Deal Flow Diaries
Deal Flow Diaries is a high-impact podcast offering listeners a rare window into the minds of the titans shaping today’s economy. From private equity and real estate to fashion, tech, and entertainment, Alexandra Fairweather and Elaine Chamberlain sit down with visionary founders, fund managers, and cultural leaders. Together, they reveal the untold stories behind big deals, hard setbacks, and bold bets—giving listeners unfiltered lessons in risk, ambition, and strategy.
Disclaimer: The views and opinions expressed by the guest(s) are their own and do not necessarily reflect those of the hosts or Deal Flow Diaries (or its affiliated companies). This podcast is for informational and entertainment purposes only and should not be construed as legal, tax, investment, medical, or other professional advice. You should consult your own advisors before making decisions based on this content.
Deal Flow Diaries
Sarah Nesheim: Startups, the Future of Content, and Smart Pivots
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In Episode 4 of Deal Flow Diaries, we sit down with Sarah Nesheim, co-founder of Crafted, to unpack the pivots, mistakes, and mindset shifts that transformed a pandemic side project into a data-driven platform connecting social media to real world retail sales.
Sarah’s journey did not begin with a polished product. It began with investing her life savings into a recipe-sharing app during lockdown, pivoting to live streaming commerce, and ultimately discovering the real problem brands were desperate to solve: how to prove that digital content actually drives in-store purchases.
Crafted now operates at the intersection of creators, paid media, and brick-and-mortar retail, using trackable campaigns and digital rebates to measure real checkout behavior, not vanity metrics. What started as influencer campaigns evolved into a platform built around measurable retail conversion, first-party data, and disciplined execution.
Join us as we talk about:
- Turning an ego-driven idea into a validated business by identifying and solving a real problem that customers will actually pay for
- Founder-led sales, running effective discovery calls, and the BANT framework for closing deals
- Preparing for VC pitches like a data-driven sales process, recording every call, and improving analytically
- The emotional swings of startup life, impostor syndrome, and developing unshakeable confidence over time
- Why unsexy businesses often win
- This episode is a reminder that real businesses are rarely built in a straight line. They are built through pivots, humility, discipline, and a willingness to abandon the wrong idea in pursuit of the right one.
- Deal Flow Diaries continues to take you inside the real decisions, inflection points, and mindset shifts behind founders who are building systems that compound.
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Recorded at The Newsstand Studios at Rockefeller Center.
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