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

Pineapple Jack
  • 5.0 (2)
  • 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. 5d ago

    52. Six Months on the Floor, Then a Business with Jocelyn Singer-Sargent

    Jocelyn Singer-Sargent is the founder of Jocelyn Singer-Sargent Consulting, known as "the work whisperer." She's an HR consultant, coach, and speaker based in Santa Fe, New Mexico, dual-credentialed as a Licensed Clinical Social Worker and a SHRM-certified HR professional. Her practice spans fractional HR leadership, manager training, employee engagement, and coaching for leaders who want to build people strategies that actually work, including her work on building collaboration "from Boomers to Zoomers." In this episode, Jocelyn and Jack dig into how she stumbled into HR from a background in clinical social work, why the "employee handbook" is really a mirror of company culture, and how she built her entire consulting practice on word of mouth with zero family entrepreneurial background to draw on. She also gets into the moment she burned out of corporate HR, slept on the floor with her dogs for six months, and used a borrowed contract template to land her first client. It's a scrappy story from start to finish. Chapters: 0:00 Welcome and Santa Fe fun fact 1:09 Jocelyn's scrappy small town roots 2:46 Growing up in a no entrepreneurs household 6:34 What Jocelyn does for businesses today 9:19 Who her clients are and the 50 employee turning point 11:34 From clinical social work to accidental HR 20:00 Reading a company through its employee handbook 28:24 Burnout, the floor nap era, and starting the business 36:25 Referrals, the dog park network, and speaking engagements 40:07 Scrappy vs sophisticated lightning round Jocelyn Singer-Sargent's Links: Website: http://www.jocelynsingersargent.com LinkedIn: http://www.linkedin.com/in/jocelyn-singer-sargent-lcsw-shrm-cp-47399849 Jack Tompkins' Links: 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

  2. 5d ago

    51. Lawyer, Auditor, Fractional CFO: The Scrappy Path with Rob Bankey

    Rob Bankey is the founder of Bankey & Co., a Washington, DC fractional CFO and transaction advisory practice serving growth-stage SaaS, fintech, and AI companies. He led Contactually through its acquisition by Compass and steered Opower through its NYSE IPO before Oracle bought the company, and in 2023 DCA Live named him one of DC's Tech CFO Stars. In this episode, Rob and Jack trace his path from an Arthur Andersen offer that evaporated in the firm's collapse, through Big 4 audit work counting inventory at GM and ConAgra, to law school and a brief stint at the SEC that convinced him he wanted to build things rather than review them after the fact. Rob explains how he ended up running finance at an early-stage startup that eventually IPO'd on the NYSE, why he decided to start his own practice instead of chasing another corporate finance track, and how he thinks about proving ongoing value to clients once the systems are running smoothly ("the trains run on time"). They also get into his golden rule for startup timelines, how he built his ICP through simple word-of-mouth referrals, and a lightning round covering everything from color-coded bookmark folders to how many client inboxes one CFO can realistically manage. Chapters: 0:00 Intro and Scrappy vs Sophisticated 1:43 Growing Up Around the World 7:03 Notre Dame, Japanese, and Landing at Arthur Andersen 10:14 Big 4 Auditing: GM, ConAgra, and the Limits of Audit 13:03 Law School, the SEC, and Finding His Way Back to Finance 17:15 Taking a Startup from First Audit to NYSE IPO 19:45 Starting His Own Fractional CFO Practice 24:59 Proving Value: "The Trains Run on Time" 33:20 Lightning Round: Inside Rob's Office and Inbox 40:55 What's Next and Closing Thoughts Rob Bankey: Website: https://www.bankey.co/ LinkedIn: https://www.linkedin.com/in/rob-bankey-3268561/ 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. Aug 9

    50. The NFL, Wall Street, Hollywood, and The Standard with Cris D'Annunzio

    Cris D'Annunzio believes the greatest enemy of performance isn't failure, it's drift. He's the founder of Mettle & Method, and his resume reads like four different careers stitched together: NFL player, Wall Street broker, Hollywood actor, and high performance sales coach. Along the way he built "The Standard," a philosophy built on a simple idea: everything decays without deliberate maintenance, so you measure where you are, set a standard, and defend it every single day. In this episode, Cris walks through an incredible family story that starts with his grandfather surviving a concentration camp in Italy and ending up as a NYC parks gardener, an 18 month cold calling grind on Wall Street where he dialed the phone 250 times a day for 18 straight months, and the honest, sometimes uncomfortable difference between chasing goals and defending standards. He also talks about his work with The CFO Project, training bookkeepers and accountants to become advisors who help small businesses survive past the five year mark. Chapters: 0:00 Scrappy or sophisticated: Cris weighs in 1:49 Immigrant roots and a hard beginning 6:07 What Cris does today 7:16 His grandfather's story from Naples to Brooklyn 14:43 From the NFL to Wall Street 19:36 250 dials a day for 18 months 24:13 Building "The Standard" 26:26 Goals versus standards 39:00 The one thing that makes a high performer 45:06 Lightning round: scrappy vs sophisticated 47:56 Replayer, The CFO Project, and closing thoughts Cris D'Annunzio's Links: Mettle & Method: https://www.mettleandmethod.com The CFO Project: https://cfoproject.com LinkedIn: https://www.linkedin.com/in/cris-d-annunzio/ Jack Tompkins' Links: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Pineapple Analyst AI: https://www.pineappleanalyst.ai YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

