539: When To Hire Help And Where To Find The Best Talent With Toni Herrbach

Podcast: Download (Duration: 43:48 — 50.4MB)

Knowing when to hire help for your business comes down to one rule: wait until you have some revenue coming in, and then outsource the tasks that either drag your mood down or block you from doing higher-value work. My co-host Toni Herrbach and I get this question in almost every coaching call, and in this episode we walked through when we made each of our first hires, what we outsourced, and where we found the people (spoiler: mostly the Philippines).

Most new sellers ask about hiring in the wrong order. They want to hire a Facebook ads manager before they have made a single sale, or a customer service person before they have a single customer. We waited years to make our first hires and would do it that way again, with one exception we cover below.

This is a step-by-step guide on when to hire, what to hire out first, and the exact platforms and processes we use to find help both overseas and in the US.

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Key takeaways

• Wait to hire until you have paying customers or a task is so painful it is blocking you from making the content or product that generates revenue.
• Toni went 2 years and roughly $100K to $200K in revenue before her first Bumblebee Linens hire (embroidery and packing help).
• Toni’s first content-business hire was writers at $25 per article, because the blog was earning $6K to $7K/month in ad revenue and needed 3 to 4 articles a week.
• Customer service is the highest-ROI first hire for most ecommerce sellers because the emotional drain is as costly as the time drain.
• Start overseas (Philippines) on OnlineJobs.ph or a managed service like Intelligencia (formerly Second Office), then move to Indeed for in-person US roles.
• You must be proficient enough in a task to spot BS before you outsource it. Never hire out marketing you have never done yourself.

When should you make your first hire?

You should make your first hire when a specific task is either draining your mood, dragging productivity down, or physically preventing you from doing higher-value work, and only after you have some revenue coming in. Hiring before you have customers is the single most common mistake we see in coaching calls.

The tell is when a task starts owning your day emotionally. Toni describes logging into customer service email and being in a bad mood for hours afterward. Steve describes finger calluses from embroidering after his engineering day job.

Once a task is costing you output on everything else you do, hire it out.

The exception: hire earlier if a task is technically preventing content or product creation. If video editing is why you cannot publish YouTube videos, an overseas video editor is worth the money even before the channel is monetized.

How long did Steve wait to make his first Bumblebee Linens hire?

Steve waited about 2 years and roughly six figures in revenue (somewhere between $100K and $200K) before making the first Bumblebee Linens hire. The role was packing and embroidery help, and it went to the son of a family friend so he could operate the $7,000 embroidery machine in the Chou family home.

The first hire’s job started as packing but expanded to embroidery because Steve hated running the machine at night. He had already spent a full year working an engineering day job, then embroidering after dinner until bed. The finger calluses made the ROI on hiring obvious.

The trust piece mattered. The embroidery machine was fragile, expensive, and inside our house, so the first hire had to be someone we already trusted. He came from a housekeeper’s family, which is how we solved the trust problem before it became a hiring problem.

What was Toni’s first ecommerce hire?

Toni’s first paid ecommerce hire was customer service, because customer emails were ruining her mood every single day. Before that, her kids helped pack orders in exchange for Chick-fil-A milkshakes, but the emotional cost of customer service was what pushed her to hire a real employee.

The trigger was a single Amazon customer complaint about a package with tire marks on the envelope. The customer accused Toni of hating people with cancer because the gift was intended for her sister. When you cannot stop yourself from writing an angry response, it is time to hand the inbox to someone whose business it is not.

Toni first hired one of her adult children for the customer service role. It could just as easily have been an overseas VA, because customer service work is fully remote. The point was getting out of the inbox, not who took over.

Why did we wait so long to hire a dedicated customer support person?

We waited until 2023 to hire a dedicated customer support person at Bumblebee Linens, because email volume never felt high enough to justify a full-time salaried role. Instead we had warehouse employees answering the phone between packing tasks, and productivity was destroyed every time an old lady wanted to chat for 30 minutes.

