"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 stability
• How founder narratives create unnecessary pressure
• Why rest periods are essential for sustainable growth
• Finding confidence in your own definition of success

For anyone who's ever wondered if they're "hungry enough" as an entrepreneur or felt guilty for prioritizing life outside their business, this episode will help!

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.

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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. Discover practical steps toward becoming "dad by default" instead of "working by default."

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.

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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 vision while building a venture-scale company.

Whether you're currently fundraising or not, this episode offers valuable insights about how to interpret and work with your protective instincts as a founder.

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.

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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 challenges
• Why self-doubt might be a signal you're on the right track
• Moving beyond the "not doing enough" trap
• Finding peace with imperfect action while staying committed
• The surprising power of living in uncomfortable questions
• What real courage looks like in mission-driven work

Whether you're fighting for environmental justice, building something meaningful, or simply trying to do good work in a world that feels like it's burning, this conversation offers a powerful perspective on what it means to make real change. It challenges conventional wisdom about impact and invites us to consider that the very tension we're trying to resolve might be exactly what we need.

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.

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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 internal ceiling around $300K - exactly what his family needs to thrive. Through our exploration, we discover how childhood experiences with abandonment and conflict show up in surprising ways in our business decisions.

Themes we explore:

• The hidden psychology behind marketing resistance
• How childhood money stories impact adult business decisions
• Breaking through internal income ceilings
• Finding authentic ways to grow without compromising values
• The relationship between fear of abandonment and business growth

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.

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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 relationship between perfectionism and fear
• How over-analysis can mask deeper emotional needs
• Finding balance between achievement and self-trust
• Transforming your relationship with uncertainty
• Making decisions from a place of clarity rather than anxiety

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.

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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.

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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.

Chapters
7:10 Navigating Time and Alignment in Work
10:51 Exploring Authenticity and Meaningful Connections
20:21 Navigating Expectations and Authenticity in Business
39:50 Allowing Fear and Anger
46:57 The Power of Language and Self-Compassion

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
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