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

Ron Latz is the founder of LegalFenix, a fractional CMO and marketing advisory firm that works exclusively with law firms. After more than 15 years in legal marketing, including stints at FindLaw and Mockingbird Marketing, Ron built LegalFenix into a vendor-neutral shop that helps firms sort out what is actually working in their marketing and what is not. In this episode, Ron and Jack cover Ron's path from a metal band and umpiring Little League games in New Jersey to running a marketing consultancy built entirely around law firms. They dig into why Ron refuses to take referral fees, how his hiring process still ends with him flying out to meet every candidate in person, and the KPIs his team leans on to prove value to clients month after month. Along the way: dot-net domains, the credit card timing game, and eating cereal out of clean Tupperware. Chapters: 0:00 Welcome and the scrappy or sophisticated question 1:08 Growing up in New Jersey and an early love of hockey 3:31 Garage sales, fundraising calls, and a band in the emo days 7:42 What LegalFenix does for law firms today 8:47 Landing on legal marketing and staying vendor neutral 10:39 From Xerox to FindLaw to starting Athlete Consulting 14:30 Three name changes and finally landing on LegalFenix 16:35 Leaving agency life and going vendor neutral for good 27:01 Proving value to clients and the KPIs that matter 32:01 Scrappy versus sophisticated lightning round 43:40 Where to find LegalFenix and final thoughts LegalFenix website: https://legalfenix.com Ron Latz on LinkedIn: https://www.linkedin.com/in/ronlatz/ Jack Tompkins on 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

Katie Bedford spent seven years as an aerospace engineer building space robotics before pivoting through digital agencies, project management, and five years as a fractional COO to land where she is today: a strategic advisor and thinking partner for agency leaders. She's the founder of K Bedford Consulting in Vancouver, and her whole approach is built on giving business owners the honest, unbiased conversation they can't get from anyone else on their team. In this episode, Katie and Jack dig into how an engineering brain wired for risk and rigorous logic became the perfect training ground for advisory work, why so many small businesses mistitle their staff, the real difference between AI-as-pattern-finder and AI-as-judgment-maker, and the emotional weight of helping leaders make the calls they already know they need to make. Katie also shares two tools she built herself using AI (a custom CRM and a cash flow forecaster) and makes a genuinely useful case for why chasing AI tools without a centralized dataset is putting the cart before the horse. Chapters: 0:00 Scrappy or sophisticated: Katie's answer 1:29 Cinder blocks, jewelry, and Katie's non-entrepreneurial roots 4:13 What a thinking partner actually does 7:33 How the advisory relationship gets structured 9:41 Why small companies over-title their people 13:40 From grade one space obsession to aerospace engineer 14:41 NASA, the Canada Arm, and getting the "get out of jail free" layoff 16:43 The pivot into agency life and finding the thinking partner niche 20:36 Where AI actually helps (and where it can't) 24:04 Building her own CRM and cash flow tool with AI 27:23 The overbuilt website and the box of unused business cards 29:20 Her one scrappy money story: fighting for a business credit card 34:02 The Steve Martin mindset and Katie's rotating hobbies 36:08 Broadening her niche beyond digital agencies 43:09 The Thinking Partner ROI calculator Katie Bedford: LinkedIn: https://www.linkedin.com/in/katie-bedford/ 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

Aaron Gutowski is a Partner and Chief Sales Officer at Chief Outsiders, an "Executives-as-a-Service" firm that places fractional CMOs and CSOs inside mid-market companies. He was one of the first CSOs to join the firm, and he brings more than 20 years of sales leadership experience across data, research, and industrial services to every engagement. In this episode, Aaron traces his sales instincts back to a Detroit News paper route as a kid, then walks through the hustle that got him his first real sales job selling computers at a company that's now Verizon, including the time he secured a shipment of Apple computers with a PO number made up of his own birthday. He and Jack dig into how Aaron landed his first major client at Chief Outsiders, why the single most important KPI in any sales org is the number of new first meetings (not total meetings), and why honest, sometimes uncomfortable conversations with clients build more trust than telling them what they want to hear. Chapters: 0:00:00 Intro and meet Aaron Gutowski 0:01:10 Scrappy all the way, growing up in Detroit 0:03:13 The Detroit News paper route hustle 0:06:09 What a fractional CSO actually does 0:09:43 Landing HBS Solutions, his first big client 0:14:45 Selling Apple computers and the birthday PO hustle 0:29:47 Coaching honesty into hard sales conversations 0:31:15 The one KPI that predicts sales success 0:35:10 Lightning round and Chief Outsiders AI program Connect with Aaron Gutowski: LinkedIn: https://www.linkedin.com/in/aarongutowski/ Chief Outsiders profile: https://www.chiefoutsiders.com/profile/aaron-gutowski 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

Tina Ruark-Baker has already built and sold two companies, spent two decades climbing to the C-suite, and then walked away from the corner office to start a third business from scratch. Today she runs TRB Creative, coaching small businesses, entrepreneurs, and nonprofits on the one channel she believes almost nobody uses correctly: LinkedIn. In this episode, Tina and Jack trace her path from a staffing company she started at 18 in her dad's basement, through 20 years in New York City, to her current life at the beach in a golf community outside Charlotte. She breaks down why personal LinkedIn profiles outperform company pages, why she said yes to painting an entire medical office (20 canvases, zero prior experience), and how nine different revenue streams stay connected through a single referral-driven philosophy: make the connection, then get out of the way. Chapters: 0:00 Intro and the scrappy vs sophisticated verdict 1:35 From Detroit hustle to two exits by 1999 3:25 New York, a chance encounter, and 20 years in the city 6:32 Walking away from corporate to coach LinkedIn 9:11 Landing first clients through networking 14:23 Saying yes to a 20-painting art commission 18:18 Nine revenue streams and the power partner network 21:13 Finding the real ICP and ditching marketing-only work 25:23 Scrappy marketing, golf, and keynote speaking 30:45 How Tina measures success and builds client trust Connect with Tina Ruark-Baker: LinkedIn: https://www.linkedin.com/in/tina-ruark-baker/ TRB Creative: https://www.trbcreative.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

John Buckner is the founder of Insightful Selling and a Fractional VP of Sales advisor at Sales Xceleration, bringing a thirty-year corporate sales and marketing career to small businesses that need to grow. His resume includes DuPont, Chick-fil-A, 7-Eleven, Walmart, and Home Depot, but John calls himself an "accidental salesman" - his path started on his father's land surveying crew in the North Carolina foothills, not a sales floor. In this episode, John and Jack dig into why the best salespeople act as guides instead of salesmen, with the customer as the hero of their own story. John shares the data-driven pitch that won Chick-fil-A's coffee business away from 23 other roasters, the pharmacy counter interaction that taught him what trust-based selling actually looks like, and why he built his whole practice around single, focused solutions instead of overwhelming clients with everything he offers. Chapters: 0:00 Welcome and the Lake Norman monster fun fact 0:42 Scrappy or sophisticated - John's 300 CEO outreach push 6:03 Family roots - a land surveyor dad and the family entrepreneurial itch 10:32 Reframing sales - the customer as hero, John as guide 13:44 The shingles shot story - trust-based selling in action 18:24 Early sales instincts - basketball, retail spiffs, and rapport 22:02 Winning Chick-fil-A's coffee business with data and insight 28:20 Getting out of the box - curating your offer instead of overwhelming clients 34:46 Lightning round - garage sales, cash flow games, and inbox habits 40:22 Final takeaway - make the customer your true north John W. Buckner brings a broad sales and growth background from a thirty-year corporate career, including leadership roles as VP of marketing and SVP of sales, spanning Fortune 500 companies, national middle-market firms, and major retailers including DuPont, Georgia-Pacific, Simpson Strong Tie, Chick-fil-A, Taco Bell, Sonic, 7-Eleven, Walmart, Target, Home Depot, and Lowe's. His firm, Insightful Selling, helps small businesses win through people, process, and technology. https://LinkedIn.com/in/johnwbuckner https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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

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

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

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

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

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

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

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

Priscilla McKinney is the CEO ("Momma Bird") of Little Bird Marketing, a LinkedIn influencer, a trained cultural anthropologist, and the host of her own podcast, 450-plus episodes deep. She joins Jack to unpack her take on the show's central question: you personally have to be scrappy, but your systems need to be sophisticated, meaning simple, clear, and pared down, not loaded up with bells and whistles. That distinction runs through everything from how she sets up her team's scope of work to how she rebuilt her agency from the ground up. From selling her mom's tulips door to door at age seven to surviving a 2011 tornado that leveled a third of her town, followed three weeks later by her studio burning to the ground, Priscilla has bet on herself again and again. She talks candidly about nearly losing the business three times, what entrepreneurship really costs a marriage and a family, and why being busy is not a badge of honor. Then Jack hits her with a scrappy vs sophisticated lightning round covering credit card timing games, scope creep, and the messiest client mistakes. Chapters: 0:00 Welcome and the Scrappy vs Sophisticated Question 3:23 Building a Team That Runs Itself 6:13 Born to Sell: From Tulips to the Drive-Thru 14:56 From Credit Card Hacks to Little Bird Marketing 19:04 Rising From the Ashes After the Tornado 20:19 Meet C Suite Stacy, the ICP That Never Changed 22:47 The Real Cost of Betting on Yourself 31:22 Boundaries, Trust, and the Entrepreneurial Curse 35:28 Lightning Round and Office Confessions 43:19 Final Verdict and Where to Find Priscilla Priscilla McKinney: LinkedIn: https://www.linkedin.com/in/priscillamckinney Website: https://littlebirdmarketing.com Resources and Freebies: https://littlebirdmarketing.com/resources Priscilla's Podcast: https://podcast.littlebirdmarketing.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

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

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

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

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

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

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

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

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

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

John Rodriguez is the co-founder of Valiant, a firm that embeds Big Four level financial expertise directly into startup teams instead of operating as a black box. Valiant covers everything from fractional CFO work to bookkeeping to payroll, and they specialize in seed to Series B SaaS and tech companies. In this episode, John walks through his unusual path: a disciplined, "sophisticated" start in Big Four public accounting that flipped into full scrappy mode once he went out on his own. He shares the wild origin story of Valiant, which started with zero employees, no business entity, and a single client at Zynga that his co-founder talked into a deal before the company even had a name. John also breaks down why startups increasingly expect dashboards and strategic analysis instead of just clean books, and why he intentionally builds his clients toward hiring their own in-house replacement instead of holding onto the relationship forever. Chapters: Intro and the sophisticated vs scrappy question Growing up in LA with an entrepreneurial mom Berkeley, working hard over being smart, and the Big Four grind Learning to disconnect from the badge of honor of overworking Why founders should delegate accounting and focus on their strengths The Zynga origin story: a company with no name, no employees, and one client Naming Valiant and finding the right ICP over time Why clients now expect analysis and outcomes, not just bookkeeping The hire your replacement model and why transparency builds trust Lightning round and the final scrappy vs sophisticated verdict Connect with John Rodriguez: LinkedIn: https://www.linkedin.com/in/john-s-rodriguez-35685916/ Website: https://www.usevaliant.com 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

Charlie Warden is the Managing Partner of Warden Strategy, a revenue strategy and venture-building firm based in Denver. He's a fractional CGO (Chief Growth Officer), not a CMO or CRO, and he joins Jack to talk about why that distinction matters, why he started a second fractional firm instead of scaling his first, and why he'd rather turn down growth than chase it. From running a donut resale stand and a baseball card business in middle school to founding his first agency on campus with free university software, Charlie's entrepreneurial roots run deep. He shares the early days of bootstrapping with his now-wife in a 600 square foot apartment, the hard lessons from a venture-backed hardware startup that took him to China, and how he eventually landed on the Chief Growth Officer model that breaks down the marketing, sales, and customer success silos most businesses get stuck in. Charlie also opens up about Warden Strategy's deliberately narrow ICP (the $1M-$10M B2B service businesses that fall below the private equity threshold), why "we need more leads" is almost never the real problem, and how he and his team built a studio arm for side projects they're genuinely passionate about. Then Jack and Charlie wrap with a scrappy versus sophisticated lightning round covering inbox habits, dryer sheets, and airport efficiency. Chapters: 00:00 - Scrappy or sophisticated: Charlie's take 03:43 - The donut stand and baseball card hustles 09:08 - Launching Lion Head Productions in college 14:11 - Bootstrapping on $80 grocery weeks 18:12 - The venture-backed hardware startup and the move to Denver 23:03 - Building Warden Strategy and the studio arm 26:11 - Why "Chief Growth Officer" instead of CMO or CRO 30:20 - The lead generation myth and what's really broken 33:18 - Defining (and defending) a narrow ICP 35:48 - Scrappy vs. sophisticated lightning round Connect with Charlie: LinkedIn: https://www.linkedin.com/in/charlie-warden/ Company: http://www.wardenstrategy.com 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

Jack Tompkins sits down with Alexandra Erman, a startup operator who has spent two decades building the infrastructure that lets venture-backed companies scale without breaking. Alexandra has architected people strategies, run finance, launched entities across continents, and scaled companies from $500K to $12M in ARR across 12 countries. Before any of that, she ran art galleries in Saint Barthelemy and Paris, crashed one business completely, and rebuilt from there. In this episode, Alexandra and Jack dig into her path from art dealer to fractional COO and CEO, the financial and operational chaos of running cross-border startups, and why she thinks every early-stage company needs a generalist before it needs specialists. Chapters: 00:00 - Sophisticated or scrappy: Alexandra's verdict 01:32 - Growing up in Paris and becoming an art dealer in Saint Barthelemy 07:38 - Crashing the gallery business and starting over in corporate France 11:18 - Breaking into the fractional startup world in 2005 13:46 - The cross-border medical device company and seven years untangling international finance 19:11 - Joining Agora Pulse and scaling a bootstrapped SaaS company for a decade 26:14 - The case for hiring a generalist before you hire specialists 32:23 - From Agora Pulse to StreamSets to BforeAI and the startups she runs today 40:33 - Scrappy money stories: ten euro days and pulling favors from old coworkers 49:11 - Final advice: don't wait too long to hire your key people Connect with Alexandra: https://www.linkedin.com/in/alexandraerman/ 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

