Shows
Ready For RetirementWork at SpaceX? Watch This Before your IPOIf you work at SpaceX, you’re likely holding one of the most valuable (and complicated) assets in the world. With a potential IPO on the horizon, the decisions you make with your SpaceX stock, RSUs, and equity compensation could determine whether that wealth creates freedom or long-term stress.Instead of starting with “What should I do with my stock?”, James explains why the first question has to be “What do I want my life to look like?” Without that clarity, selling, holding, or diversifying SpaceX stock becomes guesswork... even if the company continues to perform well. Us...
2026-02-0118 min
Root ReadyThe One Communication Skill That Actually Changes Client BehaviorMost advisors don’t struggle with knowledge. They struggle with getting that knowledge to actually land.This episode explores one of the most important (and most overlooked) skills in advice: why facts alone rarely change client behavior, and how storytelling bridges the gap between understanding and action. It’s a lesson James learned early in his career through Toastmasters, and one that continues to shape how the most effective advisors communicate today. James breaks down the difference between information, wisdom, and true transformation — and why advisors who rely only on facts often feel frustrated when clients...
2026-01-2921 minReady For RetirementYou Need to Retire Early - Here's WhyThere’s really only one way to reach the level of success most people say they want, and it’s not about working until 65. It’s about having a plan to retire early. Not as a finish line, but as a mindset.Early retirement means your money is working for you, giving you the ability to choose how you spend your time instead of waiting for an arbitrary age when you’re “supposed” to stop working. In this video, James walks through a real case study to show how this mindset changes everything — from cash flow and withdrawal rat...
2026-01-2515 minReady For RetirementI’ve Never Seen So Many Retirees Make This Same MistakeMost retirees who make this mistake aren’t reckless. They’re careful. They’re doing what they believe is responsible, and that’s what makes it so painful to see when it backfires.James explains why the same portfolio mistake is showing up more than ever, whether someone has managed their own investments for decades or relied on professional advice. Different paths, same outcome: a portfolio that isn’t built around how money is actually used in retirement.With people living longer, retiring earlier, and markets remaining volatile, overly simplified portfolio advice has become a real risk...
2026-01-1117 minReady For RetirementThis Is What a $10M Retirement Actually Looks LikeA $10 million retirement is often imagined as the finish line — complete freedom, unlimited spending, and no financial stress. The reality is more complex.James walks through what an eight-figure retirement actually looks like by examining a real planning scenario for a couple entering retirement with roughly $10 million in assets. Rather than focusing on luxury or excess, the conversation centers on how income, taxes, investment structure, and lifestyle decisions evolve once work stops and the margin for error gets smaller. At this level of wealth, the biggest challenge isn’t running out of money. It’s decidin...
2026-01-0414 minRoot ReadyHow Great Advisors Deliver Bad News with Honesty and EmpathyEvery advisor eventually faces the conversation they wish they could avoid — the moment a plan reveals that a client’s expectations don’t match reality. Not a small adjustment. Not a simple tweak. But a result that asks for real change.This episode of Root Ready tackles one of the hardest responsibilities in advice: how to tell a client their plan won’t work without breaking trust, crushing hope, or damaging the relationship. It’s not about sugarcoating the truth. And it’s not about hiding behind software outputs. It’s about learning how to show up as the messeng...
2025-12-3126 minReady For RetirementHere's the Most Unethical Thing Advisors DoSome of the most damaging financial advice doesn’t look shady at all. It looks responsible. It looks optimized. And it looks great on a spreadsheet. This episode breaks down one of the most unethical practices James sees in financial planning, not selling high-fee products, but using projections and tax strategies to justify an advisor’s fee while ignoring the life those numbers are supposed to support. The problem starts when advisors lead with “value creation” instead of purpose. Tax savings, Roth strategies, and optimized projections can be manipulated to look impressive, especially when spending is kept a...
2025-12-2112 minReady For RetirementThe Hardest Year of Retirement: What No One Warned Me About | Retirement RealityRetirement doesn’t always arrive on your schedule. Sometimes it shows up early, uninvited, and forces you to rethink everything you thought you knew.For Jim, that moment came at 5, four years before the retirement date he’d carefully planned for. One unexpected layoff, and suddenly the identity he’d built over decades in big tech was shaking underneath him.In this episode of Retirement Reality, James shares the stress, the fear, and the sense of disorientation that came with having the rug pulled out from under him… and the surprising clarity that followed once the dust...
2025-12-1739 minRoot ReadyThe Logic Behind Our 5-Year Root Reserves StrategyEvery advisor knows the hardest part of portfolio conversations isn’t the math, it’s helping clients feel safe enough to stay invested. And nothing tests that more than explaining why five years in reserves isn’t just a rule… it’s a risk-capacity engine that keeps clients grounded when markets break pattern.This episode reframes the entire conversation advisors have around allocation: not as a static percentage, but as a time horizon matched directly to client cash-flow needs. Five years of Root Reserves, not theory, not guesswork, but a framework built from real market history, g...
