Scrappy but Successful [Consultant's Personalities When No One's Watching]

Pineapple Jack
  • 5.0 (1)
  • Entrepreneurship
  • Updated Weekly

This isn't your typical business podcast. It's a business-and-comedy crossover for consultants, fractional CFOs, advisors, and service-based entrepreneurs who are building real consulting businesses. We talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where our guest came from, dig into the early (often messy) days of their career, and unpack how their personality shows up in their business today — from client relationships and boundaries to pricing decisions and growth strategy. We'll determine whether they're scrappy or sophisticated through a series of fun stories and rapid-fire questions that reveal how they really operate behind the scenes. Along the way, we pull random questions, laugh at corporate nonsense, solve an actual data or analytics problem, and get to know their business in a way they've never described it before. You'll hear real conversations about consulting challenges, scope creep, decision-making, and how data-driven thinking supports smarter business growth. No fluff. No canned answers. Just fun, genuine conversation, with a dash of entrepreneurial lessons you can actually apply to your own consulting business. Because people listen more when you're having fun. And people do business with people they actually like. ABOUT JACK TOMPKINS & PINEAPPLE CONSULTING FIRM Jack (aka "Pineapple Jack") is the host of Scrappy but Successful, a professional speaker, and the founder of Pineapple Consulting Firm. As one of the early Fractional Analysts, Jack brings his clients' data to life with storytelling visuals and impactful insights while adding a sense of humor that makes analytics actually fun. You'll see that fun come through in spades on Scrappy but Successful as he aims to bring out the guest's personality through laughter and stories, while giving listeners some pretty useful takeaways along the way. Head to https://www.pineapplecf.com/ to turn your data into visual, understandable, decision-driving insights.

  1. 8h ago

    43. Stop Chasing Leads and Start Generating Clients with Lindsey Wagnon

    Lindsey Wagnon left a thriving corporate marketing career in 2019 to build Lindsey Wagnon Marketing, and she has spent the years since helping small and mid-sized businesses break through what she calls the "Valley of Death" - the revenue plateau that stalls so many founders. In this episode, Jack and Lindsey dig into her Southwest Virginia upbringing, the sales instincts she picked up from her dad, why she walked away from a promising corporate marketing role six months before COVID hit, and how her practice evolved from full-service execution into true fractional CMO leadership. They also get into the difference between lead generation and client generation, the clients she wishes she'd never taken on, and a lightning round covering inboxes, docking stations, and office quirks (yes, there's a piano involved). Chapters: 00:00 - Intro and the scrappy vs sophisticated question 03:17 - Growing up in Southwest Virginia and her dad's sales instincts 08:22 - Networking anxiety and how to exit a conversation gracefully 12:16 - Leaving corporate in August 2019 to go out on her own 19:41 - Pushing back in corporate and why she'd be a bad employee now 24:05 - Finding her ideal client and what the Valley of Death looks like 29:14 - Systems, ownership, and lead generation vs client generation 35:36 - Lightning round: inbox habits, desk setup, and office quirks 43:51 - Scrappy vs sophisticated verdict and what's next for her business Connect with Lindsey Wagnon: https://www.linkedin.com/in/lrwagnon/ https://lindseywagnon.com https://www.instagram.com/lindseywagnonmarketing Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  2. 8h ago

    42. Why Your Money Mindset Is Costing You Six Figures with Joel Salomon

    Joel Salomon spent years managing hundreds of millions of dollars on Wall Street, including a stretch at Citigroup where he generated positive returns in 2008 while the market fell 40%. Today he's a Prosperity Coach known as "The Money Doctor," helping heart-centered entrepreneurs (yoga teachers, energy healers, coaches) fix their money mindset and finally charge what they're worth. In this episode, Joel and Jack talk about the "money thermostat" that keeps people stuck at whatever income they grew up believing was normal, why undercharging is really a self-worth problem, and the wild story of launching his own hedge fund with zero committed capital and faking it until the money actually showed up. Chapters: 0:00 Intro and scrappy vs sophisticated 1:47 Growing up with entrepreneurial parents and a shifting money mindset 8:49 Early jobs, first money memories, and lessons on the value of a dollar 15:32 Landing the dream job at Citigroup right before the 2008 crash 21:41 Getting laid off and launching a hedge fund with no money lined up 25:01 Acting as if: faking momentum until the funding came through 27:54 From managing $700 million to coaching a $50-an-hour rate increase 31:54 The money mindset issue behind clients who don't track their own numbers 36:39 Gratitude, happy habits, and rewiring your brain for prosperity 39:59 Lightning round and final scrappy vs sophisticated verdict Joel Salomon: Website: https://www.salaurmor.com/ LinkedIn: https://www.linkedin.com/in/joel-salomon/ Facebook: https://www.facebook.com/JoelProsperitySalomon Facebook: https://www.facebook.com/thejoelsalomon Instagram: https://www.instagram.com/joelprosperitysalomon/ TikTok: search "joelprosperitysalomon" TEDx Talk: https://www.youtube.com/watch?v=0QgT2FmqmfA Jack Tompkins: 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

