What separates entrepreneurs who keep struggling from those who learn, adapt, and eventually break through?

Persistence matters in entrepreneurship, but persistence alone isn't enough. Markets change, customers change, technology evolves, and sometimes the original plan simply isn't the right one.

In this episode of At the End of the Day, Chris Raimo sits down with James B. Hayden, a GTM strategist and fractional CRO with more than 30 years of experience fixing broken B2B sales engines. James has helped build and rebuild revenue teams at more than 140 companies, generating more than $1 billion in personal revenue throughout his career.

James shares lessons from decades of working alongside founders, CEOs, and sales teams, including stories of entrepreneurs who came close to losing everything but continued moving forward.

Chris and James explore the mindset behind entrepreneurship, the personal sacrifices that come with building a business, the importance of knowing your ideal customer, how AI is changing the way entrepreneurs work, and why documenting repeatable processes is essential for growth.

At the heart of their conversation is what James calls "enlightened persistence": staying committed to your goal while being willing to adapt your approach as circumstances change.

What You'll Learn

In this episode, you'll discover:

•  Why difficult seasons can sometimes mean you're closer to success than you realize 
•  The difference between persistence and enlightened persistence 
•  Why entrepreneurs often have a naturally low tolerance for being told "no" 
•  How rejection and difficult life experiences can become motivation 
•  Why gratitude and mindset influence the way you lead and sell 
•  The personal and family sacrifices that can come with entrepreneurship 
•  Why adaptability becomes increasingly important as markets and technology change 
•  How entrepreneurs can use AI as a practical business tool 
•  Why every business needs a clearly defined ideal customer profile 
•  How trusted advisors can expose weaknesses and blind spots 
•  Why documenting processes is essential for creating a scalable business 
•  How entrepreneurs can turn hustle into more predictable revenue 

Chapters

0:23 Chris introduces James B. Hayden

1:42 McCaw Cellular and why persistence matters

4:58 The "low compliance factor" and why entrepreneurs don't easily accept no

6:13 Adoption, rejection, and turning insecurity into fuel

8:05 Gratitude, mindset, and starting the day with perspective

10:10 Is entrepreneurship "wash, rinse, repeat"?

12:39 Family sacrifices and the personal cost of entrepreneurship

20:41 Advice for aspiring entrepreneurs preparing to start

21:22 Rapid change, opportunity, and the race car analogy

25:57 Building and refining your ideal customer profile

28:27 What entrepreneurs don't talk about enough

31:39 Creating repeatable, scalable processes and documenting what works

Connect with James B. Hayden

Website | James B. Hayden

LinkedIn | James B. Hayden | 27K+ followers

X (Twitter) | James B. Hayden

TikTok | James B. Hayden

Email: [email protected]

Phone/Text: 206-915-0458

Call to Action

Entrepreneurship isn't about having every answer before you begin. It's about learning, adapting, surrounding yourself with the right people, and continuing to move forward when the path changes.

If this episode gave you a new perspective on persistence, adaptability, sales, or building a scalable business, share it with another entrepreneur who needs to hear it.

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What happens when you're exceptional at your profession but have never been taught how to run a business?

Many entrepreneurs start with a passion for helping people, only to discover that running a successful business requires an entirely different skill set.

In this episode of At the End of the Day, Chris Raimo sits down with Patrick Eilers, licensed professional counselor and founder of BloomWorks Consulting. After nearly a decade working across the mental health field, Patrick recognized a major gap: therapists were being trained to care for clients, but not to lead businesses. The result? High staff turnover, unhealthy workplace cultures, and overwhelmed practice owners.

Patrick shares how he turned that problem into a consulting business dedicated to helping mental health practices build healthier cultures, stronger systems, and more sustainable businesses, while offering lessons every entrepreneur can apply, regardless of industry.

What You'll Learn in This Episode

•  Why being great at your profession doesn't automatically make you a great business owner 
•  The biggest challenges therapists face when transitioning into entrepreneurship 
•  How unhealthy company culture creates high employee turnover 
•  Why systems and operations are essential for scaling any business 
•  The importance of defining a clear vision before hiring your team 
•  How finding a niche can help you stand out in a crowded marketplace 
•  Why entrepreneurs often underestimate the emotional demands of building a business 
•  How AI helped Patrick develop new business frameworks 
•  Why success is measured by growth, not just revenue 
•  The value of mentors, coaches, and community when starting a business.

