I hated the startup theater, pitching, networking, and accelerator applications including YC and TechStars and MassChallenge. My cofounder flaked. I wound down business #1, returned most of the investor capital, and then started out on #2, determined to do things completely differently.

For #2, I had 3 criteria:

1) Prototype on my own, without an engineer

2) Don't just talk lean, do lean

3) The product must generate revenue from day 1

While I am not an engineer, I had strong enough digital skills to set up websites and leverage other tools to prototype. Month 1 was building the prototype, month 2 was getting it out to the marketplace and actually getting some early sales ... and then plowing that money back into the business to improve the product. 10+ years later, the business brings in a respectable middle class income, has helped put my kids through college, and, as TFA articulated, lets me "pursue any and all ludicrous business models, with no oversight."

Like a lot of people who bootstrap, I had to consult as well (still do, mainly as a hedge against platform risk). I am eternally grateful to my spouse who not only has an income to help support the family, but also good health insurance (more on this below, see https://news.ycombinator.com/item?id=40707068).

I have a similar startup backstory to this, for my second venture I went fully to the get paid to do your work camp. It's still hard, harder than anything I've ever done, but it's working out.

You must have picked out your:

- Payment provider (e.g. Stripe)

- Authorization server (e.g. Auth0)

- Backend language and framework

- Frontend language and framework

- CMS for your website (e.g. Wordpress)

What else is there in your list of things you had to pick when starting a project? I'm very curious.

I'm always amazed how blatantly clear it is that having health insurance tied to employment specifically discourages this kind of entrepreneurship, and the ability to "strike out on your own".

Literally handcuffs keeping people at their jobs.

One other observation: During the pandemic my spouse left her job to work with me full time. We had COBRA (health insurance based on her previous plan per federal law) for 18 months, which was great. Then we had to go to the open health marketplace. What a freaking disaster that was.

If you make any sort of middle class income, which we did through my business, you don't qualify for any breaks in our state's marketplace (Massachusetts Health Connector). The broker database they had for small businesses insurance was a joke - no one ever returns your call; it seems they are looking for midsized businesses where their commission will be larger.

I spent many hours comparing family plans on the Massachusetts Health Connector and eventually decided to bypass the marketplace and purchase insurance directly from the insurance company because it was a little less expensive and had a slightly lower deductible (but was still sky-high compared to COBRA/her previous employer's plan). We got reamed on the monthly insurance cost as well as the crazy-high deductible. She eventually went back to her old employer, and one of the primary reasons was getting access to affordable health insurance without crushing OOP costs.

1. Anyone who pays cash for a procedure should pay a price that is no more than the lowest price that any insurance company has negotiated for the same service.

2. Anyone who buys a health care plan from the marketplace should get a price that is no more than 10% higher than the cheapest negotiated price any company pays for the same plan.

3. Anyone should be able to deduct the cost of health care for income tax purposes, not just companies that buy health insurance for their employees.

We need to fix the price gouging in the medical system by incentivizing competition. With the way things are currently set up in the US, the hospitals are essentially written a blank check any time a patient steps foot on their premises. If we bring competition between the hospitals with price transparency, the prices will fall dramatically.

How do you envision this working for say emergency care, where as a patient you may not be in a state to make an informed decision about which hospital to visit?

The current scheme only benefits rich people whose ability to pay outrageous insurance rates is easy and less than taxes. Poor people get substandard care, middle class workers get boned. I spend more on healthcare than taxes, and half my taxes are paying for stupid healthcare, either directly or through proxy.

1) Services are often unique per patient. Even for patients with the same ICD-10 codes, the quality of service will vary. Hospitals cost different amounts to run. If you always peg the price to the lowest, it will be a race to the bottom for quality of service.

2) Patients are unique, with different health profiles, with different preferences for paying. Markets are different. Some markets only have one insurance payer.

3) Healthcare is already tax deductible

Additional out of pocket healthcare expenditure is only deductible if you itemize your deductions and you're only allowed to deduct medical expenditures in excess of 7.5% of your income (AGI to be technical).

So more significantly:

* bring back association health plans across state lines and industries, so small businesses can band together for group rates. https://news.bloomberglaw.com/daily-labor-report/biden-admin...

* Expand Direct Primary Care. https://www.dpcare.org/

* Allow primary care physicians, dentists, etc. to offer services without a state board providing "certification of need". This seems to just be gate-keeping / moat-building.

I'm not saying either or all of these are a perfect solution (nor do I think we need to find that solution immediately). As a small business owner, they'd make the health insurance handcuff problem easier to navigate by driving costs down.

I will say this - flying solo without health insurance does make you a FAR better consumer of healthcare services. You will comparison shop (made easier by price transparency rules). You will critically consider the necessity of gratuitous tests / procedures. You will learn that doctors are running profit-minded businesses like everyone else.

It also makes you reconsider some life choices (re: physically risky behavior).

I think the biggest fear I faced was the lack of catastrophic coverage (cancer, etc.). When we didn't have insurance (both small business owners) my wife and I probably consumed less than $1000 of direct services combined, per year. That part (direct pay for services used) was fine. Walking the tightrope without a safety net for expensive medical developments was our biggest risk. With kids it's even less of an option to operate that way. I've known many that have returned to corporate jobs for this reason alone.

1. The healthcare and health insurance marketplace is riddled with regulation. There is no such thing as offering a health insurance plan or a healthcare service in the United States absent any regulation. Every existing service is, more or less, imposed via regulation.

2. The current health insurance system dates, in its current form, either to shortly after WWII or to the adoption of the ACA, depending on your perspective. That’s somewhere between 14 and 75 years. Where are the plans you speak of from these entrepreneurs? What are they waiting for, letting all of this sweet, sweet, arbitrage pass them by? Biding their time? Toward what end?

I think both things are true, that we're getting a bunch of things right toward a successful entrepreneurial culture, but are also getting this one thing massively wrong and leaving a huge amount of further potential on the table!

Life is much more difficult in most places in the world than it is in the US. We have had more success with entrepreneurship because of a culmination of specific things, not a generalized "difficulty of life", which empirically does not exist.

It's also more common for successful entrepreneurs to have grown up without financial distress.

Sorry to shatter your dreams, but your theory is very silly.

I think it's okay to talk honestly about that. There's a LOT of waste and purely indulgent service in the current system. And as a person striking out on a business venture, I don't need concierge health services. I need a health safety net.

I think it hurts the conversation about UHC when that's waved away - telling people that they'll be bringing the best of low deductible in-network, gratuitously provided services to everyone.

UHC isn't about bringing great service to everyone, it's about bringing a higher level of minimal coverage to everyone.

It should still cost you less to hire yourself than it'd cost a company to hire someone to compete with you, even before considering things like pass-through taxation and agency problems.

Taiwan boasted more than 1.59 million small and medium enterprises (SMEs), according to the White Paper on Small and Medium Enterprises in Taiwan, 2022. This accounts for more than 98 percent of all enterprises, an all-time high. Further, SMEs employed 9.2 million people, representing more than 80 percent of the total workforce.

https://www.moea.gov.tw/MNS/english/news/News.aspx?kind=6&me...

I think the official number undercounts the many micro-businesses that exist around the food industry, markets, and services.

I respect this. It's something I've wrestled with a lot over the past ~year (especially in the last 6 months). You can see my relevant "Ask HN: How would you raise $600k for a boring software co?"[0] in which I shared my musings around this with the community. I'm currently contracting because I have to pay some unexpected medical bills but I am hopeful I will explore solopreneurship more this year (I'd much rather not go it alone tho, as stated in the thread).

I'm very lucky to have had multiple interactions with folks in that thread as well as having contacts that have raised funds and sold businesses... the advice is a resounding "not really doable" outside of a friends & family fundraise.

All of this to say, I admire Peter (have read his writings previously) and I share the same feelings quoted above although I am still willing to entertain outside investors (and all that comes with that) for the chance to have agency in executing a software business with less "lose my house" risk. For the same reason I would also take a leadership position at a startup. I've seen the effects of bad management and lack of empathy first hand and I know I could make a difference and have a positive impact on the internal culture of software development shops... But I don't get many bites when I go fishing for that.

[0]: https://news.ycombinator.com/item?id=37346497

I don't respect what he actually built. Leeching off others' work and while doing it blasting out ads which ended up being the first wave of making browsing unpleasant in the early 2000s. Without any actual contributions.

And that then paired with "I didn't know how to code, and I hated reading." It's this attitude that software engineering is somehow what you do after having watched a fews youtube videos and discovered stackoverflow. My aunt still thinks that. Thanks for perpetuating that myth.

The big difference with software engineering is that you can just do it, similar to writing or design or animation or anything that is just you creating some output. In contrast, even if you learn everything you need to know about being a lawyer online you’ll still need to go to law school and pass the bar.

Have a listen to the podcast Startups for the rest of us. All about bootstrapping. Get inspired and start building.

No. I spent some of my money while I was employed on contractors but it didn't work out. I am back on my own as of April 1 however I had a medical issue that lasted ~5 weeks with a few bills to go along with it so I am currently contracting to make money to pay those. The unexpected expenses were ~20% of my runway so I didn't feel comfortable just trying to absorb the cost. I also missed out on a conference I intended to attend.

> raised 180k with TinySeed

That is awesome - did you invest all of it in hiring?

> 8 full time at Activity Messenger and doubling year over year

Very impressive! Congrats. Turns out we're in a similar space (as are several dozen other companies, as I am sure you are aware). JackRabbit is one of my customer's most common platforms.

They bullshitted the right sounding bullshit to a specific audience who absolutely laps up particular flavors of bullshit. Sometimes the flavor changes (e.g. DevOps, enterprise SaaS, crypto, AI), but they’re always hungry.

You of course don’t have to raise money if you don’t want to, but I’m sure you could do it too for damn near any idea you come up with as long as you also figure out how to relieve yourself of any sense of self-respect and prostrate yourself in front of the altar of VC buzzworthiness and tomes of fortune cookie wisdom.

My entire career was spent building valuable software for companies to generate large profits only for me to be laid off (and fired, once). After the firing I was quite angry and probably a bit arrogant.

I went on a bit of a rage.. "I built the most successful product there, I can do it on my own."

So that's what I did and I haven't worked for anyone else since (on 8 years now).

1) Start by picking your customer. Pick a customer that is easy to find and has a clear channel to access them. For example, maybe I want to target sales people. I know a lot of sales folks use LinkedIn, seems like an easy channel to them. edit: Also, pick a customer that _pays_ for things. B2B-type customers. You don't want to be selling a product to teenagers, developers or anyone that doesn't like to pay for solutions :)

2) Don't invent anything new. Pick a well established idea/business that is already being done (and most importantly, people are paying for). Continuing on the sales example, I know sales people often pay for technographic data. There are plenty of SaaS products out there selling that kind of data. I build a list of them.

3) Scope the product down to its bare essentials. What exactly are the sales people buying? The products probably have a lot of fluff that isn't needed. Get rid of it. This is a good time to talk to the target customer. It can be nice to hear their complaints about the products they are currently using, etc.

4) Finally, build the product and ship it. Get the initial version out quickly and keep refining it.

It used to be knowledge was locked up in books and putting them in libraries for free access was revolutionary, but libraries don't compare to the knowledge transfer benefits of view source in terms of cost and ease. (Obv libraries have a wider base of knowledge to distribute.)

Even today, with all the obfuscation and minification, devtools offers a lot of the same benefits as "view source" did.

So I opened the inspector to remove that event handler or whatnot.

My girlfriend was sitting next to me. "What are you doing?", "Oh, just need to edit this so it allows me to continue." The look on her face was priceless. "You-you c-can do that?! You're allowed to just do that?!" To be fair, I can understand her apprehension as I was wearing a balaclava and black gloves.

I just overwrote `window.hasFocus()` to always return true in the browser console.

This felt (and still feels) like magic.

In this wonderfully written and inspiring piece, perhaps we should consider that the real issue isn't the individual's capability but rather that their potential has been misdirected or they haven't been in environments that recognize and cultivate their unique skills.

Every fantastic senior dev I have worked with has been laid off several times. Our industry is not immune to companies failing. You shouldn't discount people just because they've been laid off.

I'm a scientist, and I've often thought about how the work I and others would do would be different in different funding environments. That's the same idea of people's "potential [being] misdirected" that you are talking about. People often chase the newest shiny things and follow the money for both hiring and funding, but that isn't always good for both the people themselves and for innovation as a whole. We need to make it possible for people to develop their talents and skills, whatever they are and even if they don't match the current needs or desires of the environment, so they we have experts and experienced folks when the time comes for those innovations and technologies. It's the same idea as diversification in investing, with more agility and resilience gained from a diversity of skills and experience. I hope more funding managers and hiring managers realize the value of fostering people's potentials rather than focusing myopically on supposed current needs.

But they are being paid a lot more than they would get, helping people.

While i'm unsurprised to hear that such a sociopathic and non-scientific narrative exists from hiring managers, I'm curious how they find out whether a departure was a layoff. For big companies, sure, you can probably tell that if someone left various tech darlings in late 2022 that it was probably a layoff. But like outside of that, how the heck do you know? Are you googling "$coname layoffs $year" for every entry on a resume you're screening or something? Or are you literally just asking them "tell me why you left each job" and people are for some reason answering honestly?

This just seems really hard to actually pin down unless employees are volunteering the information. Even if you did leave right on a publicly-known layoff date, it seems pretty easy to just explain that "uh yeah they were doing so poorly they laid off X% of people, I left for greener pastures". Or that general sentiment but passed through 1 or 2 layers of word-smithing.

This was it for me. Pouring your whole self into your work, only to be laid off, fired, or skipped for promotion is soul shattering.

$400k ARR solo. I'll never work for anyone again, I'll never feel compelled to be a yes man again, I'll never fake a smile for a drooling idiot of a C*O again.

That said, after about five years of that, I'm ready to get back to working for myself.

As you are an expert in SEO, and I'm building a SEO-adjacent product, I would love to pick your brain. Email in the profile.

Can't really argue with that :-)

Pissed me off, something fierce, being treated that way (especially as I figured out it was being supported from the C-Suite). However, I have since realized that it was probably the best thing that ever happened to me.

I enjoy writing software. So much, that I will do it for free.

When no one’s paying me, I get to do it the way that I want to do it. No scrum standup humiliation sessions, no deliberately writing terrible software, so terrible programmers can understand it, no being told how lucky I am, to be “allowed” to work.

Basically, after 10 years, you have three choices: become a consultant (I hope you like being a salesman), become an entrepreneur (I hope you have a good idea and a lot of savings) or get into management (I hope you love herding cats and playing politics)

There are outfits that realize that you get better with experience and want to capitalize on that. Unfortunately, they seem to be few and far between.

We have a DevRel engineer specifically working to get technical debt tickets into sprints.

So you get to refactor! Oh gee!

I know a guy that had podcast in 2009 or so. He had great timing but the problem is his podcast completely sucked and he has nothing interesting to say in general.

Shifting things forward or backward in time would not have solved anything.

Two massive parts of success in entrepreneurship are luck and doing something others didn't want to do, or didn't think was worth it. Both require showing up.

Having a world-changing idea is an overrated and oversold approach. Some people make billions selling underwear or bottled soda. You can make millions out of selling literally anything.

What are the insights I gained from this particular piece:

* self depreciation is funny if done in earnest

* note that the OP had a huge handicap (not knowing to code and ignorant of web technologies) but he was not clueless: he had deep knowledge (at least deeper than most site operators) about the ad business and how to monetize

* building up from the above, he innovated in an area what he knew, i.e. ads. He didn't try to jump into the idea de jour. Too many first time entrepreneurs miss this point.

* he used simple tools and approaches(e.g. Yellow Pages, source view) but used them effectively. Didn't try to go after shiny tools, e.g. get on a bootcamp to learn web frontend development

Overall vibe (don't know if it's a persona or the real thing, judging from the wackiness of his ideas I'm guessing the latter) from his writings is a person who you'd want to grab coffee (or beer) and just hang out with.

After getting laid off, I decided to roll the dice instead of looking for another work-for-hire. Yeah, it's too late, but I needed this just to get excited about technology again. I was seriously jaded from debugging the microservices spaghetti at every frigging job, trying to make a pile out of water and not actually building anything.

I torches through my savings, and no regrets. I am in my 40s, and the time to take a chance is running out.

The point is, there is such a thing as "right place, right time". The idea and the execution have to be well-timed. It might be too early, or it might be too late (as it was for me). Take The Globe, for example - the Facebook before Facebook. They failed because a) there were no phones b) not enough people online to get the network effect. Similarly, good luck getting your "crypto" getting traction at this point.

If you have an idea, and you think the time is right - take the chance. Not knowing what will happen is part of the fun. Don't look at it as taking risk, look at it as rowing through a river and without knowing where the river goes. If you don't row, you will never find out what's around the bend.

I think you kinda need to re-evaluate your relationship with uncertainty when doing something like this.

As a wagie, unexpected news is nearly universally bad news (layoffs, corporate mergers), whereas the status quo is neutral-good.

When you're starting up a business, unexpected news can be good (new customer, new investor), but the status quo is neutral-bad (slowly running out of momentum and funds).

"The company's IPO made history when it posted the largest first day gain of any IPO with a 606% increase in price.[3] Early in his tenure, Paternot became known in popular media as "the CEO in the plastic pants" after he was filmed in a nightclub saying 'Got the girl. Got the money. Now I'm ready to live a disgusting, frivolous life.'"

Then they lost everything in the dot-com bust, but is this really failing? They had an idea and probably made life-changing money. theGlobe failed, the people behind it have not. They unlocked the next tier of freedom where they can work on anything they fancy and drive a McLaren to work. I hope to fail like them.

The right time is defeatist nonsense. It's like the stock market: you can't time it, so just enter and stick with it. Hindsight is a useless tool to entrepreneurship.

Let's not blame anyone and just admit that for many "... maybe it's just not for me."

I find too many people blame themselves or others instead of just changing angles in life.

This is a perfect example.

Total admiration for the author, it was very savvy to identify that opportunity and they put their money on the line. The modern self-made entrepreneur is less appealing. Success stories nowadays are like "We dropship japanese candy boxes" or "My Crypto Substack has 5k subscribers".

If they were really in it for the money then spending all of their free time for a couple of years to get a few hundred dollars MRR would be a fail, yet many of them keep at it. I suspect the rewards they get from being an active part of the community feel worth it.

I think a better choice is to either go day job + hobby that isn't for money, as restricting yourself to what makes money is going to be less enjoyable. Or day job + heavily profit focused side business with the goal of quickly replacing your day job with said business, then freeing up some time to have your hobbies again. I think the mistake is trying to do both at the same time. You can't really focus on both profit and personal enjoyment in the same project (unless profit is a big source of enjoyment for you).

Anyway, I do think we have already seen the bottom of that curve.

Who are the top players in pest-management software? How much of the market do they have? How much of the market wants another application because the existing ones don't cover their niche? How easy/difficult would it be to market to them?

I pulled Pest Management Software out of my ass because about 20 years ago I responded to a similar attitude by mentioning that while gardening I wondered if there was such a thing as pest management software (there is. It's a huge field) and also because last summer I was asked to build a small wireless interface to a mosquito sprayer so -- wait for it -- someone's mosquito control app could automatically monitor the amount that was being sprayed without the driver having to enter any data.

Opportunities are everywhere but you won't find them unless you look.

you probably won't start ranking as easily as you could have 10 or 20 years ago, and there is lots of competition these days — that's true.

It really supports the perception of seeing a door closing just meaning you need to change direction and not to take it personally.

A weird mix of inspirational hogwash ("here's how I succeeded and you can do this too!") with some pretty crappy tactics, like domain squatting, crap ads business with no value added, and lying to customers to not let them know they could have cut the middleman.

Basically nothing this guy is explaining ads any value. He had little to no expert knowledge, he just got lucky with some low hanging fruit (mostly because his customers were even more clueless than he was).

No doubt he's making money now and is "his own boss" now, but nothing he did to get there seems inspirational or worth copying.

(Not a video game)

It may or may not end up being a niche product, but that isn't necessarily a bad thing.