Why I'm Creating Side Hustle Stories On Substack
The Pivot I Didn't See Coming
Welcome to issue #1 of Side Hustle Stories. Each week, I share honest lessons from building a creator-led business while balancing a FT job and family life. 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.
In August of 2022, I posted a single video on TikTok helping people communicate better at work.
That one video changed everything. It took me 2 hours to make, has just 200 views as of today, and looking back on it today sounds atrocious.
But I loved making it. I loved that I could teach a topic that I cared about and help people from around the world. One video a day became my commitment. And after doing this for roughly a year, one of my videos blew up to 3.5M views.
Slowly, I built an audience: 375K on TikTok, 268K on Instagram. All of it during early mornings and late nights while still leading Business Development full-time at a software company.
But as the content gained traction, I leaned deeper into coaching. I started with 1:1, then launched my first cohort-based program in 2023. High-touch, high-value, high-effort. And while I loved the teaching, I couldn’t shake the feeling: I’m still trading time for money.
I kept telling myself this was a short-term sprint. I just had to do it long enough to build a coaching program that scaled. I even wrote out my ideal life 10 years from now: waking up in a peaceful home, spending unhurried mornings with my kids, building a few businesses I love, tinkering with tools, recording the occasional video, and working deeply but with spaciousness.
But somewhere along the way, I got stuck.
I felt boxed in by the very brand I built. People called me “Coach.” Every video, every product, every coaching offer was about workplace communication: leading meetings, speaking with confidence, getting buy-in. Important stuff. But only one slice of who I am.
What about the systems I’d been quietly building to automate content? What about what I’ve learned from growing on TikTok and IG? What about the software ideas I want to launch that solve real problems for creators and professionals like me?
I wanted to share all of that. But I didn’t feel like I could. Not with the current brand. Not without confusing people.
Then came this last launch.
I opened the third cohort of my Impromptu Speakers Academy hoping for 30 students. But I got 9.
(Side note: I’ll dedicate an entire post later on my launch flopping. But tldr — I believe the marketing should have been better. The program itself has been really good.)
And at first, I panicked. Below is a post where I crowdsourced feedback from The Lab (Jay Clouse’s community, highly recommend it) based off my failed launch.
Should I refund them? Cancel the whole thing? Start over quietly?
But after reflecting deeply and polling the community, I decided to run it.
Because this isn’t a failure. It’s feedback.
We’re currently two weeks in, and the small format is allowing me to over-deliver. Students are loving it. I’m getting valuable input into my self-serve course. And I’ve been reminded why I love teaching. I’m so glad I’m following through.
So I realized this cohort isn’t a detour. It’s a bridge.
Here’s what I’m doing now:
I’m treating this live cohort as the key step in refining my self-serve version of the ISA
I’m repurposing course teachings into modular content using automation tools I’ve built
I’m sharing more of my broader journey: automation, writing, systems, personal growth
I’m expanding the brand to reflect more of me, not just "the corporate speaking coach"
And that’s why I’m launching Side Hustle Stories on Substack.
This will be my weekly outlet to document what it actually looks like to build a business around your personal brand while working full-time. I’ll be sharing the behind-the-scenes of my experiments, automation builds, creator lessons, and the mindset shifts I’m going through as I scale a business that reflects all of me—not just the communication coach.
Every week, I’ll write to help one specific kind of person:
Someone who is where I was 2.5 years ago. Someone who’s in a demanding full-time gig but dreams of building something of their own. Someone who wants to create content, build community, launch digital products, and grow a business around what they know—without burning out or waiting for permission.
My whole life has been one long side hustle:
At Stanford, I ran an SAT tutoring business for my high school peers.
At the NBA in 2016, I built an employee experience app that connected coworkers through shared interests.
From 2019–2022, I built an AI-powered public speaking coach for remote teams—while getting my MBA at MIT Sloan.
And now, I’ve grown a communication content brand with over 600K followers while leading partnerships at a fast-growing software company.
Every step of the way, I’ve built in the margins. Not because I had to. But because I’ve never wanted to be fully defined by my day job.
That’s what Side Hustle Stories is about. The real stories behind what it takes to:
Build a personal brand that can scale
Stay consistent when no one’s watching
Create systems that buy back your time
Grow a business rooted in your values and vision
If you’re a creator, coach, builder, or professional who dreams of doing something bigger with your voice and your skills—this is for you.
This pivot isn’t about leaving communication behind. It’s about integrating it with everything else I love: automation, storytelling, product thinking, content creation.
So if you’re new here: welcome. If you’ve followed my journey so far: thank you.
There’s more to come. But it’ll be more me than ever before.
See you next week.
—Preston