Prospective Friends and Business Associates


FOLLOW UP – Bill Justice, but I want to hire him

I am in a fortunate position — There are about five times as many people who want to meet, interact and partner with me than I have time for. I try to allocate/ration my scarce time, energy and attention in a thoughtful and intelligent way. I seek to interact with exceptionally talented and interesting people who are energetic and — most important — who are not a pain in the ass. If you’re a possible friend, business associate or even a potential date, you may want to read the following essays :

To the extent that I have found interactions with certain people to be less than satisfactory, it is almost always because of one or more of the issues raised in these essays.

The following list of categories is oriented toward prospective business associates, and many of them are written for someone who might be a full business partner, as opposed to a less intense business relationship. Many of these categories, however, are also appropriate for prospective friends (and even prospective dates). Just by reading the categories, you can get a sense of my expectations and values.

In business, I am looking for :

  • people who have outstanding technical skills, whether as a writer, manager, Web design, WordPress, SEO, social media, VB.Net programming, or whatever their skill set is
  • people who are easy to reach and easy to interact people, people with low cost of interaction
  • people with a high level of intellectual curiosity
  • people who are self-managing, who have follow through
  • people who are financially ambitious

More than anything, I expect prospective business partners to demonstrate follow through (see Section 21). I want you to take the initiative, to be proactive, to follow-up on whatever we have agreed to. If I have to constantly do the follow-up, it quickly becomes tiring and you will soon move to my “B” or “C” list (which is like the difference between going to Heaven and going to you know where.).

This page was last edited on August 2, 2009 and is obviously a work in process.

1. Decisive

I like people who can make up their minds reasonably quickly and subsequently they do not change it.

2. Direct

I like people who are direct, who tell you what they are thinking. I never took mind reading in school so why not just tell me what you are thinking? Most Japanese do not say “No”; instead, they say “Maybe”. How wonderful, just what the world needs, an entire nation of people who cannot be direct.

3. Knows What They Want

I like people who know what they want — in business, social life, love.

4. Has a Plan

I like people that have a plan — “I am at A, I want to be at B, to get to B this is what I need to do.”

5. Narrow Minded Dweebs

There are some people who are simply narrow minded dweebs (“NMDs”). (Give me a good definition. I know it when I see it.) I have learned that an initial display of NMD-ness is almost always the tip of the iceberg and that such people are more trouble than they are worth.

6. Open and Approachable

A female friend recently made several friend requests through Facebook. One girl, Elizabeth W. Nicholas, responded by threatening to call the police. Another, Laura O’Connell, threatened to report her to Facebook. A third, Robin McGuire, wrote back, thanked her for the request, told her a bit about what she was doing professionally, and said she would love to meet sometime. Who would you rather associate with: Nichols/O’Connell or McGuire?

7. Competent / Good at What They Do

I want to work with people who are competent, who are good at what they do.

8. Detail Oriented

In most cases, it is important that people I work with be detail oriented. Sometimes there are superstars who think and operate at such a high level that they don’t need to worry about details, and if I find a superstar, I can get quite flexible quite fast, but let’s face it, most people are not superstars. (Jack Welsh hasn’t called me recently; he must have lost my phone number.)

9. Do It Now / Bias Towards Action

I like people who do it now; who have a bias toward action. JFDI (Just F******* Do it.).

10. Can Do Attitude

I love working with people with a can do, get-it-done-now attitude, what Paul Graham calls being relentless resourceful.

11. Bust Ass

I don’t know any way to make a lot of money without busting my ass. If you know of such a way, please tell me, I will give you half of what I make. In the meantime, I am going to bust ass and you should also.

12. Computer Skills

I like working with people with really good computer skills. Even if you are working on a project that is not computer-related, you can easily get a two times increase in productivity if everyone on the team is gifted in computers. The IBM PC was introduced in 1981. By 1991 it should have been obvious to any adult with a three-digit IQ that it was going to change the world. If you’re 28 years old, presumably you started using a computer no later than age 18, so you’ve had a decade to get good at them. If after ten years you still are not good with a computer, the odds you will ever be are extremely low, about equal to winning the lottery. I find that people who are really good at computers are usually clear thinkers. Computers force a degree of precision in your thinking that is excellent training for clear logical thinking.

When computer gurus (I prefer “guru” or wizard to “nerd” or “geek”) such as myself get together, what do we talk about? Incompetent computer users and how much “fun” it is to deal with them. Life is too short — at least my life is too short — to do a lot of handholding for people that should have learned this stuff 5 or 10 years ago. If I had to choose between going to the dentist every day for the rest of my life and answering computer questions from novice computer users, well, that’s a tough choice.

