This is a guest post by my friend Jay, the founder of Zlappo and Zylvie.
He’s been publishing a lot on his red pill entrepreneurship and dating newsletter – one of the few I enjoy reading. I’ve known Jay for many years (I even interviewed him a few years ago).
I asked him to send me his top 10 business lessons he’s learned over the years, and here they are.
Enter Jay:
I started my first business in 2011.
It was called Zuupy CrowdDeals (now defunct), a SaaS platform for vendors to create their own Groupon-like site without needing to pay 50% to Groupon.
I was a junior in college at that time (3rd year of university for you non-US readers), and, when I got my first-ever paying customer at $10/mo, I literally ran to the ATM, withdrew the money, and sniffed it.
I eventually dropped out of college to run it full-time.
Business was going well, until it ended in 2013 because I went to prison (another story for another day — yes, my 20s were tumultuous and exciting).
I’m now running Zlappo and Zylvie full-time (since 2020 and 2024 respectively).
Here are 10 lessons I’ve learned over the years as a bootstrapped solo founder:
1. Build a scalable and asynchronous business from day 1
This is probably the most important business lesson I learned in my life.
Whatever business you want to start, make sure that:
- There’s no income ceiling to it (meaning, in theory, millions of people can buy, and you can serve all of them through automation or delegation).
- Your revenue doesn’t scale linearly with your hours worked.
- It doesn’t require you to show up at certain times of the day (so you have time independence and full control of your schedule).
- Money doesn’t stop coming in just because you’re on vacation or go to sleep.
We live in the age of the internet, where computers, AI, SEO, social, email, etc. can do the bulk of the heavy lifting.
You shouldn’t need to work that hard in 2025 — you have leverage, so use it.
The key here is to create once, sell over and over again.
Think books, courses, videos, templates, artwork, software, etc.
2. Is there a market for your idea?
This might sound obvious, but first-time entrepreneurs have this habit of trying to be too clever or innovative by coming up with “novel” business ideas.
The chances of you being the first genius ever to think of a brand-new idea that can work are very slim.
It’s way more likely your clever idea doesn’t have a market, and you can’t make a business out of it.
Most likely someone else has tried out the idea, and it has failed to take off.
If there isn’t already something similar in the market (and they’re doing very well and still growing solidly), I’d look for another business idea.
There are no bonus points for coming up with new ideas. Period.
Whatever first mover advantage you have from actually chancing upon a rare innovative unexecuted idea that works will be more than nullified by your inexperience and lack of capital, know-how, domain knowledge, and distribution.
Stick with tried-and-tested products and markets.
Business is already risky enough; you should be derisking your business, not adding on more layers of risk just for egotistical reasons.
Just like Jason Cohen (founder of WP Engine) said, if you can’t find 10 people who say they’ll buy your product (and he emphasized “will” in the form of pre-orders or at least letters of intent, not “would”), your company is bullshit.
3. Can you reach your customers?
This is related to point 2.
Remember, you’re not starting a business with millions of dollars in seed funding and a wide network from your VCs and board of advisors.
You’re bootstrapping a business solo from your home office.
If you can’t reach your market directly, the market might as well not exist at all to you for all intents and purposes.
So whatever business you want to run, make sure that you have a direct line of contact to the decision-maker who will be buying your product.
I learned this lesson in 2019 when I built a piece of software for the healthcare industry and failed to even get my foot in the door.
I couldn’t even get into the merits of my software — I was cut off from even accessing the decision-makers by call screeners and such.
I was so naive then and wanted to break into the $100/mo and up SaaS market, but if it were so easy, everyone would be doing it, right?
Stick with the consumer market or, better yet, prosumers (consumers who behave/think like businesses).
If you aren’t already in direct contact with a whole bunch of your potential customers (whether through email, social, forums, etc.), you’re adding yet another layer of unnecessary risk to your business… which brings me to my next point.
4. Build your distribution first
It’s incredibly difficult to start a business from 0.
Anyone can build a product in 2025 (especially with the advent of LLMs and AI agents), so even that has been thoroughly democratized and is no longer a barrier-to-entry.
Your coding skills, your writing skills, your videomaking skills, etc. they’re practically all obsolete (or going to be soon).
What differentiates a successful entrepreneur from an unsuccessful one is distribution.
A couple of weeks back, I wrote a newsletter on the importance of creating distribution first before even creating your product.
A reader agreed with me and even shared her own experience with me:
So that’s proof that it’s not just me talking out of my ass.
If you’re still working a day job, now’s the best time to start building up your distribution channels for 6-12 months at least:
- Text-based social platforms: X, LinkedIn, Reddit, Facebook
- Video-based platforms: YouTube, Instagram, TikTok
- Email list (the only marketing asset you really own)
Not only will you have a ready captive audience for whatever products you want to launch, you’ll also have your finger on the pulse of what’s cool or needed in that target market of yours.
You can always talk to your audience, ask them what they really want/need, test ideas, get feedback, spy on their conversations, etc.
Best of all, you have unlimited tries with them, you get to keep launching product after product at them until one sticks and takes off.
You don’t get that if you don’t have an audience to begin with.
It’s 2025 — like it or not, you have to be a creator/influencer for your business to stand a chance.
5. Timing is important
Ideally, whatever business you’re launching, you should be riding the wave of a macro-trend.
