In this episode, I was lucky enough to interview Jason Shafton, CEO and founder of Winston Francois.
Jason shares his journey from growing up in a family of entrepreneurs in Chicago to becoming a growth and marketing consultant for tech startups. Inspired by his parents’ business ventures in high-end audio equipment, Jason developed an early passion for business, launching a small airplane-selling stand as a child and later a record label in high school. His career took him from Google to leadership roles at Comedy Central, Headspace, and various startups before organically transitioning into consulting. What began as informal advising soon turned into a full-time business as demand for his expertise grew, leading him to establish Winston Francois—a firm offering fractional CMO and growth leadership services.
Jason explains how Winston Francois differentiates itself in the crowded world of growth consulting by leveraging deep operational experience in venture-backed startups and major tech firms. His first paying client, Modern Animal, exemplifies this approach, as he helped scale the tech-first veterinary service while continuing to work with them over time. Reflecting on his journey, Jason emphasizes the importance of defining an ideal customer early on, a lesson learned through trial and error. While his personal brand currently drives much of Winston Francois’ visibility, he hopes the company’s reputation will grow independently.
Take a seat and listen to Jason Shafton's story which highlights the power of relationships, strategic positioning, and staying adaptable in an evolving market in this episode of The First Customer!
Guest Info:
Winston Francois
winstonfrancois.com or wf.team/pod
Jason Shafton's LinkedIn
https://www.linkedin.com/in/jasonshafton/
Connect with Jay on LinkedIn
https://www.linkedin.com/in/jayaigner/
The First Customer Youtube Channel
https://www.youtube.com/@thefirstcustomerpodcast
The First Customer podcast website
https://www.firstcustomerpodcast.com
Follow The First Customer on LinkedIn
http://www.linkedin.com/company/the-first-customer-podcast/
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