Have you ever wondered why certain types of people trigger you? Or why you keep attracting the same challenging dynamics with your team? In this deeply personal episode, I share my experience at an Art of Accomplishment retreat that revealed how childhood projections have been unconsciously shaping my life for decades. What You'll Learn: The concept of psychological projections and how they influence our inner stateHow childhood beliefs become self-fulfilling prophecies in business Why e...

When does structure become a cage? In this coaching session, entrepreneur Ryan Estes explores: The tension between productivity systems and creative spontaneityHow success can disconnect us from original passionsThe walls we build that eventually imprison usFinding harmony between responsibility and authentic expressionFor founders feeling successful but unfulfilled, this episode offers a framework for reconnection with what once sparked your entrepreneurial journey. Enjoyed this episode? Rea...

"Am I failing as a founder if I'm not constantly pushing for more growth?" After achieving stability in his 5-year-old business, Will Pearson brings this question to our coaching session. With a 4-year-old daughter and 7-month-old son at home, Will has found a balance between work and family, but feels guilty about it. This episode explores: The identity crisis that comes with business stabilityHow founder narratives create unnecessary pressureWhy rest periods are essential for sustainable gr...

Jason Shafton, founder and CEO of Winston Francois, wrestles with the challenge every entrepreneur-parent knows too well: how to build a thriving business while being fully present for family. After experiencing a profound personal loss, Jason's perspective on work transformed, yet he still struggles with the "always on" mentality. In this coaching session, we explore how perfectionism and the need to be needed keep notifications perpetually active, preventing true presence anywhere. Di...

When is your protective instinct trying to tell you something important? In this coaching session, an experienced founder shares their internal struggle with fundraising - not because they can't raise money, but because something deeper is holding them back.We uncover how past experiences of loss and betrayal shape our present choices, and how what feels like resistance might actually be wisdom. This conversation opens up crucial questions about control, growth, and staying true to your visio...

When climate guide and leadership coach Dom Francks steps into the coaching seat himself, he confronts a question that haunts many mission-driven leaders: what if all our work isn't enough? Through raw honesty about his own struggles with helplessness, self-doubt, and the unbearable gap between what he dreams of doing and what feels possible, Dom discovers an unexpected truth about impact.In this session, we explore:The tension between personal impact and planetary challengesWhy self-doubt mi...

When is the last time you felt completely stuck growing your business, knowing what you "should" do but feeling unable to do it? In this coaching session, successful founder David Spinks opens up about his struggle with traditional marketing after his startup exit. What starts as a conversation about business development quickly reveals deeper truths about money, authenticity, and the fears that hold us back.David sold his company CMX and stepped into coaching, only to find himself hitting an...

Does every decision feel like it needs a spreadsheet? In this coaching session, startup leader Nina Iordanova explores the hidden reasons behind her compulsive need to analyze and justify every choice.Together we uncover how her drive for achievement masks a deeper fear - one that many high performers share but rarely discuss. Nina discovers that her analytical habits aren't just about making good decisions; they're a shield against vulnerability and potential rejection.Key themes:• The relat...

Today is a solo episode where I get meta with the show and reflect on its origins, share some lessons learned, and process a bit about what might be next. Enjoy! Watch this episode on YouTube Enjoyed this episode? Ready to take your leadership and personal growth to the next level? Please visit my website to learn more about coaching with me. Subscribe on iTunes Visit my website Email Brian at brian@dashingleadership.com Follow Brian on YouTube Connect with Brian on Linkedin Follow Bria...

Cristina Poindexter is a serial entrepreneur who finds herself wondering how to make a new move in her career without burning out. She's no stranger to ambition - she's founded 2 companies and has worked at places like Google and Headspace. After leaving her last venture, she fears not being able to achieve her potential while being her authentic self.Watch as we explore what happens when we allow her fear to show up and express itself right in the session. Chapters7:10 Navigating Time a...

