Realistic CEO Podcast

In this episode of the Realistic CEO Podcast, the host interviews Ali Connor, owner of Camp K9 Doggy Daycamp & Sleepovers, which provides daycare for about 80 dogs a day and overnight care, plus events like dog birthday parties and holiday visits. Ali shares how she shifted from dreams of radio and broadcasting into entrepreneurship, leaving a corporate job to build Camp K9 after struggling to find consistent care for her own dog. She explains the importance of learning the industry through classes, prioritizing safety training like dog first aid/CPR, and staying current through ongoing courses. Ali discusses early challenges such as being “on” 24/7, balancing life through trusted staff, finding support via online owner groups, and using ChatGPT mainly to refine emails and social posts. She offers advice on finances, planning, networking, pivoting, and interpreting the book’s five types of work and “LBW” (long, lonely, boring work).

00:00 CEO Dream Origin

00:27 Meet Ali Connor

01:06 From DJ to Dog Daycare

02:29 Building Camp K9

03:47 Safety Training Essentials

05:24 Money Advice for Entrepreneurs

06:49 Always On as Owner

09:44 Support Groups That Help

12:40 Using AI at Work

14:15 Quitting Corporate to Go All In

17:03 Hiring the Right Team

19:42 Reading the CEO Book

23:09 Handling Doubters

23:42 Dreams Over Doubt

24:52 Doggy Daycare Naysayers

27:11 Advice Without Support

28:51 Lemonade Stand Basics

29:51 Pivoting Through Change

30:40 Learning To Say No

33:15 Five Types Of Work

36:26 Long Lonely Boring Work

37:54 Helping Kids Believe

40:18 Fun Fact And Farewell

42:48 Support And Next Episode

In this episode of the Realistic CEO Podcast, the host interviews Karen Finn of the Springfield Cultural Partnership, which connects artists, cultural organizations, nonprofits, advocacy groups, and the city to create opportunities, visibility, and community wellness while treating artists as essential workers. Karen shares her path from Texas to a presidential fellowship in Washington, DC working with the Department of Defense and the Marine Corps, where she learned about integrity, accountability, and organizational camaraderie, then later moving to Western Mass and taking a leap into arts and culture work using her fundraising and policy background. She discusses similarities between her roles, the importance of asking communities what they need, grant writing and value propositions, balancing mission alignment, and adapting programs while honoring community-driven projects like Trust Transfer. The host reads his book “I Am a CEO,” prompting Karen’s reflections on working hard, smart, right, networking, teamwork, and the long, lonely, boring work, and she shares a new pop-up civic space grant and her love of scuba diving.

00:00 CEO Dream Origin

00:22 Meet Karen Finn

00:45 What Cultural Partnership Does

01:38 Karen Journey To Springfield

03:19 DOD Fellowship Lessons

05:42 Grit And Taking Leaps

12:37 Artists Community Impact

14:42 Fundraising Real Talk

17:54 Grant Fit And Storytelling

21:03 Building Programs Process

23:05 Storytime I Am CEO

27:14 Working Hard Defined

27:58 Working Smart Strategies

28:54 Doing Work the Right Way

30:41 Networking With Integrity

31:52 Teamwork and Diverse Teams

33:19 Tackling the LBW Grind

36:48 Pop-Up Civic Space Grant

38:50 How They Won the Grant

43:11 Fun Fact Scuba Diving

45:08 Closing Advice and Thanks

On the Realistic CEO Podcast (Future Leaders Edition), the host interviews Adetayo , a 25-year-old vice president of human resources at Glen Meadow, about how she mapped out a career plan starting at 17 through internships, transferable skills, and researching career paths on LinkedIn. Adetayo highlights key skills like communication, being a people person, and networking, and explains how Glen Meadow’s “Kindness first, growth always” culture, CliftonStrengths focus, and leadership team support employee development and resident wellbeing. She shares a person-centered HR approach aimed at “putting the human back in human resources,” offers advice on overcoming imposter syndrome through mentors, writing goals, and confidence, and discusses Gen Z leadership, job mobility, and workplace change. The episode also covers the host’s book “I Am a CEO,” the five types of work, and the LBW (long, lonely, boring work).

00:00 CEO Dream Origin

00:22 Meet Adetayo VP HR

01:24 Fast Track to VP

02:39 Transferable Skills Networking

03:30 Strategic Career Blueprint

05:55 Why Glenmeade Culture

08:41 Human Centered HR

12:36 Gen Z Leadership Mindset

16:44 Beating Imposter Syndrome

18:37 Pivoting After Failure

20:46 Networking Like a Pro

23:02 Book Five Types Work

27:54 LBW Long Lonely Work

28:30 Wins Challenges Fun Fact

30:46 Final Thanks Next Steps

In this special Future Leaders episode of the Realistic CEO Podcast, the host interviews Ted, a news producer at WWLP 22 News in Western Massachusetts, about how he got into local media through communications and journalism studies at Western New England University, networking, and experience in college and professional radio. Ted explains why local news is a public service, how stories are found through police departments and scanners, and shares memorable assignments like covering an attempted robbery call and four electric buses on fire in -10° weather. He advises aspiring journalists to build a portfolio, practice on-camera skills, and gain experience interviewing. The conversation also covers cherishing the present, Ted’s career goals, and the host’s Realistic CEO journey and book, including the five types of work and the LBW (long, lonely, boring work), plus a fun fact about ear-wiggling.

