KFactor Podcast: Toronto Entrepreneur Izzy Rosensweig shares his story of startup growth, reinvention, and building the logistics platform Portless. Full Story, Video
In Crown Heights, more young people than ever are stepping into the business world — but many are doing so without a clear roadmap.
The KFactor Podcast, an initiative of CHYE (Crown Heights Young Entrepreneurs) & COLlive.com was created to change that.
In episode #5 of The K Factor Podcast, Izzy Rosensweig, founder of Portless, shares the story behind his entrepreneurial journey, offering a look at how persistence, adaptability, and strong mentorship helped him build and reinvent multiple businesses over more than a decade. Rosensweig’s path began in the early days of e-commerce, when he launched a Canadian daily-deal business and grew it from a small operation into a multimillion-dollar company.
Over time, the business evolved into a larger marketplace model, eventually scaling across international markets. After facing major disruption from shifting digital advertising conditions, Rosensweig and his team pivoted again—this time building Portless, a B2B logistics and fulfillment platform designed to help brands grow more efficiently.
“The biggest lesson I’ve learned is that your first plan is rarely your final plan,” said Rosensweig. “You have to be willing to adapt, keep learning, and build with the long term in mind.”
Portless was created to help modern brands reduce the burden of inventory and cash flow pressure by using a more flexible supply chain model. Today, the company supports brands looking for a healthier way to scale in an increasingly competitive e-commerce environment.
Rosensweig credits much of his success to a combination of persistence, smart hiring, and advice from trusted mentors. He says the strongest businesses are built not just on vision, but on a willingness to stay grounded, learn from setbacks, and make thoughtful decisions about growth. His story will resonate with local business communities, entrepreneurs, and anyone interested in the realities of building a company from the ground up.
Season 3 is made possible in part by Ainsworth Gorkin Law, a legal services firm that works closely with small and mid-sized businesses across New York and New Jersey, helping them navigate legal challenges and build strong foundations.
For CHYE, the podcast is just one piece of a larger vision: creating a community where young people feel supported, equipped, and empowered to succeed.
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