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  • Writer's pictureJon D'Alessandro

Why I'm Closing My Business (and Everything I've Learned Along the Way)

30+ Lessons from 5 Years of Entrepreneurship

Tuesday, February 23, 2021 marked the fifth birthday of my first business venture as well as the day I shut its doors.

In this article I'll share everything I learned in the last five years about:

  • Running a viable side hustle while working full time+

  • Marketing "boring" products

  • Creating a passive business model as a solopreneur

  • Quickly upskilling yourself to become a more formidable founder

  • Creating a private-label product line with a multinational supply chain

  • and much more... well as why I've ultimately decided to close shop.

I almost didn't publish this. It's more personal and candid than most of my other writing (not to mention much longer). But I thought that if it's useful to at least a few people, and allows me to express my sincerest gratitude to my customers, vendors, and supporters, then it's worthwhile.

So grab your drink of choice and join me on this long and winding road (Note: if you're strapped for time, skip to the end for a consolidated list of lessons learned).


Table of contents:


The goal

While working full time in 2016, I founded Ambition Menswear, a men's luxury fashion business specializing in neckties.

From the beginning the goal was to scratch an entrepreneurial itch and create my own real-world MBA. The venture only inflamed my interest in entrepreneurship and taught me more than I ever could have imagined.

Why would you start a tie business?

I exclusively worked manual labor jobs throughout high school and college. For example, my first internship was unpaid, so I interned for part of the week and worked demolition the rest.

So when I started my career at an investment bank after college, it was a big deal for me. I was proud to make money using my brain instead of my body, to trade in my work boots for a tie.

But I soon realized most decent quality ties are inexplicably expensive. I would look at a price tag and imagine how many hours of throwing scrap metal into a tandem trailer it would take to pay.

And so the business began by "scratching my own itch." By looking at where I was spending my own money, and creating the business I wished existed — selling great ties for sane prices.


Let's address the inception of a somewhat unconventional brand identity: "Ambition Menswear." I could have used a more generic brand name, or heaven forbid some kind of pun like so many competitors. But I quickly learned that in a crowded market, different is better than better.

In addition to "ambition" being a pretty loaded, high-valence term, it represented the customers my business would serve. The customer is the hero of the story, not your brand, after all.

For the most part only ambitious men - guys who are uncomplacent, who strive to do and be better - wear ties. Sometimes by choice, sometimes because it's expected, sometimes both.

Maybe you've heard the old saying, "Dress for the job you want, not the job you have." That's where my brand stepped in, like the wise mentor in the hero's journey.

It's dangerous to go alone! Take this beautiful skil necktie.
Sort of like this

Many customers and influencers found it compelling, and it allowed for some unique advertising angles. Others found it confusing or off-putting — it's not always cool to admit you're ambitious.

But for a majority of people, the brand didn't register at all, much less resonate.

In retrospect I could have spent a fraction of the time on branding and still achieved 99% of the same results. So I learned that less is more.

It's true for branding - look at how many companies succeed in spite of crappy branding - but applies just as well to most other areas of business.

And I also learned that, to be candid, I loved creating a brand, but I only liked running it. This also taught me a lesson about time management...

MVP mentality

I think of it as the "glamorous activities" trap: when you launch a business, no one is over your shoulder telling you how to spend your time. So it's natural to gravitate toward activities you enjoy and justify it because everything seems important.

But then you lean a little too far, trying to be a little too perfect. It becomes an excuse to ignore the hard-but-necessary things that actually grow your business. It's also a relic of CYA culture and day-job mentality, where there is low defect tolerance given most roles are relatively narrow in scope. As a solopreneur, you have the broadest job imaginable. Defects are inevitable.

Starting a business - especially solo - means applying the MVP mentality across the board. You live by the mantra "done is better than perfect" or the entire building collapses at the expense of designing the perfect lobby. The website doesn't have to be immaculate, it just has to work. The sales copy doesn't need to be perfect, it just has to sell. The initial product doesn't have to be a hole-in-one, it just needs to address a problem. And so it goes.

Then, without losing the focus on growth, you iteratively improve, optimize, and polish.

The product

As the business took shape, I poured over forums, googled "best tie brands 2016" more times than I could count, and spent hours wandering around tie racks at department stores. I mapped out the competition, studying their advertising, products, and platforms. I thought deeply about what I liked, what I was willing to spend money on, and why.

