EP. 85 | The “Boring Work” That Took Him From Teacher to Superintendent

EP. 89 | From Wanting a Suit to Becoming a Leader

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

EP. 88 Community Foundation

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

Ep 87 | The 3 Phases of Success: Learn, Earn, Return (99% Ignore This)

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

Ep. 86 | How One Banker Found Greater Impact in Community Lending

In this episode of the Realistic CEO podcast, Mike interviews Raymond , who leads Common Capital, a US Treasury-certified Community Development Financial Institution (CDFI) in Western Massachusetts that provides loans to small businesses that can’t get full financing from banks and pairs capital with free technical assistance, training, and education. Raymond shares his path from dropping out of college and starting in bank management training to commercial lending, then shifting to nonprofit community development finance after feeling big-bank work was too mechanical and profit-driven. He explains what CDFIs are, Common Capital’s origin story, how lending decisions focus on repayment ability, willingness, and a plan B, and why Common Capital prioritizes character, commitment ,and coachability over credit scores. Mike reads from his children’s book “I Am a CEO,” and Raymond discusses the “five types of work” and gives startup advice to write and share a simple plan, especially with skeptics. 00:00 Dream to Be CEO 00:27 Meet Common Capital 00:35 What Common Capital Does 01:41 From Banking to CDFIs 05:58 What Is a CDFI 07:26 Common Capital Origin Story 09:07 Why Leave Big Banking 11:09 Learning Business on the Job 12:14 How Lending Decisions Work 14:31 Beyond Capital Support 15:45 Becoming the CEO 16:52 Choosing the Right Borrowers 18:44 Character and Credit Bias 19:29 Credit Scores vs Character 20:28 Foreclosure Story Deep Dive 22:03 Reading Realistic CEO 25:37 Lemonade Stand Lesson 26:49 Five Types of Work 27:00 Working Hard Focus 28:08 Working Right Balance 29:43 Working Smart Strengths 30:33 Networking Relationships 31:25 Teamwork In Person 32:36 LBW Career Reflections 34:30 Startup Advice Simple Plan 36:21 Fun Fact Sleepy Voice 37:25 Thanks and Support Plug

EP. 85 | The “Boring Work” That Took Him From Teacher to Superintendent

On the Realistic CEO podcast, the host interviews Dr. Marcus Ware, the first superintendent guest, about what a superintendent does as the instructional leader and “keeper” of a district, including daily operations and even snow-day decisions. Ware shares his path from Springfield public schools and an early dream of becoming a TV meteorologist—failing out of college twice, restarting at STCC, finishing a meteorology degree, then discovering a passion for teaching and rising through roles in boarding and public schools to superintendent of Chicopee. He explains how snow-day calls are made using forecasts, timing, safety, and coordination with other superintendents and city officials. The conversation covers dealing with discouragement, uplifting students through relationships, advice to persist toward goals, and the host’s children’s book “I Am a CEO,” including its “five types of work” and the long, lonely, boring work. 00:00 Introduction and Dream 00:22 Meet Dr Marcus Ware 00:53 What Does a Superintendent Do 02:28 Educational Background Matters 03:21 Growing Up in Springfield 04:17 From Meteorology to Teaching 05:27 Climbing the Administrative Ladder 06:19 Becoming a Superintendent 07:23 Making Snow Day Calls 10:40 When It Became Possible 12:39 Advice for Aspiring Superintendents 15:22 Facing Discouragement and Doubt 17:33 Sharing Personal Experiences 18:52 Teachers as Dream Holders 19:49 Celebrating Great Teachers 21:25 Advice for Teachers 23:24 Building Student Relationships 25:01 Advice for Young People 25:41 Validating Student Dreams 26:30 Creating On Ramps to Success 27:57 Overcoming Obstacles and Finding Yes 29:30 Bringing Realistic CEO to Schools 30:40 Reading I Am A CEO 34:40 Guiding Students on the Right Path 36:05 The Five Types of Work 36:15 Working Hard Explained 37:44 Working Smart Explained 39:05 Working Right Explained 40:29 Networking as a Must Have 42:11 The Power of Teamwork 43:44 The Long Boring Work 46:37 Fun Fact About Heights 48:36 Closing Thoughts and Support