You can feel stuck in a successful career and still know it's not the life you want.

In this episode, we talk with Jacob Tally of Prospero Wealth about what it actually looks like to pivot later, especially after years in high-intensity environments like startups, corporate finance rotations, and big-name financial services.

Jacob shares the practical side of making the move: deciding between going solo or joining an independent RIA, why fee-only planning mattered to him, and how he evaluated firm fit before jumping.

We also get into planning for tech and startup employees, where equity compensation, job changes, and sudden life transitions create complexity that generic advice can't solve.

The most useful part is the decision framework. We dig into risk management beyond investing: pressure testing your situation, spotting blind spots, and using fear setting to turn vague anxiety into clear options. Jacob also challenges the obsession with goals, reframing growth around principles that keep you moving when life doesn't follow a neat timeline.

If you're considering a career change, building a financial plan, or trying to make a brave decision without guessing, this conversation gives you language and structure you can use right away.

Please subscribe, share, and leave a review. What decision are you trying to get clarity on right now?

Jacob's Social:

https://www.linkedin.com/in/jhtally/

Prospero Wealth website: 

https://prosperowealth.com/

Music in the episode was obtained from Bensound

Most financial advice is built around a default life plan — and it quietly breaks down when you've opted out of that script. Cory Smith is a fee-only financial life planner and founder of Discretionary Inc. in Reno, Nevada, where he works exclusively with childfree individuals, couples, and business owners who want their finances to support the life they actually want — not the one they were expected to want.

In this episode, we get into his core concept of discretion: the freedom to determine your own best course of action. We talk about what changes in planning when there are no assumed heirs, why longevity and support structures deserve more attention in this space, and how he works backward from a client's vision to build a financial framework around it.

Cory also shares the path that shaped his philosophy — from commission-driven environments and door knocking at Edward Jones to the fee-only model — and how he integrates George Kinder's Real Life Planning process into a modern client experience, including a concurrent planning approach that delivers early wins while the deeper work unfolds.

We also cover what's working in his business today: partnerships, community building, and using short-form and long-form content to reach people who are quietly rewriting the rules.

If you're interested in values-based planning and building a life on your own terms, this one's worth your time.

Cory's Social and Website

https://www.linkedin.com/in/dincwithcory/

https://www.discretionaryinc.com/

Ethan Miller had a six-month waitlist… while still working a full-time job.

We sat down with the founder of Planning for Progress to talk about how he went from union organizing to building a thriving fee-only firm just outside DC—without taking a reckless leap.

He shares how he found fee-only planning, built early momentum through project work, and knew commissions weren’t the path for him. We also get into what it actually looked like to earn his CFP while working nights and weekends—and the moment he knew it was time to go all in.

We also cover how he’s designed a lifestyle practice of ~50 households, how he thinks about client fit, and why being a “people person” can matter more than a finance background when starting out.

If you’re thinking about making the jump into financial planning, this is a grounded, real-world blueprint.

Ethan's Social:

https://www.linkedin.com/in/ethan-miller-cfp%C2%AE-41139430/

Music in this episode was obtained from Bensound.

He didn’t grow his RIA through ads or a content machine. He grew it through trust, a simple fee model, and doing the unglamorous work when it mattered most.

In this episode, we’re joined by Logan Valentine, CFP®, founder of Valentine Wealth Management in Seymour, Indiana. We unpack his path from insurance to Charles Schwab, how earning the CFP shifted his thinking, and what clicked when he discovered the fee-only RIA model.

We also talk about the reality of building a firm early on—tight runway, young family, and the mindset required to keep going when things feel uncertain.

Then we get practical. Logan breaks down his pricing structure, including a minimum fee and capped maximum, and explains why he avoids charging on held-away assets like 401(k)s and 529s. The result: fewer conflicts and a simpler, more transparent sales process.

On the marketing side, this isn’t about hacks. It’s about what actually works for most advisors—strong reputation, Google reviews, local presence, SEO, and creating long-term advocates by helping people whether they become clients or not. (At one point, someone even found him by asking AI who to call.)

We wrap with the client experience—from discovery to onboarding—why cash flow is the foundation of good planning, and how thoughtful tax decisions can lead to real, tangible savings.

If you’re building a firm—or looking for transparent, fee-only advice—there’s a lot here you can take and apply.

Logan's social and website:

https://www.linkedin.com/in/logan-valentine-cfp/

https://www.valentinewm.com/

Music in this episode was obtained from Bensound

One of the most uncomfortable questions in financial planning is also one of the most important: if you can’t speak for yourself, who will?

We’re joined by Maddy Roche, Chief Growth Officer at Childfree Trust and a long-time leader in the fee-only advisor community, to explore the planning gaps that often arise for clients who are child-free or permanently childless. This isn’t a niche situation—about one in four Americans doesn’t have kids, and that number is even higher among younger generations.

We discuss how a child-free lens can reshape a financial plan, from Monte Carlo projections and decumulation strategies to estate planning priorities and insurance needs. Maddy explains why life insurance may be less relevant for many in this group, while disability insurance, long-term care planning, and a clear medical power of attorney become even more important.

We also touch on the emotional side—the peace of mind that comes from having a professional, unbiased third party in place, rather than leaving difficult decisions to friends or distant relatives.

Maddy outlines what Childfree Trust offers nationwide, including serving as financial POA, medical POA, executor, or trustee, along with building detailed care plans covering everything from key contacts to pet care to end-of-life preferences.

For advisors, this conversation highlights the risks of overlooking these roles and documents—and how making the right referral can add meaningful value across your client base.

