The Art of Success: Secrets to Discipline and Continuous Improvement

In this episode of the Legacy Podcast, host Paul Dio sits down with Gary Specter, CEO of Simpro, to discuss the importance of discipline and continuous improvement for entrepreneurs. Gary shares his journey as an entrepreneur and how his passion for fitness and car culture has shaped his mindset. He emphasizes the value of daily improvement and perseverance, highlighting that success comes from staying committed and dedicated to learning and growing. Gary’s insights into his entrepreneurial journey and the growth of Simpro provide valuable inspiration for entrepreneurs in search of valuable insights and motivation.

Whether you’re looking to achieve greater success in your business or personal life, this episode is packed with valuable advice and lessons from a seasoned entrepreneur. Tune in and discover how discipline and continuous improvement can lead to a lasting legacy.


Topics covered in this Episode:

  • The importance of discipline in entrepreneurship and how it can drive you towards greater success and achievement.
  • Learn from real-life career turning points and growth stories to navigate your own path and make informed decisions.
  • Harness the potential of your online presence to expand your business globally and tap into new markets and opportunities.


Connect with Gary here:


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About Gary:

Gary Specter leads the Simpro team as Chief Executive Officer. With more than 30 years of experience, Gary has a strong track record of scaling customer-focused organizations like Simpro. Prior to joining Simpro, Gary held senior leadership positions with, Adobe, Magento, NetSuite, and IBM. 


Timestamped summary of this episode:

00:00:00 – Introduction
The host welcomes Gary Specter, CEO of Simpro, as the guest.

00:01:23 – Overview of Simpro
Gary explains that Simpro consists of three portfolio companies: Simpro, a field service management application for various industries; AroFlo, a field service management company targeting a different audience; and Clockshark, a time card management application.

00:04:25 – Gary’s Background and Passion for Cars
Gary shares his background, growing up in Albuquerque and his journey from being a kickboxer and bodybuilder to transitioning to the business world and eventually technology. He also mentions his love for sports cars and his newfound passion for building Lego car kits during COVID.

00:05:54 – Valuable Lesson Learned
Gary’s most valuable lesson is to “get better every day.” He emphasizes the importance of continuous improvement and dedication to daily practice in order to achieve success in any endeavor.

00:07:17 – Key Decisions in Gary’s Life
Gary highlights two key decisions that significantly impacted his life. The first was transitioning from bodybuilding to pursuing a college education and a real career. The second was moving to Silicon Valley to pursue a job in technology, despite having no prior experience in the field.

00:15:19 – Introduction and Where to Find More Information
Gary Specter discusses where to find more information about him and his company, Simpro. He mentions that their website,, is a good resource and that they also have a blog. Additionally, they are active on social media platforms such as Facebook and LinkedIn.

00:15:33 – Global Business Growth and Social Media
Gary talks about Simpro’s efforts to drive and grow their business globally. He emphasizes their active presence on social media, including Facebook and LinkedIn, as part of their strategy.

00:15:48 – Thanking Aaron
Paul thanks Gary and expresses his appreciation to Aaron for their conversation on The Legacy Podcast.

00:16:02 – Call to Action and Review Request
Paul requests listeners to leave a review for the podcast on any platform they use. He also provides the website for more information about the podcast and its hosts.

00:16:17 – Conclusion

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