Welcome Avatar! We’ve got a guest post entirely written by BowTiedBoat.
He’s the latest and greatest to continue down the venture of being a business owner. One thing you’ll notice from this erratic journey is that some people simply have the “bug”. It’s quite similar to BowTiedBroke who started something, didn’t work, started again, got over leveraged, started again and suddenly made it big.
As we’ve said time and time again, if you simply show up and try, eventually you’ll learn enough and the right idea will miraculously appear “luck”
The BowTiedBoat Story
What’s up Jungle? I’m BowTiedBoat, a day 1 silent reader and now I’m here to tell you my story.
Incredibly grateful to have this opportunity! Seeing the success of this community has been incredible. Being able to share the same space as Gator/Fawn/Calvin with NOBS, TJ with The Outgoing Co., Kobra with Morning Would, VampDeer with Presleep and countless others is a true honor. It’s insane how one X post can change your life.
I don’t consider myself an unlucky guy, but someone looking at my W2 employment history could make a good argument. I’ve lost my job 3 times in the last 8 years, 2 of them in the last 3. All despite being a high-quality employee and hitting my numbers. The way I view it, golden handcuffs have never been an option for me. I have no choice but to make it.
Along the way there were countless opportunities to give up. Following the principles BowTiedBull preaches let me not only survive these setbacks but thrive in the face of adversity. The difference in my attempts pre and post finding Bull is night and day.
My journey features 3 distinct businesses:
The Snow Business: A physical product company that is seasonal and depends on the weather. It was a failing business I bought into from a family member. Product was solid but the offer and marketing were trash. The goal was to use it as a training ground to learn and jump to something with bigger upside.
The Beer Bong Business: At my cousin’s wedding I turned the centerpiece into a beer bong and my next business was born.
Ariven: My Shopify SaaS business, my dream E-com app I’ve built over the last 2 years. It takes on-site personalization that previously only enterprise stores with huge dev teams could afford and makes it no-code and simple to run. Running the same playbook as Klaviyo by making expensive enterprise software user friendly and affordable.
Attempt 1 (2018)
In 2018 I got laid off from a sales job 6 months in despite being ahead of quota. It was a total shock and the one that hit the hardest. I was in year 3 of the snow business. Sales were low and growth was modest, so I knew it wasn’t my ticket to independence yet. During the gap, I did build out a website feature that is still the core piece of the funnel and was foundational to its success today.
My only shot in this brief window was getting the beer bong business to market and getting sales fast. The product had been stuck in manufacturing hell for the past 12 months. Found a new molder but it took longer than the window I gave myself, so I jumped into a new W2.
I did get it to go viral a few months later and sold $10k worth the first month. Problem was sales dove off a cliff shortly after. It’d require consistent viral videos to make it, and pre TikTok that is not sustainable.
I paused all marketing and sold the business. I framed it as an asset sale so I could recoup all the money I invested in the blow mold. I had a feeling it would never run again and would be worth near zero, so best to sell while it was hot. The mold has not run in the 7 years since the sale.
Lessons from Attempt 1:
This attempt was laughably far off from self-employment, but it instilled some deep lessons that set up my future success.
A W2 job is a mirage that appears stable. You can do all the right things and still get cut. I’ve had trust issues with employment ever since. I keep burn and debt to a minimum and always have enough runway to avoid desperation.
As BowTiedBull says, manufacturing in the US sucks, as much as I hate to say it. It’s expensive and the minimum order quantities are high. The majority are owned by private equity and don’t give care about your success.
Covid Panic (2020)
The W2 I was at got shaky for a second like many businesses. I got desperate and tried to rush into a new e-com business. I was viewing hundreds of e-com sites a day for idea inspiration, but the truth was my skillset wasn’t mature enough to take advantage.
I came out of the desperation fog and doubled down on building e-com skills at a rapid pace between the W2 and the snow business. Both businesses finished with record years online. I paused the search for a new e-com opportunity and doubled down on growing the snow business.
Attempt 2 (2023)
The 5 years between attempts were an insane contrast. The Covid bump the snow business got wasn’t temporary, it was an actual growth inflection point. It went from hobby business to a powerful side business, exceeding my W2 income at times.
I got married and had a family, so my burn rate went up. My philosophy didn’t change though, and the financial cushion grew even faster. I continued doing e-com full time at my W2, so I was getting paid to learn the skills to accelerate my business, and it worked!
The company I was at had their line of credit with Silicon Valley Bank. Shortly after the implosion the rounds of layoffs started. I was a key revenue generator, so I knew I wouldn’t get cut till the end.
It was a decent spot to be in. I only had to do the bare minimum to collect my W2 check and could put the majority of my time into the snow business to prepare for the jump.
The layoff came 6 months later and I was pumped and ready. I had revamped the site and brought new marketing channels online for my full court press.
The Tyson Punch
The first few months started strong and it was looking like I could make the jump. I already had the pressure of a pregnant wife, and one night in November I went to bed… and woke up with a dislocated shoulder.
