Artwork for Winning On Main Street

Winning On Main Street - Small Business Podcast

Gordon Henry

Gain actionable insights each week on how to successfully run a small business in today’s competitive landscape. In each episode, Gordon Henry chats with small business owners, entrepreneurs, and industry experts about the challenges of starting a business and how to provide incredible client experiences. We focus on technology, especially cloud software, that small businesses can use to modernize and automate their businesses to become easier to do business with. We are passionate about helping small businesses grow, modernize, and thrive in today’s evolving environment. To learn more visit:


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Latest Episodes

The small business coaching and consulting space is quite crowded and it can be hard to stand out. However, that isn’t just limited to our industry but a lot of the small businesses we coach find themselves in a similar situation. Something we recomm... more

4 days ago

When you dig into the numbers about two out of three small businesses fail. Considering I have three kids at home that have an entrepreneurial spirit that means two of them might not ever move out of the house. There are a few common areas I coach pe... more

11 days ago

Jeffrey Feldberg increased the value of his business by 10x in 2-years before selling. Jeffrey shared, up to 90% of liquidity events fail, and most of the time they fail due to a lack of preparation. However, even for the remaining 10% of events that... more

18 days ago


5 out of 5 stars from 26 ratings
  • Are you a small biz owner? Hit the subscribe button! more

    4 months ago
  • Are you a small biz owner? Hit the subscribe button!

    If you’re looking for great conversation, inspiration, and ideas of how to level up your business - hit the subscribe button! This show is a wealth of valuable advice for small businesses. Each episode contains best practices and actionable tips to not only help you get by, but thrive. Highly recommend listening and subscribing!

    Apple Podcasts
    United States5 months ago
  • An Absolute Must Listen for Every SME Business Leader

    The Winning on Main Street podcast should be mandatory listening for all Business Owners and Leaders who are looking to build and growing thriving businesses. Every episode is full of practical and actionable insights and tips to help small business leaders raise the performance of their companies so that they are truly WINNING! more

    Apple Podcasts
    Loving the B2B
    Australia8 months ago
  • It’s worth the time.

    Each episode I listen to I learn something new. Whether it’s a new tip on how to do something or a different perspective on how to think of something it’s been worth my time to listen.

    Apple Podcasts
    Palatine Dad
    United States10 months ago
  • Great Podcast for Small Biz!

    Helpful tips and takeaways in each episode!

    Apple Podcasts
    United States10 months ago

Frequently Asked Questions About Winning On Main Street

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How much does it cost to sponsor Winning On Main Street?

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How many subscribers does Winning On Main Street have?

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How many listeners does Winning On Main Street get?

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How many episodes of Winning On Main Street are there?

Winning On Main Street launched 3 years ago and published 104 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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