Day 24 of 30: A Lifeline?

8.10am. I haven’t been very good writing in recent days.

After Fridays post, I went on a drinking binge with a couple of friends which resulted in the alcohol blues on Saturday. I felt so ginger that I decided to check myself into a cheap and cheerful hotel with a swimming pool. I just wanted to float

This was an indulgence I could not really afford in light of my immediate future, but for survivals sake… a pool was needed.


Yesterday morning I woke up spritely and met with a legendary dude I look up to. I’ve taken to just asking for meetings with people for two reasons – 1/ To ask for wisdom 2/ To put my situation in their heads on the chance they might come up with something. 

The wisdom being the key though. I’m asking people… ‘What would you do if you were in my position with a week to save the company?’ 

This guy who was 62 and surrounded by a stunning funky office space told me I was doing everything he would do. He told me that he gets 99% of things in life wrong. He told me how in his past he’s taken his wifes money, his childrens education fund, and remorgaged the house to keep things afloat… and still failed. He was full of positive helpful energy… and I just came out of the meeting feeling better. That feeling goes a long way. 


Spent most of yesterday Crunchbasing and emailing random companies who would be a good fit when one of our existing investors called –

Investor – “So John, I’ve just came out of a board meeting, and I was really thinking, we can’t let this die. I mean, I don’t think this will become a big company, but I really think it needs a home somewhere. How much are you burning a month?”

John Startup – “Eh…. 40ish… I think.”

Investor – “Ok, so I propose we try and raise 200 to give you a few months, and we’ll work together to find this a new home.”

Quick mental calculation… need at very least 240k.

John Startup (on his knees) – “I mean yeah. I think that too… that would be great. Errrrrrmmmm I really think we’ll need 240 though.”

Long story short, he’s going to try get the other investors to put in to give us a 6 month lifeline. At this point I’m feeling anything would be a miracle… so this phone call is welcome news. Their call is not till next Tuesday, so we wont know till next week. It would be a savior… and I’m not counting my chickens… but we’ll have to wait and see.

John Startup



Day 20 of 30: Letting People Go

6.26pm. So had to let every non essential employee go today. 3 people left. 

I came to the decision yesterday morning when I met an advisor. I asked him… what would you do in this situation. He said… I’d let go of everyone right now. He said 2 days makes all the difference. You need anything you can get back right now. 

As I walked out of that meeting, the harsh reality of it hit me. Of-coarse thats what I needed to do. We were barely affording the next month anyway. It had to be done.

I was too chicken to do it myself. I’m no good at such things. Who is? George Clooney in that movie I guess. 

The truth is that I had to take a meeting at exactly the same time as we had planned to do it. I’m not sure if that’s a good excuse… but timing did just unfortunately clash. Hmmmm… 

It’s a bad time of the year to be doing this stuff. Heartbreaking.

I walked by Michele Bachmann on the street today. She walked straight by me. I should have asked her to cough up. She was shorter than I thought.

We had a meeting with a VC today that I met at a party a few weeks back. I only thought of him a few days ago. I emailed him and he said sure he’d meet, but he warned me that they only do investments of 75K or so, but no harm telling the story eh…

On the way to the meeting I told my colleague that these guys don’t have much money, so not to get that excited.

Suffice to say the meeting was high looking over Central Park… the most spectacular view you could imagine. After I made my presentation… he reiterated that they only do investments of 75 million or higher!!!!!!!

“Did I say we were looking for 350K? I meant we needed at least 75 million!”

Felt pretty small coming out of the meeting.

So with time ticking down, I told our investor today that we needed a bridge round of funding in the region of 350K. It’s not a huge amount for these guys… but the vibes are not what they should be. I don’t have any confidence they will give it to us, so I have to make a deal happen elsewhere.

The survival of the company is paramount, this money has to be found. It will be found!

Wont it?


Finally, just to let people know… as some are probably getting the sense that I’m about to jump off a bridge or something…

You certainly get the blues at times, but there are also plenty of laughs. When confronted with the reality, things become clear, very fast, so you gain perspectives with that.

The anxiety comes out of thinking… what the fuck will I do next?!!! 

And money! Money anxiety is an undoubted killer.

John Startup

Day 19 of 30: Crunchbasing

8.26pm. In office space alone. It’s a little chilly.

You know things are desperate when you have taken to sending the most random people emails trying to nudge their interest. 

I’ve been on Crunchbase for the last few hours. Seeing who’s invested in who… and then randomly emailing them. Of coarse it’s hard to find the emails of the multi millionaire types, but LinkedIn is proving surprisingly useful today. You can find a lot of people, and see when they’ve looked at your page. I didn’t know people actually used LinkedIn. But they do!

I managed to get the attention of a fairly high up CEO who I hope to get on the phone in the next couple of days. Touch wood.


This has become a fight for survival. Forget Series A. Forget acquisitions. It’s clear these things are not on the cards now. So my mind has been trying to work out how we might buy ourselves 6 months.

Last night I made a great offer to a CEO. I said we need 350K, and by the end of that we’ll be in proper business, having hired the exact right personal. It was a great offer… I got a little excited by it… but this morning I got the rejection response.

Yep. Things are not looking good.

I wish I didn’t believe in this fucker so much. I know we have something special. 

But the market dictates… the market dictates. All the rejections can’t be coincidence. Maybe I have bad breath?

Terrible closing line.

John Startup

Day 18 of 30: Anxiety Rising

7.35pm. Desperation is building. Need to somehow get grounded.

I’ve taken to sitting in a bar, lap top open, with a notepad, and a glass of wine… and sending biblical emails to everyone to get something to happen.

