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Starting a Startup 101: The internet’s best on startup ideas, why you should start one, naming, and more

This is a curated collection of articles on starting a startup (everything from great ideas to naming your company to why you should do it and more). All links are free. It will be updated and expanded over time.

The founder question (eg, should I have a cofounder, what type of person, how do we work well together) is a big topic and one I’ll cover separately, probably a few months from now.

Here’s a list of the published 101s:

New ones will be in the right-hand navigation bar.

But above all notice how seriously they take Heroku. I don’t mean serious in the sense of grave, or humorless. I mean they did it like they meant it. You need to do that to make a startup work. And though investors are obtuse about a lot of things, they are pretty good at reading this. If you’re working with conviction on something you *know* is a step forward, everyone tends to fall in step with you (eventually). – Paul Graham

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Starting a Startup 101

Total links: 32 (updated regularly!)

Question 1: Why should I start a startup?
Question 2: Why should I NOT start a startup?
Question 3: What are good startup ideas? How do I know mine is good?
Question 4: What is it like to start a startup?
Question 5: How do I name my startup?
Question 6: Any advice for new entrepreneurs?

Question 1: Why should I start a startup?

How to Make Wealth by Paul Graham (Y Combinator founder)

A programmer can sit down in front of a computer and create wealth. A good piece of software is, in itself, a valuable thing. There is no manufacturing to confuse the issue. Those characters you type are a complete, finished product. If someone sat down and wrote a web browser that didn’t suck (a fine idea, by the way), the world would be that much richer.

The Vast and Endless Sea by Jeff Atwood (Stack Exchange founder)

I don’t care how much you pay me, you’ll never be able to recreate the incredibly satisfying feeling I get when demonstrating mastery within my community of peers. That’s what we do on Stack Overflow: have fun, while making the internet one infinitesimally tiny bit better every day.

Jump back to the ToC

Question 2: Why should I NOT start a startup?

Startups Are Hard by Chad Etzel (entrepreneur)

Startups that die rarely talk about it publicly because it is frustrating, embarrassing, and most of the time the people involved want to forget the whole mess and move on rather than sit around talking about the fact that they failed.

Why not to do a startup by Marc Andreessen (a16z founder)

First, and most importantly, realize that a startup puts you on an emotional rollercoaster unlike anything you have ever experienced. […] You will flip rapidly from a day in which you are euphorically convinced you are going to own the world, to a day in which doom seems only weeks away and you feel completely ruined, and back again.

Why to Not Not Start a Startup by Paul Graham (Y Combinator founder)

Not having a cofounder is a real problem. A startup is too much for one person to bear. And though we differ from other investors on a lot of questions, we all agree on this. All investors, without exception, are more likely to fund you with a cofounder than without.

Why You Should Reject that Start-Up Job
by NorthSider (Wall Street Oasis contributor)

Myth #1: “Don’t worry about the pay cut, you’re going to get equity in the business. More than anything else, my friends who joined start-up companies were thrilled about the concept of getting an equity stake (albeit a small one) in the business. All they had to do was work hard (at a place where their effort was far more likely to be noticed, due to the smaller workforce) and they would ultimately be paid off in the form of equity ownership in a growing business. Most people joining start-ups are under the impression that their initial equity package is just a teaser of what’s to come, but the truth is quite the opposite.

Jump back to the ToC

Question 3: What are good startup ideas? How do I know mine is good?

A litmus test for your idea by Nathan Kontny (Draft founder)

Folks like Tim Ferriss and Eric Ries have championed the idea of a “smoke test”: simply make a landing page selling a product that you pretend you’ve already made and then use things like Google Ads to drive traffic to those pages. If you measure enough interest (clicks, signups, etc.), make the product.

Frighteningly Ambitious Startup Ideas by Paul Graham (Y Combinator founder)

You’d expect big startup ideas to be attractive, but actually they tend to repel you. And that has a bunch of consequences. It means these ideas are invisible to most people who try to think of startup ideas, because their subconscious filters them out. Even the most ambitious people are probably best off approaching them obliquely.

Here’s the email summary from 1-Read-A-Day.

