What actually separates the operator who doubles their business from the one who stays stuck?
Chris Thomson sits down with three of the most improved operators in the Student Works painting division, Jack Buiter, Ali Baksh, and Owen Chilvers, to unpack how they went from rough first years to breakout seasons. Each of them hit a wall early: inconsistency, fear of what people think, a big vision with no plan, and each found a way through.
They get into the mindset shifts, daily habits, and business strategies behind doubling a student-run business: keeping commitments to yourself, building an enrolled team, Facebook marketing, hiring the right people, and learning to charge what you are worth.
If you are coming back for another season and want to know exactly what it takes to step up instead of stalling out, this conversation is your roadmap. Listen now.
Timestamped Highlights
● 00:37 – Jack on the first year that handed him a brand new problem every single day
● 03:25 – Owen sells $20,000 on day one, then watches it all go downhill
● 06:14 – The $200K vision Ali set with no real plan to reach it
● 08:20 – The missing piece that stalled Jack’s first two months
● 15:07 – How Owen now does in 40 hours what used to take him 100
● 17:56 – The 0 for 12 start behind Ali’s flat second year
● 23:29 – Fear of other people’s opinion, and how Chris dismantles it
● 26:14 – The December 27 commitment Ali made to himself
● 36:17 – Why Chris says a painting business is really just math
● 37:46 – The marketing channel that became nearly half of Jack’s business
● 41:42 – Owen on the “secret sauce” that does not exist
About the Guests
Jack Buiter is a second-year operator with the Student Works Management Program, managing in Hamilton while completing a master’s at the University of Guelph. He did $194,000 and earned the Mexico trip in his first year and is tracking toward roughly $450,000 this season, driven by strong systems, an enrolled team, and Facebook marketing.
🔗LinkedIn
Ali Baksh is a third-year operator based in Durham and a student at Western University. After two roughly flat years around $105,000 to $107,000, he broke through in year three toward roughly $250,000, with his sights set on the million-dollar club next year.
🔗LinkedIn
Owen Chilvers is a second-year operator managing in Halifax while studying at Dalhousie University. He joined the program at 17, did $120,000 his first year, and has already sold around $250,000 this season while tracking toward roughly $350,000, powered by a relentless focus on mindset, integrity, and efficient marketing.
🔗 LinkedIn
Resources and Links Mentioned
● Facebook Ads (Meta)
● Indeed
● Jim Collins (“First Who, Then What”)
● Landmark
● Dan Kennedy (pricing principle)
● John Cameron (Facebook ads advisor)
Important Links
● Connect with Chris:Website |LinkedIn
● Learn more about theStudent Works Management Program
● Apply to be anOwner / Operator in the Management Program
● Looking for a fun job this summer?Summer Job Opportunities
● Hear more AlumniSuccess Stories
The Leaders of Tomorrow Podcast is an original production by Chris Thomson. Production and editing byPodcast Your Brand.
