What if the key to better leadership, connection, and confidence came down to how you ASK questions? In this episode, I sit down with legendary interviewer and storytelling icon Cal Fussman. He’s spent decades in conversations with the world’s most influential people, including Muhammad Ali and Jeff Bezos. We talk about the power of curiosity, why asking great questions builds certainty, and how to navigate your life and business through deep listening. Cal also shares the life-changing lessons he’s learned from sitting down with the best and how you can use them to lead with purpose and impact. Get ready to rethink how you show up, how you connect, and how you lead!

In This Episode, You Will Learn

00:00 How to repackage your VALUE with confidence.

07:30 How to write emails that convert.

13:30 The mindset Cal used to connect with global icons.

22:45 What is the fastest way to monetize trust into revenue?

26:45 How to lead pricing conversations without fear or guilt.

35:30 Why your lowest-paying clients often demand the most.

42:30 Why giving fewer options creates more action and better sales.

50:00 The pitch strategy that gets decision-makers to say YES.

Resources + Links

Listen to Cal’s podcast ⁠Big Questions⁠

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

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Heather on Instagram & LinkedIn

What if your leadership style could become your greatest legacy? In this episode, I sit down with leadership expert and keynote speaker Jim Knight to talk about what it really takes to build culture, develop rockstar teams, and lead with passion. Jim shares how he went from Gatorland and Olive Garden to training at Hard Rock Café and speaking on stages around the world. I also talk about what it looked like to show up on stage while navigating one of the hardest moments of my life, how I managed to cancel high-profile meetings, honor my son’s grief, and still deliver a high-stakes keynote that same week. Plus, I also answer your DMs about fast business pivots, launching with confidence, and MORE.

In This Episode, You Will Learn

00:00 How I supported my son through his first experience with grief.

08:00 The BTS of delivering a keynote while managing emotional pain.

15:30 How did you start in the service industry?

25:30 Why “edutainment” is the future of speaking.

33:00 Jim’s 4 core leadership principles you can implement today.

41:30 What to do if you're working with a toxic CEO.

47:00 Advice for anyone who lost their job during COVID.

51:00 How to reinvent your business fast.

59:00 What happens when you bet on yourself?

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

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Heather on Instagram & LinkedIn

I’m doing something different this week! I’m bringing back the most powerful mic drop moments from three of my favorite solo episodes. In this episode, I talk about how I dealt with a massive challenge that cost me thousands, what happened when I realized I was being blocked from a seat at the table, and the lesson I learned at 5 AM when I finally asked for help. This is your reminder that you’re allowed to start messy, invest in yourself, get uncomfortable, and ask for support. 

In This Episode, You Will Learn

What to do when you’re being blocked.

The question I asked myself when everything felt overwhelming.

Why asking for help isn’t weakness.

The exact moment I stopped waiting for permission and pitched myself.

The mindset shift that helped me stop doing it all alone.

Resources + Links

Join the Elite Mastermind HERE

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Did you know that 80% of people don’t know how to identify their feelings? In this episode, I sit down with Michelle Chalfant, licensed therapist, holistic coach, and creator of The Adult Chair model. She talks about the real root of your triggers, why most people don’t know how to set boundaries, and how your subconscious programming shapes everything from your romantic relationships to your leadership style. We dive into a powerful inner child process LIVE on this episode to break down how unhealed wounds show up in everyday life and tangible ways to rewire them. Get ready to feel seen, heard, and validated into the MOST emotionally FREE version of YOU. Remember, your emotions are not a weakness—they're YOUR superpower.

In This Episode, You Will Learn

00:00 Why were most of us never taught how to set healthy boundaries?

07:00 How childhood modeling impacts your adult emotional patterns.

12:15 What your emotional triggers are actually trying to show you.

17:00 The unconscious belief systems formed before age 6.

24:30 How to reconnect with your inner child to heal abandonment.

29:00 LIVE demonstration of healing the “fear of being left”.

35:00 Why are romantic relationships the biggest mirror for your emotional wounds?

38:45 How reparenting your inner child transforms your confidence and relationships.

