8. The Context is the Close - Sales Lessons from a Scrappy yet Sophisticated Stephen Steers

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 advising Google, Nike, and over a thousand companies across 40+ countries, Stephen's story is equal parts hustle and hard-won wisdom. In this episode: Growing up in NYC with Jamaican roots — and why "a man can't leave without keys and money" was Stephen's motto at age six Uncle Willie, $20 Saturdays, and the first real lesson in work ethic Selling popsicles from Costco in high school (300 pack, a quarter a piece — do the math) Construction work, a near-death moment on 6th Ave, and the walk that changed everything Launching a consulting company in 2019 and watching COVID nearly take it all away The Mexico beach reset — and what slowing down actually taught him Context Selling: why what the customer says is truth, and what you say, you must defend Ernest Shackleton, Antarctica, and why this is the book Stephen just finished this week The lightning round: inbox zero, no TSA PreCheck, work clothes at home, and two phone numbers Chapters: 00:03 – Welcome & Fun Fact: Squirrels and Entrepreneur ADD 01:05 – Scrappy or Sophisticated? Stephen's Verdict 02:14 – Growing Up in NYC with Jamaican Roots 04:20 – Uncle Willie, Two Hands & the First $20 05:37 – Selling Popsicles & Flipping Craigslist Finds 09:28 – Construction Work and Almost Dying 11:49 – The Walk That Changed Everything 16:33 – Ernest Shackleton, Antarctica & the Scrappy Mindset 21:17 – Working with Google, Nike & Founders Who Can't Sell 23:03 – Context Selling Explained 28:50 – Starting the Company & Getting Hit by COVID 33:02 – The Mexico Beach Reset 36:26 – High School Stephen & Boarding School 41:43 – Coaching Sales Teams & Measuring Success 44:21 – Lightning Round 52:24 – Where to Find Stephen Steers Connect with Stephen Steers: https://www.stephensteers.com/podcast https://www.linkedin.com/in/stephen-steers/ Connect with Jack Tompkins: LinkedIn: https://www.linkedin.com/in/jack-tompkins/ Company: https://www.pineapplecf.com Speaking: https://www.pineapplejacktompkins.com/