Shows / Scrappy but Successful [Consultant's Personalities When No One's Watching]
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…
Episodes
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
68. Unclogging Dental Cash Flow: The CFO Who Hates Algebra with Melissa Leavitt
Melissa Leavitt started out as a dental assistant, spent 15 years in corporate finance, and now runs Keystone Advisors, a fractional CFO advisory firm for…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
67. From selling in 5th grade to leading CAS for the biggest accounting firms with Deb Defer
Deb Defer is the Director of Client Advisory Services (CAS) at Woodard, where she helps accounting firms modernize and build real advisory practices instead of…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
66. From Sewing Jeans at 10 yrs old to Building a Blue Collar AI Agent with Sandra Carlisle
Sandra Carlisle has been an entrepreneur since she was 10 years old, hemming pants and lining a customer's jeans with flannel. From there she cleaned houses on…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
65. Why Independent CPA Firms Should Think Twice About Private Equity with Erin Daiber
Erin Daiber is the founder and CEO of Well Balanced Accountants, a boutique consulting firm staffed entirely by people with accounting and finance backgrounds…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
64. How a Marketer Ended Up Selling Spray Drones to NASA with Aruna Inalsingh
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
63. Ethical Selling Wins: Listening, Calibration, and Human Connection with Sue Barrett
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
62. AI Can't Close Your Deals: Selling Into the Trust Gap with Gus Byleveld
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
61. Hustle to Engine: Building a Sales Machine Beyond the Founder with Matt Lauro
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
60. The People and Process Playbook for CPA Firms with Will Hill
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
59. Why She Never Took a Client Outside CPG with Abby June Richards
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
58. Reality Is Undefeated: Lessons from Six Exits with Russ Sorrells
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
57. From Metal Bands to Legal Marketing: The LegalFenix Story with Ron Latz
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
56. Space Robotics to Strategic Advisor with Katie Bedford
Katie Bedford spent seven years as an aerospace engineer building space robotics before pivoting through digital agencies, project management, and five years…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
55. Fractional CSO Secrets from Chief Outsiders with Aaron Gutowski
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
54. Nine Revenue Streams and One Referral Rule with Tina Ruark-Baker
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
53. The Accidental Salesman Who Won Over Chick-fil-A with John Buckner
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
52. Six Months on the Floor, Then a Business with Jocelyn Singer-Sargent
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
51. Lawyer, Auditor, Fractional CFO: The Scrappy Path with Rob Bankey
Rob Bankey is the founder of Bankey & Co., a Washington, DC fractional CFO and transaction advisory practice serving growth-stage SaaS, fintech, and AI…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
50. The NFL, Wall Street, Hollywood, and The Standard with Cris D'Annunzio
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
49. Turning Donor Gifts Into Loyalty That Lasts with Alison Jeffrey
Alison Jeffrey is the founder of Alison Jeffrey Consulting, a fundraising strategy practice working exclusively with nonprofits. After 25+ years in the sector…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
48. From Goldman Sachs to Fractional CFO for Small Business with Oscar Casanova
Oscar Casanova is the founder of Eververdant Growth Partners, a fractional CFO advisory firm helping lower middle-market business owners make sharper financial…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
47. From Homebuilder to Fractional CFO: 30 Years of Scrappy Lessons with Mark Dunaway
Mark Dunaway spent 30+ years leading finance and operations for some of the country's top residential homebuilders - and then walked away from all of it to…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
46. Blind Spots, Business Therapy, and the Art of Scrappy Leadership with Sean McColl
Sean McColl is the founder of Trusted Business Advisors in Charleston, South Carolina. After more than 20 years as a top-performing sales leader - selling…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
45. From CNC Shops to Saudi Royalty: How Minds on Fire Got Here with Marcus Gaughan
Marcus Gaughan started his entrepreneurial journey at 19 with a portable eye therapy device that nearly launched with Iris as a strategic partner - until a…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
44. From Tornado to Thriving Agency with Priscilla McKinney
Priscilla McKinney is the CEO ("Momma Bird") of Little Bird Marketing, a LinkedIn influencer, a trained cultural anthropologist, and the host of her own…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
43. Stop Chasing Leads and Start Generating Clients with Lindsey Wagnon
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
42. Why Your Money Mindset Is Costing You Six Figures with Joel Salomon
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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
41. The Owl Point Story: Scrappy Consulting Wisdom with Mark Masquelier
Mark Masquelier is the founder of Owl Point, a fractional CFO and COO advisory firm helping CEOs and boards navigate business growth through financial…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
40. Scrappy Roofer to Executive Coaching with Andy Brown
Andy Brown grew up carrying shingles up a ladder at eleven years old on his family's roofing crew in North Louisiana. Thirty years later, he's a Fractional COO…
Scrappy but Successful [Consultant's Personalities When No One's Watching]39. From Medieval History to the C-Suite with Debbie Plager
Debbie Plager, Founder and CEO of The Plager Group, joins the show to talk about how a medieval history degree turned into a 25-year career in corporate talent…
Scrappy but Successful [Consultant's Personalities When No One's Watching]38. Fractional COO Beata Rouleau on Scaling Without the Bloat
Beata Rouleau is the founder of Compass Consulting, a fractional COO practice that helps tech companies between $1M and $20M in revenue build the strategies…
Scrappy but Successful [Consultant's Personalities When No One's Watching]37. Sophisticatedly Scrappy: 10 Years of Beyond the Chaos with Susan Fennema
Jack sits down with Susan Fennema, the self-proclaimed "Chaos Eradicating Officer" and founder of Beyond the Chaos, to find out if she is more sophisticated or…
Scrappy but Successful [Consultant's Personalities When No One's Watching]36. Why Relationships Beat Sales Pipelines with Anna McGovern
Anna McGovern spent 23 years climbing the ranks at Unilever, from local supply chains all the way to global, before trading Park Avenue for her own consulting…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
35. What Buyers Actually Look for in a Business with Eric Harrison
Eric Harrison spent his entire life in the women's shoe business, growing up in his family's wholesale distribution company before taking over from his dad in…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
34. Hire Your Replacement: The Honest Way to Build Client Trust with John Rodriguez
John Rodriguez is the co-founder of Valiant, a firm that embeds Big Four level financial expertise directly into startup teams instead of operating as a black…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
33. The $1M-$10M Businesses PE Ignores (And Why That's the Opportunity) with Charlie Warden
Charlie Warden is the Managing Partner of Warden Strategy, a revenue strategy and venture-building firm based in Denver. He's a fractional CGO (Chief Growth…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
32. Why Early Hires Matter More Than You Think with Alexandra Erman
Jack Tompkins sits down with Alexandra Erman, a startup operator who has spent two decades building the infrastructure that lets venture-backed companies scale…
Scrappy but Successful [Consultant's Personalities When No One's Watching]30. Why Most Small Business Marketing Misses the Mark with Jen Best
Jennifer Best is the founder of Copper Compass Group, a fractional marketing firm helping small businesses and startups build real marketing strategy instead…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
31. Stop Building Yourself Another Job: Fractional CXO Company Building with Natalie Hoop
In this episode of Scrappy But Successful, Jack sits down with Natalie Hoop, a fractional COO and coach for fractional consultants, to unpack what it really…
Scrappy but Successful [Consultant's Personalities When No One's Watching]29. Why More Leads Won't Fix Your Sales Problem with Paul Pompeo
Paul Pompeo is a New York sales guy through and through - born and raised in Queens, started his first business running a paper route crew at age eleven, and…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
28. Building a Business That Doesn't Run Through You with Shay Prosser
Hey consultants and fractional professionals - this is the episode where strategy meets scrappiness. Shay Prosser founded North 12 Partners after realizing…
Scrappy but Successful [Consultant's Personalities When No One's Watching]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…
Scrappy but Successful [Consultant's Personalities When No One's Watching]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…
Scrappy but Successful [Consultant's Personalities When No One's Watching]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…
Scrappy but Successful [Consultant's Personalities When No One's Watching]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…
- Scrappy but Successful [Consultant's Personalities When No One's Watching]
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…
Scrappy but Successful [Consultant's Personalities When No One's Watching]22. Candy, Lawn Care, and Claude Code: Joe Siegel's Wild Road to Fractional CFO & Numvex
From candy dealer to fractional CFO to AI SaaS founder - Joe Siegel, founder of Greenlight Financial Group, has been hustling since he was slinging pixie…
Scrappy but Successful [Consultant's Personalities When No One's Watching]21. The 80/20 Rule That Will Change How You Look at Your Clients with Scott Peterson
Scott Peterson walked onto the Oregon State basketball team by leaving messages on the coach's home phone until someone called back. He started his sales…
Scrappy but Successful [Consultant's Personalities When No One's Watching]20. Scrappy by Design: How an Anthropologist Became the World's Innovation Storytelling Expert with Susan Linder
Susan Linder is not your typical consultant. A cultural anthropologist from the Bronx who hitchhiked through Central American war zones, trained as an AIDS…
Scrappy but Successful [Consultant's Personalities When No One's Watching]19. The 6-Part Marketing Engine Every Indie Game Studio Needs with Jay Rooney
Jay Rooney is the founder of Spawn Point Marketing, a fractional CMO practice for indie and AA game studios, and the publisher of Game & Word - an…
Scrappy but Successful [Consultant's Personalities When No One's Watching]18. Why 45,000 Australian Business Owners Walk Away With Nothing with Eric Tjoeng
Eric Tjoeng grew up in Indonesia in a family of seven entrepreneurs, started his first business venture at age 12 promoting a comedy show, and eventually moved…
Scrappy but Successful [Consultant's Personalities When No One's Watching]17. From Sheep Ranch to Amazon: Mastering the Scrappy-Sophisticated Spectrum with Tina Dao
What does it really take to build a business that creates higher returns AND more joy? Tina Dao, founder of Liberated Leaders, has lived the answer - from…
Scrappy but Successful [Consultant's Personalities When No One's Watching]16. Ending Random Acts of Marketing with a Brand Operating System with Tanner Rankin
What happens when a corporate employee discovers Amazon, teaches himself e-commerce, becomes a CMO, and then realizes the whole agency model is broken? You get…
Scrappy but Successful [Consultant's Personalities When No One's Watching]15. 3-Step Framework for Growing Home Service Businesses with Phil Risher
Phil Risher didn't have entrepreneurs in the family - he had a single mom, a pest control dad, a rap career in high school, and eventually a school bus he…
Scrappy but Successful [Consultant's Personalities When No One's Watching]14. The Body Keeps the Score in Business with Elizabeth Rose
Elizabeth Rose is President and Lead Coach at Garth Rose Consulting Group, where she brings 27 years of mediation experience and a decade of executive coaching…
Scrappy but Successful [Consultant's Personalities When No One's Watching]13. From Social Worker to State Champ: Building Teams That Win with Nick Reich
Nick Reich is the co-founder of Abundant Empowerment and the founder of CoLab - a peer-powered community for consultants and leaders. A first-gen college kid…
Scrappy but Successful [Consultant's Personalities When No One's Watching]12. From the Mug Bug to CX Expert - The Scrappy Path of Ryen Salo
Ryen Salo is the Client Experience Manager at CherryBecker, a 10-year CX veteran, Association for Accounting Marketing (AAM) member and speaker, Finnish sauna…
Scrappy but Successful [Consultant's Personalities When No One's Watching]11. From Paper Routes to $2 Billion - The King of Capital Breaks It All Down with Brad Blazar
What do a $180 driveway shoveling gig, a fake million dollar bill at the Houston airport, and raising over $2 billion in capital all have in common? Brad…
Scrappy but Successful [Consultant's Personalities When No One's Watching]10. The Supply Chain Consultant Who Testifies in Court with Steve Hopper
Steve Hopper spent years climbing the corporate ladder before a toxic work environment - and a nudge from his wife - pushed him to bet on himself. In 2004, he…
Scrappy but Successful [Consultant's Personalities When No One's Watching]9. The Scrappy Strategist: How La Tonya Roberts Went from Cosmetologist to COO with La Tonya Roberts
La Tonya Roberts has always had a plan - and the grit to execute it. From running a lemonade stand outside a military base in Alaska at age 7 to pitching her…