A spreadsheet of the businesses I've started over the past 15 years | Hacker News Reader

A spreadsheet of the businesses I've started over the past 15 years

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231 pointsmyth_drannon102 comments

One thing that separates entrepreneurs from normal people is they aren't afraid of having stupid ideas. A good 90% of the ideas on this list, particularly the early ones, are laughable and are ideas you wouldn't catch a serious individual dead trying to come up with. Some people try from the start to be perfect and always fail because they don't understand you need dumb little ideas to be an entrepreneur.

So true! I’ll be the first to tell you the _vast_ majority of those ideas were objectively terrible but every single one of them taught me _something_.

It's also tough to accept the fact the market will buy things that one thinks is "stupid". Back in the 80s, NBC executives hated "The A-Team" despite the immense success it had on the NBC network. They felt the show was low-brow and cartoonish, "a hamburger show on a caviar network."

I really enjoyed seeing the list, Josh, and I appreciate the share via Twitter and here. My guess is that there are several serial entrepreneurs on Hacker News, and like myself, definitely can identify with your efforts.

Thanks so much!

hey - thanks for participating in the discussion here.

I've got a giant list of ideas (99.9% horrible) i've kept over the years. they always seem exciting when I'm writing them down ..but a week later they seem laughable. I always find myself thinking, despite realizing the idea is horrible - that I should have created a 2 or 3 page website as a business-like pre-mvp on the concept while I was still excited about it.

Yeah, I think a lot of it comes down to motivation. Most of these items were simply me having an idea or interest and wanting to learn more about it. Building something is sort of creative exploration for me. If it becomes something, cool. If it doesn't, also cool. I still learned stuff.

While that is true its certainly not the only way to do it.

It's often been a surprise to me which projects succeed, several times I've looked at a product and thought that is never going to work only to be proved wrong.

I don't understand this spray and pray approach to business - I'm not businessman so I may be talking out my ass - but I would have thought business is like a long term relationship. May as well have a spreadsheet of 50 failed marriages. If you aren't in it for the long haul what are you doing?

What he called "business" others (myself included) would call "side projects" until one of such projects would evolve into "business".

You have to start somewhere and try things out to find a business bringing revenue. And yes, it is "spray and pray" in essence. And I see nothing wrong with it. (probably because I tried to launch a similar number if not more of such "businesses"/projects and continue doing so)

He made 50 websites.

Some people see it as a lottery. But in the case you loose (99.9% of the times) at least you learned something in the process.

What can you learn from the lottery...

I think this person meant you can learn from the "lottery" that is startups unlike a regular lottery.

What about dates instead of marriages?

In your scenario would one date around before committing to a marriage or would one just commit to the first interesting person that came along and hope for the best?

Presumably if your relationship was extremely successful (if it were a business, it’d be making millions), then you’d be a fool to throw it away.

Think of it more like dating--it's normal to have 50 "failed" dates before you tie the knot. You don't commit until you find a great match. In business, this means the market actually cares about what you're making.

Predicting which software businesses will find this fit is extremely hard. VCs know this, and diversify their investments among many founders (knowing one big payday can make up for 10-100 failures).

Looks like this founder diversified by himself and launched small things faster. And eventually found something worth "marrying".

"Predicting which software businesses will find this fit is extremely hard."

Often a business is about the team, not the concept. Given any talented team, they an take any concept and evolve it to fit the market.

Also, there's no way he was able to take any of those concepts far enough given the numbers and time frame.

It can often take a small team several months to a couple of years to find out if it's going to really work or not.

I also wasn’t trying to do that. The large majority of these were me just trying things out to see what would happen. It’s how I learn. ¯\_(ツ)_/¯

Well your persistence is commendable.

Or a massive waste of time. Some days I'm not sure which. :P

There are very very few people who did it on their first run, it's like winning the lottery.

Bach wrote almost a piece every day. For most of his life. Most of it will never be played or heard.

