75 – Two years today


“Hadn’t read any updates for about a year. It’s a shame he didn’t have a fucking clue what he was doing with Story because it looks like it nearly broke him, but it also looks like he’s got a much better chance this time around with whatever he’s doing. I hope he does well.” – A guy on the internet

I’m a part of the universe again.

Connected to it.

In its flow. Like I’m almost in control of it. And it’s listening.

The universe is always listening. I just wasn’t talking.

“How long ago was it?” my friend asks.

“Three years…”

Three years since Story. Since my relationship ended. When everything just kinda stopped dead.

As I’m talking I’m copy and pasting all my previous blog posts to this new website. I like writing this thing so thought I’d get a proper site. ‘So this’ was the first thing that popped into my head.

“Been a while then.”

“Yeah, been a-”

I get to the bit where I went to San Francisco and pause. I check the dates.

Fuck. That can’t be right.

Two years ago I was in San Francisco.

Two years ago today.


How is it only two? Three years is so vivid in my mind.

Can’t explain it.

I carry on reading through my old posts as I copy them over. Feels like I’m reading through someone else’s life. It’s a fucking great story. The innocence. So much confidence and excitement and hope. And then I’m so crushed. Proper drama.

Then I come across a photo. Taken in San Francisco. Me and my ex are facing a mirror in the stairwell of a hotel, I’m pointing my phone at the mirror taking the picture.

She’s got her arm propped on my shoulder. I’m in a shirt and tie, she’d just got a new haircut. We’re on our way to one of the Google I/O events where I’m pitching Story.

I’m looking at the photo and I barely recognise myself. The guy in the photo’s got everything. You can see it all over my face, I’m so proud. I’m exactly where I want to be, with exactly who I want to be with, doing exactly what I want to do.

And all of it was gone within three months.

Life huh.

It destroyed me. Because I didn’t know who I was any more. Because I had nothing left.

So I’m looking at this photo and I grin. Because it’s taken two years, to the day, and I’m realising, after everything disappeared, what grew in its place was a strength. Or maybe it was a consciousness. And it feels connected, not to a person, or a job or a place but to the universe. It feels empowering.

“So what’s your new site called?” My mate Jamie messages me.

So this… dot co. It’s the first thing that popped into my head.” I reply.

A few minutes later he sends another message, “‘Sothis’ is another name for Sirius, the brightest star in the sky.”


I didn’t know that.

“Wanker!” He adds.

74 – “Why don’t we just have three dots instead?”


There’s no toothpaste in this hotel room. I need toothpaste so bad.

“For god’s sake. Bring your own toothpaste. That’s hotel 101” Desmond texts.

“Amateur” Paul texts.

Why is that the thing.

I leave my room and go downstairs for breakfast. A woman pours me coffee. It’s black. I top it up with milk, but she already filled up most of the cup so when I pour in the milk it overflows.

I lean over to sip the coffee down a bit forgetting it’s freshly poured and burn my lips. Need toothpaste and my lips hurt.

I’m hungover and in Edinburgh.

Desmond is Canadian but based in Edinburgh. I’ve travelled up for the weekend to work on the app with him. We did some work last night and then got smashed.


Paul is on holiday with his family in New York and is coding while they sleep.

Desmond meets me in the hotel bar and is also hungover from the night before.

We get to work.

He’s coding, I’m designing. It’s productive to be in the same room for the first time. Easier for little bits of magic to happen.

For example, I’m sitting here playing about with designs. Desmond admits he has no idea about design. That’s cool. So I’m working on these three icons which make up the top navigation bar:


I like them. They’re so minimal. So inviting to tap. Friendly. Top of my game.

“Desmond. I love these icons.” I’m hungover and banging on, “They’re so… minimal. So inviting to tap. Know what I mean?”

“Why don’t we just have three dots instead?” Desmond says. “Three dots and instead of tapping between screens we just swipe? I dunno, I don’t know about design… but yeah whatever you think.”

I think he’s onto something.

I delete the icons and do three dots instead.



Suddenly, the original design is clumsy, overbearing, and ugly. And Desmond’s idea is so simple and clean. Of course that’s how it should be. Magic.

He jokes that if we carry on taking stuff away there won’t be any design left. But that’s exactly what great deisgn is. I love it.


I sit on the train back to London thinking about what we’re building. I’ve got Red Eyes by War on Drugs on repeat. The sun is shining, the sea’s next to me. I’m smiling.

Our small app idea, when we first came up with it, I didn’t think much of it. More a fun tech demo to show off our talent than anything proper.

But the more we plan it and talk about it… I don’t know… there’s something in it.

