Best And Worst Decisions – Paul Graham

A few years ago, for Startupping, I asked several entrepreneurs about their best and worst decisions. With the shuttering of that site, their answers vanished from the web. I’ll be reposting them here. This was originally posted on February 20, 2007:

Paul Graham is an essayist, programmer, and programming language designer. He is currently a partner in Y Combinator, an innovative venture firm specializing in funding early stage startups. He is also a cofounder of Startup School, which this year is on March 24, 2007 at Stanford. Previously, he co-developed Viaweb, the first web-based application, which was later acquired by Yahoo, and more recently he pioneered the Bayesian spam filter, which inspired most current spam filters.
The best decision I made was to make Viaweb web-based. There were no web-based applications then, so we weren’t sure such a thing would even be possible. Initially what drove us was our dislike of Windows. Writing a desktop application would have meant learning Windows, which we really didn’t want to do. Whereas servers were the same Unix machines we used every day. To make a web-based application, all we had to do was figure out how to let users drive our software by clicking on links on web pages. That was a lot less work than learning Windows.

Hmm, no, actually the best decision I made was to get two fabulously good programmers, Robert Morris and Trevor Blackwell, to start the company with me.

The worst mistake I made, probably, was not being strong enough with investors. I now realize that investors like you to be assertive. It reassures them when founders take charge. But because our investors were so much older than us and had given us what seemed then unimaginably large sums of money, I felt I ought to defer to them. And yet I wasn’t prepared to do things their way in anything really important, like what the software should do or what our strategy should be. This inconsistency led to disputes that sucked up a lot of time and energy.

I realize that’s not really a decision. It was more something I didn’t do than something I did. But I think the worst mistakes startups make are mostly of that kind. Another big mistake I made was not to investigate IP agreements signed by people we hired. That nearly sank us later. But I didn’t decide not to; I just didn’t pay enough attention to it.


Best And Worst Decisions – Dick Costolo

A few years ago, for Startupping, I asked several entrepreneurs about their best and worst decisions. With the shuttering of that site, their answers vanished from the web. I’ll be reposting them here. This was originally posted on February 20, 2007:

Dick Costolo is currently COO at Twitter. He was formerly the CEO and cofounder of Feedburner, the leading provider of media distribution and audience engagement services for blogs and RSS feeds, which was acquired by Google. Previously, he cofounded and was CEO of Spyonit was sold to 724 Solutions in September 2000.
The best decisions I’ve made have all been hiring decisions. When you really are feeling the pain of not having a certain kind of person in the company, it’s easy to hire the first interviewee that walks through the door, but it’s critically important when a company is getting started to make sure you’ve found somebody that everyone on the team thinks is the right person for the role. People always tell you to hire A players, but the person also has to be a great cultural fit with the team you’re assembling and with the kind of company you want to be.

I’ve made loads of mistakes so I’ll try to think of one with a good lesson for startups – one of the biggest mistakes I made in a previous company was accepting a high dollar contract once for something that wasn’t core to the vision of the business we were running at the time. While the revenue initially feels great, there’s nothing worse than pursuing a piece of business that isn’t core to the startup’s vision. Lesson learned – once you decide what it is you are going to do, don’t pursue efforts that distract from the vision. One of the hardest lessons an entrepreneur has to learn is what revenue to turn down. You can certainly decide to change the vision and zig when the market zags, but in a startup, everybody has to be working toward a very focused vision, and chasing down side projects can be a real distraction (and probably ends up costing a lot more in terms of long-term resources than you’d expect).

Best And Worst Decisions – John Battelle

(A few years ago, for Startupping, I asked several entrepreneurs about their best and worst decisions. With the shuttering of that site, their answers vanished from the web. I’ll be reposting them here. Their biographies may not be up to date.)

