Hey! Welcome back to the Creator Economy NYC newsletter, your weekly hit of insights and strategies to help you build, monetize, and scale as a creator.
A couple weeks ago, we covered the work you should do before you bring anyone on. Auditing your time, finding the bottleneck, figuring out whether you need help with the chaos, the craft, or the business. If you missed it, [read Part 1 here →].
This week is the harder part: actually finding the right person, vetting them, getting them onboarded, and not lighting thousands of dollars on fire in the process.
Same three creators back to walk us through it: Corporate Natalie, Dara Denney, and Brandon Smithwrick.
But first, a personal note.
After 130 consecutive weeks writing this newsletter, I'm finally taking the advice we preach around here…
Taylor Cromwell has joined the Creator Economy NYC team. She's been working behind the scenes for the past few months supporting the newsletter, and you'll be seeing a lot more of her work in the months ahead. She's here to help push the mission forward, and I couldn't be more excited about what we're building and the stories we’re sharing.
Alright, let's get into it. And let's get your hires set up.
How to hire as a creator (Part 2)
Knowing where you need help is only part of the process. Actually finding the right person, vetting them without wasting months, and setting them up to succeed? That's where most creators stumble.
Here's what Brandon, Natalie, and Dara learned the hard way so you don't have to.
Step 1: Do the math before you do anything.
Brandon Smithwrick came from the business world before he came to creating, and he thinks about every hire like a CEO would. His core math:
"Time is money. If I can spend $100 to get an hour back, and that hour I can do a brand partnership that's worth $1,000, I'm coming out positive."
That's the test you need to run with any hire. Is the hour I'm buying back worth more than what it costs?
One of Brandon's best hires was an accountant. "Each month they gave me a profit and loss statement and an analysis of the business, and I was able to see things at a high level." That's the kind of hire that tells you whether all your other hires are actually working.
Rates vary wildly across geography, experience, and scope, so don't take a number off the internet. Ask three creators in your community what they pay for the role you're considering. The answers will be more useful than any post… this one included.
🔒 Don’t Fuhgeddaboudit: Before you bring anyone on, write down: the task you're offloading, what it currently costs you in hours per week, what you'd do with that time instead, and what that time is actually worth in revenue or growth.
Step 2: Find people through your network before anywhere else.
Where great hires actually come from: referrals.
When Natalie went looking for her first Brand Manager, she didn't post a job listing. She found Annie through her network, and Annie went on to take every piece of administrative weight off her plate.
Brandon's first manager was his wife. The model itself isn't replicable, but the principle behind it is: people who already care about your success will outperform a cold hire almost every time.
The hierarchy that's worked for the creators we talked to:
Referrals from your creator network. Highest signal. Ask in your group chats, your DMs, your community Slacks. Ask other creators at your level who they've hired and would re-hire. (This is also where being plugged into a community pays — s/o to you guys reading this. Help each other out 🤝)
Specialized agencies. If you don't have the network yet, agencies built for the creator space exist now. Natalie started ExpandVA after running into the wall herself. "VA services were excellent generalists, but they weren't hiring with a content or creator lens. I wanted someone passionate about the industry, someone who would function as a right hand rather than a task list."
Marketplaces (Upwork, Contra, Fiverr). Best for clearly-scoped one-off work — graphic design for a launch, podcast editing, transcription. Riskier for ongoing roles where context and taste matter.
Managers and agents. Almost never come from job boards. They come from introductions, from creators who already work with them, or from agencies that approach you as you grow. If you don't have one yet and you're getting steady inbound, ask a more established creator in your niche who they use, or why to find one.
🔒 Don’t Fuhgeddaboudit: Post in your three best group chats this week or even on social with one sentence: "Looking for [specific role] — anyone you've worked with and loved?" The replies will be more useful than any job board.
Step 3: Trial them. Always.
The mistake creators make: signing a six-month or longer retainer with someone they haven't actually worked with yet.
The fix: a paid 2-4 week trial project with clear deliverables before any ongoing commitment. What that looks like by category:
VA / EA: A week of inbox triage. Specific instructions: flag brand opportunities, draft replies for three categories (intros, scheduling, polite no's), deliver a daily summary by 5pm.
Editor: One or two videos cut against three reference videos you love. Brief them on pacing, music style, b-roll preferences. Compare what comes back to what you'd do yourself.
