Hey everyone, welcome to the very first episode of the Realistic CEO Podcast. I'm Mychal Connolly Jr., your host, and today I'm super excited to kick things off with someone who's not just my hero but also the coolest dad and a successful CEO, Mychal Connolly Sr.

In today’s talk, we dive deep into what it really takes to set your goals, the essential skills you need as a young person dreaming of becoming a CEO, and how to keep a positive and action-oriented mindset. My dad shares some priceless advice on finding the right balance between chasing your dreams with all you've got and still keeping your heart open and empathetic. We also touch on how to make the most out of today's tech to get ahead and why being persistent and tough can make or break your journey to the top.

This isn’t just another interview. It’s about passing down lessons on dreams, discipline, and determination from one generation to the next. It’s for all of you out there, whether you’re a teen like me, aiming to be the next big CEO, or someone a bit older looking to breathe new life into your career. This episode is filled with advice that’s timeless and truly for everyone.

🔹 What we cover:

    The real deal about setting goals and executing them as a leader.
    Key skills for up-and-coming CEOs: perseverance, effective communication, and empathy.
    Why fostering a positive culture and a supportive environment is crucial, wherever you are.
    How to juggle your ambition with maintaining meaningful family connections and relationships.

🔹 About Mychal Connolly Sr.:
He’s not just my dad. He’s a seasoned CEO who’s built successful businesses from the ground up. His journey is one of resilience and hard-earned wisdom, and he’s here to share insights that only come from real experience.

Thanks so much for tuning into our launch episode. Here’s to making our dreams a reality, one step at a time. Remember to hit like, share, and subscribe for more stories and tips from leaders who truly make a difference.

00:00 Introduction to the Realistic CEO Podcast
00:21 Inspiration and Early Goals
02:27 Key Qualities of a CEO
08:55 The Importance of Teamwork
10:21 Motivation Behind Starting a Business
13:12 Creating a Dream Environment
15:16 Overcoming Challenges and Staying Determined
22:01 Books for Aspiring CEOs
22:30 The Importance of Mindset
26:51 Networking Tips for Success
28:25 Creating a Positive Culture
36:59 Balancing Business and Family
41:24 Conclusion and Final Thoughts

Ep. 1 | Stand Out Truck® Dreams Come True with LBW | CEO Father Explains to Son Journey to Success.

In this episode of the Realistic CEO podcast, host Mike interviews Joanna, Vice President at the Community Foundation of Western Massachusetts. Joanna shares her inspiring journey from delivering newspapers as a young girl to becoming an influential leader in the nonprofit world. She discusses the importance of resilience, mentorship, and advocating for equity. Joanna also provides valuable advice for aspiring female executives and insights into the daily challenges and joys of her role. This conversation highlights the impact of community foundations and the significance of passion and teamwork in achieving success.

00:00 Introduction: The Dream of Becoming a CEO
00:24 Welcome to the Realistic CEO Podcast
00:39 Interview with Joanna: Journey to Leadership
03:27 Challenges and Mindset of a Female Leader
05:05 Advice for Aspiring Leaders
07:01 Balancing Passion and Career
07:30 Building a Strong Team
11:19 The Importance of Mentorship
12:17 Community Involvement and Volunteering
18:45 The Realities of Administrative Work
22:23 Maintaining Work-Life Balance
25:23 Creating a Positive Work Environment
28:46 Final Thoughts and Farewell

Ep. 45  | Joanna Ballantine | Community Foundation | From Paper Route to Empowerment

In this raw, real, and reflective episode, Myke Connolly Sr. jumps back into flow with Marketing and Cupcakes™ Random Zoom Call —an unscripted moment that turned into a full-on revival.

From battling burnout and ego to rediscovering the original assignment behind Marketing and Cupcakes™, this episode dives deep into:

• Why it's not about views—it's about starfish
• How copy-paste leprechauns drain your energy
• The difference between self-care and selfishness
• Why your circle should hold you accountable
• Powerful lessons from Mychal Connolly Jr. on stage, self-worth, and staying the course

This is for the entrepreneurs, creators, and community leaders who forgot the magic behind their mission.

Remember: You don’t prepare when you’ve been preparing.

🔁 Share with someone stuck in their own head.
🎯 Learn more at RealisticCEO.com
📚 Support the 500K book giveaway mission: Donate or sponsor at RealisticCEO.com/donate

Starfish, Suckas, and Following the Assignment

In this episode of the Realistic CEO Podcast, join us as we delve into the inspiring journey of Kevin Lynn, Executive Director of MassHire. Kevin shares his unique path from high school to becoming a CEO, overcoming setbacks and learning valuable lessons along the way. Discover his insights on leadership, the importance of relationships, and the value of persistence. Learn how Kevin turned challenges into opportunities and continues to help others find success through his work at MassHire. Don't miss this engaging conversation filled with practical advice and motivational stories.

