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INspired INsider with Dr. Jeremy Weisz


INspiredINsider Show with Dr. Jeremy Weisz features interviews with successful entrepreneurs, Ecommerce founders, & visionary leaders.

Leaders reveal deeply personal stories and explore the tough journey, big challenges, and mistakes that they overcame to achieve success.

You will find inspiring stories from: Founders of Atari, Baby Einstein, P90X, Einstein Bagels, Skymall, and many more.


Thank you for listening from your host of http://InspiredInsider.com Dr. Jeremy Weisz. Go to InspiredInsider.com for Full Video episodes. 

May 11, 2018

Today we have Tom Montgomery, co-founder and Chief Marketing Officer of Chubbies Shorts. Chubbies is the most radical shorts company on the planet: an irreverent lifestyle brand focused on revolutionizing the shorts industry. The company revolves around a customer service-focused business model offering free three-day shipping, free returns, social advertising campaigns, and dedicated human customer service lines.

Here’s a glimpse of what you’ll learn:

  • [0:45] Tom Montgomery joins the podcast to talk about his company, Chubbies.
  • [4:00] What was the first version of Chubbies Shorts like?
  • [6:00] Tom talks about the creative process and surprising products that took off.
  • [8:00] How Tom and his team are innovating when it comes to social media engagement.
  • [9:45] Challenging moments in the business so far.
  • [12:00] Building a healthy team environment with good values and transparency.
  • [15:00] Lessons learned along the way.

In this episode…

When was the last time your company conducted an audit of its social media engagement strategy? Is your organization pushing the envelope and innovating on that front or are you simply doing what everyone else is doing? On this episode of Inspired Insider, you’ll hear from business leader and entrepreneur Tom Montgomery. In his conversation with Jeremy, Tom explains how Chubbies got started, what their creative process is like, how they lead the way with social media engagement, challenges they’ve faced along the way, why they place such an emphasis on team culture, and so much more! You don’t want to miss a minute of this fascinating episode featuring Tom!

Did you know that social media engagement should be fun? It’s true! At least that is what the perception should be. If you take a look at some of the top businesses that are excelling at social media engagement you’ll see that they are succeeding because they have fun with their content. What can your organization learn from the example that Tom Montgomery and his team at Chubbies have highlighted with their expert use of social media engagement? Find out by listening to this informative episode of Inspired Insider, you don't’ want to miss it!

What is the status of your team environment? Would you say that it’s healthy? What emphasis do you place on values and culture? On this episode of Inspired Insider, you’ll hear from entrepreneur and innovator Tom Montgomery. From the onset, Tom and his team have worked hard to maintain a thriving work environment at Chubbies. According to Tom, this robust environment is due to the level of empowerment and positivity that flows through the culture they’ve built. Learn more about Tom’s story and the amazing business they are building at Chubbies by listening to this engaging episode!

Resources Mentioned on this episode

Sponsor for this episode

The Internet Retailer Conference & Exhibition – better known as IRCE – is your one-stop-shop for all of your e-retail needs. This conference and trade show offers you everything your business needs to stay ahead of your competition, in one simple location. IRCE is right around the corner in Chicago so go to www.irce.com to find out more.

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Rise25 is where entrepreneurs of 6,7, and 8 figure businesses come together live and in person every few months to solve their biggest business challenges through this high-level Mastermind group. Each member leaves each week with lifelong friendships and actionable steps to take their business to the next level. Check out Rise25.com - a group run by myself and cofounder John Corcoran. Rise 25 is application only.