  4. Aug 9

    49. Turning Donor Gifts Into Loyalty That Lasts with Alison Jeffrey

    Alison Jeffrey is the founder of Alison Jeffrey Consulting, a fundraising strategy practice working exclusively with nonprofits. After 25+ years in the sector, including years spent in-house, she left a permanent role five years ago to build a boutique consulting practice, working deeply with about 15 clients instead of chasing volume. On this episode, Alison and Jack dig into what it actually means to ask people for money for a living, from six-figure stethoscopes to the emotional weight behind a $10,000 ask. Alison shares the story of engraving a $100 stethoscope for a billionaire donor (and the handwritten note that came back), why she thinks "philanthropy is self-care," and how she built a practice around being the strategist in the room, not just the person who closes the gift. Jack and Alison also get into a lightning round of scrappy vs sophisticated questions covering everything from grades in school to her minimalist home office. Chapters: 0:00 Sophisticated or scrappy: Alison's 80-20 rule 2:15 Uncle Joe and the Glasgow china shop 5:52 The engraved stethoscope story 11:24 Growing up in a political but non-entrepreneurial family 13:12 The COVID balcony story that still gets brought up at home 16:00 Setting strategy vs doing the solicitation herself 18:13 Why fundraising isn't really a sales process 24:19 Quitting her job, losing her father, and landing her first client 30:25 Becoming known as the strategist, not just the fundraiser 32:41 Lightning round: scrappy vs sophisticated Alison Jeffrey's links: Website: https://www.alisonjeffrey.com/ LinkedIn: https://www.linkedin.com/in/alisonjeffrey/ Jack Tompkins' links: 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. Aug 9

    48. From Goldman Sachs to Fractional CFO for Small Business with Oscar Casanova

    Oscar Casanova is the founder of Eververdant Growth Partners, a fractional CFO advisory firm helping lower middle-market business owners make sharper financial decisions. Before starting his own firm, Oscar closed over $30 billion in deals across Goldman Sachs, high-growth startups, and Shopify - and he brings that same rigor to the small businesses that make up the backbone of the economy. In this episode, Jack and Oscar dig into Oscar's journey from growing up in Mexico to landing at Goldman Sachs on his fifth application attempt, why he walked away from the corporate path to build something of his own, and the "operating system" mindset he uses to run his life and his firm. They also get into how he actually wins clients (hint: it is not by chasing outcomes), what makes someone coachable, and a full lightning round of scrappy versus sophisticated questions. Oscar lands the verdict for himself by the end - you will have to listen to find out which side he falls on. Chapters: 0:00 Welcome and fun fact of the day 1:02 Scrappy or sophisticated - Oscar's answer 1:45 Growing up in Mexico and coaching basketball 5:01 What Eververdant Growth Partners does today 5:38 Leaving Mexico for the US in 2011 8:20 Scrappy rapid fire - Tupperware and the four meals 11:23 The "operating system" for life and fitness 12:00 Getting into Goldman Sachs on the fifth try 17:47 Finding Eververdant's first clients through curiosity 23:39 Surrendering the outcome instead of chasing it 30:10 Earning trust as a CFO advisor 35:04 Lightning round - office, inbox, and airport habits 40:04 Final scrappy versus sophisticated verdict Oscar Casanova: LinkedIn: https://www.linkedin.com/in/oscar-casanova-c/ Eververdant Growth Partners: https://eververdantgrowthpartners.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