The thing that's most common among the 'greats' is how prolific they were. They just kept doing. Just watching Jim Henson. Bio - he was doing Kermite for like 20 years before it remotely caught on. I worked at BlackBerry - the company started in 1982, about 20 years before the BB wars born. The other CEO started in 1992 about 10 years. So 30 man-years of combined CEO work before the BB came to be a product.

> Given any talented team, they an take any concept and evolve it to fit the market.

I’ve come to view great teams as “necessary but not sufficient”. That is: without a great team you will fail, but even with one you still need to build something a market will pay for.

If an objectively great team was all you needed, venture investors wouldn’t be satisfied with the dismal likelihood of getting returns on startup money (compared to other forms of investing).

Re: giving concepts time—fair point, but I think you also have to consider your own time as an investment. Sure a failing project could work with 2y more effort, but is it worth two years of your life to find out if it hasn’t already worked? What if you spent that time on giving another idea a chance?

No one really knows a general "right" thing to do. Even someone who's found a right thing can't be much help if they just say what they did right. The best you can do is avoid doing the wrong things while probing around for a right thing. It's a way of thinking called inversion.

Try 100 things while avoiding common pitfalls. One of them will probably pan out.

Human relationships and projects are not mutually exclusive.

The people you meet along the way ("marriages") often carry forward into future projects.

Business has a bit of luck and a bit of skill - as you learn more (for example, you learn that your Amazon affiliate made you $0.50 at its peak), you may choose to throw the dice again with a bit more force. Formalise it as a new business, or pivot, or don't tell people about your experiments.

This is what the long haul looks like.

See https://en.wikipedia.org/wiki/Modern_portfolio_theory

I'm jealous that he's made so many things, surprised by the small amount of money they've been sold for, and unsure whether this is someone I should emulate or someone I should view as a cautionary tale.

“Working hard will not guarantee that you will be successful, but I guarantee you, that all successful people worked hard.”

- Coach Kamogawa thru George Morikawa

Honestly, I'm not really sure if that's really true any more.

I wasn't working hard when I bought Bitcoin at three bucks a coin. I was just intellectually curious. If anything when I was working hard was two years before that on a soon to be failed startup. We crawled the web for ads just before the ad business went hyper targeted. I made -$20k from working hard.

I made a lot more from Bitcoin. I would have made way more if I'd put that $20k in Bitcoin and slacked off at some day job.

I guess I don't really follow my own advice though, as I'm presently working on a Sunday morning and I've only taken like two days off this month.

Edit:

Writing this comment briefly made me re-consider my whole life and I've come to the conclusion that being lucky and prescient observations are more likely if you've worked hard at some point. I did do an engineering degree with some economics electives at the best school in Canada, and understanding Satoshi's paper wouldn't have been possible without this background knowledge.

You are equating money with success.

Yeah. I realized that at the time I was writing it. But in software it's usually that way. Very few data points are Torvalds. Most are Gates or Zuck.

After writing the above, I Googled Linus. Apparently he's worth over $100m.

But you're right. Plenty of really successful poets or athletes are poor.

This is true even across generations. The reason white people (or anyone with a rich family) are able to live comfortably and not work today are due to the efforts of their ancestors at one point or another. "There's no such thing as a free lunch" is actually just true, and not a stupid idiom. At some point somewhere, work had to be done to get a reward.

How did you sell Bitcoin? For cash? Was it dangerous?

Well I mostly got out at $200 because I thought competent people regulated our economies and figured crypto would be banned by regulators, so it was pretty easy to spread it out over a couple wires. The remaining chunk I sold at the $10k-$20k window. I still think it could hit $50k/coin, but it was too large a percent of my assets and I figured I'd already made such a crazy return (1000x on average I think?) that squeezing out another 4x or 5x seemed reckless.

If only I hadn't been relatively broke when I bought in. I was suffering burn-out and basically working odd contracts here and there to keep the lights on.

If you're in the US, then Coinbase and Gemini are mature exchanges that you can directly transfer dollars to or from your bank account. I assume he probably used them or an exchange like them.

