Reading Time: 3 minutes
Reading Time: 3 minutes

From Pony Grooming to Agency Building – The Grit and Drive of Amy Winner

Amy Winner, Co-Founder & Head of Strategy and Development of Wheels Up Collective shares her inspiring journey from starting a pony grooming business at a young age to building a thriving boutique marketing agency. She discusses the importance of perseverance and hiring former athletes, while also sharing the story behind the formation of Wheels Up Collective. Amy highlights the significance of networking, referrals, and building strong relationships in the B2B marketing industry. Additionally, she explores the impact of having a tight marketing budget and the shift toward measurable impact. Amy also emphasizes the power of creating a virtual work environment with flexible hours, promoting mental health, and utilizing user-generated content for community building. Overall, this episode offers valuable insights for success in the marketing industry.

Here are a few of the topics we’ll discuss on this episode of Masters in Marketing Agency Podcast.

  • Wheels Up Collective was born during the COVID-19 pandemic, with a focus on helping companies transition to a digital-forward strategy.
  • Lean budgets force marketers to be more prescriptive and strategic.
  • Rigor and accountability are necessary to avoid wasting money.
  • Foster strong relationships through one-on-one interactions and build trust with your team members.
  • Incorporate user-generated content to expand the reach of your community and share success stories.
  • Focus on your strengths and partner with other agencies to provide a comprehensive service.
  • Stay connected with clients even when referring business to others to maintain a strong network.


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  • 00:47 – Well, you know, like every little girl when she’s four or five wants a pony. And I was one of the brats who got one. I have horses in my blood. It’s what keeps me working. So I can play at the barn, but yeah, I started grooming my own horses when I was young because I was a barn rat and wanted to do it myself. And, you know my parents said, if you wanna do this sport, it’s expensive, you gotta figure out how to pay for it. And so I started hustling the other people at the barn and doing some work for them and built up quite the clientele base and ultimately ended up making enough money to put a down payment on my first house when I was, I think 25. So it was quite lucrative.
  • 7:10 – Nobody really knew what Zoom was or the general public didn’t know what Zoom was before the pandemic. So there was just this huge gap of talent out there to help companies adopt a more digital forward footprint or strategy. We actually had people reaching out to us that colleagues from Seattle saying, “Hey, can you help with this? Can you help with this?” And the next thing you know we got the gang back together.
  • 28:54 – It’s so addictive. Which one of us wouldn’t admit that like at two o’clock in the morning we’re scrolling doom scrolling through like TikTok because the algorithm has it figured out, you know? I think especially in industries where you wouldn’t think TikTok would be a hit. Like we’ve had clients use it and it’s a small slice, it’s a small slice of people, but if you reach the right people, it’s not that expensive to do. We actually have a TikTok celebrity on the Wheels Up team. She’s like an accidental TikTok celebrity. She ended up like a million followers without trying.
  • 33:23 – I think you need to know what you’re good at. I think like, especially in the early days, it’s really easy to want to get like any business that you can, and I get it like you just need to get revenue through the door, but the wrong fit is gonna slow you down and it’s gonna waste your time and it’s gonna, you know, it’s the opportunity cost of the, of the jobs that you missed and the opportunity cost of time that you didn’t spend pitching and building the right relationships.
  • 34:32 – When I think about engagements that didn’t work well, that’s usually what happened. The expectation setting was not appropriate. You know, we didn’t do a good enough job setting expectations and saying, no, we don’t want this work when they pushed back or they were a little too early stage. So I would say know exactly who you are, sit down, write it down, write your messaging and positioning. It’s so hard to do. It’s so hard to do, but it’s so hard to walk away from business.