👋 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,

I’m sending this to you from beautiful Upstate New York where I’m taking part in a 3-day coaching retreat!

Today’s newsletter is a raw one…

It’s one of those ones where I was meditating, and then I was in tears, and then I sat down to write and process what I was feeling and it all just poured out of me onto the page.

Today I’m talking about how to heal from a co-founder break up. I’m not going to lie, this is something that’s taken time. As it should! Because co-founder relationships are a big deal.

So today, we’ll get into:

• What it means to be in a co-founder relationship

• My advice on how to feel, heal, forgive, and find peace

• Resources and reads I recommend for anyone going through this right now

Before we dive in, I want to just clarify that this newsletter was genuinely written with all of the love in my heart. I wrote it with the intention of it reaching people who need it right now… because there’s not a lot of honest and heartfelt writing on this topic on the internet (trust me, I looked for it!!).

Let’s dive in.

Where we go deep on the outer work or the inner work of building a startup.

How to Heal from a Co-Founder Breakup

When it dawned on me I wouldn’t be returning to The GIST after burning out, it came with all kinds of complicated feelings. 

Loss of identity from moving on from the company I’d started and was central to who I thought I was over the prior 6 years. 

Anxiety about the future, which was now completely uncertain. 

Relief that I didn’t need to continue burning myself out anymore.

One of the biggest emotions I felt was grief. Grief about the loss of my co-founder relationship.

If you’ve never had co-founders, let me explain what that’s like. 

They’re the people you’ve signed up to work with, collaborate with, go through the ups and downs of building a company with from when you start, until, presumably, you decide to exit.

In the beginning, when your company is just an idea with no traction, they’re the people you band together with over your hope that it has infinite potential. Over your shared vision for what you know deep down that it can and will one day become. (Even when your old colleagues are referring to it as “your little side project”).

They’re the people by your side when you make the crazy decision to quit your full-time job to build your company full-time, even when the company at that time consists of an 800-person email list, a pitch deck and a vision for how you want to impact the world. 

They’re the people that you fundraise alongside. That make you feel less alone when another investor says “no” or “I don't get the problem??”. That you regroup with to say “okay, who else are we talking to?” and “what can we learn and how do we move forward?”. And they’re the people you celebrate with when you close your first round, with money in the bank to finally build out your crazy vision.

They’re the people you stay up till midnight with, editing, fact checking and programming your newsletter with because you can’t afford a team yet.

They’re the people you live with, share meals with and bike into the office with everyday, literally spending 24 hours together, when you go through a Techstars accelerator together.

They’re the people that you grow up with. That you learn to be leaders with. That see the strengths in you that you don’t see in yourself. That you admire and respect as you see them learning and growing into great leaders too.

They’re the constant in your life as you go through breakups, moves to different cities, a global pandemic. Your speak at their weddings or get mentioned in their vows.

They’re the people that you dream with and commiserate with. That you comfort and reassure when they’re dealing with the inevitable challenges that entrepreneurship brings. And who do the same for you.

They’re the people that you think, “No one else understands what it’s like, how it feels, what we’re trying to do here, as much as these people”. 

My hot take is that the co-founder relationship is as important as your marriage. You’re signing up to be in it with them for years, decades even if that’s what it takes. You’re aligning your futures. You make financial decisions together. They’re the people you grow and evolve with.

You daydream of the day that you exit your company and celebrate alongside them, knowing the risk and the sacrifice was all worth it, and sharing pride in all that you imagined, co-created, and navigated together.

Until that is…

You burn out and have to leave. Leave the company, and leave the co-founder relationship.

Because in a group of three, I was the one that got off the train while they continued moving forward.

When this happened to me, I was consumed with grief.

I felt so incredibly alone, disoriented, lost.

I remember at the time I scoured the internet to try to find comfort in the stories of other people who had been through something like this. And I found nothing. Only articles about dealing with the equity splits and legal logistics which was… decidedly not what I was looking for. 

I yearned to feel emotionally seen. I wanted to be held by the words of others who had suffered a similar pain. I wanted advice on how to handle this gaping hole in my heart. 

I didn’t find what I was looking for. 

So today I’m sharing it: everything I’ve learned about healing from a co-founder breakup. 

1 FEEL YOUR FEELINGS 

As I faced the grief of my loss, I learned that the more you push the hard emotions away the more they simmer under the surface and unconsciously control you. And you’re not actually rid of them, even though you’ve pushed them out of your conscious mind. You’re still holding them in your body.

It was when I was ready to face the hard stuff, be with it, acknowledge it, journal about it, cry it out, feel it in my body, that it was able to eventually pass through me, and I was able to find peace on the other side. Not permanent peace. And I’d have to repeat that again and again. But the pain lessens its grip on you when you surrender. 

