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

Jocelyn Singer-Sargent is the founder of Jocelyn Singer-Sargent Consulting, known as "the work whisperer." She's an HR consultant, coach, and speaker based in Santa Fe, New Mexico, dual-credentialed as a Licensed Clinical Social Worker and a SHRM-certified HR professional. Her practice spans fractional HR leadership, manager training, employee engagement, and coaching for leaders who want to build people strategies that actually work, including her work on building collaboration "from Boomers to Zoomers."

In this episode, Jocelyn and Jack dig into how she stumbled into HR from a background in clinical social work, why the "employee handbook" is really a mirror of company culture, and how she built her entire consulting practice on word of mouth with zero family entrepreneurial background to draw on. She also gets into the moment she burned out of corporate HR, slept on the floor with her dogs for six months, and used a borrowed contract template to land her first client. It's a scrappy story from start to finish.

Chapters: 0:00 Welcome and Santa Fe fun fact 1:09 Jocelyn's scrappy small town roots 2:46 Growing up in a no entrepreneurs household 6:34 What Jocelyn does for businesses today 9:19 Who her clients are and the 50 employee turning point 11:34 From clinical social work to accidental HR 20:00 Reading a company through its employee handbook 28:24 Burnout, the floor nap era, and starting the business 36:25 Referrals, the dog park network, and speaking engagements 40:07 Scrappy vs sophisticated lightning round

Jocelyn Singer-Sargent's Links: Website: http://www.jocelynsingersargent.com LinkedIn: http://www.linkedin.com/in/jocelyn-singer-sargent-lcsw-shrm-cp-47399849

Jack Tompkins' 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

Rob Bankey is the founder of Bankey & Co., a Washington, DC fractional CFO and transaction advisory practice serving growth-stage SaaS, fintech, and AI companies. He led Contactually through its acquisition by Compass and steered Opower through its NYSE IPO before Oracle bought the company, and in 2023 DCA Live named him one of DC's Tech CFO Stars.

In this episode, Rob and Jack trace his path from an Arthur Andersen offer that evaporated in the firm's collapse, through Big 4 audit work counting inventory at GM and ConAgra, to law school and a brief stint at the SEC that convinced him he wanted to build things rather than review them after the fact. Rob explains how he ended up running finance at an early-stage startup that eventually IPO'd on the NYSE, why he decided to start his own practice instead of chasing another corporate finance track, and how he thinks about proving ongoing value to clients once the systems are running smoothly ("the trains run on time"). They also get into his golden rule for startup timelines, how he built his ICP through simple word-of-mouth referrals, and a lightning round covering everything from color-coded bookmark folders to how many client inboxes one CFO can realistically manage.

Chapters: 0:00 Intro and Scrappy vs Sophisticated 1:43 Growing Up Around the World 7:03 Notre Dame, Japanese, and Landing at Arthur Andersen 10:14 Big 4 Auditing: GM, ConAgra, and the Limits of Audit 13:03 Law School, the SEC, and Finding His Way Back to Finance 17:15 Taking a Startup from First Audit to NYSE IPO 19:45 Starting His Own Fractional CFO Practice 24:59 Proving Value: "The Trains Run on Time" 33:20 Lightning Round: Inside Rob's Office and Inbox 40:55 What's Next and Closing Thoughts

Rob Bankey: Website: https://www.bankey.co/ LinkedIn: https://www.linkedin.com/in/rob-bankey-3268561/

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

Cris D'Annunzio believes the greatest enemy of performance isn't failure, it's drift. He's the founder of Mettle & Method, and his resume reads like four different careers stitched together: NFL player, Wall Street broker, Hollywood actor, and high performance sales coach. Along the way he built "The Standard," a philosophy built on a simple idea: everything decays without deliberate maintenance, so you measure where you are, set a standard, and defend it every single day.

In this episode, Cris walks through an incredible family story that starts with his grandfather surviving a concentration camp in Italy and ending up as a NYC parks gardener, an 18 month cold calling grind on Wall Street where he dialed the phone 250 times a day for 18 straight months, and the honest, sometimes uncomfortable difference between chasing goals and defending standards. He also talks about his work with The CFO Project, training bookkeepers and accountants to become advisors who help small businesses survive past the five year mark.

Chapters: 0:00 Scrappy or sophisticated: Cris weighs in 1:49 Immigrant roots and a hard beginning 6:07 What Cris does today 7:16 His grandfather's story from Naples to Brooklyn 14:43 From the NFL to Wall Street 19:36 250 dials a day for 18 months 24:13 Building "The Standard" 26:26 Goals versus standards 39:00 The one thing that makes a high performer 45:06 Lightning round: scrappy vs sophisticated 47:56 Replayer, The CFO Project, and closing thoughts

Cris D'Annunzio's Links: Mettle & Method: https://www.mettleandmethod.com The CFO Project: https://cfoproject.com LinkedIn: https://www.linkedin.com/in/cris-d-annunzio/

Jack Tompkins' Links: 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

Alison Jeffrey is the founder of Alison Jeffrey Consulting, a fundraising strategy practice working exclusively with nonprofits. After 25+ years in the sector, including years spent in-house, she left a permanent role five years ago to build a boutique consulting practice, working deeply with about 15 clients instead of chasing volume. On this episode, Alison and Jack dig into what it actually means to ask people for money for a living, from six-figure stethoscopes to the emotional weight behind a $10,000 ask.

Alison shares the story of engraving a $100 stethoscope for a billionaire donor (and the handwritten note that came back), why she thinks "philanthropy is self-care," and how she built a practice around being the strategist in the room, not just the person who closes the gift. Jack and Alison also get into a lightning round of scrappy vs sophisticated questions covering everything from grades in school to her minimalist home office.

Chapters: 0:00 Sophisticated or scrappy: Alison's 80-20 rule 2:15 Uncle Joe and the Glasgow china shop 5:52 The engraved stethoscope story 11:24 Growing up in a political but non-entrepreneurial family 13:12 The COVID balcony story that still gets brought up at home 16:00 Setting strategy vs doing the solicitation herself 18:13 Why fundraising isn't really a sales process 24:19 Quitting her job, losing her father, and landing her first client 30:25 Becoming known as the strategist, not just the fundraiser 32:41 Lightning round: scrappy vs sophisticated

Alison Jeffrey's links: Website: https://www.alisonjeffrey.com/ LinkedIn: https://www.linkedin.com/in/alisonjeffrey/

Jack Tompkins' 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

Oscar Casanova is the founder of Eververdant Growth Partners, a fractional CFO advisory firm helping lower middle-market business owners make sharper financial decisions. Before starting his own firm, Oscar closed over $30 billion in deals across Goldman Sachs, high-growth startups, and Shopify - and he brings that same rigor to the small businesses that make up the backbone of the economy.

In this episode, Jack and Oscar dig into Oscar's journey from growing up in Mexico to landing at Goldman Sachs on his fifth application attempt, why he walked away from the corporate path to build something of his own, and the "operating system" mindset he uses to run his life and his firm. They also get into how he actually wins clients (hint: it is not by chasing outcomes), what makes someone coachable, and a full lightning round of scrappy versus sophisticated questions. Oscar lands the verdict for himself by the end - you will have to listen to find out which side he falls on.

Chapters: 0:00 Welcome and fun fact of the day 1:02 Scrappy or sophisticated - Oscar's answer 1:45 Growing up in Mexico and coaching basketball 5:01 What Eververdant Growth Partners does today 5:38 Leaving Mexico for the US in 2011 8:20 Scrappy rapid fire - Tupperware and the four meals 11:23 The "operating system" for life and fitness 12:00 Getting into Goldman Sachs on the fifth try 17:47 Finding Eververdant's first clients through curiosity 23:39 Surrendering the outcome instead of chasing it 30:10 Earning trust as a CFO advisor 35:04 Lightning round - office, inbox, and airport habits 40:04 Final scrappy versus sophisticated verdict

Oscar Casanova: LinkedIn: https://www.linkedin.com/in/oscar-casanova-c/ Eververdant Growth Partners: https://eververdantgrowthpartners.com

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