Elevator No. 200: Keegan O'Connor is the co-founder and CEO of Chill Shark, an innovative company transforming bathtubs into cold plunges to make cold water therapy more accessible. With a passion for mental health and a mission to help those struggling with PTSD, Keegan’s journey is fueled by personal experiences, resilience, and a drive to build something meaningful.

Chillshark went live on Kickstarter on March 18 and is now fully launched to the public.

In this episode, Keegan shares the challenges of launching a product, the importance of team dynamics, and how vulnerability plays a role in both business and personal growth. From the science of cold plunging to the power of storytelling, this conversation dives deep into entrepreneurship, wellness, and the mental fortitude required to create lasting impact.

Parker and Sam dive into the reality of uncertainty in entrepreneurship, personal growth, and success. No one really knows what they’re doing, but that’s where the magic happens. They explore how learning by doing, taking small bets, and seeking mentorship can turn uncertainty into an advantage.

Elevator No. 199: Michael Bluestone is the Founder & CEO of Bluestone Travel, an Independent Travel Advisor at FROSCH (a CHASE Company), and a member of the Chase Travel Group Advisory Board, representing 600+ travel advisors nationwide. Before launching Bluestone Travel, he spent his 20s leading luxury adventure trips across 70+ countries, curating unforgettable experiences in destinations like Patagonia, the Dolomites, and South Africa.

In this episode, Michael shares how travel builds resilience, shifts perspectives, and fosters personal growth. From navigating unfamiliar cultures to designing one-of-a-kind itineraries, he reflects on the lessons learned from a life spent exploring the world.

Society loves success but shames effort—why? Parker and Sam break down the weird stigma around trying hard, why it’s actually a superpower, and how putting in the work leads to authenticity, growth, and real success. They also highlight Brett Dashevsky, an elevator, who’s proving that effort is cool again.

00:00
Feedback on New Podcast Structure

01:48
The Hot Take: Trying Too Hard is Cool

06:00
The Difference Between Hard Work in Careers vs. Social Skills

10:13
Personal Experiences Shaping Perspectives on Effort

13:31
Elevator Shoutout: Brett Dashevsky Mentality

Elevator No. 198: Shirah Benarde is the co-founder and CEO of NightCap, a Forbes 30 Under 30 entrepreneur, and a Shark Tank-backed founder. She created NightCap—a drink spiking prevention company—at just 16, after learning how easily unattended drinks could be spiked. Her first prototype, made from a scrunchie and her mom’s stockings, turned into a globally recognized product that has sold over 700,000 units in 40+ countries, partnered with 160 universities, and is helping push for stronger drink safety laws.

In this episode, Shirah shares how taking risks, embracing discomfort, and leveraging social media helped her turn an idea into a global movement.

00:00
Navigating Family Dynamics in Business

07:11
The Journey of Entrepreneurship from a Young Age

12:45
The Decision to Drop Out of College

15:36
Understanding the Red Zone and Its Impact

18:49
Leveraging TikTok for Awareness and Growth

23:05
Personal Growth and the Challenges of Young Adulthood

29:03
Memorable Moments from Shark Tank

36:33
Mental Motto: Embracing Discomfort for Growth

Some days are smooth—until they’re not. Parker and Sam break down how they handle challenges that come out of nowhere.

Elevator shoutouts: Founder of LTM Laura Ter Meer and NHL creator and journalist Jonny Lazarus

Elevator No. 196: Lucy Nelles is a community-building expert, co-founder of Coffee & Chill Miami and the Community Building Collective. She’s hosted over 15,000 guests, generated over $500K in revenue, and built spaces where real connections thrive.

In this episode, Lucy shares her journey from a 9-to-5 to entrepreneurship, the mindset shifts needed to take the leap, the power of intentional networking, and how to create great events, navigate community dynamics, and embrace discomfort for growth.

03:08
Creating Unique Experiences in Miami

06:10
The Importance of Connection and Networking

09:12
The Leap of Faith: Quitting the 9 to 5

15:14
Designing Memorable Events

18:09
Handling Community Dynamics

20:47
Mindset and Overcoming Challenges

23:58
The Role of Co-Founders in Entrepreneurship

27:01
Rapid Fire

30:00
Lucy's Mental Motto

Parker and Sam are throwing down in a LinkedIn showdown—who can grow faster? They celebrate podcast milestones, share storytelling secrets, and break down why content creation takes mental fortitude.

00:00
Celebrating Milestones and Future Goals

02:59
LinkedIn Competition: A New Challenge

06:10
The Art of Storytelling and Content Creation

09:07
Engaging with the Community and Sharing Wisdom

11:47
Elevator Shoutouts and Community Events