Jordan B. Segal on Why Great Deals Start with Better Questions

Coffee with Jon - Think Big. Get Unstuck. Grow Your Business · Jun 27, 2026 · 25m

Great talking with Jordan B. Segal, Attorney at Maddin Hauser.

5 takeaways that stuck with me:

1 - You know early—if you're paying attention.

Jordan wanted to be an attorney as a kid—and was already developing his voice.

2 - Advocacy starts with clarity.

You can't advocate for yourself—or your business—without knowing your goals.

3 - A red flag isn't a red light.

When something doesn't make sense, pause and ask better questions.

4 - Fair-fair beats win-win.

The best deals come from understanding both sides' interests.

5 - Good attorneys don't stop deals—they structure them better.

The goal…