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Season 1, Episode 29

How to Survive the Start-up Rollercoaster as an Entrepreneur, Founder, and CEO with Terry Lee

About this episode:

The startup game is a roller coaster, and for many, it is one of the most difficult, frightening, stressful roller coasters in the world – it’s boot camp for the soul. As a founder, an executive, or a leader in a fast-growing company, you can feel alone in your struggles. We often hide them in an effort to appear like everything is going great. If you’re feeling alone in your role in the world as a leader, you can find healing in connecting with the stories of others.

Hear about the journey of startup entrepreneurship and how to navigate the rollercoaster of the startup game in this special guest episode of Allowed. Throughout this episode, featuring the remarkable Terry Lee, of Mezcal Rosaluna and MeUndies, gain insight and information about the leader’s journey and lessons that every conscious leader can learn from. He’s a former CEO, he’s a former COO, and he is human, just like you. Many of the lessons Terry learned along the way would not have come without a certain degree of heartbreak, pain, and struggle. The journey is ALWAYS here to teach us what our soul most wants to learn. Buckle up and come along for the ride as we dive into the wild rollercoaster of the startup game.



Read more about surviving a startup

Surviving the rollercoaster ride of startups requires a shift in mindset. Instead of striving for control, embrace striding and let things come naturally. Give yourself grace and kindness amidst the chaos. Feel your emotions fully and learn from them. Remember, there’s no winning or losing in startups; the goal is to stay in the game, learn, and adapt. It’s an infinite game of lessons and growth.

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We are in a time of deep change – a kind of change that requires not just incremental shifts, but deep transformation where we don’t know what the end state is going to look like, both collectively, but also for each of us individually. It’s changing the way that we need to show up as leaders and highlighting the importance of leading as whole humans with empathy and compassion for one another. Jeremi Gorman, the Chief Business Officer at Snap Inc, is here to discuss the importance of practicing and leading with empathy. Jeremi leads global sales, agency partnerships, customer and business operations, platform integrity, trust and safety, and creative strategy, and is also a huge influence on people’s mindsets and the culture at Snap, and she brings some great insight into leadership, from both a corporate and a personal standpoint. Company values come from the top, and leaders who practice empathy are leaders that teams are eager to support, teams that are willing and able to pivot, teams that want to learn and to grow, not just professionally but personally, and teams that stand together during times of crisis. 

Meet the Guest

Photo Guest Terry S1E29 How to Survive the Startup Rollercoaster as an Entrepreneur, Founder and CEO with Terry Lee 20200526

Terry Lee is the Co-Founder of Mezcal Rosaluna. Previously, he was COO at MeUndies

He graduated from the University of Notre Dame in 2009 where he played soccer and studied to become a sports orthopedic surgeon before changing his career path completely and taking on sales and marketing at Johnson & Johnson. 

After 3 years with J&J he took on an unpaid internship at a startup called CoachUp that had just launched. This role soon became a leadership role and not long after, his career skyrocketed when he connected with Dan King, who was their Head of Marketing at MeUndies. 

They arranged a 3-month consulting agreement, which ultimately turned into a 3-year stint as the COO. The all-star start-up team grew the company from a couple hundred thousand dollars per month to $35mm+ by the end of 2016.


  • 2:50 – Meet Terry Lee. Hear how Caneel and Terry Lee met and how he became an executive coaching client.
  • 7:09 – Terry Lee speaks about how being involved in soccer throughout college and his commitment to that with a singular goal helped train him for his entrepreneurship journey. 
  • 10:21 – Terry discusses striving and the idea that nothing is ever enough. Hear why striving is not the same as success.
  • 13:53 – Striving vs striding will determine your feeling of success. Terry Lee discusses the moment in his journey when he began to switch mentalities to a striding-focused growth mindset. 
  • 17:24 – Terry used the Change Formula unconsciously because he hit a certain level of discomfort in his business that forced him to make changes. 
  • 19:08 – Terry Lee discusses having grace for yourself and why grace is an impactful message for leaders.
  • 22:03 – Caneel and Terry Lee discuss the Drama Triangle and how Terry was putting himself into a Villain role.
  • 24:40 – Advice for current or aspiring COOs.
  • 28:56 – The biggest difference between being COO and being the founder CEO. 
  • 33:28 – Advice for founders about how to build a team of champions.
  • 37:00 – How to confront the dark nights of the soul.

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