How To Know When It’s Time To Leave Your Startup

It was Valentines Day earlier this month.

Seems fitting the timing of this post coinciding with it.

Since I spoke about my decision to leave Adludio, the mobile advertising startup I cofounded in 2012, I’ve had a lot of people have reached out to me to tell me about their story how they’ve fallen out of love with their startup, or what they’re doing.

People who have reached out to me have said the following

  • They did something similar recently (i.e. left their business after many years)


  • They haven’t left their business, but aren’t enjoying it and are wondering if they could 

So given the responses, I imagine some of you reading this are considering it too.

If this resonates – this post is for you.

In this post, I’ll share two main reasons why I believe people consider leaving their startup or their business, and some suggestions how to help decide if the decision is right for you. I remember when I was going through the process there was very little out there to help me make the decision. So I hope this helps you.

Background: If you’re wondering why I decided to leave my business. I wrote about it in my last post, where I share in detail about the challenges it poses to an entrepreneur, such as challenging your sense of identity and other factors. Go ahead & click here and check it out first to give context.

The reasons why you may be deciding to leave

I believe there are two main reasons why people consider leaving their startups.

One is what I call ‘The $1,000,000 question’, the other I call ‘The Wrong Mountain’. 

1)The $1,000,000 question

SOS Phone call

Last week I spoke to a founder who called me and said they’re not feeling their startup anymore. They want to be making more impact in the world and they feel their business isn’t doing that.

If that is you, I will replay exactly what I told that entrepreneur (and I believe this is the case for 70% of people who have fallen out of love with their startup):

The $1,000,000 question….

I’ll tell you a story about me about 18 months ago…

It’s September 2015; I was on a holiday back home in Ireland. I was feeling low.

I was feeling low because we’d been speaking to investors for the past few months about doing a big new raise that would allow us take the inevitable next step for the business. The overall feedback was:


The business was doing pretty well revenue & growth wise so it was hard to take. In some cases, we couldn’t get even get a meeting with investors (we learned later this was mainly because of a ‘funding desert’ in the vertical we were in)

So here I was, feeling low. It wasn’t the first time, and I was well used to the entrepreneurship rollercoaster. However this time I was having a bit of an existential crisis about what the point to it all was, what were we trying to achieve, what our purpose was etc.

I called a mentor of mine Dan for advice.

He told me something that made a big impact on me:

He said many founders at some point call him asking for this exact advice.

‘The thing is’, he said. ‘Most of the founders feel this way when the business is doing badly, and they’re going through a tough spell.’

He then asked me a question that changed everything:

‘How would you feel about your business if you closed a $1,000,000 deal or investment tomorrow? How would you be feeling about the purpose of business then?’

I was honest and said:

‘Pretty damn good’

Asking that question was like a slap in the face. It made me relook at why I wasn’t feeling my business anymore.

I felt it because I had lost sight of the purpose. My ‘why’. But really it was just about pain. The Struggle.

Pain is a feeling that can cloud out judgments. Remove this emotion from the decision process first, or at the very least see what you’re feeling for what it is. Pain in that moment.

The £100,000 question allowed me to realise this.

That insight gave me the wake-up call I needed motivation, to roll up my sleeves and dive back in.

Back to the phone call

So back to my phone call with the founder who called me. I told him this story and asked him the $1,000,000 question.

His answer?

‘Pretty damn good’

What about you? Ask yourself the question: If you closed a $1,000,000 deal this week, would you cares about the purpose of your business go away?

If the answer is ‘yes’, then just realise that what you are experiencing is pain. In my experience, just seeing it for what it is, allows you to deal with it better & will probably give you a new sense of motivation.

However if the answer to the $1,000,000 question ‘no’. Then perhaps this second reason will resonate for you.

2) Wrong Mountain

Fast-forward almost 12 months. Our business has turned a corner. Our revenue had just grown 300% in the year, we’re profitable and had just signed a term sheet for our largest ever investment round.

The $1,000,000 question no longer applied. Not anymore.

But my feel of not enjoying what I was working on had turned from a whisper in my gut, to a SHOUTING VOICE!

This is similar to climbing a mountain. You spend years, climbing a mountain that (especially if it’s your first time starting a business) you have never seen the above the tree line.

And you climb. Constantly trying to figure up the best way up the mountain, focusing on fixing ropes, making sure ice picks are hitting the ice correctly and making you have enough oxygen for you and the team.

You spend 5 years of climbing the mountain; you’ve established basecamp & advance camps. For the first time in years, you stop to look around you. You look around and realise that, although you’ve learnt a lot about climbing, you’re on the wrong mountain The mountain you want to climb is across the valley.

Reasons for you feeling you’re on the ‘wrong mountain’ may vary:

  • Perhaps you started with a vision for a business and you pivoted into a solving a problem or serving customers you’re not passionate about
  • It could be when you started climbing the mountain all you wanted to do was learn how to climb. And now you can climb, you’ve learned there’s a certain type of climbing you like the most, and that type of rock is not on this mountain.
  • Maybe you can’t spend another night in a tent eating tins of spam (the canned food, not the email kind 😉 ) with this particular climbing team anymore

What do you do?

Keep climbing? You feel you’re 2/3 the way up after all.

Or do you let the team go on and you head back down, cross the valley and start climbing the other mountain that you think is right for you. Yes, you’ll start from the bottom again, but this time you know how to climb and you’re confident that is the right mountain for you.

What’s the right answer? There is a right answer I believe, but I can’t tell it to you. Because the only person who can tell you the right answer….

….is you.

However, I’ll suggest some options that may help:

You decide to keep climbing?

Good for you.

You probably won’t be as happy as you could be for the next while, but somewhere you have made the choice that the trade-off is worth it.

Keep climbing!

You decide to go back down this mountain and start climbing (or even finding) your right mountain?

Good for you.

Two options:

1) You start exploring exit options. Maybe there’s someone who would pay to get to where you’ve reached on the mountain. You should definitely explore this.

2) If that’s not an option, you decide to leave the team to finish the climb on this mountain and go down yourself. Just make sure the climbing team will be in good shape without you and get going.

The right mountain for you awaits you. Excited for you!

You realise you’re on the wrong mountain but you can’t decide which is the best thing for you?

This one is a bit more difficult.

Or at least we make it more difficult for ourselves.

Reality is….

You already know the answer.

The real question is, what’s holding you back?

My biggest piece of advice to you in this situation is this:

Whatever you decide, your decision gets easier the moment you make it.


Being an entrepreneur is hard. Sometimes you’ll be on different parts of the rollercoaster. Sometimes you may feel like you want to quit. You’re not the first person to feel this way.

Firstly find out if it’s just short-term pain by asking the $1,000,000 question, or if it’s deeper issue.

Getting that clarity is the first step.

Then you’re in a better position to make the right decision for you.

How about you?

Are you thinking of leaving your startup? If you’re struggling with this decision, I’m guessing you’d love to chat to someone about it.

Feel free to reach out to me: howard (at) , or ask any questions in the comments below.


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