random thoughts on being an entrepreneur

Random thoughts on being an entrepreneur.

I wouldn’t say I was an authority on entrepreneurship, certainly not in the same league as people like Fred Wilson or Jason Calacanis. That being said, the last couple of years haven’t been too shabby, either. With that in mind, here are a few thoughts I have on the subject, in no particular order. The list, by the way, is far from complete- I’ll probably be adding to it sooner than later etc.

1. Everything takes three times longer than it should. Especially the money part.
2. The best way to get approval is not to need it.
3. People want what they can’t have. In fact, that’s pretty much all they do want.
4. Once you become an entrepreneur, you find the company of non-entrepreneurs a lot harder to be around. You’ve seen things they haven’t; the wavelengths alter, it’s that simple.
5. In a world of over-supply and commodification, you are no longer paid to supply. You’re being paid to deliver something else. What that is exactly, is not always obvious.
6. Word of mouth is the best advertising medium of all. The best word of mouth comes from disrupting markets.
7. People buy your product because it helps fill in the narrative gaps in their lives.
8. You can either be cheapest or the best. I know which one I prefer.
9. Some people think that once they secure venture funding, their problems will be over. Wrong. That’s when your problems REALLY begin.
10. It’s better to be underfunded than overfunded.
11. If an average guy in a bar can understand what you do for a living, chances are you’re halfway to becoming a commodity.
12. It’s easier to turn an ally into a customer than vice versa.
13. If you’re happy in your career before the age of thirty, you’re probably doing something wrong. Heck, if you’re happy in your career before the age of seventy, you’re probably doing something wrong.
14. Smart, young, artistic people are always asking me which is a better career path, “Creativity” or “Money”. I always answer that it doesn’t matter. What matters is “Effective” and/or “Ineffective”.
15. Write the following on a piece of paper, have it framed, and stick it on your office wall: “Have you hugged your customer today?”
16. People will always, always be in the market for a story that resonates with them. Your product will either have this quality or it won’t. If your product fails this test, quit your job and go find something else. Just making the product incrementally cheaper or better won’t help you.
17. Products are idea amplifiers. The molecules and/or bytes are secondary.
18. People remember the quality long after they’ve forgotten the price. Unless you try to rip them off.
19. Markets serve entrepreneurs better if the latter can keep the former undersupplied. Oversupply is the kiss of death.
20. I personally know a former CEO who, once he attained control of the company, ran an EXTREMELY profitable business into the ground in less than two years. From a market cap of $100 million to ZERO, just like that. Why? Short answer: He loved being “The” CEO, but he didn’t much care for being “a” CEO.
21. In terms of becoming an entrepreneur, probably the most useful thing I learned in the last twenty years was how to enjoy my own company for long stretches of time.
22. One successful entrepreneur I know well has a wonderful quality, namely that he never, ever compares himself to other people. He just does his own thing, which actually serves him rather well. Just because his competitor has bought himself a bigger motor boat, doesn’t mean he feels the need have a bigger motor boat. This quality helps him to build his business the way he sees fit, not the way the motor boat people see fit.
23. Running a startup is full of extreme ups and downs. Which is why so many successful and happy entrepreneurs I know lead such normal, stable, unglamorous, “boring”, family-centered lives. Somehow they need the latter in order to balance out the former. Extra-curricular drama looks great in the tabloids, but that’s all it’s ultimately good for.
24. MBAs are conditioned to use their brains in much the same way as sex workers are conditioned to use their genitals. Nice work if you can get it.
25. Bill Gates may have a million times more money than me, but he isn’t going to live a million times longer than me, watch a million times more sunsets than me, make love to a million times more women than me, drink a million times more fine wines than me, listen to a million times more Beethoven String Quartets than me, nor sire a million times more children than me. Human beings don’t scale.
26. F. Scott Fitzgerald once wrote, “There are no second acts in American lives.” F. Scott was a drunkard and a fool.


  1. #13 worries me – I’ve been very happy and grateful to achieve what I have at a young age, but in the last couple months I’ve realized that I feel “too comfortable for comfort”. I like what I do and I’m good at what I do, but I’m bored without something to constantly fight for. I wonder if 2007 may be the year I just say “fuck it” and take a large risk that could jeopardize any kind of career stability I have.
    #21 is very true – I’ve unfortunately come to terms with it.

  2. Maybe another one to consider with regards to money is that entrepreneurship is no panacea for financial woes – if you can’t handle your own money well, what makes you expect to be able to handle a company’s/VC’s/investors money well?

  3. I vividly recall sitting on a balcony in the south of France with Jude and saying: “I can’t go back to the job I’m doing.” She said something that should be blindly obvious to anyone: “Well don’t then.” I didn’t.
    At the time I was a tenured partner in a British firm of Chartered Accountants. The money was rolling in. The Merc looked utterly gorgeous.
    Two weeks later, I was unemployed. I sacked myself. The best decision I ever made. I’ve never looked back.
    The second best decision was walking out on the trophy wife, the house piled with antiques, the bank account and everything that wen with it.
    So you’re right. F.Scott Fitzgerald was clueless.

