FAQs

Why do I need a coach?

If you’re a CEO or part of the Executive Leadership Team, many people report to you. Theoretically, they perform better because of it. But you likely report to no one — or, you feel like there isn’t anyone that can serve as your true thought partner with your best interest in mind.

When you work with a coach like me, I become your thought partner and have your best interest in mind. I will simultaneously encourage you while challenging your assumptions and thoughts when appropriate. I offer a safe place for you to tell me how you really feel about your company and team with zero fear of backlash. And finally, I give you no-BS, tactical advice that is immediately applicable.

What is the fee and what is included?

My monthly retainer is either $7k for scaling startups (Series B or higher), or $5k for early stage startups (pre-seed to Series A). I offer payment deferral on a case-by-case basis where it makes sense.

You get a three-session money-back guarantee. If at any point during the first three sessions you find that we don't create enough value to continue, I give you all your money back. No one has ever taken me up on this. I don't intend for you to be the first.

One founder who later went on to become extremely successful gifted me 1% of his company after just one session, based on the value we created together. No, he was not flippant about equity. Yes, he found parting with equity as painful as you do. That's how well coaching with me works.

I meet with you an unlimited number of times. Most people want me to meet with them once every two weeks - it's up to you. The retainer stays the same, no matter what.

I do preferred group pricing for coaching 1-1 with multiple execs or founders.

The retainer fee also means you can reach out to me any time via email or text, and I always have an insanely fast response time. I purposefully remain selective of how many coachees I take on, so that I can offer this flexibility and availability to my founders and leaders.

What do you teach?

Having sat in every coaching session Matt Mochary did while I was his first Chief of Staff, a lot of what I teach is based on the experiments and lessons many founders before you have tried and learned. I maintain my own mental repository of every issue that has ever been discussed, what techniques were tried, what failed, and what succeeded. If you've ever wished for a Stack Overflow for how to run a company, it exists and lives in my brain.

I take that information and apply it to your situation. I'll share with you stories you'll never find on LinkedIn and X, situations that the best management consulting firms in the world wish they knew, and teach you how to apply those situations to your situation. I apply all of this knowledge in the line of questioning I present you with during our sessions together.

Many of the concepts I teach are captured in the Mochary Method Curriculum. Please feel free to use it with your team.  It is open-sourced.

I also draw on a lot of techniques from Conscious Leadership Group by Diana Chapman and Jim Dethmer. For more information, please read The 15 Commitments, found here.

For anything not captured/co-authored in the Curriculum link above, I enjoy documenting tactical advice and open sourcing operational, free Notion templates here and here.

Finally, I’m always discovering new write-ups to create through my time working with ambitious founders. My tactical advice page is ever-evolving with write-ups, posts, and templates you can use with your team. All of it is open-sourced.

What makes your coaching different?

Read my Coaching Philosophy here.

Who is Regina?

Founder and operator, turned executive coach. I was the first Chief of Staff and COO to Matt Mochary, coach to the CEOs at OpenAI, Scale AI, Flexport, Coinbase, Eight Sleep, Reddit, and more. My operational write-ups are featured in the Mochary Method Curriculum as key resources for every founder ready to scale their company, and used by fast-scaling companies.

I work with 1% Leaders. When we work together, you stop flying blind. Every problem you bring to the table, I pattern-match against decisions I’ve seen decacorn companies make behind closed doors—so you avoid the mistakes they’ve already made. If you’ve ever wished there was a Stack Overflow for scaling company challenges, it exists. It lives in my brain.

Not only will you have the information to make smart decisions, but I’ll also help you understand the psychology behind everyone you work with. Whether it's your leadership team, customers, or board, you’ll become a master communicator, able to bring people into your corner and win.

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