The idea maze by Chris Dixon (a16z partner)

1) History. If your idea has been tried before (and almost all good ideas have), you should figure out what the previous attempts did right and wrong. A lot of this knowledge exists only in the brains of practitioners, which is one of many reasons why “stealth mode” is a bad idea. The benefits of learning about the maze generally far outweigh the risks of having your idea stolen.

The next big thing will start out looking like a toy by Chris Dixon (a16z partner)

Disruptive technologies are dismissed as toys because when they are first launched they “undershoot” user needs. The first telephone could only carry voices a mile or two. The leading telco of the time, Western Union, passed on acquiring the phone because they didn’t see how it could possibly be useful to businesses and railroads – their primary customers.

The Startup Sector That’s Quietly Booming by Tom Tunguz

Math-based currencies are novel ways of enabling instant settlements, low cost transactions and foreign exchanges. The promise of these startups is to create new payment networks and more efficient ways of transferring value.

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Question 4: What is it like to start a startup?

All or something by David Heinemeier Hansson (37signals partner)

The marginal value of the last hour put into a business idea is usually much less than the first. The world is full of ideas that can be executed with 10 to 20 hours per week, let alone 40. The number of projects that are truly impossible unless you put in 80 or 120 hours per week are vanishingly small by comparison.

How big a factor is luck in startup success? by Yishan Wong and others on Quora

This may be a demoralizing and repugnant thing to hear for the Type-A “control my own destiny”-style of people who tend to populate Silicon Valley, but I think it’s true. Many a mediocre team has stumbled onto something lucky and many a talented team has gone nowhere despite great execution. Most languish somewhere in the middle.

Late Bloomers by Malcolm Gladwell (writer)

On the road to great achievement, the late bloomer will resemble a failure: while the late bloomer is revising and despairing and changing course and slashing canvases to ribbons after months or years, what he or she produces will look like the kind of thing produced by the artist who will never bloom at all. Prodigies are easy. They advertise their genius from the get-go. Late bloomers are hard. They require forbearance and blind faith.

Luck and the Entrepreneur,
Part 1: The four kinds of luck
by Marc Andreessen (a16z)

Whereas the lucky connections in Chance II might come to anyone with disposable energy as the happy by-product of any aimless, circular stirring of the pot, the links of Chance IV can be drawn together and fused only by one quixotic rider cantering in on his own homemade hobby horse to intercept the problem at an odd angle.

What does it feel like to be the CEO of a start-up? by Josh Abramson and others on Quora

I didn’t take a proper vacation for a few years, and when I finally did I made a point not to bring my laptop so I could unwind a bit… then I quickly realized that this was actually much more stressful for me than spending a normal day in the office. I originally believed that I wasn’t really on vacation unless my computer was at home, but over time I learned that I actually enjoy myself more when I’m able to keep busy with work in my downtime while traveling.

What Startups Are Really Like by Paul Graham (Y Combinator founder)

One thing that surprised me is how the relationship of startup founders goes from a friendship to a marriage. My relationship with my cofounder went from just being friends to seeing each other all the time, fretting over the finances and cleaning up shit. And the startup was our baby. I summed it up once like this: “It’s like we’re married, but we’re not fucking.”

Jump back to the ToC

Question 5: How do I name my startup?

How to Name Your Startup by Sam Shank (HotelTonight founder)

When initially naming HotelTonight, we considered other name combinations like ImpulseHotel and HotelNow before deciding on Hotel + Tonight. We chose tonight because it is evocative, exciting and reflects immediacy – and it gives you a use case. I was initially actually in favor of pluralizing tonight and calling the business HotelsTonight, but we couldn’t secure the domain name until a couple months after our launch.

How to name your startup: A 9 month first-hand journey through rebranding by PR Lambert (Learndot founder)

A name must be the MVP of your entire marketing and communications strategy. Your name is the top of your messaging pyramid. If people only remember 1 thing about you, it will be your name. A great name should do half your marketing for you.

Naming your startup by Chris Dixon (a16z partner)

3) I tend to disagree with The Name Inspector about name length. Shorter is definitely better. In particular the number of syllables is important. SiteAdvisor, while good at describing the product, is really clunky to pronounce. I also tend to really dislike Latin-y portmanteau names like “Integra” “Omnitrust” etc. Sounds like a pharmaceutical product.

Jump back to the ToC

Question 6: Any advice for new entrepreneurs?

