Plot twist: I was the broken connection.

_THE SHORT STORY_

I hired two people in July. By the end of August, I let them both go.

Here's what I learned from this process, and how you can avoid the same mistakes by focusing on building the right connections: the ones between your vision, your systems, and the people who help bring them to life.

➜ Hey! This newsletter is brought to you by Lauren Gibson. Reply here for Q's (this is my personal email).

. LIFE NOTES .

• The numbers are in—unemployment nears 4-year high. Can OpenAI save us?

• I've been tracking my hours spent online. It's way too fun with Rize.

• “Freedom is not Freedom in the beginning of starting a business”

• I ordered this “timeless watch” 2 years ago… it (finally) arrived last week

_THE FULL STORY_

Back in early July, I'd finally secured a solid MRR. I could hire someone. So I did. Two, actually. My net profit dropped from 97% to 82%.

Both contractors were from the Philippines.

Roxy was hire #1 at 5 hours a week. My business buddy Peter (name changed) worked with and trained her on sales processes. I followed Peter's suggestion and created a ChatGPT bot, trained on my brand voice and résumé, to assist me in applying to Upwork project proposals. Her sole job was to apply to Upwork projects on my behalf. 

I spent the first two weeks learning how to delegate to someone new, and create the right SOPs. Three weeks in, I saw she was applying to one job… per hour. I told her this was unacceptable. However, it wasn't her fault; she was simply following the SOP and the guidance of Peter. She had been working with him for 4 months, and had never closed a single deal for Peter. As this is the point of sales, I reconsidered whether this person would be right for my business. 

“Did I make a mistake?” I thought. Yet I gave her another chance. One month later, I closed 1 deal because of her efforts, and I even gave her a bonus of 5% of that deal. However, I realized her work would not be the main revenue driver for my business. 

Bree was hire #2. She was creative and artistic; however, she lacked the organizational skills required for someone to work 20 hours a week under my limited bandwidth. Early on, I was training her on her strengths: design. I wanted to create LinkedIn carousels and cheatsheets like those.

Yet I realized I was spending too much time with her. Every Monday and Thursday, I was online with her between 9-11pm. My days dragged on into the "hustle” territory of 11 hour computer screentime. I know this was true because I use Rize to track my hours (friends love it try one month free here).

Her designs were increasingly fantastic—but I realized I had not built the systems necessary to maintain one designer at 20 hours a week.

In the startup scene, you often hear that “starting a company is like jumping off a cliff and building an airplane on the way down,” and I fully agree with this. What you don't realize is, when you hire someone, you've then bought into the fact that you could crash them, too. 

As a former laid-off startup employee, that hits. Hard. 

_LESSONS LEARNED_

1. Hiring is not just a goal to achieve. 

2. Hiring is a process that requires careful consideration. Especially because your hires become an extension of you and your business.

3. Hiring happens when you find connection and alignment with your revenue, work, and systems.

Next time I hire, I'm running through these steps:

Step 1: Audit Your Time

“Once you see where your time really goes, the hiring decision becomes clearer,” Brendan, an entrepreneur I met at CreatorHubLive, told me. He runs 17 businesses generating $1.7M/month (seemed like someone I could learn from).

He encouraged me to first create a detailed list of my current tasks. So these were mine in August:

Step 2: Filter With the Right Rules

Brendan shared four philosophies that reframed my thinking on hiring:

1. Pay for Experience Over Training Time
   “It would take me more time to develop someone with your expertise from Georgetown. If you can, it’s better to hire someone with proven experience than spend months training someone up. The extra cost saves you time, which is ultimately more valuable.”

   
   

2. When You’re Maxed Out, Pay More
   “If you’re fully maxed out on bandwidth, it’s cheaper in the long run to pay more for someone who can jump in immediately, and not waste your time with delegation.”

   
   

3. Eliminate → Automate → Delegate
   Before you ever hire, run through this filter:

   • Eliminate: Do you actually need to do this task?

   • Automate: If no, can a tool or system handle it?

   • Delegate: If not, can you hand this off to a human with an SOP?

Step 3: Buy Back Your Time

Dan Martell, the author of Buy Back Your Time, has this philosophy:

Your first hire should be an Executive Assistant (EA). 

Why? Because the job of an EA isn’t to generate revenue—it’s to give you back the hours that free you up to focus on the work that does.

Tim Ferriss echoed this in The 4-Hour Workweek when he said, “if you’re still buried in scheduling, inbox chaos, or admin tasks, you’re not truly running your business—you’re trapped inside it.”

The key lessons from Step 3:

• Don’t hire someone to “make you more money” right away.

• Hire someone to remove the friction in your day-to-day so you can focus on your highest-value work—strategy, sales, relationships, creativity.

• The right assistant pays for themselves by buying back the most precious resource you have: time.

_PLAYLIST_

_REFLECTION_

Letting two people go in the same month was really a mirror into my own subconscious.

What I saw reflected back was someone who thought hiring would win the next achievement award. Someone who, despite preaching about connections, had failed to create the right ones within her own business. 

The hardest part? 

Admitting that I was the broken connection. 

Not Roxy. Not Bree. Me. 

I wasn't connected to my own vision clearly enough to need the hires.
I wasn't connected to systems that could support growth.
And I certainly wasn't connected to the uncomfortable truth that I was creating more problems by hiring, instead of solving them through hiring. 

Here's what I'm carrying forward:

Before I hire again, I need to ask myself the hard questions:

What am I actually trying to fix? → Time? Revenue? Fulfillment?

Am I hiring to grow the team or the business? → Focus on ROI output.

Have I built systems / SOPs yet? → Or am I asking someone to help me figure it out? 

The people we bring into our work become extensions of our intentions. If our intentions aren't clear, the connection breaks.

And maybe that's the real lesson here.

Business isn't just about profit margins and productivity. It's about the quality of connections we create—with our work, our systems, and our hires.

The right hire will come when I've done the deeper work of connecting with what I'm actually building, systems and all.

Until then, I'm learning to sit with the discomfort of doing it myself.

Sincerely,

Lauren and the Connections team

P.S Always include this.