John Battelle is an entrepreneur, journalist, professor, and author who has founded or co-founded businesses, magazines and websites. Formerly at the Graduate School of Journalism at the University of California, Berkeley, Battelle, is also a founder and Executive Producer of the Web 2.0 conference and “band manager” with Previously, Battelle was founder, Chairman, and CEO of Standard Media International (SMI), publisher of The Industry Standard and Prior to founding The Standard, Battelle was a co-founding editor of Wired magazine and Wired Ventures. John is currently the founder and Chairman of Federated Media and blogs at John Battelle’s Searchblog.

1. Either keep control, or don’t act like you have it. This was the primary lesson of The Industry Standard. I felt like this was the first large scale business I built on my own, and I acted like it. But majority control was always squarely in the hands of the company who funded it. We fought, and I lost.

2. Don’t skimp on hiring. Ever. I’ve hired folks who had the right resume, but I knew in my gut were not right for the culture of the business. I thought the skills/resume overshadowed the ability to work together as a team. They never do.

3. Do it for love, not money. This is pretty careworn, but it’s very very true. I’ve never ever started anything for money. Some folks are really good at starting companies to make money, but I’m terrible at it. I suspect most entrepreneurs are like me.

3a. But make sure what you are doing makes sense to others. Everything I’ve started or been part of starting, I’ve talked to key folks who would make or break the idea, and gotten their buy in and encouragement/help first. If folks who are critical to the idea are not interested, well….that’s a pretty good sign it isn’t going to fly. Doesn’t mean it’s not a good idea, but it probably means you’re not the person to do it.

4. Pick one constituency and stick to it. Very early on, we decided that FM would be “author driven”. We could have made the company “advertiser driven” but it struck me the core business had to do with the folks who produce the sites we work with. At Wired, it was all about the ideas. At the Standard, it was all about the journalism. One clear core driving force helps clarify decisions during the tough early years.

5. Don’t do something because you can. Do it because it’s good for the folks in #4.

Snap Groups

Now that I’ve gotten my blog back in order, I can (belatedly) announce the launch of my latest project, Snap Groups. It’s a return to communities for me, something I’ve been involved with since I wrote my first BBS system back in 1983 and continued up through the development of ONElist (now Yahoo Groups). Snap Groups is a new take on communities, combining elements of Facebook, Yahoo Groups, and real-time communication networks like Twitter. A great description of Snap Groups was written by Marshall Kirkpatrick on the RWW blog. I hope you will check out Snap Groups!

iPad Wallpaper

I’m really enjoying my new iPad. One of the first things I do when I get a new computer is change the wallpaper. This picture is one I took of Whangarei Falls, on the north island of New Zealand, last spring. I’m biased, but I think it makes an excellent iPad wallpaper (ping me if you’d like a copy of the original, full-resolution version).

My Startup2Startup Presentation

Here’s my Startup2Startup presentation from Feb 25, titled ‘Try This For Lean Startup’, detailing some of my experiences starting ONElist, Bloglines and now Snap Groups. You can find the video from the talk here.

10 Startup Marketing Commandments

Another article that originally appeared on the now-defunct Startupping blog:

  1. Don’t believe what you read. Don’t EVER believe what you read about yourself.
  2. “The Press” is no longer the most important source of coverage; the bloggers are today’s opinion makers, especially when it comes to coverage of technology innovations and, more importantly, the gossip that fuels the buzz of which products are hot, which are duds.
  3. Traditional PR firms only marginally “get” the blogosphere. Unless you have true Wall Street Journal worthy news, or are stupid, don’t bother paying $20,000 a month for an ineffective PR agency. You are far better off to hire a 21 year old who understands your stuff, give him/her a laptop and a six-pack of Crunk!!, and having them start chatting online about your firm/product.
  4. If an article claims your company is a loser, your product is a failure or that you eat goats for lunch, don’t kick the story forward by responding; better pour your energies into creating the best business model, the most elegant business solution, and go out and sell your company for a fortune. Unless you actually do eat goats for lunch.
  5. Describing a product as “revolutionary, but with an evolutionary bridge” only makes sense to a journalist who will never actually use your stuff; your customers will think you have been smoking crack. Go “leverage your synergies” and “shift your paradigms” somewhere else, marketingdroid.
  6. Never, ever, even if you have a term sheet from Google on the table, tell a journalist that your goal is “a billion dollars or bust” unless you want the next headline to read “Bust” when your sale/merger/IPO falls apart.
  7. Journalists are like teenagers, they have their collective crushes, then move on. Really. I’d give an example, but I’ve already forgotten about them all.
  8. The best quote in an article is from your customer telling the world why they love your product. The worst is you telling the world why they should love your company. That is unless the quote is from your mother telling the world how hard you work, that you are such a nice boy/girl and that her greatest wish is for a grandchild.
  9. If you are being interviewed by a journalist, read their recent articles. There is no better way to deflate an interviewer than to suggest they cover a topic they just wrote a story about the week before.
  10. You do keep track of what people are saying about your company, right? Subscribe to blog searches through Google or Bloglines and pay attention. Leave comments to blog posts where appropriate. It ain’t rocket surgery.

