Venture Best Spotlight Season Two Episode Five

 | Podcast Series

When Matt Howard co-founded EatStreet, online food ordering was still in its infancy—and restaurants were receiving orders via fax. Over the next decade, Matt led the company through explosive growth, a strategic acquisition, and a bold move to classify delivery drivers as employees—long before the rest of the gig economy caught on.  

In this episode, Venture Best Partner Melissa Turczyn reconnects with Matt to reflect on the highs and lows of his entrepreneurial journey. From navigating COVID-era surges to battling the IRS in a make-or-break legal fight, Matt shares what it really takes to lead a startup through uncertainty. Now a fractional CFO to early-stage companies, he’s helping founders tackle the same operational and financial challenges he once faced himself.  

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