: years of diligent saving, only to be sidelined by health issues just before retirement begins.

At Root, we’ve seen clients retire with more than enough—only to realize the extra working years came at the ...

What if work became a choice, not a requirement?

The Early Retirement Podcast is here to help you navigate the path to financial independence, so you can retire when you want and live how you want. Whether you’re nearing retirement or just starting to plan, this podcast delivers clear, actionable insights designed to simplify your biggest financial decisions.

We focus on strategies that make a real impact—from tax planning moves that...

You’ve probably heard that maxing out your 401(k) and IRA is the smartest move you can make. But for many investors, that strategy alone may lead to a surprising challenge: becoming "qualified rich, cash poor." In other words, having plenty saved, but locked away in accounts you can’t easily access without tax consequences or penalties.

That’s where the often-overlooked brokerage account comes in.

Also called a taxable, ind...

Retirement doesn’t come down to a magic number, it comes down to your number. In this episode, we walk through a simple, personalized framework to help you understand when you can truly retire, based on what you want life to look like, not generic benchmarks.

We cover the core question: How much do you want to spend each month? From there, we reverse-engineer your retirement target, factoring in taxes, withdrawal strategies, estate ...

Tax gain harvesting is one of the most underused but powerful strategies available to early retirees and those pursuing financial independence. In this episode, we explore how it works, who it's best suited for, and how it can help reduce long-term tax liability.

Unlike tax loss harvesting, which involves selling investments at a loss to offset gains, tax gain harvesting is about intentionally realizing gains when you're i...

What does it really mean to change someone’s life through financial advice? While we’re not saving lives like doctors, the impact we have on our clients’ futures can be just as meaningful. Often, it’s not about the numbers—it’s about helping someone move forward when fear is holding them back.

We’ve seen it firsthand. Like the dentist who had every detail in place to open her own practice but couldn’t take the final step. What helpe...

You don’t need $2 to $3 million to retire unless your lifestyle truly requires it. In this episode, we break down why your retirement number should be built around your personal spending needs, not a one-size-fits-all benchmark.

With a well-diversified $1.5 million portfolio, many retirees can support $60,000 to $75,000 per year in spending, especially when using flexible withdrawal strategies that adjust with market conditions. We ...

Retiring early doesn’t mean cutting out everything you love, it means being intentional about what truly adds value to your life. In this episode of Root Talks, we take a closer look at the spending choices that can either delay or accelerate your path to early retirement. 

We explore which tradeoffs are worth making, where small changes can have a big impact on your timeline, and why some expenses are still worth every penny. This ...

In this episode, Ari and James explore the emotional and practical sides of retiring—specifically, how to have the conversation that officially ends your career.

Whether you're months away or years out, this discussion tackles the fear, hesitation, and freedom that come with telling your boss you're done. You'll hear real stories from Root Collective members who’ve taken the leap, insights on counteroffers, ...