I Had 10 Businesses. I Killed 9 of Them and Kept Fresh Chile.

I Had 10 Businesses. I Killed 9 of Them and Kept Fresh Chile.

Two years ago I had ten businesses. A restaurant. A winery. A coffee shop. Airbnb, real estate, a magazine, a couple CPG things. Four of them were doing seven figures or better.

And I was broken.

I'll just say it plain because I've said it publicly before. Depression. Mind and body brokenness. My accountant sat me down and told me I should think about filing bankruptcy. Ten businesses, four of them printing real revenue, and that's where I was.

People hear "serial entrepreneur" and they think Lamborghinis. I'm about to tell you what it actually felt like.

Why I broke

It wasn't the work. I love work. I've worked seven days a week for the last seven years on this brand and I'd do it again.

It was that I had no clarity. You know that thing where you're stuck on the same level of a video game and the same beast shows up at the end and you just keep dying? That was me. Over and over and over. Different industries, different problems, same beast.

So I had a real heart to heart with myself. What do you actually love doing?

I love telling stories. I love marketing, and I mean I genuinely love it, which I don't think a lot of people in this industry can honestly say. I love building community. I love connecting with people.

Okay. So where do I do that best? At a restaurant? At an apparel store? Or in Shopify and ecommerce, where the ecosystem and the people have always been the thing I loved most?

I killed nine businesses. Kept the chile.

Hard mode, on purpose

Here's what nobody tells you about the top 1% of Shopify.

We're in the top 1%. Eight figures. And we didn't turn a profit until year six.

Twenty seven million generated. Twenty seven million right back into it. Let that sink in for a second. Any brand doing 50 million in revenue has probably put 50 million back into it. People don't understand those economics.

And we chose the hard version. We built our own manufacturing. We built our own shipping. We're mailing glass jars full of liquid across America and 25% of our sales is shipping alone. Nobody does it this way because it's insane.

We did it because I wasn't going to put out a product I couldn't stand behind. This isn't one supplement versus another supplement where you're arguing about a label. You can physically see the difference. Farm to jar in 24 to 48 hours. Picked this morning, roasted this afternoon, in the jar tonight.

Took six years. Gave me a lot of battle scars. I'd do it again.

The scorecard

About two years ago I started posting my real numbers on LinkedIn. ROAS, ad spend, conversion rate, all of it, every week.

It looks like a flex now. It absolutely was not a flex when I started. The numbers were ugly, baby. Genuinely embarrassing. I had every internal voice telling me not to do it. You're gonna look like a failure. Don't put that out there.

I did it anyway because I needed help.

And Sean from Ridge, Zach, Ezra, they showed up in my DMs. That only happened because the numbers were bad. Nobody DMs the guy who's crushing it.

Then it snowballed into something I never intended. Investors interested in the company. People asking me to speak at events. All of it came from being honest about the part that wasn't working.

What finally flipped us profitable

We cut way back on Meta.

The Shopify business model has you handing Meta a huge chunk of your business, same as app builders handing Apple 30%. They have a moat and they know it.

But here's what we had that a lot of brands don't. Over a quarter million organic followers. A Facebook group of 36,000 people. More engagement than Heinz, Tabasco, Truff, and Cholula. Combined.

So instead of pouring everything into the top of the funnel chasing strangers, we leaned into the people who already raised their hand. The email list. The Shopify segments. The community. Giveaways where we give our own customers cash instead of handing it to Zuckerberg.

This is the biggest thing I can tell you and I don't care what channel you're on. Tap into your existing audience. Everybody's obsessed with top of funnel and nobody nurtures what they already have. They don't nurture what they have.

First profitable quarter in six years came out of that.

If you've got seven tabs open

I sat down with Kurt Elster on The Unofficial Shopify Podcast and we got into all of it. The brokenness, the six years, the scorecard, the whole thing. Kurt asks good questions, the kind that make you actually think instead of just running your bit. He's been in the Shopify game since 2012 and he's one of the few who's genuinely been in it the whole time.

Go watch it, and subscribe to him while you're there.

https://www.youtube.com/watch?v=-t5O_wB5vhw&t=1s

And if you're sitting there right now with seven tabs open across three businesses, you already know which ones are killing you.

Go kill them.