My start-up is a let-down

Dear Penny,

I’m sure you’re not bad.

First off, just chillax. You haven’t ruined your career. You took a chance, it didn’t work out, and now you have to find your way back into investment banking. You made a mistake but it’s not irreversible and the situation is not beyond repair.

This is nothing new, either. In the late 1990s and into the 2000s, several of my colleagues left our bank to join a sexy internet start-up and chase the riches they thought were on offer.

We wished them well — we even had a tinge of envy — and we all wondered whether the markets would stay euphoric for long enough for them to be able to cash out their equity.

One thing I remember very clearly is that the bankers who joined start-ups worked much harder than they ever had before, often long hours and weekends, as they were trying to create a business almost from scratch.

In every case I can think of, the move didn’t work out. One of two things happened. In some cases, the former banker got used to start-up life and would end up cycling between a bunch of them over the years, to mixed success.

In other cases, the banker came crawling or even grovelling back to the bank, and their careers weren’t really damaged along the way. People forgot pretty quickly that they had left and life moved on.

This should tell you something. The reality is people have remarkably short memories, whether on Wall Street or in the City. If you tried something away from the bank and failed, everyone will understand, because almost every investment banker has dreamt of doing something similar.

We all know that these ventures pair high risk with high reward, so failure doesn’t reflect poorly on you. Nor does anyone think you were disloyal. Really, people don’t care that much about you to get upset that you left for a start-up.

The upshot is that any embarrassment will likely be transient once you’re back in the saddle. So the best thing is just to swallow your pride and plan your way back without feeling any sense of shame.

So how do you actually execute the re-entry?

I hope that when you resigned, you did it with some class and grace, thanked everyone, and didn’t burn your bridges in your exit interview.

If you’re still on good terms with your old boss, then she or he should be the first person you call. You can just be honest about what happened and admit that you took a chance and it didn’t work out. For all I know, your boss may even respect you for having given it a go.

And there’s nothing wrong with saying you miss the energy, the intensity and the whole infrastructure of the bank. I’m not saying you should go into too much detail about why it’s not working out with the start-up, but I think you can say you miss the old place and you want to come back.

If your exit was less than amicable or if your old employer doesn’t have space to take you back, then we have to think about Plan B. That means calling around other firms.

Here, it depends a little bit on how well your competitors know you, but generally speaking, I would ask a friendly headhunter to make discreet enquiries with other banks. You’re more likely to hear the unvarnished truth this way, and you will have plausible deniability. It also preserves a shred of dignity.

It’s very important that when you meet any prospective employers, you explain your disillusionment with the start-up world in the correct way. Don’t convey shame or desperation, and most of all, don’t badmouth or belittle your current employer.

So I wouldn’t say you thought the product wasn’t very good or that the office had only one toilet.

Explain why you wanted to take on this challenge, go into some of the things you’ve learned, and then just recognise that you realised this wasn’t playing to your competitive advantage. It should be clear that you’ve gained something from this experience — you’ve learnt about business and learnt about yourself.

And that is precisely why you realise you are most suited for investment banking.

You had your adventure and now, like the exiled prince Simba in The Lion King, you’re ready to come back to the fold and reclaim your position. As his wise counsellor Rafiki tells Simba: “It is time.”

Best of luck,

Craig