Troy Sultan is the CEO of Guide and he's been leading startups for a decade. This far into the journey, he finds he's been losing motivation and he came for a session to figure out why. Is it a temporary blip or is there something deeper going on? Confronting this question is no easy feat - no founder wants to admit that they feel disconnected from their company. But as the saying goes, the only way out is through. Together, we explore what happens how we can embrace doubt and uncertain...

In recognition of Mental Health Awareness Month, I speak with Laura Shook Guzman, a seasoned therapist and leadership coach, to explore prevalent mental health issues among entrepreneurs. This episode delves into the pressures founders face, discussing the balance between business demands and personal well-being, and highlighting strategies for managing mental health effectively.Key Points- The Most Common Mental Health Challenges Among Founders- The Importance of Self-Care- Nature vs. Nurtur...

Part of a founder’s job is to recruit the right people to your team. But how do you handle a situation where someone seems great on paper, but triggers a gut feeling that something is off? How do you stay authentic in a way that fosters trust with others? And what does a past experience of betrayal have to do with all this? These are the questions that Lauren Tracy brings to our coaching session. Together, we explore how her self-doubt is impacting her current venture and her ability to...

Part of a founder's job is to care more about the business than anybody else. That alone can bring a lot of intensity to work. But when you're an ex-banker to boot, things can get into overdrive. How do you make sure you don't burn out your employees that way, especially if they're not used to the pace? How do you trust your team to regulate their own work while maintaining a rapid pace? And how can a leader harness the power of "why" to resolve all this?These are the questions we get into in...

Scott Britton founded and sold his company to Salesforce in 2022. Nowadays he spends much of his time exploring the nature of human consciousness through writing and podcasting. And while he'd like to make a living from this some day, he's not sure that he can.Our session goes straight to the tension that many people face: whether one can support themselves through their passion. The tension brings up all sorts of questions of confidence, authentic desire, and self-trust in uncertainty. We to...

Ever found yourself glued to your phone, oblivious to a loved one's story about their day? Or felt guilty for focusing on work when you just want to enjoy time with family? Eric Bahn, co-founder of Hustle Fund, joined me to explore the struggle many of us face: turning off our work brains and being fully present with loved ones. We explore questions like...What prevents us from putting work aside?What does it mean to be a good parent?How do we escape unsatisfying feedback loops?Watch the...

Founders that embark on a fundraise are often met with a mix of electrifying hope and gnawing doubts. In my coaching session with Nestor Solari, CEO of Sigo Seguros, we tap into that dichotomy, revealing the raw emotional journey founders undergo while chasing startup funding. When you're in full on pitch mode, skepticism and pushback can throw you off your game. The negative emotions and stories that turn up are to be expected, but how we relate to them is what makes all the difference in ou...

Are you grappling with how to drive your team forward without coming off as a jerk? How do you balance accountability with empathy? In this coaching session, I go deep with Erik Dunteman, CEO and co-founder of Banana, as we tackle these burning questions. The journey into leadership isn’t just about strategies; it’s an invitation to confront our fears, embrace vulnerability, and overcome the inner barriers that hold us back.Erik opens up about his struggle to shift from doing to leading, his ...

In this episode, Brian coaches Jordan Taylor, CEO of Medley, as she navigates a pervasive leadership challenge: how to effectively manage her time amidst an endless sea of urgent tasks. The heart of this session lies in Jordan's moment of self-discovery, where she confronts the inner narratives that influence her leadership, offering a moment of clarity that could resonate with your own leadership journey.If you're a leader who finds yourself juggling between immediate needs and strategic goa...

In this episode, we delve into the emotional and professional crossroads faced by Danielle Lumetta, a founder grappling with the painful decision to shut down her company. Our session offers a rare window into the internal struggles and realizations that come with such a pivotal moment in an entrepreneur's journey. Danielle candidly shares her anxieties about disentangling her self-worth from her business success and the fear of repeating past mistakes in future endeavors. We explore the them...