Many skilled operators dream of being their own boss, but the reality is a brutal mix of financial pressure, operational chaos, and personal sacrifice. In this episode, Sy Kirby of Sy-Con Excavation shares his unfiltered story of turning a trade into a thriving business.

From a name his grandfather wrote on a toy truck to building a company, a popular YouTube channel, and the Blue Collar Business Podcast, Sy reveals the raw truths about making big bets on people, kickstarting a marketing strategy at CONEXPO, and handling the crushing stress of being the CEO.

🎯 KEY EPISODE TAKEAWAYS:

🤝 The Dozer Deal: How a Two-Year Promise Unlocked a New Division [06:45]

"'You come to work for me for two years... and I'll go buy you the baddest daggum dozer on the market when it comes time.' Sure enough, two years goes by and we've got a chance of capturing an entire project together."

Sy reveals how a long-term vision and a leap of faith in a key employee unlocked a new division for his company.

💀 Beyond the Big Iron: The Brutal Reality of Business Ownership [13:07]

"I can't tell you how many Thursdays we've sat there and prayed... 'How's tomorrow going to work out?' The gear is super cool to look at... but making sure your guys' payroll is there every Friday..."

Learn all about the immense emotional and financial pressure entrepreneurs face beyond the equipment.

🚀 The Accidental Viral Video: How 15 Seconds at CONEXPO Ignited His Marketing [21:48]

"It was just a simple 15-second short, went completely viral…It definitely helped gain some traction and help the algorithm base who we are."

Sy explains how one simple video jumpstarted his marketing effort, proving you don't need a perfect strategy to get results.

CHAPTERS:

00:00 - Starting Sy-Con and Honoring a Family Legacy

02:01 - Building a Business Around Better Work Culture

04:32 - From Residential Work to Commercial Contracts

05:46 - Expanding Into Dirt Operations and Team Growth

08:06 - Hard Lessons from Scaling and Equipment Investments

10:13 - Turning Small Jobs into Long-Term Opportunities

12:34 - Managing Growth, Stress, and Entrepreneurial Pressure

16:23 - Systemizing Operations and Building a Stronger Team

19:35 - Launching a Marketing Strategy with CONEXPO and YouTube

26:44 - Creating the Blue Collar Business Podcast

32:40 - Advocating for Trades Over Traditional College Paths

40:00 - Why AI Makes Blue Collar Careers More Valuable Than Ever

🔗 CONNECT WITH SY KIRBY:

YouTube: https://www.youtube.com/watch?v=yQQpxlyHHeY

Podcast: https://www.bluecollarbusinesspodcast.com/

LinkedIn: https://www.linkedin.com/in/sy-kirby-18395b2a6/

Website: https://www.syconexc.com/

Thank you to our good friends over at John Deere Power Systems for sponsoring this podcast: https://www.deere.ca/en/engines-and-drivetrain/

CONEXPO-CON/AGG Newsletter: https://www.CONEXPOconagg.com/industry-news#sign-up

#Excavation #Entrepreneurship #BlueCollarBusiness