  4. Fantastic Article!!!
    I have been an entrepreneur since I left high school, I found that university was dreadfully dull and basically trained peoples brains to ‘get hired’
    I always asked myself, who is doing the hiring?
    Its true that there are tons of ups and downs, and money and projects seem to take FOREVER to complete, but its so worth it in the end never to have to be a ‘mental slave’ to another institution (aka higher education) or another business owner again.
    I am writing this on my 5 minute break from working on a project at 3am in the morning… thats what it takes sometimes to never have to be a slave.

  5. I have not posted any comment in a while. I have been a little bit overwhelmed by more text than usual over the last few weeks with the various manifestos.
    Great stuff Hugh
    (From France)

  6. Hugh, whatever has caused you to have this incredible transformation into a hunky, giving, lover of life–I have to say–I love it!!

  7. I’m confused by #13. I agree with the first part as I’m 31 and not being happy with my career has kept me hungry and motivated. However, if I’m feeling the same way in 40 years, I can’t help but think I’ll be regretful of the career path I had chosen. I’d like to think at some point I’ll be very happy with my career and that that alone will keep me motivated. Perhaps I’m being naive and time will change my view point.

  8. I love Jeff Bezo’s idea of a “Regret Minimization Framework” he came up with when deciding whether or not to quit his highly paid day job on wall street to start amazon.com.
    If you think about it, most people are all about minimizing risks – entrepreneurs are about minimizing regrets.

  9. Hallelujah for #4. My non-entrepreneur guests are ready to kill themselves from sheer boredom and fatigue from electical engineering-based analogies. Cool, I can start enjoying dinner parties again.

  10. >> People want what they can’t have. In fact, that’s pretty much all they do want.
    so true. it’s like being addicted to drugs…
    not that i’d know.

  11. Hugh,
    With all due respect, there’s very little in here that’s not exceedingly obvious and therefore there’s no real value in it. It reads more like a marketeer’s approach to filling space about entrepreneurialism.
    This is a bit like Barack Obama writing his list of thoughts about becoming a national political figure. Be around for a while and prove you’re not a flash in the pan, create some real success, create something of lasting value, be known beyond a handful of people who live on the Web, or more clearly put – earn your stripes and then write your list.
    Random thought number 1 should have been “stick to what you know and do it really well”. Random thought number 2 should have been one of your cartoon cards to make point number one. That should have ended your list.
    I have been and will remain a fan of yours. How To Be Creative was brilliant! But this was not.

  12. Chris, I think I can answer that. Years ago, being a misfit adolescent in a small Army town, smarter than those he should be learning from, drove me to being a performer. I went, on scholarship, to a great but geographically disadvantaged theatre program, and on the eve of my first show three months into freshman year our conductor handed me a slip of paper with something inspirational on it. I didn’t think much of the note at the time, but I managed to hang on to it.
    Spring turned to summer, and then to fall, metaphorically speaking. As I went on all my romantic notions about stage life vanished, and at the end I saw it as (I’m borrowing here) a long plastic hallway full of pimps and thieves where good folk die like dogs in the street. I’m now going back to school, after lengthy absence and a few good projects, for media studies, more for a handle on the tech side of things more than anything. I already know what to do with it :-)
    However, the paper turned out to be valuable. It was, apparently, a letter writen by Martha Graham. I’ll quote from it at some length, as I’m sure Martha wouldn’t have cared.
    There is a vitality, a life force, a quickening that is translated through you into action and because there is only one of you in all time, this expression is unique.
    And if you block it, it will never exist through any other medium and will be lost. The world will not have it. It is not your business to determine how good it is nor how valuable it is nor how it compares with other expressions. It is your business to keep it yours clearly and directly, to keep the channel open.
    You do not even have to believe in yourself or your work. You have to keep open and aware directly to the urges that motivate you.
    Keep the channel open. No artist is pleased. There is no satisfaction whatever at any time. There is only a queer, divine dissatisfaction, a blessed unrest that keeps us marching and makes us more alive.

  13. no. human beings don’t scale.
    trust doesn’t scale.
    thus neither does your own brand of jugaad, or magic or mojo or whatever it is you call that spark in you. You know, the one that wants to dance like a flame on the top of a candle?
    well, brands scale, and hugh taught me this. vive la global microbrand.

  14. Hugh,
    I’m a lighthearted guy! That’s why I like your blog. I read you for what you’re good at, not advice on how which DVD player to buy or to learn about the latest Web 2.0 company. That’s why I was surprised and disappointed with this post.
    It just seems a little self-indulgent and uninformative for a guy who’s “last couple of years haven’t been too shabby” to already be publishing his “list” on being an entrepreneur.
    Let Guy be Guy and you be Hugh.
    Still a fan,

  15. Fret not, Rick, I don’t think being a “blogging enterepreneur” is really my bag 😉
    That being said, I’ve had quite the adventure these last two years.