Subscribe for more conversations that make fee-only planning more practical. Share this with someone who needs a better backup plan

Maddy's Social and Childfree Trust Website

https://www.linkedin.com/in/maddy-roche-25962032/

https://childfreetrust.com/

Geoffrey Schaefer thought he’d work in finance. The Army had other plans.

After serving as a U.S. infantry officer, Geoffrey eventually found his way back to the industry—now as a fee-only fiduciary wealth advisor and partner at an independent firm serving families, retirees, and small business owners.

In this episode, we talk about starting out in a product-driven environment where the tools can be impressive, but the incentives can quietly shape the planning relationship. Geoffrey explains the long-term impact of production culture, why many clients end up with “an investment guy” instead of a real financial planner, and how the conversation changes when you can say the only people who pay you are the clients themselves.

We also go behind the scenes of running an advisory firm—partner dynamics, dividing responsibilities like compliance and investment management, outsourcing what doesn’t belong on an advisor’s desk, and building a multi-generational planning model that serves parents, kids, and grandkids through major life transitions.

Geoffrey closes with practical advice for newer advisors on humility, mentorship, and why earning the CFP early can make a real difference.

If you enjoy conversations with real planners about how this profession actually works, subscribe to the show, share the episode with a colleague, and leave a quick review so others can find it.

Geoff's Blog and Social:

https://thesteadfastfiduciary.com/

https://intergywealth.com/

https://www.linkedin.com/in/geoffrey-schaefer-intergy/

Music in this episode was obtained from Bensound

Two weeks before the shutdown, Dan Ryan left a big firm to launch Sinceris Advisory with a simple plan: stay virtual, serve clients deeply, and let great work drive growth. Then COVID hit. Meetings vanished, Zoom became standard, and he had to adapt fast.

Today, the firm manages $226M for 150 families. Dan shares the real story—cancelled deals, “tire kickers,” 80-hour onboarding weeks, and learning that referrals are the only growth channel that truly compounds.

We also talk about operations and hiring (most advisors wait too long), bringing on partner David Wilson in May 2020, and their decision to avoid client handoffs—protecting service quality even if it limits scale.

Dan works across tech equity comp and physician practices, which keeps the work engaging and prevents burnout. His advice to founders: it doesn’t get easier, but autonomy is worth it. Lead with compassion, set boundaries, and price sustainably.

Website: https://sincerusadv.com/

Music in this episode was obtained from Bensound.

Andy Fisher spent 25 years leading operations at a Fortune 500 company before launching Path Setter Financial, a fee-only RIA built on clarity, transparency, and calm.

In this episode, we talk about his transition from corporate leadership to advisory firm owner—and what engineering discipline taught him about building better financial planning processes.

We discuss how fee structures influence outcomes, why fiduciary advice truly changes the conversation, and how Andy structures discovery to help couples align spending with values. His philosophy is simple: the math is straightforward, but behavior drives results.

We also get into real advisor topics—navigating stock comp, pensions, and early retirement windows; launching an RIA; early operational mistakes; implementing a CRM; outsourcing strategically; and the role peer groups play in momentum and accountability.

If you’re building or refining your firm, this conversation offers practical insight into process design, client communication, and helping families move from analysis to action.

If you found it valuable, follow the show, share it with another advisor, and leave a quick review.

Andy's Social:

https://www.linkedin.com/in/andy-fisher-16522410/

Music from this episode was obtained through Bensound.

Meet the person you want on your side when policies get real. We sit down with Charles Priest, our new head of Property and Casualty at BC Brokerage, to unpack how a planning‑first mindset turns confusing coverage into clear, confident decisions for households and businesses. Charles brings 16 years of experience helping clients navigate tough choices, manage risk trade‑offs, and pick carriers that stand up when a claim lands—not just when a quote looks cheap.

We start with the basics that most people miss: why umbrella liability is a cornerstone of personal protection, how to right‑size auto and home limits, and the small tweaks that lower friction without raising exposure. For advisors, Charles lays out quick checks that surface red flags fast, from missing umbrellas to deductibles that don’t match cash reserves. Then we move to the commercial side where growth outpaces coverage, and cyber risk demands real defenses. Social engineering and ransomware aren’t fringe threats anymore; they’re everyday business hazards. Charles explains what good cyber insurance should fund—incident response, forensics, notification, restoration, and business interruption—and how to align limits with the data and dollars at stake.

We also dig into timing and markets. The ideal window to shop is roughly 60 days before renewal so we can clarify goals, work with underwriters, and tailor terms. Mid‑term updates can still deliver value with pro‑rated changes. Most of all, we challenge the myth of “apples to apples”: policy wording, exclusions, and claims handling vary widely, and the cheapest option can become the costliest mistake when it matters. If you’re an advisor seeking a smarter P&C partner or a client who wants fewer surprises and better outcomes, this conversation offers a clear path.

If you find this helpful, follow the show, share it with a colleague, and leave a quick review—what P&C question should we tackle next?

Why do some advisors thrive without managing assets? We talk with Kelly Nilsson, founder of Brava Financial, about building a planning-first, advice-only practice that focuses on real-life risk—not just market returns. With a background in insurance, Kelly believes households are more often disrupted by death, disability, or long-term care than by volatility, and her plans are built to handle those moments.

Kelly shares how she launched a virtual RIA, why project-based planning fuels her growth, and how clear scope, flat fees, and objective advice create better client outcomes. “Rent my brain” means no product pressure, no discounts, and clients who are ready to implement.

This episode covers practical ways to identify the right clients, use paid consults as discovery, and design services people actually understand. A must-listen for advisors questioning the AUM default and looking to build a sustainable, planning-led practice.

Kelly's Social:

https://www.linkedin.com/in/kellynilssoncfp/

Music in this episode was obtained from Bensound.