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

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/

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/

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: linkedin.com/in/neelsingh | tropoly.io 🔗 Connect with Jack: LinkedIn | Pineapple Consulting | Speaking

What happens when someone who grew up in a tiny mining town of 1,500 people ends up becoming a trusted profit strategist for home service businesses? Diane Gardner's story is a scrappy one. She didn't grow up around entrepreneurs. 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 set Diane on a path that has now 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 blue-collar business owners who are working hard but want to see more of that effort turn into real profit. 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 owners build businesses that are not just busy, but truly profitable.   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   ABOUT Diane Gardner:  Your Profit & Tax Coach 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 comes 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.

What happens when a self-proclaimed lazy kid who once walked out of high school ends up running an award-winning IT company? That is exactly what Isaac Alexander unpacks in this conversation. Isaac is the President of Quo Vadis, Charlotte's Best IT Provider for 2025, and a former mortgage sales leader who helped scale a company from four people to more than one hundred almost overnight. From a father-in-law challenge that changed his trajectory to leading through rapid growth and rebuilding with discipline, Isaac shares the inflection points that shaped him. You will hear how he reframed a "commodity" IT business into a customer service company with standards that actually move the needle. We also touch on succession, acquisition goals, and the systems behind sustainable growth. It is a practical look at what happens when scrappy ambition meets intentional structure. What Comes Up When Consultants Talk Shop: The father-in-law conversation that forced Isaac to level up and leave the restaurant world behind What scaling from 4 people to 100 in under two years feels like on the inside Why anxiety hit hard during rapid growth and how discipline became the reset button The mindset shift from "we do IT" to "we are a customer service company that happens to do IT" The 15-minute response standard that crushed industry averages Why most MSPs lose clients without realizing it and how to make switching frictionless How EOS scorecards and forward-looking KPIs prepare you to acquire another business What it really means to dream big enough that your team's goals fit inside yours The scrappy traits Isaac still carries today and the sophisticated systems he had to build around them   ABOUT ISAAC ALEXANDER:  President of Quo Vadis Inc. 13 years in the mortgage industry https://quo.cc/ https://www.linkedin.com/company/quovadis-it   https://x.com/QuoVadisInc Charlotte's Best Award Winner Award celebration https://www.facebook.com/people/Quo-Vadis/61578842335195/#   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 comes 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.

Ever find yourself staring into the fridge after a long day, trying to figure out what you should eat, only to give up and grab whatever is easiest? That tug-of-war between eating healthy and just surviving the week is exactly what this conversation gets into. For this episode of Scrappy But Successful, I'm joined by longtime friend and registered dietitian Kasey Strouse, founder of Normally Nourished. We dig into how her scrappy path through restaurant jobs, tough college classes, and hospital nutrition work eventually led her to build a thriving non-diet nutrition practice. Along the way, Kasey shares how growing up with an entrepreneur dad and seeing firsthand how health challenges impact families shaped her passion for helping people build healthier, less stressful relationships with food. Kasey offers practical, judgment-free advice that makes eating well feel doable again. If you're trying to balance real life with healthier habits without turning food into another stressful project, this episode delivers both laughs and useful takeaways. What Comes Up When Consultants Talk Shop Growing up with an entrepreneur parent and how that shaped Kasey's own business journey Why restaurant jobs teach communication skills that show up later in business and client work How organic chemistry almost derailed her plans and what she did to push through The reality of working in clinical nutrition and realizing it was not the right long-term fit Why most diets fail and what actually helps people build sustainable habits What it really means to be a "non-diet dietitian." How to eat well when you're busy, burned out, or just don't feel like cooking The Sunday planning habit that makes weekday meals easier Why stressing over food choices can sometimes do more harm than the food itself The truth about protein trends and why fiber deserves more attention Real-life meal ideas that work when motivation is low and schedules are packed How Kasey balances running a practice while keeping life and nutrition realistic and flexible   ABOUT KASEY STROUSE:  Registered dietitian and an Iaedp Approved Certified Eating Disorder Specialist - Consultant/Supervisor Learn more about Kasey and connect at https://www.normallynourished.com/ Instagram: @normallynourished   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 comes 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.  