Jennifer Best is the founder of Copper Compass Group, a fractional marketing firm helping small businesses and startups build real marketing strategy instead of just marketing activity. She's a two-time entrepreneur, a Certified HubSpot Partner, a past SBA award winner, a Forbes Communications Council contributor, and the incoming president of the AMA's Triangle (NC) chapter. In this episode, Jen and Jack dig into her path from corporate marketing into fractional work, how she defines and re-defines her ICP, why she'd rather refer out work than fake expertise she doesn't have, and how she's started layering AI agents into her own operations - then they run through a full Scrappy vs. Sophisticated lightning round covering everything from inbox management to Six Flags churros. Chapters: 00:00 - Intro and the Scrappy vs. Sophisticated Question Jack kicks off with a Raleigh fun fact and brings on Jen Best, founder of Copper Compass Group, who immediately claims the scrappy side of the spectrum. 01:10 - Family of Entrepreneurs and Early Jobs Jen traces her entrepreneurial streak back to her parents, plus stories from working at Six Flags and a string of early side jobs. 08:00 - The Pandemic Pivot Into Fractional Work How a cross-country move, a corporate pay cut, and a side project for a former colleague turned into the start of Copper Compass Group. 11:00 - Defining (and Redefining) the ICP Jen breaks down why ideal client profiles aren't static, how she approached persona-building before AI, and why critical thinking still has to come first. 15:30 - The Pandemic Ramen Noodle Years A candid look at the financial anxiety of buying a house and going fractional at the same time, and the "next normal" mindset that came out of it. 20:00 - Knowing When to Refer Instead of Fake It Why Jen would rather hand off work to a trusted partner than oversell her own skill set, and how that's paid off in long-term referral relationships. 24:30 - Putting AI Agents to Work Jen walks through the agents she's built with Zapier, ClickUp, and HubSpot to automate her own admin, and why she's holding back on rolling AI deeper into client work just yet. 29:30 - AI, Hiring, and the Human Touch A conversation about AI-run job interviews, new graduates entering an AI-disrupted job market, and why human expertise still wins long-term. 31:30 - Scrappy vs. Sophisticated Lightning Round Family reviews, childhood collections, infomercial purchases, QVC confessions, monitor setups, and how Jen escapes a networking conversation that's run its course. 43:00 - What's Next and Closing Thoughts Jen talks about upcoming training programs, building a fractional referral network, and leaves the audience with one piece of advice: take the leap. Jen Best: LinkedIn: https://linkedin.com/in/jenbest6 Website: https://coppercompassgroup.com Newsletter (LinkedIn): https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7292543398345867264 Newsletter (Substack): https://thebestbrew.substack.com/ Jack Tompkins / Pineapple Consulting Firm: 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

In this episode of Scrappy But Successful, Jack sits down with Natalie Hoop, a fractional COO and coach for fractional consultants, to unpack what it really takes to build a fractional business that works. Natalie shares her scrappy path from retail leadership at Blockbuster and Borders to startups, fractional operations, and coaching. Along the way, she tells wild behind-the-scenes stories about Blockbuster missing the DVD/Netflix moment, Borders handing online book sales to Amazon, and why companies often fail when they ignore the people closest to the customer. Jack and Natalie also dig into the real challenges fractional consultants face: undercharging, scope creep, weak positioning, vague ICPs, burnout, and accidentally building "another job" instead of a business. Natalie breaks down how fractionals can clarify what they solve, package their services, make better business decisions, and speak directly to the pain their clients actually feel. If you're a fractional consultant, coach, operator, or founder trying to grow without burning out, this one is packed with practical advice. Chapters 00:00 Intro: Scrappy But Successful 00:59 Natalie's scrappy roots and nontraditional path 03:34 How retail became Natalie's business education 09:14 Blockbuster's missed DVD and Netflix opportunities 13:28 Borders, Amazon, and the cost of bad strategic bets 15:00 Sunk cost fallacy and knowing when to pivot 18:04 Treating business changes like reversible decisions 23:36 Natalie's first fractional client after being laid off 27:12 Undercharging, overdelivering, and scope creep 28:04 Building the right ICP instead of another job 34:12 Positioning fractional services around real client pain 46:54 Jack gets coached on Pineapple Analyst positioning Connect with Natalie: http://nataliehoop.com/ https://www.linkedin.com/in/nataliehoop/ https://www.instagram.com/nataliehoop_ops/ 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

Paul Pompeo is a New York sales guy through and through - born and raised in Queens, started his first business running a paper route crew at age eleven, and never stopped hustling from there. Today he runs Prolan Consulting, where he helps business owners, coaches, and consultants close more of the conversations they're already having instead of chasing more leads. In this episode, Paul takes us from his blue-collar Queens upbringing (his grandfather built piano casings, his father ran plumbing for Manhattan high-rises) through his early hustles - paper routes, mobile bartending, demolition work - and into his real sales education: knocking on 70-80 doors a day in the boiler-room telecom era of the early 2000s. He shares how that door-to-door, phone-heavy grind shaped his approach to value-based selling, objection handling, and closing without being pushy, plus how those same principles translate for small business owners trying to sell today. Chapters: Growing up in Queens and the blue-collar work ethic his family instilled Running a paper route business with employees at age eleven High school side hustles - mobile bartending and demolition work Becoming an aeronautical engineer, then getting laid off and pivoting to sales Learning to sell by knocking on 70-80 doors a day in NYC and Brooklyn The boiler-room telecom era and surviving constant company collapses Taking the conversation off price and selling on value instead How to ask for the business without sounding pushy or desperate Scrappy vs. Sophisticated lightning round - business cards, lunch orders, and inbox habits What's next for Paul and how to connect with him Connect with Paul Pompeo: https://www.prolanconsulting.com https://www.linkedin.com/in/paulvpompeo/ https://breakthroughsellingwithpaul.com 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