Great post, yeah sometimes doing nothing or something that seems unproductive pays off quite well actually! It's why I'm a little more lax when it comes to enjoying life nowadays. Ultimately, in my opinion a lot of luck is involved, so why bother? Enjoy the ride. Having said that, I still like to build things and hack just like you :)

Pyramid schemes are very profitable if you get in at the beginning.

The problem is that, by definition, most people are in a pyramid scheme at the bottom.

It's not totally clear to me that hard work involves quantity (the OP, seemingly) over quality (others who have started fewer, more successful businesses).

In general, there are lots of activities which give the appearance of hard work but are actually fairly superficial and detrimental to your long-term goals.

Not at all saying that's the case here, more just musing on the idea of grinding for the sake of grinding.

It's almost as if there's a stark difference between working hard and working smart. No one wants to acknowledge that.

I don't know if it's that necessarily. I think most people understand (in theory, anyway), the benefit of working smart.

I think there's an assumption that the most successful people both work smart AND hard, which is likely true to some degree - e.g. successful pro athletes have staff that likely conduct well-targeted and thoughtful practices, but the hours and effort involved are still quite intense.

I more-so think the problem is that "working smart" requires a lot of careful planning and forethought, and is quite ambiguous in most cases what it actually means - and in many cases just happens serendipitously. Because of that, the process isn't as obvious.

It's much easier (intellectually, at least) to emulate the "working hard" part and to a large degree it's the one we reward the most societally (even in more intellectual circles), so it's not surprising that it's the one that people assume is the most necessary component of being successful - and that the "working smart" part will either come naturally, or after success is had.

It depends on what level you're playing at. If you have access to capital and social connections then yes you need to play smart in order to succeed.

If you're some random person with no access to capital or social connections then your focus should be luck.

As a random person who started with no social connections and no capital, I think about luck all the time and it helps me to make decisions. Mostly, it helps me to weigh up future opportunities against current opportunities - I think about things that happened to me and I ask myself how unlikely they were to occur; if they were very unlikely, I try to stay on that unlikely path. Never waste your luck; you have to keep moving forward wherever it takes you. Sometimes it leads you to places you don't want to be, but beggars can't be choosers.

The keys to success are your social connections to capital and your acting skills; that's it, nothing else matters. Find a rich person, get them to like you (the difficult part), then get them to invest in your startup. Then you'll succeed. The richer your friends are, the more likely you are to succeed. However, it should be noted that the richer your friends are, the better your acting skills need to be (competition is tough).

I think that's a very simplistic view.

While there are of course people who have been extremely successful relying on those two things alone (and they dominate the headlines, of course), there are countless successful people who succeeded without either of those two things.

It's pretty disingenuous, for example, to argue that Katherine Johnson's (admittedly delayed in recognition) success is the result of social connections or acting skills.

An even more trivial example is that many pro athletes (in the US, at least) didn't achieve success because of their social connections to capital; most of them certainly aren't great actors either.

Also, hard work puts you in positions to get lucky, and it lets you leverage your opportunities more than others. There is no ladder to climb. You run around until you find the pay-dirt, and the people that run more find it quicker.

"Sold for" column does not at the same time means that he earned 0$ from such projects until he sold them.

Actual value is only what someone else is willing to pay.

Haha, I love this list. I wish I remembered all the stuff I did. In the early days (2003) I was doing flash games on newgrounds. Later turned to a hockey card store. Then I tried a million-dollar-pixel ads clone (made nothing, big surprise).

I also wasted too much time on stupid shit I never even launched. Like 1yr on a flash game of my dog (never launched). Another year on a site for musicians that never had a name or domain. A year on a bike rental directory. Another on a CMS for mobile sites (yeah m.domain sites, my timing sucked). A year or more on a trello-like project management app that sucked but launched with 100 beta users.

I also did 10-20 launch pages for testing marketable ideas. Most didnt work, and a few that did I didnt want to do (stuff like automated browser testing).

