Upside PartnersBegin a conversation

Your one thing is your most valuable opportunity.

What’s your one thing?

Every leader has one. It’s the decision, the conversation, the relationship that has to move and just won’t. Your team softens what they tell you. Your board wants answers, not your doubts. So it sits with you alone, at 2am, with no one to test it against.

We’re called Upside Partners because the upside is almost always trapped in the thing you can’t move. Your one thing isn’t your problem, it’s your most valuable opportunity , sitting still because no one’s helped you get at it.

We get your one thing moving — and keep it moving.

THE CHALLENGE

You’re probably not here because something failed.

Find out what that means
THE DISCIPLINE

We’re expert at one thing: getting what you’re stuck on moving — and keeping it moving.

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HOW WE ENGAGE

It moves on day one. Then we make that repeatable.

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WHO WE ARE

Practitioners who led before they coached — and who continue to be supervised in their own work.

Dave O'Connor
Founder & Practitioner

Dave O'Connor

Dave spent two decades leading inside professional services, startups and media companies before he began coaching. He has coached clients in the NFL, national politics, creative agencies, healthcare systems and film studios. He learned firsthand what it costs to lead without anyone to think with, and built Upside to be the room he wished he'd had. He still keeps a thinking partner of his own, because no one should have to make the big calls alone. He lives in Lake Forest, Illinois with his wife Meg and their two Border Terriers, Fred and Mary.

Certifications: ACC (ICF)
Mike Tamayo
Lead Practitioner

Mike Tamayo

Mike spent 28 years inside the tech industry, first as an engineer, then as the kind of leader who realized along the way that the technical answers had stopped being the hard part. Initially applying a coaching mindset within the companies where he worked, he eventually started his own business to help leaders examine the deeper patterns, motivations, and values shaping how they think, decide, and influence others. His clients include senior executives, founders, and emerging leaders across a wide range of industries — people who want a place to think honestly about the challenges they face and the leadership they want to offer. Mike lives in Denver, Colorado with his wife and two cats.

Certifications: PCC (ICF), CPCC (CTI)

Name your one thing.

No deck, no prep. Tell us the decision or the conversation you can’t stop thinking about, and we’ll tell you honestly whether we can move it.

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