In this episode of No Suits Allowed: Real Talk with Real Executives, Connor sits down with Jack Cottrell, owner of Jack the Roofer, to explore his journey from working as a roofing installer in 1996 to building his own successful roofing company in the competitive Denver market. Jack shares his story of starting as a laborer who intended roofing to just pay the bills through college, transitioning into sales when his body couldn't keep up with the physical demands, and eventually learning that nothing comes naturally to him except hard work and persistence.

Throughout their conversation, Jack opens up about the challenges of an industry that attracts unscrupulous operators, his decision to start his own company after being repeatedly shortchanged by employers, and his core philosophy that putting customers first would ultimately lead to success. Connor and Jack discuss the evolution from a one-man operation where the owner's reputation carried the business to scaling with a sales team while maintaining the same high standards and values. They dive into practical challenges like expressing company vision through sales presentations, the importance of doing the right thing even when it costs money, and Jack's refreshingly honest perspective on dreaming big versus steady, deliberate growth.

Timestamps

• Jack's Early Career Journey – From Installer in Oregon to Sales in Colorado – 2:50
• The Reality of Physical Labor and Transitioning to Sales – 3:30
• Working for Other Companies and Learning What Not to Do – 6:45
• The Decision to Go Out on His Own – 8:20
• Building a Customer-First Philosophy and Finding What Sets Them Apart – 9:15
• Scaling Challenges: From Jack's Personal Brand to Company Brand – 18:30
• Expressing Company Values Through Sales Presentations – 19:45
• Final Advice: The Importance of Doing the Right Thing – 23:00

Connect With Jack

Website: https://www.jacktheroofer.com/

Phone: (720) 722-2255

LinkedIn: https://www.linkedin.com/in/jack-cottrell-86b55033

Connect With Connor

Website: https://exec.partners/

Instagram: https://www.instagram.com/connor.rodich/

LinkedIn: https://www.linkedin.com/in/connor-rodich/

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