Toronto Entrepreneur Shares Story of Startup Growth

In Crown Heights, a growing number of young people are entering entrepreneurship, though many lack clear guidance for the journey. The KFactor Podcast, produced by CHYE (Crown Heights Young Entrepreneurs) and COLlive.com, aims to address that gap.

In episode five, Izzy Rosensweig, founder of Portless, discusses his entrepreneurial path and how persistence, adaptability, and mentorship enabled him to build and reshape multiple ventures over more than a decade. His journey began with an early e-commerce venture - a Canadian daily-deal business that grew from a modest start into a multimillion-dollar operation. The business later transformed into a marketplace model that expanded internationally.

When digital advertising shifts created significant disruption, Rosensweig and his team repositioned their efforts toward Portless, a B2B logistics and fulfillment platform meant to help brands scale more efficiently.

"The biggest lesson I've learned is that your first plan is rarely your final plan," Rosensweig said. "You have to be willing to adapt, keep learning, and build with the long term in mind."

The platform was developed to help brands manage inventory and cash flow challenges through a more flexible supply chain approach, supporting companies navigating a competitive e-commerce market.

Rosensweig attributes his success to persistence, hiring decisions, and guidance from mentors, noting that strong companies rest on vision paired with the capacity to learn from difficulties and make deliberate choices about expansion. His experience speaks to local business communities and entrepreneurs building companies from inception.

Season three of the podcast is supported in part by Ainsworth Gorkin Law, which provides legal services to small and mid-sized businesses across New York and New Jersey.

For CHYE, the podcast represents part of a broader effort to build a community where young people feel supported and equipped to succeed as entrepreneurs.