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Building While Flying

Apr 15, 2021

Entrepreneurship looks different for everyone, and the definition often changes throughout your career and life—and that’s okay. Everyone is entrepreneurial to a degree, and embracing that entrepreneurial spirit will only open unimaginable doors. 

Welcome to Building While Flying!

This weekly podcast is brought to you by the Sasha Group. We’re the small-to-medium-sized business arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding, media, and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together. 

Jon Troutman and Nate Scherotter’s entrepreneurial paths have been anything but ordinary. 

As two VaynerX OGs, they’ve worked with Gary in many different ways—from Wine Library to Office of the CEO to most recently, Empathy Wines. Now they’re both VPs at Constellation Brands, a Fortune 500 wine, beer, and spirits portfolio company which bought Empathy Wines in 2020. 

In their conversation with Mickey, Jon and Nate break down each step of their careers, from getting in the door at VaynerMedia in the early 2010s, to founding Empathy Wines, a direct-to-consumer wine brand with Gary (in 2019), to joining Constellation Brands last year. They define what entrepreneurship means for themselves; dive into the mindset shift from working for an entrepreneur (like Gary) to being one yourself; share how Empathy Wines is making waves in a traditionally wholesale-based industry; the advantages of a one-to-one customer-brand relationship; and much more.

Other in-flight topics:

  • How Jon and Nate both landed in the wine world (and working for Gary)
  • How entrepreneurship varies from person to person
  • Entrepreneurship vs. Intrapreneurship 
  • The mindset shift from working for an entrepreneur to being one
  • The origin story of Empathy Wines.
  • Standing out as DTC in a wholesale-based industry


Follow Jon on Instagram @trouty -

Follow Nate on Instagram @nscherot -