Coffee with Kim Calendar
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Upcoming Guests
How To Lead Better With India Gary-Martin
wednesday, april 22nd, 2026
1:00 PM - 2:00 PM est
Getting stuck in the paralysis analysis space is something a lot of leaders struggle with. The truth is, good leaders make decisions quickly even when the data is not completely clear. You do the best you can with the information you have and adjust when you get more information. This is a lot easier said than done which is why I’m talking with India this week about what really works. India Gary-Martin has held global COO and CTO roles for some of the world's largest banks and has seen first hand how leaders have to make decision quickly and confidently. She’s joining us to open up the playbook on how to be decisive and tricks for balancing speed and accuracy all while being an empathetic leader. Seems like a lot to tackle as a leader? I agree. That’s why I’m bringing some tough questions for her and I hope you join us with your own!
If there’s something we should definitely discuss shoot me an email me before we meet (hello@kimkaupe.com).
to do
You Bring:
Any questions you have about leading and a cup of coffee
rsvp
KIM IS BRINGING:
Questions about how to be kind and clear in high stress situations
india IS BRINGING:
The OODA loop trick to help make decisions
Raising Capital 101: How To Fund a Business Idea with Charlie O’Donnell
Wednesday, april 29th, 2026
1:00 PM - 2:00 PM est
Raising money is one of the hardest things you’ll do in business. It’s uncomfortable and cringey and will almost always leave you feeling disappointed. But when it works, you realize why pitching yourself is worth it. I’ve pitched my idea on live television (Shark Tank!) and it was terrifying but changed the trajectory of my career. If I could go back and do it all over again I’d probably do some things differently and I definitely wish I could have had some honest advice from someone like Charlie who’s not afraid to say the hard truths out loud. In 2012, Charlie founded Brooklyn Bridge Ventures, the first venture capital firm in Brooklyn, investing in more than 100 local startups including Hungryroot, Brigit (acq. by Upbound), and Radformation. He knows what investors actually want—and how to stop wasting time chasing the wrong ones. If you’ve ever had to raise money or plan to in the future this is a conversation worth tuning in live for.
If there’s something we should definitely discuss shoot me an email me before we meet (hello@kimkaupe.com).
to do
You Bring:
Any questions you have about raising money
KIM IS BRINGING:
Questions about where most founders go wrong.
rsvp
Charlie IS BRINGING:
A roadmap to build a pitch, a network and a reputation.
Creating AI Systems With Kesha Williams
wednesday, may 13th, 2026
1:00 PM - 2:00 PM est
Identifying what tasks AI can help us with seems easy at first (tasks we dread, something monotonous we have to do) but the real magic comes in setting up repeatable systems in our workday. Kesha Williams has over 25 years of experience designing and delivering complex software and is now helping organizations adopt and implement AI safely and effectively. One of the things I’m loving most about her work is that it’s bite size and practical. She’s got something to teach the beginner who’s still just dipping their toes inI and the more advanced user who’s implementing it daily. I’m excited to dive into how to let AI handle multi step tasks and how we can automate tasks we’re doing daily. If you’re curious about how to set up repeatable systems instead of getting stuck in the cycle of prompting and rewriting join us live and bring your questions with!
If there’s something we should definitely discuss shoot me an email me before we meet (hello@kimkaupe.com).
to do
Kim is Bringing:
Questions about AI Helpers and Agents
You Bring:
A cup of coffee and your AI questions
rsvp
kesha is Bringing:
Tips for using AI in a more streamlined way at work