The dedicated hire lifted warehouse fulfillment throughput back up, freed Jen from ever answering another phone call, and turned out to be worth every dollar. The mistake was thinking a dedicated hire only made sense at 100+ tickets a day. Even at 20 tickets a day, the context-switching cost was higher than the salary.

When should content-business owners make their first hire?

Content-business owners should make their first hire once monthly revenue reliably covers the hire and the task in question is either the biggest time sink in the week or the one blocking new content from shipping. Video editing is the highest-ROI first content hire for most creators.

Toni made her first content hire around 2010 to 2011: writers at $25 per article. Her blog needed 3 to 4 articles a week at the time (a much heavier cadence than today), and even at $200 per month for 8 articles, the math worked against $6K to $7K in monthly ad revenue.

Steve waited far longer, until 2018 or 2019, mostly because he could not quantify the value of a single article. Once the money was clearly there, he treated a fixed percentage of revenue as an “automation fund” and stopped correlating individual pieces of content to individual dollars.

Should you hire a video editor before your channel is making money?

You should hire a video editor before your channel is monetized if editing is the specific reason you cannot publish more videos. A 30-video-in-30-days test with our students showed every channel grew from just doing the reps, so anything preventing more reps is worth outsourcing.

The math: if you are spending 20 hours a week editing, that is 20 hours you could spend filming, scripting, or building the business behind the channel. An overseas video editor costs a fraction of a US editor and takes 3 to 6 months to fully train, but the payoff is a channel that ships weekly.

The second reason to hire an editor early is emotional. If you dread editing, you will unconsciously stop filming to avoid the dread. The math above still applies, but “I stopped making content” is the real cost.

What are the 3 things you must understand before you hire someone?

Before you hire anyone, you must understand your customer, understand the task well enough to spot BS, and have a written expectation of what “good” looks like. Skip any of the three and the hire will disappoint you, regardless of who you hire.

You do not need to be an expert in the task. You need enough baseline knowledge to interview a candidate or agency and detect vague answers.

If you are hiring a Facebook ads agency, listen to 5 podcasts on Facebook ads and talk to 3 friends who run ads before the sales call. Then you can smell BS.

You cannot hire out marketing until you have made a sale yourself. No agency will know your customer better than you do at launch, so any agency you hire early is guessing with your money.

Where should you hire from? Philippines vs US for remote work

For remote work that does not require physical presence, start in the Philippines. We have hired customer service, podcast editing, video editing, and executive assistant roles from the Philippines and consistently found stronger work ethic and lower cost than US remote hires for the same roles.

The tradeoff is cultural and communication. Filipino hires can be reluctant to ask clarifying questions when a task is ambiguous, so heavy Loom-video training upfront is non-negotiable.

Steve maintains a private WordPress site with training videos organized by topic. Toni uses a private YouTube channel with unlisted playlists.

For in-person US roles (warehouse, embroidery, retail), we use Indeed. Temp agencies work but cost 3 to 4x a Filipino hire and about 2x a direct US hire, so we only use them when we cannot find talent through Indeed.

Where to hire in the Philippines: OnlineJobs.ph vs managed services

OnlineJobs.ph is the best direct-hire platform in the Philippines and includes a free tutorial series worth 30 to 45 minutes of your time before you post your first job. It covers cultural nuances, expectations, and templates most first-time hirers get wrong.

For your first Filipino hire, or for e-commerce-specific roles, a managed service like Intelligencia (formerly Second Office) pre-vets and pre-trains VAs on Shopify, Amazon, and standard ecommerce workflows. They also provide a physical office (which matters during brownouts) and verify daily attendance. The service costs more but removes the interview and training risk.

Once you have one trusted VA, use them to help hire the next one. When we hired our graphic designer, our existing VA screened candidates from OnlineJobs.ph down to a final 3, so we only had to interview the top of the pile.

How to hire in the US when you need someone in person

When you need someone in person in the US, hire on personality and work ethic first, because most operational tasks (packing, embroidery, phone support) can be trained. We hire through Indeed for scheduled roles, and we hire directly out of other people’s jobs when we spot someone great.

