Well, I’ve made it.

I’ve doubted, many times, whether or not I would make it. Other people (but never my mom) did, too. And those doubts were not without reason.

But I’ve proven them all wrong.

Today, as the month of October offers up its last dying breath (happy Halloween btw), it’s official:

I’ve worked full-time for one whole year on this multi-layered mess of a business called Two Story Media.

I feel incredibly blessed by that reality. I also think that it’s crazy.

Most of you know my background story; I won’t bore you with the details of how I built Two Story on the side while working full-time at another marketing agency, or how I finally worked up the nerve to step into this business full-time last fall, or how I single-handedly saved a walrus from drowning while skydiving in Greenland*.

That would be totally self-serving of me.

But I am going to take this email to be just a little bit self-serving.


1) It’s my email and I don’t have a boss to tell me it’s a bad idea, and

2) I think it’ll be helpful to reflect just a bit on what’s happened in this business over the past year.

Mostly this will be helpful for me, but if you’re a person who sometimes reads about things that happen to other people, you might find it a little helpful, too.

With all of that said, here’s what’s happened at Two Story over the past year.

I really didn’t know what I was getting into when I quit my job in October 2021.

I knew that Two Story Media was close to bringing in a full-time income, and I figured that if I actually put full-time effort toward the business, I’d be able to make it work.

But shoot, I cut things pretty close.

For context, at the time I went all-in, here’s how TSM’s income generally shook out:

Affiliate revenue – (commissions from when people click links on my website and then buy a product or service) – 60%

Services revenue – (money that artists pay us in return for services like press campaigns, Spotify promotion, and consulting) – 40%

The total revenue pie came out to a little bit less than what Alli and I needed in order to pay rent, keep the heat on, and eat gluten-free penne pasta.

I had six months of savings I was planning to draw from, but, basically, I had to find a way to increase the business’s revenue or face the prospect of finding a new job fairly quickly.

I opted to focus on increasing services revenue.

The rationale was that, while affiliate revenue is as close to passive income as you can get, it is also 1) not that fun and 2) harder to directly impact, because you grow it by growing traffic, which takes a long time.

With services revenue, you basically trade time for money. In quitting my job, I had more time, so I took on more clients, mostly running PR campaigns and doing consulting. I figured it’d be nice to help more people market their music, and I figured it’d allow me to pay the bills, too.

This worked, but not for long.

I’ve never been great at deadlines, and here I was juggling more deadlines than I’d ever had in my life, trying to deliver for a suddenly-expanded client base without having new systems set in place.

It sucked. I felt like I wasn’t able to do my best work for anyone, because I was constantly scrambling to hit the next release date, and I lived in constant fear that I’d let everyone down.

Unsurprisingly, I burned out fast.

You may not have been able to tell from these emails, but the early spring of 2022 was probably the business’ lowest point.

At the end of the quarter, I stepped back from the haze of constant client work to evaluate how things were going, and I was freaked out by what I saw.

Things were very bad.

I’d blown through half of my savings, and there didn’t seem to be a clear lever to pull that would turn things around. I was at the point where I was considering applying for other jobs. I legitimately felt shame (and fear) at my inability to make a business work; I dreaded telling people that, after all my initial excitement, I’d gone back to work in another office, after all.

Then, miraculously, tax season happened.

And everything changed.

This is a true story that makes me look really dumb, but I’ll tell it to you anyway, and I’ll try to keep it succinct by writing it in a bulleted list.

Here’s why tax season saved my business:

I paid estimated taxes throughout the year of 2021.

  • In April of 2022, I had set aside $14,000 that I thought I owed to complete my tax payments.
  • Despite the fact that I’d never used an accountant because I’m a millennial, I decided to hire an accountant because I was nervous I’d get things wrong.
  • The accountant looked at my books and told me I owed $46 in taxes.
  • I said, “Right, that’s what I thought, fourteen thou… wait sorry come again?” and my eye started twitching.
  • The accountant said, “You owe $46,” and looked at me weird.
  • I magically made $14,000 from one conversation with my new favorite accountant.

I’m not exaggerating when I say that running this business for the past year has mostly felt like straight-up luck.

You know how you feel smart when you set a goal, plan out the ten steps you need to follow to make it happen, and then check off the steps one-by-one to hit the goal?

Yeah, this year has been like the opposite of that. I’ve consistently set goals, planned things out, and then utterly failed – only to get unexpectedly hit in the face by some completely other good thing, anyway.

It’s been a blessing.

Anyway, if I had an editor, they’d definitely be telling me to wrap this email up, and they’d be right. So I’ll summarize the highlights from the rest of the year really quickly.

After my tax season miracle:

June: I cut waaay back on client work.

Since the summer, I’ve decided to only work with a handful of clients at a time – like five per month, max. Life is so much less stressful this way, and I can do better work, too.

July: Affiliate revenue steadily increased as website traffic increased.

It’s insane to me, but we make almost enough from ads for the business to be sustainable without taking any clients (although I’m always going to take clients, because that’s kind of the center of everything).

August: My managing editor of the past three years, Joe, left.

He decided to go to grad school in Scotland (good decision, Joe). I hired Tom (my brother / good writer / outrageously good pickle ball player) to fill the empty position. Having him onboard has been a ton of fun.

September: I launched a course on Spotify growth.

It’s the third course I’ve put out so far (alongside one on branding and one on PR).

Overall, courses have helped to diversify the business’s income streams, and they’ve also allowed us to serve artists without having to overload on client work.

Based on folks’ feedback, I think they’ve worked well.

And that about brings me to today.

It’s October 31st, one year after I left my previous job to work on Two Story full-time.

Again, that’s crazy.

I know it makes business sense to come off as authoritative and confident, but seriously, the fact that I’ve been doing this for a year full-time is completely nuts.

I have no idea what the next year holds. Shoot, I think I have some idea of what’ll happen next month, but I’m probably wrong. For all I know, the business will crash, and I’ll have to go hold the sign for that new carwash on Broadway to make ends meet.

Idk. All I really know is that I’m grateful.

To Alli. To my family. To my friends. To God.

To you.

I don’t take the fact that you read these rambling emails for granted. Thanks for bearing with my self-centered randomness and being along for the ride.

One year down. Who knows how many years to go. Life is wild.

Here’s hoping that something unexpectedly good hits you in the face this week.