Insights

Is Aruna Inalsingh successful because she's sophisticated or because she's a little bit scrappy? Jack sits down with the fractional CMO and founding member of TerraNav Spray Drones to find out. Her first answer is that it's all relative, which fits a conversation that ends up on the moon. Aruna explains what a spray drone actually is, how an engineer turned marketer ended up in agriculture, and what she saw at a NASA conference about drones built for moon base operations. She also shares why she puts process ahead of strategy, how she keeps several businesses moving at once (including a brand-new venture called Life's Guardrails that helps families plan for aging), and where TerraNav is headed as it moves toward manufacturing in Northwest Arkansas. Chapters: 0:00:00 Sophisticated or scrappy? Aruna weighs in 0:02:22 What is a spray drone, and how did a marketer end up here? 0:06:25 Space drones and moon base at NASA 0:08:42 Growing up in Trinidad and Baltimore, plus basement dance shows 0:12:00 Her businesses, including the new Life's Guardrails 0:16:16 Balancing it all: strategy vs. execution in the AI era 0:21:44 People, process, strategy, product: what comes first? 0:27:48 TerraNav's roadmap: Arkansas manufacturing and funding 0:33:27 The verdict: scrappy or sophisticated? Aruna's links: Website: https://terranav.aero LinkedIn: https://www.linkedin.com/in/arunainalsingh YouTube: https://youtube.com/@terranavspraydrones Facebook: https://www.facebook.com/share/1GWT5iMwRm/ Instagram: https://www.instagram.com/terranavspraydrones Jack's links: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Is Sue Barrett successful today because she is sophisticated, or because she is a little bit scrappy? In this episode of Scrappy But Successful, Jack Tompkins sits down with the founder and CEO of Barrett Consulting Group and the Selling Better movement, one of Australia's most distinctive voices on ethical, human-centered sales, who has trained over 50,000 professionals across five continents. Sue takes us from school holidays in her father's timber business, where she learned not to be intimidated by skeptical builders, to landing her first $10,000 sale in her first week in business. Along the way she explains why listening and asking better questions beats throwing information at buyers, why most businesses fail to produce content that convinces a buyer to choose them, and how consultants and small business owners can sell more effectively in the age of AI without losing the human connection. Chapters: 0:00 Welcome, an Australian fun fact, and meet Sue Barrett 3:46 Growing up in the family timber business 7:57 Selling with humanity: listening, calibrating, and the 75% content gap 15:43 The double gap: in-person conversations and online presence 19:17 Vendor-neutral matchmaking and the used car salesman problem 21:54 Testing ideas, using AI, and doing your homework first 24:09 Starting out in 1995 and landing the first $10,000 sale 31:41 What Barrett does today: go-to-market, sales process mapping, AI and CRM 33:40 Selling what you have not done yet, and unlearning stage fright 38:52 One tip for more effective selling and where to find Sue Connect with Sue Barrett: Website: https://www.suebarrett.com/ Barrett Consulting Group: https://www.barrett.com.au/ Selling Better: https://www.sellingbetter.com/ Sell Like A Woman: https://www.selllikeawoman.com/ Substack: https://suebarrett.substack.com/ LinkedIn: https://www.linkedin.com/in/suebarrett1/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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Is a fractional CRO scrappy or sophisticated? Matt Lauro, founder of Fractional CRO in Charlotte, NC, joins Jack Tompkins to find out. With more than a decade and a half in workforce solutions and recruitment, Matt helps founder-led companies build a sales and marketing engine that scales beyond the founder's own relationships. In this episode, Matt explains why hiring a VP of Sales is usually the wrong first move, how he prices fractional work with a flat monthly retainer instead of by the hour, where his clients come from (about a third each from referrals, LinkedIn, and his website), and why the client side of the bow tie model is the most overlooked part of revenue growth. Along the way: lemonade stands, stamp collections, a nine-year-old's Pokemon card lesson, and a scrappy or sophisticated lightning round. The final verdict: 80 percent scrappy, 20 percent sophisticated. Chapters: 0:00:00 Intro and the scrappy vs sophisticated question 0:01:43 Growing up scrappy: lemonade stands, stamps, and Pokemon cards 0:06:20 What a fractional CRO actually does 0:07:31 Why hiring a VP of Sales is usually the wrong move 0:11:44 Leaving corporate and launching on the side 0:18:31 Pricing fractional work with a monthly retainer 0:23:26 First clients, credibility, and fractional partnerships 0:31:50 KPIs and the bow tie model 0:34:41 Scrappy or sophisticated lightning round 0:42:23 The book and Substack: From Hustle to Engine Connect with Matt Lauro: Fractional CRO: https://www.fractionalcro.org LinkedIn: https://www.linkedin.com/in/mattlauro/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Gus Byleveld is the founder of The Wondering and a former CEO and revenue operator with 25+ years of experience building and leading B2B tech companies. He started out as an architect in Cape Town, South Africa, moved into technology sales, worked through a run of startups, and today helps CEOs of growth-stage tech companies figure out why growth is harder than it should be before they decide what to change. In this episode, Jack and Gus dig into why a sales process should be built from the buyer journey, how AI is changing the way buyers size up sellers, and why the real gap in modern selling is trust. Gus shares the discovery question he swears by, why marketing, BDR, and customer success teams need one shared goal, and why activity is not quality. And the big question: is Gus more scrappy or more sophisticated? Jack's verdict: a dash of scrappiness, backed by some seriously sophisticated thinking. Chapters: 0:00 Scrappy or sophisticated? Meet Gus Byleveld 2:53 From Cape Town architect to tech sales 8:02 The Wondering and why buyer journey beats sales process 14:40 Leaving corporate for a mobile trading card startup 19:18 Two schools of thought on AI, then and now 24:25 The trust gap in modern selling 27:23 The discovery question: what does your world look like when I solve this? 34:29 One shared goal for marketing, BDRs, and customer success 38:16 What makes you uniquely qualified? The question AI can't outsource 43:03 Get out of the building, and where to find Gus Connect with Gus: LinkedIn: https://www.linkedin.com/in/gusbyleveld/ The Wondering: https://thewondering.net/ Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

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Will Hill spent 21 years at Thomson Reuters helping build the accounting industry's shift toward advisory services, then left to found Will Hill Consults, LLC, where he coaches CPA firm owners one-on-one at the intersection of people and process. With 25+ years in the industry and hands-on work inside 400+ accounting firms, Will has a rare read on why some firm leadership changes stick and most don't. In this episode, Jack and Will talk about why he refuses to do group coaching, the moment he had to tell two employees their jobs weren't going away even though the software was, how firms make the leap from compliance to advisory conversations, and the scrappy roots (golf-ball hustling included) behind his one-on-one approach today. Chapters: 0:00:00 Intro: scrappy or sophisticated? 0:01:37 Growing up in Flint and selling golf balls for cash 0:04:06 Coaching CPA firms at the intersection of people and process 0:06:18 Why he only coaches one-on-one, never in groups 0:08:12 From janitor and bank teller to 21 years at Thomson Reuters 0:11:38 Asking real questions and earning client trust 0:17:17 Moving firms from compliance to client advisory services 0:20:34 Leaving Thomson Reuters to launch his own consulting firm 0:26:40 Finding his ICP, firing bad-fit clients, staying collaborative 0:35:13 Scrappy vs sophisticated lightning round Will Hill: Website: https://willhillconsults.com/ LinkedIn: https://www.linkedin.com/in/wghill/ Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Abby June Richards is the founder of The CPG CFO, a fractional CFO firm helping emerging, better-for-you and sustainable CPG brands know their numbers and build businesses that last. She spent 15 years in operations before becoming a CPA, then nearly 7 years at RSM across audit, outsourced accounting, and tech implementation, before launching her own firm in 2023 focused exclusively on CPG brands in the $0-50M range. In this episode, Jack and Abby trace her path from being homeschooled as the oldest of six kids in South Texas (where she was literally running a ledger for a game of Little People) to watching her dad's engine-rebuilding business slowly fail, to finally taking the leap and starting her own firm with zero clients. She breaks down her CASH FIGHT framework for CPG cash flow, gets real about the fear and doubt in year one, and explains why she stayed locked into her niche even when easier work was on the table. Chapters: 0:00 Intro and the sophisticated vs scrappy question 3:09 Homeschooled in South Texas as the oldest of six 9:34 What The CPG CFO does for clients today 12:51 College, community college advocacy, and the CPA path 18:41 Early jobs, her dad's failed business, and the leap to starting her own firm 22:07 Zero clients and posting on LinkedIn for 600 days 24:22 Landing the first client and locking in her ICP 28:05 Cash flow, contracts, and the CASH FIGHT framework 35:30 Lightning round: scrappy habits and money mindset 37:25 Branding, the logo, and inside her home office The CPG CFO: https://www.thecpgcfo.com Abby's LinkedIn: https://www.linkedin.com/in/abbyjuner/ The CPG CFO on Instagram: https://www.instagram.com/thecpgcfo/ The CPG CFO on YouTube: https://www.youtube.com/@TheCPGCFO LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Consulting: https://www.pineapplecf.com AI Analyst Product: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng