Being laid off and unplanned entrepreneurship | Hacker News Reader

Being laid off and unplanned entrepreneurship

deepsouthventures.com

396 pointseightturn162 comments

Had an epiphany like this after an earlier startup project failed, which my cofounder and I had tried to do following the formulaic approaches advocated by various accelerators, investors, and experts (often people with zero experience running a startup, but had been involved as angels after BigCo stock options vested, and then got into mentoring local accelerators).

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).

> but also good health insurance.

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.

Yep. I’ve been saying for awhile now that universal healthcare would likely lead to one of the biggest small business booms ever. Not only does it help people strike out on their own, but makes easier/cheaper for them to hire.

Same for housing. In Tokyo median rent price for a 1BR is $600-$700. No onerous contracts either with month-to-month rental options. The freedom to explore creative and business endeavors without these worries cannot be overstated.

On the other hand, it would make it harder for big business to retain talent.

You mean they would have to offer a good job with competitive wages, enjoyable work conditions, good benefits (mat leave, paid time off, sick pay, etc.) and a good career path?

This is a feature, not a bug.

This is why big business is not an ally for anything that makes health care cheaper or easier to engage. It's a great system for them.

JP Morgan, Berkshire Hathaway, and Amazon, all huge employee counts, together seriously tried to tackle healthcare costs in the US.

I'm going to be honest, I don't believe this at all. It seems like one of those things that everybody says because they want it to be true.

Ya. It sounds good. But then the question is why doesn’t every other country destroy US in entrepreneurship? Why does US still have so many small businesses?

Exactly. I'm willing to bet that the US may not be the number one country in terms of entrepreneurship, but it's certainly not at the bottom.

Well obviously there is more to it than just UHC. The US encourages and rewards risk taking, and has a healthy funding culture not found anywhere else, etc... But, I believe if you take how good the US already is with entrepreneurship and then add UHC it would trigger a boom.

People don't appreciate how expensive health insurance in the US is. A high-quality PPO plan for a whole family on the open market can cost $4k/month.

On the other hand startup culture and entrepreneurship are much more common in the US, compared with the EU. But the latter does not tie health insurance to employment, in most countries. Probably other factors are more important.

Doesn't mean Universal Healthcare wouldn't be a net win for entrepreneurship.

We should unlock all barriers to entry that we possibly can

Universal Healthcare in the US will negatively impact entrepreneurship.

Why?

IMO, one of the reasons US has done better with startups is because there are people driven by the difficulty of life. Make life easier and I think some of that drive will go away. US has had a good (although somewhat difficult for the people) balance for some time now. It's just an untested theory of mine.

Sorry, but this is just total nonsense.

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.

It's a net win for everyone except the middlemen.

I think to have an honest conversation about universal healthcare is to admit that it would cause health care rationing. Costs would be tighter across the board, and the best experiences of health care services enjoyed with (many) corporate plans would degrade, relatively speaking (unless supplemental private insurance continues). Doctors would probably make less profit, not just insurers.

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.

I don't think so. I think it means other factors are also very important.

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!

It really is a detriment to entrepreneurship in the U.S., as well as early retirement for those who have saved up enough money but are locked into a job until Medicare kicks in at 65.

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.

This is the whole point.

What are some good examples of countries with a different healthcare policy and more entrepreneurship, small businesses, and/or craftspeople than the USA?

Taiwan has a solid national health insurance plan. The number of small and medium sized businesses is very high for a country with a working age population of 16 million people:

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.

Alright here are three health care reforms that we could implement without going all the way to Universal Health Care:

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.

Those are fair. But why impose them through regulations?

Entrepreneurs see business potential on this arbitrage opportunities.

Well, for starters, two things come to mind:

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?

Is that universal healthcare with extra steps? Almost, but on a serious note, why not go all the way with universality?

Because universal healthcare is not the best solution, as is becoming increasingly evident in Canada and the UK.

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.

> 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?

Most ER visits are not life or death situations, and most would make a 20 minute drive over a 10 minute drive if it meant saving $1k. So the incentive is still there. You can say that I'm valuing money over lives in this example, but I think we'd be picking the lesser of two evils, as it's becoming increasingly evident that socialized medicine is stacking up its own body count. Working with society is all about incentives, and universal healthcare doesn't incentivize excellence, it incentivizes complacency.

What non-emergencies typically bring you to the ED?

Sick kid during the weekend

I needed* to be stitched up at 9 PM. Urgent care could have done it, but they were closed.

Those aren’t mutual exclusive. In fact having healthcare not be gated to the single few that can afford it might accelerate the process of fixing the issues around pricing.

How is the typical person supposed to decide the best path of care? How do you incentivize competition while keeping standards of care up so that people receive good care with highly complex tradeoffs.

Or just have Medicare for everyone.

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.

All else being equal, I'd rather see the pricing pressure done by market competition rather than enforced price caps benchmarked against some metric controlled by the industry (see Medicare Part D - gov. negotiates hard to only reimburse xx%, drug industry says fine, we'll just raise the book price - you'll get your talking point, and we'll still get our asking price).

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.

It’s not as easy in reality as theory.

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

Regarding #3, do you mean in the United States? That's not generally true. Your health insurance premiums, under normal employer plans, are not tax deductible, but they are paid pre-tax.

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).

Paying something ‘pre tax’ is equivalent to, or even better, than it being deductible.

4. Go back to county hospitals. If you want to pay extra for the Cadillac plan and go private good for you. But let them compete against the county just like the 80s and prior.

This is not an accident.

This is highly dependent on where you live. If you're unprofitable, you can qualify for Medicaid and various state benefits. If you're profitable, there are strategies that can make nearly all health care dollars tax-deductible.

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.

The career accelerator people kill me. Honestly why do I want to hear from someone who's biggest risk was getting a job talking to people taking big risks.

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.

> The career accelerator people kill me. Honestly why do I want to hear from someone who's biggest risk was getting a job talking to people taking big risks.

Professional talking heads will always try to convince you they are needed.

The harder they're pushing, the more suspicious I am. If they were needed as much as they'd say, why would they need to persuade me so much?

> 3) The product must generate revenue from day 1

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.

Most obvious thing missing is your hosting provider and how much control you want there (SaaS, PaaS, IaaS)

Would love to know more about how you did step 1. What tools would you use or would you use today if you were in a similar position.

Any chance you can share? I don't have a particular project I need to pay a consultant for right now, but I'd be honest: if you wrote a book, I'd buy it and put it right on the top of my reading list.

> I didn’t raise any money for these projects. I funded them with my 9-5 salary. Solo. And the reason for that was simple – why on earth would I vehemently abandon boneheaded micro-managing layoff kings in the 9-5 world only to raise money & adopt a board of boneheaded micro-managing layoff kings in the startup world. If I’m gonna build, I’m gonna have free-rein decision making to pursue any and all ludicrous business models, with no oversight. If I fail, fine. That’s on me. If it works, son-of-a-gun, my job will feel like play.

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

appreciate that, leetrout (Peter here)

Your thread is 9 months old. Do you have a product and a bit of traction? I was in a similar place to you back in 2019. Via side gigs I built a product that served a niche. Eventually, raised 180k with TinySeed (specialized in boostrapping B2B SaaS). Best move ever. Gave me and my cofounder a runway to find product market fit. We're now 8 full time at Activity Messenger and doubling year over year.

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

> Do you have a product and a bit of traction?

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.

FWIW… look at the portfolio pages of lots of VCs. They’re absolutely filthy with boring companies with boring products that obviously have absolutely no prayer whatsoever of being a “venture scale” business. Despite that fact, they managed to get multiple investors to put in Millions in capital. How?

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.

I respect the part of diving in to build something on your own.

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.

I mainly 'leeched' the table, tr, td row design aspect, as I had no idea that existed.. fwiw, I didn't copy anything else (text, images, etc)... that 'scaffolding' was helpful until I discovered Wordpress. And I dislike ads just as much as you. I usually just put 1 or 2 on the page. no popup nonsense or 'blasting' ads, ha. Now, since I sell onions in the internet, I'm the one often advertising on these types of small niche sites, and they tend to perform better than larger properties... either way, my 2c. (author here)

But isn’t software engineering one of the easiest domains to self-learn? I don’t know of any other profession that has such vast amounts of completely free resources online.

The amounts might be vaster than most, but it’s hard to imagine that any profession doesn’t have enough free resources online that can get you into it.

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.

I'd disagree that really learning it and being proficient is any easier than other domains. People may have impression that it's easy to pick up since the number of 20 minute python tutorials vastly outnumbers 20 minute heart surgery tutorials, but it takes a long time, hard work and good mentorship to really pick up. A formal education helps as well, just like in other professions. You can self-learn carpentry or accounting or physiotherapy, but just like with software engineering, a good (!) proper education brings you further and quicker.

I can relate to this, though I came into it already knowing how to do the coding part. I had no idea how to do the rest of it.

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).

I'm right at your starting point. Can basically build anything but committing to an idea is the sticking point. What product would you want to start with today?

Reach out if you want to start a conversation. I'm thinking maybe a Slack for people at this stage. My email address is in my profile.

Sent an email.

What would make it different from other messaging platforms?

I think they mean, "I'm thinking of creating an instance of Slack that people can join and chat who are in this stage of their journey", not that their idea for a new company is like Slack.

That makes much more sense :)

Sent an email as well

I'm unsure if my advice is any good, but it's what worked for me. Here's the general thought process/flow I use.

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.

That’s impressive,

If you don’t mind can you share what have you built

View page source is, as was mentioned in the article, magical. The fact that by publishing something online you make it available for everyone else to learn from is astonishing.

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.

(author here)... I honestly was scared of it first, as I thought if I edited the code, I'd accidentally change/update the other persons website...

Few years back I ordered something from the internet. I forgot what exactly went wrong, but some JS nonsense prevented me from doing what I wanted to do and I no choice but to use this website.

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.

> To be fair, I can understand her apprehension as I was wearing a baklava and black gloves.

Was it sticky?

Have you ever had one that wasn't? That said, I'm going to go eat some balaclava now.

Last time I unchecked a radio set I was wearing a black hoodie, so you're not wrong.

> I was wearing a baklava

Like this guy?

https://www.youtube.com/watch?v=YtqKIa_WFNU

I used to do the same with some online-training videos which would stop when I de-focused the browser window.

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

This felt (and still feels) like magic.

I saw in your "Moi" page a great emphasis on the domain name. I agree with you. I think domain names are the crystallization of an idea, a message. On the other hand, I see a lot of people from startup bubbles in X making fun of domain registration, suggesting that it is a "low bar" activity and doesn't represent any effort toward building a product. I disagree with this point of view. To me, the name is bound to the vision of a product being used by its customers. I cannot imagine something being used without a name or ID. I believe good names tell a story.

great .com domain names were the cheat-code I was blindly searching for. The unfair advantage they present allowed me to compete head-to-head with larger entities. I still play in these waters.

I've often heard the narrative from hiring managers over the years that a prospect who's been laid off probably doesn't make a good hire, especially if they've been laid off multiple times.

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.

Your post reminded me of some thoughts I've had about a similar topic over the last few years.

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.

This makes me think about all the psych grads, that went to school, wanting to help people, but are now writing dark patterns.

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

That's a great example of this kind of problem. People are pragmatic and take the jobs that are available, even if that it's not what they originally planned for or what would be more helpful. I've done the same myself a few times.

> especially if they've been laid off multiple times.

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.

"often heard the narrative from hiring managers over the years that a prospect who's been laid off probably doesn't make a good hire"

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.

> I can’t trust them anymore; I gotta figure out a way to generate revenue myself; from my own business; that I control. Online preferably.

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.

Never say never.

For real. I made $400k+ multiple years working for myself in a business that was a mix of product and services. But then divorce, business changes, and my own values shifting pushed me to get a tech job where I made even more, working less, with less stress. It was a great move, though I had to let go of some of my ego to do it.

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

This just shows that life is really transient. Life circumstances change, so we probably shouldn't be dogmatic.

Frankly 90% of people probably are not cut out to be entrepreneurs because it requires certain qualities.

I love the name 'unplanned entrepreneurship'. After a year of not being able to find decent work, I decided I might as well build something of mine, and slowly grow it to profitability. Which I did, and it's still not profitable, so I have to try the job market lottery again—which has killed a lot of motivation and momentum, but I'm back at it for the long haul now.

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.

thank you sph... it took me a while to cobble together a title that made sense.. and I'm far from an seo expert.. I learned the basics and sortof winged it from there.. ping me on twitter.. I hang out there usually..

During the interview at the last place I worked, the owner described starting the company (20+ years earlier) because he got tired of being laid off. Figured that the risk of his new venture failing was probably on par with getting a job and being laid off again, so why not go for it?

Can't really argue with that :-)

As a fan it's strange to see no mention of vidaliaonions.com

author here : ) that came after DudeRanch : )

Oh wow. I'd read that post before but didn't make the connection to this one. Well worth a read as well:

https://www.deepsouthventures.com/i-sell-onions-on-the-inter...

thank you senkora (author here)

For me, I found out that us “olds” are not exactly loved (actively hated, more like), and gave up looking for work, after being laid off from one of the top imaging corporations in the world.

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.

I quit a company that was showing all the signs of trying to get rid of its senior developers so a couple of us jumped ship before the inevitable layoff. I went straight into another place that the recruiter said "preferred to hire more seasoned engineers." In my 5 years there I only remember two engineers that were under 30. Median age probably hovered around 50.

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.

Assuming the pool of engineers is growing exponentially, I’d expect a very small population of seasoned engineers.

I think that's why we got the two younger ones. At that time, they couldn't find enough experienced engineers to hire, so they tried two that were fresh out of school. They were pretty bright, but left after about 3 years each.

oh but think of all the “refactoring” you’re missing out on.

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

So you get to refactor! Oh gee!

What is sad is that "olds" in software engineering means 10-15+ years of experience. I started in this career at 19, and around my early 30s I found myself at the apex of my experience, mental sharpness and talent, while pretty much any company finds me too experienced, too expensive and perhaps too hard to train and mould into shape.

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)

Sometimes we're just not built for the classic corporate environment.

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.

Were there other sites between AppalachianTrail.com and DudeRanch.com? Seems like a big jump from $3k to $17k, for something that, in my opinion, doesn't seem like a sure winner worth 5x the first one.

I sold AT for $30k, and primarily used the proceeds from that to acquire DR.. I was still working 9-5 then also, so I was prepared to spend upwards of $50k to acquire DR (as that industry seemed like a good fit for me) (author here, fyi)

The creativity displayed in spotting the opportunities is really impressive.

Appreciate the post. Was in a similar situation myself - always wanted to be an "entrepreneur" but ultimately, needing to survive to feed the family is what kickstarted it all. I really appreciated how, even though you didn't have a technical background, you found a path that works for you and even more so, focusing on what you CAN do vs what you CAN'T do. And sometimes, you do get hosed on a deal at the start before you establish trust and credibility and then eventually learning your way around the trade.

Like many things with the internet, it seems like if you got in at the ground floor you could do something like this. Now everything on the internet is cordoned off in centralized spaces, and there's a million businesses and random guys trying to figure out any and every possible angle to monetize overlooked markets. No way I can convince businesses to pay me for ads when they can be paying Facebook or YouTube who own practically every eyeball on the internet.

The frontier is always moving. You don't see people looking for gold in California anymore.

You also can't assume you would strike gold just because you have a pan and the right timing.

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.

You certainly won't strike gold by saying "there is no gold to be found here" and sitting on your bottom.

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 a beautiful piece of writing, which hits close to home for me, as I've always kind of managed side projects and my full-time jobs during office hours.

really appreciate that dsco (author here)

Going on a slight tangent with unplanned entrepreneurship, the Korean PC cafes had their roots in their owners being laid off from their corporate jobs.

Peter, if you read this comment I suggest that you start writing a book immediately, if one's not in the works: your simple but thoughtful writing style is awesome and makes the deep insights you provide even more delightful. I, for one, plunk down money to read 200 pages of this stuff interested with anecdotes from personal life.

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.

thanks Jun8... writing these small essays is taxing (but rewarding) - I can't imagine what it's like to write a book (unlikely). If I ever do, it'll be similar to how Derek Sivers writes (short chapters)... no persona here, though.. just someone who's been laid off a lot, and channels William Faulkner style of writing..and also, hard to write a book when I've got onions to ship!! : ) (peter here)

That is an inspiring read. I almost went down this path when I got laid off last. I still somewhat regret taking up a corporate job back then instead of focusing on something else. But then, I probably wasn't ready. Thanks for writing this Peter.

thank you darkstar (peter here)

This line in the article sums up beautifully the desire for being an entrepreneur: "A path to avoid someone else’s bonehead business decision which kneecaps a company and executes my career."

Interesting and strangely uplifting story!

Gotta admire the hustle and will to be independent.

thank you HarHar (author here)

this is highly dated... 2004-2008, the opportunities were others than today's

> highly dated

Article is published:

> June, 2024

I don't understand what you mean.

