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/

Support The Show

If Jack's story resonated with you, please:

• Rate and review on Apple Podcasts
• Share this episode with another entrepreneur who needs encouragement
• Subscribe so you never miss an episode!

In this episode of No Suits Allowed, Connor speaks with Shawn Whalen of Whalen Exteriors. Shawn opens up about growing up in a generational roofing and exterior business, taking over just days before the pandemic hit, and breaking the seven-figure barrier after 39 years in the making.

Together, Connor and Shawn walk through the mindset shift from “hammer swinger” to CEO, the tough decision to niche down to roofing and exteriors, and the power of disciplined execution, where you’re learning what you don’t know, finding the right mentors, and then putting every new tool into action.

They dig into the highs and lows of entrepreneurship: the long grind of reinvesting profits rather than chasing flashy growth, the financial habits that kept the company afloat, and the systems that turned one-off jobs into a scalable operation. Shawn also shares how he learned to let go of control, trust his team, and balance relentless hustle with much-needed downtime, lessons that paid off when Whalen Exteriors vaulted past $13 million in revenue.

Whether you’re a seasoned business owner or just getting started, this episode offers unfiltered advice on patience, planning, and people-first leadership.

Timestamps

• Shawn’s Background and Taking Over the Family Business – 00:00
• Breaking the $1 Million Revenue Barrier – 08:45
• Niching Down to Roofing & Exteriors – 19:10
• Financial Discipline and Right-Sized Growth – 29:20
• Leadership, Delegation, and Avoiding Burnout – 40:35
  
  

Connect With Shawn

LinkedIn: https://www.linkedin.com/in/shawn-whalen-139990196/

Learn more about Whalen Exteriors: https://whalenexteriors.com/

Connect With Connor

Website: https://exec.partners/

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

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

Support The Show

If Shawn’s story resonated with you, please:

• Rate and review on Apple Podcasts
• Share this episode with another entrepreneur who needs encouragement
• Subscribe so you never miss an episode!

In this episode of No Suits Allowed: Real Talk with Real Executives, Connor sits down with Adam Keys, Head of Product at Job Nimbus, recorded live at a Job Nimbus event in Chicago. Adam shares his unconventional journey from serial entrepreneur to product leader, starting with his creative solution to the housing market crash – selling "No Soliciting" signs door-to-door with a craft vinyl cutter. He walks through building multiple businesses including a sign company and a 3D promotional sports packaging venture, before making the difficult decision to close his final startup after a $36,000 equipment failure.

Adam reveals how his entrepreneurial experience became his secret weapon in landing his role at Job Nimbus, where he's grown from managing one development team to leading 12 teams as Head of Product. He discusses Job Nimbus's bold shift to AI-first development teams, the "flight risk" hiring philosophy that seeks out entrepreneurial talent, and why enjoying your work is essential to making real impact. Connor and Adam explore the mindset shifts required at each phase of business growth, the art of killing roadblocks, and how entrepreneurial thinking translates into corporate innovation.

Timestamps

• Adam's Background and Role at Job Nimbus – 3:11
• Early Entrepreneurial Journey – No Soliciting Signs Business – 7:13
• Building Multiple Businesses – Signs and 3D Stadium Packaging – 12:38
• The Difficult Decision to Close His Startup – Equipment Failure and Partnership Challenges – 17:45
• Transition to Product Management and Landing at Job Nimbus – 19:10
• The "Flight Risk" Hiring Philosophy and Future Plans – 21:30

LinkedIn: https://www.linkedin.com/in/adamkeys/

Learn more about Job Nimbus: https://jobnimbus.me/3W53LGU

Connect With Connor

Website: https://exec.partners/

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

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

If Adam's story resonated with you, please:

• Rate and review on Apple Podcasts
• Share this episode with another entrepreneur who needs encouragement
• Subscribe so you never miss an episode!