Keynote and Fireside Chat with Chris Fenster

Join us at the January TIA Incubator for a keynote and fireside chat with Chris Fenster.

Fenster is an entrepreneur and financial strategist recognized for his deep expertise in guiding early-stage companies through complex growth phases. His entrepreneurial journey began in 1992 when he left a traditional consulting career to take a hands-on role in a small bike shop. Alongside a business partner, he transformed the local shop into “Start to Finish,” which grew into one of the largest independent bicycle dealerships in the U.S. before being successfully acquired by Trek Bicycle Corp. This early venture provided him with a foundational education in the high-stakes, “sink-or-swim” realities of business building, characterized by both significant successes and steep learning curves.

Following his success in retail, Fenster spent more than a decade as a full-time CFO for various early-stage companies, including an apparel manufacturer and a beverage company. This period was pivotal, as he navigated the challenges of diverse business models and learned essential lessons about company scaling and financial management. Having experienced firsthand both the success and failure of his employers, he developed a keen ability for pattern recognition. He realized that the traditional, fragmented approach to finance in startups was often inefficient, leading to unnecessary risk and operational blind spots for founders who were already overwhelmed by the demands of rapid growth.

In 2008, Fenster leveraged this insight to found Propeller Industries, a company designed to provide “enterprise-grade” financial horsepower to emerging businesses. By building a team specifically to deliver integrated finance, accounting, and strategic consulting services, he created a model that decoupled financial expertise from physical proximity and leveraged cloud-based technology to scale. Under his leadership as founder and executive chairman, Propeller Industries has grown into a global powerhouse, serving over 1,000 companies—including many high-growth unicorns—and employing hundreds of professionals. Through Propeller, Fenster has solidified his reputation as a mentor to the startup ecosystem, helping founders translate complex financial data into actionable growth strategies.

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We will have a catered lunch from noon to 1 p.m. and attendees are invited to that as well.