Hey consultants and fractional professionals - this is the episode where strategy meets scrappiness. Shay Prosser founded North 12 Partners after realizing something crucial: most growing companies (think $1M-$20M revenue) are stuck between startup chaos and corporate process. They've outgrown the founder-doing-everything phase but haven't figured out the systems to scale. Shay steps in as that embedded strategic leader - the person who helps CEOs build businesses that actually work without them doing all the work. What makes this conversation special is how Shay bridges both worlds. She grew up underneath an accounting desk in her family's truck rental business in Indiana, watched her dad sell the company at 12, then went on to run large-scale events at Microsoft before realizing her real superpower wasn't logistics - it was end-to-end strategy. She even got more money working part-time as a consultant for Microsoft than she made in her full-time salary - a perfect example of knowing your worth. In this episode, we dig into her go-to-market strategy framework, why purpose-driven growth is becoming table stakes for scaling companies, and how she helps clients avoid the trap of reactive growth. We also run through our signature Scrappy vs Sophisticated lightning round covering everything from her messy cable management setup to her approach to email (spoiler: she sends herself misspelled reminders and has a Claude coach for client interactions). Chapters: Family business roots and the mafia lie (00:00 - 03:30) From Microsoft layoffs to premium consulting rates (03:30 - 07:45) Transitioning from events to strategy and realizing what you're actually good at (07:45 - 09:06) Why she left CMO role to start North 12 Partners (09:06 - 10:30) Go-to-market strategy as the missing link for growing companies (10:30 - 15:20) Data, purpose, and intentional growth frameworks (15:20 - 20:45) Why purpose-driven business beats generic mission statements (20:45 - 25:15) The scrappy office setup, cable chaos, and O-ring lighting (25:15 - 39:30) Lightweight systems and getting client responses in one business day (39:30 - 44:00) Shay's Links: https://www.north12partners.com https://www.linkedin.com/in/shayprosser Jack's Links: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Adrian Betts is the founder of Xpandur, where he helps mid-market warehouses unlock hidden capacity and drive profitability without adding headcount, equipment, or new technology. With a background leading high-volume, tight-margin operations, he specializes in eliminating bottlenecks, aligning teams, and turning chaotic warehouse floors into consistently high-performing systems. In this episode, Adrian drops analogy after analogy - and every single one lands. Chapters: 00:00 - Intro and scrappy or sophisticated 01:04 - Growing up scrappy: Atlanta roots and a family of entrepreneurs 03:51 - Early jobs, bad grades in science, and learning to show your work 07:47 - Unlearning perfectionism and the baseball batting average mindset 10:37 - From aviation dreams to consulting: the 2004 start and 2017 restart 14:23 - Building a client base through word of mouth and water cooler credibility 20:46 - ICP evolution: why Adrian now says no to Enterprise and SMB 23:39 - How Adrian actually unlocks capacity in a warehouse - the full method 27:06 - Measuring performance with throughput rates, order accuracy, and cube 32:48 - Scrappy vs sophisticated: airports, inbox chaos, and the file naming system Adrian Betts / Xpandur: https://www.linkedin.com/in/adrianbetts/ https://xpandur.com Jack Tompkins / Pineapple Consulting Firm: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Bill Wilson has built and sold two companies, helped dozens of B2B SaaS founders fix their pricing, and started a brand-new business while walking through a market in southern Spain. He joins Jack to break down why most pricing problems are actually positioning problems, what scrappy founders get wrong about churn math, and how to start a testable company in a single afternoon with AI. Chapters: 00:00 - Intro and scrappy vs sophisticated 01:09 - Growing up across Canada and the entrepreneur in the family 02:40 - First company at 18, swearing off business, then getting pulled back in 04:35 - Halifax co-working scene and the accidental birth of Mindsea 06:38 - Collaborative consortiums, committed co-discovery, and lessons from trying to share work 07:48 - How SalesRight was born from an internal tool and got acquired by FastSpring 10:19 - What Pace Pricing does - end-to-end pricing strategy for B2B SaaS 11:31 - The most common pricing problem - flatline growth, churn math, and expansion revenue 13:46 - Why pricing confidence comes from conviction, not just data 14:40 - Four levels of pricing validation and how to get there scrappily 17:32 - Jobs to be done, customer interviews, and using AI to analyze them 22:43 - AI in hiring, irresponsible NOT to use AI, and democratizing knowledge 25:40 - AI native vs AI forward, human-led AI-assisted 27:51 - Starting a business in Spain in one afternoon with Claude and landing pages 33:01 - Committed co-discovery - 90 days, 50/50, and why stealth mode is dead 35:08 - Trust as the real moat in AI businesses 37:00 - Love them, help them, pay you - the three things that matter 38:01 - Lightning round: airport anxiety, business class, couch work, inbox zero Bill Wilson Links: LinkedIn: https://ca.linkedin.com/in/wdrwilson Company: https://www.pacepricing.com Blog: https://www.pacepricing.com/blog 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

Piyanka Jain has been building AI models since 2002 - before "AI" was a buzzword. Today she's the CEO of AskEnola, an agentic AI platform that automates the entire CFO workflow: closing books, P&L reporting, MRR schedules, and investor reporting - all with high-fidelity output that doesn't hallucinate. In this episode, Piyanka talks about what 25,000 hours of building actually looks like, why she walked away from enterprise deals to chase mid-cap CFOs, and what "sophisticated in all the right ways" means when your go-to-market is still 100% scrappy hustle. Chapters: 00:00 - Sophisticated Where It Counts, Scrappy Everywhere Else 01:38 - Real AI at Scale: 7-Eleven ATMs and Kiva Donations 04:38 - Warrior Class to Business Class: Piyanka's Origin Story 07:45 - Transformation as the True Motivation 11:52 - What AskEnola Actually Does for CFOs 15:21 - 25,000 Hours, Multiple Pivots, One Winning Bet 20:15 - The SaaStr Slop Problem and the Trust Deficit 25:46 - When Do You Know It's Ready to Ship? 33:53 - Scrappy vs Sophisticated: The Rapid Fire Round 38:19 - Hustling Into the Right Rooms and Manifesting the Right Clients 44:24 - Productivity vs Presence: Slowing Down to Feel Worthy Connect with Piyanka Jain: https://www.linkedin.com/in/piyanka/ https://www.askenola.ai 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

Drew Dowd has built his career walking into broken businesses and finding the one thing everyone else missed. As founder of D2 Operations Consulting, he works with early and growth-stage companies on revenue operations, team execution, and GTM strategy - and his take is that most business problems aren't execution problems. They're information problems wearing an execution costume. Jack and Drew dig into constraint-based thinking, when to document and when not to, and what it really takes to scale a company without over-engineering it. Chapters: 0:00 - Intro and the scrappy vs. sophisticated question 1:00 - Growing up in rural Missouri and early scrappy roots 3:35 - Cold door-to-door selling discount cards in high school 4:51 - First jobs: froyo, food trucks, and a lemonade-to-burger empire 7:34 - Data-driven operations lessons from a food truck mad scientist 11:05 - How a punishment hack in elementary school predicted a systems career 13:10 - Finding the real constraint: the outbound dialing case study 17:14 - You can't prescribe dosages until you understand mechanisms 19:13 - Centralization over complexity: the simple fix for broken ops 22:04 - SOPs, trust, and the Google Doc that scaled a company to $1M/month 28:01 - Struggle days, bad calls, and failing fast 31:36 - Launch at 50% or wait for 90%? Speed vs. structure debate 34:10 - Lightning round: scrappy vs. sophisticated habits 38:00 - ADHD, notebooks, and why pen and paper beats Notion 41:47 - Defining success: profit volume, ethics, and the stabilize-vs-grow mindset 44:49 - Data tells you where to look, not what to do 45:08 - How to connect with Drew Connect with Drew Dowd: https://drewdowd.com https://www.linkedin.com/in/drewdowd/ https://x.com/DrewDowd 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

Donny Mashiach is the Founder and CEO of Warrior Group, a finance services firm helping founder-led, scaling businesses install stronger financial infrastructure through fractional CFO, bookkeeping, controller, and strategic consulting services. Donny started his entrepreneurial journey running a kosher food concessions operation at Wrigley Field before moving through investment banking on Wall Street - working on billion-dollar deals in industrials and beyond. Three years ago he founded Warrior Group and has since grown to 15 CFOs and 15 analysts, with a sharp focus on fashion and apparel brands scaling past $5M. In this episode, Donny and Jack dig into why the thing that gets you to $1M is exactly what breaks you at $10M, how to quantify every opportunity in your business, and what it actually looks like to build financial infrastructure that drives decisions - not just reports. Chapters: 00:06 - Scrappy vs. Sophisticated: Donny's Take 01:45 - Growing Up Entrepreneurial in Chicago 03:30 - From Investment Banking to Warrior Group 04:48 - Getting the Wrigley Field Contract in 3 Days 07:37 - From Zero to 35 Clients: How Warrior Group Scaled 10:36 - Why Founders Wait Too Long to Start 13:28 - The Scrappy Win That Felt Better Than $50K Contracts 16:22 - Fashion and Apparel: The New ICP 19:23 - What a Real Fractional CFO Actually Does 22:01 - Building the Roadmap from the Founder's Why 25:00 - Finding $1M in Obsolete Inventory from the Numbers 27:04 - Scrappy vs. Sophisticated Lightning Round 33:24 - Deep Work at 3am and Pushing the Business Forward 35:34 - Where to Find Donny and Warrior Group Guest Links: Website: https://warriorgp.com Instagram: https://www.instagram.com/donnymashiach Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Pineapple Analyst: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

