Get On The Damn Plane

Read time: 6 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.

April 2025

I stepped out of the workshop and walked down the block to find a coffee shop.

A few emails had just come in, and I needed a quiet place to sit, open my laptop, and respond. I ordered an iced tea, found a spot in the corner, and got to work.

Twenty minutes later, I closed my laptop and just sat there.

Tears started to fall down my face.

For the first time, I could feel it: 

Holy shit, this is working.

Months of patient follow-ups, sample newsletters, ignored DMs, and loose introductions had all converged in the same week. Three more clients signed contracts with me, bringing me to a total of 6. Double what I had the month before.

It was all hitting at once.

In January, I decided to get intentional about growing my ghostwriting business.

That meant posting on LinkedIn, sending cold DMs, asking for referrals, attending conferences — doing whatever it took to meet startup founders who wanted to publish founder-led newsletters and LinkedIn posts.

At one point, I had sent out more than 25 custom sample newsletters. Each one was tailored to the founder. I thought, this will set me apart. This is how I’ll show what I can do.

Most of the time, I never heard back.

A few opened the email. A couple replied, "cool idea." Then nothing. Silence.

Each non-response chipped away at my confidence. I started to wonder if maybe the writing wasn’t that good. If I was fooling myself into thinking people needed this. I’d follow up once, twice, sometimes three times... still nothing.

When I got my first sales call with a potential client, I was scared shitless. I had this story in my head that “I wasn’t a sales guy.” And it showed. I would stumble on my words. Struggle to answer questions. Sound unsure of my pricing or packages.

Part of the reason is that I had never done any of that before. I never had a sales job in my life. I had that stigma of sleazy car salesman in my head, and I didn’t want to be that.

Then we’d get off the sales calls and nobody would buy.

I remember one afternoon just staring at my screen, thinking:

Am I wasting my time? Do these founders even want this? I was putting in real hours, offering real value and getting ignored.

Still, I kept going.

I pushed through the discomfort, even when the results weren’t hitting. I tweaked and experimented with different messages. Talked to people in different industries. Showed up to different events.

That led me to Climate Week in San Francisco.

It was April and I still hadn’t landed any new ghostwriting clients.

Then I saw a post about a climate tech week happening in SF. Dozens of events. Panels. Mixers. Happy hours. And the main attendees? Startup founders.

At that point, all of my 3 clients had come from existing relationships — a friend from high school, someone from a mastermind, and my best friend. Convincing people online to take a bet on me wasn’t working.

So I decided I needed to get in the room. Learn about people and their businesses. Build connections on a human level.

But I went back and forth for days on whether to go to SF.

I had just wrapped up a family trip in Florida. The conference started that Monday. I had a bachelor party the following weekend. I was already tired and stretched thin.

The trip would mean a $450 flight, $500 hotel, Ubers, meals and a calendar that was starting to make me anxious.

Saturday night, two days before the conference started, I still hadn’t booked.

I kept thinking: Why would some guy who knows nothing about climate tech be at a climate tech conference? What am I really doing here?

And then a different question surfaced:

Will I regret going?

Probably not.

At the very least, I’d learn about something I was curious about. I’d see a new city. And I’ll probably meet someone interesting.

But not going?

I knew I might regret that.

So I pulled the trigger. I booked the flight.

I wasn’t going to pitch. I was going to learn. To follow my curiosity. To talk to people building interesting things and see what challenges they were facing.

I cobbled together an itinerary of free events, booked the cheapest hotel I could find, and flew to SF.

What I didn’t know was that all the seeds I had planted in the months prior were about to sprout.

The first was a fintech founder I had spoken to for fifteen minutes back in January through a mutual friend. After our call, I sent him a long email with samples and even wrote a mock newsletter based on content I found online. 

All I got was a one-line reply:

"This newsletter is pretty solid."

Then... nothing. For weeks.

I followed up. No reply. Followed up again six weeks later. Crickets.

Until now.

Out of the blue, the email came in, "What do you charge for founder-led newsletters again?"

One 10-minute call later, he was in.

The other new clients? That started months earlier too.

I went to a newsletter conference in Austin. Dropped $1K on the ticket even though I barely knew what my niche was yet. I didn’t have a polished pitch or a well-defined business.

All I had was my three random clients.

But still, I showed up. Told people I was a writer. Focused on founder-led newsletters.

A guy sat down at my lunch table on the final day of the conference and asked what I did.

I told him I was a ghostwriter.

He immediately launched into a 10-minute explanation about his newsletter growth company, past startup exit, Thiel Fellowship, and proprietary newsletter algorithm. His business captures high quality subscribers for newsletters and he had tons of connections in Silicon Valley… but he needed writers.

At first, I wasn’t sure what to make of him. He was intense. Confident. Direct. My initial reaction was uncertainty… was he for real?

But when he left, another guy sitting next to me leaned in:

"You should follow up. That could be a big opportunity."

He was right.

I texted him a week later. We hopped on a call. He loved my samples. Said he wanted to work together.

Then nothing.

Deals fell through. Momentum stalled. Two months passed.

I figured he moved on.

Until I got the text in SF:

“Two clients ready to go. You in?”

We signed a subcontractor deal. I’d write. He’d grow their list. In 48 hours, I had doubled my client base.

None of this happened overnight.

It came from building relationships. Following up. Being patient. And showing people what I could do, without asking for anything in return.

When it all landed, I was sitting in that coffee shop.

Smiling. Crying. Overwhelmed.

Because for some reason I had kept going when I wasn’t sure it would work. For some reason, I had faith that if I continued putting in the reps, the results would follow.

None of these clients came from Climate Week.

But they signed while I was there…After getting on another damn plane. 

Turns out, I don’t get to choose when it hits.

Only whether I keep showing up.

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