00:00 Proving CEO Dreams Real

00:27 Meet Ted the Producer

01:03 Breaking Into Local News

03:22 Chasing Stories Safely

04:47 Favorite Features and Wild Nights

07:07 Advice for Aspiring Journalists

08:34 Radio Roots and Career Lessons

10:20 Future Goals and Mentorship

12:35 Turning No Into Momentum

17:24 Storytime Realistic CEO Book

21:03 Handling Doubt and Staying Driven

23:53 Five Types of Work

27:11 LBW Overnight Grind

28:00 Fun Fact and Farewell

Mikey hosts the Realistic CEO Podcast with guest Julie Phillips, Executive Director of Development at HCC, who leads the alumni and development team within institutional advancement and focuses on storytelling to bring resources like scholarships, emergency funds, labs, and buildings to support students. Julie shares how she entered fundraising through networking and a part-time assistant role in 2010, was recruited to HCC in 2019, and faced major challenges including rapid change, state-institution constraints, and maintaining a positive mindset. She advises Mikey on funding his nonprofit Realistic Lemonade by aligning with mission-matched funders, using data and emotional storytelling, applying broadly, and leveraging LinkedIn and networks. Julie highlights favorite moments at HCC, including a successful pandemic-era Giving Day, a mentorship program with 100% retention, and President George Timmons’ inauguration, and discusses hard work, smart delegation, working right with integrity and data, teamwork, and long, unseen effort.

00:00 Dreaming of CEO

00:22 Meet Julie Phillips

00:38 What Advancement Does

01:37 Finding Fundraising Later

02:40 Career Path to HCC

03:56 Biggest Challenges Today

06:48 Funding a New Nonprofit

09:23 Entrepreneurial Backstory

12:39 Reframing Rejection

15:19 Favorite Wins at HCC

20:29 Mentorship and Representation

21:54 Teachers Build Confidence

24:02 Mentorship That Makes You Grow

26:24 Five Types of Work

26:38 Working Hard Lessons

28:05 Working Smart Boundaries

29:22 Working Right With Data

30:17 Networking Opens Doors

32:17 Teamwork And Crucial Talks

34:06 Long Lonely Boring Work

37:07 Fun Fact Handstands And Clowning

38:39 Final Thanks And How To Support

In this episode of the Realistic CEO Podcast, the host interviews Jawad Khokhar of Tyrbrook Financial about what a financial planner does for individuals and entrepreneurs, including business structure reviews, tax planning coordination with CPAs, estate planning, and risk coverage like life and disability insurance. Jawad shares how he moved from college finance studies and retail into banking, got sponsored for licensing, and eventually went independent, describing the long, lonely, boring work of building a book of business and improving work-life balance with calendars and a dedicated office. He explains differences between accountants and planners, common business-owner mistakes like poor bookkeeping and improper entities, and gives an example where switching from an LLC setup to an S-corp structure saved a client about $5–6K. The host reads from his children’s book I Am A CEO and discusses the five types of work, financial literacy in schools, goals to distribute 500,000 books, and a podcast goal of interviewing Shaquille O’Neal.

00:00 Dream to Be CEO

00:23 Meet Jawad

00:41 What a Financial Planner Does

02:40 How He Got Started

05:22 Accountant vs Advisor

07:46 Common Business Mistakes

10:02 LLC vs S Corp

12:50 Boosting Profitability

14:42 Going Independent

17:12 Storytime CEO Book

22:36 Five Types of Work

24:55 LBW and Work Life Balance

26:47 Calendar Balance Hacks

27:25 When School Slips

28:17 Advice To 19

29:18 YouTube Rabbit Holes

31:30 Travel Goals From TikTok

32:20 AI And Future Jobs

34:53 Trade Schools And Taxes

37:34 CEO Impact In Schools

40:54 Books And Reading Plans

42:32 Big Goals And Sponsors

43:15 Dream Guest Shaq

46:14 Podcast Sign Off

The host of the Realistic CEO Podcast shares how a teacher once said becoming a CEO was unrealistic, inspiring a mission to help kids believe their dreams can come true. He interviews Victor Narvaez, co-owner of Good Works Coffee House in downtown Chicopee, a coffee shop built around community impact, partnerships with nonprofits, and internship opportunities for at-risk youth. Victor describes his 11 years as a social worker with the Department of Children and Families, his passion for representation and mentoring adolescents, and why he chose a coffee shop as a community hub. The host reads his children’s book about becoming a CEO and discusses collaboration to inspire students. Victor explains the five types of work—working hard, smart, right, networking, and teamwork—plus LBW (long, lonely, boring work) like weekly inventory, and shares a fun fact: he’s a singer who performed at the Apollo Theater.