About Patrick Eilers

Patrick Eilers is a licensed professional counselor, consultant, and founder of BloomWorks Consulting. Since 2016, he has worked across the mental health field supporting individuals, couples, and groups through anxiety, depression, addiction recovery, and major life transitions.

Drawing on years of clinical experience, Patrick now helps mental health practice owners become stronger leaders by improving workplace culture, reducing clinician turnover, developing healthier teams, and creating systems that allow practices to grow sustainably. His passion lies in empowering healthcare professionals while building environments where both clinicians and clients can thrive.

Connect with Patrick Eilers

Website: https://www.patreon.com/bloomworks

LinkedIn: https://www.linkedin.com/in/patrickeilersbloomworkscc

Instagram: https://www.instagram.com/rated_pge

If this episode gave you a new perspective on entrepreneurship, leadership, and building a healthier business, share it with another entrepreneur who's ready to grow.

Connect with Chris Raimo on LinkedIn:

https://www.linkedin.com/in/chris-raimo-75b17a1b/

Follow the At the End of the Day Podcast on LinkedIn:

https://www.linkedin.com/showcase/at-the-end-of-the-day-podcast/posts/?feedView=all

Subscribe, leave a review, and follow the podcast for more conversations with entrepreneurs who share the lessons they've learned while building businesses that create lasting impact.

What does it really mean to take ownership of your life and your business?

Entrepreneurship isn't just about starting a business. It's about becoming fully responsible for your decisions, your mindset, and your results.

In this thought-provoking episode of At the End of the Day, Chris Raimo sits down with Walter Ruskin, sales leader, keynote speaker, coach, former actor, and comedian. Drawing from more than 30 years in high-performance sales, Walter shares a refreshingly honest perspective on accountability, leadership, personal responsibility, and the mindset required to thrive as an entrepreneur.

Filled with humor, philosophy, and practical wisdom, this conversation challenges conventional thinking and encourages aspiring entrepreneurs to look inward before building outward. 

What You'll Learn in This Episode

•  Why entrepreneurship begins with radical personal accountability 
•  The difference between being ready and the world being ready 
•  How self-awareness shapes better leadership and better business decisions 
•  Why honesty with yourself is harder than honesty with others 
•  The importance of creating a workplace culture built on responsibility instead of blame 
•  Lessons from over 30 years in sales and leadership 
•  How philosophy can help entrepreneurs make better decisions 
•  Why delegation never removes accountability 
•  The hidden dangers of avoiding difficult conversations 
•  How authenticity builds stronger relationships with customers and teams 
•  Why writing, walking, and thinking may be the most valuable business habits you can develop.

Key Takeaways

•  Success starts with taking full ownership of your actions and decisions. 
•  Delegation transfers responsibility for execution, not accountability. 
•  Entrepreneurs must become comfortable with uncertainty and change. 
•  Honest communication builds trust faster than perfection. 
•  Leadership isn't about assigning blame. It's about solving problems together. 
•  Self-reflection is one of the most valuable tools any entrepreneur can develop. 
•  Building a business starts with understanding yourself.

About Walter Ruskin

Walter Ruskin is a sales leader, keynote speaker, coach, and former actor and comedian who combines more than three decades of real-world sales experience with humor, philosophy, and practical leadership lessons. His engaging style makes complex ideas accessible while helping entrepreneurs and business leaders develop stronger accountability, communication, and personal responsibility.

Connect with Walter Ruskin

•  Website: https://bookwalterruskin.com
•  Email: [email protected]
•  Instagram: @walterunderpressure

If this episode challenged the way you think about leadership, accountability, and entrepreneurship, share it with someone who's building a business or considering taking the leap into entrepreneurship.

