making an ask.

Reading Time: 6.5 minutes

_{Disclaimer: This newsletter is 2x LONGER than our agreed length. I tried to cut it down and failed but you’ve been warned!}

Todays issue: In this one, she share the #1 reason she doesn’t have a business: fear of asking people for things where she benefits. This newsletter chronicles uncomfortable asks and experiments to remedy it. Spoiler (for intrigue): She gets her $1 but can’t access it.

I read Noah Kagans’ book ‘Million Dollar Weekend’(okay half) — and I’ve been fixated on one specific part all week:

He talks about how the fear of asking is one of the two reasons people never build a business.

If you felt personally attacked by that sentence too, this newsletter is for you. If not, no hard feelings. Please press the X button and go have a good morning.

Still reading? Great.

Monday (Feb 12)

It all started when Chegs posted,"If you aren’t selling something, why are you online?" Okay, he didn’t say that exactly, he’s nicer but it’s how my mind translated it.

So there I was, lurking in the business section of Barnes & Noble, drowning in a year of zero product launches and ultimately no business. You know, the pity parties we are supposed to pretend don’t happen.

Then like some entrepreneur fairy godmother, Noah Kagans neon green book stuck out. If you’ve been on X, it’s been popping up all over the place. So I picked it up not even intending to read it past the first page. Until I found myself halfway through the book.

The first two chapters talked about making small asks:

• Ask someone to invest $1 into you.

• Ask friends what you’re good at.

• Ask for 10% off your next coffee.

If you read those and thought ’that sounds simple.’ Maybe, maybe not. But give it a shot. Here’s what happened when I did:

• I created a PayPal account and asked Noah Kagan for a dollar.

  

  • Asked a friend what I’m good at and ended up on a 20min call.

• And yes, if you read my Noah DM, I asked a random dude for some of his nachos — and he said yes (I know right?)

From confidence and maybe a lil ego, I slid into Noah Kagans DMs to share my wins . To my disbelief, he responded asking where I sent the dollar.

On that high, I dove into the one minute business model from the book. Because of my crap search, looked like there wasn’t a market for it. Felt like a sucker-punch. (Turns out I was searching for the wrong darn thing, but I wouldn't figure that out until Thursday.)

Undeterred by setbacks or common sense, I shot off an email to Kevin Ferrazzi, seeking his sage advice, which reading it now sounds like some pity. If you don’t know who he is, he is the king er a leading voice in networking.

Tuesday (Feb 13)

Dolla dolla bill y’all — tuns out one dollar can cause waterworks. Noah Kagan gave me my first dollar and I cried. For months, that nagging voice in my head had been whispering, "You'll never cut it in business." But seeing that first dollar gave me a glimmer of hope—felt like possibilities.

Next on the agenda: Asking three friends to invest in a service that, let's be real, didn't even really exist yet. Cue the panic-induced heart palpitations.

Wednesday (feb 14)

"Everything gets easier after your first dollar," entrepreneurs said. Well, they clearly weren't talking about me.

Valentines Day was spent overthinking all the ways people would reject me.

Despite having a few friends who could speak to my networking skills (albeit not buy because our focus is eerily close and a couple are way ahead what I want to hazily sell), my brain wouldn’t listen. So here’s what a day in the life of an overthinker looked like:

Repeated anxiety attacks over asking friends to invest in my skill, living in the fear nobody believes I can help them, and imagining all the ways they’d say no and prove the parts of my mind that says, ‘nobody trusts you’ right. Then Googling what a minor heart attack looked like to make sure I wasn’t dying.

Can’t say I don’t have an imagination, but if you see yourself in that. Promise you are not alone.

So instead, I did what anyone does when they feel incapable and don’t push in that moment — find the closest distraction.

For me, I organize and created a list:

Hope in the shape of a Dave Meier comment a few days prior: He said if I launched something, he’d support me. I was on his champion X list. Sure, he probably meant it in the literal sense of I support his work, but in my mid-spiral I like to think it meant ‘go get it tiger’. (Let me have this moment ok?)

Thursday-Friday (feb 15-16)

The minute my crusted-eyes opened, I was on my laptop and spent a hour to write a two sentence ask for three friends. Yup, you read that right. But I hit send, trembling fingers be damned.

In 24 hours two responses came in — one cautious maybe and one saying I’m too cheap. Lesson: maybe frame it less like 'I want your opinion’ and more like ‘how can I help you’.

Either way, EXCITED.

_{It would have helped it I didn’t propose the question as help instead of an ask, but let’s forget that for now.}

But in the middle of the uncertainty, clarity appeared. I finally knew what my offer was and you know what? It felt good.

With confidence and clarity I started feeling myself. Then saw Noah Kagan was hosting a Space for his book. He decided to mail his book to someone in the crowd. You just had to put an emoji in the comments. So I asked myself, ‘can I take it a step further and make an ask?’ and with shaking hands typed my comment.

Then he said my name followed by ‘you’ve been popping up a lot lately.’ Had what I’d call a mini heart attack. Guess popping up in his DM’s and tagging him on a post kept me top of mind? Either way, I got the book!

Cue: 5minute dance session in the kitchen and leaving voice notes to my friend to share the news (and me trying to get him on the Space prior).

Now have no clue if the book is signed, because checking the mailbox at least 20x a day (no seriously). But it felt good.

Saturday (Feb 17)

I can imagine you asking, ‘Okay, so are you in business yet? And you said you couldn’t access the dollar. Explain.'

For starters: Not quite. But I'm making progress, dammit. And that dollar? Paypal put my account on hold when I was finally ready to accept the money. 97 cents on hold, really?

So here’s where we are now:

I’m asking friends about their networking issues and not even scared. And while I may not have received any resounding ‘yeses’ just yet, the anxiety is fleeting (but not gone).

The questions are now:

• Do I under their problem?

• Do I need to change how I have conversations?

As I continue to fine-tune my offer. I’m going to at least launch a product I already made onto X this week. Why? Because it doesn’t hurt to at least see if someone is interested. If it works, cool. if not, then we will take it from there.

Anyway, if you see me in your DM’s asking about networking. Don’t be scared. I’m excited to learn your online networking issues so I can help you IF you want it.

Bottomline

‘Asking' seems to be a spectrum between comfort and fear.

For me, I can recommend people and products as easy as breathing. Where I struggle is making an ask where I’ll benefit.

It’s almost like there’s a stigma attached to personal gain even if it’s mutual.

Do you ever see someone who needs what you have to offer, but asking feels like trickery? Manipulation? Or even selfishness? Because SAME.

Anyway, I shared my week, because the truth is, ‘asking’ isn’t as simple as ‘just do it’. There’s real mental blockers that might exist. For me, it was a year before I even realized what my issue was. My hope is you see yourself in my bumpy ride of asking so you don’t feel like you need to be great at it on attempt number 1 or 500.

Maybe, we can get better together?

this weeks question

What is the common denominator between what you are willing to ask for and what you won’t?

cool stuff

1. Book of the week: ‘Million Dollar Weekend’ by Noah Kagan

2. Website of the week: There’s this woman named Angela Li. She is a designer at Airbnb and an underrated thinker who left social media. So of course I creeped and found her journal and thought you might benefit from reading it no matter where you are in life.

3. This weeks challenge: I have a few products I never launched. So while I’m talking to people, to help them with their networking issue, I’m pushing one of them and make it paid. Wish me luck because lordy I feel like imma poop my pants.