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Coaching for Early Stage Founders

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“Working with Regina over the past few months has been nothing short of life-changing.
Initially, I thought coaching would be all about tactical advice, and while Regina has certainly provided that—sharing strategies from successful companies and guiding me through key decisions—the biggest value came from something completely unexpected: she helped me debug my own mind.
After just one session, my mind was blown. I went from being stressed about failing to being pumped about work every day. Worth far more than the price I paid and opened my eyes to how working with the best coach can truly change the trajectory of your entire company.”

-Sydney Liu, Co-Founder and CEO of CharacterHub (backed by notable angels like the CEO of Rotten Tomatoes, the COO of Twitch, and YC Visiting Partner Holly Liu)

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I coach these founders on the fundamental building blocks of setting up their company for success. During our sessions, I share wartime stories of companies in similar stages as theirs and what worked / didn’t work for them.

I then hold each founder accountable on finishing their actions, working towards their goals, achieving balance in their lives to not burn out while building, and reaching Product-Market Fit.

The fundamental building blocks to nail include:

  • building a firm foundation for operating your company in a healthy way
  • setting up an accountability tracker that works for you and your team
  • deciding mission, vision, and values, and aligning your team around them for success
  • staying dedicated and focused on finding Product-Market Fit through accountability
  • delivering and receiving critical feedback to cultivate team trust

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.

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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.

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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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Who’s Regina Gerbeaux?

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, 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 hundreds of fast-scaling companies.

I work with the Top 1% of 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.

Get to know me

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

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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.
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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.

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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.

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