How Enjoyment (Not Hustle) Drives Real Growth
7 Inner Shifts That Make You a Better Leader (Without Forcing It)
✅ Are you bootstrapping? You need this:
https://bootstrappedgiants.com/subscribe
✅ Master the Inner Game of Entrepreneurship here:
https://www.davekashen.com/newsletter-sign-up
00:00 – Intro: Dave’s coaching lineage + the Groundbreakers retreat
01:30 – Why even high-performing founders need constant inner work
03:00 – Dave’s perspective on “problems” vs. learning patterns
04:30 – First breakthrough: befriending the voice in your head
06:30 – How feelings unlock clarity (not block it)
08:00 – Why exercises over just insights in personal growth
09:30 – “Unfelt feelings are the glue” – Tara’s insight on stuck patterns
11:00 – Dave’s top takeaways from Joe Hudson’s Masterclass
12:30 – The 7 core mindset shifts explained:
15:30 – Real-life sales example: Jesse on objections and trust
18:30 – Dave’s “motorboat vs. sailboat” analogy for leadership energy
21:00 – Kids, walking, and letting life flow (vs. over-managing)
23:30 – Enjoying even hard tasks (like taxes!)
25:00 – Tactical tip: open your heart to feel more joy now
27:00 – Emotional decision-making vs. rationalization
29:30 – Spouse fights, ice cream, and clarity after feeling
32:00 – Jesse’s Growth Assistant story: AI direction driven by want
34:00 – How trusting your team’s authentic wants creates better outcomes
36:00 – Radical idea: you don’t need to improve to grow
38:30 – What you’d have to give up to feel peace without improving
40:30 – The power of authenticity, empowerment, and openness
42:30 – Final thoughts and reflections
What You’ll Learn:
In this powerful episode, Jesse and Dave go deep into the 7 mindset shifts from Joe Hudson’s Art of Accomplishment masterclass—principles that can radically reshape how you lead, decide, grow, and relate to others.
Whether you’re burned out from over-managing, stuck in self-improvement loops, or craving more ease in your entrepreneurial journey, this conversation offers a grounded, embodied approach to leadership and growth.
You’ll learn:
✅ Are you bootstrapping? You need this:
https://bootstrappedgiants.com/subscribe
✅ Master the Inner Game of Entrepreneurship here:
https://www.davekashen.com/newsletter-sign-up
00:00 – Intro: Dave’s coaching lineage + the Groundbreakers retreat
01:30 – Why even high-performing founders need constant inner work
03:00 – Dave’s perspective on “problems” vs. learning patterns
04:30 – First breakthrough: befriending the voice in your head
06:30 – How feelings unlock clarity (not block it)
08:00 – Why exercises over just insights in personal growth
09:30 – “Unfelt feelings are the glue” – Tara’s insight on stuck patterns
11:00 – Dave’s top takeaways from Joe Hudson’s Masterclass
12:30 – The 7 core mindset shifts explained:
15:30 – Real-life sales example: Jesse on objections and trust
18:30 – Dave’s “motorboat vs. sailboat” analogy for leadership energy
21:00 – Kids, walking, and letting life flow (vs. over-managing)
23:30 – Enjoying even hard tasks (like taxes!)
25:00 – Tactical tip: open your heart to feel more joy now
27:00 – Emotional decision-making vs. rationalization
29:30 – Spouse fights, ice cream, and clarity after feeling
32:00 – Jesse’s Growth Assistant story: AI direction driven by want
34:00 – How trusting your team’s authentic wants creates better outcomes
36:00 – Radical idea: you don’t need to improve to grow
38:30 – What you’d have to give up to feel peace without improving
40:30 – The power of authenticity, empowerment, and openness
42:30 – Final thoughts and reflections
What You’ll Learn:
In this powerful episode, Jesse and Dave go deep into the 7 mindset shifts from Joe Hudson’s Art of Accomplishment masterclass—principles that can radically reshape how you lead, decide, grow, and relate to others.
Whether you’re burned out from over-managing, stuck in self-improvement loops, or craving more ease in your entrepreneurial journey, this conversation offers a grounded, embodied approach to leadership and growth.
You’ll learn:
- Why connection and enjoyment matter more than perfection
- How to feel your way to clarity instead of forcing decisions
- How embracing your wants leads to better alignment and motivation
- Why authenticity drives more sustainable improvement than discipline
- The secret to empowering others (and yourself)
- How to lead with love, not defense
This episode of Heart of Entrepreneurship is a masterclass in founder mindset transformation. Drawing from Joe Hudson’s Art of Accomplishment, Jesse and Dave unpack how to lead from a place of presence, authenticity, and emotional intelligence—rather than fear, pressure, or performance.
They explore core principles like “Enjoy over Manage” and “Connection over Perfection,” using real-life examples from sales, coaching, and company building. You’ll hear how emotional awareness, internal alignment, and letting go of control can actually make you more effective—and more fulfilled.
Whether you're deep into self-awareness practices, building a startup, or leading a team, these mindset shifts will challenge and inspire you.
Like this episode? Comment with the shift that resonated most with you. Don’t forget to hit like and subscribe for more grounded conversations on growth and leadership.
#foundermindset #emotionalintelligence #leadershipskills
They explore core principles like “Enjoy over Manage” and “Connection over Perfection,” using real-life examples from sales, coaching, and company building. You’ll hear how emotional awareness, internal alignment, and letting go of control can actually make you more effective—and more fulfilled.
Whether you're deep into self-awareness practices, building a startup, or leading a team, these mindset shifts will challenge and inspire you.
Like this episode? Comment with the shift that resonated most with you. Don’t forget to hit like and subscribe for more grounded conversations on growth and leadership.
#foundermindset #emotionalintelligence #leadershipskills