00:00 Introduction: The Dream of Becoming a CEO
00:23 Welcome to the Realistic CEO Podcast
00:29 Guest Introduction: Kevin from MassHire
00:58 Kevin's Educational Journey
02:29 Career Path and Early Challenges
04:59 Lessons from Leadership
16:23 Networking and Building Relationships
20:36 Accidental Path to MassHire
25:36 Final Thoughts and Reflections
29:53 Conclusion and How to Support

Ep. 46| Kevin Lynn | MassHire | From Dreams to Reality

In this episode of the Realistic CEO Podcast, Mikey sits down with Tessa, the executive director of E for All, to discuss her critical role in nurturing new and growing entrepreneurs in the Pioneer Valley. Tessa delves into her unexpected journey from working in local government to leading a team that drives economic development. She shares insights about her work in fundraising, volunteer management, and relationship building. Tessa also opens up about her personal and professional growth, from grant writing to running for city council, and offers valuable advice on overcoming the fear of networking. Additionally, she highlights the transformative impact of E for All’s programs on entrepreneurs, sharing inspiring success stories along the way. Don't miss this engaging conversation filled with lessons on leadership, community building, and the power of persistence.

00:00 Introduction and Guest Welcome
00:13 Role and Responsibilities of an Executive Director
01:18 Career Journey and Early Experiences
05:14 Networking Tips and Overcoming Fears
07:48 Lessons in Leadership and Public Service
10:16 Running for City Council: Challenges and Triumphs
17:45 Impact of Local Government and Community Engagement
19:47 Success Stories and Personal Growth in Entrepreneurship
28:43 Fun Facts and Closing Remarks

Ep. 47 | Tessa Murphy-Romboletti | EforAll Pioneer Valley | Empowering Entrepreneurs

In this episode of the Realistic CEO Podcast, we follow the host on his quest to learn what it takes to become a CEO. Joined by Delcie Beam of Strategic IT, the discussion covers Delcie's journey from a high school computer repair gig to founding a successful, employee-owned IT company. They delve into topics such as the evolution of the business, the decision to create an ESOP, leadership qualities, and the importance of work-life balance. Delcie also shares practical advice for aspiring entrepreneurs and explains how technology, including AI, plays a crucial role in his business.

00:00 Introduction: The Dream of Becoming a CEO
00:23 Welcome to the Realistic CEO Podcast
00:28 Guest Introduction: Delcie Beam
00:36 Strategic IT: What We Do
01:00 The Journey to Employee Ownership
03:17 Early Business Days and Evolution
04:26 Naming the Business: The Story Behind Paras
05:43 Challenges and Support in Business
07:34 Advice for Aspiring Entrepreneurs
23:49 The Importance of Work-Life Balance
26:11 Fun Fact and Closing Remarks

Ep. 48 | How This CEO Turned a High School Side Hustle into a Multi-Million Dollar Tech Business

Join us on the Realistic CEO Podcast as we sit down with Nicole Obi, the President and CEO of the Black Economic Council of Massachusetts (BECMA). Nicole shares her eclectic journey from humble beginnings to leading a nonprofit dedicated to building black wealth through advocacy, programs, and events. Discover how BECMA supports black-owned businesses across Massachusetts, the importance of networking, and the lessons learned from Nicole's entrepreneurial ventures. Gain valuable insights into the challenges and triumphs of fostering economic inclusivity. Tune in for a compelling conversation filled with wisdom and practical advice for aspiring and established entrepreneurs alike.

00:00 Introduction: The Dream of Becoming a CEO
00:23 Welcome to the Realistic CEO Podcast
00:35 Interview with Nicole Obi: The Black Economic Council of Massachusetts
01:04 Nicole's Journey to Becoming a CEO
02:44 Funding and Supporting Black-Owned Businesses
05:54 Balancing Advocacy and Business Support
08:57 Building a Strong Team
10:34 Leadership and Risk-Taking
13:23 Networking and Partnerships
17:03 Advice for Entrepreneurs
28:02 Conclusion and Final ThoughtsBuilding Black Wealth: Insights from Nicole Obi, CEO of BECMA - Realistic CEO Podcast

Episode 49 | Black Wealth Isn’t a Dream — It’s a Plan

In this episode of the Realistic CEO Podcast, the host interviews Tracey, co-founder of Wicked Good Cupcakes. Tracey shares the story of how she and her daughter accidentally started their successful cupcake business, eventually landing a deal on Shark Tank and selling the company to Hickory Farms. Tracey discusses the challenges of starting with no experience, the importance of overcoming obstacles, and the value of persistence. She also touches on the power of manifestation and the nuances of making profitable business decisions. Tune in to hear her inspiring journey and gain insights into running a successful entrepreneurial venture.