Most of the stuff in the article happened between ~2003-2010 at first glance, which is what he means probably (even though it was published in 2024.)

(author here) just published this story today, correct.., been writing it for months, as I've been forgetting all the weird steps I took to get here..

The initial events described in the article happened around 20 years ago.

The stories presented are from an earlier era but maybe still relevant.

but the story took place in the early 2000s.

The opportunities are different, but the attitude of keeping your eyes open to opportunities and figuring out what works is still true.

It is so noisy and crowded that I wonder if it is worth spending time and energy looking for opportunities.

Is it?

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.

We are at a low point, where everything is gated and huge corporations will decide to scare your customers away. Of course, there are always lots of opportunities. But currently they are fewer.

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

This attitude is bad, but it is kinda justified. If you spend any time in the "indie hacker" entrepreneur space today it is oversaturated with people trying to root out every single angle they can possibly try to address with their tech solution. They are all listening to podcasts, newsletters and buying courses about how to be a tech entrepreneur, but the people selling the 'how to get rich' info are the only ones consistently making money.

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".

I might be way off the mark, but I get the sense with a lot of the indie hackers it is less about the money and more about the attraction of the community and the sense of belonging. If you "build in public" you'll get attention and will be cheered on by the others doing the same.

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).

as someone who's living off of the tiny business income, there are plenty of opportunities to be found on the internets. some of these opportunities have a shorter shelf life than others, and that's okay; you can still make a killing before moving on to the next wave.

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.

I'm still stuck on how someone makes it through a history degree without enjoying reading.

when my senior year rolled around, I still didn't know what my major was going to be. I visited a guidance counselor, and she viewed all the classes I had inadvertently taken, and I'd fulfilled 3/4 of a History degree (a Southern History degree, no less - they offer it at my alma, Ole Miss). So I just went with that and read a few more William Faulkner novels : )

I went from an EE major to Aerospace. Realized I wasn't going to make it. At the same time the market for aerospace graduates was collapsing. But I did have enough math and programming credits to graduate with a CS degree. And dumped those aerospace credits into an Astronomy minor. Sometimes the degree picks you.

Funny how this goes in the US. Sounds like a better system, curriculum-wise. In Europe, in many cases, one would need to fully start over.

I was putting off starting my SaaS idea for years (has to do with assigning code reviewers based on specific file patterns and notifying them on Slack) but the idea was much more marketable 10 years ago when I first had it. GitHub did not even have the concept of CODEOWNERS back then.

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.

> 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).

> Take The Globe, for example - the Facebook before Facebook. They failed

"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.

Stick with it on who's money? Not everyone has the luxury if failing multiple times - you need to at least weigh your odds.

The head of Gupta Media (friend of mine) started his solo journey with a layoff.

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

Really inspiring read. I've been thinking about doing something similar but I always give up early and do not believe in it.

really appreciate that amunozo (author here)

I hate this kind of article.

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.

I run a chatroom for solopreneurs in case anyone is interested codingbutclueless.com

I tried going solo out in Berlin after a few years working for a couple of the biggest douchebags you could imagine. Same idea - I didn't like having to answer to a douchebag every day, and didn't worry myself about getting FAANG money, so I tried a B2B start-up that tried to automate some compliance issues that most companies out in Germany face. Didn't get the product market fit right, but learned enough to get me in front of a FAANG-adjacent company who had an opening and that was that.

Ah yes, how our cozy internet of sharing was infiltrated and ultimately ruined by people looking to simply earn a living. Bigger players took down smaller ones (ruining things further) until we eventually stopped making websites for them. Earning money was replaced by fiat-like pyramid schemes. The remaining scrap was quickly "copied" into LLM's and soon I'm sure there will be all knowing humanoid robots walking around. What comes after that?

The old and trusted face-to-face human interaction.

And then?

You must be fun at parties!

We take up arms against a sea of robots. And, by opposing, end them.

And then?

Psst! I think this guy is a ROBOT.

I for one would appreciate a list of "software products that the world needs and if you made this then you could make some money".

(Not a video game)

I need a software that do my work while I play guitar.

Build what you feel the world needs, instead of what you think other people think the world needs. It's much harder to guess what the average person will want than what you want. The world is big, so odds are other people will feel the same.

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

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