A sign on a desk saying goodbye friends

How do you leave with dignity?

founder experience m&a Feb 01, 2022

The king is dead. Long live the king. Donald Trump is no longer the US President. Whether you love him or loathe him, there is no denying his exit was spectacular. What a way to go. Talk about bringing the temple down upon your head. 

There were parallels with the great docudrama of 2020, Tiger King, which charted the rise, decline and fall of Joe Exotic. Trump and Exotic have a surprising amount in common. They are outsiders. They are rebels who revel in taking on the establishment. They have their own media channels to connect directly with their fans. They love conspiracy theories and have their own perception of truth. They are obsessed with money. They love vendettas and make every dispute personal. They have personalities to make psychoanalysts rich. They both wanted to be President for the fame it would bring them. And neither had any idea of how to make a dignified exit. They made desperate and illegal bids to stay in the limelight or avenge their enemies. Rather than enjoying his retirement, Trump must be wondering whether he will be joining Joe Exotic behind bars.

Since nearly all founders have to leave their companies eventually, it is worth considering what we can learn from these personal tragedies.

Firstly, it is useful to know when your time in a business is up. You will know it when it happens. The first signs are likely to be internal. Maybe you have achieved everything you dreamt of. Maybe you are more excited by new ideas. Maybe you can no longer stand your co-founders, investors or staff. Maybe you can’t feel anything because you are just numb with chronic fatigue. Maybe you just need the challenge of a new challenge. That passion that once raged so intensely inside you will have dimmed or burnt out. And without it, you can no longer take on and impose your will the world.

There might be external signals too. Maybe you find yourself perpetually at odds with your co-founders or leadership team. Maybe your board is becoming more assertive. Maybe your investors see their role as micro-managers. Maybe important internal meetings are happening without you. Maybe people have stopped asking what you think. Or for your approval. Maybe there are simple better people to take the business forward. Maybe no one can stand working with you anymore.

Any combination of these suggest you have entered your endgame. It will be better for everyone, especially yourself, if you can see this moment coming and prepare for it. 

Firstly, you need to protect yourself. What is your legal position? How much of the company do you own? Have all your shares vested? What are you entitled to on leaving? What rights do you have going forward? These will vary based on your status as a good or bad leaver. It is time to blow the dust off your shareholder’s agreement and seek legal advice. (If you need help, we know someone who arm wrestled Peter Thiel into the dust). 

Secondly, you need to protect your investment. That means working out what is best for your business. Most of the time this is you. But if it isn’t going to be you, who is going to provide the right leadership going forward? What else has been holding the business back? Is it time to revisit the purpose and vision, to chart a new path? A founder leaving is an opportunity for honest appraisal and to give your business an adrenaline shot. Don’t plan your exist to the sorrowful chords of Siegfried’s Funeral March. Think Arrival of the Queen of Sheba.

Thirdly, you need to manage the transition. This is where Trump and the Tiger King got it so wrong. Don’t lose sight of the bigger picture. Don’t pull the temple down on your head. Things can so easily turn nasty when they become personal. They needn’t be. Senior management changes all the time. Spotify made this a matter of policy as they expanded. The reality is that founders lose control quickly. In one study, by year four only 40% of founders were still CEOs and fewer than 25% led their IPOs. Companies are collective endeavours. While founders enjoy status and prestige, they are not always the best paid or most critical member of staff for future growth. There is no shame in saying you have had enough, achieved everything you wanted to, or can achieve more elsewhere. We all have to make sure our time is well spent. The practice of sacrificing health and sanity at work has been consigned to the history books. Tom Blomfield deserves respect for handing over the reins at Monzo. He didn’t enjoy the experience of scaling into a regulated UK bank.

You must do everything you can to reduce the impact on staff, customers and investors. This means agreeing a story and comms plan with the ongoing management. And sticking to it. Even if you are suffering from deep psychological wounds, you must find it within yourself to hold the mask in place. Government ministers do it all the time. It’s called Cabinet collective responsibility. And if they can… 

Once you are a free agent, you can recharge and refocus your energies on becoming a serial entrepreneur. That option won’t be open to you if you follow the Trump and Tiger King playbook. 


[i] https://hbr.org/2008/02/the-founders-dilemma

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