“I actually started hiring from day one.”
Abbey Ashley says it almost casually, like it wasn’t a big deal. She was six months pregnant. She’d just landed her first client. And instead of waiting until her business felt more stable, more proven, more “ready,” she brought someone on to help her do the work.
Most of us do the opposite. We tell ourselves we’ll hire once we hit a certain number, once we’ve proven we can handle it all ourselves first, once it feels safe. Abbey never bought that story, and it’s why her business, The Virtual Savvy, doesn’t run through her alone.
That’s what this week’s episode of The OBM Show is about: the solopreneur era every CEO eventually has to grow out of, and what it actually takes to let go.
Click here or on the preview below to watch now:
Prefer to listen? This episode is also available as a podcast on the OBM Show Podcast here.
The Lie That Keeps CEOs Stuck Doing It All
Abbey is honest about the story a lot of business owners tell themselves: that hiring is something you earn the right to once you’ve hit some invisible milestone. Prove you can do it alone first, then bring in help.
She rejected that from the start. Not because she had extra cash sitting around. Because she saw hiring as a capacity lever, not a reward. If someone else can do a piece of the work, even imperfectly, even for a few hours a week, that’s time and energy she gets back to spend on the parts of the business only she can do.
If you’re still telling yourself you’ll hire “when things settle down,” Abbey’s story is a pretty direct answer to that: they won’t settle down on their own. You settle them, by handing off what doesn’t need to be you.
The Math That Actually Makes Delegation Make Sense
Here’s the rule Abbey uses to decide what a hire should cost her: stay around 30% of what she charges for the work being outsourced. If she bills $60 an hour for something, she’s comfortable paying someone else up to about $20 an hour to do it, and keeping a healthy margin in between.
Sarah puts the same idea more bluntly: if someone else can do the work, and you can pay them less than what your hour is worth, you’re not spending money by hiring. You’re scaling by outsourcing.
That reframe matters, because most CEOs who are stuck in their own solopreneur era aren’t stuck because they can’t afford help. They’re stuck because they haven’t done the math.
What Actually Predicts Whether a Hire Works Out
Abbey pays for a test project before every hire she makes. Not a portfolio, not a reference check, an actual piece of the real work. “So much is revealed,” she says. The candidates who looked identical on paper suddenly aren’t.
She also builds in a 30-day trial for every new working relationship, on purpose. Not because she expects it to fail, but because it gives both sides permission to be honest early, instead of quietly gritting their teeth until month three.
And when a hire isn’t landing, Abbey’s first question isn’t “is this the wrong person.” It’s “have I actually given them clarity.” The people who get things done, she says, need one thing above everything else to do it well: clarity on exactly what “done” looks like.
The Next Step
If Abbey’s story has you looking at your own business and wondering what you’re still holding onto that you don’t need to be, our Directory of Accredited OBMs is a good place to start. Every OBM in it has been vetted by our team, and our Matchmaking service will personally help you find the right fit for how you actually run your business.
Explore the Directory or start a Matchmaking conversation
If you’re the one reading this thinking you’d rather be the person business owners hire for this kind of work, the OBM Accelerator is a good place to start.