00:00 Introduction: The Dream of Becoming a CEO
00:23 Welcome to the Realistic CEO Podcast
00:36 Interview with Tracey: The Birth of Wicked Good Cupcakes
01:59 Challenges and Breakthroughs: From Kitchen to National Security Threat
06:35 Shark Tank Experience: The Turning Point
07:47 Life Before and After the Business
16:12 Navigating Business Growth and Challenges
21:31 The Decision to Sell and Moving Forward
33:09 Final Thoughts and Farewell

Ep. 50 | | She Turned Cupcakes into a Million-Dollar Empire (Shark Tank Success Story)

Join us in this engaging episode of the Realistic CEO Podcast as we sit down with Dr. Kathy Martin, CEO of Glenmeadow, a senior living community. Dr. Martin shares her unique journey from higher education to becoming a CEO, the importance of transferable skills, and how she navigated this career shift. She provides valuable advice on leadership, team building, and running a nonprofit organization. Tune in to learn about the significance of maintaining a positive work environment, effective donor communication, and the power of staying open-minded throughout your career.

00:00 Introduction: The Dream of Becoming a CEO
00:29 Meet Dr. Kathy Martin: A Journey to Glenmeadow
00:54 Leadership Insights: From Higher Education to Senior Living
04:33 Building and Leading Effective Teams
09:10 Running a Nonprofit: Challenges and Strategies
11:45 Community Engagement and Visibility
21:16 Final Thoughts and Advice for Aspiring Leaders
27:31 Conclusion: Wrapping Up the Episode

Ep. 51 | From Higher Ed to the C-Suite: How Dr. Kathy Martin Became a Nonprofit CEO

In this episode of the 'Realistic CEO' podcast, host Mikey interviews Seth Kaye, a successful wedding and event photographer. They discuss Seth's unconventional path from a pre-med student to a thriving photography career. Seth shares insights into his passion for photography, the challenges he faced, and the lessons he learned. He also talks about the importance of building client relationships, the behind-the-scenes work that goes into photography, and the significance of capturing genuine moments. Tune in to hear Seth's inspiring journey and valuable advice for aspiring photographers.

00:00 Introduction: The Dream of Becoming a CEO
00:23 Welcome to the Realistic CEO Podcast
00:37 Meet Seth Kaye: A Journey in Photography
01:03 From Pre-Med to Photography: Seth's College Days
01:56 The Magic of Photography: Discovering a Lifelong Passion
02:29 Transition to Professional Photography
03:47 The Wedding Photography Business
04:32 Understanding Photojournalism
05:20 Building a Photography Career
09:21 The Art of Capturing Moments
11:42 Challenges and Rewards of Photography
18:42 Advice for Aspiring Photographers
22:17 The Long Lonely Boring Work (LBW)
23:07 Fun Facts and Final Thoughts

Ep. 52 | Why Seth Kaye Left Pre-Med to Capture Life’s Biggest Moments

In this episode of the Realistic CEO podcast, host Mikey interviews Dina from 94.7 WMAS, who recounts her unexpected journey from aspiring elementary teacher to a successful radio co-host. Dina describes her career changes, from initially wanting to work with children, to majoring in psychology, fashion merchandising, and finally communications. An unplanned internship at a radio station opened unexpected doors, leading her to an on-air career. She shares insights on the skills she’s learned, the challenges of transitioning from behind-the-scenes roles to being a public figure, and the importance of making connections with listeners. Dina also discusses the diverse roles and team members that keep a radio station running, and the extensive behind-the-scenes work involved. Tune in for an inspiring story about embracing opportunities and learning throughout a winding career path.

00:00 Introduction: The Dream of Becoming a CEO
00:24 Welcome to the Realistic CEO Podcast
00:45 Interview with Dina McMahon: Career Journey
01:28 Switching Majors and Finding a Path
02:46 Internship and Early Career Decisions
07:04 Transition to On-Air Radio Host
09:13 Skills and Advice for Aspiring Hosts
12:13 The Importance of Teamwork in Radio
14:31 Handling Nerves and Public Speaking
18:00 Connecting with Listeners Through Events
19:46 Memorable Moments and Bloopers
21:40 Reflections and Advice for the Next Generation
25:58 The Long, Lonely, Boring Work Behind the Scenes
27:56 Fun Facts and Closing Remarks

Ep. 53 | How a Random Internship Turned Into a Radio Career

My high school teacher said it’s unrealistic for me to be a CEO. Now I interview CEOs on my podcast to learn how to be a CEO. My goal for my journey, podcast, public speaking and book is to inspire people to pursue their dreams confidently, no matter what anyone tells them. Learn to be a CEO or become a better CEO with Realistic CEO.

Ep. 1 | Stand Out Truck® Dreams Come True with LBW | CEO Father Explains to Son Journey to Success.

Realistic CEO

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