The Painful Truth About Hiring Overseas Assistants

I started hiring virtual Assistants nearly 15 years ago.

Since then, I’ve hired all over the world, from here in the US and Canada to the farthest reaches around the world, including India, Pakistan, and the Philippines, to name a few.  To date, I’ve now hired over 700 Assistants.  Some have been a total failure, and some a smash hit.

Early in my career, I thought hiring an overseas assistant was a slam dunk because they were so dang cheap.  When you’re paying only $4/hr, what could possibly go wrong?

Then the headaches started happening.  Big misunderstandings because of the language and culture gap, which meant I had to fix their mistakes over and over.

Then I quickly realized the dramatically different time zones meant it was nearly impossible to meet and collaborate on anything.  This created huge delays that drove me crazy.

Then some Assistants just wouldn’t show up at all.  In one case, my Assistant in India was a victim of government corruption, and the electricity was turned off to her neighborhood.  She was incredible as a worker – awesome English, keen to help, really effective – but that didn’t matter because the environment she was in was so unreliable I couldn’t count on her.

Fed up, one day, I said, “Amateur hour is over!”  I desperately needed a “Mini-Me” type of Assistant who could become my right-hand person, and overseas simply wasn’t cutting it.

So I started looking domestically.  Even though I was stone broke with over $200K in debt and barely making any money – I’d made only $39,000 the year before – I couldn’t stand it anymore.  It seemed unbelievably expensive to pay $15 / hr instead of $4 / hr, but I had to try it.

Within one year of getting a domestic, dedicated Assistant, my income tripled to $107,000, and my productivity quadrupled.  My psychic load was lightened, and I actually started enjoying both my business and my life once again.

As my business grew and I wanted to delegate higher-level tasks such as email inbox and calendar, I realized a domestic Assistant was even more valuable.  Because my Assistant was in the US, I knew I could trust the legal system and the confidentiality agreements I signed with her would be enforceable.  Furthermore, all of my data would exist inside a first-world architecture instead of my most-private information sitting in an unknown office or home in a developing nation where security standards are, how shall we say, “flexible.”


But having a US assistant made it possible for me to hand off these incredibly sensitive yet time-consuming tasks.  Looking back, hiring the right kind of dedicated, domestic, mini-me style Assistant was the biggest productivity jump on my life.  Delegating email and calendar is the second biggest of all time.

I realized: old me thought of getting an Assistant as an expense.  As long as I thought that way, I could never justify getting an Assistant.

But then I realized: even though an Assistant would technically always be an expense, my relationship with an Assistant could become an incredible profit center.  As long as my Assistant was taking over low-level work and I was using that new time to do higher-level, profit-making tasks, I’d always be making way more money than what I spent on an Assistant.

That’s when I realized that being cheap was one of the biggest mistakes I could ever make, and realized I’d only ever hire domestic for the rest of my career.

When it comes to getting a Mini-me Assistant, don’t sacrifice your sanity or the success of your business over a few dollars per hour.  Be smart. Get a Domestic Mini-me. You’ll actually have a shot at fulfilling your potential as an Entrepreneur and as a human.  And that is truly priceless.

Onwards and Upwards,


Properly Training My Assistant Tripled My Income

After I failed with my first five Assistants, I believed training an Assistant was a huge waste of time because they’d just quit.  Plus I could just do it better myself so why bother?

And the math just didn’t make sense to spend 30 minutes training an Assistant on a 10 minute task. I basically gave up on ever getting an Assistant.

Then, one day I was feeling completely exhausted and demoralized.  I’d spent all day working like a madman, yet – ONCE AGAIN – I’d made truly zero progress on my most important projects.

That’s when it hit me that the biggest waste was me.

I was wasting my potential day in and day out dying a slow death, crushed by minutiae of day to day administrative tasks and email.  Something had to change.

So I did a time study, logging every minute of my day. It was an eye-opener. I was wasting so much time on small stuff, while my real game-changing work was on hold.

Reminded me of the age-old quote,

“Hell is meeting the man I could have been.”  

I stared at my time-study and shivers ran down my spine when I realized how much time I was wasting.

