Will My Dolly Fit?

In this episode, Damashe and Michael dive into a lively and personal conversation, packed with humor and insights from their day-to-day experiences.

Damashe kicks things off with a funny story about forgetting to send a surprise package to Michael, which sparks a discussion about the chaos of juggling schedules, rescheduling meetings, and balancing life and work.

The conversation quickly shifts to Damashe’s vending machine business. He talks about managing an increase in customers at one of his rest areas, the challenges of keeping track of sales through card readers, and the decision-making process when upgrading technology for his machines. It's a deep dive into the balance of managing a small business, embracing tech, and keeping costs in check.

From vending machines to organizing personal spaces, Damashe shares how he stays on top of labeling and organizing products, touching on the larger theme of accessibility for those who are visually impaired. Michael joins in, adding his thoughts on technology and its role in staying self-sufficient.

They then dive into a tech tangent—discussing tools like personalized podcast feeds that turn articles into audio, and how these tools make their workflows more efficient. Both share stories of their latest tech adventures and misadventures, adding a good dose of humor to the episode.

In a practical turn, Damashe opens up about the realities of managing his vending machine inventory, dealing with different locations, and the unpredictable situations that arise when transporting goods. Entrepreneurs and small business owners will find this segment particularly relatable.

Towards the end, they review the latest Apple announcements, particularly on accessibility features. Damashe gives his take on what excites him—and what disappoints him—about Apple's incremental updates. They finish up with some grocery shopping hacks, focusing on using Scan and Go at stores like Sam’s Club for maximum efficiency.

This episode is packed with laughs, tech tips, and real-world business insights, all wrapped in Damashe and Michael’s laid-back and authentic conversation style.

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