73 – “On fire tonight”

“So I have used Apiary for a mocked API. I’ll probably implement it in Node and then route requests through to the BaaS of choice.” Paul types at his keyboard.

“Man, I’m loving Apiary,” Desmond replies, “the API documentation is sooo clean and you can even simulate REST calls right from the doc pages. Hang on…” he pauses, “iOS is having trouble deserializing this response.”

“Wait…” Paul takes a look, a beat passes, “I see the problem… No comma after password…”

“Frig I thought I was losing my mind!”

“Boom. My onboard JSON parser is on fire tonight.”

I have no idea what they’re talking about but I love this. Palms sweaty, on the edge of my seat like I’m watching a fucking hollywood blockbuster.

We’re flying.

We’d come up with a new app idea in four minutes. Paul said something. Desmond replied. I replied and blam, new idea.

And now we’re flying.

The three of us are a complete team. We can make the whole product. It wasn’t like this before. Before, me and Paul needed to start a company because we needed an investor because we needed to pay for an iOS developer. It all took time and cost money and meant we only had one shot.

It’s not like that now. Now there’s no money, no investor, no company. For now, it’s just us. It’s lean and that’s perfect.

And like Paul’s onboard JSON parser, we’re on fire.

I’m back.

The real me.

Not the broken, messed up me. The real fucking me. You should see it. Hope and restlessness wrapped in talent and arrogance. Almost indestrucible. The me with a star in my chest that’s about to explode.

72 – “Sounds like it’s been quite the adventure so far.”

The last two years. Angry, upset. Happy. Really upset and really angry. Ecstatic like crazy. Fucked up. Drunk. Healthy. Wasted. Best shape of my life. Worst. Addict. I spent the summer not working. I had money. I had no money. I had less than no money. I worked. I was bored. Hope was fleeting. I moved in with my parents. I lived on my own. I moved in with a friend. Thank fuck.

I drifted.

I freelanced.

I interviewed.

I’d had everything.

Then everything disappeared.

Then nothing. Nothing for a long time.

“Don’t it always seem to go, that you don’t know what you got til-” Yep.

I waited.

I interviewed at Victoria’s Secret in New York.

I didn’t get it. I designed the best book in the world. Buy it.

I drifted.

I fantasised about taking my life in another direction. Grasping at a new hope. Make a short movie. Bar job. Move to America illegally, fuck it. Homeless. Anything to escape. Open a cafe in Stoke Newington, a shop, a bar, a space. Open one in America. Anything.

Nothing changed.

Time heals everything. Maybe, but time is fucking slow when you don’t want it to be. I mean, it takes two years for two years to go by. Two years is a fucking long time when you don’t want it to be.

I put another ad up on AngelList.co looking for a developer. Just grasping.

Then, a few weeks ago, I get an email.

A guy called Desmond. An iOS developer.

“Sounds like it’s been quite the adventure so far.” he says, “I’ve been looking for a designer to partner up with for a while. You seem talented and driven so I’m definitely interested.”

We discuss ideas. I bring Paul into the conversation. We chat about building a product. We chat about starting an agency. We chat about Story.

Story’s dead. Its moment passed us.

Paul has a small idea he’s been playing around with. We talk about that. We start working.

First time in two years, I have hope. Desmond, Paul and me.

We’re starting again. Something small at first. Really small. 42mm to be exact.

71 – Failure

“Maybe have a long hard think, is this really what you want to do?”

I’d asked Shak, a massively successful investor and advisor, for help. I’d told him how I had no developer, no investor and no money for our half-built app. And that was his response.

Pissed me off.

I sit back and think about failure.

In the last six months I’ve been hunting for a developer to join Story. I’ve had a bunch of people show interest and then disappear. We even signed one guy into the company as an equal co-founder. It got that far! Then he got a promotion at work and bailed.

There’s now a few things out there in the same vein as Story. Medium, Steller and Storehouse. None of these guys were around when we started, now they’re here and with a load of investment.

Did we fail?

Nah. We didn’t fail, we just stopped.

Like, a half built car isn’t a failure. It’s just half built.

We didn’t stop because we failed, we stopped because our investor left us. Because we ran out of money. Because we can’t find a developer. Because…

Then it hits me.

I’ve always regarded failure as this final death-like thing that comes at the end.

But that’s not failure. It’s not a big full-stop at the end. It’s a thousand real on-going things that you ignore, overlook or simply can’t see.

have failed. And not once, but over and over. I failed to get Story to the point at which people could viably use it with our initial investment. I failed to find a developer to join our team after our investment ran out. I failed to create an attractive business plan and pitch for funding.

