Diary of a Matchmaker

Published: January 9, 2026
with Hiba & Zaid

He has big ideas. Side hustles. Business dreams. And you’re sitting there thinking: Is this vision… or a red flag?

Today we get real about marrying someone with entrepreneurial goals, especially in today’s economy. We talk stability vs potential, faith vs fantasy, and why “just trust me” isn’t a plan. I (Hiba) share a story about how my ex’s ‘aspirations’ cost me all my savings one day!

We unpack the questions that reveal whether a dream is grounded or risky, how support can turn into resentment, and what real partnership actually looks like when money isn’t guaranteed yet.

If you’re considering someone with business aspirations or you yourself is one, click here to download this episode’s practical checklist.

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Episode chapters

[0:00] Were We Always Entrepreneurial
[2:45] Stability Versus Potential
[5:03] Red Flags And Empty Promises
[7:10] Hiba’s experience with her ex
[13:05] Questions To Vet A Business Plan
[17:28] Clarity For Men Sharing Big Goals
[19:08] When Women Are The Entrepreneurs
[25:00] Respect Beyond Outcomes