The cold email I'm so glad I sent

Read time: 4 minutes

Welcome to The Ascend Archives, a weekly newsletter where I share a story about a transformation, revelation, or change in thinking that has improved an aspect of my life.

A few weeks ago, I found myself standing on the field at the New Orleans Saints practice facility after an intense workout led by their head of Sports Performance.

I didn’t fully process it in the moment, but as I caught my breath and looked around the facility, I thought to myself:

This all started with one cold email.

Not a strategic plan. Not some big opportunity I chased. Just a tiny action I took 11 months earlier without knowing where it would lead.

Who Is Ryan Hawk

Whenever I fly, I download a few podcast episodes. One day late in 2024, I queued up Jay Clouse’s Creator Science, and one of the episodes featured Ryan Hawk—a name I didn’t know. But the way Ryan talked about leadership and how intentional he was with his business and relationships immediately grabbed my attention. After the flight, I looked him up and quickly fell into a rabbit hole.

How had I not heard of this guy?

His podcast has been running for years, featuring people I admire—Hal Elrod, Ryan Holiday, Morgan Housel, James Clear. I binged his episodes, joined his newsletter, and eventually read his 2024 annual review.

That’s where I found a section titled “Crazy Ideas?”

I remember reading the first one and immediately thinking:

I could help him with this.

The Cold Email

I have a history with cold outreaches. If you’ve read these newsletters over the past two years, you know I once got myself invited to an annual fishing trip through Twitter. So why not try it again?

At the beginning of 2025, I still didn’t feel like I had a real business. I had some freelancing clients, but I was still in exploratory mode. And hosting events was one of those areas I had dabbled in but wanted to explore more.

So I put together a four-page blueprint outlining how to bring Ryan’s crazy idea to life:

• The goal of the event

• A list of potential keynote speakers

• A three-phase execution plan

• An ROI analysis

Then I recorded a short five-minute video introducing myself and walking through the document.

All in, I spent 4–5 hours on something that might never even get opened.

Cold emails get a 25% open rate on a good day. Realistically, I’d need to send four of these to even get someone to look at it. But this wasn’t a mass outreach.

I had done my homework on Ryan.

I listened to him talk about cold outreach in a conversation with Sam Parr. Ryan praised his boldness in a cold email to the Airbnb founders way back in the day, and Ryan talked about writing his own cold outreaches to land podcast guests.

So something told me he was the type of person who would respect a thoughtful cold email.

I hit send on a Monday afternoon. That night, I got a response.

I still remember how I felt reading that reply—surprised, excited, validated, and a little in shock.

Little did I know that email would open doors I didn’t even know existed.

The Months That Followed

From there, we went back and forth exchanging ideas.

Ryan encouraged me to reach out to people who run some of the best events in the country, so I did. I had a conversation with an event organizer for Brent Beshore’s Capital Camp where I learned what went into organizing world-class events.

We continued researching, testing, and brainstorming.

When it came time to gauge interest from his audience, Ryan let me draft the messaging and poll questions for his weekly newsletter.

More than 215 people responded.

Slowly but consistently, our relationship continued to build. Not because I had some master plan or timeline, but because every step felt aligned. Every conversation felt energizing. Every next action felt like I was following my curiosity.

I was just continuing to show up and provide value because I was enjoying it.

But we were still in such early stages of this crazy idea that I had no idea if it would actually turn into anything.

Then I got another email from Ryan:

“Would you like to come to my Learning Leader Growth Summit this year?”

He explained that the event would have 40–45 people. It was a small, more intimate event, but it would give me a feel for what he’s done so far and the type of people who are attracted to the Learning Leader ethos.

I didn’t hesitate. I was in.

A few months later, I was in my hotel room in Scottsdale getting ready to go to the opening night’s happy hour on the putting green at the resort.

So many thoughts racing through my head.

What am I doing here? It would be so much more comfortable to be home right now.

How do I introduce myself to these people? They are all part of Ryan’s exclusive membership community. I’m just some guy who sent him a cold email and got an invite.

But I took a few deep breaths and calmed myself down.

Ryan invited me for a reason. I deserved to be here. And what’s the worst thing that could happen? I make a fool of myself and I don’t fit in?

Then I’ll never have to see these people again.

So I left my hotel room, and as I approached the putting green about 15 minutes fashionably late, I saw a bunch of people I didn’t know mingling with drinks in hand.

I gave myself one final pump up… Here we go. Let’s do this.

Little did I know what happened over the next two days would change the trajectory of my writing career.

But that’s a story for next time.

Thank you for reading! As always please reply and let me know what resonated, what didn’t, or what you question. I love chatting about this stuff!

Cheers,

Andrew