How My Business Crashed & Burned, My Own Story of Failure

Back in 2017, I was working at AAA (the roadside assistance company) helping with their Google Ads.

Once friends and family found out what I did, a lot of them asked for help or referred friends to me. While my day job was fun, I really enjoyed helping small businesses and solopreneurs make more money by optimizing their paid ads.

So much so that I decided to turn that side hustle into a full-time thing and help those clients.

On May 31, 2017, I left my day job and posted this picture as I walked out the door for the last time.

the photo I shared on Instagram as I walked out of my day job

I had saved up 8 months of expenses just in case things went horribly wrong. And good thing I did, because looking back, I had $400 of recurring revenue – not sure how I thought I was going to pay my bills with that, but here we are.

Luckily, I didn’t need to dip into my savings much after those first few months.

And that first year, in 2017, I made $42,000 from that new business.

I was PUMPED. That was almost as much as my full-time salary from my day job – in 7-8 months!

I kept at it. The following year I made $117k and I was absolutely thrilled. I couldn’t believe it.

In 2019, I made $212k from this little side hustle I had decided to take a chance on. And the best part?

I was doing it as a solopreneur, meaning I got to keep most of that (after taxes and expenses, of course).

At this point, my ego got the best of me. I kind of felt like “How do people even fail at this? Business is so easy!”

And then 2020 happened.

People were staying at home and looking for things to do and ways to start learning new things.

The online course business absolutely exploded. Lucky for me, course creators were the exact people I was helping with Facebook and Google ads.

So in 2020, I made $452,000.

Looking at that number still makes my jaw drop. It was WILD. I felt like I was on top of the world. I was able to pay off my student loans (HUGE) and put more money into my investment accounts.

But my excitement and enthusiasm quickly turned into this:

I resonate with this GIF so much. It’s exactly how it felt. I was burning out so hard and so fast that I didn’t even know what to do.

So I ignored it and just pretended like everything was fine.

And over the next 2 years, my business completely fell apart.

The breakdo venue my business made from 2017 to 2022

I was back to where I started.

How the Heck Did This Happen?

There are a lot of reasons this happened, but there are two main ones I see after reflecting on everything.

Remember that whole solopreneur thing I mentioned? People talk about it like it’s amazing, but that is not always the case.

I was doing everything myself which meant I got to keep most of the profits. But that also meant I was doing the jobs of 4-6 full-time employees.

I was so stressed out, I was watching my business burn down around me, and I didn’t know what to do – I was paralyzed.

I had tried to hire help but I didn’t put time into building out the systems to make it work. I just hoped that their experience with running ads could translate into something good.

Instead, it made things worse and created more work for me.

And the second piece of this terrible puzzle was that I hadn’t been asking for help from peers and people in the communities I was a part of.

Being Afraid of the Ask

I was in communities and masterminds, but I never asked questions or got feedback about how I was managing clients, the systems…nothing.

Here’s what I did, vs what I should have done:

Looking back, I think I was too embarrassed to ask. I felt like I should know everything.

After all, I had grown my business to almost half a million in revenue in just 2.5 years. I’m “successful.”

Wasn’t I supposed to know all of this stuff already?

I realize how ridiculous that sounds after typing it, but it’s true.

Why Don’t We Ask?

Before I dig in here, I want to define what I’m referring to as an “ask.”

An ask doesn’t just have to be asking for advice or help. It can be as simple as “hey, do you want to collaborate?” or “Hey, I think your audience would like this.”

In these examples, I’m not referring to cold emailing random people from a list you bought. I’m talking about those warm connections. People you may have interacted with online, or even chatted with in person. They might even be a close friend.

While I was putting together that presentation, I couldn’t stop wondering why people don’t ask others for help, collaborations, etc.

I came across ​this article​, and it really resonated with my experience. There are 3 reasons mentioned that people don’t ask:

  1. Awkwardness – “I don’t want to be a burden” or “Aren’t they my competition?”
  2. Vulnerability – “Shouldn’t I have all the answers already?”
  3. Assumptions – “They’re so busy, they don’t have time”

Any of those sound familiar?

It can be so hard to put aside your fear of vulnerability or looking stupid long enough to make the ask.

We get so caught up in our heads that we hesitate, and eventually, we don’t ask.

I wish I had been brave enough to ask questions like:

  • Is this what burnout feels like?
  • Have any of you ever been through this?
  • Should I hire someone?

If I had, my business probably wouldn’t have gone down in flames like it did.

While I’m grateful for the way things played out because I started Growth In Reverse after that happened, it’s still hard to relive.

How to Get Rid of the Fear

It’s easy to look at someone “successful” and think they must be over this aversion to asking, but I’d bet they still struggle with it.

Sadly, this feeling doesn’t seem to go away, it stays with us as we grow.

I had conversations with some “bigger” creators this week who were feeling this too. And it’s wild because I look at them and think, “wow, they really have it all.”

I almost think this is a version of impostor syndrome, something most of us experience but it shapeshifts as we level up.

I’m finding that when things feel awkward, it’s only because there is a perceived imbalance of giving to taking. There are ways you can turn those asks into gives – I’ll share a good example next week.

But for now, please remember that most of us experience the same hesitations when it comes to asking.

Entrepreneurship is lonely, and the people you’re thinking of asking might also be feeling something similar. By being the one to start that conversation, you could be saving them as well.

So, that’s the story of how my business fell apart.

As cringe-worthy as it was to share, I hope it’s helpful for at least one of you.

chenell basilio

Chenell Basilio

Chenell is the head writer and reverse engineer at Growth In Reverse. She spends her days researching newsletters, audience growth, and generally figuring out how to help others create better content.

She has an almost useless Bachelor's Degree in Geography, enjoys running, listening to podcasts, and eating guacamole. 🥑

Where I hang out on social media:

8 thoughts on “How My Business Crashed & Burned, My Own Story of Failure”

  1. Hi Chenell,

    Great post! Now, I’m interested in the rest of the story. 🙂

    Once you saw your business burning down, did you try to implement any of the ideas you mentioned — like sharing your work, asking questions, etc.? Or did you close that first business down and immediately start Growth in Reverse? I’d love to hear more about that journey.

    LOVE your newsletter, BTW!!

    • Thanks, Michele! I didn’t. I was too paralyzed to do anything until it was too late. Honestly, I didn’t let myself think about how bad it was until I was prepping for this talk. Very cathartic experience (and cringey!)

      I burned myself out so badly on the client services side of the business that I just had no excitement to try and save it. Technically, the LLC is still around, but it’s just not how I make money anymore.

  2. Thanks for sharing Chenell!

    Yes 100% we’ve all been in this place or are in this place.

    I’m even currently in this place in my job – trying to take my skills and turn them into a system as a manager, rather than a bottleneck where only I can do certain things.

    Learning how to delegate, build systems, train and empower – these are not things “normal entrepreneurs” talk about. Feels like the “systems dudes” have all the systems, and everyone else is just overloaded hustling along.

    Let’s normalize sharing our overwhelm and burnout and helping each other move through it to the next level

  3. As someone trying to start a newsletter to equal (if not, surpass) the growth of those already featured on your hall of fame, the inertia to approach people within the community for me can be crippling – so this was a nice read. Sometimes though, there are people within the community that may not necessarily want to give advice and ignore you or if they do give advice it is incredibly generic or limited or an opportunity for them to upsell you onto one of their courses. Which then feeds of on the assumptions bit.

    I am curious though to learn more about what type of business you were doing that allowed you to generate those revenue streams. Why aren’t you still doing it and why have you not considered pivoting the business by improving the systems?

  4. Thanks for that Chenell, it is not easy to discuss failures when success is the one thing we hear so much about – whether it be true or false!

    There is the saying “fail your way to success” which is true, because the person that has experienced failure (like us) is wiser than the person who hasn’t experienced failure. I say wiser because we have learnt some very important lessons about ourselves and business. Failure and success are at either ends of the “spectrum” so we need both to provide us with a healthy perspective on life – I guess we can’t know true success until we have known failure.

  5. How did the business falling apart look like? Is it that you started getting bad results for your clients to the point of losing them. Or were you burnt out to a point of not wanting to run it again and you let the business go (I’ve done that)?

  6. Thanks for sharing this, it’s not easy. Even knowing you throughout this time, I had no idea. Not that anyone else knows what to do but sometimes there’s value in commiserating (a lot of search-focused content creators have been doing a fair amount of that lately with the updates), it’s a way to share the stress and challenges even if you don’t share them financially as a solopreneur. I’ve always found it cathartic to be able to talk to someone, even if it doesn’t get you any answers. 🙂


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