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

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by Pineapple Jack

5.0(1 reviews)
44 episodes
Updated Daily
Accepts GuestsHas SponsorsLocation 🇺🇸

Podcast Overview

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.

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Publishing Since

2/19/2026

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Recent Episodes

Episode thumbnail for 43. Stop Chasing Leads and Start Generating Clients with Lindsey Wagnon

July 26, 2026

43. Stop Chasing Leads and Start Generating Clients with Lindsey Wagnon

<p>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).</p> <p>Chapters:<br /> 00:00 - Intro and the scrappy vs sophisticated question<br /> 03:17 - Growing up in Southwest Virginia and her dad's sales instincts<br /> 08:22 - Networking anxiety and how to exit a conversation gracefully<br /> 12:16 - Leaving corporate in August 2019 to go out on her own<br /> 19:41 - Pushing back in corporate and why she'd be a bad employee now<br /> 24:05 - Finding her ideal client and what the Valley of Death looks like<br /> 29:14 - Systems, ownership, and lead generation vs client generation<br /> 35:36 - Lightning round: inbox habits, desk setup, and office quirks<br /> 43:51 - Scrappy vs sophisticated verdict and what's next for her business</p> <p>Connect with Lindsey Wagnon:<br /> https://www.linkedin.com/in/lrwagnon/<br /> https://lindseywagnon.com<br /> https://www.instagram.com/lindseywagnonmarketing</p> <p>Connect with Jack Tompkins:<br /> https://www.linkedin.com/in/jack-tompkins/<br /> https://www.pineapplecf.com<br /> https://www.pineappleanalyst.ai/<br /> https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng</p>

Episode thumbnail for 42. Why Your Money Mindset Is Costing You Six Figures with Joel Salomon

July 26, 2026

42. Why Your Money Mindset Is Costing You Six Figures with Joel Salomon

<p>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.</p> <p>Chapters:<br /> 0:00 Intro and scrappy vs sophisticated<br /> 1:47 Growing up with entrepreneurial parents and a shifting money mindset<br /> 8:49 Early jobs, first money memories, and lessons on the value of a dollar<br /> 15:32 Landing the dream job at Citigroup right before the 2008 crash<br /> 21:41 Getting laid off and launching a hedge fund with no money lined up<br /> 25:01 Acting as if: faking momentum until the funding came through<br /> 27:54 From managing $700 million to coaching a $50-an-hour rate increase<br /> 31:54 The money mindset issue behind clients who don't track their own numbers<br /> 36:39 Gratitude, happy habits, and rewiring your brain for prosperity<br /> 39:59 Lightning round and final scrappy vs sophisticated verdict</p> <p>Joel Salomon:<br /> Website: https://www.salaurmor.com/<br /> LinkedIn: https://www.linkedin.com/in/joel-salomon/<br /> Facebook: https://www.facebook.com/JoelProsperitySalomon<br /> Facebook: https://www.facebook.com/thejoelsalomon<br /> Instagram: https://www.instagram.com/joelprosperitysalomon/<br /> TikTok: search "joelprosperitysalomon"<br /> TEDx Talk: https://www.youtube.com/watch?v=0QgT2FmqmfA</p> <p>Jack Tompkins:<br /> LinkedIn: https://www.linkedin.com/in/jack-tompkins/<br /> Consulting: https://www.pineapplecf.com<br /> AI Analyst Product: https://www.pineappleanalyst.ai/<br /> YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng</p>

Episode thumbnail for 41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier

July 26, 2026

41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier

<p>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.</p> <p>Chapters:<br /> 00:00 Introduction and fun fact about Oceanside<br /> 01:14 Scrappy on the inside, sophisticated on the outside<br /> 02:37 Six weeks in an RV and an ant invasion<br /> 09:40 Growing up one of six entrepreneurial siblings<br /> 16:33 From CPA to fractional CFO and COO<br /> 18:02 Proving weekly value to CEOs and boards<br /> 24:38 Scrappy marketing: flyers, cold calls, and a radio show<br /> 30:00 Naming OwlPoint and the CFO to COO pivot<br /> 34:20 Lightning round: contracts, mornings, and cracked screens<br /> 43:41 Closing thoughts and where to find Mark</p> <p>Mark Masquelier<br /> LinkedIn: https://www.linkedin.com/in/mark-masquelier-cpa-296984196/<br /> Consulting: https://owlpoint.net/</p> <p>Jack Tompkins<br /> LinkedIn: https://www.linkedin.com/in/jack-tompkins/<br /> Consulting: https://www.pineapplecf.com<br /> AI Analyst Product: https://www.pineappleanalyst.ai/<br /> YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng</p>

44 total episodes available

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

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.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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