Lessons in Leadership: Mac Macleod’s Entrepreneurial Journey – Outside Insights Podcast Episode #44

by placers on April 12, 2024 in Outside Insights




In this week’s episode of Outside Insights, I was joined by Mac Macleod, the co-founder of Carvertise, a successful media company revolutionizing ride-share advertising. Mac and I go way back to the start up days of Carvertise as I worked closely with his co-founder, and previous podcast guest, Greg in local not- for-profit work with Junior Achievement of Delaware. Over the years, Mac and I have always scheduled time to talk business and share ideas and concepts that have helped us at key reflection points in our lives. We have been in MasterMind Leader groups together, shared the stage at entrepreneurial events, even done other podcasts together. I’m honored to now have Mac as a guest on the Outside Insights Podcast.


A summary of our discussion can be found below, but I encourage you to listen to the podcast episode here during your next commute!


Founded in 2012, Carvertise has become a big player in the advertising industry by leveraging ride-share vehicles for advertising. Major brands, like Netflix and 7-Eleven, partner with Carvertise to strategically place ads on Uber and Lyft cars to boost brand visibility. Even if you’re not familiar with the Carvertise name, you’ve definitely seen these advertisements if you’re cruising around major cities.


Mac’s Entrepreneurial Journey


Mac and I took a deep dive into discussing the trials, successes, and personal and professional growth that comes with entrepreneurship. During our discussion, Mac stressed the importance of enjoying the entrepreneurial process, despite inevitable challenges. Mac talks about the excitement and “adrenaline” of the early startup days when everything feels possible. Like many young entrepreneurs, he used to want to “conquer” every day but now focuses on chipping away consistently.


A significant part of the discussion revolved around how leadership styles must evolve as a company grows. Mac reflected on the shift from being hands-on and leading by example in the early stages, to adopting a more strategic and supportive role as Carvertise expanded. Effective leadership, according to Mac, now involves empowering a skilled team to drive the company’s vision forward, making adjustments as necessary to navigate the unpredictable landscape of business.


Finding Balance and Personal Growth


In true Outside Insights fashion, Mac and I discussed how to maintain a balance between the demands of entrepreneurship and the other facets of life. We share a similar approach to finding this balance, as Matt makes time for activities that recharge him, such as Brazilian jiu-jitsu, which helps him stay present and engaged. This practice of self-care and mindfulness is crucial for sustaining the energy and creativity needed to tackle daily business challenges. You can’t show up for others if you don’t show up for yourself.


Mac’s journey with Carvertise illustrates the multifaceted nature of entrepreneurship, from the excitement of starting up to the complexities of scaling a business. His insights serve as valuable lessons for aspiring entrepreneurs, highlighting the need for resilience, adaptability, and a clear sense of purpose.


Until next time, friends.



Mac’s Book Recommendations:

Gauguin: His Life & Works in 500 Images

The Sea & Civilization: A Maritime History of the World


If you found this conversation with Mac Macleod 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:

Community Spotlight: Empowerment Through Connection – A Sit Down WIth Cierra Hall-Hipkins – Outside Insights Podcast Episode #43

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

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

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