17. From Sheep Ranch to Amazon: Mastering the Scrappy-Sophisticated Spectrum with Tina Dao

27. How to Unlock Hidden Warehouse Capacity Without Spending a Dime with Adrian Betts

Adrian Betts is the founder of Xpandur, where he helps mid-market warehouses unlock hidden capacity and drive profitability without adding headcount, equipment, or new technology. With a background leading high-volume, tight-margin operations, he specializes in eliminating bottlenecks, aligning teams, and turning chaotic warehouse floors into consistently high-performing systems. In this episode, Adrian drops analogy after analogy - and every single one lands. Chapters: 00:00 - Intro and scrappy or sophisticated 01:04 - Growing up scrappy: Atlanta roots and a family of entrepreneurs 03:51 - Early jobs, bad grades in science, and learning to show your work 07:47 - Unlearning perfectionism and the baseball batting average mindset 10:37 - From aviation dreams to consulting: the 2004 start and 2017 restart 14:23 - Building a client base through word of mouth and water cooler credibility 20:46 - ICP evolution: why Adrian now says no to Enterprise and SMB 23:39 - How Adrian actually unlocks capacity in a warehouse - the full method 27:06 - Measuring performance with throughput rates, order accuracy, and cube 32:48 - Scrappy vs sophisticated: airports, inbox chaos, and the file naming system Adrian Betts / Xpandur: https://www.linkedin.com/in/adrianbetts/ [https://www.linkedin.com/in/adrianbetts/] https://xpandur.com [https://xpandur.com] Jack Tompkins / Pineapple Consulting Firm: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineappleanalyst.ai/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

26. How B2B SaaS Companies Leave Money on the Table with Bill Wilson

Bill Wilson has built and sold two companies, helped dozens of B2B SaaS founders fix their pricing, and started a brand-new business while walking through a market in southern Spain. He joins Jack to break down why most pricing problems are actually positioning problems, what scrappy founders get wrong about churn math, and how to start a testable company in a single afternoon with AI. Chapters: 00:00 - Intro and scrappy vs sophisticated 01:09 - Growing up across Canada and the entrepreneur in the family 02:40 - First company at 18, swearing off business, then getting pulled back in 04:35 - Halifax co-working scene and the accidental birth of Mindsea 06:38 - Collaborative consortiums, committed co-discovery, and lessons from trying to share work 07:48 - How SalesRight was born from an internal tool and got acquired by FastSpring 10:19 - What Pace Pricing does - end-to-end pricing strategy for B2B SaaS 11:31 - The most common pricing problem - flatline growth, churn math, and expansion revenue 13:46 - Why pricing confidence comes from conviction, not just data 14:40 - Four levels of pricing validation and how to get there scrappily 17:32 - Jobs to be done, customer interviews, and using AI to analyze them 22:43 - AI in hiring, irresponsible NOT to use AI, and democratizing knowledge 25:40 - AI native vs AI forward, human-led AI-assisted 27:51 - Starting a business in Spain in one afternoon with Claude and landing pages 33:01 - Committed co-discovery - 90 days, 50/50, and why stealth mode is dead 35:08 - Trust as the real moat in AI businesses 37:00 - Love them, help them, pay you - the three things that matter 38:01 - Lightning round: airport anxiety, business class, couch work, inbox zero Bill Wilson Links: LinkedIn: https://ca.linkedin.com/in/wdrwilson [https://ca.linkedin.com/in/wdrwilson] Company: https://www.pacepricing.com [https://www.pacepricing.com] Blog: https://www.pacepricing.com/blog [https://www.pacepricing.com/blog] Jack Tompkins Links: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] Consulting: https://www.pineapplecf.com [https://www.pineapplecf.com] AI Analyst product: https://www.pineappleanalyst.ai/ [https://www.pineapplejacktompkins.com/] YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

25. The Anti-Slop Builder: What 25,000 Hours of AI Looks Like with Piyanka Jain

Piyanka Jain has been building AI models since 2002 - before "AI" was a buzzword. Today she's the CEO of AskEnola, an agentic AI platform that automates the entire CFO workflow: closing books, P&L reporting, MRR schedules, and investor reporting - all with high-fidelity output that doesn't hallucinate. In this episode, Piyanka talks about what 25,000 hours of building actually looks like, why she walked away from enterprise deals to chase mid-cap CFOs, and what "sophisticated in all the right ways" means when your go-to-market is still 100% scrappy hustle. Chapters: 00:00 - Sophisticated Where It Counts, Scrappy Everywhere Else 01:38 - Real AI at Scale: 7-Eleven ATMs and Kiva Donations 04:38 - Warrior Class to Business Class: Piyanka's Origin Story 07:45 - Transformation as the True Motivation 11:52 - What AskEnola Actually Does for CFOs 15:21 - 25,000 Hours, Multiple Pivots, One Winning Bet 20:15 - The SaaStr Slop Problem and the Trust Deficit 25:46 - When Do You Know It's Ready to Ship? 33:53 - Scrappy vs Sophisticated: The Rapid Fire Round 38:19 - Hustling Into the Right Rooms and Manifesting the Right Clients 44:24 - Productivity vs Presence: Slowing Down to Feel Worthy Connect with Piyanka Jain: https://www.linkedin.com/in/piyanka/ [https://www.linkedin.com/in/piyanka/] https://www.askenola.ai [https://www.askenola.ai] Connect with Jack Tompkins: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineapplejacktompkins.com/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