Not a new problem, but one I had kept at bay, and I had decided years earlier that the next one equals surgery. I got under the knife as soon as possible so I’d be able to hold the baby in a few months. The injury and recovery sucked but was manageable. I was not going to let it derail my attempt!
Then the final blow came. That winter it never snowed.
January sales was decent, but the last week died off and dropped 60%. That’s when the market gave up on winter and moved on to spring, and I knew it was game over. We serve multiple regions and it’s not uncommon for one or two to have a bad snow year. Every single one being dry was unheard of, and sales stayed down over 50% most of the year.
The business is bootstrapped and run very conservatively with no debt, so no bankruptcy risk. But it couldn’t provide a livable income on its own. Back to the W2 I went…
Lessons from Attempt 2:
It’s all about timing, and the time was not right. The 2023 year end payout gave me runway to be picky on the next W2, and another W2 income was the best way to avoid the financial stress.
Double down on building your skillset. It drastically increases the surface area for finding a successful business, and the odds of building one. I read books like Cashvertising, went back through copywriting courses I’d taken, and reverse engineered high end sites.
Once you know what high quality looks like, you find the tier one operators and learn from what they do, not what they say. The courses were foundational, but the skills only turn into money when you put them to use in CRO, SEO, ads and more. Marketing channels constantly change, but the sales psychology behind them never does, so you can adapt much faster.
Keep yourself out of a desperate financial situation. I was taking big hits to income, but I had enough to comfortably get to the next round and keep pressure off the business. I see way too many people take money out of a business too early. It often leads to a desperate situation and taking on leverage.
I need to start another business to diversify income for down years. I’ll keep putting effort into growing the snow business, but I won’t be expanding the product line deeper into the niche.
Attempt 3 (2025)
We landed a solid ecom job shortly after my 2nd daughter was born, in a really competitive space where I would further expand my skill set. Shortly after getting the job, great business ideas started popping into my head unsolicited. BowTiedBull preaches that whenever you desperately want something you don’t get it. When you don’t need something, you get it in abundance. Funny how that works.
Picking the Next Business
I had three blue chip ideas in front of me: two ecom ideas and a Shopify SaaS app. The ecom ideas were layups with solid upside, more than the snow business.
But I was burnt out dealing with inventory problems, and the SaaS idea gave me chills in my bones. Why do we spend so much time personalizing and segmenting everything but the website? It just made so much sense.
I found a few companies already doing it, but they were all priced at enterprise level, complicated and required a technical team.
AI was making huge gains during this period as well. I had found the coding utility of ChatGPT early in 2023 and was making front end theme changes I previously had to outsource to developers. I used my time at the W2 to develop AI coding skills, building out sections and custom quizzes using Cursor and Windsurf. I was hooked! I got bored with front end pretty quickly and jumped to full stack development.
My timing worked out that I could build Ariven and own 100% of it. No dilution, no investor busy work, no having your vision watered down.
End of Employment
I had a feeling the W2 wouldn’t last much longer, but after a solid sales month I thought I was safe. Then Ariven hit what looked like a fatal flaw. The app’s initial core feature was the ability to use Klaviyo segments. We built out the feature only to find that we couldn’t use the Klaviyo cookie ID to identify user segments via their API. I was devastated.
Two days later, on the last Friday of the month, I got a calendar invite from someone I don’t meet with... I knew instantly it was game over. The whole team was let go.
My psyche was a bit roughed up on this one. My app looked dead, I was still shy of the 2x business to W2 income (about 1.5x), and it was a straight up bizarre experience at the company.
Days After The Job Loss
I’m so used to this by now that I bounce back quickly. I initially focused on the newly achievable AI improvements on the snow business. After a week of decompressing, I gave Ariven one deep session to survive or die. I found a way to do it, Ariven lives!
Ironically I ended up building out an analytics database that puts Klaviyo’s to shame. I almost killed it over a feature that’s now a modest nice to have...
The Sprint to Self-Employment
The plan was to work full time on the snow business as it’s the cash cow and work on Ariven as the side business. If I grew the snow business aggressively and hit 2x, I’d replace the lost W2 income and buy the runway to finish and launch Ariven the right way.
It was an all-out sprint. I needed to grow the business 30% in Q4 to lock in self-employment. It’s a seasonal business, so you only get one shot a year to hit the mark.
I ripped out the 3rd party apps that made the site fragile and moved those features native to the theme. This is where the AI coding paid off. The site became durable to changes, and I could finally redesign the key choke points so more users made it down the funnel. Then further improved Facebook ads took the site to its next gear.
I hit 50% growth in Q4. I overshot the mark and made it to the other side, with full ownership of my time and the runway to build and release Ariven!
Lessons from Attempt 3:
Skills and effort compound but the results will lag. That lag is the timing, and trying to force opportunity usually doesn’t work.
Swallowing my pride and going back to the W2 after being so close opened up an incredible amount of opportunity. It eliminated desperation and allowed the good ideas to flow. TAKE THE PRESSURE OFF!
Be outcome independent. I never tied my identity to my attempts. If it worked, awesome. If not, we know the drill and we’ll try again next time.
