I made a decision

It's been a long time, I know.

I think this is the longest I have gone without publishing a newsletter since I first started this little experiment back in 2022.

So what happened?

I moved across the US, from NYC to LA. And then I moved to SF.

I went deep into software development, joined a coding bootcamp, and lived inside Cursor and Claude Code every day.

I built an SEO app that is probably my favorite tool I have ever used.

I use it every day, and it has gotten amazing results for a client.

Besides that, I applied to Y Combinator for said SEO app.

I got rejected.

They did say I was in the top 10% of applicants, but maybe that’s just cope.

After that I sorta just didn't know what to do.

I got this crazy high from building for almost 3 months and it was all I wanted to do morning till night. I really had nothing to say or write about. And I knew if I forced it, I would just be creating slop for the sake of being "consistent" as a "content creator." Yuck.

Then more rejections kept popping up.

A huge client ghosted me a day before our kickoff call. Then, a falling out with another promising company.

I didn't know what was going on. I guess when it rains, it pours. Or whatever the saying is.

I felt like my career was at a crossroads. And I didn't know what to do.

So I prayed about it.

I realized I kept looking for places I wanted to be in. Not places that already wanted me.

A product I had been using for the past 18 months kept coming to mind.

It’s called Gumloop, founded by two young Canadians. I started using the tool a lot to build agents that would automate parts of my SEO service delivery, and even for the Marketer Milk website (I have an admin agent that updates the homepage every weekday with content I feed it).

Something felt different about Gumloop. While the tech industry is glazing Claude, there are so many smaller startups that are making me go “wow.” And Gumloop, when used to its full potential, feels like magic. I haven't felt this way about a piece of software since I joined a tiny startup called Webflow early in my career (and that company later became a multi-billion dollar unicorn).

And for the past 6 months, Gumloop became a client of mine. As time passed by, Max, their CEO, asked me to join full time to lead marketing.

I resisted hard.

Some sort of ego of having left the tech scene 4.5 years ago to be self employed would not let me go back in-house.

So I kept praying.

I came to the conclusion that I will always be stuck in limbo if I am afraid to make a decision. The worst thing you can do is not making the wrong decision. It is being indifferent and doing nothing about it.

There is a famous Naval Ravikant quote came to mind. It goes something like, "success comes from good judgement. Good judgement comes from experience. And experience comes from bad judgement."

I started to feel this peace that whatever decision I make, I can't lose.

And this forced me to create a mental model for how I make decisions. It has nothing to do with what "feels" right. In fact, feelings are the worst way to make decisions. Above all, the heart is deceitful.

The mental model came down to one question.

Which path will expand me, cause me to grow, and allow me to be in service of others?

Funny enough, it’s often the path that makes your stomach churn a bit.

I again looked at where I was already being valued. Where people wanted me.

I had an opportunity right in front of me to lead marketing and growth at a fast growing AI startup in the heart of the AI capital of the world.

Meanwhile, I was worried about losing my "self employed" identity and my "freedom" of working from my laptop whenever I wanted from whatever cafe I felt had the right vibe that day.

But the reality is the past 2 years my path had become comfortable. SEO as a skill had allowed me to cruise through life and not worry about being employed (truly a blessing).

But with too much freedom came a waning sense of purpose. Which eventually lead to confusion. Which lead to misery.

So I made a decision.

I packed up my stuff into an SUV and drove to SF. And as of writing this, I am now leading growth and marketing at Gumloop. My day to day involves leading growth initiatives, planning launches, and working with an amazing team to help working professionals in tech experience the magic of creating AI agents.

This next role is not about money or status or my ego.

It is about being of service as best as I can. Putting myself in the chaos that is startup life in San Francisco, and documenting my life as a marketing leader. I will talk about everything from my challenges as a leader all the way to the nitty gritty of marketing tactics.

In the end, the last 4-5 months have taught me that identity really is a crutch. The version of yourself you are protecting is often the exact thing keeping you stuck.

And if you’re at a crossroads, see which path expands you and which path contracts you. If the expansion path also scares you, and gives you a little imposter syndrome, you will know it is the right one.

So far, being back in SF has been quite the ride. And I’ve seen so many amazing startups pioneering the future of work. Outside of Gumloop, there’s an interesting one I linked in the “website of the week“ section below.

With that, let's get into what we have in store this week (lots of good stuff):

• Marketing news from the past week

• Improving free-to-paid conversion

• How to write your first 10 newsletters

• An LLM recommendation content strategy

• Dropping cost-per-lead from $250 to $25

• Ad in the wild

• Website of the week

• Cool marketing jobs

• And much more

🗞 In the news

• 68M AI crawler visits show what drives AI search visibility

• Meta threatens to withdraw its apps from New Mexico

• The state of generative AI in the creator economy

• As workers worry about AI, Nvidia’s Jensen Huang says AI is ‘creating an enormous number of jobs’

🚀 All things growth & product

 🤖 AI, emails, & copywriting

✍️ SEO & content marketing

🤳 Social media, paid ads, & branding

📣 Ad in the wild

Clever copywriting I spotted the other day.

💻 Product of the week

Stealth startup founded by one of the smartest people I know in tech. Got the founder to open it publicly only to subscribers of this newsletter (so keep it on the DL). You can use code MARKETERMILK for 50% off if you decide to use the paid version.

🏝 Cool marketing jobs

• Growth @ Numeral

• Product Marketing Manager, Builder Audience @ Figma

• Product Marketing Manager, Codex @ OpenAI

• GTM Growth Lead, Advertising @ G2

• Head of Growth Marketing @ Writesonic

Okay, that's it for now 💙. See you in the next edition!

“True humility is not thinking less of yourself; it is thinking of yourself less.” ― Rick Warren

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