From Employee to Entrepreneur: The First 90 Days Unfiltered

Jordan Ellis

Right—so you're at your desk, scrolling through your notes app, thinking, “Maybe this is The Big One. The idea everyone will need. Or at least pay me to build.” We've all seen those “overnight success” stories, but honestly, before you so much as update your LinkedIn headline, you gotta pressure-test that idea till it squeaks. And I mean, really look it in the eye and give it a bit of side-eye.

Jordan Ellis

I see so many folks jump straight into building—like they’ve watched a couple Silicon Valley montages, gotten a bit giddy, and started coding or ordering business cards. But, look, the first checkpoint is customers. Have you asked anyone, outside your mum, whether this solves a real problem for them? Customer interviews, yes—even if it’s awkward sending that cold message or cornering friends at the pub. The best early wins always came when I trusted actual feedback.

Jordan Ellis

Truthfully, minimum viable product, MVP, it's just a fancy way of saying: “How can you test if people care, without spending a year and your savings account to find out?” I once tried to start an online tutoring side hustle over a summer—set up a kind of snazzy landing page, roped in two mates as tutors. Zero traction, unless you count the one spam inquiry from someone in Canada. Turns out, I’d built something I wanted, not what actual people needed. Classic case of building in a vacuum.

Jordan Ellis

See, it’s tempting to chase trends you see online, or what’s hot on TikTok this week, but the best businesses—honestly, the ones that survive—almost always start by solving a pain that someone’s actually moaning about. Or even better, something you’re slightly obsessed with fixing yourself. Those are the ones that pivot early, adjust to what people tell them, and aren’t afraid to admit, “Alright, this wasn’t quite right. Let’s tweak.”

Jordan Ellis

So, before burning your bridges, test in the real world. I learned that the hard way, juggling a failed online tutoring gig, a short-lived backyard dog-walking service, and a T-shirt idea that, ehh, flopped because I was basically the only one who wanted it. Hobby versus business—that lesson cost me several boxes of unsold shirts, but it stuck.

Jordan Ellis

Funny thing is, even if your idea is solid, your brain will start plotting against you at the worst possible moment. Like, 2 a.m., lights off, convincing yourself you’re a fraud and everyone’s gonna spot it. Imposter syndrome, yeah? It’s like having a heckler living in your head rent-free.

Jordan Ellis

If you listened to our very first episode about budgeting, you might remember me admitting I panic-proofread my own spreadsheets more than once. That same self-doubt follows you into entrepreneurship—only now there’s money, reputation, maybe your mortgage riding on your decisions. So how do you push through? I’m not gonna say “just be confident” because, honestly, I’m still figuring it out myself, but here’s what’s helped.

Jordan Ellis

First off, small wins. They matter, they really do. Celebrate that first email reply, a positive review, even completing a tedious bit of paperwork. Each one adds invisible bricks to your sense of “I can do this.” And then, assemble your support squad. I don’t mean just family who'll cheer you on regardless, but paying attention to those few friends or mentors who’ll call you out—and cheer you harder when you get it right.

Jordan Ellis

Oh, and stumble early. If you tuned into our episode on building your first investment portfolio, you know I’m a firm believer in learning by doing—and sometimes failing for real. My first ever podcast pitch, back in the old office days, was epic in the worst way. Clicker wouldn’t work, my hands literally shook, and I think I called my boss ‘mum’ by accident. Survived it, though. Learned way more from that flop than I did any business book.

Jordan Ellis

If you’re spinning yourself up with doubt, just know: if you make it to morning and send one email you were scared to write, you’re doing the thing. That’s already further than most.

Jordan Ellis

Now, about those first 90 days. It’s like being dropped in the wild with just a pocketknife and packet of crisps—how long can you go before you need rescue? The answer’s in the numbers. Seriously, before even printing your business cards, figure out your personal runway: How long can you pay rent and eat—realistically—before this thing needs to pay you back?

Jordan Ellis

Everyone imagines big spreadsheets and wild forecasts—honestly, most of it’s fiction at this stage. Focus on what you’ve got, what you absolutely need, and what you can live without. Hey, like we talked about in the budgeting episode: find where your money's actually going. Track cash flow—actual ins and outs—every single week. Fancy tools or not, it beats guessing where your cash disappeared to.

Jordan Ellis

One ‘hidden cost’ I wish someone told me sooner? The time you spend chasing invoices, sorting taxes, or learning to write off printer ink properly. It adds up fast. Budget for it. And don’t be shy about negotiating with vendors or even your own landlord if you’re renting office space. Got to stretch every pound.

Jordan Ellis

I know a new solopreneur who kept her freelance gig going alongside her marketing service for six months—effectively, her side hustle was the safety net so she could gamble on the bigger dream. Sometimes, it’s about keeping a little income trickling in so you’re not making decisions out of sheer panic.

Jordan Ellis

Here’s my best bank-teller tip for anyone starting from square one: open a separate account for your business, even if it’s just a no-frills checking account. Keeps you honest, makes taxes easier, and, trust me, it’s less stressful than untangling mixed-up personal and business expenses after six months of receipts crammed in a shoebox.

Jordan Ellis

Okay, that’s a lot to chew on for one episode. We’ve gone from stress-testing ideas to surviving the 90-day gauntlet—not always pretty, but it’s real talk. If you’re still here, you’ve already beat the odds most people never even challenge. You’ve got this—and I’ll see you next time as we tackle what’s next for your CEO journey. Take care.