How I Made My First Dollar as an Entrepreneur

Read time: 7 minutes

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

Start of the Journey

On a Friday morning in February, a 10 minute podcast segment changed the trajectory of my year…and potentially my life.

It had been 3 months since I had received a pay check. I had no clarity on what I wanted to do or how to make money.

Since quitting my job, I had spent 2 months traveling the world. Eating fresh pasta in Italy, hiking in Mallorca, hopping around hostels in Australia, and exploring scenic New Zealand. After a quick stop in Houston for the College Football National Championship Game, I was back in Austin ready to get to work.

The first month consisted of a lot of trial and error…

I spent 2 weeks analyzing small businesses to buy, only to realize I didn’t want to deal with plumbers or washing cars.

I was inspired by my travels to start a travel adventure company, only to realize being responsible for epic trips probably isn’t as fun as being a participant.

Finally, I tried helping an old colleague who ran a high-end travel concierge service get more corporate sales. 25 cold LinkedIn messages later, I was back at square one.

None of these options seemed promising, but I had recently discovered writing. I had published 4 editions of my newsletter and was loving it.

That’s when I was introduced to Nicholas Cole on Ali Abdaal’s podcast. While it was click baity, the title grabbed my attention - 5 Ways to Make $1M as a Writer. Walking around Lady Bird Lake in Austin, I listened intently and took pages of notes on my iPhone. He dropped a lot of wisdom, but one segment stuck out: a step-by-step guide on how to land your first ghostwriting client.

1. Find a YouTube creator without a presence on Twitter or an Email Newsletter

2. Spend 2-3 Hours watching their videos

3. Turn the videos into words

4. Write 10 Twitter Threads and 2 blog posts

5. Send it to them for free

I knew what ghostwriting was. I worked closely with a ghostwriter in my previous role. But it never occurred to me that I could be a ghostwriter. However, something clicked listening to this pod. It was right place, right time.

My interest in writing was top of mind, his process was straightforward, and I immediately knew a creator I could try this with.

Taking Action

His name was Matt Choi and he also lived in Austin. Matt was the fun, chill, stud football player at my high school who I would occasionally run into at a house party. We were never close but when I first moved to Austin we went on a run together. Life got busy and I ended up moving to Dallas a few months later so we never met up again. Plus I’m never on Instagram so I hadn’t kept up with his journey. This wouldn’t be like reaching out to a good friend for a favor.

Before I followed Nicholas’ process, I had to see if this was something Matt even needed. I found his website, Instagram, and YouTube and searched for a link to an email newsletter. I found nothing. Then I checked his Twitter page and compared it to his Instagram. 700 followers on Twitter and he hadn’t posted in over a year. 300k on Instagram and he posts multiple times per day. I had no idea at the time how big a 300k audience was, but I knew there was opportunity here.

Before reaching out to Matt, I wanted to learn more. So I consumed every piece of free or cheap content Nicholas had on writing:

• A 60 page E-Book on how to improve digital writing

• Dozens of YouTube videos and blog posts on writing structure, pricing services, formatting, and crafting headlines

• Two of his books

  • The Art and Business of Online Writing

  • The Art & Business of Ghostwriting

After three days of reading, taking notes, and digesting the information, I was ready to execute on the strategy.

For the first time in 6 months, I spent my weekend “working”. But it felt different than the weekend work I’d do at my old jobs. That work I had to do. This work I wanted to do.

I spent the weekend watching Matt’s videos, drafting Twitter threads and a sample blog post. Then on Sunday morning, I sent him this text:

4 minutes later I get a Voice Memo from Matt…

"Yo! The fact you just texted me this is amazing. I’ve been thinking about improving my email list and would love to chat with you further. I appreciate you sending me some samples, that’s the best way to do it. I just finished a 20 mile run getting ready for Austin [Marathon] so I’m gassed, but let's get together soon"

3 hours later, I was in the sauna with Matt talking about his business, his goals, and where he needs help.

His vision fired me up. He talked about expanding into other wellness areas besides running and building businesses that don’t require him to rely on ads or brand sponsorships. He knew the importance of playing the long game. We bonded over looking up to a lot of the same people like Ryan Holiday, Jesse Itzler, Sahil Bloom and David Goggins.

This was the kind of person I wanted to work with.

I offered to write tweets and threads (IG version of X) for free for a month to test it out. That gave him time to sort out logistics with his team and determine what type of role he was looking for. It also gave me experience learning how to write posts that performed well and to put together a plan for how I can help roll out a newsletter campaign.

4 weeks later, we agreed on a scope of work that included written social media posts, a weekly email newsletter and helping him launch an online community.

A week later, the first payment was deposited into my bank account.

It worked. Nicholas’ process actually worked.

Final Thoughts

I had 3 major takeaways from landing Matt as my first client:

1. Speed to action: There is endless amounts of content: books, podcasts, emails, YouTube videos. Anything you want to learn, is being taught somewhere. But consuming the info does no good if no action is taken. I heard an idea, I got inspired, and I immediately took action on it.

2. Free work: If I had just texted Matt and asked if he needed help with emails, he might have responded since he knew me. But by spending multiple hours preparing something of value to him, it showed I was serious. I wasn’t looking for a handout or a transactional relationship. I also didn’t hard sell anything. Even if he wasn’t interested, I got to practice writing those sample tweets and blog posts.

3. Previous experience: In my previous job, I helped my boss launch a podcast, publish a book, create a digital course, and start an online community. I quit after 6 months because it wasn’t the right fit. I had no idea that the skills I learned there would be directly applicable to this new opportunity with Matt. And I would have never guessed that it would be something that excited me. Saying yes to new opportunities and building a variety of skills is critical early in anyone’s career.

I’m very grateful that Matt took a chance on me. I’m learning, having fun, and helping grow something that positively impacts thousands of people. I’m excited to continue working with Matt and see what other opportunities this experience will lead to!

Note: If sharing insights from my entrepreneurial journey and work with clients is something you're interested in seeing me do more of in the future, reply YES to this email.

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