Confessions From The Home Office Podcast

Episode 73: Tyler and ‘the Ladies’


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This episode wasn’t planned, and it’s not about business or marketing. It’s about a moment that turned into something much bigger.

I share the story of how a simple stop in a parking lot led to months of helping Tyler, a young man experiencing homelessness, and his two dogs. What started as grabbing food and supplies turned into navigating real challenges; ID replacement, housing barriers, mental health, and the slow, complicated reality of rebuilding a life.

Along the way, I talk about what helping someone actually looks like behind the scenes—the generosity of community, the frustration, the small wins, and the importance of staying present even when progress is slow.

This is a real-life reminder that meaningful things don’t always show up neatly, and sometimes the most important work is simply not looking away.

If you want to donate to help Tyler, friends have been sending to my Venmo: @hurricanewendi. Every bit will be used to help Tyler and the Ladies.

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Confessions From The Home Office PodcastBy Wendi Hill