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

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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.

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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 uncertainty to our benefit.

Watch this session on YouTube

Find Troy on Linkedin
Troy's company Guide

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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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. Nurture in Entrepreneurship
- Managing Impressions and Internal Pressures
- Adaptive vs. Maladaptive Coping Strategies
- The Role of Early Family Dynamics

You can watch the episode on YouTube here

Where to find Laura:

• Website
• Instagram
• Linkedin

Resources Mentioned:

• Tools for Founders Project
• Pilea

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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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 trust potential teammates. And we discover how success doesn't have to come at the expense of authenticity but in fact, relies on it.

Watch this session 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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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 this coaching session with Olga Chin, founder and CEO of Interprice Technologies. Enjoy!

Watch this entire session 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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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 touch all this in a space that feels more like a meditation than a conventional coaching conversation. Enjoy!

You can watch the full video on YouTube.

Find Scott on:

• Substack
• YouTube
• X/Twitter
• Linkedin

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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• Email Brian at brian@dashingleadership.com
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