I'm having trouble replicating my own success from that era. Everything is more complicated today: the development stacks, the competitive landscape, the vast increase in regulations and liability around handling data, the move from an open web to social media silos and mobile apps, scammers and bots winning the spam wars and destroying most online advertising. I still have businesses I started in the 2000s and early 2010s that are very successful, and not so much that's newer and doing as well.

My non-tech ventures are doing well which is nice for a change of pace after decades of coding, though. I bought a bunch of relatively cheap (3-4 figure cost) manufacturing equipment and turned a spare bedroom into a workshop for designing and creating physical goods. I have a line of home decor that sells well enough that I'm dropping a stack of packages off at the post office 5 nights a week.

> the vast increase in regulations and liability around handling data,

Can you elaborate on this or give examples where these bigger hurdles than they used to be? I'm curious to know in what domains this is the case. I've no doubt that it is true, but my sense was that there are still large swaths of "internety" products that are entirely or mostly unregulated and where there isn't much to be said about how you handle data, but I could be wrong. I'd be very interested in any concrete examples you may have had in mind.

Much of the clear low-hanging fruit are in automating or aggregating fragmented data in tech-neglected industries, and that often involves handling PII or payments data - which quickly exposes you to GDPR and equivalents in every country, for which there isn’t a obvious path to compliance (especially when considering that web tech trends go the opposite direction, like the trend toward edge computing = how do you satisfy data residency requirements? It gets complex fast).

GDPR-like regulations certainly come to mind. Which is a good thing - too much unprotected data in one place is a disaster for all involved.

And that's one of the areas where there's a lot of innovation happening right now... for example, the push to decentralize identity ensures that businesses don't need to keep any data that is considered personal data under GDPR while still having provable "credentials" (things like proof of age, degree, medical records etc) needed to be provided with certain services. I won't link any particular businesses in this area, but a quick search should show there's a lot... and the European Commission is one of the leaders in pushing this: https://ec.europa.eu/digital-building-blocks/wikis/display/E...

This is actually really interesting to hear.

I always hear the argument "you don't need a fancy website or UI, when I started my site/app looked like ___"

These people created MVPs in 2010. You're now competing with MVPs that can be built with way more features, the latest tech stacks, and more in the same period of time.

This can proably be attributed to the barrier for entry for competition being so much lower , so the definition of an MVP has changed. And equally, expectations from end users have risen. Recent anecdotal example of this is the frenetic pace of development in the ML/AI space with opensource tools like Stable Diffusion practically almost rendering moot the business model of OpenAI’s DALLE-2.

To win out MVPs have to either be a value proposition currently not available that people need, or to win a popularity contest based on UX, design and branding. That there are still project management tools being developed and succeeding in a saturated market tells me that the popularity contest never really stops.

I also had a successful SAAS around that period while my later ones failed.

Start a SAAS in a new market, not an established one. Back then every market was wide open.

>I have a line of home decor that sells well enough

Seeing a pattern here, feels like an oversaturation of software and not enough physical assets to connect it to. Mostly people also get tired of shipping code all of the time. Thats why the naughty secret dream of a lot of devs is just to do a coffee shop or a non-automated bakery when retired :)

Do you have any suggestions for Etsy seller communties? I have a friend who has a bunch of professional printing and cutting equipment, but the niche he sells in is very small - most of his business coming from word of mouth - and very seasonal. I feel he could be more successful expanding into slightly more main stream areas.

It seems like "mid 2000's was the perfect time" because these fortunes take 10-15 years to get to any meaningful number.

These opportunities exist today, it just starts out with really low numbers in a niche that everybody thinks is super boring and takes forever to build up organically.

> The key takeaway for me was that the mid-2000s were the perfect time to be a founder of a software tool. I can’t help but feel that there are so many tens of thousands of similar stories without such a successful conclusion.

