Entrepreneurial Gems: A Chat with John Ratliff – Outside Insights Podcast Episode #42

by placers on February 16, 2024 in Outside Insights



In this insightful episode of the Outside Insights podcast, I sat down with John Ratliff, the entrepreneurial force behind Align 5 and CEO of Scaling Up Coaches.


During the episode, John and I discuss the multifaceted journey of entrepreneurship and the significance of mental health and creativity in the entrepreneurial realm.


I have known John for decades and admire his body of work, accomplishments and drive to impact the entrepreneurial landscape globally. John has been a top 100 wish list target for Outside Insights — goal accomplished!


Few have built a business from scratch, bootstrapped, built organically, grown by acquisition, exited successfully, been an investment banker, entrepreneurial coach, leader of coaches and all in all entrepreneurial advocate. Most importantly, John is a learner, loves new ideas and seems to always see the possibilities and bigger picture. I’m always feeling inspired by John.


Save this podcast for your next commute or workout to hear two serial entrepreneurs discuss:

  • The importance of recognizing and leveraging hidden assets within your business or any new venture.
  • The value of external perspectives in uncovering these “Rembrandts.”
  • The challenges of entrepreneurship, including the risk of isolation and mental health struggles.
  • The significance of creativity, curiosity, and continuous learning in navigating the fast-paced business landscape.
  • The need for a supportive community and the willingness to seek help and mentorship.

John Ratliff’s entrepreneurial voyage began with his call center business, which, despite initial hurdles, laid the foundation for his understanding of business dynamics and growth strategies. His involvement with Align 5 and Scaling Up Coaches underscores his commitment to nurturing middle-market companies and their leaders, emphasizing the critical role these entities play in the economy.


A pivotal theme John discusses is the concept of “Finding Your Rembrandt in the Attic.” This metaphor illustrates the often-overlooked assets within businesses that, when recognized and leveraged, can significantly enhance a company’s value. John stresses the importance of external perspectives in identifying these hidden treasures — someone to help you see what may have been right in front of you the whole time.


The conversation also touches on the solitary nature of entrepreneurship. John candidly shares the challenges and internal struggles many entrepreneurs face, including the risk of isolation, depression, and burnout. He advocates for a supportive community and the courage to seek help, emphasizing the importance of mental health awareness and self-care in the entrepreneurial journey.


John’s leadership philosophy is deeply ingrained in the principles of creativity and lifelong learning. In an era marked by rapid technological advancements and societal shifts, he believes that the ability to adapt and innovate is paramount for entrepreneurial success. His parting advice for entrepreneurs: Take moments to reflect on achievements and while remaining grounded in the fundamentals of business. Don’t get caught in the allure of rapid, often unsustainable, growth strategies.


I hope you find yourself as inspired as I am in guests like John — who have achieved their goals many times over through grit, resilience and a healthy amount of stubborness.


Thanks for listening, friends.



If you found this conversation with John Ratliff insightful and valuable, make sure to subscribe to Outside Insights, with the links below, for more enriching discussions on entrepreneurship, creativity, and mental health. Join our community of entrepreneurs and thought leaders, and let’s grow together! You can subscribe to the podcast wherever you find your podcasts and on YouTube.

If you enjoyed this, I recommend listening to these past Outside Insights Podcast episodes:

Leveraging Tech for Social Good – A Sit Down With Pat Callihan – Outside Insights Podcast Episode #41

Finding Success Off the Corporate Ladder – A Sit Down WIth Chris Bystriansky – Outside Insights Podcast Episode #40

A Misfit Thanksgiving – Outside Insights Podcast Episode #39.

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