You have to let yourself feel it all: sadness, anger, grief, resentment, fear, whatever’s true for you. Notice where it lives in your body, maybe a tightness in your chest, a tight throat or heaviness in your gut. Breathe into that spot.

If tears come, let them. Crying is one of the healthiest ways to release emotion. You can even bring it forward intentionally — play a sad song, watch a movie that gets you — anything that helps the energy move through you.

And when you’ve felt it, give yourself compassion. Place a hand on your heart and say, “I know how much you’re hurting. I’m here.” Ask what you need: maybe a walk outside, a call with a friend, a bath. Offer yourself tenderness.

Move the emotion. We can’t process pain only in our brains. It lives in our bodies and so we need to process it there too. Go for a run, dance, attend a boxing class, or shake it out. Breathwork can also be incredibly powerful for releasing what’s stuck. Trust your body’s wisdom.

Let it out. If there are words you never said, write them down. Journal, write a letter and burn it, or talk it out with someone safe. Give what’s unspoken somewhere to go.

Make art. Sometimes pain wants to be transmuted into meaning. Write, paint, sing, create, not for an audience, but  for your own healing. That’s partly why I’m writing this now.

2 SUPPORT YOURSELF

I’m someone who has always felt the need to be independent, ever since I was little. It’s more comfortable for me to be the helpful one rather than the one who needs to be helped. It’s hard for me to admit that I’m not okay. And, this was a beautiful lesson for me in learning to receive support. My partner, friends, family, mentors and coaches all showed up for me. They weaved the support system that allowed me to feel less alone, and like there wasn’t something wrong with me. That I was worth standing by, worth loving. Which, as someone who always thought I needed to prove my worth, was quite profound.

Let people in. Let them listen, remind you who you are outside of your company, and love you even when you’re messy.

And over time, seek out new community that aligns with the person you’re becoming.

If you can, work with professionals who can help you heal on a deeper level. Coaching, somatic therapy, parts work, EMDR, breathwork — I worked with all of these modalities at different points, and each one helped me move closer to myself again.

And when it all feels too heavy, return to the present moment. The now is where healing happens.

When my mind spun into past and future, I’d ground in the smallest details — the warmth of my coffee, the color of the trees, the feeling of a song washing over me. It didn’t fix everything, but it softened it.

3 REMEMBER WHO YOU ARE

Losing co-founders is disorienting because you’re not just losing people. You’re losing mirrors, the relationships that reflected who you were becoming.

For this reason it’s useful to take some time reconnecting with yourself. I actually found that in this time of grief and loss and big emotions, I was more in tune with my true self and my intuition. When I was able to let go of the fact that I was moving on from The GIST and breaking up with my co-founders, it allowed for a ton of creativity to come up and flow through me. I gave myself permission to daydream about what I could be instead. I asked myself what my true self actually loved to do. And I reconnected with dreams about what I wanted to be that had been stuffed down years back. And what emerged was even more beautiful than what I’d last created. Because it was really true to me.

The grief became a portal to my deeper self, the one that had been waiting.

Try asking yourself questions like:

• Who am I?

• What do I love?

• What do I need to heal?

• What do I actually want in life?

• What makes me feel alive?

• Who do I want to become?

The answers might not come right away, but ask anyways and then make space for them to emerge.

Give yourself space. Like any breakup, it can be healthy to take some time away from the relationship while you’re healing and finding yourself again outside of the context of the relationship. For me, limiting communication and social media/digital content that reminded me of my co-founders — and even my own company — was healthy. Do what’s right for you.

4 FIND FORGIVENESS

If you’re in a co-founder breakup, chances are there were painful moments: things said, things left unsaid, ways you or they showed up that didn’t feel good.

The thing about forgiveness is that you can’t rush it or force it before you’re ready to. You need to allow it to unfold in its own time. I read this a bunch of times in the months following my co-founder breakup and was like ‘ok i get it I get it’, but like, I didn’t really get it. I wanted it “now”. I read the books, I tried the things, but what I ultimately got was a lesson in patience.

While there’s no formula you can follow to “achieve forgiveness”, these are what I found to be some of the elements that unfolded for me on that path.

Feel your feelings first. You can’t skip this step. True forgiveness isn’t possible while you’re still holding anger, sadness, or shame under the surface.

Heal yourself. In my experience, what enables an emotion like anger or resentment to linger, is that deep down you have something unhealed in yourself, a belief about yourself or a quality that you haven’t fully integrated. For instance, if you’re angry at them for implying that you’re not good enough or not a good person or whatever, it’s because deep down YOU still think that you’re not good enough or not a good person or whatever. 

Often, the reason this hurts so much is because it touches an old wound, one that you’ve probably built some of your personality and coping mechanisms around NOT identifying with this aspect of yourself. You’ve rejected it so fiercely because you learned you weren’t deserving of love and belonging if you embodied this trait. And so when someone suggests you are it, it brings up these feelings of anger, and underneath that, shame.