It was all useful, but it was like gathering circumstantial evidence. It would have been exponentially more valuable to spend that time actually talking to prospective customers.

I would have learned who my customers are, where they get information on products, what they like, and what they will actually pay for (i.e. not just what they say they'll pay for — huge difference). Importantly, I might have learned whether there was a need for my business at all.

Talking to customers also helps build a network of potential early adopters and feedback providers. If you can manage it, it's easier to build an audience and then launch a product to them. The high-end hunting apparel brand Kuiu is a good example of this. The founder blogged about the process of launching the company, sourcing the products, etc. He built a loyal following, accumulating 100k eager readers who provided input and feedback along the way. On launch day, Kuiu managed $500k in sales.

If you play your cards right, then some proportion of these early adopters tend to become loyal fans and advocates, referring others to your business, aka evangelist marketing.

So for me, it was like navigating the pre-launch phase with a compass when I could have used a GPS...

But then the business almost ended before it started.

Supply chain 101

As an unestablished outsider, I reached out to dozens of potential suppliers and got rejected or ignored by a vast majority.

I was being rejected by suppliers — did I have to beg these people to take my money?

It was an unsettling start.

It was due in part to asking for very low MOQs. This signaled that I was a small buyer and/or time-waster. Which I was, kind of. But it was one of the few things I did right.

I wanted to quickly introduce an MVP. It's better to start small and pivot than to dump money into a product nobody wants. With a basic introductory product (or even just a mock-up and a couple social media ads), you can get in front of customers quickly and start learning, gathering feedback, and adjusting as needed.

If you indulge in wishful thinking and invest a ton of money into an unwanted product, you'll spend many frustrating years trying to sell off the inventory and/or recoup your investment, growing increasingly disenchanted all the while.

It was tedious. But these stubborn vendors taught me to be equally selective in choosing a supplier. I honed my approach. And I learned how important it is to find the right supplier and never lower your standards out of frustration or desperation. This lesson - never lower your standards - remained an asset throughout the life of the business.

Eventually I found a supplier in Rome that let me purchase a "sample order" (which for me was a full-blown order) of 100 ties (10 styles with an MOQ of 10 ties per style).

I got to choose from a big ass book of designs, and for the first time it really hit me that I had started a "fashion business."

Sink or swim graphic design

In the spirit of a quick and inexpensive launch, I was hesitant about spending money on a graphic designer. And so I found Inkscape, a free vector editing program, and started experimenting on a logo and brand label design.

A great way to learn a new skill is to understand the basics and then dive into whatever problem you're trying to solve. For example, I learned to play the guitar quickly - and stuck with it - not through rote repetition of chords and scales, but by diving into my favorite songs and learning along the way.

I have nothing but positive things to say about Inkscape. I would go on to do all of the graphic design for the entire business using Inkscape and free, royalty-free fonts and vectors. And now this rudimentary graphic design skill comes in handy constantly.

When you have limited resources, it's amazing what you can accomplish with technology, ingenuity, and a willingness to learn — or what I would call "Millennial elbow grease."

I ordered the brand labels, crossed my fingers that they'd look alright in real life, and crossed my toes that they'd actually make it to Rome.

Being "in business"

All this crossing of phalanges seemed to work. After a few weeks, a long, bruised cardboard box landed in the States. I unpacked the crumbled Italian-language newspapers to find 100 immaculate, handmade ties in transparent plastic sleeves. We were in business.

I had successfully sourced products and managed a global supply chain. Now came the hard part: actually selling the ties.

When hacking goes wrong

A good first step was product photos. Some services wanted ~$10-20 per photo, per angle, which would mean dropping several hundred dollars before even launching. I didn't pay a graphic designer, so why pay a photographer? (Needless to say, this was flawed logic.)

Basic product photos were attainable. Nowadays phone cameras are adequate for the raw images. Lay down a sheet of white paper, get the lighting right, and use a basic tripod (I used this one with this phone mount).

Editing meant learning yet another program, Gimp, an oddly named raster graphics editor. Again, rather than RTFM, I learned the program by problem-solving my way through tasks that needed to get done. The result was passable:

The Navy Blue Star tie, my first product to sell out.

