450 People Told Me No

Read time: 5 minutes

Welcome back.

If you've missed our last week's letter, you can read that (and all past issues, here)

Any decent newsletter would build up to the good bit slowly. I'm going to skip that and start with a number.

450.

That's roughly how many people told me no in 2020.

I was quarantined in my bedroom (meals left outside the door like a dog with a bowl, genuinely), pitching investors on Zoom from morning till night. I made over 500 calls in two months, and almost every single one ended in a no.

When we finally got close to our first target, we stalled at around £650k. So I spent the next 100 calls asking people for £5k or £10k. Pretty desperately, if I'm honest.

A few months later, our crowdfund hit £1M in 20 minutes, and it made the papers.

That 20 minute headline sat on top of twelve months of calls and roughly 450 nos. So this week I want to talk about asking, why almost all of us do far too little of it, and how to get a lot better at it in 30 days.

BTW, I'm not the only lunatic who's done this.

An entrepreneur called Jia Jiang got turned down by an investor and took it so badly that he decided to get rejected on purpose, every day, for 100 days.

On day one, he asked a security guard if he could borrow $100. The guard said no and asked what it was for, and Jia panicked and legged it. He'd filmed the whole thing, put it online, and about 5 million people watched him bottle it.

He kept going anyway. He got Krispy Kreme to make doughnuts shaped like the Olympic rings. He got a stranger to let him play football in their back garden. He did NOT get a haircut at Petco (fair).

By day 100, about half his requests had been a yes. HALF.

The no that came back

There's a part of our story I rarely tell.

Back in January 2020, an investor we were counting on pulled out at the last minute after the government changed the rules on startup tax relief. It felt like a punch in the stomach.

That same investor kept an eye on us for the next few months. By May, they'd decided to lead our whole seed round.

I've thought about that a lot since. A no is usually someone's answer to one ask, on one day, with the information they had at the time. Plenty of nos are just early.

So keep the door open. Say thanks, stay in touch, and ask again when something's changed.

Ask out loud

The other thing I did that year was talk about the round constantly. For weeks I posted on my own Instagram and Twitter that we'd be crowdfunding, and asked anyone interested to let me know.

Plenty of people rolled their eyes. About 200 of them sent me their email address anyway, and by launch day around 1,600 people had pre-registered to invest.

Then, once we'd passed £1M, I said publicly that we'd take the round up to £1.5M. Out of nowhere, Chris Smalling, the England footballer, got in touch. One Zoom call later, he was in for £150k.

I'd never have thought to ask him. Saying it out loud did the asking for me.

The science bit (stay with me)

In 2008, Francis Flynn at Stanford and Vanessa Lake at Columbia had people ask strangers for favours. Before each ask, they guessed how many people would say yes.

They underestimated it by as much as 50%.

Turns out saying no to someone's face is awkward, so most people would rather just help. The researchers also found that nervous people tend to drop hints, and that a straight question gets the better response.

Your brain runs the maths on rejection every time you think about asking, and it's rubbish at maths.

So how do you actually do this?

For the lazy: ask for more stuff. The end.

For the curious: one ask a day for 30 days. Start small. Say the actual words.

For the serious, keep reading:

Put one ask in your calendar every day for 30 days. Yes or no, it counts.
Start with tiny ones, like a discount on your coffee or a look round a restaurant kitchen. You're building the muscle.
Say the actual words. "Would you be up for...?" A straight question does best, so drop the hints.
Name the awkward bit. Jia found that opening with "this might sound strange" made a yes more likely.
Stay after the no and ask, "What would make this a yes?" Jia legged it on day one. Don't be day one Jia.
Ask out loud. Post about what you're working on and what you need, because the right person might already be reading.
Keep a tally on your phone. In 30 days, read back through the yeses, then message one of your nos and ask again.

And please do this at home too. Ask for the extra week off. Take your partner out properly. Message the mate you've drifted from.

Asking is F*CKING uncomfortable. I made 500 calls in one year to learn that, and the yeses were worth every awkward one of them.

REAL TALK: the thing you're scared to ask for is probably a lot closer to a yes than you think.

To asking for more,

Dan

P.S. Hit reply and tell me the one ask you've been sitting on. I read every reply. Then go and make it before Friday.

One more thing worth your time

Eric Partaker and Dr Christian Poensgen have a new book out on October 20 called Ultraproductive. It's about doing your best work without trashing your health or your relationships, which is pretty much what this newsletter is about too.

One of their cheat sheets covers how to make stress work for you, and it pairs nicely with this week's issue. It includes the idea of a "stress goal": picking something that stretches you on purpose, like the big pitch or the race you keep putting off.

If you found this useful, you'll enjoy Ultraproductive by Eric Partaker and Dr. Christian Poensgen (Portfolio/Penguin). Order the book and you'll also get 9 free cheat sheets covering its core methods.

The first 10,000 people who order also get a free seat in Eric and Christian's live Accelerator program (regular price $993). [Secure yours here]

Bonus cheatsheet: If you think this is amazing, wait till you get their book Here

Make Me Well

Definitely interesting, enjoyable, etc. Arguably very predisposed to just sharing negative information about every topic it could find, which was a bit of a shame. But if you enjoy having your scepticism on everything validated, then you're the target customer. Enjoy your cynical time reading it.

Read Here

"Thrasher" by The Killers' Brandon Flowers

I rarely do this, but why not go for some music for a change? The album "Thrasher" by The Killers' Brandon Flowers is a great debut solo album

Listen Here

Mobland Season 2

It's approximately 10x better than season 1. So into it now

Watch Here

A 2020 study published in Emotion found that people who learned to accept their “non-ideal emotional states”, including low motivation, low energy, and neutral days, experienced significantly higher overall well-being and lower stress.

The key insight: self-acceptance amplifies emotional resilience, while self-judgment weakens it.

📌 Quick Takeaway →

Your average days aren’t failures; they’re emotional training grounds.
When you stop punishing yourself for being human, everything in your life compounds faster.

→ Link to study

In my goal to help more entrepreneurs/people who are looking to level up their careers, I've just started taking 1-1 consulting calls (only 1 a week)

Why book a call? Some of my expertise/success:

I've built 6 startups. 3 fails, 1 win, and 2 still going.
E-Commerce: Heights - with revenue over $40M a year.
Community: Foundrs, one of the UK's top founder communities
Podcasting: Leaders Media - Bootstrapped to #1 in business and 10M downloads
Health/Mental Health: Overcame depression, insomnia, burnout and anxiety in pursuit of success
Angel Investing: I've invested in over 100 companies
Personal Brand: Over 400,000 followers across social
Hear me on Diary of A CEO with Steven Bartlett

So if you're interested in booking a session with me to talk all things business or building a personal brand, book for 30-minutes or 45-minutes. (limited spots).

Book a Call with Dan