2025-12-1723 minReady For RetirementFreedom at 60 Why He Left a Job He Loved (and Doesn’t Regret It) | Retirement RealitySteve spent more than two decades building video games, working with a team that felt more like family than coworkers. By all measures, he loved his work. But a heart attack in 2021 changed everything, and it became the moment that pushed him to rethink the one thing he’d always said he wanted someday: an early retirement.In this episode, Steve sits down with James Conole, CFP®, to share how a health scare, a divorce, and years of slowly learning how to budget and invest turned into the freedom he now wakes up to every day. He did...
2025-12-1038 minReady For RetirementRetired at 50 Freedom, Guilt… and What No One Tells You | Retirement RealityRetiring at 50 sounds bold, almost unthinkable for most people, but for Kent, it was the only decision that made sense once life, loss, and perspective pushed everything into focus. In this conversation, he sits down with James Conole, CFP®, to share the honest story behind leaving work two decades earlier than expected.Kent talks about saving from age 18, building a plan long before he knew what retirement would look like, and the complicated mix of discipline, luck, and family legacy that helped him reach this moment. He also opens up about the emotional side: the guilt of i...
2025-12-0338 minReady For RetirementRetiring With a Pension? Here’s How It Changes Everything About Your Retirement MathRetiring with a pension changes everything about your retirement math.Most people think about retirement in terms of net worth—how close they are to a million, two million, or more. But if you have a pension, that old framework can send you down the wrong path. In this episode, James explains why retirees with pensions need to think in terms of cash flow, not balances on a statement.James begins with a simple shift: a pension that pays $60,000 a year acts like the income from a $1.5 million portfolio under a traditional 4% withdrawal rule. That perspective al...
2025-11-2311 minRoot ReadyWhy We Wait Until the Third Meeting to Talk About Investments (and Why It Works)This episode of Root Ready digs into one of the most overlooked parts of the client process: the proper timing for investments to enter the conversation. It’s a masterclass in pacing, patience, and purpose. You will walk away from this video knowing how smart advisors earn trust and set the foundation before talking portfolios.James unpacks why great planning starts with clarity around lifestyle, cash flow, and strategy — not product recommendations or asset allocation. You’ll learn how to reframe client expectations, keep the process focused on what truly matters, and lead conversations that put life before...
2025-11-1922 minReady For RetirementThe Wake-Up Call That Made Him Retire 10 Years Early | Retirement RealityA cancer diagnosis changed everything. When Michael’s wife began chemo, time took on a new meaning. The long-term financial plan suddenly felt secondary to the years they still had together. That wake-up call led Michael, then 57, to retire a full decade earlier than planned, trading more income for more life.In this conversation with James, Michael shares the mindset shift that made him walk away from a thriving career and a team he loved leading. He opens up about the guilt of leaving, the relief that followed, and the realization that a company replaces you faster th...
2025-11-1932 minReady For RetirementI Threw the First Pitch at a Padres Game—Here’s the Real Lesson | Root TalksWhat if the “smart” money choice isn’t the choice that builds your best life?This Root Talks episode starts with a bucket-list moment for James—throwing the first pitch at a Padres game—and turns into a bigger lesson: money is a tool to create meaning, not a score to keep. It’s a look at the Five Types of Wealth (financial, time, social, mental, and physical) and why the spreadsheet answer isn’t always the human answer.James and Ari share real examples: paying for time to be with family and friends, choosing health over “perfect”...
2025-11-0614 minRoot ReadyStop Talking About the Weather: Better Ways to Open Client MeetingsThis episode of Root Ready dives into the art of first impressions: why small talk isn’t small and how skipping the weather talk might be the smartest move you make. Whether you’re a new advisor or a seasoned planner, this conversation unpacks how to show confidence, warmth, and leadership from the moment a meeting starts.James shares practical strategies for opening virtual meetings in a way that builds genuine rapport and trust without sounding scripted. From the psychology of posture and tone to the power of open-ended questions and clear agendas, you’ll learn how to tur...
2025-11-0519 minReady For RetirementYour Tax Planning Window Won’t Last Forever | Top 3 Strategies to PrioritizeRetiring early isn’t just about having enough money, it’s about using the right tax moves in the right years. This conversation between James and Ari maps the three biggest levers for early retirees: Roth conversions, ACA health insurance subsidies, and 0% long-term capital gains. A real-world case study shows how account mix and spending levels can flip what’s “best,” and how small income shifts can change the math in a big way.The episode breaks down when Roth conversions pay off versus when they backfire, how keeping modified AGI under ACA thresholds can save five...