All that before hitting a product I've spent the last 4 years taking to six figures. So yeah, results vary. But I love this list. Brings back my good memories of wondering when I'd make more then 5 bucks on something that wasn't freelancing.

Oh I forgot. My "big break" product was actually from a mentor who needed the prduct. Had nothing to do with me hunting it down. Kind of funny actually. I can't really tell you what the secret to any success it accept seems that the more you work in the direction you want to go the closer you get. But some of it is just luck. Don't have any strong opinions for you.

> I can't really tell you what the secret to any success

You just did ;)

Right here:

> My "big break" product was actually from a mentor who needed the prduct. Had nothing to do with me hunting it down.

That's one of the great secrets to success right there, build something that you already know someone needs. Considerably reduces the role of the luck factor and guess-work.

True, you hit the nail on the head. All the new businesses I start (nowadays) comes down to: do we already have customers? Is there a real (proven) demand for this?

Bottom line, can we prove that this won't be a waste of time?

This is why I don't open the text editor and start new stuff that I come up with now days. I'm too traumatized from all the lessons I've learned to do that. Getting above water is the biggest hurtle. After that you realize that you don't need to touch anything that risks going nowhere.

> Amazon affiliate sites

I think this is a completely different mindset compared to engineers/"nerds", that's why most of us work for others instead of starting our own businesses.

Not clear why he couldn't sell any of those sites.

If we’re talking about the affiliate sites, it’s because they collectively grossed a total of maybe 50 cents.

Wasn’t worth the time to try to sell them.

There is nothing wrong with working for others if it fulfills you. I envy people who can have comfortable lives with happy families and a simple desk job that pays for what they need. Something in my brain is telling me I need more or I won't be happy, so I have many startups I'm working on and have exclusively begun working for myself. The grass is always greener on the other side, that much I can say. Enjoy your comfy engineering job and be careful what you wish for.

If you are a nerd who wants to break into entrepreneurship, prepare for a lot of fun, but also prepare to do work you think is stupid or never saw yourself doing, only for it to end up as a niche product. That's fine.

To each their own, obviously, but I look at this list and it's just... depressing. He seems like the kind of person who gets a lot of fulfillment from things like this, but for me I just see a whole lot of time wasted on bullshit.

That's the main reason why I work for others. You can't form a health system startup that includes dozens of hospitals and thousands of patients per day.

Yes, when I hear of those who "made it" and talk that 99% of what they are doing now are meetings, PowerPoint slides, pitching to VCs, public speaking, marketing, etc... I'm thinking - but are they happy? I can't imagine myself being happy while having to do all those things... :)

Those things sound boring, but when you are doing them for your own business - your own idea - it’s a lot of fun.

This! - I'm in a similar space myself. At once envious of those happy with a decent day job - corp or whatever (one of my good buddies is a "garbage man" and he seems pretty damn happy).

A year into struggling as an entrepreneur and no longer working at BigCo - I couldn't be happier despite having to live with a crazy amount of anxiety :)

And there is that middle-ground of being an independent consultant from where it is even harder to make a step, especially when taking in count your own hourly rate :)

These are mostly failed consumber businesses until Baremetrics, which had $100k in recurring revenue last month.

https://demo.baremetrics.com/

This is inspiring: the dominant culture today is "oh yeah, it's going great".

One quote that has stuck in my mind is from Chuck Jones, quoting his own prof at RISD: "You have 10,000 bad paintings in you. The sooner you get them out the sooner you'll get to the good ones."

I eventually learned to just let that dumb idea (weld, program, drawing) get out. Some good ideas fail, and most bad ideas fail, but sometimes you can only tell which it was (good or bad) after the fact.

And some bad ideas succeed. Flappy Bird and ship your enemies glitter come to mind.

Hey shpigford - curious how you made a living during this time? Was it via these apps/projects/businesses? Freelancing? Day job?

And kudos again. Great list.

From 2003-2013 I split my time with consulting. Did ~300 client projects over that time period.

