👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

Hi there,

You may be aware that when I’m not writing this newsletter, I work with founders 1:1 as an executive coach.

But what does that actually mean? Maybe you’ve heard of coaching and lightly considered getting a coach to support you. Maybe you’ve gotten turned off by coaching from some of the people on the internet that call themselves coaches ( 🫣 ).

In either case, today’s newsletter will clarify some stuff!

We’ll get into:

• What coaching is really all about

• What it’s like to work with me

• Examples of how I coach

And also, I have three events for founders (online and IRL) happening over the next two weeks. Scroll down to Happening at Within for details.

What Actually is Coaching?

WHAT MADE ME WRITE THIS EMAIL

There’s a part of me that’s been hovering in the wings, nudging me to “just hurry up and write a Q4 sales email!” - an email to promote my coaching services and find a few more aligned clients heading into 2026.

This part of me is rational. She’s absorbed a lot of marketing and business advice: “Move people down the funnel,” “articulate the pain point,” “clarify the value prop.” She looks at other people’s playbooks and wants me to follow suit.

And I appreciate her. She’s trying to help me grow my business so it’s financially viable and looks “successful.” I get her intention. She’s protecting the part of me that’s scared of not having enough, not doing enough, and not being enough without a high-growth, “wildly successful” business.

But I’m trying to build a business that isn’t led by my protector parts. I’m trying to build one led by my soul—where the business plan comes from inspiration, purpose, and intuition. Where decisions are made from deeper wisdom. Where aligned action flows from my gifts and what feels fun, meaningful, and expressive.

So today, instead of writing a sales email, I’m writing an un-sales email.

I’m not totally sure what that is yet. But I know what it’s not:

• It’s not promising I can make all your problems go away.

• It’s not preying on insecurities or the self-improvement complex.

• And it’s DEFINITELY not written with ChatGPT lol.

What I am feeling called to share is what coaching with me is all about.

Whether or not you feel called to work with me afterward, my hope is that this email gives you clarity and empowerment as you think about what kind of support you want in your life and business.

So let’s dive in.

Before I talk about what it’s like to work with me, it feels important to start with a shared understanding of what coaching actually is—and what it isn’t. There’s so much noise in this space, and real coaching is often misunderstood. So let’s begin there.

WHAT IS COACHING?

The ICF defines coaching as: “Partnering with clients in a thought-provoking and creative process that inspires them to maximise their personal and professional potential.”

That’s a great starting point. But based on what I’ve witnessed in my own practice, and what my clients have needed, I’d take it deeper and make it more personal.

To me, a great coach:

• Helps you get clear on your deeply aligned goals—what you really want in your life and business, and why, based on who you are, what you value, and what your soul is asking for.

• Supports you in building an iterative plan to move toward those goals with intention. This naturally evolves as you learn, heal, grow, and gain new information and inspiration.

• Sees and helps you reconnect with a more whole version of yourself, where your strengths, gifts, purpose, creativity, and wisdom become more accessible.

• Helps you unblock what gets in the way—often by working with what’s arising in the moment, so you can heal patterns and adopt more aligned behaviors and perspectives.

• Attunes to you and co-regulates with you, creating a safe container where you can feel, heal, and explore possibilities from a grounded place.

• Models a healthy relationship, allowing you to feel seen, understood, and held so self-worth, confidence, and self-trust can deepen.

• Is committed to their own inner work, so they can meet you at the depth you’re ready for.

• Has lived experience you can relate to or learn from, someone who feels both human and inspiring.

COACHING VS ADVISORY, CONSULTING & MENTORSHIP

It’s helpful to clarify the difference between coaching and these other forms of support.

Advisors, consultants, and mentors primarily give advice. They make recommendations, share expertise, and often tell you what they think you should do based on their experience. With advisors and consultants, you’re usually paying for that guidance. Mentors often do the same, even if informally.

Coaching is different. A coach helps you connect with your own inner wisdom. Instead of telling you what to do, they ask powerful questions, support deeper emotional and nervous-system regulation, and help you see possibilities you might not access alone. The goal is to help you make aligned decisions from a grounded, wise place.

All roles have their place:

• Advisors/mentors are great when you need new skills, knowledge, or perspective.
  