Let’s assume you don’t know how to tie your shoes. Would you, for year after year, keep calling friends of yours, asking them to come over and tie your shoes? Hell no! Would your friends do this? Hell no! They would tell you to learn how to tie your own shoes. A few might come over and teach you. But none of them are going to keep coming over, day after day, week after week, year after year, to tie your shoes for you.

Why are computers any different? Sure, they are more complicated than tying your shoes, but that is all the more reason to start learning them now.

13. Technical Skills

I like people with good technical skills. If you are a Web designer, you should be really good at Photoshop, Illustrator and WordPress. Otherwise, why should I bother talking with you? If you are an SEO, you should know be a guru at Google Analytics.

14. Appropriate Technical Skills

Not only do I want people with good technical skills, but I also want to work with people with appropriate technical skills. For example, almost all of the 500+ Web sites I will be launching in the next five years will be based on WordPress. I meet a lot of graphic designers, some of whom are visually talented, but many of them do not know WordPress, let alone know it well. They all say they can learn it but realistically it would take a smart designer a few years to get good at it. I simply don’t have the time to wait. Sure, if they come back after they have learned it, I would love to talk with them. But in the meantime, we don’t have much to talk about.

15. Intellectually Curious

It’s hard to imagine someone being great at what they do without being intellectually curious. I have worked with David Steadman, the former CEO of GCA. David is interested in almost everything, at least as it relates to business. This is a key reason for his extraordinary success.

16. Focus

Those who can focus on the task at hand are people I want to work with. I am reminded of a brilliant mathematician I know who works for a hedge fund. His colleagues tell me that in meetings, he will stare out the window to look at some unusual cloud formation. He will then write on the blackboard a mathematical formula describing this formation. Apparently he does this regularly. He simply cannot focus on what the meeting is about, namely developing new trading strategies.

17. Big Company Itis


The companies I am involved with are successful and we expect a high level of growth in revenues and profits the next five years. Nevertheless, as compared with, say, GE or Microsoft, our revenues and profits will always be a rounding error of a rounding error as compared to theirs. If we ever achieve in one year what Microsoft earns in interest on its cash in one day, I would be happy

In a small company, people wear many different hats, they do different things. You simply have to be more talented and resourceful and you need a broader range of skills. I remember a lunch I had with a girl who worked for a large publishing firm. She had one specialized skill; she literally could not do anything else. At her job, every other aspect of the process was performed by someone else, each of whom had very specialized skills. It was a veritable Frederick Taylor assembly line. In 20 years of professional experience, she had never bothered to learn any other part of the process, not even basic HTML. She was not a good fit for our company.

18. Excellent Communication Skills

I rarely have communication problems with Americans. Those in other countries are a different matter, particularly Indians. It’s important you have good oral and written communication skills. If I have to spend a lot of energy trying to understand what you are saying, it’s not going to work.

19. Self-Directed and Self Motivated

I like people who are self-directed and who can motivate themselves. I do not have the energy, the desire or the inclination to motivate you.

20. Self-Managing

The less I have to manage you, the happier I am. You are an adult; you should be able to manage yourself. If I wanted a career as a baby sitter, I would advertise my services on Craigslist.

21. Follow Through

I like people who follow through and who do what they say they will, particularly if they are self-managing and if I do not have to bug them to do so. Let’s assume someone is proactive and always demonstrates follow-through; their cost of interaction to me is X. If they are not proactive and do not demonstrate follow-through, their cost of interaction increases by at least an order of magnitude; let’s call it 10X. At X, I want to work with them. At 10X, I frankly don’t, life is too short, and there are so many other people I can interact with that have a lower TCI. It’s inconceivable that at 10X that what they bring to the table justifies the hassle of dealing with them. Simply by being proactive and demonstrating follow-through all of the time, you can decrease your cost of interaction by one order of magnitude.

If you’re not good at follow-through, the solution is simple: Read, implement and master David Allen. After you’ve been following David’s system for a year, give me a call. In the meantime, however, let’s not have a business relationship, as I will simply get frustrated with you and you’ll burn bridges with me forever. It’s better if you first get your act together and then we can have a productive business relationship.

I cannot say this too many times: Follow through is extremely important. I do not have time to keep calling and e-mailing you; you need to initiate contact. Otherwise, it simply is not going to work.