From candy dealer to fractional CFO to AI SaaS founder - Joe Siegel, founder of Greenlight Financial Group, has been hustling since he was slinging pixie sticks and sodas out of his middle school locker. In this episode, Joe takes us through one of the wildest origin stories we've had on the show: dropping out of high school at 15, getting his GED, bartending through his 20s while waiting on financial aid, and eventually earning his way into UMD's top-ranked business school with a near-perfect GPA. He built a fractional CFO practice from scratch after 12 clients followed him out the door when he left his last firm - and then, just days before recording this episode, he locked himself in a room for four days and built Numvex: a full AI-powered financial dashboard SaaS for small businesses, using nothing but Claude Code, GitHub, and a $7/month server. The product is already converting strangers into paying customers on sight. This one is pure Scrappy energy from start to finish. Chapters: 00:02 - Welcome and introducing Joe Siegel 00:46 - Dumbest person in the room: Joe's operating philosophy 01:08 - Growing up in Bowie, MD with two entrepreneurial parents 02:34 - Lemonade stands, yard sales, and baseball card upsells 03:24 - The middle school candy operation (and the teacher who got paid in hush-money pixie sticks) 06:28 - First job at 13: auto mechanic shop, food truck payments, and "the room" 09:10 - Dropping out at 15, getting a GED, and why community college at 16 was a culture shock 12:08 - Panera, personal training with dad, and standing up in BNI rooms at 19 16:15 - The lawn care business: 12 yards, one push mower, and the economics that killed it 19:09 - The plan to wait until 24 for financial aid, near-4.0 at community college, and UMD Smith School 22:13 - Choosing accounting, the MMA coach's advice, and the Clever Profits run (6 to 50 employees, 15 to 250 clients) 24:15 - Leaving Clever, 12 clients calling in a week, and starting Greenlight Financial 27:04 - The iOS update that crushed online businesses and the client load rollercoaster 29:20 - Losing a long-term client and deciding to solve the value problem permanently 30:15 - Building Numvex in 4 days: AI-powered financial dashboards, fraud detection, and Claude Code 35:03 - The stranger who saw the Loom video and said "where can I pay you" 38:04 - Naming the product, talking to accounting firm partners, and what's next for Numvex 43:34 - Lightning round: three monitors, $1500 camera, and lights from a yard sale (full circle) Connect with Joe Siegel: Greenlight Financial Group: https://www.greenlighttoday.com LinkedIn: https://www.linkedin.com/in/jpsiegel/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Pineapple Analyst: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Scott Peterson walked onto the Oregon State basketball team by leaving messages on the coach's home phone until someone called back. He started his sales career bribing his way into meetings with Dunkin' Donuts. He launched his consulting firm in 2014 with a non-compete, no local network, and a city he barely knew. And somewhere in all of that, he built one of the most practical, data-driven sales frameworks for founder-led businesses you'll hear about. Scott is the founder of Carver Peterson Consulting and author of "Beyond the Founder Rainmaker." This one's got hustle, hoops, and hard-won sales truth from someone who has lived every chapter of it. Chapters: 00:03 - Welcome and intro - Scott rates himself as scrappy 00:58 - Growing up in Corvallis, Oregon - a dad who built custom homes and client relationships at the dinner table 03:49 - College, Oregon State, and the walk-on story - cold calling the coach until the callback came 07:14 - Moving to Boston cold and landing a career at Aerotech 10:10 - What Carver Peterson does and who Scott helps - the Founder Rainmaker problem explained 14:06 - Getting the first client and building the network from scratch in Chicago 18:17 - ICP evolution - how "anyone who needs sales help" gets you nowhere 20:52 - Scrappy marketing moves - donuts, dollar drafts, and freezing shorts in Boston 26:45 - Proving value to clients - data-first, scorecards, and the Revenue Compass Assessment 30:36 - Breaking out of the founder stall - two types of Founder Rainmakers and how to serve each 34:52 - The 80/20 client revenue distribution - the jaw-dropper data cut that changes strategy 37:27 - Lightning round - sports cards, steak dinners, inbox zero, and getting sassy with AI 47:09 - "Beyond the Founder Rainmaker" and what Scott is looking for next Connect with Scott: https://www.carverpeterson.com/ https://scott-ynirvf8i.scoreapp.com/ https://www.linkedin.com/company/carver-peterson-consulting-llc https://www.linkedin.com/in/carverpeterson/ 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

Susan Linder is not your typical consultant. A cultural anthropologist from the Bronx who hitchhiked through Central American war zones, trained as an AIDS epidemiologist, and stumbled into PR on a blind date, she has spent 30 years proving that the right story - told the right way - changes everything. Today she is the Founder and CEO of Innovation Storytellers and recognized as the world's leading expert on innovation storytelling. Jack and Susan trace her path from answering her dad's tool-sales phone at eight years old to working in Thai brothels in the 1990s and eventually helping Fortune 100 companies like GE, AT&T, and Citi win funding, drive acquisitions, and get their breakthrough ideas across the finish line. Along the way: why fear is a terrible long-term motivator, what it actually means to be the hero of your own story, and why innovation teams keep getting their credit stolen. Chapters: 00:00 - Introduction and the koala fingerprint fun fact 00:48 - Scrappy roots: immigrant parents, a station wagon full of tools, and the family business 05:00 - Sitting with the adults: growing up curious and always interviewing 08:00 - Phones, orders, and selling at eight years old 09:00 - Flea markets, freelance gigs, and financing college yourself 13:00 - Discovering cultural anthropology by accidentally inventing it 16:00 - Junior year abroad and hitchhiking through Central American war zones 22:00 - Thailand, HIV, and the storytelling insight that changed everything 29:00 - From the CDC to a blind date with a Forbes editor to the PR world 34:00 - Building Innovation Storytellers: the scrappy evolution from Lotus to today 37:00 - Helping innovation teams pitch the Joint Chiefs, the CFO, and everyone in between 39:00 - Lightning round: ChatGPT jokes, inbox zeros, and the font formatting confession Connect with Susan: https://www.innovationstorytellers.com https://www.linkedin.com/in/susanjlindner/ https://www.instagram.com/innovationstorytellers/ https://www.youtube.com/channel/UCId9xpyIaSwD25Z9ZsiZ3-g https://www.facebook.com/InnovationStorytellers 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