Connect with Chris Raimo on LinkedIn:

https://www.linkedin.com/in/chris-raimo-75b17a1b/

Follow the At the End of the Day Podcast on LinkedIn:

https://www.linkedin.com/showcase/at-the-end-of-the-day-podcast/posts/?feedView=all

Subscribe, leave a review, and follow the podcast for more conversations with entrepreneurs, founders, and business leaders sharing the lessons they've learned on the journey of building meaningful businesses and lives.

What if your biggest career setback is actually the beginning of your greatest opportunity?

Have you ever wondered if you're pursuing the wrong path?
 What if the career you've always dreamed of isn't the one you're meant to build?

In this episode of At the End of the Day, Chris Raimo sits down with Laura Berman Fortgang, one of the pioneers of the personal coaching industry. A five-time bestselling author, TEDx speaker, executive coach, and creator of the Now What?® career transition methodology, Laura shares how an acting career that didn't go as planned ultimately led her to build a thriving coaching business spanning more than three decades.

Together, they explore career transitions, entrepreneurship, resilience, mentorship, and what it really takes to build a business that aligns with the life you want. 

What You Will Learn in This Episode

•  How Laura transitioned from pursuing Broadway to becoming a pioneer in coaching 
•  Why thinking like an entrepreneur is different from simply being good at your craft 
•  The biggest mistakes new entrepreneurs make when starting a business 
•  Why building a sales pipeline matters more than hoping clients will find you 
•  The importance of delegation and focusing on your unique strengths 
•  How 9/11 unexpectedly transformed Laura's business and created her Now What?® methodology 
•  Why mentors and coaches accelerate entrepreneurial success 
•  The role of authenticity and visibility in today's business world 
•  How to become comfortable with failure and use it as fuel for growth 
•  Why designing your life first leads to better business decisions 

About Laura Berman Fortgang

Laura Berman Fortgang, MCC (Master Certified Coach), is recognized as one of the pioneers of the personal coaching profession. She is a five-time bestselling author whose books have been translated into thirteen languages, an award-winning author, sought-after keynote speaker, TEDx presenter with more than two million views, television personality, interfaith minister, and performer.

Best known for her Now What?® career transition methodology, Laura has spent more than 30 years helping individuals and entrepreneurs discover meaningful work, navigate career transitions, and build businesses that align with their purpose. She also mentors coaches through her A-List Coach program.

Connect with Laura Berman Fortgang

•  Website: https://laurabermanfortgang.com
•  LinkedIn: https://www.linkedin.com/in/laurabermanfortgang/
•  Instagram: https://www.instagram.com/laurabfortgang/

If this episode inspired you to rethink your career or entrepreneurial journey, share it with someone who's asking themselves, "Now what?"

Connect with Chris Raimo on LinkedIn:

https://www.linkedin.com/in/chris-raimo-75b17a1b/

Follow the At the End of the Day Podcast on LinkedIn:

https://www.linkedin.com/showcase/at-the-end-of-the-day-podcast/posts/?feedView=all

Subscribe, leave a review, and follow the podcast for more conversations with entrepreneurs and business leaders who share the lessons they've learned building meaningful businesses and lives.

What if the secret to growing your business isn't working harder?

What if scaling isn't about doing more, but doing less of the wrong things?

And how do you know what to automate, what to delegate, and what only you should be doing?

In this episode of At the End of the Day, Chris Raimo sits down with Le-an Lai Lacaba, serial entrepreneur, international speaker, author, certified AI consultant, and Co-Founder of 2xYou. Le-an shares her remarkable journey from landing her first freelance writing job at age 15 to building multiple businesses that help entrepreneurs scale through AI, executive assistants, and proven systems.

From surviving a devastating super typhoon in the Philippines to speaking on stages around the world, Le-an's story is a powerful reminder that entrepreneurship is as much about resilience and relationships as it is about strategy and growth. 

What You Will Learn in This Episode

•  How a life-changing experience inspired Le-an's entrepreneurial journey 
•  Why people are often the hardest and most important part of business 
•  The leadership lessons every entrepreneur must learn 
•  How AI is changing the future of entrepreneurship 
•  Why relationships and community matter more than ever 
•  The loneliness that many entrepreneurs experience behind the scenes 
•  The Scale You Formula and how it helps entrepreneurs grow 
•  How to identify what to automate, delegate, and eliminate 
•  Why systems are essential for scaling a business 
•  The mindset shifts required to become a successful entrepreneur

About Le-an Lai Lacaba

Le-an Lai Lacaba is a serial entrepreneur, international speaker, author, and certified AI consultant. As Co-Founder of 2xYou, a multi-awarded outsourcing company, she helps entrepreneurs scale through AI, expert executive assistants, and proven systems.

She is the creator of the Scale You Formula, host of the Scale You Podcast, author of Scale You, and a leading voice on outsourcing, remote work, AI, and entrepreneurship. Le-an has spoken in six countries and continues to help business owners build scalable businesses that give them more freedom and impact.

Connect with Le-an Lai Lacaba

•  LinkedIn: https://www.linkedin.com/in/leanlailacaba
•  Instagram: https://www.instagram.com/leanlailacaba
•  Facebook: https://www.facebook.com/leanlailacaba
•  Personal YouTube: https://www.youtube.com/leanlailacabaVA
•  Scale You YouTube: https://www.youtube.com/@scaleyouwithlean
•  TikTok: https://www.tiktok.com/@leanlailacaba

Scaling isn't about doing more. It's about understanding what only you can do, building systems around everything else, and creating a business that can grow without depending entirely on you.

If this episode gave you a new perspective on AI, outsourcing, and scaling your business, share it with a fellow entrepreneur who is trying to do everything themselves.

Connect with Chris Raimo on LinkedIn:
 Chris Raimo

Follow the podcast on LinkedIn:
 At the End of the Day Podcast

Follow At the End of the Day for more conversations with entrepreneurs, founders, and business leaders who share the lessons they've learned building businesses and creating meaningful impact.

What separates great leaders from overwhelmed managers?

Why do some businesses thrive while others struggle with burnout, turnover, and stalled growth?

And what can entrepreneurs learn from someone who spent 20 years leading in the United States Marine Corps?

In this episode of At the End of the Day, Chris Raimo sits down with Janet Polach, leadership strategist, executive coach, Marine Corps veteran, and founder of In the Lead. Drawing from her experience in the military, global consulting, and entrepreneurship, Janet shares practical lessons on leadership, delegation, decision-making, and building organizations that can grow beyond their founders.

Whether you're leading a team, starting a business, or navigating uncertainty, this conversation offers valuable insights on becoming a stronger and more strategic leader.

What You Will Learn in This Episode

•  How military leadership principles apply to entrepreneurship 
•  Why leaders often become the bottleneck in their own businesses 
•  The hidden cost of the "I alone can fix it" mindset 
•  How to delegate effectively and empower your team 
•  Why employee engagement starts with leadership 
•  How economic uncertainty impacts business decisions 
•  Why AI is creating new challenges for leaders 
•  The realities of entrepreneurship and the importance of resilience 
•  How to build a support system that helps you succeed 
•  Why strategic thinking becomes more important as businesses grow.

Key Takeaways

•  Great leaders focus on a few critical priorities rather than trying to do everything 
•  Delegation is essential for growth and long-term sustainability 
•  Employee retention often starts with effective leadership 
•  Services-based businesses can be easier to launch than product-based businesses 
•  Entrepreneurship can be lonely, making support systems essential 
•  Strategic leaders spend more time thinking ahead than reacting to problems 
•  Success requires both discipline and adaptability .

About Janet Polach

Janet Polach is a retired Marine Corps officer, executive coach, leadership strategist, and founder of In the Lead. After earning her PhD in Organizational Development and working with a global consulting firm in China, she launched her own consulting practice, helping hundreds of organizations worldwide improve leadership effectiveness, employee engagement, and business performance.

Drawing on her military leadership experience and decades of consulting work, Janet helps organizations reduce turnover, strengthen leadership teams, and create cultures where people and profits can thrive. Known for her no-nonsense yet lighthearted approach, she delivers practical strategies that create lasting results for leaders at every level.

She is also the author of The Strategic Leader's Mindset.

Connect with Janet Polach

•  Website: https://janetpolach.com/
•  Email: [email protected]
•  Free Strategic Leadership Assessment and chapter download available on her website.

If this episode changed the way you think about leadership and entrepreneurship, share it with a fellow entrepreneur, manager, or aspiring business owner.

Follow At the End of the Day for more conversations with entrepreneurs and business leaders who share the lessons they've learned building successful businesses and meaningful lives.

Connect with Chris Raimo on LinkedIn:
 Chris Raimo

Follow the podcast on LinkedIn:
 At the End of the Day Podcast LinkedIn Page

Subscribe, follow, and share the podcast to help more aspiring entrepreneurs learn from leaders who have built, scaled, and sustained successful businesses.

What if fear is the only thing standing between you and starting your business

Are you waiting until you feel confident enough
 Or is that fear quietly keeping you stuck where you are

In this episode of At the End of the Day, Chris Raimo sits down with Leesa Blankert, founder of LAB Online Agency, to talk about what really holds people back from starting their entrepreneurial journey. From layoffs to building her own agency, Leesa shares honest insights on fear, taking action, and why starting before you feel ready is often the only way forward.

What You Will Learn in This Episode

•  How fear shows up when starting a business 
•  Why most people delay their entrepreneurial journey 
•  How Leesa transitioned from traditional work into entrepreneurship 
•  The reality of building a digital agency from scratch 
•  The role of AI in business and why fundamentals still matter 
•  Why human connection remains a competitive advantage 
•  How community and networking can accelerate your growth 
•  Why rejection is part of the process and not something to fear 

About Leesa Blankert

Leesa Blankert is the founder of LAB Online Agency with a background in marketing and psychology. She works with small business owners to build effective marketing campaigns across web development, SEO, PPC, and digital strategy

Her journey into entrepreneurship was shaped by unexpected challenges, career shifts, and the decision to move forward despite uncertainty.

Connect with Leesa

•  Instagram: https://www.instagram.com/labagency.online/
  
  
•  LinkedIn: https://www.linkedin.com/in/leesa-blankert-7b1bb789/

If this episode helped you rethink what is holding you back share it with someone who is ready to start but still hesitating
 Follow the podcast for more real conversations about entrepreneurship and leave a review to help more people discover the show. 

What if that moment never comes
 And what if taking action before you feel ready is actually the advantage

In this episode of At the End of the Day, Chris Raimo sits down with Nathan Turner to break down what it really takes to start and grow a business. From franchising to house flipping to note investing, Nathan shares how taking action without having everything figured out led to real results.

What You Will Learn in This Episode

•  Why most people wait too long before starting their entrepreneurial journey 
•  How Nathan transitioned from teaching into entrepreneurship 
•  Lessons from franchising, real estate, and note investing 
•  Why running the numbers is critical before making decisions 
•  The reality of failure and how it shapes long term success 
•  How to evaluate business opportunities with clarity 
•  The importance of setting boundaries while working from home 
•  Why you do not need to know everything to get started 

About Nathan Turner

Nathan Turner is an experienced mortgage note investor and the founder of Earnest Investing, where he helps investors generate passive income through note investing. His journey includes owning Curves franchises, flipping houses, and building a business focused on buying and selling residential mortgages across the United States

He is also the host of The Real Estate Notes Show and the organizer of the Diversified Mortgage Expo, where investors and experts come together to learn and build connections.

onnect with Nathan

•  Website: https://earnestinvesting.com/
  
  
•  LinkedIn: https://www.linkedin.com/in/nathan-turner-a9a1b510
  
  
•  Facebook: https://www.facebook.com/nathan.turner.35110
  
  

Did you start your business for freedom but now feel more stuck than ever

Why do so many entrepreneurs end up working more instead of less
 And what if the problem is not your effort but how your business is structured

In this episode of At the End of the Day, Chris Raimo sits down with Jason McKenzie, entrepreneur, author, and founder of Boise Web and the Zora Business Movement, to unpack one of the biggest hidden challenges in entrepreneurship

Jason shares powerful insights from years of coaching business owners and his own journey of building, struggling, and rebuilding businesses that actually support your life instead of controlling it.

