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

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

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

De : Pineapple Jack
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 This isn't your typical business podcast. It's a business-and-comedy crossover for consultants, fractional CFOs, advisors, and service-based entrepreneurs who are building real consulting businesses. We talk entrepreneurship, make jokes, and actually enjoy the conversation. We start with where our guest came from, dig into the early (often messy) days of their career, and unpack how their personality shows up in their business today — from client relationships and boundaries to pricing decisions and growth strategy. We'll determine whether they're scrappy or sophisticated through a series of fun stories and rapid-fire questions that reveal how they really operate behind the scenes. Along the way, we pull random questions, laugh at corporate nonsense, solve an actual data or analytics problem, and get to know their business in a way they've never described it before. You'll hear real conversations about consulting challenges, scope creep, decision-making, and how data-driven thinking supports smarter business growth. No fluff. No canned answers. Just fun, genuine conversation, with a dash of entrepreneurial lessons you can actually apply to your own consulting business. Because people listen more when you're having fun. And people do business with people they actually like. ABOUT JACK TOMPKINS & PINEAPPLE CONSULTING FIRM Jack (aka "Pineapple Jack") is the host of Scrappy but Successful, a professional speaker, and the founder of Pineapple Consulting Firm. As one of the early Fractional Analysts, Jack brings his clients' data to life with storytelling visuals and impactful insights while adding a sense of humor that makes analytics actually fun. You'll see that fun come through in spades on Scrappy but Successful as he aims to bring out the guest's personality through laughter and stories, while giving listeners some pretty useful takeaways along the way. Head to https://www.pineapplecf.com/ to turn your data into visual, understandable, decision-driving insights.2026 Direction Economie Management Management et direction
Épisodes
  • 9. The Scrappy Strategist: How La Tonya Roberts Went from Cosmetologist to COO with La Tonya Roberts

    9. The Scrappy Strategist: How La Tonya Roberts Went from Cosmetologist to COO with La Tonya Roberts
    Apr 6 2026
    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 beyondRunning childhood businesses with military-grade market research (seriously)From cosmetologist to Booz Allen to Deloitte - and knowing when to leaveGoing all-in on entrepreneurship in 2020 and hitting $1M in a yearWhat fractional COO work actually looks like and who it's forHelping visionary founders slow down, build systems, and scaleWhy AI isn't the enemy - it's just a tool that still needs a human"Chatasia" and why naming your AI makes all the differenceThe lightning round: calendar links, color-coded inboxes, and docking stations Chapters: 0:00 - Welcome & Fun Fact: Crows Hold Grudges0:53 - Scrappy or Sophisticated? La Tonya Answers1:00 - Army Brat Upbringing & Entrepreneur Roots2:31 - Lemonade Stands, Chocolate Bars & Military Market Research4:35 - PowerPoint Pitches to Parents (and Winning)7:10 - Raising Negotiators: La Tonya's Kids Turn the Tables10:04 - Single Mom, Grad School & Building Systems at Home13:30 - Academic Scholarships, Side Hustles & Cosmetology19:02 - How La Tonya Found Consulting (Thanks, Dad)22:07 - Leaving Deloitte, Moving to Atlanta & Going Full-Time in 202129:03 - Fractional COO Work: Slowing Down Visionaries34:46 - Strategy, AI Integration & Operational Excellence39:14 - Lightning Round: Calendly, ClickUp & Chatasia47:47 - 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.orgFollow her on social media for daily inspiration and actionable tips: LinkedIn: https://www.LinkedIn.com/in/La-Tonya-robertsFacebook: https://www.facebook.com/thelatonyarobertsInstagram: https://www.instagram.com/thelatonyarobertsTikTok: https://www.tiktok.com/@thelatonyarobertsYouTube: https://www.youtube.com/@TheLaTonyaRoberts Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/Pineapple Consulting Firm: https://www.pineapplecf.comSpeaking: https://www.pineapplejacktompkins.com/YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng
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    49 min
  • Ep 8. The Context is the Close - Sales Lessons from a Scrappy yet Sophisticated Stephen Steers

    Ep 8. The Context is the Close - Sales Lessons from a Scrappy yet Sophisticated Stephen Steers
    Mar 30 2026
    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 sixUncle Willie, $20 Saturdays, and the first real lesson in work ethicSelling 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 everythingLaunching a consulting company in 2019 and watching COVID nearly take it all awayThe Mexico beach reset — and what slowing down actually taught himContext Selling: why what the customer says is truth, and what you say, you must defendErnest Shackleton, Antarctica, and why this is the book Stephen just finished this weekThe lightning round: inbox zero, no TSA PreCheck, work clothes at home, and two phone numbers Chapters: 00:03 – Welcome & Fun Fact: Squirrels and Entrepreneur ADD01:05 – Scrappy or Sophisticated? Stephen's Verdict02:14 – Growing Up in NYC with Jamaican Roots04:20 – Uncle Willie, Two Hands & the First $2005:37 – Selling Popsicles & Flipping Craigslist Finds09:28 – Construction Work and Almost Dying11:49 – The Walk That Changed Everything16:33 – Ernest Shackleton, Antarctica & the Scrappy Mindset21:17 – Working with Google, Nike & Founders Who Can't Sell23:03 – Context Selling Explained28:50 – Starting the Company & Getting Hit by COVID33:02 – The Mexico Beach Reset36:26 – High School Stephen & Boarding School41:43 – Coaching Sales Teams & Measuring Success44:21 – Lightning Round52:24 – 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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    53 min
  • Ep 7. Why Finance Pros Can't Communicate (And How to Fix It) with John Sanchez

    Ep 7. Why Finance Pros Can't Communicate (And How to Fix It) with John Sanchez
    Mar 26 2026
    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 friendsThe 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 wouldFrom Big Six accounting to M&A at Blockbuster — including a private jet trip to evaluate Aaron Spelling's entertainment empire at age 23The accidental entrepreneur moment at a Chamber of Commerce meeting that changed everythingWhy the communication bar in accounting and finance is surprisingly low — and the simple frameworks that can get you most of the way thereChris 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 Fact02:46 – Growing Up Military: 12 Moves & a Roach Coach05:10 – ROTC, Eclectic Friends & the Hallway Deal10:44 – Tony Robbins Tapes & the Psychology Bug15:53 – Six Majors, FSU & Landing on Accounting20:33 – The Vouching Moment That Changed Everything23:13 – M&A at Blockbuster & a Private Jet to 9021030:06 – The Accidental Entrepreneur34:44 – Communication Training for Finance Pros38:09 – Rejection Words, Chris Voss & Labeling Emotions46:26 – Lightning Round & Networking Tips50:51 – 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.comSpeaking: https://www.pineapplejacktompkins.com/
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    52 min
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