Jay Rooney is the founder of Spawn Point Marketing, a fractional CMO practice for indie and AA game studios, and the publisher of Game & Word - an award-winning Substack examining video games through interdisciplinary academic lenses. In this episode, Jay breaks down why most indie studios are invisible at launch (hint: they started marketing too late), walks through his 6-component Functional Marketing Framework, and shares the scrappy story of how he grew a mobile game from zero to hundreds of thousands of users without a single dollar in ad spend. Plus: the high school vending machine protest campaign that started it all. Chapters: 00:00 - Intro and fun fact: the AI personalities of Pac-Man ghosts 01:00 - Scrappy or sophisticated? Jay makes his case 01:40 - Growing up between New Orleans, Mexico City, and Miami 03:43 - Life with a foot in two worlds - and the entrepreneurial spark it lit 04:46 - The high school vending machine protest campaign 08:14 - Grades, curiosity, and learning how to think vs. what to think 10:05 - Game & Word: examining games through interdisciplinary academic lenses 14:49 - The $200B gaming industry and why discoverability is the real crisis 15:34 - The 6-component Functional Marketing Framework for indie studios 22:33 - How to get content creators to notice your game (the scrappy way) 27:34 - Wishlist momentum, revenue projections, and getting data-driven 29:25 - Favorite games growing up: Final Fantasy VII, Zelda, and Earthbound 31:37 - The founding of Spawn Point Marketing - sink or swim 36:48 - Getting first clients through inbound only (no cold outreach) 38:36 - Lightning round: desk setup, inbox chaos, and 63,403 unread emails 42:56 - What makes Jay feel sophisticated: buying the house and signing the office lease 43:43 - Three takeaways: start early, stay consistent, own your marketing 48:38 - Where to find Jay and the June 9 webinar Spawn Point Marketing: https://spawnpointmarketing.com Launch Readiness Scorecard: https://scorecard.spawnpointmarketing.com SPM Substack: https://spawnpointmarketing.substack.com Game & Word Substack: https://gameandword.substack.com Jay's Webinar (June 9): https://www.eventbrite.co.uk/e/building-a-marketing-engine-for-your-game-without-a-cmo-tickets-1988318245396?aff=jay Jay on LinkedIn: https://www.linkedin.com/in/jayrooneysf/ https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Eric Tjoeng grew up in Indonesia in a family of seven entrepreneurs, started his first business venture at age 12 promoting a comedy show, and eventually moved to Australia to build a career starting at Deloitte. After 20+ years in senior executive roles at multinationals - including GM of a $1.4B automotive group - he founded Business Growth and Exit Specialists (BGES) in Sydney, where he now helps small and medium businesses grow strategically and exit successfully. He's 100% sophisticated, and the data agrees. Chapters: 00:00 - Intro and Australia Fun Fact: The Dingo Fence 01:11 - Scrappy or Sophisticated? Eric's Answer 02:45 - Growing Up in Indonesia with 7 Entrepreneurs 05:28 - Age 12 Comedy Show Promoter and First Investment 07:14 - Deloitte, Multinationals, and the SME Shift 10:34 - Why SME Owners Work Hard But Don't Get Returns 13:27 - The Dashboard Formula and Data-Driven Strategy 17:35 - Founding BGES and Getting That First Client 25:40 - The Australia Exit Crisis: 200K Exits, 45K Walk Away With Nothing 31:10 - The BGES Exit Formula and Business Valuation 38:44 - Speed vs. Strategy - Eric's Answer 40:27 - Lightning Round: Inbox, Celebrations, and Vetting Clients 43:39 - Final Verdict: 100% Sophisticated Guest Links: https://www.linkedin.com/in/etjoeng/ https://bges.co 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

What does it really take to build a business that creates higher returns AND more joy? Tina Dao, founder of Liberated Leaders, has lived the answer - from baking cupcakes for her dad's hunting camps and negotiating car loans with her grandpa at 17, to leading operations at Amazon, Fitbit, and Walmart before launching her own fractional COO firm. In this episode, Tina and Jack dig into conscious capitalism, the "silver tsunami" of business transitions, why the trades are safer than college right now, and how to know when your company needs to move between scrappy and sophisticated. Chapters: 00:00 - Intro + fun fact: butterflies taste with their feet 00:54 - Scrappy vs. sophisticated: Tina's take on the tension between the two 02:00 - Growing up in Western Colorado with sheep ranchers and serial entrepreneurs 09:04 - First hustles: baking for hunting camps, babysitting, and cleaning houses at 12 13:42 - Negotiating a car loan from grandpa at 17 - with a term sheet 15:32 - A 2.0 GPA, 98s on every test, and why the trades beat college right now 19:06 - US Navy electronics technician to corporate operations 25:32 - Starting Liberated Leaders and the case for conscious capitalism 29:25 - Landing the first client, the family bet, and the real cost of going out on your own 35:15 - Lightning round: scrappy studio, inbox limits, and corporate pet peeves 43:39 - The Liberated Leaders pitch: 5-10x returns, more delight, and the silver tsunami Tina Dao - Liberated Leaders https://www.liberatedleaders.com, https://www.linkedin.com/in/tinaldao/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