22. Manages Their Commitments

Responsible adults should manage their commitments — do not commit to do too much, and accomplish what you commit to. At the risk of repeating myself, if you are not good at managing your commitment, learn David Allen (see no. 23).

23. David Allen

If we are going to be business partners, I would love for you to learn David Allen’s Getting Things Done system. It will change your life.

24. Being Organized

I like people who are organized.

25. Tickler / Follow-up Systems

You should have some kind of tickler / follow-up system so that I do not have to keep bugging you to follow through on your commitments.

26. Low Cost of Interaction

I want to work with people that have low total cost of interaction.

27. Reliable Systems

You should have reliable systems — telephone, voice mail, e-mail, computer, data backup. I want to deal with people that have enough money to afford good systems and who are intelligent enough to know (or hire an expert) which systems to pick.

28. Easy to Reach on the Telephone

I like people that are easy to reach on the telephone. There are a substantial number of people who never answer their phone; they only return calls. Imagine two such people trying to reach other. A would call B, who would not answer. B returns the call but A does not answer. A then calls back but again B does not answer their phone. This could literally go on for millions of years, or at least until one of them died, and they would never connect.

29. Returns Telephone Calls Quickly

OK, I realize you cannot always answer your phone. When I leave a message, I like people who return telephone calls not promptly, but quickly.

30. Frequent Communication

If we’re going to work together, we need to talk regularly on the telephone. If you’re hard to reach, if you never answer the phone, if you do not return telephone calls promptly, or if you only want to talk once a week, it’s probably not going to work.

31. You Initiate Contact

When I am working with someone, I much prefer that on a regular basis, they initiate contact with me. I am very easy to reach and I spend much too much time calling people and leaving voice mails.

32. Chooses the Most Appropriate Form of Communication

Business associates of mine should choose the most appropriate form of communication. If you want to schedule an in-person meeting with me, call me; do not e-mail me. If you just want to pass along a message (a one-way flow of information), then send me an e-mail rather than calling me. Think about each message and how it should best be communicated to me; I will do the same.

33. In-Person Meetings

Most of the people I work with do not live in New England. If someone is local, that can be a significant advantage, as in-person meetings are often more productive. If I suggest we meet in person, please do not argue with me, but rather just set up a meeting. When I propose meeting with you, that means I am willing to invest a fair amount of time in you, as I do not set up 5 or 10 minute meetings.

34. Meet in Back Bay

If we’re going to meet in person, I will probably ask you to meet me in Back Bay, where I live. Realistically I am not going to drive to Salem, unless I really, really want to meet you.

35. Working Onsite vs. Remotely

Right now, all of my companies are virtual. Sometime towards the end of 2009, I expect to set up an office and many of the key people will move and all of us will work out of the same office. I expect we will double our productivity by doing so.

36. Foreign Countries

Most of the people I work with reside in the United States; a few, in Canada. With one exception, I am open to working with people in other countries. The exception is India; we simply have had too many bad experiences with Indians.

37. Time Zones

I live in Boston, which is in the East Coast time zone. If you’re in a radically different time zone, we need to figure out how practical it will be for us to reach each at reasonable times. I work all of the time so in many cases, this will not be a problem.

38. Too Busy / Overscheduled / No Free Time

There is a saying, “If you want something done, give it to a busy person.” This is true to a point. Many busy people are simply too busy, overextended and overscheduled to take on working with me. They have no slack. When something unexpected happens, there is no spare time to absorb the shock, and so everything gets screwed up. I don’t want to work with such people. Why should my life get screwed up because you have taken on too many commitments?

39. Have Control of Their Own Schedule

I like people that have control over their own schedule.

40. Number of Hours Available Per Week

Although I prefer to work with people who can work full-time, I regularly talk with people who initially can only work part-time, which is fine in some cases. Most of the time, I want someone who can work at least 20 hours a week. If all you can provide is 5 hours a week, realistically how much are we going to accomplish. There are some exceptions — tasks where the scope is extremely well defined and people with very specialized skills (e.g., in three hours, you can move my SQL Server database from one server to another).

41. Difficult to Schedule Appointments With

If we need to make an appointment, please do not make it a painful process. “I don’t have my calendar. I have to get back to you.” Please tell me, why on earth do you not have your calendar on your phone?

42. TMI When Scheduling Other Appointments

With some people, when you schedule an appointment with, they tell you the details of the 37 other appointments they have scheduled that day. This is TMI (too much information). I don’t need to know any of this. Just tell me the times you are available and spare me the commentary.

