Why I Quit Substack to Help Build a Generational Startup
And why you should come join me...
In October of last year, I was posting on Substack once a day.
I had grown to a few thousand subscribers.
I was going to PR events every single night of the week — eating complimentary tray passed hors d'oeuvres and cocktails for dinner.
And I was drowning in cardboard boxes from all of the products brands were sending me in hopes I’d give them space in the newsletter.
Then one day — I quit.
Why? I found a new purpose: the opportunity to help scale a generational company. And I want you to (potentially) join me.
First, let’s rewind a bit.
I first started my Substack in November of 2023. I had just moved to New York City and I barely knew anyone. I had a steady remote marketing job at a fintech startup which was hardly taking 8 hours a day to do.
So basically I had a lot of free time and a lot of ambition.
I didn’t move to New York so I could wither away in my apartment all day sending meaningless Teams messages and looking at Instagram wishing I was at the events all the “cool” people were at.
I had no connections to the world I wanted to be apart of and certainly no connections that would help me level up my career.
All I had was a lot of opinions about brands, marketing, and tech that I had no outlet for. And so my first move? Screaming into the void until someone would notice me.
I knew I had to be consistent if I was ever going to make a dent. So I started posting every single day. I’d use the free time I had between leaving Equinox and starting work to write my newsletters, and I’d use my evenings to source stories, digging through social media to find gems.
I dedicated my life to writing the best Substack possible and… it wasn’t exactly a resounding success. I literally had like 50 subscribers for 4 months, all friends and family just subscribing out of pity to me.
That was until Spring of last year — when a few viral posts, mentions in larger Substacks, and figuring out how to crack the algorithm skyrocketed my growth.
For the first time in my life, people were finally paying attention to me. I was getting invited to events, meeting new people in marketing, getting free packages every day— and making money from paid subscriptions.
All of a sudden brands were reading what I had to say and thinking I knew what I was talking about when it came to brand strategy (which I did!) and my consultancy took off!
By Fall, I was making more money than I had in my entire life and the flexibility to work when I wanted. But something still felt missing…
Then I took a call that would change my life.
A recruiter had reached out to me about a job opportunity as a marketing manager at a startup. I was intrigued so I took the call.
On the other end was Will Gao, Head of Growth at Rilla.
He told me they were on a mission to make the world of offline sales as indexable as Google made the internet.
Think about all of the in-person sales conversations that happen everyday. They are currently lost to the ether. But these conversations hold so much value!
Insights on what consumers want, what they’re concerned about, and the secrets to how to effectively sell a product or service. I saw the vision.
As someone who is incredibly interested in bold missions, consumer habits, and AI— I was intrigued. Will told me the median age of the company was 25, they worked 6 days per week, 12 hours per day.
This company was the antithesis of all the bullshit marketing jobs I had ever interviewed for. A culture of young people that worked tirelessly towards a vision to change the world — and to make a fuck ton of money along the way.
When I went into the office I was even more enthralled. I found a ton of young people with exceptional backgrounds — D1 athletes, former founders, and Ivy League grads — packed into a tight office in Long Island City working from 7AM - 11PM every night.
All unconventional people working towards one singular goal: creating the next generational company.
A company on the same level as the giants that came before us.
I knew this was the place I was looking for. Somewhere that valued moving fast, breaking shit, and building a generational company. But I was nervous— did I want to give up what I was building independently to help build Rilla?
A few hours before taking the job offer, I was at the World Trade Center in the GQ office taking photos for a story
was writing about Gen Z workaholics who love Zyn.I asked her to give me her appraisal of the situation and give me some advice. She told me to take the job. It was one of the best pieces of advice anyone ever gave me.
That night, I signed the job offer and got to work. I quit my other job the next day and began the greatest journey of my life so far.
Over the last 6 months of Rilla, I’ve leveled up in ways I never could have imagined. Let me give you an example—
When I joined Rilla, I got told we were throwing our first conference and we had a goal of getting 500 people to come join us in Las Vegas.
It was a huge swing for the fences, and I had no clue how to market a conference let alone sell tickets.
After researching, experimenting, failing, and trying again and again we finally cracked the formula.
3 months later we held the first ever Rilla Masters, and were joined by 1,000 of the top sales pros in the country. We launched our biggest product update yet. And we raced supercars around a track at 150MPH.
One of the best things about working at Rilla — if you’re not failing often you’re probably playing it too safe.
We value the concept of the reinforcement learner, someone focused on failing, learning, and trying again… and again… and again until they solve the equation.
People with unconventional ideas, unafraid of failure, and an unrelenting drive thrive here at Rilla.
In just a few short months I’ve significantly scaled my skills as a growth marketer, have had the opportunity to lead projects I used to dream of, and I feel truly hungry every single day I wake up.
And we have so much fun doing it. I'd argue Rilla is the most exciting place in the world to work right now if you’re want to go far and are willing to put in the work.
If you’re reading this and this sounds like a place you’d thrive in then I have great news.
We’re looking to grow the team.
We’re hiring a Marketing Manager.
You’ll help continue to grow one of the strongest software brands of all time.
We have one of the strongest brands our customers have ever seen.
This didn’t happen by accident.
We think most B2B softwares and products suck. And we think the way they market themselves sucks even more.
Our heroes are the consumer companies that capture attention and deliver some of the most widely used products in the world.
Just because contracts are signed and people have to use software for work, doesn’t mean we can’t put the same level of attention, care, and creativity that Apple or Nike does in their work.
As a result…
We are one of the fastest-growing startups in the world right now and in history.
And we want to add another marketing savage to help us scale to $100M+ in ARR.
Here’s what you should be—
🧠 An infinite learner. Someone who is always curious. You quickly learn new technologies and execute independently. You are a generalist who will deep dive into a challenge.
🔍 A customer obsessive. Someone who deeply cares about delighting customers and solving their pains, not about vanity metrics.
🏆 A superstar. You dedicate your life to mastering your craft and leaving your mark on the world, and want to be around a team that is similarly obsessed with greatness. We work 6 days a week, 12 hour days, because to us, building and defining the future is the most fulfilling thing in the world.
🏅 A quality obsessive. Someone who deeply cares about our users and the quality of their work. Our customers are not tech companies. They’re people who live and work in the real world. To solve problems for them you need to have extreme empathy. You have to understand how they work, what they need, and want, and how to make their lives better.
🤝 A team player. You love giving and receiving feedback, and learning and growing as a team.
📈 Unafraid of failure. You take risks. You see failure as an opportunity to learn, grow, and be better the next time. In a weird way, you trick your brain into being excited when you fail, because it means you got a new opportunity to learn more.
So if you’re tired of your bullshit marketing job and are looking for a place to take your talents and truly grow, then I want you to apply.
Let’s build generational brand campaigns. Let’s figure out new ways to growth hack. Let’s go to war together.
➡️ Apply here
and email me if you have any questions: jake@rilla.com