28. Building a Business That Doesn't Run Through You with Shay Prosser

39. From Medieval History to the C-Suite with Debbie Plager

Debbie Plager, Founder and CEO of The Plager Group, joins the show to talk about how a medieval history degree turned into a 25-year career in corporate talent leadership and now a coaching and organizational strategy firm. Debbie shares the story of temping for Anderson Consulting, discovering change management, and eventually helping HUB International win a Stevie's Gold Award for Best Employer. She and Jack dig into why teams (not individuals) are where real business transformation happens, her sweet spot serving $100M-$700M middle market companies, and how she is scaling from 1:1 coaching into a vetted team coaching model. Then it's a scrappy vs sophisticated lightning round covering everything from lap desks to asking for referrals. Chapters: Chicago Roots and the Scrappy Intro (00:00) Bootleggers, Mathematicians, and Zero Entrepreneurs (01:51) Medieval History to Anderson Consulting (04:21) Serf to Yeoman: Finding Change Management (05:36) The Best Employer Award and Summer Camp During COVID (12:59) Why Teams Are Where Work Happens (32:24) Lightning Round Begins: Scrappy vs Sophisticated (32:57) Scrappy Early Days and Saving the Marriage with a Cleaner (35:04) LinkedIn Only: Scrappy Marketing That Worked (36:04) Finding the $100M-$700M Sweet Spot (38:41) Final Verdict and Where to Find Debbie (44:36) Guest Links: Website: https://www.theplagergroup.com/ LinkedIn: https://www.linkedin.com/in/dsplager/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

38. Fractional COO Beata Rouleau on Scaling Without the Bloat

Beata Rouleau is the founder of Compass Consulting, a fractional COO practice that helps tech companies between $1M and $20M in revenue build the strategies, systems, and automations that turn plans into predictable growth. She grew up in a family of six kids and lifelong entrepreneurs, was homeschooled, and worked her way from executive assistant to COO before launching Compass two years ago. In this episode, Jack and Beata dig into scrappy LinkedIn outreach that actually works, why she keeps her overhead lean, and the one thing every founder needs to rally a team around a single goal. Chapters: 0:00 - Intro and the sophisticated vs scrappy question 1:28 - Growing up in a family of six entrepreneurial kids 4:00 - What Compass Consulting actually does 6:41 - Early jobs, grades, and life homeschooled 12:09 - From executive assistant to founding Compass 15:49 - ICP evolution and landing the first client 20:51 - Scrappy LinkedIn marketing that actually works 24:32 - Cash flow, bartering, and staying lean 30:46 - The one goal every team should rally around 34:41 - Lightning round: scrappy or sophisticated Connect with Beata: https://heycompass.co https://www.linkedin.com/in/beata-rouleau/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

37. Sophisticatedly Scrappy: 10 Years of Beyond the Chaos with Susan Fennema

Jack sits down with Susan Fennema, the self-proclaimed "Chaos Eradicating Officer" and founder of Beyond the Chaos, to find out if she is more sophisticated or more scrappy after 10 years in business. Susan shares how she fired her first client within four months, why every small business hits a wall at 4-5 employees, her strict "get paid up front" policy, and how she has built her team so the company runs smoothly whether she is in the office or not. They also dig into her take on EOS, the scrappiest marketing moves she has tried, and a rapid-fire round covering monitors, business cards, and inbox habits. Chapters: - 00:00 - Sophisticated or Scrappy? Susan's Opening Answer - 01:33 - Growing Up in a Family of Entrepreneurs - 06:38 - Starting Beyond the Chaos in 2016 - 08:48 - Firing Her First Client in Four Months - 11:33 - Why Businesses Break at 4-5 Employees - 16:21 - Delegate vs Abdicate and Setting Expectations - 17:10 - Susan's Take on EOS - 22:38 - The First Hire and Getting Out of the Weeds - 23:23 - Getting Paid Up Front and Tapping the Line of Credit - 27:54 - Lightning Round: Monitors, Business Cards, and Inbox Habits - 41:11 - Where to Find Susan and Beyond the Chaos Guest Links: Website: https://beyondthechaos.biz LinkedIn: https://www.linkedin.com/in/susanfennema/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

36. Why Relationships Beat Sales Pipelines with Anna McGovern

Anna McGovern spent 23 years climbing the ranks at Unilever, from local supply chains all the way to global, before trading Park Avenue for her own consulting practice. As founder of Pondview Consulting, she now helps mid-market companies and private equity backed brands turn supply chains into a competitive advantage instead of a liability. In this episode, Anna and Jack dig into why "anti-fragile" beats "resilient," how she built a negotiating edge without cigars, golf, or poker, and the real story of leaving a W-2 paycheck to bet on herself, twice. Chapters: * Meet Anna McGovern, founder of Pondview Consulting * Growing up the daughter of immigrant entrepreneurs * Psychology major to Unilever procurement, the unlikely path * 23 years at Unilever, from local to global supply chains * What she teaches college students about supply chain careers * Anti-fragile vs resilient, the thesis behind her book * Building trust with suppliers without cigars, golf, or poker * Starting Pondview, COVID, and the leap to going all in * How relationships built her client base from day one * Scrappy vs sophisticated lightning round Connect with Anna: Website: https://pondviewconsulting.com/ [https://pondviewconsulting.com/] LinkedIn: https://www.linkedin.com/in/annamcgovern/ [https://www.linkedin.com/in/annamcgovern/] X: https://x.com/annamcgovern_sc [https://x.com/annamcgovern_sc] Instagram: https://www.instagram.com/anna_supplychainexpert [https://www.instagram.com/anna_supplychainexpert] Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] Company: https://www.pineapplecf.com [https://www.pineapplecf.com] Speaking: https://www.pineappleanalyst.ai [https://www.pineappleanalyst.ai] YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

35. What Buyers Actually Look for in a Business with Eric Harrison

Eric Harrison spent his entire life in the women's shoe business, growing up in his family's wholesale distribution company before taking over from his dad in 2008, right before the financial crisis hit. He sold the business to his brother in September 2019, just six months before COVID changed everything. Now he's the Director of Business Development at DBG Advisors, where he helps business owners maximize the value of their companies before they sell. Eric and Jack get into the family business lessons Eric learned (and unlearned), what it actually felt like to hand over a company he'd run his whole adult life, and why some businesses are flat out unsellable. Eric also breaks down the real dollar difference between a business with systems and processes in place versus one running on gut instinct alone, and it's bigger than you'd think. Chapters: 00:00 Scrappy or sophisticated, Eric's early verdict 02:00 Selling newspapers and candy bars as a kid 06:20 Lessons learned and unlearned from his parents 08:06 Growing up inside the family wholesale shoe business 12:37 Taking over the company in 2008 right before the crash 13:18 Selling the business to his brother in 2019 22:05 The hardest years and the leanest budgets 24:15 What MA advisor Eric would tell business owner Eric 27:01 Bringing data and Tableau into a gut feel business 32:19 The real valuation gap between systems and chaos 40:08 Inbox habits and the scrappy vs sophisticated verdict Eric Harrison: DBG Advisors: https://dbgadvisors.com/broker/eric-harrison/ LinkedIn: https://www.linkedin.com/in/ericharrisonbam/ LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Pineapple Analyst: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng