7 Unexpected Lessons We’ve Learned from Running an Online Business

7 Unexpected Lessons We’ve Learned from Running an Online Business

It all started on a balcony in Tamarindo, Costa Rica on December 7, 2012.  Josh and I were a few days away from getting married and mere weeks away from celebrating our first year in business, running our affiliate marketing business together.

The sun had just set (which I Instagram’d), “Roots, Rock, Reggae” was playing in the background and we had just taken our first sip of our second drink.

Things felt…perfect.

As we tend to do, we started brainstorming new projects we could work on.

“Have you noticed how many people have been asking us how we make money lately?” I said to Josh.

He sipped his drink and nodded slowly.

I could sense the wheels turning.

After a few more silent moments of just looking at each other, we had it.

“What if we create a site that shares our story and shows other couples how to build a business online?” I said, progressively getting more and more excited at the thought.

“We could….but, what would we call it?” he asked.

“I don’t know…” I murmured as I took another sip. “OH MY GOD! What if we called it Screw the Nine to Five?! You know, so we can show people that you don’t HAVE to live a conventional lifestyle!” I all but screamed.

He just looked at me, with no expression for what felt like 5 minutes of silence before grabbing his laptop and diving into NameCheap.com.

“That URL is available! Should I buy it?”.

With a few quick clicks of the mouse, the Screw was born.

Sure, we didn’t know what the hell to do with it once we had it, but the seed had been planted and the wheels were in motion.

It’s now been 3 years since we first launched the Screw and it has been one hell of a journey, complete with ups, downs, failures, stresses and massive successes.

And while I’m oh-so-grateful for everything we’ve experienced over the last 3 years, there are a few (okay, 9) things I wish I had known when we first started the Screw.

Lesson 1: Surround Yourself with People Who “Get” It

Fortunately, we learned this one pretty early on, thanks to all the blank stares we would get when we would talk about our “internet business”.

I mean, you can only explain your entire business and answer the question “what will you do if this doesn’t work out?” so many times before you start looking for new social circles full of like-minded people.

In fact, we shot a whole podcast episode around this topic because THAT is how often we’ve had to deal with this.

And I know we’re not alone…

I hear this nearly every week in our FB group from other entrepreneurs who are struggling with feeling understood and accepted by their friends and family.

It’s the whole reason we created our U Crews program (local mastermind and accountability groups) inside of Screw Uβ€”so members would have a network of other committed entrepreneurs to connect and bounce ideas with.

If you don’t already have a group of business buddies, what are you waiting for? Hop into our free FB group and start meeting people, like yesterday.

Takeaway: Entrepreneurship can be a lonely journey. Do everything you can to find your people and foster those relationships.

Lesson 2: Stop Copying Other People

Oh man, this one was big for us!

You see, for the first 2 years of the Screw we followed what everyone else was doing online in the vain hopes it would work for us.

We would say things like…

“Oh, the most successful people do a couple of big launches per year and that’s it? We need to do that!”


“Hmmm it looks like people are doing weekly webinars and selling one-off products…we should do that!”

And even…

“You know, I’ve heard people say that cranking out as much content as possible is the only way to build your business. We better get on that!”

You know what that did?

Left us with a business that didn’t “feel” like us.

Instead, things felt stressful, forced and heavy.

And the minute we realized that we didn’t have to do what everyone else is doing and we could forge our own path and create the kind of business we wanted to run is the minute everything started to click for us.

In fact, we talked about this with Amy Porterfield in this podcast episode earlier this year.

For us, this meant we stopped selling one-off products week to week and went all-in on creating our monthly membership community, Screw U;  which has allowed us to generate predictable revenue in a more automated way, create a sustainable business we believe in and forge a community…no…FAMILY we feel honoured to know and support and love on.

And none of that would have happened if we continued to follow the pack.

Takeaway: Do you. Zero effs.

Lesson 3: If it Feels Heavy, Cut it

We had this ah-ha while on a walk in Florida last October.

You see, up to that point we had been consistently creating content (videos, podcasts, blogposts and pretending to like Periscope) for the sake of meeting an editorial deadline.

But honestly?

It felt heavy to us.

It was no longer enjoyable the way it used to be, we felt stressed by constantly looming deadlines and it wasn’t moving the needle in our business in a measurable way.

So what did we do?

Cut it.

We cut the podcast at the end of 2015 and made a decision to create purposeful content from there on out.

That means the only content we now create is strategic and deep-dive content that focuses on one subject at a time and leads into one of our automated sales funnels.

Purposeful. Enjoyable. Helpful for everyone.

*happy sigh*

Takeaway: When you’re feeling overwhelmed or unsure of a decision, ask yourself: Does this feel heavy or light.

Deep down you always know.

Lesson 4: To Fail Is To Learn

Ahhh yes, “failure”.

It can be scary, disheartening, embarrassing and one of the most important lessons to experience.

And yet, I speak to so many entrepreneurs who are downright terrified to fail.

They want no part of it.

But here’s the thing…

Those lessons?

They are your turning point.

They serve as your ah-ha moment.

They are your sign that you need to course-correct and take another stab at something, but from a different direction.

Hell, looking back on it, our biggest failure (launching a product that no one bought, which we talked about in this episode) still stands out as one of our most pivotal moments in our business.


Because it forced us to realize that we can’t just assume we know what people want, we have to ask them.

And we’ve used that lesson in so many ways to make our business more enjoyable, efficient and profitable.

From polling the members of our free FB group to find out what they need help with (so we can create funnels around it, as we outline in this post) to surveying our Screw U members to see how we can continue to improve the U experience…

Everything we do now is from a place of first-hand feedback, not guesswork.

Try it and get ready to feel an overwhelming sense of relief.

Takeaway: Don’t assume you know what people want, ask them. And listen. 

Lesson 5: Be Consistent and Persistent

If I could drill one thing into peoples heads it would be this…

Building a business online?

It takes patience.

It takes consistency.

It takes persistence.

It takes belief.

It takes sacrifice.

It takes gratitude, even when you feel as though you have nothing to be grateful for…

It takes an understanding that things don’t happen overnight.

It takes time.

Probably more time than you think it should.

So don’t beat yourself up because you think you’re “falling behind”.

Everything has a time and if you stick it out, it will come.

Shit, I remember torturing myself back in 2013 and ’14 because we hadn’t yet reached the coveted $25,000/month mark yet.

I mean, everyone said it was so “easy”, so why weren’t we there yet?

But here’s the thing I didn’t know…

To get to that point?

You need to go through some shit…

You need to get a few bumps and bruises…

And you need some experience under your belt so you can learn the specific systems you need to create an efficient business that allows you the space to work on those 25k-generating tasks.

Takeaway: Stay consistent, be persistent and it will happen.

Lesson 6: Hire for Attitude, Train for Skills

I’m not gonna lie…

Josh and I have made some poor hiring choices over the years.

I mean, shit, it can be hard to find the right people online who are both skilled AND a pleasure to work with.

From contractors who fall off the radar and don’t respond for weeks to service providers who roll with an unspoken sense of entitlement that they are doing you a favour, it can be downright difficult to find that “perfect” person.

So what’s the lesson we learned from all of our hiring hell?

Identify people who possess the kind of attitude and personality you want to work with and then train them on the specific tasks and procedures you want them to manage.

For example, we hired our right-hand lady, Heather (after having her as a Screw U member for 18 months) because we could see how much of a nurturer she was, how closely she paid attention to detail,  always supported other members and consistently rocked a positive attitude.

Then once she joined Team Screw, we took the time to train her on the specific tasks we needed her to take on in her role.

And now?

She’s a pivotal part of the Screw and we simply cannot imagine doing it all without her.

Takeaway: Learn to spot and hire the true stars and treat them well.

Lesson 7: Know Your Numbers

I truly wish we had learned this lesson years ago.

Hell, I wish I learned this in school!

Because here’s the thing…

Knowing your numbers in business is paramount.

And I’m not talking paying attention to bullshit numbers like your email opt-outs, your “likes” or your open rate.

I’m talking the numbers that matter.

I’m talking the heartbeat of your business.


We learned this the hard way when we got slapped with a hefty tax bill in early 2015 and quickly realized that when it came to managing the money in our business? We were clueless.

We just didn’t even know where to start, as we talk about in this podcast episode.

I mean, every accountant we talked to seemed to just spit jargon at us and talk in circles, which left us (especially me) feeling massively overwhelmed at the thought of even THINKING about our numbers.

It all just felt too real.

And then we found the book Profit First, by Mike Michalowicz.


I just…

I don’t even have words for how much this book changed our entire perspective on money.

It was a game-changer.