7 Unlikely Recommendations for Startups & Entrepreneurs by Rand Fishkin (Moz founder)

Moz was built on the back of a blog. For the first 18 months of our “product,” we had very little except a few tools (many of which were available in free versions elsewhere on the web) and some guides I wrote. But, because we had a large audience – 10,000 marketers a day read the blog when we started our subscription in 2007 – we could iterate, grow, and learn with their help. By late 2008, we had a unique product that was pulling in subscribers far beyond just our community of blog readers. Without that “marketing first” approach, I’m skeptical if we ever could have gotten a product off the ground.

57 startup lessons by Slava Akhmechet (RethinkDB founder)

Your authority as CEO is earned. You start with a non-zero baseline. It grows if you have victories and dwindles if you don’t. Don’t try to use authority you didn’t earn.

90 Things I’ve Learned From Founding 4 Technology Companies by Jason Goldberg (Fab founder)

It’s not about you, part 1. Building a successful company is less about you and more about your ability to bring out the greatness in the people around you. When we pivoted from fabulis to Fab, we pivoted towards building a business around the unique tastemaker talents of one of our founders, Bradford Shellhammer.

Here’s the email summary from 1-Read-A-Day.

Applied Philosophy, a.k.a. “Hacking” by Paul Buchheit (Y Combinator partner)

Not everyone has the hacker mindset (society requires a variety of personalities), but wherever and whenever there were people, there was someone staring into the system, searching for the truth. Some of those people were content to simply find a truth, but others used their discoveries to hack the system, to transform the world.

Do Things that Don’t Scale by Paul Graham (Y Combinator founder)

There are two reasons founders resist going out and recruiting users individually. One is a combination of shyness and laziness. They’d rather sit at home writing code than go out and talk to a bunch of strangers and probably be rejected by most of them. But for a startup to succeed, at least one founder (usually the CEO) will have to spend a lot of time on sales and marketing.

Everything you need to know to succeed after (YC) Demo Day by Ash Rust (Send Hub founder)

Just as setting short-term goals are helpful for getting small units of work completed, setting longer term goals for the company is great for tracking overall progress and creating a team wide sense of urgency. At the start of each month, and quarter, we set goals for both our key metrics and also releases.

How technical does a start-up founder have to be? by Ryan Graves and HackerNews users

As the hacker co-founder in a shop of two people, let me tell you, you can play an equal role. Okay, so my partner doesn’t setup the servers or write the code or design the site; I do all of that. So what does he do? _Everything else_. Ask most any hacker and they’ll give you a laundry list of things they hate doing when it comes to starting/running a business or working on a project of any kind. In fact, it’s usually easier just to ask them what they _do_ want to do; the answer will almost always be “code.” In my case I add design and a couple other items to the list, but I digress.

Peter Thiel’s Startup Class Notes by Peter Thiel (Paypal founder) and Blake Masters (Judicata founder)

If there is one categorical rule, it’s that you should never ever have a down round. With few exceptions, down rounds are disastrous. If there are tough anti-dilution provisions, down rounds will wipe out founders and employees. They also make the company less appealing to other investors. The practical problem is that down rounds make everybody really mad.

Startup Advice by Sam Altman (Y Combinator partner)

24. You’ll often hear conflicting advice about everything but “build a great product”. This means you can go either way on much of the rest of it and it doesn’t really matter. Just make a decision and get back to work. Product/market fit is what matters. You can—and will—make a lot of mistakes.

Here’s the email summary from 1-Read-A-Day.

Stuck by Nathan Kontny (Draft founder)

After the Cityposh fail, I had little confidence I could pull off another business again. I was envious of my highly employable colleagues getting great jobs. […] Am I being an idiot? Am I missing an opportunity to strike while the iron’s hot and get a great job? I gave more than one serious look at the jobs out there.

The Ultimate Cheat Sheet For Starting And Running Your Business by James Altucher (writer)

52) Should I give stuff for free?
Maybe. But don’t expect free customers to turn into paying customers. Your free customers actually hate you and want everything from you for nothing, so you better have a different business model.

Here’s the email summary from 1-Read-A-Day.

Jump back to the ToC

That’s it. The next 101s will cover product (ideating, building and iterating) and stories (case studies, personal accounts, fundraising stories).

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