00:00 Dream to Be CEO

00:22 Meet Victor

00:42 Good Works Mission

01:09 Social Work Roots

02:58 Mentoring Youth Vision

04:46 Why a Coffee Shop

05:31 Internship Stories

07:34 Storytime Realistic CEO

11:47 Five Types of Work

16:15 Imposter to Impact

19:49 Long Lonely Boring Work

20:30 Fun Fact and Wrap Up

21:07 Support and Next Steps

In this episode of the Realistic CEO Podcast, the host interviews Anne Kandilis, leader of Springfield Works, a citywide collaboration of employers, educators, and residents focused on economic mobility by expanding access, opportunity, and choice. Anne shares her Springfield upbringing, first-generation college path at UMass Amherst while working multiple jobs, early management experience, and career moves from a small accounting firm to the Big Four and beyond, including becoming a tax partner at 38 and later shifting from corporate work to policy and education-focused nonprofit work after consulting with Springfield Public Schools and related initiatives. They discuss helping students understand C-suite roles, the host’s children’s book I Am a CEO, Realistic CEO inspired by being told becoming a CEO was unrealistic, and the “five types of work” (work hard, work smart, work right, networking, teamwork) plus the LBW (“long, lonely, boring work”).

00:00 Proving CEO Dreams Real

00:22 Meet Springfield Works

01:22 From Springfield to Big Four

04:40 Why the Suit Mattered

06:22 Corporate to Community Impact

08:01 The Five Year Career Rule

09:45 Teaching Kids the C Suite

11:25 Making Partner and Lessons

13:29 Reading the Realistic CEO Book

18:37 Why I Wrote This Story

20:32 Teachers and Confidence

22:59 Five Types of Work Explained

29:07 The Long Lonely Boring Work

30:51 Fun Facts and Farewell

In this episode of the Realistic CEO Podcast, the host interviews Megan Burke, President and CEO of a Community Foundation, about her role doing “a little bit of everything,” from reviewing grants and scholarships to meeting donors, managing budgets, and engaging the board. Megan shares her career path from political science and economics studies to international work preventing the use of landmines and cluster munitions, later leading that organization as executive director, and then moving into community foundation work in Hartford before taking her current CEO position closer to home. They discuss how opportunities shaped her career, why local impact became more fulfilling, and how thriving communities involve those closest to challenges in decision-making. The host introduces his nonprofit Realistic Lemonade, distributing 5,000 books to Springfield students, reads from his book “I Am a CEO,” and asks Megan to define the five types of work and LBW, plus a fun fact about her learning ukulele during COVID.

00:00 Dreaming CEO Big

00:28 Meet Megan Burke

00:38 CEO Role Explained

01:37 Career Path Surprises

03:42 Early Jobs Lessons

05:07 College And Purpose

06:37 Global To Local Impact

09:13 Taking The CEO Leap

10:58 Communities Thrive Differently

13:17 Favorite Foundation Moments

15:03 Realistic Lemonades Mission

18:05 School Outreach Wins

21:06 Partnering And Grants

22:13 Storytime I Am CEO

25:54 Five Types Of Work

28:55 Long Lonely Boring Work

30:13 Imposter Feelings Overcome

32:02 Ukulele Fun Fact

32:40 Thanks And Support Links

In this episode of the Realistic CEO Podcast, the host interviews Bob Bolduc, who now runs a foundation serving youth and families in underserved communities and describes his team focused daily routine. Bolduc shares his upbringing in Springfield, his engineering degree from Notre Dame, and a master’s in business from Purdue, emphasizing that education and lifelong learning are essential to success. He discusses his enlisted Vietnam era military experience and what it taught him about leadership, following directions, teamwork, accountability, and respect. On entrepreneurship, he explains starting at his father’s gas station, building and selling multiple businesses, and growing Pride by working extreme hours, setting standards, and creating consistent systems. He also reacts to the host’s children’s book and breaks down “work hard,” “work smart,” ethics, networking, teamwork, and the “LBW” mindset.

00:00 CEO Dream Origin Story

00:22 Meet Bob Bolduc

00:39 Running a Youth Foundation

01:53 Education and Early Path

03:31 Learn Earn Return Framework

05:09 Military Service Lessons

07:27 Leadership Through Teamwork

09:50 Entrepreneurship Reality Check

12:17 Hard Work and Adaptation

12:50 Systems Standards and Flexibility

14:27 Why Education Wins Funding

16:04 College Or Bust

16:18 Selling Starts With Marketing

17:21 Learn Earn Return

18:09 Systems And Expectations

19:39 Why Pride Won

20:34 Scaling By Location

21:09 Storytime Realistic CEO

25:31 Five Types Of Work

26:13 Ethics Networking Teamwork

28:22 LBW And Final Thanks