How I Anonymously Launched A Newsletter While Keeping My Day Job [$3K/Month]

Published: June 29th, 2022
Founder, BowTied Opossum
BowTied Opossum
started July 2021
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Hello! Who are you and what business did you start?

Hello, my name is Opossum and I’m the founder of BowTiedOpossum. Did that first sentence confuse you? Well, you’re not alone. We’ll get to that later though.

Many people online choose to be anonymous for a variety of reasons. Chief among those is being able to speak freely and operate side hustles without fear of spillover to their “IRL” careers.

So, what’s my IRL career? I’m a junior/baby eCommerce exec at a brand you likely know. An operator/mechanic of digital businesses if you will.

Most of the online advice about starting a digital business is extremely vague or is written by charlatans. The first is unhelpful while the latter is misguided and damaging to your expectations, energy, the industry, and ultimately your business.

The first end of the spectrum is vague advice. This comes in the form of “just build a website”, “just run ads”, etc. followed by Tweets of “I make so much money, it’s easy bro”. Then there are the screenshots of Shopify stores with good numbers with no defined path of how they got there.

These screenshots may or may not be doctored with the hopes that you’ll buy their digital course that only has 3 copies left…

Speaking of charlatans. There’s an entire industry of advertising/eCommerce/SEO agencies started by people that have barely an ounce of real-world experience. They’re advising clients that don’t know any better. They’re pumping out ill-informed content on their website for the newbie to read.

These charlatans are what give marketing and digital businesses a bad name. These were the people I read when I started years ago.

Today, I run a Substack (paid newsletter) teaching others what I’ve learned from running digital businesses for large and small corporations, consulting, and my projects. Hint – It’s not what the Gurus are telling you.

After 9 months, I’ve managed to grow the newsletter to $3k a month in between my career, outside consulting, personal projects, and family/kids. I’ve done this completely anonymously with 0 ad dollars, by myself, and no prior social media presence to give it a boost.


What's your backstory and how did you come up with the idea?

I built my first digital business at 24 \for\ my father while I was a mechanical engineer. He had an idea and he didn’t know how to sell it. I wanted nothing to do with it, but for him, I relented. I stood up the site and started marketing the product. I had no clue what I was doing but I read a lot and put in the hours.

I can’t say what it was, but before too long, I was on track to do $100k in sales. Then my father’s health started to deteriorate. I didn’t want to take over the product side so I shut it down.

I then forgot about digital businesses for a few years until I started building affiliate sites. Then helping contacts set up and market websites for their small businesses.

Here’s where it starts to get interesting. For the first half of my career, I was an engineer with a security clearance. Through an interesting turn of events, I ended up in an eCommerce department.

Due to the security clearance and my tendency to be a private person, I stayed far away from social media for the most part.

Just get to work. Start building. The more you work and fail, the closer you’ll get to success.

One day I was Googling something and ran upon an article on The website was very blunt and made a lot of sense. I clicked on their Twitter. That made just as much sense. I then signed up for Twitter for the first time.

(Stay with me – the backstory is important)

A year after covid hit, Wall Street Playboys changed their name to BowTiedBull. They saw the destruction that was done to the economy, small businesses, and people’s livelihoods. They wanted to create a community where they could utilize their 100k+ followers and promote people with talent. A community that was “equal opportunity, unequal results”. If you put in the work and showed that you had talent in your domain, they would help give your account exposure.

One of their core tenants is that online businesses are the future. This point is hardly debatable. After seeing bad advice on the internet for years, I decided to throw my hat in the ring and become a BowTied Twitter account. As every account is anonymous, there was no downside in the chance that the account didn’t grow. Only upside.

At the time, all of the BowTieds were animals. I picked an Opossum due to a lack of animal names available and one of the animals that were around on my farm growing up. Opossums are also viewed as a varmint. Which is how many people in Corporate America initially viewed and treated me as a very unpolished farm boy from [redacted].

Take us through the process of designing, prototyping, and manufacturing your first product.

Zero processes at first. Just an anonymous email account and a Twitter account. I started to interact with the community and Tweet actionable advice about eCommerce. No platitudes like money Twitter does. I just Tweeted what I had learned over the years and answered people’s questions.

I remember the night that my account “took off”. I had Tweeted a thread and tagged BowTiedBull. He/they retweeted it. At the time, I had every like/comment/retweet notification turned on. My phone would not stop buzzing. I jokingly texted my wife that I thought I had become internet famous.



I went from something like 110 followers to a few hundred within a day. At this point, I knew that there was a need for actual advice vs the platitudes that you normally see.

I had a website that I had started a year prior about Google Data Studio with about 30 posts. I had run out of ideas for content but it was pulling in a consistent 3k visitors per month. I quickly bought the domain and swapped out the domain names and put in the 301 redirects.

