Best And Worst Decisions – Greg Linden

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 22, 2007:

Greg is the founder of Findory, a service that uses personalization technology to help readers discover information they would otherwise miss. Previously, Greg was at, where he wrote the recommendation engine and led the software team that developed Amazon’s personalization systems. Greg blogs at Geeking with Greg.

Solve a problem you want to see solved. If you do this, you will be excited about every day no matter what happens. I loved the problem Findory was trying to solve — helping people find the information they need by learning from what each person does — and enjoyed every moment I was working on Findory.

Be cheap, but not too cheap. In retrospect, I think I have been too cheap running Findory. Budgeting is an exercise that has death by burning out at one extreme and death by resource starvation at another. Findory lived a long time with a very low burn rate, but has been starved of resources, slowing growth, restricting hiring, and limiting paths for expansion.

Best And Worst Decisions – Marc Canter

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 22, 2007:

Marc Canter founded MacroMind, which became Macromedia, and was influential in helping to start the nascent ‘multimedia industry’ in the late 80’s and early 90’s. From there, Marc did scalable content, Interactive TV and what we now call ‘Ajax’ work – all during the dot com era. Since 2001 Marc has been blogging, developing the notion of “digital lifestyle aggregation” and helping to create open standards around open social networking and blogging. Marc is the CEO of Broadband Mechanics, and he blogs at Marc’s Voice.

Best decision I made:

I have to say that ever day I’m reassured as an entrepreneur that my gut level decisions are the right ones. When it comes to timing, projecting out ahead what’s gonna happen and where the money will be – I’ve been consistently about 10 years ahead of the curve. So the trick has been to slow myself down, and be ready when the rest of the world shows up. That’s what’s going on right now with open source social networking.

My worst mistake:

Was to rely upon the contributory efforts of others – and let that impede mycore milestones. This created a barrier of success – as you cannot rely upon free labor. You must pay people to do work for you. It’s the only way to get code done.

Best And Worst Decisions – Chris Pirillo

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:

Geek, Internet Entrepreneur, Hardware Addict, Software Junkie, Book Author, Once TV Show Host, Technology Enthusiast, Shameless Self-Promoter, Tech Conference Coordinator, Early Adopter, Idea Evangelist, Tech Support Blogger, Bootstrapper, Media Personality, Technology Consultant, Thicker Quicker Picker Upper. You can call Chris at 1.888.PIRILLO to leave questions for him to answer on his podcast. Chris blogs at Chris.Pirillo.Com

Bad Decision: Dealing with salespeople who didn’t have a clue what they were selling. A good salesperson (and there are apparently only two on the planet) will cost you a lot, but a bad salesperson will cost you even more. I loved them dearly, but love doesn’t pay the bills. Moral of the story: be cautious when it comes to yielding control of your business model.

Good Decision: Finding someone to help me facilitate various functions (keeping us on a publishing schedule, wrangling our content creators, etc.). Robert Glen Fogarty has been a godsend, and I wish I had found him years earlier. He’s talented beyond words, and has successfully alleviated my daily stress. Moral of the story: don’t be afraid to yield control to the right people.

Best And Worst Decisions – Ross Mayfield

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:

Ross Mayfield is the CEO and co-founder of Socialtext, the first wiki company and leading provider of Enterprise 2.0 solutions. A noted blogger and industry expert, he is a serial and social entrepreneur. Mayfield has grown Socialtext to over 2,000 customers with Software-as-a-Service, Appliance and Open Source solutions.

Best Decision — To become an entrepreneur in the first place.
I started my career in the non-profit sector, and then in the public sector, all in hopes of changing the world. I quickly realized that I could both have an impact and make a living in the private sector. And am lucky to now work on a company that produces social goods. Further, as a startup founder I believe you can quickly have a significant impact, possibly more than any other job. It is a roller coaster of risk. One day you can be beaming with pride to have created jobs and a fun place to work, and another you stress about meeting payroll and having folks be overtly human with one another.

Answer #2, to more specifically tie this to a decision…

Best Decision — Picking co-founders you trust.
It is not an exaggerated saying, that you marry your business partners, especially co-founders in a startup. Some look to partner with the Geek Girl for her technical whizbangery or Phone Guy for the sweet talk and access to capital. While you want to work with people that are skilled, I’d say the primary qualifier is if you can trust your co-founder. If you have any hesitation, either work it out or walk away, quickly. I’m luck to work with great co-founders I can trust with my life. Beyond trust, I would also put startup experience beyond specific skills. Someone that has rode the roller coaster before is less likely to barf in your lap.

Biggest Mistake — Not taking bigger risks earlier.
Maybe because in hindsight all risks are clear, but I always find myself regretting not taking bigger risks earlier. For example, open sourcing the Socialtext code was something we waited on until the company had strong footing. Partially because we thought there would be cannibalization, partially because we were understaffed to really engage with the community. But I believe if we bought this bullet earlier in the history of the company we would be reaping better rewards. As a planning exercise, now I always try to ask two questions: “How could we take more risk?” and “What risk can we take that creates the greatest amount of options?” I find there is always a way to do a little more, in particular by getting past instinct to control prevalent in so many entrepreneurs.

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.

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.