  16. Hugh, just to expand your thoughts. Compare & contrast what Seth Godin’s post about “On becoming The” with your #20
    A good LIST.

  17. Being an entrepreneur is not for everyone, for without sun sets and sex workers the former would be a wasted effort. #1 is soo right and #4 makes christmas with the family difficult.

  18. “Random thought number 1 should have been “stick to what you know and do it really well”.”
    Yep. Sounds like the makings of a bestseller to me. Oh, and while I’m at it, I might even remove my kid from Harvard Business School…. 😉

  19. its damn lucky your number 22 guy is complete edge case otherwise all your businesses other than stormhoek would fail. want to sell more yachts? more suits? that would be bloody hard if your customers didn’t suffer from status anxiety…
    or maybe your target customers are old money rather than entrepreneurs…

  20. #11 is interesting in that the advice from most business bigwigs is that you need to be able to explain your business in 8 words or less (or whatever). I’ve always that was a nice goal but not really set in stone.

  21. Bravo to walter higgins and his comment above. Considering risk vs regret is a fantastic framework for examining the “entrepreneurial condition”.

  22. w/r/t #4: Unless your customer base is comprised of fellow entrepreneurs, you absolutely must find a way to maintain a vital connection with non-entrepreneurs, because otherwise you’re going to have a more difficult time understanding their needs and how to satisfy them.
    If you’re able to manage #23, then dealing with #4 should be possible; but if not, then you need to be aware of this weakness in yourself and make sure that key people on your team can fill that gap in your skillset.

  23. This is a fantastic gathering of people who really know what it’s like to be an entrepeneur. Just gets me excited about things! #11 is a crucial step. One, because I like bars, and two, because one of the hardest things to master is a simple, succinct explanation of what the heck I am doing. How does that get to be so difficult?

  24. So great and so true, especially number 21…but have to say I don’t agree with 13, I think if you aren’t happy in your career then you should be doing something else.

  25. Just realised after reading all that. I am a natural entrpreneur always have been, but never new it, thought it was what everyone wanted to do, can feel that comfortable feeling coming on again, time to step out of the comfort zone and smell the coffee

  26. Great Blog! Here are my 3 rules-to-live by:
    1. Assume everyone you meet is intelligent
    2. Have a passion for what you do
    3. Get over yourself

  27. For all the complaining about working for others or being a slave, you would think that all small business owners would treat their employees well…unfortunately this is not the case….its boils down to: Am I a slave or a slave owner?
    Keeping people around you who dream the same dreams makes for a wonderful workplace. Especially if you allow employees to share in the rewards of success, and feel that you acknowledge their contribution to that success.
    A fatal flaw of many entrepreneurs is that they think they are doing everything by themselves, and everybody else is a hinderance to their success.

  28. Nor can Mehtap! I want to say that your site better throughout the World Wide Web :)
    Thank you. Keep it.

  29. Hugh,I am also an entrepreneur. I’d like to add to your thoughts. The best qualities of an entrepreneur is summarised in a Kipling’s poem “if”. It has helped me tremendously to deal with the up and down in entrepreneurial life. I think the solution for #4 is that: accept it, some people are never going to be an entrepreneur, you should appreciate the fact that it makes your life a bit less competitive. :-)
    If you can keep your head
    when all about you men are losing theirs
    and blaming it on you,
    If you can trust yourself when all men doubt you
    but make allowances for their doubting, too.
    If you can wait but not be tired of waiting,
    or being lied about, don’t deal in lies,
    Or being hated, don’t give way to hating,
    and yet don’t look too good nor talk too wise,
    If you can dream but not make dreams your master,
    If you can think and not make thoughts your aim,
    If you can meet with triumph and disaster,
    and treat those two imposters just the same,
    If you can bear to hear the truth you’ve spoken
    twisted by knaves to make a trap for fools,
    Or watch the things you gave your life to broken,
    and stoop and build them up with worn-out tools,
    If you can make one heap of all your winnings
    and risk it on one turn of pitch and toss,
    and lose and start again at your beginnings
    and never breathe a word about your loss,
    If you can force your heart and nerve and sinew
    to serve your turn long after they are gone,
    and to hold on when there is nothing in you
    but the will that says to them “hold on,”
    If you can talk with crowds and keep your virtue,
    or walk with kings nor lose the common touch,
    If neither foes nor loving friends can hurt you,
    if all men count with you but none too much,
    If you can fill the unforgiving minute
    with 60 seconds worth of distance run,
    Yours is the Earth and everything that’s in it,
    and which is more, you’ll be a man, my son.

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