About Regina Gerbeaux

Regina is the executive coach for top-tier leaders and execs. Her current and previous clients include leaders from companies like the leadership team at dYdX (backed by Andreessen Horowitz), Ry Walker at Tembo and Astronomer (backed by Venrock & Insight Partners), Nick Bell at Fanatics Live (backed by Michael Rubin, Fanatics CEO) and Kyla Scanlon, author of In This Economy? (forward by Morgan Housel.)

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

Most recently, Regina was the Chief of Staff to Matt Mochary, who is the coach to the CEOs of OpenAI, Coinbase, Brex, and more. Matt chose Regina to become his first student on how to coach using the Mochary Method Curriculum, and she quickly became one of the most sought-after coaches in Silicon Valley. Through this experience, she built community and exchanged tactical solutions with operators from companies like Sonder, Snapdocs, WhatNot, and Sword Health.

Regina became COO of Mochary Method in 2022, where she managed the internal engineering, product, and design team, and was responsible for developing the all-in-one operating system. Companies that have used Mochary Method software include Attentive Mobile, Scale AI, Vendr, and Grammarly.

Before Mochary Method, Regina was the Head of Operations at On Deck, where she launched 10+ fellowships and 10x’ed+ their revenue that led to their successful $20M Series A raise. She was also an exited founder of a bootstrapped music business she started in college that hit $1M of annual recurring revenue by the time she was 20. She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.

Trusted by Leaders and Top Organizations

Coaching for Leaders Ready to Dominate

Trusted by CEOs and leaders at companies backed by:

Early Stage Founders (Pre-Seed to Series A)

This is the moment when your foundation will either make or break your company.

Together, we will work on the fundamental building blocks of relentlessly tunnel-visioning towards Product-Market Fit, hiring the right people and firing the wrong ones fast, and setting up scaffolding for “good-enough” structure where you can still move fast without breaking too many things

Growth & Late Stage Founders (Series B and Beyond)

You've gotten insane traction, your customers love you, and you’re growing crazy fast. It’s time for your 1 → 100 partner.

We’ll work on how you can eliminate the silos of information inside and between your leadership teams and across departments, manage your investors and board, and learn how to build your next products while still growing the existing one to create your moat.

Offsites and Conflict Resolution

At every stage of company building, your team will make or break your company. The best founders leverage offsites to build better relationships with their leadership teams and reach crystal-clear alignment, and they recognize that conflict resolutions must happen frequently to quash any drama in the leadership team.

To do this, you need an expert in human emotion and psyche to come in and help with facilitation. This is how we work together.

Executive Coaching that 1% Leaders Love

Don’t take my word for it - take theirs. Here are just a few of the things founders and leaders have said about what it’s like working with me:

“Regina transformed my ideas into an actionable plan. She quickly grasps every task, skipping the Kumbaya fluff while still making me feel fully supported. Our chemistry was great, and I always leave with a clear plan—not a long to-do list—to help us achieve our goals.”

Nick Bell
CEO of Fanatics Live and Fanatics Collectibles
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Regina is the best operator in the entire world, and she’s a machine. She has the greatest bias towards action I have ever seen. And she is an excellent coach - founders love working with her so much, they volunteer to give her 1% of their company with the value she generates for them. I highly recommend her work.”

Matt Mochary
Executive Coach to CEOs at OpenAI, Scale AI, Sequoia, Benchmark, Coinbase, Reddit, and more
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“Regina’s coaching is exceptional. She asks the hard questions with compassion and listens intently. She is my first call whenever I need support in navigating challenging interpersonal conflict and difficult business decisions. Founders and executives will be better off partnering with her.”

Chris Grouchy
Co-Founder and President of Convictional (YCW19)
,

“Thank you thank you! Regina, I've worked with a number of executive coaches before, and this was the best experience I've had. You efficiently manage letting me vent with a relentless focus on forward progress and action, while sharing relevant personal anecdotes to draw out insights. I walked away from an hour with you thoroughly pumped up and focused.”

Yifan Zhang
Managing Director at AI2 Incubator, Former Founder of Loftium (acquired by Flyhomes)
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“Regina has been one of the most influential voices in my life over the past year. She has pushed me to overcome so much fear and self-doubt. When I come to her with a problem, we have an action plan in less than an hour. I have been able to have tough conversations and make big decisions like my book launch with her support and guidance. I am a completely different person (and a much better founder) thanks to her.

Kyla Scanlon
Contributor to Bloomberg, WSJ, and NPR’s Planet Money, and Author of “In This Economy?”
,

I've known Regina for over half a decade. Working with her is like finding the missing puzzle piece you didn't know you needed. Regina brings both clarity and fire, transforming leadership from running a company to truly leading it. Her ability to pinpoint challenges and unlock breakthroughs is unreal, taking founders from reactive to thriving. I wish I'd had Regina while building my last company. If you're serious about scaling yourself and your company, working with her is a no-brainer.”

Afraj Gill
Executive in Residence at C100 and Partner at On Deck
,

“Regina keeps me accountable and challenges my assumptions. She calls me out when I'm not being honest with myself. She's committed to real, meaningful growth, pushing me to reflect on my core beliefs and align my actions with my values. Regina tackles hard truths head-on. Her understanding of people extends to company psychology - from fundraising to hiring and team management. Regina's insights go beyond just people skills. She's helped me craft compelling narratives for investors and refine my company's internal messaging. If you want to be challenged and grow, Regina will be your fiercest advocate and toughest critic. That's exactly what a founder needs.

