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

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 founded Inviscid Consulting, a supply chain and warehouse operations firm that has since worked with clients ranging from $80B corporations to PE-backed startups. What started as turning over rocks with a small network has grown into 21 year...

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 parents with formal PowerPoint presentations for Christmas gifts, La Tonya's scrappiness has always been strategic. Today she's the founder of Harmony Consulting Group, a fractional COO, AI strategist, and host of the podcast Systems That Set...

What happens when a near-death experience on a Manhattan construction site becomes the catalyst for a career in sales — and eventually a global consulting company? Stephen Steers, founder of Steers Consulting Group, comedian, keynote speaker, and author of Superpower Storytelling , joins Jack to trace the scrappy origins of an unlikely entrepreneur. From flipping yard sale finds on Craigslist to a...

Finance pros are notorious for hiding behind spreadsheets — but what happens when one of their own decides to call that out? John Sanchez went from military kid moving 12 times before graduation, to doing M&A deals at Blockbuster, to accidentally stumbling into entrepreneurship, to becoming one of the go-to communication trainers in accounting and finance. Turns out the bar is low — and he's made...

Scrappy Beginnings, Sophisticated Strategy — ft. Neel Singh of Tropoly What do hand-drawn comic book ads, a secret stack of freelance business cards at a bank job, and a drunk chef have in common? They're all chapters in Neel Singh's story — and they're exactly why he's one of the most interesting people in B2B marketing today. Neel is the Managing Partner and Founder of Tropoly, a former CMO, and...

What happens when someone who grew up in a tiny mining town of 1,500 people ends up becoming a trusted profit strategist for home service businesses? Diane Gardner's story is a scrappy one. She didn't grow up around entrepreneurs. Her dad worked in the mines and believed in practical skills like learning to drive a manual truck on a hillside before she could ever take the wheel. A chance connectio...

What happens when a self-proclaimed lazy kid who once walked out of high school ends up running an award-winning IT company? That is exactly what Isaac Alexander unpacks in this conversation. Isaac is the President of Quo Vadis, Charlotte's Best IT Provider for 2025, and a former mortgage sales leader who helped scale a company from four people to more than one hundred almost overnight. From a fat...

Ever find yourself staring into the fridge after a long day, trying to figure out what you should eat, only to give up and grab whatever is easiest? That tug-of-war between eating healthy and just surviving the week is exactly what this conversation gets into. For this episode of Scrappy But Successful, I'm joined by longtime friend and registered dietitian Kasey Strouse, founder of Normally Nouri...

You can work your tail off… and still lose money in your "dream job." That's the uncomfortable realization Michele Williams had after years of doing work she loved, only to discover she wasn't actually charging for the most valuable part of it: her thinking. When I sat down with Michele, a two-time founder and the force behind Scarlet Thread Consulting and Matriek Solutions, we unpacked how that m...

Jack pulls up a chair with Cassandra D'Alessio, founder and Chief Content Strategist at Next Page Brand Strategies, for a conversation that proves most successful consulting businesses don't start polished; they start scrappy. Cassandra shares how growing up constantly moving, working early retail jobs, navigating teaching, corporate life, and eventually launching her own business all built the ad...

This isn't your typical business podcast. It's a business-and-comedy crossover where 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, and unpack how their personality shows up in their business today. We'll determine whether they're scrappy or sophisticated through a series of fun stories. Alo...