HeyJaredHigh Stakes With Steve Rozenberg
Steve Rozenberg sits down with top entrepreneurs, industry experts, and high-level thinkers to uncover what really drives business success. From growth strategies to leadership insights, every episode delivers real-world advice you can apply immediately.
- Indexed episodes, last 90 days
- 12
- Latest publication
- Sep 23, 2026
- Audience
- Checking…
- Earliest in this view
- Jul 8, 2026
Latest episodes
Chasing Money Means You Die Empty with Felipe Freig (opens the original)
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Recorded live at JobTread Connect, this episode features Felipe Freig, owner of a luxury custom home building company in Vancouver, British Columbia, and a business coach for builders and trades across the U.S. and Canada. Felipe's path here is anything but typical. He immigrated to Canada at 12 years old, became a national-level gymnast, later landed a record deal and toured with major U.S. rock bands as a musician, and eventually built a construction company that's now doing $15 million a year
Why This Founder Believes Most People Should Not Become Entrepreneurs with J. W. Mason (opens the original)
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On this episode of High Stakes with Steve Rozenberg, Steve talks with Jackson Wyne Mason, owner of a construction company and founder of Crew Glue, a business built to help contractors estimate faster and more consistently. Jack's path started as a young employee at a general contracting company in Minnesota, where he was surprised by how chaotic the day-to-day operations really were. Instead of walking away, he leaned in, leaving that job to work as a carpenter for one of the GC's subcontractor
From Cold-Calling Strangers to Building a $100M Sales Engine with Nick Peret (opens the original)
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On this episode of High Stakes with Steve Rozenberg, Steve sits down with Nick Peret, founder of Better Boss, a JobTread-certified implementation partner that builds operating systems for contractors and wraps them in AI. Nick grew up in a family full of tradesmen but took a different path himself, working in product development at Milwaukee Tool before landing a cold-calling sales job that eventually pushed him to strike out on his own. His first six months as an entrepreneur produced zero reve
Running a Construction Business in One of the Most Remote Places in America with Jason Novotny (opens the original)
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Jason didn't set out to build a construction company in one of the most remote regions of the country. He and his wife took a vacation to Alaska in 2015, ended up on an impulse land purchase after driving up a random road outside Anchorage, and two years later relocated for good. Island Construction launched in June 2019, and Jason has been building both residential and commercial projects there ever since.The conversation digs into what makes running a contracting business in Alaska fundamental
Fired Repeatedly, Then Built 3 Companies From Zero to $4M+ with Brian Samson (opens the original)
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On this episode of High Stakes with Steve Rozenberg, Steve sits down with Brian Samson, founder of Plugg, a company connecting Latin American tech talent (software developers, DevOps, AI and data engineers) with U.S. companies. Brian didn't grow up wanting to be an entrepreneur. He spent a decade as a W-2 employee getting fired repeatedly for being too independent, before eventually building three companies that grew from zero to over $4 million in ARR. Brian and Steve dig into the near-shore st
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