The tactic Toni uses: if you go to a restaurant, a Chick-fil-A, or a Joann Fabric and someone is head-and-shoulders better than everyone else in the store, hand them your card. Toni’s daughter-in-law was recruited off her Chick-fil-A shift multiple times because Chick-fil-A screens for personality. That signal is real.

Steve pushes back that personality-only hires have burned us at Bumblebee Linens (great people who could not execute the work). The synthesis: personality is necessary but not sufficient. Confirm they can do the work in the first week.

Why training videos beat live training for remote hires

Recorded training videos beat live training because you never miss steps on video, and the hire can rewatch as needed instead of asking the same question 3 times. Steve’s rule: keep Camtasia running in the background any time you do a task you might delegate later.

Steve’s Bumblebee Linens training site is a dedicated WordPress install with videos organized by topic (printer maintenance, embroidery, packing). His podcast editor was onboarded from a single 1-hour Camtasia video that Toni ended up watching too. Toni runs the same system on a private YouTube channel with unlisted playlists (cheaper than paid Loom).

Live training feels faster in the moment but reliably skips a detail you covered in the recording. Steve tried to live-train his wife on the new printer, skipped a step, and she made the exact mistake he had covered in the video she declined to watch.

Common mistakes we see with first-time hires

The three most common first-hire mistakes are: hiring before there is a business, undertraining and then getting frustrated when the hire underperforms, and not paying VAs consistent hours during slow weeks (which pushes them to find a second job and quietly demote you).

Toni’s first VA left after 6 to 9 months because Toni had a slow work period and did not guarantee hours. The VA found a second job, deprioritized Toni, and quality tanked.

The fix is guaranteeing weekly hours regardless of workload once the relationship is established. That guarantee is what buys you their attention.

Steve’s version: have the “if things slow down, you still have this job” conversation up front, and ask for weeks or months of notice if they plan to leave. It is uncomfortable to raise, but it prevents the slow fade.

Frequently asked questions

What should be my first hire in ecommerce?

Customer service and packing are the two most common first hires in ecommerce, because they are time-consuming, emotionally draining, and easy to train. Customer service can be done fully remote (including from the Philippines); packing must be in person.

What should be my first hire in a content business?

For most content businesses, video editing is the highest-ROI first hire because it is the biggest time sink and the emotional dread of editing is what stops most creators from publishing more. Writers are the second most common first hire, especially if you need 2+ articles per week.

How much do overseas VAs cost from the Philippines?

Filipino VAs on OnlineJobs.ph typically cost $4 to $8 per hour for general admin, $6 to $12 per hour for specialized roles like video editing or graphic design, and $10 to $20 per hour for senior executive assistants. Managed services like Intelligencia cost more but include recruiting, training, and office facilities.

Is OnlineJobs.ph or Intelligencia better for hiring in the Philippines?

OnlineJobs.ph is cheaper and gives you full control but requires you to interview, train, and manage the VA yourself. Intelligencia (Second Office) is more expensive but pre-vets and pre-trains VAs on ecommerce platforms, provides a physical office, and handles attendance. Use OnlineJobs.ph if you have hiring experience; use Intelligencia for your first Filipino hire.

Can I hire someone to run Facebook ads before I have made a sale?

No. You cannot hire out marketing (Facebook ads, SEO, email) until you have made sales yourself, because no agency will know your customer, angles, or messaging as well as you do. Agencies without seller-side context guess with your money.

How long does it take to train a new remote hire?

Plan for 3 to 12 months to fully ramp a remote hire, depending on role complexity. Video editors typically take 3 to 6 months to reach independent output. Executive assistants and multi-tool roles can take a full year, which is normal even for full-time W-2 hires in the US.

Should I hire a friend or family member for my first role?

Friends and family can work as first hires when trust matters more than skill (like Steve’s embroidery hire operating an expensive machine in his house), but expect awkwardness if you have to correct performance. Toni has hired her adult kids successfully. If the role is skill-heavy and the personal relationship matters, hire outside.

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