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

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

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

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

Russ Sorrells has bought, built, and sold six businesses, starting with a machine shop he ran out of his garage as a 21 year old with one electrical outlet and a rotary phase converter that sounded like it was going to take off. Today he is the founder of Beyond the Grind, a certified Pinnacle Business Guide who helps owners get out of the weeds so their teams can actually thrive.

In this episode Russ traces the whole arc: riding along with his sales rep dad in the 80s, raking leaves and mowing lawns as his first hustle, welding a customer's coin die back together at 3am, buying a prosthetics company for a dollar, and eventually building the coaching practice he runs today. Jack and Russ dig into how many goals is too many, why "reality is undefeated," and what it actually takes to get owners to stop doing the thing that is sinking the ship.

Chapters: 0:00 Welcome and the Purdue vs IU rivalry 1:06 Scrappy, sophisticated, or a hot mess 2:29 Small town Indiana roots 2:51 Riding shotgun with his sales rep dad 6:09 First hustle: raking leaves to a garage machine shop 23:09 The coin die disaster and the 3am weld 28:54 Buying a laundromat and a prosthetics company for a dollar 36:23 Lightning round: Star Wars figures and crock pot squirrel 46:52 Beyond the Grind today and where to find Russ

Russ Sorrells: LinkedIn: https://www.linkedin.com/in/russ-sorrells-001391b/

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

Ron Latz is the founder of LegalFenix, a fractional CMO and marketing advisory firm that works exclusively with law firms. After more than 15 years in legal marketing, including stints at FindLaw and Mockingbird Marketing, Ron built LegalFenix into a vendor-neutral shop that helps firms sort out what is actually working in their marketing and what is not.

In this episode, Ron and Jack cover Ron's path from a metal band and umpiring Little League games in New Jersey to running a marketing consultancy built entirely around law firms. They dig into why Ron refuses to take referral fees, how his hiring process still ends with him flying out to meet every candidate in person, and the KPIs his team leans on to prove value to clients month after month. Along the way: dot-net domains, the credit card timing game, and eating cereal out of clean Tupperware.

Chapters: 0:00 Welcome and the scrappy or sophisticated question 1:08 Growing up in New Jersey and an early love of hockey 3:31 Garage sales, fundraising calls, and a band in the emo days 7:42 What LegalFenix does for law firms today 8:47 Landing on legal marketing and staying vendor neutral 10:39 From Xerox to FindLaw to starting Athlete Consulting 14:30 Three name changes and finally landing on LegalFenix 16:35 Leaving agency life and going vendor neutral for good 27:01 Proving value to clients and the KPIs that matter 32:01 Scrappy versus sophisticated lightning round 43:40 Where to find LegalFenix and final thoughts

LegalFenix website: https://legalfenix.com Ron Latz on LinkedIn: https://www.linkedin.com/in/ronlatz/

Jack Tompkins on LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Pineapple Consulting Firm: https://www.pineapplecf.com Pineapple Analyst AI: https://www.pineappleanalyst.ai/ YouTube: https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng

Katie Bedford spent seven years as an aerospace engineer building space robotics before pivoting through digital agencies, project management, and five years as a fractional COO to land where she is today: a strategic advisor and thinking partner for agency leaders. She's the founder of K Bedford Consulting in Vancouver, and her whole approach is built on giving business owners the honest, unbiased conversation they can't get from anyone else on their team.

In this episode, Katie and Jack dig into how an engineering brain wired for risk and rigorous logic became the perfect training ground for advisory work, why so many small businesses mistitle their staff, the real difference between AI-as-pattern-finder and AI-as-judgment-maker, and the emotional weight of helping leaders make the calls they already know they need to make. Katie also shares two tools she built herself using AI (a custom CRM and a cash flow forecaster) and makes a genuinely useful case for why chasing AI tools without a centralized dataset is putting the cart before the horse.

Chapters: 0:00 Scrappy or sophisticated: Katie's answer 1:29 Cinder blocks, jewelry, and Katie's non-entrepreneurial roots 4:13 What a thinking partner actually does 7:33 How the advisory relationship gets structured 9:41 Why small companies over-title their people 13:40 From grade one space obsession to aerospace engineer 14:41 NASA, the Canada Arm, and getting the "get out of jail free" layoff 16:43 The pivot into agency life and finding the thinking partner niche 20:36 Where AI actually helps (and where it can't) 24:04 Building her own CRM and cash flow tool with AI 27:23 The overbuilt website and the box of unused business cards 29:20 Her one scrappy money story: fighting for a business credit card 34:02 The Steve Martin mindset and Katie's rotating hobbies 36:08 Broadening her niche beyond digital agencies 43:09 The Thinking Partner ROI calculator

Katie Bedford: LinkedIn: https://www.linkedin.com/in/katie-bedford/

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

Aaron Gutowski is a Partner and Chief Sales Officer at Chief Outsiders, an "Executives-as-a-Service" firm that places fractional CMOs and CSOs inside mid-market companies. He was one of the first CSOs to join the firm, and he brings more than 20 years of sales leadership experience across data, research, and industrial services to every engagement.