I think the takeaway should be that the mid-2000s to now was the perfect timing to succeed as a bootstrap if you were going to. In 2040, with the same survivor bias, people will probably say that 2022 was the perfect time to be the founder of a software tool.

+ hindsight bias :) but you are totally right. Also it was harder to start a tech business and thats why many people didn't do it. Folks at Hot'or'Not had to literally borrow money to finance the servers which they had to go and provision physically.

There are apps that look like its 1999 and make 30k a month. Sure its not $15m and not the next google but opportunities are there. We are just pretty bad at recognising and solving problems that are outside of our bubble and that is where the saturation is. Your local plumber on the other hand...

> The key takeaway for me was that the mid-2000s were the perfect time to be a founder of a software tool. I can’t help but feel that there are so many tens of thousands of similar stories without such a successful conclusion.

The key take away is that any companies that survive for 15 years or more make money or go bust.

So true. By the time I graduated in 2012, it was already too late. My first commercial side project failed. There was just too much competition and they got too much funding (I had 0 funding). I already felt that most opportunities for bootstrapping had dried up at that point and so, as a last resort, I decided to try the open source model and had some success in the sense that my open source project got a lot of traction initially.

Unfortunately growth slowed (Google traffic ground to a halt) and there just weren't enough users to monetize. Felt like the door got slammed shut right in my face.

Timing and luck is everything.

I don't think that there's a perfect time for anything. I am of the opinion that there will always be room to create stuff, it's just that for certain categories the preparation time will be longer.

Building an MVP will just take longer. So rather than measure the time to a workable MVP in weeks or months, for a product to stand out as being valuable it would probably take a year or more for users to want to consider making a switch.

In fact, I'm working on something vaguely similar to BW on the side. I don't know if I'll succeed or not but I'm loving the research I've been doing so far.

I understand it as the effect of new technology. The internet was still very new in 2000 and we've all witnessed its potential expand into what it is today.

New technology creates new and ripe frontiers. What new technology exists today that unlocked something for the human race? You'll find the opportunities there.

Mid 2000s might have been harder. I think more people are willing to pay a subscription for a thing than back then.

I think 2008-2012 was the sweet spot. Building your product in 2008 for 2 years would have taken you to 2010 when SaaS was more mainstream., but still relatively low competition.

Mid 2000s though would have been the best time to start an internet startup though (ie TripAdvisor, MyFitnessPal) given the low competition in search.

There's still no competition now compared to any time in the future for an internet business.

What do you mean? Give me some examples. There are plenty of saturated niches.

They will always be niches that certain people deem to be saturated, but that won't stop a determined entrepreneur from starting up a new venture.

If you went back to January 2007, the iPhone didn't have competition from Samsung's flagship touch-based phones or Google Pixel (because they didn't exist yet). This was a time when Nokia, Blackberry, Sony Ericsson etc were the dominant phone makers and Steve Jobs' original goal was to capture 10 million sales/year with the iPhone, out of the massive mobile phone market.

If you went back to January 2004, the Tesla didn't have competition from Ford, Porsche and any of the other ICE car makers that have now announced EV models in their line up. In fact, investors would consider you stupid for asking them to invest in a car company or even one that planned to use batteries because of how messed up the economics of EV production was at the time.

All certainly true. My point isnt that its inpossible and that you shouldnt try, its just that it is much harder than it was in the past.

And my point is that, that is a weird way of looking at it, because _now_ it's also the easiest it'll ever be, what does it matter if it was easier in the past? The past is gone.

Grandfather was talking about how hard it was in the past, and i just commented on my experiences in the past. Of course looking at the past is not actionable, but I never intended to give actionable advice - just provide a comment

Also, saying it will be even harder in the future isnt exactly actionable or substantial advice either.

He means "if you think things are crowded now, they'll only be more crowded in the future"

I mean thats obviously true?

On the other hand already successful corps were acquihiring like crazy at that time. You didn't even need paying users. A big "BETA" next to your web 2.0 shiny logo was still required, though.