You can work your tail off… and still lose money in your "dream job." That's the uncomfortable realization Michele Williams had after years of doing work she loved, only to discover she wasn't actually charging for the most valuable part of it: her thinking. When I sat down with Michele, a two-time founder and the force behind Scarlet Thread Consulting and Matriek Solutions, we unpacked how that moment changed everything. She grew up in a blue-collar mill town where you figured things out instead of hiring experts. That scrappy mindset helped her build businesses, but it also led to underpricing, overworking, and way too many spreadsheets. We talk about why "charge what you're worth" misses the point, how businesses will gladly take every ounce of your time if you let them, and why your strategy and financials have to line up if you want profit and a life. If you've ever said yes too quickly or felt busy but not profitable, this conversation will feel uncomfortably familiar, in a good way. What Comes Up When Consultants Talk Shop How Michele's scrappy upbringing shaped her instinct to figure it out first and charge later The moment she realized she was losing money in her dream job and why it forced a major pricing shift Why "charge what you're worth" is bad advice (and what to focus on instead) The hidden mistake most consultants make when pricing work that comes easily to them How spreadsheets went from a helpful tool to a full-blown nightmare and sparked the creation of a SaaS platform Why data for data's sake is useless without a clear strategy and life goal behind it How to stop letting your business consume all your time, energy, and attention The importance of building a business that supports your life, not one you need to escape from Why profitability, planning, and joy actually do belong in the same conversation   ABOUT MICHELE WILLIAMS:  Owner of Scarlet Thread Consulting and Metrique Solutions that empower creative professionals  Learn more about her consulting https://www.scarletthreadconsulting.com Learn about her Money Dashboard https://www.metriquesolutions.com IG - @scarletthreadatl, @Metrique Solutions Facebook – Scarlet Thread Consulting, Metrique Solutions LinkedIn - https://www.linkedin.com/in/michele-williams-business-coach/   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 comes 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

Jack pulls up a chair with Cassandra D'Alessio, founder and Chief Content Strategist at Next Page Brand Strategies, for a conversation that proves most successful consulting businesses don't start polished; they start scrappy. Cassandra shares how growing up constantly moving, working early retail jobs, navigating teaching, corporate life, and eventually launching her own business all built the adaptability she relies on today. The conversation moves from early career missteps and confidence-building moments to lessons learned from tough clients, contracts, and figuring out how to grow a business without losing your sanity in the process. Along the way, Jack and Cassandra trade stories, laugh through rapid-fire personality questions, and unpack how storytelling and data work together to help businesses make smarter decisions. It's honest, funny, and packed with relatable moments for anyone who's ever wondered if everyone else is secretly figuring it out as they go, too. What Comes Up When Consultants Talk Shop Cassandra's unconventional path from teaching to entrepreneurship How constant relocation as a child built scrappiness and adaptability Early career jobs that shaped her work ethic (including floral and liquor store retail) Lessons learned from difficult client relationships and enforcing contracts Why onboarding meetings still matter in person Inbox management and personal productivity habits How marketing storytelling and analytics work together Cassandra's approach to content strategy for service businesses A rapid-fire look at consultant personalities and working styles ABOUT CASSANDRA D'ALESSIO:  Founder & Chief Content Strategist, Next Page Brand Strategies Learn more about Cassandra and connect at https://www.turnthenextpage.com/ Website: https://www.cassandradalessio.com/ Facebook: https://www.facebook.com/AuthorCassandraDAlessio/ LinkedIn: https://www.linkedin.com/in/cassandra-dalessio/ Insta: https://www.instagram.com/author_cassandra_dalessio   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 comes 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.  

This isn't your typical business podcast. It's a business-and-comedy crossover where 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, and unpack how their personality shows up in their business today. We'll determine whether they're scrappy or sophisticated through a series of fun stories. Along the way, we pull random questions, laugh at corporate nonsense, solve an actual data problem, and get to know their business in a way they've never described it before. No fluff, no canned answers, just fun, genuine conversation, with a dash of entrepreneurial lessons. 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.