What it takes to say good-bye…
At the end of 2023, I made the hard decision to step down from my role as co-founder at Pair Team.
People have asked me, “how could you leave a successful, growing, and impactful company that you built with blood, sweat, and tears? How could you say goodbye to a team of such incredible people?” Those are hard questions. It took me a long time to find my answer and make this painful, necessary decision.
After leaving bedside nursing and throwing myself into 8 years of early-stage startups, I suddenly realized I was losing myself. There was a gap between the expectations of those around me and who I was growing into as an individual.
In the 5 years of building Pair Team, I got older. We got into YCombinator on my 29th birthday, and I celebrated my 34th birthday last week. I hadn’t taken the time to think about what my family might look like in the future because Pair Team has always been my “baby”, and my teammates have always been the ones I cared for like my own family members.
The reality that no one wants to admit is that women DO have to make decisions in their careers in ways that men don’t; and this is especially true for female founders. Your company deserves all of you. Your family deserves all of you. There’s no way to give them both what they deserve at the same time.
This became more clear to me as my husband and I decided to begin fertility preservation late summer last year so we could have a family if/when we wanted to. While at first this felt like a to-do task, we soon found out we are both carriers for a genetic condition that would be devastating to our future child if we didn’t address it.
As a founder, we’re often required to compartmentalize everything in our lives, but while balancing this news with the momentum of our growth and raising our Series A, my compartmentalization boxes began to overflow. It took a significant and truly unexpected toll on my mental health.
I’ve lived with an eating disorder for 31 years and have been in recovery for the last 7 years. I checked myself into treatment on my 27th birthday after realizing the hypocrisy and cost of spending my career on helping others be healthy, while at the very same time neglecting my own health.
It can be scary to admit you need help but in doing so, I found a stage of recovery that allowed me to become a founder. It wasn’t easy — it required setting and holding boundaries that felt conflicting. It meant no Slack after dinner, no meetings on weekends, blocking off time for lunch, saying no — these are not things you see in start-up culture and certainly not in founders, but they were required in order for me to sustain my commitment to Pair Team.
And then, one day while juggling scheduling appointments with doctors and interpreting lab results with my husband, I realized I wasn’t well. I wasn’t eating. I wasn’t sleeping. I wasn’t able to be present, creative, happy. I wasn’t myself.
So I asked for help again.
My team rallied behind me so that I could get back on my feet. They took on some of my responsibilities, stepped up to the plate to stretch into areas I’d always owned, and took the time to check in on me. I thought I just needed a few weeks to get myself back on track…
But as I stood back, I saw what was happening to my “baby”. It was growing — we raised our Series A, we continued to surpass our revenue goals, and were now helping thousands of people — the team didn’t need me the way they had needed me before.
So I had a choice to make — an incredibly painful and difficult choice to make. It was time for me to move on to improve my own well-being and that of my family.
While this is incredibly painful, I take comfort in reflecting on all the amazing things that came out of this journey as a founder at Pair Team.
The ripples of positive impact on real people are hard to wrap my head around– from the individuals we care for, to the incredible members of our team who’ve grown with us. I’ve been so fortunate to meet so many people on this journey who shared this dream of a better future for our country and helped make that dream come true. I’ve learned so much — not only the skills I needed to learn quickly along the way, but also so much about myself, my capacity to grow, and most importantly, how to listen to and honor myself.
I can’t begin to express how much gratitude I have for the outpouring of support along the way, but especially in this transition period…
Words fall short when I think about how grateful I am for my coach, Eddie, as well as my therapist. Eddie has been there for me for over 4 years to listen, to push me to be uncomfortable, to be honest with myself, and call me on my bullshit. He believed in me when I couldn’t and taught me so many life lessons along the way. I believe everyone should have a therapist and a coach– maybe not both at the same time, but I know that I wouldn’t be who I am, and Pair Team wouldn’t be what it is today, without them.
It’s times like this where you really feel how much you’re loved by your family and friends. I always tried to keep my “founder life” separate from my personal life (or at least tried) so I wasn’t sure if they’d understand.
But it turns out, they didn’t need to understand.
They saw how much I was struggling and loved me anyway. They texted me to check in, sent me cookies to cheer me up, and held me accountable in my recovery.
I think anyone who has struggled with their mental health understands how valuable it is to just know that someone cares, that they believe in you, and that they trust your ability to make hard decisions.
And to my husband who believed in me, first to take a risk on this dream, and now, trusted me in this decision that would dramatically change our lives, thank you. He has cheered Pair Team on from Day 1 when he agreed to let us start the company in our living room in San Francisco and has been there helping ‘behind the scenes’ to make Pair Team a success every day since: helping us name the company, making us dinners, moving furniture into our office, staying on top of our mail, and shipping equipment to the team, the list goes on…
Being married to a founder is hard and lonely in ways I can’t understand or articulate, but I’m so grateful to be loved by you.