2025-10-2521 minRoot ReadyStop Ending the Day Exhausted: A Playbook for Peak PerformanceEver finish a day full of meetings or creative work and feel wiped out, even when you love what you do?James did too, until one image changed how he looked at energy forever.After seeing a scan of a “brain on meetings,” he realized the problem wasn’t the work itself, it was the lack of recovery between high-focus efforts. That insight led him to rebuild his days around structure, not hustle: plan like an athlete, recover like one.In this episode, you’ll hear how a simple system (three priorities, real breaks, no dopam...
2025-10-2217 minReady For RetirementWe're 62 with $2M: Retire Now or Wait?The real question isn’t “Can we retire?”, it’s “On how much, and when do the big costs fade so our savings can breathe?”In this episode, James walks through one couples' retirement plan to show how timing, travel, and housing choices can turn a shaky forecast into a confident glidepath.He highlights the income canyon most people miss (the stretch between retiring and starting Social Security) where withdrawals rise sharply, then ease once benefits begin and the mortgage is gone. By front-loading travel for the first ten “go-go” years, delaying Social Security, and planning a mid-7...
2025-10-1813 minReady For RetirementYou Could Spend WAY More Than the 4% Rule Suggests (Says the Man Who Created It)Financial planning’s most famous guideline just got an upgrade. In this exclusive interview, James speaks with Bill Bengen—the MIT-trained engineer turned financial advisor who created the 4% rule—about his updated research and what it means for retirees today.Bengen reveals that diversification alone can raise the safe withdrawal rate to 4.7%, and under certain market conditions, retirees may be able to withdraw 6%, 7%, or even 8% annually. The original 4% rule was never meant to reflect average scenarios. It was built from the worst-case retirement timing in modern history. Even then, a 4% withdrawal strategy lasted 30 years. Bengen’s findings show tha...
2025-09-2021 minReady For RetirementHow to Know You’ve Found the Right Financial Advisor │ Root TalksWhat makes you trust someone with your financial future? In this episode of Root Talks, James and Ari unpack the powerful role of intuition in building lasting relationships with financial advisors, business partners, and even loved ones.They explain how what we call a gut feeling is actually condensed pattern recognition, your brain quietly scanning countless experiences to guide your decisions before you can put words to it. This is why many Root clients engage with our content for months before reaching out. They are building trust, alignment, and confidence long before the first conversation....
2025-09-1818 minRoot ReadyFrame It Right: A Simple Shift That Changes Client BehaviorHave you ever had a client who was financially ready to retire but just couldn't pull the trigger? They keep working, chasing one more bonus, one more year of 401(k) contributions, watching their financial projections climb higher while their actual life satisfaction stagnates.Listen as James unpacks what makes someone financially ready to retire, but emotionally stuck. In this episode of Root Ready, he shares with you why so many people keep working long after the numbers say they can retire.Drawing from Sahil Bloom’s "Five Types of Wealth" framework, James explains why money is...
2025-09-1711 minRoot ReadyGetting Clients to Open Up: A Framework for Financial AdvisorsAdvisors often face a gap between what clients ask for and what they truly need. Retirement projections and tax strategies are important, but beneath them is a deeper desire for clarity, purpose, and a meaningful life.In this episode of Root Ready, James shares a framework that builds trust and guides conversations beyond the numbers. Research shows people view their future selves like strangers, which makes long-term decisions difficult. Reframing choices through the question “What would my 86-year-old self advise?” brings sharper perspective.With practical questions and strategies, advisors can help clients reduce future regrets and...
2025-09-0324 minRoot ReadyHow Great Advisors Help Clients Face the Fear of RetirementSome clients are more than financially ready to retire, but still can’t bring themselves to do it. The real issue often isn’t the numbers. It’s the fear of losing identity, structure, and purpose after decades of work.In this episode of Root Ready, James explores how to support clients who feel stuck at the edge of retirement—not because they can’t afford to step away, but because they’re unsure who they’ll be when they do. Drawing on Viktor Frankl’s work on meaning and Riley Moynes’ four phases of retirement, the conversation dives...
2025-07-2325 minRoot ReadyWant to Be a Better Advisor? Learn to Frame Wealth the Right WayWhat if real wealth goes beyond money?In this episode of Root Ready, Harry Sommers joins James for a thoughtful conversation on redefining wealth—not just for clients, but for ourselves as advisors. Together, they explore a more expansive framework of financial planning that considers time, energy, relationships, and purpose.This isn’t about chasing higher balances. It’s about aligning resources with what matters most. Through real client stories and behavioral insights, Harry and James reflect on how emotional sensitivity, trust, and patience lead to the breakthroughs that truly move the needle.If you...
2025-07-0926 min