  3. 8h ago

    41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier

    Mark Masquelier is the founder of Owl Point, a fractional CFO and COO advisory firm helping CEOs and boards navigate business growth through financial planning, cost-saving initiatives, profitability, and strategic organizational efficiency. Mark started his career at PricewaterhouseCoopers before moving through Chicago, Tucson, and now Oceanside, California, building his consulting practice through three iterations along the way. In this episode, Mark and Jack talk about what it really means to prove your value as a fractional executive every single week, why Mark always tries to make himself replaceable, and how a stint in stand up comedy and a Saturday morning radio show became some of his scrappiest lead generation tools. They also dig into contracts versus trust, the ants that humbled his RV lifestyle, and how OwlPoint got its name. Chapters: 00:00 Introduction and fun fact about Oceanside 01:14 Scrappy on the inside, sophisticated on the outside 02:37 Six weeks in an RV and an ant invasion 09:40 Growing up one of six entrepreneurial siblings 16:33 From CPA to fractional CFO and COO 18:02 Proving weekly value to CEOs and boards 24:38 Scrappy marketing: flyers, cold calls, and a radio show 30:00 Naming OwlPoint and the CFO to COO pivot 34:20 Lightning round: contracts, mornings, and cracked screens 43:41 Closing thoughts and where to find Mark Mark Masquelier LinkedIn: https://www.linkedin.com/in/mark-masquelier-cpa-296984196/ Consulting: https://owlpoint.net/ Jack Tompkins 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

  4. 9h ago

    40. Scrappy Roofer to Executive Coaching with Andy Brown

    Andy Brown grew up carrying shingles up a ladder at eleven years old on his family's roofing crew in North Louisiana. Thirty years later, he's a Fractional COO and Executive Coach who built LULO Coaching from zero to eighteen clients in three months, then had to figure out how to scale a coaching business without burning himself out in the process. In this episode, Andy walks through his path from Walmart shop manager at twenty years old to commercial roofing COO to founder, the exact three-step process he used to land his first clients after getting laid off, and why he decided to give away half his revenue to hire other coaches instead of staying a solo practitioner. He also breaks down the faith-based operating system he's building to fill gaps he sees in EOS, and previews the executive forums LULO is launching this year as a lower-time-commitment alternative to groups like EO and Vistage. Chapters: 00:00 - Intro and scrappy vs sophisticated 00:58 - Growing up on job sites in North Louisiana 02:08 - Carrying shingles at eleven, roofing by thirteen 05:17 - Walmart, promoted at twenty, and his father's death 09:52 - Turning around a last-place store in six weeks 16:19 - Getting laid off and starting LULO in seven weeks 19:08 - Three-step process for landing first clients 21:04 - Scaling past 18 clients by hiring other coaches 24:19 - Building Vital, a faith-based alternative to EOS 27:13 - Launching executive forums as a rival to EO and Vistage 34:01 - Lightning round: books, couches, and celebrating wins Andy Brown: LinkedIn: https://www.linkedin.com/in/andybrown220/ Website: https://lulocoach.com/ Jack Tompkins: 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

  5. Jul 12

    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

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

  6. Jul 12

    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

    38. Fractional COO Beata Rouleau on Scaling Without the Bloat

  7. Jul 12

    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

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

  8. Jul 12

    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/ LinkedIn: https://www.linkedin.com/in/annamcgovern/ X: https://x.com/annamcgovern_sc Instagram: https://www.instagram.com/anna_supplychainexpert Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineappleanalyst.ai YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

    36. Why Relationships Beat Sales Pipelines with Anna McGovern
See All (44)

Ratings & Reviews

About

This isn't your typical business podcast. It's a business-and-comedy crossover for consultants, fractional CFOs, advisors, and service-based entrepreneurs who are building real consulting businesses. We talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where our guest came from, dig into the early (often messy) days of their career, and unpack how their personality shows up in their business today — from client relationships and boundaries to pricing decisions and growth strategy. We'll determine whether they're scrappy or sophisticated through a series of fun stories and rapid-fire questions that reveal how they really operate behind the scenes. Along the way, we pull random questions, laugh at corporate nonsense, solve an actual data or analytics problem, and get to know their business in a way they've never described it before. You'll hear real conversations about consulting challenges, scope creep, decision-making, and how data-driven thinking supports smarter business growth. No fluff. No canned answers. Just fun, genuine conversation, with a dash of entrepreneurial lessons you can actually apply to your own consulting business. Because people listen more when you're having fun. And people do business with people they actually like. ABOUT JACK TOMPKINS & PINEAPPLE CONSULTING FIRM Jack (aka "Pineapple Jack") is the host of Scrappy but Successful, a professional speaker, and the founder of Pineapple Consulting Firm. As one of the early Fractional Analysts, Jack brings his clients' data to life with storytelling visuals and impactful insights while adding a sense of humor that makes analytics actually fun. You'll see that fun come through in spades on Scrappy but Successful as he aims to bring out the guest's personality through laughter and stories, while giving listeners some pretty useful takeaways along the way. Head to https://www.pineapplecf.com/ to turn your data into visual, understandable, decision-driving insights.

Information