I devised a 3 part gameplan which worked perfectly:

  1. Hired a North American dedicated assistant who wanted a long-term opportunity, had the right attitude and work ethic, and was tech savvy.
  2. I found the tasks in my time study which repeated often, were easy to teach, easy to learn, I was already doing myself, and wouldn’t sink the company if done incorrectly
  3. I not only started training, but I DOUBLED DOWN on training my Assistant. Treating her like a long-term investment that appreciates over time.

The result?

Within one year my income tripled and I had more flex time than I ever thought imaginable.

Obviously training the wrong assistant on the wrong tasks is a recipe for failure.

But get the right assistant doing the right tasks and provide them with the right training, and you’ll unleash one of the biggest force multipliers of your entire career.

You’ll also regain the hope that your business is a vehicle to make your dreams come true.

Onwards and upwards

Tim 🙂

3 Ways My Assistant and ChatGPT Supercharge My Business

As an entrepreneur, my journey to managing time and resources more efficiently has been far from easy. 

It’s like juggling balls while spinning plates. 

But here’s a secret weapon I discovered: pairing my assistant with AI, specifically, ChatGPT.

Here are the top 3 game-changing ways we’ve used ChatGPT together:

Content Marketing Magic: 

Content marketing used to be a struggle. From brainstorming topics to keeping a consistent output, it was a daunting task. 

Not anymore. 

Thanks to ChatGPT, my assistant handles a massive part of my content marketing, writing the first draft of all content. Whether it’s emails, blog posts, social media posts, or even speaking points for videos, my assistant creates them all, with ChatGPT by her side. 

The result? 

High-quality drafts that are 65 – 85% perfect, needing only my final touches before they get published to various platforms.

Navigating Sensitive Correspondences: 

Every entrepreneur knows how critical delicate emails can be. A misstep in communication can lead to a crisis. 

Here too, my assistant leverages ChatGPT to craft well-written and empathetic responses, whether it’s a complex legal matter or an upset customer. The result is more effective communication, a speedier response, and with fewer risks.

Demystifying Long Client Messages: 

Consulting often means long emails and reports from clients seeking advice. It can be overwhelming. 

But not with ChatGPT! 

My assistant runs these lengthy messages through it, producing neat summaries and key points. Even better, ChatGPT helps us generate creative and useful replies, often adding new insights that I hadn’t thought of. 

This AI-Assistant partnership has truly elevated my business operations:

My assistant has become a higher-level operator, taking on specialist tasks like content marketing.

It’s streamlined my own time, elegantly summarizing complex situations and facilitating clear communication.

It stimulated my creativity. 

The interplay between my assistant and ChatGPT yields fresh ideas that I hadn’t considered.

In conclusion, if you’re an entrepreneur earning at least $100K/year, an assistant can dramatically enhance your income, impact, and happiness. 

And if you pair that assistant with ChatGPT, you open up a whole new world of productivity. AI doesn’t just supercharge your assistant; it supercharges you. 

Welcome to the future of entrepreneurship

Overcoming the Fear of Losing Control With an Assistant: A Guide for Entrepreneurs

Ever felt that heart-stopping fear of losing control when you think about hiring an assistant?

You’re not alone. 

But here’s a twist – hiring an assistant could actually mean gaining control, not losing it.

Think of your business as a child. Just like the best parents need babysitters, your business needs more hands and minds to thrive. An assistant provides just that.

When you delegate, you’re not losing control. Instead, you’re pinpointing your focus on what truly matters – the big picture, the strategic vision, and the real growth drivers that allow your business to scale.

Here’s how to take this crucial step:

Start small.

Delegate less critical tasks first, and gradually expand their role.

When I first started, I gave my Assistant the task of writing podcast show notes. If they messed up, it didn’t ruin the business. Little by little I gave my Assistant more ownership and trust towards handling bigger tasks/projects.

Later on in our relationship, my Assistant was planning in-person events and came within 2% of the budget that I gave her. 

Don’t think of your assistant as just a “task-doer”. They’re a strategic partner. As this relationship develops, you’ll see your fear start to fade while your confidence starts to soar.

So, it’s time to break the fear, let go of your need to control, and watch your business truly thrive. 

Remember, you’re in good company. Many successful entrepreneurs have walked this path before you. 

Now it’s your turn!