43. Repeatedly Reschedules Appointments

Once we make an appointment, I expect you to keep it unless you really have a really good reason to reschedule. One social organizer who wanted to meet me literally changed our first meeting five times in a row, after which I gave up. To this day, he has not figured out why I don’t want to meet with him anymore.

44. Be On Time

If we are going to meet in person, please do not be late. I will not be.

45. Mobile Telephones

If we are going to meet in person, I expect you to have a mobile phone, so we can reach each other in case there is a problem. Please have your phone with you and please charge it the previous night, etc.

46. Follows Our Manuals and Our Procedures

I am very good at designing procedures to make the process go more smoothly, literally one of the best in the world. If I told you at what age I redesigned the case flow for my father’s law firm, you might find it scary. So it makes sense for me to write the manuals, and in most cases, it makes sense for you to follow them.

47. Uses Our Information Systems

For many of the projects I work on, I design a custom information system to help us manage the project and the process. I have a simple approach. All data is stored in Microsoft SQL Server, Enterprise edition. MSQL has numerous algorithms to ensure that the database does not get corrupted. In terms of designing and writing the forms, queries and reports, if these will be used internally exclusively, I use Microsoft Access. No other tool is as good for “quick and dirty” systems as Access is. If the forms will be used externally, then I direct a VB.Net developer who develops a Web form. If I am going to go to so much trouble to design a world class information system, you should at least use it.

48. Project Management

For all of my companies and business projects, I use a Web-based project management system called Goplan. It’s simple to use, you can easily track everything that needs to be done, and since it is Web-based, no setup is required. We create a new project, break everything into tasks, set due dates, and on a daily basis, we can reevaluate what we are doing.

49. High Level of Professionalism

I like to work with people who demonstrate a high level of professionalism.

50. Checking and Testing Your Work

You should check your work. If you are a Web developer, you should do your own preliminary testing. (We do, of course, also have testers.) If you are a writer, you should proofread your writing. If you are a Web designer, you should view your Web pages in all of the major browsers, in the current and at least one previous version, before you submit it to me. When someone gives me something and there are blatantly obvious errors, that is a bad use of my time.


51. Commitment to Excellence

I like to work with people who demonstrate a commitment to excellence, who pride themselves on doing great work.

52. Entrepreneurial Mindset

With some exceptions (e.g., my assistant, my housekeeper, my chauffeur), I prefer to work with professionals on an entrepreneurial basis. I have an entrepreneurial mindset and I find I relate better to people who think the same way. If someone is a partner of yours on a project, they are more likely to be thinking about your co-venture in the shower, and thus while they are taking a shower, you are making more money. Typically I structure arrangements so that if a person fails to perform (in a major way — I am not talking about missing a deadline or something), there is a huge penalty on that person. Since I always follow through on my commitments, I need not worry, and if they fail to follow through, then they suffer. I find that by screening out those who are not entrepreneurial, I end up working with a higher caliber of person.

53. Attitude Toward Risk

If you want to make a lot of money, you are going to have to take some risk. That’s the way the world works.

54. Realistically Financially Ambitious

People who want to make a lot of money are often interesting to me, provided they combine it with a strong work ethic, exceptional smarts, good business judgment, and outstanding technical skills. At the same time, they should be realistic. If I am providing all of the capital, if I have invested far more time than you have, if I have far more business experience than you do, if I simply bring more to the table, then it is not realistic to assume we are going to be equal business partners.

55. Sufficient Financial Resources

I want to work with people with have financial resources for whatever they are undertaking. This does not mean they have to have the money themselves; it’s quite OK with me if they have raised it. But ideally they should have already raised it, or alternatively have a realistic plan for raising it, rather than just a vague idea.

In some cases I am willing to pay more than my fair share of a project’s expenses, or even all of them. But I want this to be negotiated and decided up-front, not half way through a project and then you tell me, “I have run out of money.

56. Family Situation

In some cases, one’s family situation creates huge obstacles to high performance work — your kids are drug addicts, your spouse does not buy into the concept, your grandmother is always meddling. It’s important to ask about a prospective partner’s family situation.

57. Evenings and Weekends

If someone does not want to work evenings and weekends, that is a bad sign, at least for the more ambitious projects. This is not always required, of course, but it is worth asking.

58. Thinks at the Right Scale


I like people who can be very detailed oriented when it is required and at the same time, can see the big picture.

If I have to choose, I am very skeptical of people who can only see the big picture. In most cases, they want to spend a few minutes thinking grandiose thoughts while I spend thousands of hours actually doing the work. Thanks but no thanks, particularly since I can do both. Those who can see the big picture and then roll up their sleeves and execute, that gets interesting.