44:45 What to do when someone resists your new boundaries.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Michelle on Instagram & LinkedIn

If you’ve ever felt lost after a setback or unsure how to pivot into your next big chapter, this one’s for you. I’m sitting down with Steve Herz—talent agent, career coach, author, and a master at reinvention—to talk about how getting rejected from a dream job led him to build one of the most successful careers in media and personal development. From taking the calls no one else wanted, to turning soft skills into leadership superpowers, Steve breaks down the communication tools that actually move the needle (hint: it’s not your résumé). This episode is a masterclass in turning “no” into your greatest opportunity—and creating a life and career on your terms.

In This Episode You Will Learn

Rejection can redirect you toward your most aligned success path.

Soft skills matter more than technical skills for advancement.

Build influence through authority, warmth, and energy (AWE).

Confidence grows when you take uncomfortable but strategic action.

Culture transformation starts with effective private communication.

Don’t wait—reinvent, reach out, and create new opportunities.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

If you’ve ever felt like dating is one giant mystery while every other area of your life has a strategy—this episode is your game-changer. I’m joined by dating strategist Ben Hart, and we’re breaking down how to stop sitting on the sidelines and start approaching your love life with the same intention, confidence, and momentum you bring to your career. From how to stop overthinking early dating stages to setting standards without pushing love away, this conversation will help you flip the script on dating and attract the kind of relationship you actually want. 

In This Episode You Will Learn

Dating requires intention, just like any other life goals.

The small confidence-building steps that matter more than grand gestures.

Why creating fictional narratives is killing your relationships.

Practical tips for flirting and navigating the early stages of a new relationship.

Stop treating dating as a transaction, enjoy the process and yourself.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Ben on Instagram

If you’ve ever felt like self-doubt is slowing you down or wondered how the most successful people keep showing up with grit, resilience, and fun—this episode is for you. I had the honor of sitting down with power couple Sarah Blakely and Jesse Itzler for a live conversation that will completely shift the way you think about mindset, momentum, failure, and chasing your dreams your way. From Spanx to ultra-marathons, reality TV to billion-dollar exits, this one is packed with real talk, hilarious stories, and life-changing insights on how to create confidence that lasts.

In This Episode You Will Learn

How to spot and protect your billion dollar idea.

How to build momentum (that leads to unstoppable success.)

The direct connection between your mindset and how far you’ll go.

2 ways to create deeper customer connection.

Your “why” sells more than your “what.”

Be different—your uniqueness is your biggest business asset.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Want to know how the most unapologetically confident think? I’m bringing back my episode with the one and only, Gary Vee. He shares incredible insights about chasing your dreams, why success isn't about money but about happiness, and how to stay true to yourself in a world full of noise. We talk parenting, entrepreneurship, and how to turn your passion into your purpose - with zero excuses. If you're ready to be inspired, challenged, and motivated to level up your life, this episode is going to light a fire under you that you won't forget! 

In This Episode You Will Learn

Why most parents are raising entitled kids (and how to actually set them up for success.)

Gary’s formula for leadership, personal growth, and emotional freedom.

What to do when your passion doesn’t match traditional success.

How to negotiate your salary with confidence.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Gary on Instragrm: @garyvee

You are the ONE your family legacy has been waiting for! In this special replay, I’m joined by entrepreneur, speaker, and best-selling author Justin Prince to talk about how perseverance, faith, identity, and vision all work together to shape your unforgettable life. He shares how he went from flipping pizzas and selling Bible videos to building five multimillion-dollar businesses and impacting millions. We also talk about how to unlock and achieve our greatest potential. Remember, YOU were made for more! 

In This Episode You Will Learn

Why your STRUGGLE is just as valuable as your dream.

The difference between being motivated by fear vs. stepping into purpose.

How to show up with energy even when you don’t “feel” ready.

The “E + R = O” formula to shift your mindset in hard moments.

What to do when your dream feels too fragile to share.

How to make decisions that shift the trajectory of your entire family legacy.

Resources + Links

Sign up for a one-dollar-per-month trial period at shopify.com/monahan

Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN.

Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN.

Get 10% off your first Mitopure order at timeline.com/CONFIDENCE.

Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com.

Call my digital clone at 201-897-2553! 

Visit heathermonahan.com

Sign up for my mailing list: heathermonahan.com/mailing-list/ 

Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com 

If you haven't yet, get my first book Confidence Creator

Follow

Heather on Instagram & LinkedIn

Justin on: