That Big CEO Energy

 We have an incredible guest on the show today!  Madeleine Raiford-Holland shares her incredible journey of building three successful companies and a thriving community of over 2 million people. 

We chat with her about all strategies for creating massively profitable short-term rental businesses and the importance of automation and delegation for sustained success. 

Guest Bio: Madeleine Raiford-Holland is the founder of MHM Luxury Properties and Madeleine Raiford-Holland Education. Her mission is to inspire anyone feeling trapped by the 'golden cuffs' of a traditional job to step out of their comfort zones and build their own profitable short-term rental businesses. With a background in business automation and processes, Madeleine has successfully grown a seven-figure boutique short-term rental brand and now helps others achieve financial and time freedom.

 What You'll Learn:

🔸 Madeleine’s journey from a nine-to-five job to successful entrepreneurship 

🔸 The importance of automation and delegation in scaling a business

🔸 How to create a curated and elevated guest experience in the short-term rental market 

🔸 Real-life success stories of people who have achieved financial and time freedom 

🔸 Strategies for overcoming the 'messy middle' phase of business growth If you're interested in transitioning from a traditional job to achieving financial independence and flexibility in life, this episode is a must-listen. 

Tune in now to learn practical tips and get inspired by Madeline's story!

Timestamps:

00:00 Meet Madeleine

02:16 Tech Issues and Podcasting Fun

05:18 Madeleine’s Journey to Entrepreneurship

09:03 Building a Short-Term Rental Empire

12:19 The Messy Middle: Overcoming Challenges

15:54 Automating for Success

20:59 Coaching and Mentorship

24:09 Client Success Stories

28:14 Defining Freedom and Mindset

Connect with Madeleine:

 On Instagram

Her Website

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

Perfectionism isn't a badge of honor; it's fear dressed up in productivity clothes. 

Through personal experiences and stories of clients like Laura Kelly, who embraced messy action, I'll show you how starting before you're ready leads to real results. Take, for example, a client who launched a boutique on Instagram with just a rack of clothes and ended up opening a fully funded retail store, or another who made $40,000 in her first year as a bookkeeper without a logo or a website. 

Are you ready to take action? Here are five practical steps: 

1. Sell before you're ready. 

2. Show your process. 

3. Set a launch date and stick to it. 

4. Use what you have. 

5. Ask for feedback, not approval. 

Remember, clarity comes from trying and adjusting, not from sitting and planning. If something resonated with you in this episode, we will link any mentioned resources in the show notes. Let's embrace messy action together and start building your dreams. You are worth starting at 70%.

Timestamps:

00:00 Introduction

00:22 The Perils of Perfectionism

03:22 Real-Life Stories of Messy Action

13:07 Practical Steps to Take Messy Action

19:18 Conclusion

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

As an entrepreneur myself, I've realized that building a successful business isn't just about strategy and hustle; it's about healing and growth. 

Here's what you'll learn in this insightful episode: 

• The difference between 'little T' and 'big T' traumas and how each impacts our lives and businesses differently.
• The profound connection between feeling good personally and the success of your business, and vice versa.
•  How struggles from our past can drive us positively in our entrepreneurial pursuits, pushing us to achieve beyond expectations and the dangers of operating in survival mode and the importance of transitioning to a thriving mindset to avoid burnout. 
• The importance of setting boundaries, seeking therapy, or community support to manage and understand recurring patterns in business behavior.

Join me in this episode as I share lessons, anecdotes, and thought-provoking questions to help you recognize and manage your past for a thriving personal and professional life.

Timestamps:

00:00 Introduction

01:52 Understanding Trauma: Little T vs. Big T

03:16 Sifting Through Trauma: A Personal Journey

05:23 The Impact of Trauma on Business Performance

07:07 Entrepreneurial Drive: Turning Struggles into Strengths

11:35 Survival Mode vs. Thriving Mode in Business

13:42 Personal Anecdotes: Performance and Perfectionism

19:38 Navigating Emotions and Setting Boundaries

31:53 The Wholeness Journey: Balancing Life and Business

37:27 Outro

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

Welcome back to That Big CEO Energy! It’s been a minute, but I’m thrilled to be here with you again. In this episode, I’m peeling back the curtain on a life-changing event that reshaped my perspective—an accident with my horse that left me with torn ligaments, months of recovery, and unexpected revelations.

Through this season of forced stillness, I rediscovered my love for writing, embraced deep self-reflection, and committed to playing big as I approach my 40th birthday. I’m sharing:

🔹 The accident that changed everything and how my horse showed up for me in ways I never expected
 🔹 Lessons from being sidelined—what it taught me about business, personal growth, and faith
 🔹 How I reignited my passion for writing and the role of Beth Kempton’s Do What You Love course in my journey
🔹 Why I’m leaning into the number 40 and making this my biggest year yet
🔹 The future of That Big CEO Energy—expect a blend of business, mindset, and personal growth conversations

If you’ve ever faced a setback that forced you to slow down and rethink your path, this episode is for you. Let’s dive into resilience, purpose, and the power of embracing life’s unexpected detours.

🎧 Listen now and don’t forget to subscribe for more episodes on business, mindset, and personal transformation!

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

Ever felt like the dream of entrepreneurial freedom has turned into a never-ending to-do list? Join me on this episode as I dive into my transformative journey from corporate HR to becoming the CEO of Kal+Co., and later, the founder of Little Martha's Bakery. 

Discover how trading high heels for a sourdough starter opened unexpected pathways and taught me invaluable lessons about entrepreneurship and embracing my inner CEO energy.

Timestamps:

0:00:00 - 0:12:27 | Nurturing Entrepreneurship
Explore my transition from corporate HR to entrepreneurship, driven by the desire to integrate my passions and strengths. Reflect on overcoming fears and embracing my CEO energy.

0:12:27 - 0:29:19 | Launching Little Martha's Bakery
Take a nostalgic look at the culinary influences of my grandmothers, Oma and Gigi, and the inspiration behind launching my sourdough business. Discover how it connects back to family baking traditions.

0:29:19 - End | Embracing the Power of Trying
Encouragement to adopt a mindset of trying new things and taking risks for growth. Learn the importance of making bold moves without regrets.

Key Takeaways:

• Integrating Passions: How personal influences and passions shape your professional journey.
• Overcoming Barriers: Embrace your unique CEO energy and overcome fears.
• Empowerment Through Diversity: Pursue multiple interests and create a multifaceted life.
• Taking Action: Be inspired to try new things and make bold moves without regrets.

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

Ever felt like the dream of entrepreneurial freedom has turned into a never-ending to-do list? That moment hit me hard when I found myself drowning in administrative tasks and managing client expectations, leaving me disillusioned with the business I had once been so passionate about. 

Join me on this episode of That Big CEO Energy as we dive deep into the stark contrast between the idealized vision of business ownership and the often overwhelming reality. We talk about how important it is to lean on community and mutual support to navigate these choppy waters and reclaim the sense of freedom we all crave.

Entrepreneurs often find themselves trapped by their own fears and pressures, suffocating their strategic growth and long-term vision. 

We'll explore three major challenges that contribute to these feelings: 

• the fear of delegation,
•  blurred boundaries between work and personal life, 
• and unrelenting financial pressures. 

These obstacles can make anyone feel overwhelmed and burnt out, and we discuss actionable steps to tackle them head-on. It's time to break free from these chains and rediscover the excitement and purpose that led you to start your business in the first place.

By focusing on core values and personal well-being, we're paving the way for meaningful growth and true entrepreneurial freedom. Tune in and let's transform our business journeys together, one empowered step at a time.

Timestamps:

0:00:00 - 0:05:00 | Breaking Free

0:05:30 - 0:14:15 | Overcoming Entrepreneurial Challenges

0:14:15 - 0:26:06 | Finding Freedom in Business

0:26:06 - 0:27:07 | Empowering Your Business Freedom

Stay Connected:

Need to learn how to lead with BIG CEO Energy but don’t know where to start? Let’s Connect Here

Visit the website to learn how I can serve your business as a Fractional COO  www.thekalandco.com

Do you have broken systems and processes and need help STAT? Check out my 1:1 Project Intensive where I come in like Superman and leave you with the cape! https://thekalandco.com/services

Let’s be friends on social:

Follow me on Instagram @_kalandco

Connect with me on LinkedIn

I would be really grateful if you left a review on iTunes so that others can find and turn on  their CEO Energy  too! Just click here to review, select “Ratings and Reviews” and “Write a Review” . I'd also love to hear what your favorite part of this episode is in the comments below. Thank you!

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

Remember the first time you tried to explain your business and ended up either blanking out or overwhelming your listener with too much info? Trust me, I’ve been there too. On today's episode of That Big CEO Energy, I'm opening up about my own embarrassing moments as the CEO of Calendco, where I struggled to succinctly convey what I actually do. Through sharing my personal journey, I unpack the common fear of judgment that holds many of us back and reveal strategies to craft an elevator pitch that’s both clear and confident.

Why does talking about our work feel so daunting? Together, we’ll explore this question and examine the unconscious barriers that keep us from fully embracing our entrepreneurial roles. From transitioning from corporate titles to wearing multiple hats as business owners, I’ll provide practical advice to help you communicate your value without the anxiety. 

In this episode of That Big CEO Energy, you’ll learn:

• Overcoming Fear and Judgment: How you can overcome fears like judgment and imposter syndrome, with strategies to build confidence in sharing your business value.
• Crafting a Clear Elevator Pitch: Tips on creating a concise and compelling elevator pitch, emphasizing simplicity, clarity, and highlighting service benefits.
• Practical Application and Practice: The importance of practicing the elevator pitch in various settings to refine it and boost confidence in sharing one's business story.

Whether you’re managing a side hustle or a full-scale operation, let’s kick the notion of "small business" to the curb and step into the powerful CEO energy we’ve always envisioned. Tune in for actionable tips and the encouragement you need to share your story proudly and effectively.

Timestamps:

00:00 - 02:30 - Introduction

02:31 - 05:00 - Personal Journey

05:01 - 10:00 - Why Talking About Our Work Feels Daunting

10:01 - 15:00 - Crafting Your Elevator Pitch

15:01 - 20:00 - Practical Advice and Examples

20:01 - 25:00 - Addressing Imposter Syndrome

25:01 - 30:00 - Overcoming Overwhelm

30:01 - 35:00 - Refining and Practicing Your Pitch

35:01 - 40:00 - Real-Life Scenarios

40:01 - 45:00 - Recap and Encouragement

45:01 - 47:00 - Conclusion

47:01 - 48:00 - Outro

Stay Connected:

Need to learn how to lead with BIG CEO Energy but don’t know where to start? Let’s Connect Here

Visit the website to learn how I can serve your business as a Fractional COO  www.thekalandco.com

Do you have broken systems and processes and need help STAT? Check out my 1:1 Project Intensive where I come in like Superman and leave you with the cape! https://thekalandco.com/services

Let’s be friends on social:

Follow me on Instagram @_kalandco

Connect with me on LinkedIn

I would be really grateful if you left a review on iTunes so that others can find and turn on  their CEO Energy  too! Just click here to review, select “Ratings and Reviews” and “Write a Review” . I'd also love to hear what your favorite part of this episode is in the comments below. Thank you!

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

"Finding the right balance between being committed to your business and maintaining a healthy personal life is essential for long-term success and well-being." - Kallai Plummer

When I first launched my operations management firm, I was all in—working long hours, skipping social events, and constantly mulling over work. While I thought this level of dedication was the key to success, it soon became clear that it was taking a toll on my personal life and well-being. Tune into this episode of Big CEO Energy as we explore the balance between being passionately involved in your business and maintaining a healthy personal life. I'll share my journey of learning to "date" my business rather than being "married" to it, and how this shift led to greater success and happiness.

Join me as we discuss the dating versus marriage analogy, helping you recognize if your business commitment is leading to burnout or balance. We'll break down how to stay enthusiastic and passionate about your work without letting it overshadow other important areas of your life. With relatable examples and practical tips, this episode is a must-listen whether you're just starting out or have been running your business for years. Let’s find that sweet spot where you can achieve sustained success and happiness in both your business and personal life.

Timestamps:

0:00 - 5:00: Introduction and Personal Story

5:01 - 15:00: Identifying Overcommitment and Under Commitment

15:01 - 25:00: Finding the Right Balance

Stay Connected:

Need to learn how to lead with BIG CEO Energy but don’t know where to start? Let’s Connect Here

Visit the website to learn how I can serve your business as a Fractional COO  www.thekalandco.com

Do you have broken systems and processes and need help STAT? Check out my 1:1 Project Intensive where I come in like Superman and leave you with the cape! https://thekalandco.com/services

Let’s be friends on social:

Follow me on Instagram @_kalandco

Connect with me on LinkedIn

I would be really grateful if you left a review on iTunes so that others can find and turn on  their CEO Energy  too! Just click here to review, select “Ratings and Reviews” and “Write a Review” . I'd also love to hear what your favorite part of this episode is in the comments below. Thank you!

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

"Price is what you pay, value is what you get." - Laurie Barkman

Are you struggling to see what your exit plan is in your business? Today, my guest and I are unlocking the secrets to building a business that thrives without you at the helm!

Join us as we chat with Laurie Barkman, a veteran in business transitions and exits, who shares invaluable lessons from her journey, including her tenure as the CEO of a $100 million company acquired by a Fortune 50 giant. 

Laurie unpacks the importance of balancing hustle culture with creating sustainable systems, and why starting exit planning early can significantly enhance your business's value. As the Business Transition Sherpa, Laurie provides key strategies to ensure your enterprise remains resilient through economic downturns and pandemics while keeping growth on track.

In this episode of That Big CEO Energy, you’ll learn:

• Importance of Independence: Laurie emphasizes that a successful business should operate independently of its owner to enhance its value and attractiveness to potential buyers.
• Balancing Hustle and Sustainability: Learn how to navigate the balance between the 24/7 hustle culture and creating sustainable systems that allow your business to thrive without you.
• Exit Planning: Laurie shares why planning for an exit from the beginning is crucial for long-term success and how her Sherpa framework helps business owners transition smoothly.