10 More Startup Commandments

  1. You will have at least one catastrophe every three months.
  2. Outsource effectively, or be effectively outsourced.
  3. Do you thrive on stress and ambiguity? You’d better.
  4. The best way to get outside funding is to be successful already. Stupid but true. But you, cheapskate, don’t need money, right?
  5. People will think your idea sucks. They’re even probably right. The only way to prove them wrong is to succeed.
  6. A startup will require your complete attention and devotion. Thought your first love in High School was clingy? You can’t take out a restraining order on your startup.
  7. Being an entrepreneur requires a healthy amount of ignorance. Note I did not say stupidity.
  8. Your software sucks. So what. Everyone else’s does also, and re-architecting is the kiss of death for a startup. Startups are no place for architecture astronauts.
  9. You do have a public API, right?
  10. Abject Terror. Overwhelming Joy. Monstrous Greed. Embrace and harness these emotions you must.

15 Startup Commandments

I’m going back and reposting some articles from the now-defunct Startupping blog. This was my first set of startup commandments:

  1. Your idea isn’t new. Pick an idea; at least 50 other people have thought of it. Get over your stunning brilliance and realize that execution matters more.
  2. Stealth startups suck. You’re not working on the Manhattan Project, Einstein. Get something out as quickly as possible and promote the hell out of it.
  3. If you don’t have scaling problems, you’re not growing fast enough.
  4. If you’re successful, people will try to take advantage of you. Hope that you’re in that position, and hope that you’re smart enough to not fall for it.
  5. People will tell you they know more than you do. If that’s really the case, you shouldn’t be doing your startup.
  6. Your competition will inflate their numbers. Take any startup traffic number and slash it in half. At least.
  7. Perfection is the enemy of good enough. Leonardo could paint the Mona Lisa only once. You, Bob Ross, can push a bug release every 5 minutes because you were at least smart enough to do a web app.
  8. The size of your startup is not a reflection of your manhood. More employees does not make you more of a man (or woman as the case may be).
  9. You don’t need business development people. If you’re successful, companies will come to you. The deals will still be distractions and not worth doing, but at least you’re not spending any effort trying to get them.
  10. You have to be wrong in the head to start a company. But we have all the fun.
  11. Starting a company will teach you what it’s like to be a manic depressive. They, at least, can take medication.
  12. Your startup isn’t succeeding? You have two options: go home with your tail between your legs or do something about it. What’s it going to be?
  13. If you don’t pay attention to your competition, they will turn out to be geniuses and will crush you. If you do pay attention to them, they will turn out to be idiots and you will have wasted your time. Which would you prefer?
  14. Startups are not a democracy. Want a democracy? Go run for class president, Bueller.
  15. You’re doing a web app, right? This isn’t the 1980s. Your crummy, half-assed web app will still be more successful than your competitor’s most polished software application.

WordPress Blog Switch

After many years of hosting my own blog, I’ve moved Winged Pig to a blog hosted by WordPress. Apologies for any RSS or link craziness.