What You Will Learn in This Episode

•  Why so many entrepreneurs unknowingly build businesses that trap them 
•  The mindset shift needed to move from overwhelmed to in control 
•  The 10 percent rule and how delegation unlocks growth 
•  How to hand off responsibilities without losing control of your business 
•  Why your business will never outgrow you without systems 
•  The difference between task management and time management 
•  How ADHD can be a strength in entrepreneurship 
•  Why redefining success is key to building a business you actually enjoy 

Key Takeaways

•  Freedom in business requires structure not just effort 
•  Delegation is essential if you want to scale your time and impact 
•  Your business reflects your mindset and personal growth 
•  Success should be defined by your life not just your revenue 
•  Small consistent steps create long term progress 
•  Entrepreneurship is one of the most intense forms of personal development 

About Jason McKenzie

Jason McKenzie is an author, dynamic speaker, and entrepreneur known for his high energy and story driven approach to business. As one of 17 siblings, his journey has shaped his resilience and perspective on growth and leadership.

He is the founder of Boise WEB, the Grazora Business Movement, and the Small Business Big Visibility Podcast. Jason has helped hundreds of entrepreneurs simplify business growth, take actionable steps, and build businesses they genuinely enjoy rather than ones that trap them.

Connect with Jason McKenzie

•  Website: https://www.jason-mckenzie.com/
  
  
•  Podcast: https://smallbusinessbigvisibility.com/
  
  
•  YouTube: https://www.youtube.com/@SmallBusinessBigVisibility
  
  
•  Facebook: https://www.facebook.com/jason.mckenzie.3745
  
  

If this episode made you rethink how you are building your business share it with another entrepreneur who needs to hear it
 Follow the podcast for more real conversations about entrepreneurship and leave a review to help more people discover the show

What if burnout is not something to push through but a signal you are ignoring

Why do so many entrepreneurs keep going until they crash
 And what would happen if you built your business around your energy instead of fighting it

In this episode of At the End of the Day, Chris Raimo sits down with Anni Eza, co founder of Seeds of Bliss, to explore a different approach to entrepreneurship rooted in healing, awareness, and honoring your natural cycles.

With over 10000 healing sessions and more than 15 years of experience, Anni shares powerful insights on burnout, the nervous system, and why rest may be the missing piece to sustainable success.

What You Will Learn in This Episode

•  Why burnout happens even to high performing entrepreneurs 
•  The role of the nervous system in business growth and decision making 
•  How overstimulation and constant consumption affect your productivity 
•  Anni’s simple 3 2 1 rule for better rest and recovery 
•  Why rest is not a weakness but a strategy for higher performance 
•  How honoring your natural cycles can increase creativity and clarity 
•  The truth about accountability and taking ownership of your life 
•  Why outsourcing what drains you can unlock exponential productivity 

Key Takeaways

•  Burnout is a signal not a failure 
•  You cannot operate in constant high performance cycles forever 
•  Rest creates clarity creativity and better decision making 
•  Sustainable businesses are built around energy not hustle 
•  Your best ideas often come when you are not working 
•  Bringing your full humanity into business is the new paradigm

About Anni Eza

Anni Eza is a catalyst for transformation, master healer, ego death doula, teacher, and co founder of Seeds of Bliss. With over 10000 healing sessions and certifications in more than ten modalities, she created Awakening the Seeds, a transformational process that guides people to reconnect with who they are beneath fear, conditioning, and survival patterns.

Her work exists in the space between light and darkness, helping individuals embrace both with awareness and skill. Through her journey, Anni has come to understand that her sensitivity and depth were never a burden, but a gift that allows her to support others in healing, leadership, creativity, and personal evolution.

Connect with Anni

•  Website: https://seedsofbliss.life/en/
  
  
•  Instagram: https://www.instagram.com/seeds.of.bliss
  
  
•  Facebook: https://www.facebook.com/seeds.of.bliss/
  
  
•  YouTube: https://www.youtube.com/@SeedsofBliss
  
  
•  TikTok: https://www.tiktok.com/@seeds.of.bliss

If this episode shifted your perspective on burnout and productivity, share it with someone who needs this reminder.
 Follow the podcast for more honest conversations about entrepreneurship and leave a review to help more people discover the show.