You should be coat-tailing something that’s growing and becoming more relevant/important over time:
- YouTube worked when it launched in 2005, because that was when broadband internet started to take off.
- Instagram worked when it launched in 2010, because that was when smartphones with cameras started going mainstream.
- AI startups work in 2025, because the advent of countless LLMs allow for the execution of unlimited business ideas.
Going beyond tech, whatever business idea or niche you’re working on, you have to make sure it’s not a dying or declining trend.
This ties back to point 2, because a dying trend means that the market is shrinking.
And it doesn’t matter what you do or how hard you work if that’s the case, because a dying market will drag you down with it.
6. Don’t have a partner/co-founder if you can help it
This means that your business should be viable with you as the sole employee.
You and you alone should have all the skills, time, money, persistence, tenacity, and will to make everything happen for your business.
If you don’t have the skills necessary to start, run, and grow your business, learn them.
There’s no other way.
Again I learned this lesson very early in my career:
I started my first business, Zuupy Crowddeals, with my college friend.
He was supposed to be the technical co-founder, while I was supposed to be the growth/marketing co-founder.
Guess what?
He got a job offer from Google and immediately left, leaving me high and dry with nothing but the product.
I couldn’t even build new features or fix bugs, because I had no idea how to work on the Django code base or indeed how anything worked.
(It’s okay, I eventually learned to code and took over the code base, but it could have been the end of my company if I weren’t resourceful enough.)
Also, you don’t want to build a personal brand where it’s dependent on 2 people to attract a crowd/eyeballs.
Who knows how many of them will stay on if you went solo?
Collaboration can take you to greater heights, yes.
But needing people is also a bitch.
Both of those things can be true at the same time.
If you must bring people on board, make sure they’re bolt-on, bolt-off and optional add-ons, and not bound at the hip to you where their existence and participation are integral to your own success.
This is actually good advice for life too.
7. Diversify your revenue model
I wrote last week in my newsletter that you should sell more stuff.
Yes, I did say to start a scalable business in point 1, but that doesn’t mean you give up other ancillary non-scalable sources of income.
If you’re selling courses as your main revenue model, and people approach you for 1-on-1 coaching, are you really going to say “no” to free money?
Also just because you’re selling courses doesn’t mean you can’t diversify and sell an app/software, for instance.
In general, the more stuff you sell, the more different ways people have to pay you money, which means the more diversified your revenue model becomes.
If 1 revenue source fails for whatever reason (and this will happen sooner or later, believe me), you have 4-5 more other streams of income to tide you through while you rebuild.
This comes later when you’ve already fully built out 1 or 2 revenue models, but it’s nonetheless an important problem to solve if you care about building a robust and sustainable business.
8. Diversify your platforms
This one ties in to point 7.
It’s not sufficient to diversify your revenue model.
There’s no point in diversifying your revenue model if they’re all funneled through 1 payment processor (e.g. PayPal or Stripe).
You need to diversify your payment processors (a lesson I had to painfully learn first-hand), your distribution channels (i.e. don’t rely on just 1 social platform, what if you get suspended?), and your suppliers/providers (e.g. have backup servers for redundancy, if you’re doing software).
The whole idea is to remove all instances of a “single point of failure” from your entire business workflow.
If tomorrow you get banned on X, at least you still have your YouTube channel and email list (and you can respawn on X if necessary).
If you don’t have the others, you have nothing.
Things fail in business. Accept it. Build redundancies for it.
9. Keep trying stuff and double-down on what works
Entrepreneurship is a process of endless iteration and pivoting.
You have a lot of unknowns when you first start a business, and it’s your job to crystallize everything through persistent and thorough experimentation.
You’re supposed to figure out who your target market is, what distribution channels you can reach them through, what products they want to buy from you, what price point they can bear for your products, etc.
You start from a blank slate; even if you have a “business plan,” it’s all just hypothetical guesswork, all of which you need to test one by one in the field.
If something is not working, move on from it, try something else.
This might be a product, a distribution channel, a marketing campaign, a growth strategy, or even the whole damn business idea.
It’s never too late to turn around and start all over again if you’re on the wrong path.
If you’re on the wrong path, all your hard work is going to be wasted anyway, leading to burnout and ultimately failure.
Rip everything out and start again if necessary.
10. Work only on your current bottleneck
Every business has a bottleneck that’s stopping it from growing.
Growth only happens when all the stars are aligned, and you don’t know which star(s) is out of alignment at the moment.
You need to do some diagnosis to find out if it’s your product, marketing, or market that’s the issue (hopefully not the market, because that’s outside your control).
If it’s the product, working on your marketing won’t bear fruit — all that traffic will be wasted on a subpar product that leaves people dissatisfied and even feeling like they’ve been deceived.
If it’s the marketing, working on your product will be wasted effort, because your product is already good enough — the problem is not enough people are even aware of your product in the first place.
If you want to move the needle, you need to be an expert in diagnosis and sniff out the current limiting factor of your business, and work exclusively only on that.
Remember, you’re a bootstrapped solo founder, you don’t have the luxury of time or money to be working on the irrelevant like a big bloated corporation.
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And that’s all I have for today, I appreciate you reading to the end.
If you want to keep in touch with me, please subscribe to my entrepreneurship newsletter for more business lessons.
I send my newsletter once a week where I usually cover my most salient learning point of the week.
With thanks,
Jay