The sooner you’re able to heal and integrate this aspect, the less charge it has in your current relationship dynamic, and the more easy it is to forgive.

Don’t skip this step. To me, it’s the hardest one but it’s also the most important.

See things from their perspective. If the thing you’re seeking most to receive is compassion and understanding, then you need to GIVE compassion and understanding first. 

It’s easy to get stuck in “they shouldn’t have done that.” But when people act in ways that hurt us, it’s often their protector parts trying to shield their own pain. 

Our protector parts’ job is to protect the parts of us that remember what it’s like to feel hurt (rejected, abandoned, unloved, not good enough, humiliated, unsafe, worthless, powerless, etc.). Sometimes our protectors don’t act in ways that are aligned to how our deeper selves — which are infinitely loving, understanding and compassionate — would act. 

And so if someone did something that hurt you, just remember, the action doesn’t represent ALL of them. It was probably their protector, trying to protect their OWN hurt parts. 

It doesn’t make it okay, but it makes it understandable. 

That it actually wasn’t about you. It was about them.

Underneath our protectors and hurt parts, there is a deeper us, a presence that is inherently good, honest, wise, and loving. 

When you can see the humanness underneath their actions, and acknowledge the goodness at their core, compassion grows naturally.

Remember that reality is subjective. We all see the world through the lens of our past. When you feel hurt, you’re often perceiving someone’s actions through the filter of earlier experiences that caused pain.

The brain is remarkably efficient: it doesn’t process every new moment from scratch, but instead blends real sensory input with predictions based on past experiences. (Neuroscientists call this predictive processing.)

Keeping this in mind can be really grounding. For example, if you carry a core wound around rejection, your brain may automatically interpret certain words or actions as rejection, even when other, more neutral interpretations exist.

Forgive yourself. You probably made mistakes too. We all do. If you acted out of fear, exhaustion, or defensiveness, give yourself understanding and compassion. Thank your protector for acting the way they did and appreciate their good intentions.

Remember the love. This is the part that can feel so emotional and so complicated. 

Because underneath the hurt, the grief, the anger, there is a deep, persevering love. There are beautiful memories. There’s friendship, there’s a bond, a unity, that, even if not active in the present, never goes away. The reason it hurts so much in the first place is because of how strong that love is, how much you really care.

The hard part is holding all of these emotions together, and allowing the love to radiate strong enough that maybe, it can encompass the hurt.

This isn’t something that can intellectualized. It needs to be felt and known on a somatic level. 

Feel into that deeper knowing. When the love becomes stronger than the pain, forgiveness becomes possible.

Notice the peace in your heart on the other side.

Thank you for reading. 

If you know someone who’s going through this right now, please send it their way. 

And, if you’re looking for support in the messy middle of entrepreneurship, from someone who has truly lived it, let’s connect.

FOR FEELING

• If you’re struggling to feel and release your feelings, try putting on a sad playlist on Spotify.

• For moving through it: Try Forward Space, The Class by Taryn Toomie or Gotham 

FOR SUPPORTING YOURSELF

• If you want support with your healing, check out different modalities and see what resonates with you. Somatic Experiencing, IFS, EMDR, and coaching have all been helpful to me.

• Find community with others who are on a personal development journey. In NYC a few recommendations of mine would be:

  • Maha Rose for all things reiki, massage, sound healing and breathwork

  • Treat yourself to sauna/cold plunge at Othership — if you want a larger community feel with guided classes, or Elahni — if you’re looking for a more intimate experience.

  • Book a weekend meditation getaway somewhere like Ananda, Menla or Sivananda Yoga Ranch

  • Join us for one of our Within female founder walks!

FOR REMEMBERING WHO YOU ARE

• I really benefited from To Be Magnetic’s manifestation workshop, which not only helps you get clear on what you really want, but how you need to be expanded and healed in order to align yourself with that vision. They have a Rock Bottom workshop which I found beautiful (or you can listen to their pod episode on Rock Bottoms). 

• Take a class or a read a book about something you’ve never given yourself permission to explore!

  • I took a graphic design course with ilovecreatives, started writing this newsletter and eventually, signed up for a coaching program.

  • Finding Your Own North Star by Martha Beck is a beautiful book for this phase.

FOR FORGIVENESS

• Forgiveness by Robin Casarjian is an old but really wonderful book that genuinely helped me.

• Songs about forgiveness like Ho’oponopono by the Emmitt Sisters and Forgive by Trevor Hall made me cry and feel into forgiveness.

• 1:1 Coaching: Want to uplevel your leadership and wellbeing? Book a free coaching consultation to learn how we can work together.

• Within Walks: If you’re a female founder in NYC, join us for our next Within Walk here.

• 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.

Ouf, that was a tender one. Thanks for being here for it!

With love,
Roslyn 💚