Dara Ledjevarian
Founder of Delphi.ai (backed by Founders Fund)
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"I originally met Regina while looking for vetted coaches for my portfolio founders/CEOs, but soon found myself regularly soliciting her counsel on different topics. Before I knew it, it organically evolved into a formal coaching relationship. Her ikigai really is helping others find their ikigai. Regina is extremely adept at coaching people on how to identify what matters to them and make decisions accordingly. Highly recommend her to any Founder/CEOs."

Nakul Patel
GTM Advisor at Gradient AI and Big Sur AI, prev. VP of Sales at mmhmm ($139M total raised; Sequoia-backed)
,

Regina exemplifies Radical Candor, combining deep personal care with direct, transformative feedback. Her genuine interest in my well-being creates a safe space for growth. Drawing from her success as a profitable company founder and extensive coaching experience with high-caliber entrepreneurs, she adeptly identifies patterns and blind spots, often anticipating my needs with empathy and humility.”

Ellen Choi
Co-Founder and CIO of Aiwyn AI (Series A)
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“Regina is like a superhero for start-up executives. She parachuted into a major leadership crisis at our company, immediately diagnosed the points of friction between our founders, and crafted a plan for resolving our interpersonal challenges. She has remarkable pattern recognition from her own professional background and a real talent for bringing unspoken root cause issues to the surface.”

Theo Ellis
CEO and Founder of Friday Harbor AI
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Ready to get started?

Coaching Philosophy

This is my philosophy around my coaching and how I think about the relationship I have with each of my coachees. Please read it and see if it resonates with you.

1: Don’t be the lone wolf — team up with a coach as your partner.

Being a founder or executive can be lonely.  Because you are responsible for many people, there is a natural filter you inevitably turn on when you communicate with your team.

In order to avoid panicking the rest of your team, you believe there are problems you have to wrestle with by yourself.  And maybe you have cofounders— but they also have problems to deal with in their own departments, and therefore they are stretched thin already.

My coaching approach says you shouldn’t have to wrestle with these problems alone. I now serve as your equal thought partner to help you unpack your most seemingly-impossible dilemmas.

By working in partnership, I agree to challenge you to take the problems you have been handed and determine the best course of steps to proactively solve them.  And you agree to do the work, complete the actions you say you’ll do, and be open to thinking in patterns that differ from your normal way of problem-solving.

2: Take the easy way — learn from others’ experiences.

Most of the time, the problems we face today are not new. I bring a unique coaching perspective not only as a former COO and experienced operator, but as the former Chief of Staff to Matt Mochary.

During my time as a CoS, I was privileged to sit in on the majority of Matt’s coaching sessions with companies like Canva, Loom, Vendr, Brex, Coinbase, and many more. As a result, I have had the chance to pattern-match, study the anatomy of what makes a company function smoothly, and which solutions work (and which that don’t.)

During our sessions, when appropriate, I share the lessons and frameworks I learned in an anonymized way while observing these golden nuggets of coaching sessions. This is because I think it’s easier for you to learn from others’ mistakes, rather than re-making the same mistakes they made already.

By working together, you remain committed to listening to the stories I share with you with an open mind. You, of course, still get to consider whether these stories are applicable to you or not.

3: Figure out the next actions

I believe the best way for folks to improve is by exercising their action muscle. The more intentional you are as a CEO, the better you will perform - even if the action you decide to take is to “take no action.” You methodically decided to do this, rather than simply letting it happen.

In our coaching sessions, the question I will ask you most frequently is, “Is there an action item here?” I feel borderline religious about this question to the point where I have a post-it note on my laptop with this question (and have a feeling you’ll begin to ask yourself - and others around you - this question constantly.)

You can read more about why next actions are so important here in my write up on bias towards action.

4: Go from first principles thinking.

I will ask you during our coaching session to share specific examples of issues you are working through. But during that process, I will also help you identify themes that occur in your life. I believe that many of the problems we unpack as CEOs and leaders are symptoms rather than the root problem. It’s not enough to just cover issues: we should be holistic in addressing problems from a first-principles perspective.

For example, if you are unpacking a problem around conflict between team members, I would be remiss if I didn’t ask you about the company culture, about you as a CEO and the example you set for your team, and how you might behave outside of your company. Like the various muscles in your body, your behavior is also all interconnected.

Therefore, we will diagnose the actual issue together, staying open-minded and curious on what it might be, and peel back the figurative layers of the onion together until we arrive to the fundamental root of the problem.

5: Coaching sessions should be structured.

The worst feeling is walking away from a meeting and saying, "That was a great call!...wait, what did we cover again?"

Everything we work on together gets saved into a hub that only you and I have access to. During our session, you can focus on talking, and I do my magic of listening intently, coaching you, and making sure everything gets written down for your reference any time.

You may choose to prepare for coaching sessions. But if you're already too busy to have time to prepare, not to worry. I do a ton of preparation ahead of our call to make sure we always have things to cover and unpack.

Lastly, I always send over a list of action items for you to go through after every call. That way, you or your assistant can make sure everything gets saved into your action tracker, and you get more shit done. These are the 1% increments that make you an unstoppable leader.

Ready to Unlock Your Edge? Let's Connect.

I take on a small number of new clients each month and frequently have a waiting list. To see if we’re a good fit, please get in touch and I’ll reach out with next steps.

Resources for Leaders to Move Fast and Win

Free, downloadable operational templates on Notion to help you scale your company – from onboarding/offboarding, to action trackers to keep your team efficient and accountable.