Two powerhouse entrepreneurs sit down for a real, unfiltered rooftop conversation about business, lifestyle, and cigars. Get insights on entrepreneurship, tech, and global connections—straight from the source.

- The realities of entrepreneurship and balancing family life
- Why tech is essential in the evolving cigar industry
- The challenges—and workarounds—of marketing cigars online
- Reggie Kimble's unique experiences living and working in Saudi Arabia
- Exclusive behind-the-scenes on smokedog.com’s growth and global reach


00:00 Introduction
00:11 Collab Interview Setup
01:16 Entrepreneurship and Family Balance
02:30 Building Businesses and Freeing Up Time
03:55 Real Talk About Cigars
05:04 Cigar Fermentation and Resting
06:02 World Travels and Living Abroad
07:10 Tech Career, Mentorship, and Saudi Arabia
08:53 Lessons from 26 Years in Tech
10:32 Leaving Corporate for Passion
11:37 Bringing Tech to the Cigar Industry
12:45 Marketing Challenges in Cigars vs. Other Industries
14:30 Building Community & Business with SmokeDog.com
16:12 Global Expansion and Business Reach
17:41 Smoking with Saudi Royals
19:55 Navigating Cultural Differences and Code Switching
21:08 Mutual Respect and Show Hosting
22:57 The Future of SmokeDog.com
24:04 Closing Remarks and Connection Info

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