I didn't fare as well with the other photos.

For a men's fashion brand, lifestyle photos are crucial. For me this was a shit show. I had a friend (who is by no means a photographer) take pictures of me (who is by no means a model) walking around Manhattan in the ties. Only about 1% of the pictures were remotely usable. In retrospect, a legit model and photographer were 100% necessary.

It's vital to understand the difference between being economical vs cheap, or the difference between hacking your way to a result vs half-assing it.

The only thing that (sort of) saved me was 1.) taking pictures of the ties wherever I traveled...

Blue Plaid Tie Philadelphia Museum of Art
The Blue Plaid Tie outside... the Philadelphia Museum of Art. (Absurd, I know.)

...And 2.) requesting production photos from suppliers. These came out much better, and reinforced my products' handmade quality for a very discerning consumer:

Ambition Menswear necktie under construction - handmade
Our Red & Blue Regency Striped Tie under construction

However, my flawed logic also extended to my websites. If I didn't pay a graphic designer or a photographer, why pay a web designer? Cue the countless hours and dollars spent tinkering with Shopify, Wix, etc.

But even a broken clock is right twice a day. This DIY mentality helped me stumble into something I really enjoyed.

Learning to write

Here's a fatal flaw for many would-be entrepreneurs: the common misconception that if you're "good" at writing, you'll be good at copywriting.

There's nothing more disappointing than trudging through the marathon of creating a real-life business and product...

...spending hours delicately crafting advertisements...

...and then watching as your ad spend rises to the heavens and your conversion rate sits dejectedly at zero.

Sorry, one thing is worse — doing that over and over, impotent and helpless, spinning your wheels and questioning every decision you've ever made in the process.

An actual picture of me running my first ads in 2016

I vowed to suck less at copywriting.

I poured over free and paid resources - everything from newer books to the reliable classics to really old, obscure stuff. Getting good was a Herculean task — with all that information I endlessly practiced, experimented, split tested, refined, etc. Commuting to my day job, you could often find me honing a product description, writing 20 versions of a headline, or trying to come up with new ways of saying "these ties are nice."

This quote was my beacon:

"It's none of their business that you have to learn how to write. Let them think you were born that way." — Ernest Hemingway

For me, the most valuable resource was John Carlton's Simple Writing System, a masterclass in direct response copywriting. I still revisit my notes constantly.

I'm tempted to step up on the old soapbox and tell everyone they must learn the basics of copywriting (which I believe), but a better lesson might be to find and become highly proficient in at least one startup-relevant hard skill (e.g. coding, finance, sales, etc.). It's not enough to be the "idea guy" or "strategy guy."

So after learning copywriting, my ads converted. Even outside of direct advertising, the products sold themselves on the strength of the website copy, headlines, product descriptions, CTAs, SEO, etc.

Sure, my copy wasn't flawless, but it worked, and I continuously tweaked and improved it over time. As we explored before, that's better than trying to nail "perfect" in the first draft.

(To share what I was learning and working on, I started a copywriting-themed Instagram account, which led to a brief foray into freelance copywriting. The experiment picked up traction and took on a life of its own... but that's a story for another day.)

Marketing boring products

If you can sell a "boring" product like a necktie you can sell just about anything.

The key is that even the most boring product is exciting to someone.

The ever-shrinking group of people who like wearing ties really like wearing ties. And they appreciate and will pay for quality. Plus they're generally more affluent, with more disposable income. In other words, it's an excellent niche.

Now 99 times out of 100 I would say: Don't be all things to all people. Niche your way to growth.

Find potential customers with an existing desire for your product and convert them. Don't try to convert people that have no interest in or use for your offering. And don't write for, or try to please, everyone.

“Good advertising is written from one person to another. When it is aimed at millions it rarely moves anyone.” – Fairfax M. Cone

Pay no mind to those who don't "get it" — your product is not for them. In the beginning, Identify a valuable niche and focus only on your "ideal" customer. Understand why they find your product exciting and then, with equal parts honesty and enthusiasm, tell them what they need to know.

