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AI-generated executive summaries from your dashboard in seconds — walk into any meeting fully prepared 👇 🔗 Try Fabi (partner discount): https://www.fabi.ai/?via=jack 🍍 Our AI Dashboard services: https://www.pineapplecf.com/ai-dashboards

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/

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Finance pros are notorious for hiding behind spreadsheets — but what happens when one of their own decides to call that out? John Sanchez went from military kid moving 12 times before graduation, to doing M&A deals at Blockbuster, to accidentally stumbling into entrepreneurship, to becoming one of the go-to communication trainers in accounting and finance. Turns out the bar is low — and he's made a career out of raising it. **In this episode:** - How growing up as a military brat (12 moves, one tiny kid) forged a scrappy, adaptable mindset — and an eclectic group of friends - The ROTC hallway protection racket that Jack called out as a "higher-level bartering system" - Why John bought Tony Robbins cassette tapes in high school and why he was simultaneously afraid they *wouldn't* work — and that they *would* - From Big Six accounting to M&A at Blockbuster — including a private jet trip to evaluate Aaron Spelling's entertainment empire at age 23 - The accidental entrepreneur moment at a Chamber of Commerce meeting that changed everything - Why the communication bar in accounting and finance is surprisingly low — and the simple frameworks that can get you most of the way there - Chris Voss, rejection words, labeling emotions, and why "is now a bad time?" is better than "do you have a minute?" - Lightning round: no TSA Pre-Check, skeptical of airport breakfast, and strong opinions on pre-flight cocktails **Chapters:** - 00:00 – Intro & Fun Fact - 02:46 – Growing Up Military: 12 Moves & a Roach Coach - 05:10 – ROTC, Eclectic Friends & the Hallway Deal - 10:44 – Tony Robbins Tapes & the Psychology Bug - 15:53 – Six Majors, FSU & Landing on Accounting - 20:33 – The Vouching Moment That Changed Everything - 23:13 – M&A at Blockbuster & a Private Jet to 90210 - 30:06 – The Accidental Entrepreneur - 34:44 – Communication Training for Finance Pros - 38:09 – Rejection Words, Chris Voss & Labeling Emotions - 46:26 – Lightning Round & Networking Tips - 50:51 – Where to Find John **Connect with John Sanchez:** - LinkedIn: https://www.linkedin.com/in/fpajohn/ - FP&A LinkedIn Group: https://www.linkedin.com/groups/2223974/ **Connect with Jack Tompkins:** - LinkedIn: https://www.linkedin.com/in/jack-tompkins/ - Company: https://www.pineapplecf.com - Speaking: https://www.pineapplejacktompkins.com/

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Scrappy Beginnings, Sophisticated Strategy — ft. Neel Singh of Tropoly What do hand-drawn comic book ads, a secret stack of freelance business cards at a bank job, and a drunk chef have in common? They're all chapters in Neel Singh's story — and they're exactly why he's one of the most interesting people in B2B marketing today. Neel is the Managing Partner and Founder of Tropoly, a former CMO, and a multi-time founder who's built his career at the intersection of creative instinct and strategic rigor. Jack and Neel dig into what it actually means to deliver sophisticated strategy to scrappy clients — and why Neel tells every new client their beautiful plan is "complete bullshit" before the real work begins. In this episode: - From graphic design side hustles to running a tapas bar at 28 — Neel's wild path to the C-suite - Why great strategy should come with a scenario planning dashboard, not just a slide deck - The "heads and hands" philosophy behind Tropoly's integrated marketing approach - How Vancouver Film School shaped Neel's storytelling instincts (and ruined movies for him) - Getting sassy with AI, birthday hangovers, and the all-subject-line email heard 'round the office Verdict: Scrappy beginnings. Sophisticated execution. A healthy and very intentional blend of both. - 00:00 Intro & Sophisticated Scrappiness - 01:58 Growing Up in Vancouver — Creatives, Entrepreneurs & Poets - 06:23 Comic Books, Video Games & Finding Creativity Early - 11:47 Bad Grades, Film School & Learning Differently - 19:10 First Business: Graphic Design & Sliding Extra Cards at the Bank - 22:14 Buying a Restaurant at 28 — The Real MBA - 28:00 From CMO to Founder: Building Tropoly - 36:00 Integrated Marketing for Complex Industries - 43:00 Why Every Strategy Plan is "Complete Bullshit" (And What to Do About It) - 47:04 Lightning Round 🔗 Connect with Neel: https://www.linkedin.com/in/neelsingh https://tropoly.io 🔗 Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineapplejacktompkins.com/ ---

