I’m full of regret. Should I sell again?

Dear Aunty B,

Five years ago I started a fast growing internet business, and when it was a few years old I sold my share for about $10 million. A chief executive was appointed and that business is now worth far more and I have always regretted selling out so early.

But now I find myself in the same position. My new start-up is a few years old and I have just received a good offer for it.

But I am now in the same position as I was a few years ago. The business has grown to more than 20 staff and it is no longer fun to run. But it has enormous potential.

My problem is this: if I sell I will be consumed with regret again that I have missed out on the upside, but if I stay I will find running a medium-sized company stressful. And there is no point suggesting that I keep a small stake as I am a control freak and could not bear being involved with a business that I was not running.

What do I do?

St Kilda Rd,

Oh, get over yourself. It’s simple. You, my friend, are good at start-ups. That’s what you do. That’s what you love. That’s where you excel.

You want to be part of the start-up team and energy. You have the guts to live with the great uncertainty of the first few years. You have an ability to see opportunities where others don’t, an innate sense of timing to take advantage of the changing marketplace, the passion to inspire your team, customers and suppliers. And you have the nouse to drive the business forward.

But what makes you think you could have taken it to the next level? Because probably you would have stuffed it – and blown your 10 mill.

I have met many entrepreneurs like you are who are very successful when they are king of the start-up and then stuff up the next stage because they lose focus.

I also have met inventors who have come up with some great technology and you know it will NEVER get anywhere because the inventor will not step away and let professional managers take the business to the next step.

(Then I see companies where the investor does the right thing and appoints a chief executive but the CEO is a fraud… but that’s another story.)

So Regrets, start thinking about your next start-up while you work on the sales process. And make sure you take some thinking time to uncover the source of the regret.

Why are you such a control freak? Why are you so full of regret when you have been such a success?

If you can rid yourself of regret and learn to modify your control impulses, maybe you could keep a small stake in the business, enjoy watching it reach the next level and share in the upside.


Sharlene Waters writes: Don’t think anyone will be too sorry for this guy – I would be happy with $10 million and the possiblity of another $10 million!!

Paul D Hauck at ICT Strategic Services writes: Aunty B, you said: “Then I see companies where the investor does the right thing and appoints a chief executive but the CEO is a fraud… but that’s another story.” OK – spill… what’s the story there? Bring it on.

 What are you waiting for? Email your questions, problems and issues to [email protected] right now!


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