Scaling with Freelancers & Outsourcing

I’ve been working with overseas contractors now for the past two years to help with this brand and my previous content platform.

We’re witnessing (and all participating in) an outsourcing revolution.

As Western online business owners look to offshore labor more and more, learning how to work with β€” and enable β€” your foreign colleagues is paramount.

In past W2 roles, I’ve been able to work with geographically-dispersed coworkers in cities like Berlin, Vienna, Hong Kong, London, ZΓΌrich, Tunisia, Tel Aviv, Amsterdam, Paris, and Central America. That was a great foray into working with people who didn’t speak English as their first language.

But now, outsourcing to third-world countries is becoming even more widespread as solopreneurs and SMBs, specifically, are increasingly using marketplaces like Upwork, Fiverr and OnlineJobs.ph to find cheap fractional or even full-time help in lieu of expensive U.S. hires.

I’ve been using Upwork for about two years to find freelancers (granted, in a part-time or one-off capacity versus Trent’s strategy in building out his company). Until they recently increased their fees on the client side, I’ve had a great experience finding awesome help on Upwork. But I’ve also made mistakes that I’ve learned from. Nowadays, there’s three things I always ask my contractors before setting up a contract:

  1. Who have you helped in the past with similar work? Show me specific examples of projects you’ve done before most like this one.
  2. What tools or process will you use to do the job? What’s your timetable for projects like this, and what’s your current workload like?
  3. How do you communicate? Will you be sub-contracting this job or using AI after I hire you?

The answers to these questions usually tell me all I need to know to move forward.

And, most of the freelancers I find are literally so eager to work β€” often proactively sharing and begging for more ways to add value for me. They want to work! As a result, I’m a chronic outsourcer. I outsource anything I can’t, shouldn’t be, or don’t want to do. It’s a win-win. The person I hire can and does want to do the task β€” and can do it way better than me given thorough context and instructions.

This frees me up to do more high-leverage, high-impact work.

When looking for quick work, I don’t waste time with phone calls, video interviews, or multi-day back-and-forth texting. I hire quick. Either they can do the job or they can’t.

To give you an idea of the kinds of jobs you might be able to start outsourcing, here’s a snapshot of a string of my Upwork postings from 2022 plus my lifetime spend and volume of posts:

As you can see, I’ve posted over 100 jobs, just over four grand spent, at about $5 per hour. Not a bad way to scale your brand or biz.

If you can get an outsized return from outsourcing, do it. If you can offload mechanical tasks to free yourself to do more value-producing tasks, do it. If you can use freelancers as spokes around your revenue hub, absolutely do it. That’s the whole point.

Outsourcing is economical, easy, and quick. There’s no reason not to be doing it as you look to scale yourself or your business much like Trent did with his agency.

The market is shifting fast. Working with overseas coworkers and contractors is a skill that can be learned, mastered, and integrated as these shifts continue to happen.


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