In this episode, Aaron traces his sales instincts back to a Detroit News paper route as a kid, then walks through the hustle that got him his first real sales job selling computers at a company that's now Verizon, including the time he secured a shipment of Apple computers with a PO number made up of his own birthday. He and Jack dig into how Aaron landed his first major client at Chief Outsiders, why the single most important KPI in any sales org is the number of new first meetings (not total meetings), and why honest, sometimes uncomfortable conversations with clients build more trust than telling them what they want to hear.

Chapters: 0:00:00 Intro and meet Aaron Gutowski 0:01:10 Scrappy all the way, growing up in Detroit 0:03:13 The Detroit News paper route hustle 0:06:09 What a fractional CSO actually does 0:09:43 Landing HBS Solutions, his first big client 0:14:45 Selling Apple computers and the birthday PO hustle 0:29:47 Coaching honesty into hard sales conversations 0:31:15 The one KPI that predicts sales success 0:35:10 Lightning round and Chief Outsiders AI program

Connect with Aaron Gutowski: LinkedIn: https://www.linkedin.com/in/aarongutowski/ Chief Outsiders profile: https://www.chiefoutsiders.com/profile/aaron-gutowski

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

Tina Ruark-Baker has already built and sold two companies, spent two decades climbing to the C-suite, and then walked away from the corner office to start a third business from scratch. Today she runs TRB Creative, coaching small businesses, entrepreneurs, and nonprofits on the one channel she believes almost nobody uses correctly: LinkedIn.

In this episode, Tina and Jack trace her path from a staffing company she started at 18 in her dad's basement, through 20 years in New York City, to her current life at the beach in a golf community outside Charlotte. She breaks down why personal LinkedIn profiles outperform company pages, why she said yes to painting an entire medical office (20 canvases, zero prior experience), and how nine different revenue streams stay connected through a single referral-driven philosophy: make the connection, then get out of the way.

Chapters: 0:00 Intro and the scrappy vs sophisticated verdict 1:35 From Detroit hustle to two exits by 1999 3:25 New York, a chance encounter, and 20 years in the city 6:32 Walking away from corporate to coach LinkedIn 9:11 Landing first clients through networking 14:23 Saying yes to a 20-painting art commission 18:18 Nine revenue streams and the power partner network 21:13 Finding the real ICP and ditching marketing-only work 25:23 Scrappy marketing, golf, and keynote speaking 30:45 How Tina measures success and builds client trust

Connect with Tina Ruark-Baker: LinkedIn: https://www.linkedin.com/in/tina-ruark-baker/

TRB Creative: https://www.trbcreative.com/

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

John Buckner is the founder of Insightful Selling and a Fractional VP of Sales advisor at Sales Xceleration, bringing a thirty-year corporate sales and marketing career to small businesses that need to grow. His resume includes DuPont, Chick-fil-A, 7-Eleven, Walmart, and Home Depot, but John calls himself an "accidental salesman" - his path started on his father's land surveying crew in the North Carolina foothills, not a sales floor.

In this episode, John and Jack dig into why the best salespeople act as guides instead of salesmen, with the customer as the hero of their own story. John shares the data-driven pitch that won Chick-fil-A's coffee business away from 23 other roasters, the pharmacy counter interaction that taught him what trust-based selling actually looks like, and why he built his whole practice around single, focused solutions instead of overwhelming clients with everything he offers.

Chapters: 0:00 Welcome and the Lake Norman monster fun fact 0:42 Scrappy or sophisticated - John's 300 CEO outreach push 6:03 Family roots - a land surveyor dad and the family entrepreneurial itch 10:32 Reframing sales - the customer as hero, John as guide 13:44 The shingles shot story - trust-based selling in action 18:24 Early sales instincts - basketball, retail spiffs, and rapport 22:02 Winning Chick-fil-A's coffee business with data and insight 28:20 Getting out of the box - curating your offer instead of overwhelming clients 34:46 Lightning round - garage sales, cash flow games, and inbox habits 40:22 Final takeaway - make the customer your true north

John W. Buckner brings a broad sales and growth background from a thirty-year corporate career, including leadership roles as VP of marketing and SVP of sales, spanning Fortune 500 companies, national middle-market firms, and major retailers including DuPont, Georgia-Pacific, Simpson Strong Tie, Chick-fil-A, Taco Bell, Sonic, 7-Eleven, Walmart, Target, Home Depot, and Lowe's. His firm, Insightful Selling, helps small businesses win through people, process, and technology.

https://LinkedIn.com/in/johnwbuckner

https://www.linkedin.com/in/jack-tompkins/ https://www.pineapplecf.com https://www.pineappleanalyst.ai/ https://www.youtube.com/channel/UCalnj5yLU0ZH9y_tVl1J4ng