Selling Pagers in a Crack Epidemic and Other Scrappy Sales Stories with Sean McColl
- Jack Tompkins
- Aug 2
- 4 min read
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 pagers in Washington, DC during the crack epidemic, building accounts at AT&T, and growing a promotional products company from a tiny startup to a successful acquisition - he went independent as an outside advisor. Today he works with owners, successors, and key leaders to bring the objectivity that insiders can't generate on their own, helping businesses find their blind spots and build sustainable growth.
In this episode, Sean takes us from early childhood hustles - cutting lawns at 11, running a babysitting operation with his sister as a two-for-one package deal, and getting his first real taste of workplace standards as a 14-year-old dishwasher - all the way through decades of high-stakes sales leadership and into what it really means to be a business therapist who helps CEOs sleep better at night. He shares why the very traits that make great entrepreneurs successful are often what hold them back as they scale, how the Who Not How principle shows up in his daily advisory work, and why outside perspective is the most undervalued asset any growing business can have.
The Scrappy Sales Origins of a Future Business Advisor
Sean grew up outside Boston in a family where getting things done was simply a way of life. His mother ran a family placement business before the internet existed - with an almost psychic ability to read people and match them to the right family. His father built the pottery kiln from scratch. Sean carried that into his own early hustles: cutting lawns at 11, running a babysitting operation with his sister as an unbeatable two-for-one package (one call, two potential sitters for Saturday night), and writing a college essay about getting corrected by a kitchen cook as a 14-year-old dishwasher. The lesson from that cook - do you wash behind your ears at home? - became a formative reminder that the real world holds you to a higher standard than the neighborhood lawn.
Selling Pagers in DC During the Crack Epidemic
Sean's first post-college job put him selling pagers in Washington, DC at the height of the crack epidemic - a territory no one else wanted. By the time he left, he had turned it into the company's most successful territory. His strategy was partly accidental and partly brilliant: because nobody could figure out why a guy in a suit driving an old dented Buick would be in those parts of town, they assumed he was a cop. He leaned into it - aviator sunglasses, briefcase, the largest pager model clipped to his belt like a prop - and built his book of business. The lesson stuck permanently. After walking into those neighborhoods every day, every boardroom felt low-stakes by comparison. As Sean put it: what is the worst that can happen? They ask you to leave. At least you do not have to worry about getting shot.
Why Great Owners Are Often Their Own Biggest Obstacle
After decades in sales leadership and growing a promotional products company from a tiny startup to an acquisition (it is now a $200M company), Sean launched Trusted Business Advisors about four years ago. His core observation: the same traits that make entrepreneurs great - attention to detail, getting involved in everything, refusing to let things fall through the cracks - become the ceiling when it is time to scale. There are only so many hours in a day, and someone who built a business by doing everything themselves will eventually hit that wall. Sean's approach is not to hand clients a playbook but to ask good questions, reflect back what he is hearing, and let them find their own clarity. By the time he has finished restating a situation back to a client, they usually already know what needs to happen. They just needed someone they could talk to confidentially - someone whose job it is to think about their business even when they are not in the room.
The Business Therapist Who Helps Owners Sleep Better at Night
Sean's daily work is a living example of the Who Not How principle. When a client needs a new accountant, he introduces two options and helps them think through which one fits their goals - rather than trying to handle the accounting himself. When a legal question surfaces, he flags it and connects them to the right specialist. He operates like a doctor who knows when to refer to a specialist, and his network of trusted contacts is part of the value he brings to every engagement. The business therapist label came from a client who used it to introduce Sean at a company event. Sean leaned into it and told the person he was being introduced to that he helps business owners sleep better at night. Her immediate response: you need to talk to our CEO. That phrase has opened more doors than any formal pitch - and it captures what his work actually is. A confidential sounding board. A trusted outside perspective. Someone in your corner who is constantly looking out for your business and asking the questions that people on the inside have stopped asking.
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[Guest links - Jack: please add Sean's LinkedIn and website here once the bio/links section in his prep doc is filled in]
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