From there I started writing some howto guides about how to get stood up. My traffic started to surge from Twitter every time I posted a new guide.

At this point, I made a conscious decision. Being an anonymous Opossum and helping people was fun and very rewarding but it was taking up too much time from other projects. I either had to take it seriously and monetize it or quit.

I decided to turn it into a paid newsletter. I signed up to Substack and decided to write guides on how to get started and the fundamentals of understanding digital businesses.

Describe the process of launching the business.

Launching on Substack is extremely easy. The real beauty of it is that they make it simple for the user to sign up. It’s analogous to Amazonwhere the user experience makes it easy to buy and has a lot of built-in traffic. The key is getting in front of those users.

In my mind, the difficult part of a newsletter is what are you going to write about as you grow. I want \all\ of my readers to walk away having learned something that’s going to help them. Every. Single. Week.

I didn’t want to be another newsletter pumping out whatever random thought they had or regurgitating someone else’s thoughts. The emails have to be insightful or actionable.

Since launch, what has worked to attract and retain customers?

From a retention standpoint. Talk to your customers. Period.

My niche is very customer-centric. I’m trying to help them succeed and understand concepts that are foreign to them. At least half of my Tweets and posts are ideas I got when I was talking to them. If one customer has the issue, a lot of other people likely have the same issue.

You can waste hours/days analyzing, thinking about, or reading about something that doesn’t matter to your overall goals. When you find yourself doing this, take a walk to regroup your thoughts and action plan.

From an acquisition standpoint, Twitter has been my #1 driver of subscribers. Twitter is a text (vs visual) driven social platform that has the type of people that would be interested in my content. I’m sure I could get good traction on YouTube but my visual editing skills are lacking and I prefer the written word better than videos.

Another very underrated acquisition strategy is being involved in communities. This is the case with the BowTied community. It helped me get off the ground which is the hardest part in my opinion. I won’t go into my other ventures but I and others have had success in being involved in niche communities on Reddit and the like.

How are you doing today and what does the future look like?

Things are starting to pick up. New subscribers come in ebbs and flows. I can normally attribute where subscribers come from and what I need to do to press that lever. Sometimes though, I’ll get 40 free subscribers in a day and my only thought to attribute it is “Substack must have shown me more or something”.

As for the future, Organic search is a play that I can’t ignore any longer. I’m surprised at how little my Substack is ranking for. It’s an issue that I’ve seen across a lot of Substacks that I’ve been analyzing.

Going forward, the growth plan will focus on link building to provide an evergreen acquisition channel. I’ll probably use all excess proceeds going forward for this purpose.

Once I’ve got a sufficient base of organic traffic, the next step is to start buying small websites to grow and use them as case studies.

Through starting the business, have you learned anything particularly helpful or advantageous?

This isn’t the first time I’ve started an online business. Some of the trends stay constant in every online business I’ve built.

  • Try to build/have a network of builders. These people will help you stay on task and challenge you. They’ll also let you see that you’re not crazy for going outside of the typical 9-5.
  • It can be easy to feel like you’re being productive when you aren’t. Constantly make a list (literally write it down and prioritize by an impact) of tasks that need to be accomplished. Constantly plow through this list. You can waste hours/days analyzing, thinking about, or reading about something that doesn’t matter to your overall goals. When you find yourself doing this, take a walk to regroup your thoughts and action plan.
  • Luck plays a big part in success whether people want to admit it or not. The good news is that if you work long enough at something, eventually you’ll get lucky.
  • Learn marketing and sales. These can’t be outsourced.
  • Never outsource something to start. If you can’t spend the time to learn the basics, you’re never going to know if what you’ve outsourced is good or whether you’re being taken to the cleaners in pricing/value. Some exceptions apply. IE-graphic design.
  • Dump as much of the profits back into growth. Your future self will thank you. Taking your profits and investing them at a 10% return pales in comparison to the returns you’ll get in your business.

What platform/tools do you use for your business?

The BowTiedOpossum is mostly a newsletter but it’s involved in other ventures or services that aren’t mentioned publicly very often. I’ll try to keep the list kind of short…

What have been the most influential books, podcasts, or other resources?

Podcasts are too slow for me. I learn quicker by reading and actioning. If I do listen to something, it’s usually an audiobook while I’m driving.

Both of the below books are extremely dated by this point. Even though they’re dated, I find myself continuously going back to them.

The 4-Hour Workweek by Tim Ferris

Trust Me, I’m Lying by Ryan Holiday

Two more works that stand out in my mind as particularly influential are;

Self-Reliance by Ralph Waldo Emerson

As a Man Thinketh by James Allen

Advice for other entrepreneurs who want to get started or are just starting out?

Stop thinking. Stop planning. Stop reading. Just get to work. Start building. The more you work and fail, the closer you’ll get to success.

Where can we go to learn more?