No, a life-alterer.

Not to mention the audiobook is goddamn hilarious and packed with “holy shit I didn’t know you could do that” actionable (and whip-smart) advice that helps you get real and honest with your money.

You see, so many of us start out in business believing that the system goes like this: revenue – expenses – taxes – owner’s pay = profit.

Whereas the Profit First system suggests we approach it from this angle: revenue – profit – owner’s pay – taxes = expenses.

Essentially, he teaches you how to ensure your business is always healthy, profitable and working FOR YOU, not the other way around.

That way you’re not spending all your money each month because you think the only way to grow your business is to reinvest everything back into it.

If that scraping-the-surface overview made you think “hmmm I could be better with my money” then do yourself a favour and get the book.

After all, there is nothing worse than money stress.

Takeaway: Build a business that works for you, not the other way around. 

Looking back over these lessons I realize how wild of a ride this whole entrepreneurship thang has been…

And you know what?

Even though I’ve had my fair share of moments where I wanted to give up, throw a temper tantrum, convince myself it was “never going to work” and spend the day ugly-crying, I would do it all over again.

Because nothing beats that rush you get when you make an impact in someone’s life.

Here’s to the next 3!

Thanks for reading.

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18 thoughts on “7 Unexpected Lessons We’ve Learned from Running an Online Business”

  1. This is so awesome. I’m totally getting that book and I love that you say ‘just do you’. I feel like there are times I am chasing my tail trying to do what everyone else says to do and it never feels ‘right’. Thanks guys! <3

  2. Awesome! These lessons will come in handy on my journey! So glad you didn’t give up! For that I say thank you! I will also be checking out that book!

  3. all kinds of love for this post. I’m a little partial to #9 (know thy numbers, people!)… but #3 feels pretty damn good too. In the midst of cutting ALL of the heavy out of my business and my life. Sometimes a quickie & quirky confirmation is just what the doctor ordered!

    Thanks so much lady!

  4. Number 3! It’s been the game changer for me. I’ve been constantly living under a guilt cloud of not producing enough content, regularly enough. And when I have? It’s been crap because I didn’t really know WHY I was writing those posts. Realising that posting valuable, strategic content just when it makes sense to my business goals – what a relief! And suddenly…I’ve got tonnes of ideas. Go figure πŸ™‚

  5. Love it Jill and so glad you opened up on all fronts AND that you’re going to take some mental time out as you guys have been on fire. But you also are in that enviable position of so many people looking up to you and to provide that guidance and say yes “Take time out, to create, to get reinspired etc” is so important.

  6. Great post Jill – Thank you for sharing. I especially appreciate your recommendation on Profit First. I’m only into the second chapter but can already tell it is a complete GAME CHANGER. Thank you – your community is amazing.

  7. Online incomes are now earned by people selling courses on “how to make money online” Generally, those courses are paraphrased courses from other courses the presenters have taken online or by attending “mastermind” conferences.

    So, all you guys buying into courses on “how to make money online” by selling something REAL” instead accumulate all the courses and info about selling online and package it as “how to make money on line” course, create the website, get the support group – this is HOW you can make money … in the short-term.

    Unfortunately, this is all going to come crashing down in the future. I live in Ireland and in the noughties, people became millionaires (celtic tiger era)…. selling houses to each other, until the whole thing came crashing down with the CRASH.

    In the not too distant future NOBODY is going to pay for “how to sell online” courses – ALL FREE. It is a good idea to have a REAL product that people want, there will be no problem selling it if you.

    Now guess where this comment is going to go? IN THE BIN.

    All kinds of love!!!!!

  8. Holy moly awesomeness – love these lessons AND the resources you’ve tied to them that have helped you deal with each of these lessons along the way. Always providing massive value!!!… for this, and a million other reasons, we’ve got so much love for you and what you guys do at the Screw! Thank you!

  9. Love you post, Jill – informative and “real life” business experience sharing, not the 6-figure/month kind of sharing πŸ™‚ As a wealth and financial freedom coach, I really appreciate your sharing the PROFITABLE BUSINESS “money formula” and the book! Thank you for this enjoyable read!

  10. Love this post Jill. My favourite is number two, I feel like i’ve been doing this for years, just working and building my biz to try and make it profitable while losing what I want to do and feel is right. Sure I made money… but it feels heavy πŸ˜‰ Excited to see what happens next. Thanks for your support!


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