Profit First is a powerful way to find hidden profit leaks that quietly drain small businesses. Diane Gardner helps business owners use the Profit First method to manage cash flow, increase profit margin, and build healthier businesses that actually keep the money they earn. Her journey into this work started in an unlikely place. Diane grew up in a tiny mining town of about 1,500 people where entrepreneurship was not exactly the family career path. Her dad worked in the mines and believed in practical skills like learning to drive a manual truck on a hillside before she could ever take the wheel. A chance connection with an accountant in her small town eventually set Diane on a path that turned into a decades long career. Today she is a tax strategist, Profit First coach, author, and host of the Profitable Home Services Podcast. She works with contractors and small business owners who want to increase profit margin, grow revenue, and turn hard work into real financial results. Along the way we talk about the early days of building a business from scratch, the lessons that shaped her approach to money, and the mindset shifts that help small business owners grow profitable companies instead of just busy ones. *What Comes Up When Consultants Talk Shop:* 🍍Growing up in a tiny mining town and how a chance connection led Diane into accounting 🍍The scrappy early years of entrepreneurship, from ramen noodles to door to door client hunting 🍍Why many hardworking business owners still struggle to turn revenue into real profit 🍍The hidden profit leaks quietly draining home service businesses 🍍Why the classic December spending spree is terrible tax planning 🍍Creative tax strategies most small business owners have never heard about 🍍How the Profit First system changes the way businesses manage cash flow 🍍Simple ways to generate more revenue from existing customers instead of chasing new ones 🍍How Diane helps blue collar business owners become wildly profitable and proud of it *Key Moments:* 00:00 Intro 02:10 Growing Up In A Tiny Idaho Mining Town And Why Scrappy Was The Only Option 12:45 The Unexpected Reason Diane Became An Accountant 23:30 Door To Door Client Hunting And The Reality Of Building A Business From Scratch 37:15 Why Growing Revenue Still Leaves Business Owners Feeling Broke 49:40 The Real Problem With Last Minute Tax Planning 64:20 How The Profit First System Changes The Way Owners Handle Cash 82:10 Why Your Best Customers Are The Ones You Already Have ABOUT Diane Gardner: Your Profit & Tax Coach A Speaker and Best-Selling Author Quilly Award recipient Host of the Profitable Home Services Podcast Learn more about Diane and connect at https://profitcoach4you.com/ ABOUT JACK TOMPKINS & PINEAPPLE CONSULTING FIRM Jack (aka "Pineapple Jack") is the host of Scrappy but Successful, a professional speaker, and the founder of Pineapple Consulting Firm. As one of the early Fractional Analysts, Jack brings his clients' data to life with storytelling visuals and impactful insights while adding a sense of humor that makes analytics actually fun. You’ll see that fun come through in spades on Scrappy but Successful as he aims to bring out the guest’s personality through laughter and stories, while giving listeners some pretty useful takeaways along the way. Head to https://www.pineapplecf.com/ to turn your data into visual, understandable, decision-driving insights.

Dataddo is our favorite Data ETL too for getting QuickBooks data into a dashboard! This is a full walkthrough on how we use Dataddo to get data flowing so it can be easily put into a dashboard. For more on Dataddo, check them out here: https://www.dataddo.com/signup?utm_source=pineapple&utm_medium=newsletter&utm_campaign=partner_newsletter For more on us: https://www.pineapplecf.com/ White-label dashboards: pineapplecf.com/white-label-dashboards **Chapters:** • 00:00 - Intro & What We're Building • 00:47 - Setting Up a Flow in Dataddo • 01:29 - Connecting & Configuring QuickBooks as a Source • 04:40 - Setting Up Google Sheets as a Destination • 06:32 - Reviewing the Data Output • 07:41 - Building a Dashboard in Looker Studio & Wrap-Up