Learn how to navigate the complexities of business valuation and why your business needs to operate independently of you to maximize market value. Whether you’re a solopreneur looking to scale or a seasoned owner planning your next move, Laurie’s insights on strategic planning and personal transition will guide you in making informed, regret-free decisions for your business's future.

Timestamps:

0:00 - Introduction

2:15 - Building a Business Without You

5:45 - Balancing Hustle and Sustainability

9:30 - Exit Planning

13:20 - Transitioning from Job to Asset

17:10 - Strategic Growth

21:05 - External Challenges and Opportunities

24:50 - Strategic Planning for Business Transition

28:30 - Business Valuation

32:15 - Team-Based Model for Solopreneurs

36:40 - Resources Mentioned

38:20 - Special Offers

39:15 - Connect with Lori Barkman

40:00 - Call to Action

Connect with Laurie Barkman

Website: https://thebusinesstransitionsherpa.com/

Podcast: "Succession Stories"

Book: "The Business Transition Handbook"

Course: "Endgame Entrepreneurship"

Additionally, If you want your business to be ready to sell at maximum value, now is the best time to start planning. Join the Endgame Entrepreneurship Masterclass at https://endgame.thinkific.com/courses/endgame-entrepreneurship. 

Get a 10% discount at checkout with code: bigceo10

They also offer an Affiliate Program and if you are interested in learning more, please visit their partner page.

https://thebusinesstransitionsherpa.com/affiliate-partners/ 

Stay Connected:

Need to learn how to lead with BIG CEO Energy but don’t know where to start? Let’s Connect Here

Visit the website to learn how I can serve your business as a Fractional COO  www.thekalandco.com

Do you have broken systems and processes and need help S

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review” 

“Even if you're the only one in your business, say it with me: I need an SOP."- Kallai Plummer

Have you ever felt like you're juggling a million tasks and deadlines in your business, only to realize you've dropped the ball on the project that mattered most? That's where I found myself before I learned the art of project management. 

In this episode, you’ll learn:

• How solopreneurs and small teams can create clear objectives and goals, implement Standard Operating Procedures, and avoid the common traps of project planning. 
• It's not about chasing perfection; it's about crafting a reliable blueprint that keeps your business on course.

As we explore the nooks and crannies of project planning and timeline management, I'll walk you through my own experiences of assigning responsibilities, the significance of visual planning, and the transformative power of CEO days for self-assessment. You'll learn why tools like Asana are game-changers for staying organized and hitting those deadlines.

To cap it off, we'll have an honest chat about effective project management as the backbone of success. Regular check-ins, proactive approaches to challenges, and the flexibility to adjust timelines are all part of the dance. I'll also share why asking for help isn't just smart—it's strategic. So grab your notebook, and let’s fuel each other with our collective stories of triumph, as we harness that big CEO energy together.

Timestamps:

00:00 Mastering Project Management for Entrepreneurs

15:26 Project Planning and Timeline Management

22:39 Effective Project Management for Success

34:05 Taking Control of Your Business Growth

If you're ready to transform your small business through expert project management techniques and avoid common pitfalls, then this is the episode you can't afford to miss. Tap into your inner CEO and join us as we navigate the roadmap to entrepreneurial success, one strategic step at a time.

Stay Connected:

Need to learn how to lead with BIG CEO Energy but don’t know where to start? Let’s Connect Here

Visit the website to learn how I can serve your business as a Fractional COO  www.thekalandco.com

Do you have broken systems and processes and need help STAT? Check out my 1:1 Project Intensive where I come in like Superman and leave you with the cape! https://thekalandco.com/services

Let’s be friends on social:

Follow me on Instagram @_kalandco

Connect with me on LinkedIn

I would be really grateful if you left a review on iTunes so that others can find and turn on  their CEO Energy  too! Just click here to review, select “Ratings and Reviews” and “Write a Review” . I'd also love to hear what your favorite part of this episode is in the comments below. Thank you!

Support the show

 Want to Be a Guest? Have a story, lesson, or business breakthrough to share with other CEOs? → Apply to Be a Guest 

What if your business had a solid foundation by this time next week? → Download the Free CEO Starter Kit

Could a supportive community be the thing you're missing in your momentum? → Join The Kallective Mentorship, accountability, and bi-weekly sessions to build your business the smart way.

 → GET THE GOOD MAIL Lots of fun. Never spam. Promise.

Let’s be friends on social:

Instagram @_kalandco

I would be grateful if you left a review on iTunes so that others can find and turn on their CEO Energy too! Just click here to review, select “Ratings and Reviews” and “Write a Review”