They are more akin to projects than businesses. The majority of the businesses could be categorized as small web apps and Amazon affiliates. Most appear like he didn't find a problem to solve, but tried to create a solution. There also doesn't appear to be much thought given to market size for each product.

The title of the spreadsheet is “Josh Pigford's Absurd List of Products, Apps, Websites & Businesses”...they definitely weren’t all full on “businesses” and the large majority of them were terrible ideas. I definitely don’t recommend most people go the route I did. :)

Which route would you recommend instead?

No clue. Everybody's route is different. This is just how I've figured things out (and I'd still say there are many things I definitely have not figured out).

I should have paid better attention to the spreadsheet name :) What did you learn from this particular route?

I interviewed Josh for my book, The Parallel Entreprener (on Kindle etc), and can attest that he’s done all this experimentation for the love of the game.

For some of us the glory is not in the exit but rather in the building.

Feels like he doesn't give the businesses enough time to gain popularity. Some of them were clearly not bad ideas, like the ad management one.

I was going to say the same thing. Success takes perseverence.

It seems to me he is persevering, at starting new businesses.

That was my first thought. But maybe he prefers the ideation phase and getting it started (I know I do).

Regardless, this gives me hope because he has made money from several of them!

I noticed the same thing. The one that jumped out to me was something like, sold before it launched for $10000. Why would you build something and take 10 grand instead of launching it? Desperation?

I suppose it depends how much you need 10k, and how much you believe in the business.

I would gladly take $10k and move on to my next project over building, marketing, sales, etc., with no promise of a return. He obviously enjoys the inception/building phase and that time he got to build and then cash out with very little investment. If I was very confident that my idea would take off, I'd reject early offers and go for it. However, for many of us, everything after the building phase is like pulling teeth. For others, its great. But I definitely relate to that decision.

Part naivety on how markets/competition worked at the time and part “I have a $10k tax bill that I need to pay” (which is a whole other story in itself).

Completely agree! Me posting that spreadsheet was certainly not a recommendation for anyone to emulate me.

There are definitely businesses in there that I regret moving on from too soon but you live and learn. ¯\_(ツ)_/¯

Hey shpigford, I am curious about this terrible CPA that led to a $10k IRS bill. If you had to look for a new CPA can you tell me what you would look for and what would be warning signs?

Also, great list! Did some of those affiliate sites make money even though you eventually shut them down and didn't sell them?

Main thing is finding a CPA who has some experience with the type of business you're running. Freelancer, Corporation, etc...find a CPA who can speak the language.

It's less an issue now, but 10+ years ago, there were a lot of CPAs who didn't have much/any experience with internet-based businesses and so they weren't familiar with some of the additional bits to take in to account.

As for affiliate sites...I probably made a grand total of 50 cents from them...total. :P

Kudos on the transparency.

Where did you find your buyers?

i was about to ask that

According to his Twitter replies, he found them all on Flippa.

Flippa for all except TheAppleBlog.

Was there a lot of legal required (paperwork and lawyers) for Tutorial Outpost for $19k?

Not at all.

Really interesting, thanks for sharing this.

Why is it called Cedar & Sail when (as far as I can tell) it has nothing to do with either of those things? :p

In any case, congrats on hitting it big with Baremetrics!

I was wondering the same thing

I need to come up with an elaborate story on the name...alas I just picked two words that I thought sounded interesting together and BOOM, done. :P

Am I meant to be able to expand columns in this? It seems like I should be able to given that there's a lot half hidden content, yet I can't work out how to.

Change the url so you aren't looking at the html view: https://docs.google.com/spreadsheets/d/1ro4QYK1raqu3pNFMAjP9...

Then 'File', 'Make a copy' and you can edit and resize as desired.

Thanks!

Fixed! Sorry about that.

Can you share more info about how you sold some these businesses?

Listed them on Flippa! The end. :)

thanks for sharing. Cool idea. (PS we're a baremetrics customer - keep up the great work! :)

Thanks so much!

Why are the Amazon affiliate sites so unsuccessful? Are there too many of them? or what?

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