December 6, 2023

I know you love your startup. But is it time to let it go?

James Berdigans, executive chairman of Printify explains why if you love your startup, sometimes you have to let it go

James Berdigans

5 min read

James Berdigans, executive chairman of Printify

Pretty much every startup founder will tell you that their company is their baby.

It consumes your time, energy, and passion. It often doesn’t act as you want it to. It keeps you up at night. It can reduce you to tears. 

And just like parenthood, one of the fundamental lessons in leadership is knowing when to step back. To give the company you’ve built the chance to develop and grow. 

I recently transitioned from CEO to executive chairman, which I’d compare to when your child goes off to college. As a parent, you’re still deeply involved, but no longer there day-in, day-out.  


I invested years of blood, sweat and tears into building my company from the ground up, and the relentless dedication and long hours had taken its toll. 

I eventually realised that making a change would result in a better outcome for both me and the company. 

Here’s what I learned.

Trusted advisors make all the difference 

Letting go of something you love is never easy. There is always room for doubt.   

 I found myself asking: "Have I really done everything I can? Is there enough money? Will it be able to grow without me?"

Even though the business was doing well, as a founder I personally felt like I was failing our investors because we had not yet reached certain milestones. 

I went back and forth about whether it was the right decision and finally reached out to our top advisors who had believed in the company from the beginning.  

Giving your baby the best chance of growing into everything it can be means providing a smooth transition.

On a visit to Necker Island, I plucked up the courage to ask one of our top investors, Sir Richard Branson, his thoughts on me finding a new CEO.

I was surprised when he told me that he himself didn’t always like being a CEO, and that he regularly found others for that role so he could focus on the vision.  

I am also lucky enough to have had help from other fantastic people, mentors and advisors. It is a gift to have people who will tell you the truth. When it came to me stepping down from being CEO, they all advised me to go for it because they saw the potential benefits. 

Strategies for succession 

So, I had validation to step aside, but who would take over? 

No one knows the company as well as me. The challenge was finding that person I could really trust to hand my baby over to and nurture it to the next level. 

At Printify, that meant promoting from within.

I always tried to hire people who will add value to the team with their knowledge and ability to learn quickly. Integrity builds trust, which is crucial in leadership and ensuring your successor maintains high ethical standards.  


I look for people who have what I call a proactive dissatisfaction with the status quo. 

What you want in a CEO is someone who actively identifies challenges and proposes solutions: a problem solver who will drive positive change within the organisation. 

Before you hand over the reins to someone else, you must: 

  • Make sure leadership is committed to your vision and values. If they’re not, then your baby won’t turn out the way you want.
  • Define boundaries and roles: Collaborate with your successor to clearly define responsibilities. This helps prevent confusion as you hand over vital strategic decisions.   
  • Find things to delegate: Highlight the tasks and duties that fall under daily operations. These are the ones you can hand over right away. Consider pulling in your COO or a chief of staff to help execute this part of the process. 
  • Engage stakeholders: Involve your investors in the transition process because they can provide valuable insights and support. At first, I was concerned that this change would signal that I am not committed to the company and hurt our reputation. However, I was pleasantly surprised with the support we received.  
  • Be flexible about the vision: While it is essential to maintain the company’s core values, it is important to be nimble enough to allow the company’s vision to evolve. If you were still in charge and doing a good job, you would be flexible, so don’t let the fact you’re stepping back make you suddenly stubborn. 
  • Loosen your grip: Allow your baby to grow up. Trust the new leadership team you have assembled to help the company grow. 
  • Embrace the opportunity: Transitioning from CEO to executive chairman provides the chance to focus on the big picture and the long-term mission. Make a list of all the things you’re going to do with your newfound time.   
  • Know what you won’t let go of: I knew that I wanted to be involved in key strategic decisions, so every six weeks I met with the senior leadership team off-site to spend time strategising on the direction of the organisation.  

Shepherding a startup to success is a roller coaster ride with challenges waiting for you around every corner. Knowing when to step back is a part of that ride. 

Even if you manage more than the eight years I spent as CEO at Printify, you won’t be in the position forever. 

Giving your baby the best chance of growing into everything it can be means providing a smooth transition, which requires careful planning, a strong support system, and a strategic approach. 

Ultimately, the goal is to ensure the company continues to thrive while allowing you as a founder to focus on the big picture and long-term vision. 

And for yourself, listen to your body and soul. If you’re too tired from daily execution and someone else could do a better job, then do something about it. Don’t be afraid to discuss the idea with your most trusted people and go from there.

James Berdigans

James Berdigans is executive chairman at Printify.