• Consultants are ideal when you want to outsource a piece of work or bring in specialized expertise.
  

• Coaching is for the deeper work of clarity, alignment, healing, and becoming the leader who can actually execute on the strategy.

And while others can offer input, I believe no one is better equipped to decide what’s right for your business or life than you. You hold more data - your intuition, your lived experience, your values - than anyone else ever could.

In my practice: the balance is roughly 80% me facilitating your deeper wisdom and 20% offering my perspective when asked. Anything I share is always framed as “take it or leave it,” trusting you to choose what’s right.

MY COACHING APPROACH

Every coach has their own approach, shaped by their training, work experience, life experience, and the clients they’ve supported. I think that’s a beautiful thing because it allows you to find someone whose way of working genuinely resonates with you.

Here’s how I’d describe mine.

My approach integrates my experience as a 2x founder, CPA, and startup operator with my post-burnout healing and spiritual journey and my coach training.

As a result, I combine business strategy with inner work—parts work, focusing, presence work, somatic work, visualization, and mindset work—to help you align your business and life with who you are, what you deeply want, and how you want to feel.

ONBOARDING

I start engagements with an in-depth onboarding form to clarify the transformation you’re seeking and to understand how you’re currently feeling across various areas of your life and business—strategy, time management, team culture, health, personal finances, relationships, community, and spirituality.

I use this information, along with our discovery call, to loosely design a personalized coaching curriculum with ideas for how I can support and guide you.

KICK OFF CALL

We begin with a 3-hour kickoff call to lay the foundation for our work.

Part 1: We explore who you are, what you deeply want, the patterns and beliefs that have held you back, and what you value.

Part 2: We map that inner clarity into your business—mission, vision, values, authentic leadership, zones of genius, and what that means for your strategy, goals, and tactics.

We leave the session with clear, values-aligned coaching goals. I then refine your curriculum—which often evolves as new insights and challenges unfold (as it should).

COACHING SESSIONS

Coaching sessions are an hour in length and typically take place every two weeks. They can go in many directions, but here are a few common types:

UNBLOCKING CHALLENGES

This is the most common type of session.

You come in with a specific challenge—navigating a tricky employee conversation, feeling defeated by a fundraise, feeling stuck or overwhelmed. When the issue is layered, we go beyond surface-level problem-solving and look at:

• How your body experiences the problem

• What emotions or stories are present

• What nervous system patterns or beliefs are activated

• What unprocessed material might be influencing your reaction

Then we work to shift and heal those patterns so you can relate to the situation from a place of trust, strength, and deeper wisdom. From there, we determine an aligned path forward.

This is how you begin to embody new ways of being—not just for this challenge, but overall.

LEARNING NEW SKILLS & TACTICS

Sometimes the focus is more tactical: recruiting, interviewing, creating values-aligned culture, launching a newsletter, structuring a fundraise.

I guide you through frameworks while asking questions that ensure you arrive at an approach that aligns with your values and leadership style.

Sometimes it’s an inner skill you need to develop. For instance if developing nervous system literacy would be supportive in your journey I might guide you through: understanding and mapping your nervous system states, identifying triggers, and learning how to shift into safety and connection.

STRATEGY

Strategy sessions can zoom all the way out to long-term vision or get granular with week-to-week energy and resource allocation.

We ensure your strategy aligns with deeper purpose, values, natural gifts, and long-term vision. We might explore:

• Visioning and brainstorming

• Strategic focus, priorities and team aligment

• Resource allocation

• Time audits

• Where your effort is generative vs. draining

PROBLEM SOLVING

Sometimes you simply need a grounded partner to work through a practical challenge. For example, I once helped a founder negotiate compensation with their co-founder by building a model in Excel and clarifying the factors involved.

(Yes, we did do a little bit of parts work to support the confidence to ask for what they deserved, but the bulk was straightforward problem-solving.)

SUPPORT OUTSIDE OF SESSIONS

DAILY RITUALS

Outside of sessions, I encourage you to practice morning intention-setting and evening reflections: reviewing how the day unfolded, gratitude, and anything that got in the way of your coaching goals (which are usually great things to bring into coaching sessions).