“Good copywriting is a transfer of enthusiasm.” — Kevin Rogers

Here are some more tips to help sell "boring" products, based on my experiments:

  • Be clear, not clever

  • Tell a good story

  • Be different / find a way to stand out vs competitors

  • Experiment with nontraditional marketing angles

  • Relentlessly A/B test

  • Understand your audience well enough to use familiar in-group language

  • Address both the rational and emotional decision-making functions

Then, importantly, go above and beyond for customers once they've handed over their hard-earned money. For me, I made consumers in a small niche very happy. The products never received less than a 5-star review.

Amazon Ambition Menswear review
Like Michael here, whose review is better than any sales copy I've ever written

Unfortunately, I didn't reach enough of them to establish a beachhead. Worse, the niche was small and shrinking. This is a recipe for disaster.

It's easier to be a B player in a big, growing niche than an A player in a small, shrinking niche. In a growing niche, as long as you don't screw up, you can ride the wave to growth. In a dying niche, you will fight tooth and nail to maintain traction. It's like swimming upstream.

So if you're lucky enough to find the perfect, growing niche, how do you avoid screwing up?

For starters, don't chase blockbuster, "overnight" success. Optimize for longevity. You don't want to plan one huge, flimsy, hail-mary launch. Launching is not special, it's something you can continuously do. You want a business that builds a strong foundation and then improves over time, via a thousand tiny, incremental steps. A business that weathers storms and setbacks. One that makes people extremely happy, one customer at a time.

So what does a strong foothold in a niche look like? It's some version of the lauded "1,000 true fans." You have to do things that don't scale to find and delight the innovators and early adopters. Convert some of them into evangelists and loyal supporters and you have a shot at "crossing the chasm."

Sometimes the "think big" mentality can cause you to act too much like a big company. You attend to the collective at the expense of the individual. My business suffered because I didn't consistently apply the fundamental rule of "doing unscalable things." I didn't go out and manually recruit new customers, create a horde of advocates, and get the flywheel turning.

There were a million "unscalable things" I thought of but didn't act on. Seems like a stupid, avoidable mistake, right? The problem is rarely a lack of information or ideas — it's a lack of will.

Customer experience best-practices

On the other hand, the most valuable unscalable things I did involved killing it for existing customers more than reaching new ones.

For example:

  • Making, hand-cutting, and hand-writing personalized thank you cards for almost every single tie.

  • Surprising customers at random with upgraded shipping.

  • Offering personalized high-value discounts.

  • Offering referral discounts

  • Creating scratch-off style discount cards by hand (credit to this post from the guys at Mini Materials).

  • Offering a huge job interview discount where the ties were effectively sold at-cost.

  • Reposting customer photos on social media.

  • Offering a generous, high-touch return policy.

  • Corresponding with and checking in on customers (sometimes even via snail mail), and so on.

Anecdotally, "customer service" seems to be a huge pain for many founders. But I was less bothered by it. I'm sure I had some naturally inclination, but I also recognized the commercial impact of customer retention. Repeat customers are more valuable than new customers.

It's expensive for most businesses to acquire new customers. It's much more profitable for one person to buy multiple products than to have multiple people make single purchases. Repeat purchasing also indicates that you're doing something right — that you're on your way to obtaining the illustrious Product-Market Fit. And as we've explored, repeat customers can help create word-of-mouth growth.

The problem was my scale tipped too far in this direction, and not enough toward acquiring new customers. Screwing up the balance is a deadly mistake.

The luxury paradox

Fortunately I talked to enough customers to at least guide my product offerings.

Based on feedback and demand, I started offering authentic Grenadine Ties from Como, Italy.

Genuine Grenadine Silk Ties originate off the shores of Lake Como in Northern Italy. In boutique workshops, the luxurious gauze-like fabric is woven on old, wooden shuttle looms and then hand-crafted into neckties. Sean Connery famously sported these ties as James Bond.

Connery in a Grenadine Tie on-set while shooting Dr. No (P.S. this was in 1962 - that's a cigarette case, not a phone)

I'll spare you the rest of the sales copy, but the product was awesome.

To this day I'm shocked the vendors worked with me. They catered mainly to very well-known luxury brands who charge between - I shit you not - $150-200+ per tie.

My Grenadine Ties quickly outsold the more "basic" ties by a huge margin, so I expanded my inventory accordingly.

In the spirit of trying to exceed customer expectations, I sold these ties at a modest price. Unfortunately my first supplier did not feel the same about me, and so my margins were painfully thin.

