#266:Founder Startup Grief

Founders have to get used to grieving, for your company to grow, for you to exit and move on.

Startups and change go hand in hand. Startups are created to change an industry, often very quickly. The people who build them have to be able to grow very quickly in order for the startup to reach its potential.

By the nature of time alone. A founder will evolve during their time building a company. They might get married, have a baby, enter or leave a relationship, go through any number of personal challenges. Any individual will change a lot in a 5-7 year period (or longer). However, whatever your personal story might be, your startup will demand you change.

Building a startup demands change. The growing startup demands that the founder changes from doing everything to letting go and leaning into management or leadership. It demands that whole functions are created from scratch where nothing existed before. It demands that features are iterated, scrapped or built again. It demands that your employees leave, get promoted, get a new boss or fired to take the company to its next stage. It demands you change your proposition to speak to a new customer segment. It demands you have difficult conversations. The list goes on.

Startups demand change, yet there is one part of change we rarely talk about, something that if you can’t lean into, you can never change.

Grief.

To change, you have to lose something and leave something behind. Something has to die.

Easy enough when it’s a feature, or a strategy. Harder, when it’s letting go an early team member. Even harder when it’s a part of your identity. Very hard when it’s the company itself.

To change dramatically means to encounter loss dramatically. You must end relationships. You must end stories. You must end strategies. You must kill what you started, begin again and evolve.

I struggled with this. Building Sanctus, we began life in a physical way. Placing our coaches in the offices of our partner businesses. Our business took shape as a services-led offering and quickly reached £1m ARR+. I knew we needed to be a tech-enabled marketplace to reach new heights. Yet for the first phase of our build, our team, product and business reflected a bootstrapped agency.

To evolve, that chapter had to end. That version of the business must die. I struggled to let go. This meant saying goodbye to employees that wouldn’t be the right fit for our next chapter. That meant changing relationships with our early customers who valued us as a hands on wellbeing partner. That meant adapting the ethos of our company from a bootstrapped coaching practice, to a marketplace that could 10x the impact we were currently having. It meant loss and it meant me letting go.

To go on that change journey, I needed to change. I needed to grieve the founder who’d got this thing off the ground and step into a new set off clothes. The founder who was going to take this business forward from £1m - £10m, was a new James. Different to the one who’d drew the logo on a piece of paper whilst struggling with this mental health.

A mentor of mine, Simon Rogerson, founder of Octopus Group once said to me; “every few years you need to smash up your business and start again”. I was horrified, smash up this beautiful business that I’m only just feeling the relief from? He was right. The market had moved on. Our customers were about to get more educated and, to grow further, we needed to adapt. We needed to start again.

I remember going for a walk with Alex Dunsdon (Saatchi Invest at the time) who said “there was who you were then, and there is who you need to be now” (something like that). There were a set of rules and conditions when I started my company. A few years on, there were a new set of conditions. My old world view needed to be left behind so that I could welcome in a new one. There was an old version of me in an older version of the world that created a version of my company. A new version of me would create the next version in the world now.

When you’re scaling you have to change the belief system you started with. You have to let that die. For example “I need to do everything myself” is a belief that might serve you and the company in the embryonic stages. That won’t scale and, at some point, needs to die. You have to grieve it. Grieve that you knew every customer by their name. Grieve that you and the early team all felt like best mates. Grieve what your company is now, because if you want it to evolve - it needs to look very different.

Founders have to get really good at letting things go. This can include:

• Getting really good at having ending conversations.

• Being better at communicating what you’re not going to be doing any more of.

• Being better at celebrating what you’ve achieved so far.

• Taking holidays at key jump off points to ritualise the transition from one chapter to the next.

• Celebrating and saying goodbye to team members who played key roles in your journey.

• Killing features, departments, ways of working

When you get better at letting stuff go, you create more space for the new to grow. You free up more energy to go into the new chapter feeling resourced and excited. You make it clear to the people around you who you are becoming and what the priorities are.

---

Grieving the entire company is a whole different level of grief. Exited Founders, successful or otherwise must grieve what was. Even if the company is not dead (in a successful exit scenario), their relationship to it is, and their founder identity is dying. This grief is profound and existential.

Whilst the founder may have made a lot of money and the company will be living under new ownership. The founder is grieving a huge chapter in their life that defined their existence for a long time. The founder is grieving all that was and all that could have been. This could lead to regret, guilt, confusion, sadness and depression. Entering this period of grief wholly and consciously is very important for exited founders. Ignoring the transition can leave them lost in limbo for a long time.

For the exited founder in an unsuccessful or failed exit. The grief exists in other ways. Both the loss of identity, but also the loss of the project - of what the startup could have been. There’s shame and regret. There can be lingering on past decisions or “what could have been”. Grief here can feel like a heartbreak or a divorce. In a way, grieving a startup that fails is a bit easier than grieving a startup that is sold because it’s black and white. The startup is dead. You must mourn it and move on. But many founders don’t attend the funeral and avoid the opportunity to grieve, missing invaluable learning that they could take into their next chapter.

---

Founders, whether your startup is scaling, sold or shut down. You will need to grieve. Lean into the sadness. Lean into the growing pains and don’t underestimate the emotion that change can cause within you and your team. Create rituals, celebrate, reflect and end well - I promise you. You won’t regret doing this.

Founders, learn how to grieve.

---

Founder Coaching