4 Side Hustle Lessons From My First $50K
2.5 years of creator lessons
👋 Hey, it’s Preston. Welcome to issue #4 in my weekly newsletter, Side Hustle Stories. I share what I’m learning building an influencer business (currently 650K followers on IG & TikTok) while balancing a full-time job as the Head of BD at Lucid. No fluff. Just stories, frameworks, and behind-the-scenes decisions from someone doing the work in real-time. If you're building your own thing on the side—or want to—you’ll feel right at home here.
Two and a half years ago, I started building my creator business while working full-time.
I've done pretty ok. Made nearly $60K from coaching since I turned on monetization a little over a year ago. Built a paid community. Created hundreds of videos. Reached millions of people and have more than 650K followers.
I'm proud of what I've built. But looking back, there are four things I wish I'd understood sooner. Not major regrets—just lessons that would've saved me time and helped me build a creator-led business smarter.
1. Email Lists Matter More Than Viral Videos
In October 2023, I had several videos blow up on TikTok and Instagram. We're talking hundreds of thousands of views on multiple videos.
But I didn't have an email list.
For over a year, I just created content without capturing any of that attention. No newsletter signups. No lead magnets. Just videos going out into the world.
Here's what I understand now: Social media builds awareness. Email builds relationships.
When someone's scrolling TikTok, they're browsing. When they open their inbox, they're engaging. That's where I’ve built longer-term relationships and made the bulk of my sales.
I finally started my weekly newsletter about career communication — Career Comms. It's now my most valuable asset. I've even built systems to keep it sustainable: automated emails ask subscribers for topic ideas, and my community coaching calls naturally generate content.
If I'd started building my list when those videos went viral, I'd probably have twice as many subscribers today. That's a lot of missed connections.
2. Delegating Is an Investment, Not an Expense
For my first year, I did everything myself. Edited every video. Wrote every caption. Managed every upload.
I had the money to hire help—that's the beauty of a side hustle. But I thought I needed to control everything to maintain quality.
Then I hired a video editor. Instantly got 10 hours back each week.
My system now: I record for two hours once every two weeks, send 12 short-form videos to my editor, and move on. Same for YouTube—I record, they handle the rest.
Last November, I brought on a VA. She manages social posts, drafts newsletters, handles community management, creates designs. I certainly have a long way to go when it comes to managing her and delegating the right amount. But that's another 15-20 hours saved weekly.
The math is simple: 25-30 hours of work off my plate means more time for strategic thinking, product development, or just living my life.
Having a side hustle means you can afford to invest in growth. I wish I'd realized that sooner.
3. Mission Beats Niche
Everyone said to niche down, so I became "the communication coach."
It worked. I built an audience. Made money. Helped people.
But it also felt limiting.
I wanted to share what I was learning about AI and automation. Talk about building systems. Discuss insights from my day job leading Business Development. But I'd boxed myself into only talking about communication skills.
Here's what I've learned: Being mission-driven beats being topic-driven for me. Dan Koe’s newsletter issue made that sink in for me.
My actual mission has always been bigger than communication tips. I’m still trying to figure out what my personal brand mission statement is today. But I do know that I’ve always wanted to build a personal brand that can evolve with me. Create content about whatever I find valuable. Build multiple businesses. Inspire others to do the same.
Now with this newsletter Side Hustle Stories, I'm finally aligned with that goal. I can talk about creator businesses, share automation workflows, discuss what I'm building. I don’t have a ton of subscribers today, but I feel like I have the freedom to
If you're starting out, think about your why before your what. What's the bigger picture you're building toward? And then don’t be afraid to create content that shows multiple sides of you early.
4. Quick Wins Can Slow Long-Term Growth
I got caught up in the "$10K month" chase that everyone talks about online.
So I launched a high-ticket coaching program. It worked—I made over $50K in a little over a year. Good money for a side hustle.
But coaching is time-intensive. While I was focused on sessions and client work, I:
Slowed down my content creation
Paused YouTube for over a year
Stopped building scalable products
I was essentially trading time for money—exactly what I'd wanted to avoid by building a creator business.
If I'd stayed consistent with content creation and focused on digital products from the start, I'd probably have a stronger foundation today. YouTube especially is where you build deep trust with an audience, and I gave up a year of that growth.
The coaching income was great. But the opportunity cost was real.
Moving Forward
These aren't regrets. Everything I've done has taught me something valuable, and I'm exactly where I need to be.
But if I could sit down with myself from two years ago, I'd share these four insights:
Start building your email list immediately. It's your most valuable asset.
Hire help as soon as you can afford it. Your time is worth more than money.
Build around your mission, not just a niche. Give yourself room to evolve.
Think long-term from day one. Quick wins feel good but compound growth feels better.
Building while working full-time isn't easy. But it's worth it. And these lessons have made the journey clearer for me.
What's one thing you've learned from building your side hustle? I'd genuinely love to hear about it.
-Preston