As an experiment, after every couple sales I gradually raised prices. I was surprised to find that as prices rose, customers purchased even more.

It was one of those rare, paradoxical products where a low price repelled customers. A high price created desire in itself, not least because it indicated quality just as much, if not more so than as any sales copy or marketing materials. It also attracted higher "quality," lower-maintenance customers.

Out of necessity I continued raising prices, and one day it dawned on me that I had entered "luxury brand" territory.

Luxury brand marketing was an entirely different animal — it was a fascinating learning experience but I'll share those lessons another day. The overall takeaway here is raise prices. Seriously.

Cognitive dissonance

My price point was still a fraction of what competitors charged for same ties (in some cases I mean that literally — the same ties, produced at the same factory).

But I was acutely aware that I was slipping away from my initial "affordable luxury" mission.

I'm not shutting the doors because of some moral conundrum - far from it - but it did create some internal tension. Things suddenly felt less fun and experimental. There seemed to be another lesson tucked into this cognitive dissonance: your tactics and strategy can (and will) change, but never lose sight of your business' ethos.

The relationship business: a story

After one exhausting day of work, I found myself sitting in a hotel lobby across from an immaculately dressed stranger from halfway across the world. No, it was not an exotic date. I had contacted a new Como supplier and this was their account rep. Let's call him Marco.

I flipped through a massive fabric swatch book, chugging a massive coffee, feeling like a massive impostor.

I had that "Oh crap, I guess I'm in the fashion business" feeling again. Marco eyed my less-than-stellar outfit, puzzled over my brand and business model, and raised an eyebrow at my misunderstanding of common industry jargon.

But as I got to know Marco I realized he was a great (and nonjudgmental) guy. I placed an order. And then many more.

In one meeting, I asked Marco how he got into the tie business. In his 20s he played drums in a rock band. They gigged most nights of the week, playing at clubs until the early morning hours. Marco would drag himself home, sleep the day away, and then do it all over again. His father watched this play out night after night, fuming. Quit that band, he would demand (in Italian), and get a real job. Eventually the tension in the house became too great. Marco gave in and got a "real job," drumming up business for a tie manufacturer.

In one meeting, Marco brought along the owner of the company's son, who joined him in New York to learn more about the business. He was around my age and spoke good English. At one point Marco stepped away. After some small talk, the owner's son confessed to me that he had little interest in the fashion business. "Same here," I wanted to admit.

Moral of the story? Never fear "Impostor Syndrome." Most people are just winging it.

In the end, I built great relationships with this new vendor. While my price point didn't change significantly, I got much more for my money. The products were higher quality. I had access to a greater variety of styles. Everything became smoother, faster, and more transparent. I felt less like a bother to my supplier and more like they were invested in my success.

Every business is a relationship business. No man is an island, as they say. You build relationships with vendors, investors, customers, co-founders, etc., and your venture succeeds because of it. This is non-negotiable. Without strong relationships, you can't build a strong business.

Enter Amazon

Somewhere along the way I got tired of coming home from late workdays and spending the rest of the night fulfilling orders. I was already on Amazon, but I longed for that magic Prime button and that warehouse full of people handling my shipping. I eventually gave in and enrolled in Fulfillment by Amazon (FBA). I coughed up the $39.99/mo. + storage fees necessary to be a "professional seller."

My initial concern was whether enough customers were looking for products like mine on Amazon, a marketplace that calls to mind books, electronics, and Made-in-China nicknacks.

My worries were unfounded. People didn't hesitate to add relatively expensive "men's luxury accessories" to their cart right next to phone cases and waffle makers.

I was also one of the few Prime-eligible merchants selling handmade Italian ties, and the only one selling authentic Grenadine Ties, so I carved out a small monopoly and the ties sold themselves. Over time I pulled away from other sales channels and focused solely on Amazon.

Aside from the up-front work, all I had to do was handle orders from suppliers and shipments to fulfillment centers. I knew if I grew more and played my cards right, it had the potential to become a real-life, "4-Hour Workweek" style cash-flow business.

Until things headed south with FBA...

On mistakes & solopreneurship

...Which is an article in itself that I'll never write. I'm not here to complain about Amazon, or limited resources, or how no one's buying ties while working from home mid-pandemic.