What happens when a corporate employee discovers Amazon, teaches himself e-commerce, becomes a CMO, and then realizes the whole agency model is broken? You get Tanner Rankin - founder of Source Approach, Referazon, and the Brand Source OS - and a seriously compelling story about turning scrappy roots into a sophisticated operating system for brands. Tanner breaks down how he built the Brand Operating System from a pile of spreadsheets, why most brands fail their agency partners (not the other way around), and what it actually looks like to make marketing predictable and repeatable. If you're tired of random acts of marketing, this one's for you. Chapters: 0:00 - Intro and fun fact 0:52 - Scrappy roots: corporate robot turned Amazon seller 4:07 - The CMO role and the cold hard look in the mirror 12:34 - Building Source Approach and the first Brand OS 19:35 - Entrepreneur ADD, Referazon, and solving the right problems 26:09 - Fake it till you make it and the MVP trap 30:44 - Who Source Approach serves today 33:06 - The woodsman in a suit: office tour and lightning round 45:42 - KPIs, client success, and what makes marketing repeatable Connect with Tanner: Website: https://www.sourceapproach.com Personal site: https://www.tannerrankin.com LinkedIn: https://www.linkedin.com/in/tannerrankin/ Referazon: https://www.referazon.com Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Phil Risher didn't have entrepreneurs in the family - he had a single mom, a pest control dad, a rap career in high school, and eventually a school bus he lived in while figuring out his next move. Somehow it all led to Phlash Consulting, a 22-person marketing and data firm that grew home service businesses an average of 27% last year. In this one, Jack and Phil trace the full origin story - from selling autographed CDs out of a backpack to managing a $300K/month Enterprise branch at 25, to quitting corporate on his honeymoon and building something entirely his own. Topics covered: 0:00 - Intro and fun fact - the most expensive pineapple in history 0:52 - Scrappy vs. sophisticated and Phil's honest opening take 1:16 - Growing up outside DC, immigrant hustle, and the high school rap career that launched it all 7:36 - Ruby Tuesday's, commission brain, and the first real entrepreneurial unlock 8:22 - Geneva College, three majors, studying abroad in Rome and China, and $30K in student loans 10:12 - Paying off debt in 12 months, buying a condo at 25, and building zero-debt infrastructure 12:04 - Enterprise Rent-a-Car, the BMI report, and running a $300K/month branch on data alone 17:47 - The school bus trip, the duck cleaning company, and when all the worlds collided 22:08 - The three levers every home service business needs: marketing, data, and automations 25:15 - The growth thresholds - systems to 3M, data to 5M, people to 10M 27:15 - How Tom fired Phil to set him up, the name Phlash, and the private equity framework that built the whole business 35:28 - Profit First, abundance mindset, and leading a team with a vision big enough for everyone 38:13 - Minimalist office, 100% on or off, and making the Inc. 5000 Best Workplaces list Connect with Phil Risher: https://phlashconsulting.com https://www.linkedin.com/in/philrisher/ https://www.instagram.com/philrisher/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Elizabeth Rose is President and Lead Coach at Garth Rose Consulting Group, where she brings 27 years of mediation experience and a decade of executive coaching to leaders and teams. But before the polished practice, there was a VW camper rolling through Europe, a Starbucks apron, and a borrowed conference room. Elizabeth's path from Long Island to law school to barista-turned-mediator is one of the scrappiest origin stories we've had on the show - and her work is as rigorous as her roots are "ready, fire, aim." In this episode, Jack and Elizabeth dig into somatic experiencing (yes, your body is keeping score), why emotional intelligence is the real ROI lever for your sales team, and why great leadership now means admitting when your two-year-old kept you up all night. Chapters: 00:00 - Intro + Fun Fact: Mangoes Rule the World 01:22 - Long Island Roots and an Accidentally Wild Upbringing 07:01 - Senior Year of High School in Hong Kong 10:47 - From Retail Buyer to Stay-at-Home Mom to Law School With Three Kids 13:14 - Three Months as a Lawyer, Then the Pivot to Mediation 15:04 - Getting Her First Client as a Starbucks Barista 16:43 - Building a Practice Out of a Borrowed Conference Room 22:32 - Where Elizabeth's Emotional Intelligence Approach Comes From 24:49 - What Is Somatic Experiencing? 30:21 - The Two-Minute Body Scan: A Practical First Step 34:04 - Somatics in the Boardroom: Executive Coaching in Practice 39:15 - Measuring the ROI of Emotional Intelligence Work 42:10 - Lightning Round: Scrappy vs. Sophisticated   Connect with Elizabeth: https://www.linkedin.com/in/elizabethroseesq https://garthrose.com   Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Nick Reich is the co-founder of Abundant Empowerment and the founder of CoLab - a peer-powered community for consultants and leaders. A first-gen college kid from Evansville, Indiana, Nick went from school social worker to building the fastest state championship basketball program in Indiana high school history, and then spent the next 15 years turning those lessons into a people first framework for building high performing teams. His book, Every Player is Bigger Than the Program, drops September 8th. This one covers a lot of ground. Topics covered in this episode: How Nick's blue collar upbringing as a first-gen kid in Evansville shaped his people first philosophy His first job in 1995: quality-testing an early online dating app - officially scrappy The hat, haircut, or tattoo framework for cutting analysis paralysis and making faster decisions How Nick built Indiana's fastest state championship basketball program starting from a school with no gym Why people first leadership is NOT soft - it means high expectations and high accountability How Abundant Empowerment came together when Nick merged River and Green with Andrea's decade-old vision What give first actually means and why Nick deliberately disconnects generosity from expecting anything back The book Every Player is Bigger Than the Program - what it's about, when it drops, and where to get it 0:00 - Welcome and fun fact: palm trees are actually grass 1:07 - Blue collar roots: first-gen college kid from Evansville 3:47 - First job: quality-testing a 1995 online dating app 8:31 - Hat, haircut, or tattoo - the decision framework that changes everything 11:25 - Quitting the team and what it taught about second chances 14:56 - Coaching teens vs. coaching executives - the correlation 18:54 - Indiana's fastest state championship, built from scratch 22:38 - Defining success when there's no scoreboard 26:38 - From River and Green to Abundant Empowerment 30:25 - Faking it till you make it - and still doing it 33:46 - Rapid fire: texts, audiobooks, and the networking escape plan 39:42 - Give first: disconnecting generosity from the ask 43:31 - Every Player is Bigger Than the Program Connect with Nick: https://www.abundantempowerment.com, https://www.peoplefirstplaybook.com, https://www.linkedin.com/in/nick-reich05/ Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Ryen Salo is the Client Experience Manager at CherryBecker, a 10-year CX veteran, Association for Accounting Marketing (AAM) member and speaker, Finnish sauna enthusiast, and self-described "one and fun" mom living just outside Portland, Oregon. In this episode, Ryen takes us from selling candy and running a seven-dollar blackberry stand in Grants Pass, to driving a 50-mph Mug Root Beer VW Bug for Pepsi Cola, to dropping in and out of college for years before finally finishing her degree through an adult completion program - all while working full-time and being newly married. She breaks down what client experience actually requires (spoiler: it's curiosity), why you have to stop making it about yourself, and why she and Jack are both speaking at the AAM Summit in Palm Springs this May. In this episode: 00:00 - Intro and the bell pepper bump fun fact you will never forget 02:42 - Growing up scrappy in Grants Pass, Oregon and a mom who quietly ran the school 08:15 - Learning differently, the teachers who really saw her, and why grades don't tell the whole story 11:21 - Raising her son in a Title I school and celebrating neurodiversity in 2025 16:06 - The winding college road - Eugene to California to Portland, food stamps, and finally finishing 18:50 - Driving the Mug Bug - Pepsi Cola's 50-mph soda car and sampling at events 26:46 - Working at The Climb (while not outdoorsy at all) and winning the guac off two years running 28:50 - What client experience actually requires - curiosity, listening, and getting out of your own way 33:28 - The CX partnership philosophy - becoming an extension of the client's team 35:45 - The Jefferson Memorial and the five whys - how Jack and Ryen both think about root causes 37:20 - AAM (Association for Accounting Marketing) and what to expect at the Palm Springs summit 42:28 - Lightning round - airports, inbox philosophy, JBL earbuds, and the final scrappy vs. sophisticated verdict Connect with Ryen Salo: LinkedIn: https://www.linkedin.com/in/ryen-salo/ AAM (Association for Accounting Marketing): https://accountingmarketing.org/ Listen on: Spotify: https://open.spotify.com/show/3zSMlS41U0FfttadYBYbri?si=f856281edcae4c53 Apple Podcasts: https://podcasts.apple.com/us/podcast/scrappy-but-successful-consultants-personalities-when/id1878384628 Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

