The Above Board Podcast

In this episode, we sit down with Jess Jensen, founder of Co-Pilot Communications, to talk about building authentic leadership in a digital world. After nearly 20 years inside Fortune 100 companies like Microsoft and Qualcomm, Jess now helps executives and founders find their voice, clarify their message, and show up online in a way that actually reflects who they are. We unpack why differences sell, how vulnerability builds credib...

Most financial mistakes aren’t math problems… they’re mindset problems. In this episode, John unpacks why knowledge alone isn’t what holds most people back. It’s not that you don’t understand budgeting, investing, or saving. It’s the emotions, habits, fears, and stories underneath your decisions that quietly drive the outcome. We talk about behavior vs. strategy, why self-awareness matters more than spreadsheets, and how to start m...

John sits down with Pia to explore the connection between creativity, conviction, and living with purpose. They talk about what it means to create from a place of clarity, how culture shapes expression, and the courage it takes to live authentically. It’s a thoughtful conversation about identity, purpose, and using your creativity in a way that reflects who you truly are.

Resources from Pia and the Kollectiv Studio:

Learn More abou...

Most money stress isn’t about income, it’s about how money flows.

In this episode, John Kennedy, CFP® breaks down the difference between spending up and spending down, why budgeting often feels frustrating, and how small system changes can create real clarity. He shares a simple framework for managing cash flow and building habits that actually stick. If you’ve ever felt like you’re earning enough but still wondering where your mon...

In this episode, John talks with Mitchell Osmond, founder of Dad Nation and host of The Dad Nation Podcast, about why success at work may not always translate to fulfillment at home. Mitchell shares practical takeaways for high-performing men who feel driven and capable, but disconnected in their relationships. It’s a grounded conversation about emotional presence, intentional leadership at home, and building real connection where ...

John shares a simple moment that turned into a bigger lesson about growth, patience, and showing up when things don’t go perfectly. Using an everyday experience, he reflects on how frustration, mistakes, and missed expectations are often part of the learning process, and not signs to quit. It’s a reminder that progress is built through consistency, resets, and staying present, even when things feel messy!

• 00:08 A Game of Catch...

In this episode, John sits down with Estate Planning & Probate Attorney, Jennifer Bondy, to talk about the often-overlooked emotional side of money, relationships, and decision-making. Jennifer shares how our past experiences shape the way we show up financially and personally, and why awareness is the first step toward real change. It’s an honest conversation about growth, clarity, and building healthier patterns that actually...

Before you start setting goals for the year, this episode takes a step back. John talks about why goal-setting often feels exhausting, not because you’re bad at it, but because you’re overloaded, and why creating space matters more than creating a perfect plan. He shares a simple but powerful approach to slowing down, getting clear on what you actually want your days to feel like, and building goals that support your life instead o...

This episode is our version of a year-end wrap. We look back on the biggest themes from 2025, from money and markets to mindset, purpose, and growth, and reflect on what actually mattered most. It’s a highlight reel of the conversations that shaped the year, plus a look ahead at what’s coming next. If you’ve been with us all year (or you’re just jumping in), this one ties it all together. Thanks for spending this year with us!

Pa...

In this episode, John sits down with CandorPath's newest advisor, Brandon Hatcher, to talk about purpose, passion, and what fulfillment really looks like; long before and long after retirement. Brandon shares his journey to CandorPath, why knowing someone’s “why” matters, and how money can simply fuel the life you want to live. They also touch on family, coaching, community, and how to stay grounded in your identity as seasons chan...

John sits down with mental health coach, author, and speaker Judith Belmont to unpack why our thoughts shape so much of how we feel, and what we can actually do about it. Judy breaks down Cognitive Behavioral Therapy (CBT) in a practical, down-to-earth way, from spotting cognitive distortions to managing anxiety, reframing stress, and building real resilience.

It’s an encouraging conversation about self-talk, self-worth, and learni...

Retirement isn’t the finish line... it’s the start of a new financial chapter. In this episode, John explains why shifting from “getting to retirement” to “planning through retirement” is essential. He shares real examples, the impact of staying invested, and what long-term risk actually looks like for retirees. A clear, practical conversation to help you protect your lifestyle, keep your money working, and stay confident for the d...

John and Rich dive into the hard but necessary work of setting boundaries, letting go of people-pleasing, and choosing peace over approval. They talk about recognizing one-sided relationships, protecting your energy, and why saying “no” is actually an act of self-respect. A practical, honest conversation for anyone feeling stretched thin or ready for a reset.

Rich also shares highlights from his new free mini-guide, The Fulfillment...

In this episode of The Above Board Podcast, John talks with Shellee Howard, college planning expert, founder of College Ready, and author of How to Send Your Student to College Without Losing Your Mind or Your Money. Shellee shares how families can navigate the college process with confidence by finding the right school, minimizing debt, and making smart decisions from start to finish. Whether your student is a freshman or a senior...

In this episode of The Above Board Podcast, John talks with Brian Ahearn, Chief Influence Officer at Influence People and one of the few globally certified trainers of Dr. Robert Cialdini’s principles of persuasion.

Brian shares ideas from his new book, Influence from Above: Where Faith and Influence Meet, exploring how persuasion, ethics, and love come together in leadership and life. They discuss how to lead with integrity, build...

In this episode of The Above Board Podcast, John Kennedy sits down with Eliana Goldstein, a certified career coach who helps ambitious professionals build careers they love without burning out. Eliana shares her own journey from corporate ad tech to coaching, what she’s learned about finding purpose at work, and why true fulfillment comes from alignment, not a job title. They also talk about burnout, confidence, and how to know whe...

We often talk about compound interest when it comes to money, but character works the same way. The small choices you make every day, how you lead, how you treat people, how you show up, build on each other over time. In this episode, John Kennedy, CFP®, shares how integrity, consistency, and humility play a bigger role in success than most people realize. It’s an honest look at how character compounds in business, leadership, and ...

In this week’s episode, John Kennedy shares why “getting in over your head” might be exactly what you need to grow in your career, your finances, or your personal life. He breaks down a powerful idea inspired by Carl Richards: real progress happens just beyond the edge of your comfort zone. Whether it’s taking on a new challenge, saying yes before you feel ready, or finally stepping into something that scares you a little. This epi...

In this episode, John chats with his longtime friend Kimberly Stevens—national champion swimmer, bestselling author, speaker, and breast cancer survivor. Kim has faced heartbreaking loss, her daughter’s life-threatening diagnosis, and her own battle with cancer. Instead of letting those moments define her, she turned them into a mission to bring hope to others through her movement Extend the Rose. We talk about resilience, grit, gr...