Put it all out on the field. These windows close fast. Suffering for a short time is much better than suffering the rest of your life knowing you didn’t push hard enough. I’ve seen people close to me not push hard enough when they had the opportunity, and the regret has broken them.
New Business: Eating Glass Round 2!
I’ve been through the eating glass phase once before with the snow business. It’s seasonal, so it was more like 5 years! Making it through the rejection, despair and fear once is a superpower going forward, but this round won’t be easy.
Not to mention the metric ton of noise I need to cut through in this space. I’m a Shopify site owner too and get solicited constantly. Now I’m one of them... but I actually have something valuable! Add in everyone saying SaaS is dead, record Shopify approval backups and agents being the only ones shopping. The emotional roller coaster is still there and believe me I ride it every day.
The biggest way to silence those emotions is early wins, and the snow business site has been Ariven’s testing ground and generating wins since day 1.
So what the heck is Ariven? It’s like Klaviyo meets conversion optimization. It’s proven that segmenting and personalizing email, ads and more greatly increases sales, yet every visitor still gets the same website... WHY?!?!
Landing pages are the only real attempt at matching intent, and that fades the second a user clicks off or comes back.
Ariven lets you segment users and serve an alternative version of your site that matches their intent, like the ad they clicked or the product they viewed. It holds that message across repeat visits. Clicked an ad with a specific angle? The home and product pages can match that angle. Showed interest in a product that isn’t your hero? Make it the home page hero next time they visit.
The Results so Far
We are seeing a near universal pattern of first-time visitors landing on a collection or product page convert worse than those landing on the homepage. You’re hitting them with decision overwhelm from the start.
On the snow business I’m running a 50/50 test of landing page versions of collection and product pages vs standard for first time visitors landing on them. It’s literally 3 sections from my homepage on top of the normal collection and product pages. We’re seeing double the conversion for those visitors. Three flows are adding 9% to total store revenue on half the traffic, which projects to around 18% gain fully rolled out!
My target for every store is at least 15%, and I have no doubt some of you psychos could hit 30%. I want to be your store’s top ROI!
Ariven’s Current Status
Ariven is launched and live on the Shopify App Store. The jungle helped me get here, so I want to give back! For the BowTid community, I’ll do white glove onboarding to get it running and making you money. We’ll extend the free trial till you see a proven return, plus a lifetime discounted rate. To take me up on the offer info@ariven.ai, DM me @bowtiedboat or book a demo on Ariven.ai.
Thanks again to BowTiedBull for the opportunity to share this journey. If someone with this many setbacks can make it, so can you! As my friend Joe Dirt said, “You can’t have ‘no’ in your heart. ‘No’ is not an option, brother…”
BTB Notes
Tons of interesting stuff and similar consistent story lines as well. In no particular order.
Working in sales and having a quota forced BowTiedBoat to learn one of the most important skills which is sales. IE. transferring emotion. While the industries were all different, sales is the most transferable skill
Layoffs are part of the W-2 life. Especially as you get older. Not surprising that he had a wild last 8-years. This is pretty much how it goes as you get older as expensive people move the operating profit line even if you’re hitting your numbers
The Snow based business unironically made him more prepared to survive the ups and downs. A cyclical industry based on the weather makes you understand that not every single year will be good. Understanding the difference between a bad year for the company and a bad year for the industry is paramount to surviving and keeping your effort at max level
The business was also legacy. He didn’t need to come up with some new wild adventure to get to 1.5x W-2. Reading about how difficult it was made it seem like it was worse than it was! This is because the emotions of working for yourself make you go through the rollercoaster “I’m going to be broke” wake up “I am going to be rich” wake up “I am going to be broke”. For better or worse, this feeling never goes away
The less you need the more you get. Never put yourself in a desperate situation where if it is a zero, it means you lose everything. Once he was stable, his thought process cleared up and now he’s sitting on multiple ideas that will generate a profit if any current venture is weaker than expected
It took years to understand that being outcome agnostic is the key to success. If you’re putting in the reps, that’s what matters. If the weather is bad, nothing you can do. If you quit though, that lasts forever. Do the right things consistently and eventually the pay off shows up. Having some mathematical day that you need to make it is unhealthy. Oddly, if you don’t have a mathematical day, we’d wager you get “there” faster than expected
We’ve got a huge range in the jungle at this point. People naturally scale up and expand. Everything from SaaS to SEO to MedSpas to Real Estate to Sleep formulas to social drinks to language learning… the list is hard to keep up with
Just like with anything else, we know a lot of people are working in the background and suddenly someone else will escape the claws of the W-2. The battle is never won (emotionally) however, getting control of your time is what people are really looking for in the first place. Outside of the 0.1% exceptions to the rule, you’ll always work on something and build once you get the adrenaline from your first real win
On that note, keep grinding. By the time you’re running multiple projects you’ll find that you have a list of other good ideas anyway (as you’re seeing from this post). Open one door and suddenly you see all the other doors.
Disclaimer: None of this is to be deemed legal or financial advice of any kind. These are *opinions* written by an anonymous group of Ex-Wall Street Tech Bankers and software engineers who moved into affiliate marketing and e-commerce.
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