Essays
The First Dollar
July 27, 2026 · 6 min read
This week was mostly spent hovering at 399 followers on Instagram.
Every time I opened the app, there it was: 399.
Essays
July 27, 2026 · 6 min read
This week was mostly spent hovering at 399 followers on Instagram.
Every time I opened the app, there it was: 399.
Close enough to feel like a milestone was coming, but not quite there.
Then today, it happened….. Thomas Alan reached 400 followers.
I smiled. I took it in. I allowed myself to feel proud.
And then, almost immediately, another thought appeared:
Great. Is the sale coming next?
Maybe in the next ten minutes?
It did not!! That is one of the strange things about building a business in public. You can reach a milestone and diminish it almost instantly because it did not produce the next milestone fast enough.
Four hundred followers, but no sale. More engagement, but no sale. A growing audience, but still no first dollar.
As a founder, your mind starts working against you.
What is not clicking?
Why is no one buying yet?
Am I doing something wrong?
Those are fair questions. Thomas Alan is a business, after all. Eventually, people do have to buy something. Followers, likes, encouraging messages, and compliments cannot pay an invoice.
But I also had to have a more honest conversation with myself.
I am not asking someone to make a quick, inexpensive impulse purchase.
I am not selling an $8 candle or a $10 journal that someone can add to a cart without giving it much thought. There is nothing wrong with those products, but Thomas Alan requires a different kind of decision.
I am asking people to trust me.
I am asking them to see me as a credible voice in menswear, personal style, hosting, and the broader ways we present ourselves to the world.
I am asking someone to trust my eye, my recommendations, my products, and eventually, my guidance.
That is a much larger ask.
Clothing is personal. The right clothing can shape how someone enters a room, how comfortable they feel in their own body, and how confidently they show up for an important moment.
Style can affect a first date, a wedding, a job interview, a business meeting, a family gathering, or an ordinary dinner with someone you care about.
Thomas Alan is not simply asking customers to buy a jacket.
I am asking them to trust me with an important part of how they see themselves and how they want to be seen by others.
That kind of trust is rarely built in ten minutes.
There is another truth I have to acknowledge: professionally, I am still new to this world.
My background is in technology. I understand systems, infrastructure, processes, customer relationships, and how to build something that can operate effectively behind the scenes.
I have always had a strong interest in style. I have experience working in retail. I know what it means to put together a thoughtful look and help someone feel more confident in what they are wearing.
But building Thomas Alan is different.
This is not me stepping into someone else’s store or selling within someone else’s established vision.
I am building the store.
I am creating the vision.
I am choosing the products, developing the language, shaping the customer experience, meeting vendors, sourcing inventory, designing the environments, and deciding what kind of world Thomas Alan should invite people into.
Everything has to be introduced.
Who am I?
Why am I credible?
Why should someone trust my taste?
Why should they believe Thomas Alan can help them?
Why should they spend meaningful money with a young brand instead of going somewhere familiar?
Those questions are not insults. They are the questions every customer has a right to ask, even when they never say them out loud.
My job is to answer them.
I have had to walk back some of my negative feelings with grace.
The company has only been actively selling for barely two months.
That is not a long time to build recognition, much less trust.
People need time to see the products. They need to understand what the brand represents. They may need to watch how I style clothing, how I discuss fit, how I choose vendors, and how I approach quality.
They need to hear from me more than once. That has become one of the biggest lessons of this early stage: I have to keep reintroducing Thomas Alan. I cannot assume that someone who followed after seeing one outfit understands the full brand.
I cannot assume that someone who liked a post knows we offer made-to-measure services. I cannot assume that someone who enjoys the imagery understands what they can actually purchase.
The message has to be repeated, clarified, and demonstrated in new ways. That repetition does not mean the original message failed. It means brands are built over time. The audience is teaching me that!!
They are showing me which ideas resonate, which images create curiosity, and which parts of the story need more explanation.
Four hundred followers may not represent 400 customers, but they do represent 400 opportunities to listen, learn, and continue building.
Giving myself grace does not mean avoiding the difficult business questions.
I still have to ask whether the product offering is clear enough.
I have to ask whether there are enough products to choose from.
I have to ask whether the path from discovering Thomas Alan to making a purchase is simple. I have to ask whether I am telling people what to do next or assuming they will figure it out on their own.
I have to become better at asking for the sale and patience cannot become an excuse for inaction. Urgency cannot become a reason to dismiss genuine progress.
Both things can be true.
Thomas Alan needs revenue, and Thomas Alan is still accomplishing something meaningful before that revenue arrives.
Building trust will also require relationships beyond social media.
It means developing stronger relationships within the menswear industry. It means meeting suppliers, learning from people with deeper experience, listening to potential customers, and continuing to prove that Thomas Alan belongs in this space.
This coming week, I am heading to Chicago for Chicago Collective.
The goal is to begin building out the apparel side of Thomas Alan. We already offer made-to-measure, but the current product selection is still light.
Chicago represents the next stage: meeting suppliers, sourcing additional products, understanding the market, and building the relationships required for Thomas Alan to become the brand I know it can be.
Not simply an Instagram page.
Not merely a personal style project.
A real, lasting, and eventually powerful business.
The first dollar will matter.
Technically, I hope it will be more than one dollar. Hopefully, it will be the beginning of hundreds, thousands, and eventually much more.
But the first sale will validate a transaction.
It will show that someone has moved from watching to buying, from curiosity to participation, and from interest to trust.
What it will not do is validate the existence of the work.
The work already exists.
It is present in every late night after my regular job, every product decision, every supplier conversation, every website update, every piece of content, and every uncomfortable question I have had to ask myself.
The first dollar will not make Thomas Alan real.
Thomas Alan is already real.
That first dollar will simply make the journey a little sweeter.
Until then, I will keep introducing the brand, refining the offer, building relationships, earning trust, and giving myself enough grace to recognize that 400 followers is not nothing.
It is not the destination.
But it is movement.
