Insights

Full episode here: https://youtu.be/ICmTqyss1v4

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 - AIM (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

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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

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