I always assumed if Story was going to fail it was because it, as a product, was going to fail. As in, people would use Story, not like it, so therefore it failed.

I never assumed it would be me that failed Story.

So maybe Shak is right.

70 – Life changing

“What?! Serious?” Paul says.

“Yes! Fuck I can’t stop grinning.” I reply.

“Three months?”

“Well… nearly four.”

“Nearly four?! HAVE A GOOD SUMMER MATE! What are you going to do?”

Paul cheers’s my pint, genuinely excited for me.

“I know right! I don’t know. Hang out in cafes, email people. Meet people. I want to spend the next bit of my life doing something I love.”

“Go to Google’s campus in Old Street. It’s a cafe where start ups go to work. People hang out there to get ‘picked up’. See who’s there. Also get into the Wayra incubator near Euston. If you’re gonna hang out in cafes, hang out in the right ones.”

“Yeah good idea. Can you fucking believe this!”

“This is your time. Don’t fuck it up!”

“I wanna go back to America too. Airbnb my flat and get back over there.” The excitement is overwhelming me. That dark tunnel I was in… now I’m in a field. Sunshine. 360 view. I’m back and I feel proud again.

Okay. Hang on. Let’s back up a bit.


My boss winces and leans forward.

“So. I’ve spoken to HR and you’ve got two options.”

I nod my head up and down and wince a bit too.

My job role changed recently so I asked my boss about redundancy. And I wanted to leave anyway.

“First option is we move you to the UX department. Which would be a great opportunity for you. If you did that for, I dunno, a year, who knows where it could lead?”

A year. Jesus Christ. Another year in this job. Like we’re talking about getting another coffee. No way. I want the pay off.

“Second option is, you’d leave…”

Here it comes.

“… with three months pay. Plus we’ll give you a couple of extra weeks, plus whatever holiday you have left. So you’ll walk away with nearly four months pay.”

Fuck me!

“Thing is, Simon. We don’t want you to leave, we’d much rather you take this new role…”

Fuck that.

“… How do you feel?”

Fucking great is how I feel. I’m laughing inside my head.

I pretend to weigh up my options. Carry on working for another year or get paid and not work. I mean…

“Yeah, let’s do that.”

“Which one?”

“I’ll leave.”

69 – Developers


Sitting at work.

What to do.

I get an email.

Every time Story crashes I get an automated email.

My friend Claire has tried to make a story. She’s in Paris. I see all the pictures of Paris she’s taken. But the app failed to publish them. They’re lost now.

A developer could fix it. A few hours I bet.

“I tried.” she texts.

Fucking hate those crash report emails. They break my heart.

I want to shout about Story. Get people using it. But these problems… I can’t… Need it fixed.

Need a developer.

If you offered me a developer or a girl, I’d pick the developer.

The guy who helped with the last update. Tom. He did so much. Didn’t ask for a thing in return.

I wanted him to partner with us. A lot. But he’s gone and we’re back on our own.

I think back to the early days.

Meetings with Filippo. It was exciting. On the road, not looking back. Progress every day. It felt so great.

Like this is definitely what I should be filling my life with.

But we didn’t plan enough. Didn’t spec it enough. We left too many blind spots.

What to do.


I do a search. “iOS developer London”

About 40 people in the results. I google their names and find their websites. I email all of them.

Six replies, politely declining.

Two are interested.

Zero when they realise it’s not paid.

Back to square one.

I’m called to a meeting at work.

There’s about fifteen of us in the room. Two of the guys I’m introduced to are iOS developers. Two of them. Across the table from me.

My eyes widen. Pupils probably dilate. Just one of these guys is all I need.

What they can do is priceless. They can make what I need from thin air.

Developers are alchemists.

After the meeting I email one of them.

“Sorry mate, I really have no free time. It looks cool though.”

I email the other one.

He wants to meet.

68 – People


“Yeah, I’ve got an app.”

That’s it, right there. Two years, twenty grand, every emotion, it comes down to this; being in a pub and someone going ‘oh you’ve got an app?’

“Yeah man, download it.”

“What is it?”

“It’s called Story, go on the App Store and search it.”

“What’s it do?”

“It’s like this mini-blogging app… get it and see!”

“Is it free?”

Is it free.

“Yeah, it’s free. Give it a go. Try it…”

They don’t.

“I can’t even give my book away for free.” Jamie the writer tells me.

Jamie’s the best writer I’ve read. Written the funniest book I’ve read. Funnier than Catch-22.

“People just don’t do anything unless a hundred other people do it first.”

“Yeah.” he replies, “Or if a celebrity tells them to.”