  6. Aug 2

    47. From Homebuilder to Fractional CFO: 30 Years of Scrappy Lessons with Mark Dunaway

    Mark Dunaway spent 30+ years leading finance and operations for some of the country's top residential homebuilders - and then walked away from all of it to build a fractional CFO market from scratch on the Gulf Coast. As Area President and Fractional CFO for FocusCFO, he covers coastal Alabama and Pensacola, FL, a territory with zero prior FocusCFO presence and a market that often can't distinguish a CFO from a CPA. In this episode, Mark unpacks what strategic financial leadership actually looks like for small businesses, why hope is not a strategy, and how he's doing it all the old-fashioned way: five to seven face-to-face meetings a week. We cover Mark's path from a Baptist minister's son in southeastern Kentucky to bagging groceries, doing a six-hour solo Sunday radio show, and eventually running divisions for some of the largest homebuilders in the country. Along the way, he learned that great CFOs don't just live in spreadsheets - they have to understand the field, the bank's perspective, and the owner's vision all at once. If you're a small business owner trying to figure out whether you need a CPA, a bookkeeper, or something more, this episode is the clearest explanation you'll find. Chapters: 0:00:00 Intro and Mobile Mardi Gras Fun Fact 0:01:23 From Kentucky to the Coast: Mark's Background 0:02:57 What Fractional CFOs Do (and the Three-Headed Monster) 0:07:38 CFO Mindset vs. Accounting: Two Different Worlds 0:12:31 First Jobs: Bagging Groceries and a Six-Hour Radio Show 0:18:54 Building FocusCFO's Gulf Coast Market from Scratch 0:24:11 CFO vs. CPA: Keeping the Plates Spinning 0:27:18 Breaking Goals into Weekly Wins - Hope Is Not a Strategy 0:30:56 Finance's Role in Sales Strategy 0:33:05 Lightning Round: Scrappy vs. Sophisticated Connect with Mark Dunaway: Mark's LinkedIn: https://www.linkedin.com/in/mark-dunaway/ 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

  7. Aug 2

    46. Blind Spots, Business Therapy, and the Art of Scrappy Leadership with Sean McColl

    Sean McColl is the founder of Trusted Business Advisors in Charleston, South Carolina. After more than 20 years as a top-performing sales leader - selling pagers in Washington, DC during the crack epidemic, building accounts at AT&T, and growing a promotional products company from a tiny startup to a successful acquisition - he went independent as an outside advisor. Today he works with owners, successors, and key leaders to bring the objectivity that insiders can't generate on their own, helping businesses find their blind spots and build sustainable growth. In this episode, Sean takes us from early childhood hustles - cutting lawns at 11, running a babysitting operation with his sister, and learning hard lessons as a 14-year-old dishwasher at an Italian restaurant - all the way through decades of high-stakes sales leadership and into what it really means to be a "business therapist" who helps CEOs sleep better at night. He shares why the very traits that make great entrepreneurs successful are often what hold them back as they scale, how the Who Not How principle shows up in his daily advisory work, and why an outside perspective is the most undervalued asset any growing business can have. Chapters: 0:00:00 Welcome + Sean's Entrepreneurial Roots 0:04:13 From Lawn Mowing to Babysitting Dynasties 0:07:02 First Real Job and the Restaurant Reality Check 0:09:58 Selling Pagers in 1990s DC - Scrappy by Necessity 0:18:26 Building Trusted Business Advisors 0:21:05 Coaching Owners Out of Their Own Way 0:29:17 Who Not How - Building the Right Team 0:31:32 The "Business Therapist" + Proving Value 0:34:31 Scrappy vs. Sophisticated Lightning Round 0:40:14 What's Next + Final Thoughts Connect with Sean McColl: LinkedIn: https://www.linkedin.com/in/seanmccoll1/ Website: https://trustedbizadv.com/ Connect with 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

  8. Aug 2

    45. From CNC Shops to Saudi Royalty: How Minds on Fire Got Here with Marcus Gaughan

    Marcus Gaughan started his entrepreneurial journey at 19 with a portable eye therapy device that nearly launched with Iris as a strategic partner - until a single email ended it all. From there he built Minds on Fire through incubators, a CNC manufacturer marketplace, and a pandemic-era pivot that took him from Southern Ontario to investor conferences in the Middle East - picking up a client who happened to be the son of the governor of Riyadh along the way. Today Marcus runs Minds on Fire as a scaling agency focused on agentic AI, building custom tools that help businesses save time (defensive AI) and drive growth (offensive AI). His take: the real money is in the defensive side, and getting AI into your business doesn't have to break the bank or replace anyone. He's building a self-serve agent platform to prove it. Chapters: 0:00:00 Welcome & Meet Marcus Gaughan 0:00:36 Scrappy or Sophisticated? 0:02:35 Growing Up in Ontario's Startup Scene 0:05:36 First Startup: Portable Eye Therapy Device 0:11:01 A Decade of Business Partners 0:21:00 2020 Reset: Pandemic Pivot 0:24:38 Fake It Till You Make It in Bahrain 0:33:39 Minds on Fire: Agentic AI Agency 0:37:19 Offensive vs. Defensive AI 0:39:15 Lightning Round Connect with Marcus: https://agent.mindsonfire.ca/ https://www.linkedin.com/in/marcusgaughan/ 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

See All (53)

Ratings & Reviews

5
out of 5
2 Ratings

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