Obviously there are some exceptions to this. If Jack Welch wanted to work with me and he made it clear that I was going to do almost all of the work, he would provide advice and contacts only, I would probably be interested. (I don’t know Jack hasn’t called me recently, he must have lost my phone number.)

59. Thinks at the Right Scale

I like people who can view matters from different scales. Sometimes you need to be at the runway level, sometimes at the 10,000 feet mark, sometimes at the 50,000 mark. Talented people are able to move between these levels, depending on the circumstances.

60. Realistically Ambitious

I like people who are ambitious, even very ambitious. At the same time, it’s important to be realistic. It’s great you want to start a software company, and I hope you do well. No, you will not be as successful as Microsoft, that is simply not going to happen.

61. Smart and Gets Things Done

Joel Spolsky of Joel on Software argues that in hiring people, one should hire smart people who get things done. Those are the kind of people I want to work with. I have some very smart friends who simply cannot get things done, and I don’t want to do business with them.

62. Gets Things Done / Makes Things Happen

Some people know how to get things done, how to make things happen, while others couldn’t execute a simple plan if their life depended on it. I want to work with the former.

63. Relentlessly Resourceful

Paul Graham wants to work with entrepreneurs who are relentlessly resourceful. I do too.

64. Smokers

If we’re going to work together in person and you are a smoker, I do not want to work with you. People take smoking breaks and they come back reeking of smoke. If we’re not going to be meeting in person, then obviously it does not matter if you smoke, although I may wonder why you engage in such self-destructive behavior.

65. Being an Adult

I expect you to be an adult. If I want kids, I will have them. If I am going to raise kids, I want to raise my own kids, I do not want to raise you. If I want to become a nursery school teacher, I will enroll in a graduate school of education and obtain my teaching certificate. If I want to be a babysitter, I will advertise the availability of my services on Craigslist and be paid $10 an hour.

66. Normal People

In general, I want to deal with “normal” people. There is being different because you refuse to accept conventional wisdom when it is clearly wrong. And there is being odd simply for the sake of being odd. It’s important to know the difference. Dying your hair purple does not mean you are creative. Wearing a nose ring does not mean you are original. Shaving your hair into a Mohawk does not mean you are a genius. Covering your body with tattoos does not mean you are a free thinker. All that any of these things mean is that you are an idiot.

67. Continuous Self-Improvement

I want to deal with people who engage in continuous self-improvement.

68. Quick Start-up

When you start working with someone, first impressions make a huge difference. I like it when I can see some tangible, immediate results. I have learned the hard way when I meet someone and they cannot start for, say, six weeks, in many cases it just never happens. I like people who can jump in right away.

69. Strategic Vision

People with strategic vision are rare and when I find them, I am very interested. Someone who can think strategically, who understands how everything fits together, and who can map out a business strategy, is often worth their weight in gold. One SEO expert I work with, for example, told me, “I think you need to be more systematic about which topics you focus on. Let’s develop a matrix, listing on the Y axis every possible legal topic and on the X axis, these 16 characteristics, and then rank each topic on all 16 characteristics.” It took me and another person 3 weeks to do this, but at the end, we had a detailed road map of what to do for the next year.

70. Broad Range of Skills

I like people with a broad range of skills.

71. Complete Package

People who have such a broad range of skills that they can do it all are always of special interest (and are remarkably rare). I have more than enough money; my scarcest resource is my time and energy. I wish I had to manage people less. If some is self-managing, I am really interested. For example, one of my primary activities is starting legal Web sites. I am talking with a guy who can strategize with me on which topics to cover, he can design the site, he knows WordPress well, and he has excellent SEO/traffic building skills. Although he is not going to write the sites, he will find and manage the writers. It should be obvious why such a person is of such strong interest to me.

Most people I meet and most people I partner with are not the complete package. That’s OK. If they have a specific skill that is useful to get the job done, we can do business together. But complete packages are always particularly interesting.

72. Consistent Behavior

I like people whose behavior is consistent over a long period of time. If you tell me in March A, and then in April your opinion changes, and then a month later it changes again, I might wonder about you. As Disraeli said, “The secret to success is constancy of purpose.”

73. Kind, Gentle and Empathetic

I want to work with people who are kind, gentle and empathetic. Yes, I realize this essay makes me sounds like the biggest hardass you have ever met, but actually deep down I am quite a softie.

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