“People, man. I’ve been trying to get my mate Gary, great photographer, to use Story for a year now. Never has. Just won’t do it. Not even as a favour.”

“Yeah? I’ve got people directly lying to my face about buying the book. They must think I’ve sold a load and I can’t possibly tell! These are people I’ve told not to pay and download it from my dropbox for free. But they’ve been, ‘hey, I bought it instead!’ And they’re lying!”

“People! I used to make T-Shirts. I’d write about it on a forum. If ten people on this forum bought one, and wrote that they bought one, EVERYONE would buy one. I’d sell out in a day. BUT, if I sold ten, and no one wrote about it, I would never sell more than that. It would stop dead.”

People are a crowd. One indecisive shrugging mass staring at each other in the current.

A few days later I check Story. There’s a new story by Gary. An album of pictures from his honeymoon. Holy shit. Took over a year but he did it!

“Pretty good isn’t it?” He says when I next see him.

“What, Story?” I’m happily swiping through his pictures.

“Yeah, moving the pictures around into the order you want. Enjoyed it.”

People. I guess I should stop worrying about people. In the beginning, it’s about a person, one at a time.

67 – The 12-year-old me


“Simon, hi, we need to mock up something for the ad team. I’m going to send some ads over to you. If you could fit them into your designs…”
My brain’s dying.

“… just so we have something to show them. I’ll send you over a brief.”

My eyelids are heavy. My brain is rejecting the words coming out of my boss’s mouth. I’m 32. Ads? Is that where I’m at? Placing ads?

Suddenly, the 12-year-old Simon is standing next to me. The younger me. He looks at me, looks at the chair I’m sitting in, then at my screen, then back to me. His mouth opens.

“You fucking boring loser.”

“Yeah, I know, it’s not great but-”

“What have you done with our life?”

“Look. It’s not about this. I have an app…”

“Mate, I’m so happy right now… I’m twelve years old and I know I’m gonna be crazy talented and successful. It’s a certainty in my mind. But I stand here, looking at you… you’re telling me, after 32 years, it’s just this? You, sitting there, in an office chair for nine hours a day, every single day?”

I look down at my fingers.

“What the fuck have you been doing?”

“I got a good job. People would kill for the job I have!”

“I thought we swore never to work for anyone else?”

“Look, kid, life isn’t really like that. You have to get a job and work.”

“You sound like mum. That’s all she says every day. And we both know it’s bullshit. I mean… I can see it in your eyes. You never stopped believing it’s bullshit either. Yet here you are- Why are you shifting about so much?”

“Back hurts.”

“You’ve sat in that chair so many years that your back hurts? Look. I’m gonna give you some advice. Fuck. Can’t believe I’m giving you advice. I’m twelve. You’re like, middle aged. How is it I’m smarter than you? You’re gonna quit your job…”


“Bu-bu-bu- SHHH. Everything good that’s ever happened to you, it happened when you quit whatever job it was you had. Don’t think about it. Live again. Challenge yourself. Be scared. Be excited. Just move again. Make me proud. Simon, I’m not proud of you right now.”

“I know.”

“Listen. Now you’re old, has anything really changed for you? In your heart, I mean.”

“No… when I think hard, deep down, everything is still the same. I’m still you.”

“So stop ignoring our heart then.”

“That’s some corny shit.”

“It’s corny because it’s simple. That’s why I’m happy and you’re not. You’ve let life overcomplicate things.”

“Look, I got this thing I’m working on. Story. If I can get it going, this job doesn’t matter… I’m just here so the thing…”


“Yeah, Story. Story’s the thing that will make you proud.”

“I like Story. Fight for it.”

66 – Countdown



Story launched a year ago on Christmas Eve. After one year, it has zero users and we haven’t pushed out a single update.


Our investor abandoned us making the planned development impossible. I spent the last of my money on an unproductive trip to San Francisco and outsourcing development to a woman in India.


My life crashed. I moved back in with my parents. It consumed me. Story was left static for months.


It feels as close to dead as it can get. I feel as close to dead as I can get.


But it’s not dead.


I’ve moved back to London. I found a developer who showed me how to replace all the image files. So I went crazy and redesigned everything, I made it pixel perfect. Something I never had a chance to do the first time round.


So there’s a new version of Story, sitting here. A total redesign coupled with some extra features. The next update of Story is exciting and…


… and I have a plan. It uses Story just as it is. It’s a great platform, even right now. The plan won’t cost us anything, and it will get people using it and loving it. I am so hopeful.


I still want it to exist so much. Still, one year later, no one has done anything this simple. It would be crazy to let it die. We’ve come so far. It takes so much work to turn an idea into a real thing and we’ve done that. Almost.


Happy new year