Founders are happy to share press releases and big wins; no one wants to talk about the hard things like leaving their company. It was hard to know where to find support to understand how to make this decision and do right by Pair Team, but again, I asked for help from other founders — and help was there.
These founders were so generous with their time, transparency, and vulnerability about their experience. They helped with the tactical pieces, and showed up even more for the parts I didn’t even think to ask about — what to expect emotionally, how to prepare for self-doubt in my decision, how to break old habits and lean into this decision. The founder community is unlike any other and they show up when you ask for help — because no one else understands this journey and how lonely and hard it can be.
To those that answered my ask for help, thank you.
Once I knew I would have to say good-bye, I knew I would need to have some hard conversations. I was so scared to share this news with my team; what would they think of me — have I failed them? Am I not the leader they thought I was? What would happen to the company?
But as I broke the difficult news at our holiday party, I experienced the depth of the values my team embodies every day at Pair Team. They trusted me to be transparent and that I wasn’t hiding anything just because it was hard. They understood that this painful decision was a necessary part of my personal growth and that growth can be uncomfortable. They acted beyond themselves by putting aside any fears they might’ve had by expressing their support of me and my husband in such a touching way. I felt so seen and heard. Thank you.
And I was pleasantly surprised to experience the same level of support as I shared the news with our board, investors, advisors, and friends. I had hoped this would happen, but I understood this decision may be taken in a different light. Their ability to leave the “business side” out of the conversation and not think of me as just a founder, but instead support me as a human, speaks volumes about the incredible community we’ve built at Pair Team whose actions reflect a deep support of our mission. Thank you.
Words definitely fall short when I think of how much I love and appreciate my co-founder, Neil. I wouldn’t have ever dreamed I was capable of starting a company if not for Neil. We’ve been friends since our days at Forward, but as I questioned my next career decision back in 2018, he was the one that reminded me (almost daily) that I was capable of making a difference in a healthcare system I was so burnt out by as a nurse.
I wouldn’t have done this with anyone else, and I don’t believe I would be able to make this decision to prioritize myself if not for having Neil as a co-founder, friend, and brother. We’ve grown up together over the last 8 years — we saw each other get engaged, married, suffer family loss, and together, experienced all the pain and growth this journey required of us.
I told Neil “it was time” while we were on a walk in downtown SF. I wasn’t sure how he’d react — we had just raised capital, signed a bunch of new contracts, and had incredible opportunities ahead of us; would he think I was letting him down somehow? As I told him with tears in my eyes, he turned to me, hugged me, and told me he loved me. We sat on the sidewalk holding each other, cried, reminisced on all the highs and lows together, and just, well, cried. While I won’t be seeing him all day every day moving forward, he’ll always be family. Thank you, Neil.
Last but not least, thank you to this community. Thank you for supporting me and Pair Team all these years. You’ve cheered us on every step of the way, and answered our call when we needed help — so many of our teammates and partnerships have come from you telling people about us and our mission.
Most of all, thank you for letting me be vulnerable as I share this news. Brené Brown said it well when she said, “we associate vulnerability with emotions we want to avoid such as fear, shame, and uncertainty. Yet we too often lose sight of the fact that vulnerability is also the birthplace of joy, belonging, creativity, authenticity, and love”. I feel that joy, belonging, creativity, authenticity, and love now.
So what now?
I spent February really prioritizing my health and getting my strength back. In March, I finally (and successfully) underwent an IVF retrieval and we have viable embryos to start our family with. In April, we packed our life and our pug, Larry, to board a flight to Rome to be with family and soak in a culture that prioritizes slowing down, being present with your loved ones, and enjoying really good food. I know that the next few months, if not more, are going to require some deep work to untangle who I am as Cassie from who I am in my email signature.
But beyond that, I’m not sure what the future holds. But I do know I’ve found a passion for helping others achieve their dreams and I want to use this next chapter to help others the way others have shown up for me. I truly believe in the impact a coach can have for a founder, the impact an advisor can have for a company, and the impact a trusted person can have to swoop in on a project when you’re in a pinch.
But for now, my mission is to slow down, play, and explore in ways I couldn’t find space for before.
Someday I’ll answer the emails, messages, and comments I’ve received over the last few months — it’s not personal that I haven’t responded; it’s a practice of holding this boundary to prioritize myself during this time and I’m really excited to reconnect with you then. And someday, I’ll share more about my journey, because I believe being vulnerable and transparent can help others who are struggling, too.
But for now, I’m going to slow down, play, and explore.