RESOURCES & EXERCISES

Depending on what emerges in sessions, I share frameworks, worksheets, books, meditations or podcasts (e.g., Non-Violent Communication for navigating hard conversations, time audits for energy management, grounding practices, or books for founders in transition).

TEXT & VOICE NOTE SUPPORT

You can text or voice note me between sessions if something comes up or you want support integrating. I genuinely love staying connected throughout the week.

MY UNDERLYING BELIEF

What makes my coaching approach different is this:

Most coaches ask, “What’s missing? What do you need to fix?”—reinforcing a self-improvement trap that assumes once you fix the deficiency and achieve the goal, you’ll feel whole. But that never actually works.

My approach* asks: “What if nothing is missing?”

It assumes you are already whole—and through coaching and the spiritual path of entrepreneurship, you are unfolding into even more whole versions of yourself. It assumes you already are love, joy, peace, gratitude, and compassion—and can access and embody them right now (rather only when you achieve xyz external goal).

This makes growth more empowering, meaningful, and honestly… much more fun.

Yes, we build skills and overcome challenges. But the work is not about getting from A to B because you’re insufficient. You are already infinitely worthy, lovable, and enough, exactly as you are.

*This philosophy is part of the Aletheia coaching approach, which focuses on self-unfoldment rather than self-improvement.

WHO I WORK WITH

I’ve spent my first year in business clarifying who I enjoy working with most and where my approach creates the greatest impact.

My clients aren’t defined by stage or industry, but by qualities:

They: 

1. Are founders - aspiring, current, or post-exist. They are creators of that which they believe should exist in the world.

2. Want to make a positive impact in the world - whether through their product/service/offering or by the culture they build.

3. Want to align more deeply with themselves and believe the inner work that supports self-awareness, emotional intelligence, and nervous system regulation is a critical part of their evolution as a founder, leader and human.

4. Are willing to go to the hard places - to work with what’s unfolding in the moment, not just loop on old stories or stay in the self-improvement trap.

5. Want the journey to feel meaningful and fun - we’re spending a lot of time together!

EXPLORE COACHING

If this sounds like you, here are a few next steps:

BOOK AN EXPLORATORY CALL

• There’s no expectation or commitment. It’s purely exploratory on both ends.

• It’s a chance for me to learn more about you, your business, your goals, and what’s getting in the way.

• It’s a way for you to experience my coaching first hand.

• If it feels like a fit, I’ll share what a coaching partnership could look like. 

• There’s absolutely zero pressure to sign up for anything on the spot. 

You can find a time here.

If you’re not sure yet…

STAY CONNECTED

• Keep reading this newsletter and follow on Instagram. It’s the best way to sense whether my approach resonates with you.

• You can listen to podcast interviews featuring my founder and coaching journey here (scroll down to podcasts). 

• If you’re in NYC join a Within Walk, so we can meet in real life.

• Reply to set up a virtual coffee with me. Even if you’re not ready for coaching, I’d love to get to know you and I’ll suggest other ways to welcome you into the Within World.

• I host group coaching cohorts and workshops throughout the year—keep an eye out for updates in the “Happening at Within” section below.

WITHIN WALKS

We’re hosting our last Within Walk for female founders of the year on December 19th.

And don’t worry, if it’s freezing, we’ll stay inside the cafe and I’ll lead a discussion around our theme instead of walking outside!

END OF YEAR CIRCLE

I’m co-hosting a Year-end Circle December 17th for full-time female founders.

This event is going to be all about celebrating, releasing and setting intentions for the upcoming year. There are still a few spots left!

YEAR-END REFLECTION & VISIONING SESSION

I’m leading a virtual year-end reflection and 2026 visioning session in partnership with Founders House on Thursday, December 18th at 1pm. There are limited spots for non-Founder House members so grab your spot if you’d like to join us!

• 1:1 Coaching: Want to go into 2026 with my support? Book a free coaching consultation to learn how we can work together.

• Walk with us: Join for our next Within Walk.

• Let’s be friends: on LinkedIn and Instagram. I share more startup content and what’s going on behind the scenes there.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thanks for being here.

With love,
Roslyn 💚