The vibes for a bridge round are not great. I’ve been doing my homework. And there is no investor lurking around just now.

I’ve got creative with my thinking. If I can buy us time we can still get this company in shape. So I need to raise about 400k to give us 6 months. I’ll take over the world with that.

I’ve just sent an email to a linchpin asking for him to invest that amount to give us the crucial time.

Time will tell.

Sorry have been so lax with these posts… it would be fair to say, my mind is currently a bit messy.

John Startup

Day 17 of 30: The Cold Call

3.39pm. I just had a huge rejection. But I actually feel shit cool about this one. 

Why? Because I literally emailed a goliath and asked him could he take a call. 

He responded. “I’m in an airport. Phone me now. My number is xxx xxx xxxx.”

Suddenly I’m on the phone to one of the worlds biggest CEOs. Within 5 minutes I had made my pitch, offering the company at a price and asking for him to commit to investing over 2/3 years.

As we go to the wire on this, we have nothing to lose. It felt like a pretty ballsy thing to do, and now I know I can cross them off the list.

His reason why he couldn’t do it was because his own company (who are MASSIVE) was in itself  a state of flux. He was candid and explained fully the position he was in. 

In the space of 20 minutes I got an answer that took me 2 weeks to get from my previous offer. 

I appreciated his honesty. For some reason I always find the people at the very very top of the trees easiest to deal with. I guess its because they are in a relatively similar situation to me… trying to keep a ship afloat…. even if they are dealing with billion of dollars.

Thats two big NOs.

Ehhh…. anyone else around?

– John Startup

Day 16 of 30: Changing The Timeline

1.38pm. Back home after 4 rambling days spreading the good word, and fighting the good fight. 

I have decided to change the mission of this blog from 45 days to raise Series A to 30 days, as the outlook now has to get even more realistic. If I can’t pull something out of the bag in the next 13 days or so… we are going to have to go back to our original investors and ask for a bridge round of financing.

The prospect of asking ‘can I some more please?’ is already making my stomach curdle. There is no guarantee we will get it. It’s humiliating, especially for a company that I feel deserves more respect. Is it the company I’m thinking about, or is it me? A bit of both I feel. 

If we don’t get an immediate yes on our request, then the first weeks of December will be spent wrapping up the company.

The hardest thing in all this is to keep up the motivation to at very least go down fighting. 


So we spent the best part of the last 3 days going from meeting to meeting. 

We would present the big idea, then get back into the rent-a-car and analyze what just happened. It felt like we are doing a theses on our industry. As we’ve been meeting some pretty big hitters they have all been giving us their views on the state of the nation. They are all different. Which to me proves that nobody knows much, and that gives confidence in it’s own way. Makes me believe that I have just as good ideas as anyone else. Of coarse I actually believe I know best… but allow me to show some humility here.

As you drive around, you try and break it down as much as you can. What is the one line that will be the winner? What are we trying to say? What is at the core of it all? What does it all mean? If a tree falls in a forest and nobody is there to hear it, does it make a sound?

At the end of the day it’s about money. And we are driving around a giant money engine. We are meeting cogs in the wheel. These cogs are all working to the same objective… get the money. Where is the money? 

Money, money, money.

Despite this, I think people were genuinely impressed by what we have achieved to date. Their eyes light up at key points. I have my presentation down. I know my lines off by heart, and can tell it to them in a way that doesn’t seem rehearsed. I take pauses that makes it seem that I am thinking about what I’m saying, as if I’m making it up on the spot. Sometimes I am. I also get laughs. Once you get a laugh off an audience you can control them. The mood becomes more relaxed, you can pivot… and change the pace.

My presentation always stands out when grouped with others. 

I spoke at a conference a couple of days ago… and I was presenting 4th out of 6 presentations. In these situations I always get extremely competitive to stand out from the others. I want to make it memorable and entertaining to the audience, and so I watch the preceding presentations… and they are often so boring.

People are too programmed in what they think makes a good presentation. You need a good story,

The point is that I’m good at presenting… now if I could only get good at raising millions and millions of dollars.

The clock is ticking faster than ever.

John Startup

Day 15 of 45: Rejection

7.46am. Jet lagged. Have been on the road for a couple of days. Will fill in the blanks latter perhaps. Had planned on doing that now, but just got an email of rejection in my inbox from the guy and industry juggernaut I offered to sell the company to last week.

“we can’t complete a purchase of this type right now as we are etc etc etc”

All I can say is fuckity-fuck-fuck-fuck…bummer…gut kicked… ugh… ahhh

Please forgive my language.

It’s a bit like a girl saying she’s just not that into you. It so hard to take.

This was clearly the best show in town, and could not avoid spending much of the last week thinking about the future possibilities. I was going to put a down payment on a small house. I was going to give some kick back to important people. Everybody was going to be happy. I was going to get a personal trainer.

Shaking my head.

So the questions are – Did we offer the company at a price that was too high? A couple of our investors had advised to ask for a highish price that my gut told me was too high. A couple of advisors told me to go low, and get out of jail. In the end I think we went mid – high. It could have been a factor. It’s hard to tell.

Did I jinx it somehow? I’m not one for superstitions, but did I tell too many friends? Did I write about it too much? I know this is nonsense… but you do think about that. Does putting out information on any level cause a train reaction of energy that comes full circle in the form of a big NO.

Nevertheless I wrote back to this guy with an email that stated how he needed to view it. Beating a dead horse? Perhaps. They say you can never make a girl fall in love with you. Is the same true in business?

Ok, off to another meeting. Blanks to be filled in later.

John Startup