I have no one to blame but myself for the success or failure of my business. I could have succeeded in spite of these things. As mentioned, I knew what to do - or at least what to try - but simply didn't.

I made plenty of vital mistakes, some of which I've explained or alluded to: refusing to spend money on product photos or graphic design, becoming too complacent and reliant on Amazon sales, failing to do enough "unscalable things," how I had super-niched myself into subsistence, but not success, failing to properly prioritize new vs existing customers, etc.

But most importantly, I quickly discovered that my passion level for the fashion business was, maybe, 3 out of 10.

Now, I'd say that before you launch a venture, you need to honestly ask yourself:

"On a scale of 1-10, how passionate am I about this subject? How enthusiastic would I be if I was still working on this same exact thing 5 years from now?"

8+ is where you want to land. Don't pick 7, that's a cop-out. 6 or less means it'll become draining more than fulfilling and exciting. It will burn you out.

Two ingredients to solopreneur success

My hypothesis is that there are two main factors that can mitigate solo-founder burnout:

The first is accountability. It's a huge, albeit uncomfortable asset in the entrepreneurial journey. Accountability is largely absent as a solopreneur, because as discussed, no one is over your shoulder making sure the work gets done. Sure, you're accountable to customers, and to people you owe money to. But real, hovering-over-your-shoulder accountability comes from investors, cofounders, employees, a significant personal investment, or an ambitious, compelling mission or vision. Accountability helps you push past plateaus that might otherwise submit you.

The second and arguably more important variable is passion. Please resist the urge to roll your eyes — Passion is an exceptional hedge against the pain, frustration, and doubt inevitable in the founder's journey. It can emerge from a deep interest in the business area or product, a contagiously passionate co-founder, a sense of community surrounding your brand, and/or a commitment to solve a very interesting, valuable problem. Passion gives you an extra gear when the going gets tough. It fuels the innovative ideas and unscalable things required to kick-start your business into growth. It encourages the continuous learning necessary for sustaining and evolving your venture.

Without accountability and passion, you set yourself up for unrelenting toil and trouble, and inevitably, defeat.

On "defeat"

Running a side business while working 40+ hrs/wk is no joke, especially when selling a catalogue of physical products. It forces you to make sacrifices and be hyper-cognizant of how you spend essentially every minute of the day. Things become a zero-sum game — Do I spend this hour on customer acquisition or customer retention? Do I spend the rest of the night answering emails or with my significant other? And so on.

While stressful, in some ways it was a valuable exercise. You learn efficiency and discipline. You learn to make use of otherwise "wasted" time. And you learn how to leverage and invest time. For example, you discover that investing 45 minutes to exercise actually multiplies your productivity afterward, thus making up for the lost time and then some.

But dueling obligations and the isolation of solopreneurship can wear you down. I didn't crash and burn or lose my day job, fortunately. But I became foggy, incapable of full focus or presence, unenthusiastic. Even when I wasn't consciously thinking about the business, it was quietly consuming mental resources in the back of my mind. When I tried to relax, a reel would repeat in my head, "Go get something done." Instead I gradually did less and less and ignored the impulse to just accept reality and move on. It's always easier to half-ass something to death than to thoughtfully and humbly bow out of the ring.

Was it "failure" though?

Far from it. Sure, it wasn't the unexpected smash-hit we all quietly hope for from our ventures. But I crushed my main objectives for the business: to learn by creating a "real-world MBA," and to see what it's really like to start and run a business. For that, I am proud and extremely grateful.

What's next?

You might be thinking, "Why close shop now? Why not weather the storm and capitalize on the post-pandemic return to work en-masse?"

Putting aside the sunk cost fallacy, the lack of clear timelines, the shrinking niche, etc. — the prospect of continuing sounds exhausting. It's time to donate what's left of my ties and move on.

Despite shifting to a mostly passive business model, I've felt a constant subconscious cognitive load from this venture. It's time to free up some CPU and let my prefrontal cortex chew on other things for a while. It's time to leave an opening in my life and see what fills it.

For example, I'm sure my dogs Gertrude and Larry would love some more quality time.

And I'm looking forward to investing more time on this blog, too.