Brand manager: One live negotiation. Give them an active brand thread, a target rate, your non-negotiables, and let them run point. See how they handle the back-and-forth.
Dara took this exact approach with her EA: "I started her off part time for the first few months, and then when we got into a groove we went full time."
Trials work because they reveal what an interview can't: how someone actually communicates, how fast they respond, how they handle ambiguity, and whether their taste matches yours.
🔒 Don’t Fuhgeddaboudit: Whatever the role, scope a 2-week paid trial with a fixed deliverable. Decide in your head, before the trial starts, what would have to happen for you to make it permanent.
Step 4: Onboarding is where most creators actually fail.
"If my editors or strategists or even my EA does something wrong, 99% of the time I can trace it back to a lack of training, systems, or clarity."
That's not a small admission. That's Dara, one of the more systematic creators we've talked to, saying that when something goes wrong with a hire, the blame usually runs upstream.
Most creators hand someone a vague brief and get frustrated when the work doesn't match what's in their head. That's a documentation failure, and it's yours to own as a founder.
Three things to build before your first hire's first day:
1. A voice file. Especially critical for VAs handling email, comments, or DMs. Pull 10 of your real captions, 5 emails, and 5 DM exchanges. Annotate what's "you" vs. what isn't. Add a list of words you never use. Add the way you sign off. This single doc saves you from rewriting their work for the first three months.
2. Loom walkthroughs. Record yourself doing the task they're going to take over. Don't rehearse, do it the messy way you actually do it, narrating what you're choosing and why. 5-15 minutes per task. These compound: every Loom you make once means a future hire onboards 80% faster.
3. Clear escalation rules. What can they decide on their own? What needs to come to you? What's an emergency? Without this, they'll either over-ask (slows you down) or over-decide (does something off-brand).
And as Dara warned: "Especially for an EA role, accept that you will have some unoptimized time where you're learning how to best work with them."
The first month will feel slower. Give it time. By month three, you'll wonder how you ever did it without them.
Step 5: The mistakes that will burn you.
Before we get into the list, this one from Natalie deserves a moment of its own:
"Hire people who are better than you at the things you're not great at. Every hire I've made fills a real gap in my skill set, and the moment I started treating that as the goal instead of an insecurity, the company actually started to grow."
Read that again. The shift she's describing isn't tactical. It's psychological. Most creators insecurity-hire, they bring on people who won't outshine them in areas where they feel exposed. Natalie flipped that, and her business grew when she did.
A few more patterns we keep seeing, flagged directly by the creators we talked to:
Don't outsource the secret sauce. Varun Rana made this mistake the first time around (we covered it here →). "I ended up outsourcing things that were actually my secret sauce - the ideas, the strategy, the story." Delegate execution. Keep taste.
Don't underpay and expect quality. A $10/hr VA you don't trust is more expensive than a $40/hr VA you do, because you'll spend the difference re-doing their work.
Don't skip the trial because you're desperate. "I just need someone now" is exactly the moment you'll hire wrong.
Don't expect the hire to figure out your system. Build the system first. Then hand them the system.
Steal This Playbook
Save this for when you're ready to pull the trigger:
Do the math. Cost of hire vs. value of the hour you're buying back. If the math is positive, move.
Source through network first. Referrals → agencies → marketplaces → job boards. In that order.
Trial everyone. 2-4 week paid project with clear deliverables before any retainer.
Build the system before they start. Voice file, Looms, escalation rules. Do this even if you're not hiring yet, it's the asset that makes the next hire work.
Delegate execution. Keep taste. Your judgment is what makes the brand. That part doesn't get handed off.
Next event coming soon…
Our next event is slotted for July 22nd, so save the date. RSVP details coming in next week's newsletter.
Two free tools top creators use to keep themselves moving
The Creator Goal Setting Guide (FREE): A simple but powerful document to help you declare who you want to BECOME in 2026. Get it here.
The Creator Accountability System (FREE): Your visual companion for consistent creation in 2026. Get it here.
Thanks for reading. That's it for the two-part hiring guide. Forward this to the creator in your life who keeps saying they need help but won't make a move!
F*ck It, Create It,
Brett
+ With research, interview and editorial support by Taylor Cromwell - a newsletter and creator economy expert and founder of Creator Diaries. Follow Taylor on LinkedIn.