What do a $180 driveway shoveling gig, a fake million dollar bill at the Houston airport, and raising over $2 billion in capital all have in common? Brad Blazar. This week on Scrappy But Successful, Jack sits down with the founder of Capital Connections - a knighted speaker, bestselling author, podcast host, and genuinely one of the most interesting people to ever sit across from Jack. Brad breaks down his trademarked philosophy "Beliefology," the psychology behind raising capital without desperation, and some legendary scrappy moves that prove you don't always need a marketing budget - just a Starbucks tab and the right mindset. In this episode: (00:03) Intro - Snails, scrappiness, and meet Brad Blazar (01:55) Moving city to city as a kid and becoming a social chameleon (06:51) Paper routes, snow shoveling, and the $180 driveway hustle (10:17) Investing, philanthropy, and why distributions beat W-2 income (16:27) Beliefology - the trademarked philosophy and the story of Jack going from 480 lbs to Men's Fitness cover (20:19) Fear = False Evidence that Appears Real - and why comfort is your worst enemy (24:02) How to raise capital without sounding desperate - slow down, discovery first, pitch last (33:05) The $3 Starbucks strategy that unlocked Dallas's wealthiest doors (40:24) Lightning round - first class, Centurion Lounge, and metal business cards (43:43) The million dollar bill, AirTag luggage hacks, and surviving CrowdStrike Day in flip flops Learn more about Brad: https://www.bradblazar.com Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Steve Hopper spent years climbing the corporate ladder before a toxic work environment - and a nudge from his wife - pushed him to bet on himself. In 2004, he founded Inviscid Consulting, a supply chain and warehouse operations firm that has since worked with clients ranging from $80B corporations to PE-backed startups. What started as turning over rocks with a small network has grown into 21 years of steady upward trajectory, a thriving expert witness practice across 65-plus legal cases, and a side life as the drummer for the Falls Brothers Band. Steve breaks down exactly how to think about consulting ROI (a client once passed on a 200% return because of the wrong budget bucket), why the mid-market is where the real opportunity lives, and the difference between being accountable and being set up to fail. How a Ben Franklin pros/cons list convinced Steve to turn down a corporate offer and start his own firm in 2004 The "authority and accountability relationship" framework Steve teaches every client - and lived through himself Breaking down the market pyramid: why Steve ignores the top and bottom and focuses everything on the $200M-$2B middle Why Inviscid has been on 65-plus expert witness cases - and what it actually means to "advocate for the truth" on the stand The $31M jury verdict, 1,000+ documents, and why this work is nothing like the TV version How to calculate real consulting ROI - and the auto parts company that wouldn't act on a 6-month payback Lightning round: timewithsteve.com, 4-5 phone numbers (one for band bookings), 100+ unread emails, and Googling someone mid-meeting Chapters: 0:00 - Intro and Fun Fact: Ducks Have Regional Accents 1:44 - Growing Up in Charlotte and Atlanta 3:40 - The Entrepreneurial Bug and Cub Scout Sales 5:23 - Turning Down the Corporate Offer and Taking the Leap 7:57 - The Early Days of Inviscid: Turning Over Rocks 11:44 - Stability vs. Control: The Real Trade-off of Entrepreneurship 14:30 - Authority, Accountability, and Driving Your Own Destiny 19:13 - KPIs in Warehousing: From DC-Level to Individual Workers 21:08 - The Market Pyramid: Why Steve Focuses on the Mid-Market 27:03 - Consulting ROI: The Auto Parts Company That Passed on 200% 32:59 - The Expert Witness Practice: 65+ Cases, $31M Verdicts, Advocating for Truth 40:14 - Lightning Round: timewithsteve.com, Band Bookings, and Googling Mid-Meeting Guest: Steve Hopper - Founder, Inviscid Consulting Website: https://inviscidconsulting.com Host: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

La Tonya Roberts has always had a plan - and the grit to execute it. From running a lemonade stand outside a military base in Alaska at age 7 to pitching her parents with formal PowerPoint presentations for Christmas gifts, La Tonya's scrappiness has always been strategic. Today she's the founder of Harmony Consulting Group, a fractional COO, AI strategist, and host of the podcast Systems That Set You Free - and in this episode she walks us through every pivot that got her there. What we cover: Growing up as an Army Brat across Alaska, Germany, Maryland, and beyond Running childhood businesses with military-grade market research (seriously) From cosmetologist to Booz Allen to Deloitte - and knowing when to leave Going all-in on entrepreneurship in 2020 and hitting $1M in a year What fractional COO work actually looks like and who it's for Helping visionary founders slow down, build systems, and scale Why AI isn't the enemy - it's just a tool that still needs a human "Chatasia" and why naming your AI makes all the difference The lightning round: calendar links, color-coded inboxes, and docking stations Chapters: 0:00 - Welcome & Fun Fact: Crows Hold Grudges 0:53 - Scrappy or Sophisticated? La Tonya Answers 1:00 - Army Brat Upbringing & Entrepreneur Roots 2:31 - Lemonade Stands, Chocolate Bars & Military Market Research 4:35 - PowerPoint Pitches to Parents (and Winning) 7:10 - Raising Negotiators: La Tonya's Kids Turn the Tables 10:04 - Single Mom, Grad School & Building Systems at Home 13:30 - Academic Scholarships, Side Hustles & Cosmetology 19:02 - How La Tonya Found Consulting (Thanks, Dad) 22:07 - Leaving Deloitte, Moving to Atlanta & Going Full-Time in 2021 29:03 - Fractional COO Work: Slowing Down Visionaries 34:46 - Strategy, AI Integration & Operational Excellence 39:14 - Lightning Round: Calendly, ClickUp & Chatasia 47:47 - Where to Find La Tonya & Final Thoughts Connect with La Tonya Roberts: Podcast: Systems That Set You Free (Spotify, Apple Podcasts, YouTube) Discover more about La Tonya's fractional COO services and other offerings at https://www.harmonyconsultinggroup.org Follow her on social media for daily inspiration and actionable tips: LinkedIn: https://www.LinkedIn.com/in/La-Tonya-roberts Facebook: https://www.facebook.com/thelatonyaroberts Instagram: https://www.instagram.com/thelatonyaroberts TikTok: https://www.tiktok.com/@thelatonyaroberts YouTube: https://www.youtube.com/@TheLaTonyaRoberts Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

What happens when a near-death experience on a Manhattan construction site becomes the catalyst for a career in sales — and eventually a global consulting company? Stephen Steers, founder of Steers Consulting Group, comedian, keynote speaker, and author of Superpower Storytelling, joins Jack to trace the scrappy origins of an unlikely entrepreneur. From flipping yard sale finds on Craigslist to advising Google, Nike, and over a thousand companies across 40+ countries, Stephen's story is equal parts hustle and hard-won wisdom. In this episode: Growing up in NYC with Jamaican roots — and why "a man can't leave without keys and money" was Stephen's motto at age six Uncle Willie, $20 Saturdays, and the first real lesson in work ethic Selling popsicles from Costco in high school (300 pack, a quarter a piece — do the math) Construction work, a near-death moment on 6th Ave, and the walk that changed everything Launching a consulting company in 2019 and watching COVID nearly take it all away The Mexico beach reset — and what slowing down actually taught him Context Selling: why what the customer says is truth, and what you say, you must defend Ernest Shackleton, Antarctica, and why this is the book Stephen just finished this week The lightning round: inbox zero, no TSA PreCheck, work clothes at home, and two phone numbers Chapters: 00:03 – Welcome & Fun Fact: Squirrels and Entrepreneur ADD 01:05 – Scrappy or Sophisticated? Stephen's Verdict 02:14 – Growing Up in NYC with Jamaican Roots 04:20 – Uncle Willie, Two Hands & the First $20 05:37 – Selling Popsicles & Flipping Craigslist Finds 09:28 – Construction Work and Almost Dying 11:49 – The Walk That Changed Everything 16:33 – Ernest Shackleton, Antarctica & the Scrappy Mindset 21:17 – Working with Google, Nike & Founders Who Can't Sell 23:03 – Context Selling Explained 28:50 – Starting the Company & Getting Hit by COVID 33:02 – The Mexico Beach Reset 36:26 – High School Stephen & Boarding School 41:43 – Coaching Sales Teams & Measuring Success 44:21 – Lightning Round 52:24 – Where to Find Stephen Steers Connect with Stephen Steers: https://www.stephensteers.com/podcast https://www.linkedin.com/in/stephen-steers/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/