Earlier, we explored the value of passion. My passion is helping exceptional people get even better. You could argue that, in some roundabout way, that was the point of the tie business. It's the point of my actual day job, working in Talent Development in the Private Equity / Financial Services space. And it's certainly the point of this blog, where I provide information, tools, and resources to help people turn their ambition into action, and tactics into results.

So now it's time to double down.


So what was the point of this article?

I wanted to tell the story of a business most people will never hear about. To define and digest some of the many lessons learned. To express gratitude for my customers and vendors. To show that it's ok to talk about "failure" and everything it teaches. To motivate you to create your own real-world MBA and embark on your own entrepreneurial adventure. To encourage you to be more thoughtful and intentional about when to bow out and move on. To explore for myself whether this is the right decision.

Maybe I'll regret closing the doors. Maybe it will lead to something amazing.

For those who made it this far, I hope you found these lessons valuable. We learn more from failure than success, and it's better to learn from someone else's mistakes than to make them ourselves.

But a word of caution — Advice can work for or against you. You ultimately need to find what works for you.

If you found this valuable, interesting, or entertaining, I'd love for you to subscribe to my newsletter and join me as the adventures continue.

34 Lessons from 5 Years of Entrepreneurship (Consolidated):

  1. When in doubt, scratch your own itch. Create the business you wish existed, or find where you're already spending a ton of money and build a business there.

  2. Different is better than better.

  3. The customer is the hero of the story, not your brand.

  4. Less is more — this is true for branding but relevant for many other aspects of your startup.

  5. Don't let glamorous activities distract you from actually growing your business.

  6. Done is better than perfect.

  7. There is no substitute for actually talking to customers.

  8. It's not enough to learn what customers say they like. You must understand what they like and are willing to pay for.

  9. It's better to start small and pivot than to dump money into a product nobody wants.

  10. Find the right supplier and never lower your standards.

  11. A great way to learn a new skill is to understand the basics and then dive into whatever problem you're trying to solve.

  12. You can often make up for a lack of resources with technology, ingenuity, and a willingness to learn, aka "Millennial elbow grease"

  13. Understand the difference between being economical vs cheap, or hacking your way to a result vs half-assing it.

  14. A common - and lethal - misconception is that if you're "good" at writing, you'll be good at copywriting.

  15. Find and become highly proficient in at least one startup-relevant hard skill.

  16. Even the most boring product is exciting to someone.

  17. Don't be all things to all people. Niche your way to growth.

  18. Pay no mind to those who don't "get it" — your product is not for them.

  19. It's easier to be a B player in a big, growing niche than an A player in a small, shrinking niche.

  20. Don't chase blockbuster, "overnight" success. Optimize for longevity.

  21. Do things that don't scale.

  22. The problem is rarely a lack of information or ideas — it's a lack of will.

  23. Repeat customers are more valuable than new customers.

  24. Raise prices.

  25. Your tactics and strategy can (and will) change, but never lose sight of your business' ethos.

  26. Never fear "Impostor Syndrome." Most people are just winging it.

  27. Every business is a relationship business.

  28. You have no one to blame but yourself for the success or failure of your business

  29. Before you launch a venture, honestly ask yourself: "On a scale of 1-10, how passionate am I about this subject? How enthusiastic would I be if I was still working on this same exact thing 5 years from now?" 8+ is where you want to land. Don't pick 7, that's a cop-out. 6 or less means it'll become draining more than fulfilling and exciting. It will burn you out.

  30. Accountability helps you push past plateaus that might otherwise submit you.

  31. Passion is an exceptional hedge against the pain, frustration, and doubt inevitable in the founder's journey.

  32. Side hustles force you to make sacrifices and be hyper-cognizant of how you spend every minute of the day.

  33. It's always easier to half-ass something to death than to thoughtfully and humbly bow out of the ring.

  34. Advice can work for or against you. You ultimately need to find what works for you.

A moment of gratitude

Thank you to the customers who joined me on this journey, spent your hard-earned money on my products, left reviews, told friends, and showed off the ties. Thank you to my vendors for being patient with a total newbie and outsider. Thank you to my entrepreneurship professors at Rutgers University who ignited my interest in launching a venture of my own. Thank you to Y Combinator for Startup School and the education, accountability, and motivation. Thank you to the friends and family that encouraged me through the process.

And thank you for reading this.


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