24. 100% Scrappy: How Drew Dowd Diagnoses Broken Businesses and Grows Them

Drew Dowd has built his career walking into broken businesses and finding the one thing everyone else missed. As founder of D2 Operations Consulting, he works with early and growth-stage companies on revenue operations, team execution, and GTM strategy - and his take is that most business problems aren't execution problems. They're information problems wearing an execution costume. Jack and Drew dig into constraint-based thinking, when to document and when not to, and what it really takes to scale a company without over-engineering it. Chapters: 0:00 - Intro and the scrappy vs. sophisticated question 1:00 - Growing up in rural Missouri and early scrappy roots 3:35 - Cold door-to-door selling discount cards in high school 4:51 - First jobs: froyo, food trucks, and a lemonade-to-burger empire 7:34 - Data-driven operations lessons from a food truck mad scientist 11:05 - How a punishment hack in elementary school predicted a systems career 13:10 - Finding the real constraint: the outbound dialing case study 17:14 - You can't prescribe dosages until you understand mechanisms 19:13 - Centralization over complexity: the simple fix for broken ops 22:04 - SOPs, trust, and the Google Doc that scaled a company to $1M/month 28:01 - Struggle days, bad calls, and failing fast 31:36 - Launch at 50% or wait for 90%? Speed vs. structure debate 34:10 - Lightning round: scrappy vs. sophisticated habits 38:00 - ADHD, notebooks, and why pen and paper beats Notion 41:47 - Defining success: profit volume, ethics, and the stabilize-vs-grow mindset 44:49 - Data tells you where to look, not what to do 45:08 - How to connect with Drew Connect with Drew Dowd: https://drewdowd.com [https://drewdowd.com] https://www.linkedin.com/in/drewdowd/ [https://www.linkedin.com/in/drewdowd/] https://x.com/DrewDowd [https://x.com/DrewDowd] Connect with Jack: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] https://www.pineapplecf.com [https://www.pineapplecf.com] https://www.pineappleanalyst.ai/ [https://www.pineapplejacktompkins.com/] https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]

23. From Hot Dogs to Wall Street: Building a Finance Business That Actually Scales with Donny Mashiach

Donny Mashiach is the Founder and CEO of Warrior Group, a finance services firm helping founder-led, scaling businesses install stronger financial infrastructure through fractional CFO, bookkeeping, controller, and strategic consulting services. Donny started his entrepreneurial journey running a kosher food concessions operation at Wrigley Field before moving through investment banking on Wall Street - working on billion-dollar deals in industrials and beyond. Three years ago he founded Warrior Group and has since grown to 15 CFOs and 15 analysts, with a sharp focus on fashion and apparel brands scaling past $5M. In this episode, Donny and Jack dig into why the thing that gets you to $1M is exactly what breaks you at $10M, how to quantify every opportunity in your business, and what it actually looks like to build financial infrastructure that drives decisions - not just reports. Chapters: 00:06 - Scrappy vs. Sophisticated: Donny's Take 01:45 - Growing Up Entrepreneurial in Chicago 03:30 - From Investment Banking to Warrior Group 04:48 - Getting the Wrigley Field Contract in 3 Days 07:37 - From Zero to 35 Clients: How Warrior Group Scaled 10:36 - Why Founders Wait Too Long to Start 13:28 - The Scrappy Win That Felt Better Than $50K Contracts 16:22 - Fashion and Apparel: The New ICP 19:23 - What a Real Fractional CFO Actually Does 22:01 - Building the Roadmap from the Founder's Why 25:00 - Finding $1M in Obsolete Inventory from the Numbers 27:04 - Scrappy vs. Sophisticated Lightning Round 33:24 - Deep Work at 3am and Pushing the Business Forward 35:34 - Where to Find Donny and Warrior Group Guest Links: Website: https://warriorgp.com [https://warriorgp.com] Instagram: https://www.instagram.com/donnymashiach [https://www.instagram.com/donnymashiach] Connect with Jack: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ [https://www.linkedin.com/in/jack-tompkins/] Company: https://www.pineapplecf.com [https://www.pineapplecf.com] Pineapple Analyst: https://www.pineappleanalyst.ai/ [https://www.pineapplejacktompkins.com/] YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng [https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng]