A great teacher can be the key to welcoming challenges, self-confidence, and a curious spirit. In the case of Larry Berlin, Chief Financial Officer at Freedom Fries, great teachers also inspired a lifelong commitment to mentorship, including his critical mentor role for the New Venture Challenge, an accelerator program that has launched Grubhub, Braintree/Venmo, and many more successful companies.

In this episode, Larry shares details of the development process and aims of his recent venture: search engine and news aggregator Freespoke.com. He outlines how to approach analyzing product-market fit and your company’s competitive grid. Bringing lessons from his experiences mentoring an array of startups, Larry discusses how to deal with surprises and highlights the “need-to-know” aspects of a pitch.   

• (01:13) – Freespoke.com
• (05:21) – The challenges of managing a startup
• (11:24) – Flexibility as an entrepreneur
• (14:21) – Product-market fit and building your competitive grid
• (21:31) – Encountering surprises
• (24:12) – Testing your assumptions
• (29:52) – New Venture Challenge
• (34:24) - Mentorship

Larry Berlin is the CFO of Freedom Fries (Freespoke.com), a mentor at the University of Chicago Booth School of Business, and leads Blue Point Advisory Services. Previously, he worked at First Analysis for nineteen years and earned an MBA from the University of Chicago Booth School of Business.  

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Podcast episode production by Dante32.