The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary

Posted on May 15, 2013 | 91 comments

The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary


The one word the best entrepreneurs never accept.

I said it.

Now let me walk you through a broader story because avoidance of the word in and of itself will seem cliche. Stay with me.

dr. noWhen I was little I had a role model for entrepreneurship – my mom. She was a natural leader. She was president of the UJA in Sacramento. From this I saw civic involvement and leadership first hand.

She was a nurse but was never graduated from a 4-year college. Still – she can do the NY Times crossword puzzle better and faster than I. Even today.

She was a hustler. And a ball buster. And a natural sales person. She was never afraid of the word “no” even to the point of embarrassing me.

My youth was filled with her arguing with vendors if they tried to pull a fast one. As my wife will tell you – arguing is cultural – you grow up with it or you don’t. I did. It’s very Jewish. For better or worse. She’s learned to embrace it in me. If a maitre d’ tries to seat me at a table in huge traffic flow or a corner she knows not to bother sitting down.

My mom bought our family’s first computer and encouraged me to learn it at 13.

She opened 2 businesses – a bakery and then a restaurant. I worked in both before leaving to work in a software company at 17. I never knew a world in which you weren’t supposed to work and make money. Even though my dad was a doctor and in retrospect I probably didn’t need to earn my own money. My mom always taught me it was my responsibility to do so.

When I was younger my mom taught me something I never forgot

“You don’t ask, you don’t get.”

It’s simple. I know. But it amazes me how many people don’t really get it.

2 stories.


When I lived and worked in London my wonderful assistant was Deborah Halliday, who was raised a very “proper” British young lady. Her brother played rugby for the English rugby team and went to Oxford. That’s kind of like having a brother in the NFL in the US.

If there was any society in which being a hustler was out of step with the norm is was England. Yet I was a foreigner so I got away with being different.

I used to ask Deborah to book my travel plans in France and Germany were I went 1-2 times / month. There were online tools to book this stuff but the Internet booking sites were early.

I would tell Deborah, “I found this hotel near the Champs Elysees for 170 Euros. But I don’t want to pay that much. Tell them I’ll stay if they’ll give it to me for 120 Euros.

“What? You want … what?”

“Mark. You can’t do that! You can’t just name your own price.”

Me. “Of course I can. Tell them you found a hotel down the street for 100 Euros but I prefer to stay at their hotel. Haggle. See what you can do.

Deborah. She was mortified. Bless her cotton socks. I put her outside of her comfort zone.

Me. “Deborah. You don’t ask, you don’t get! What’s the worst they can tell you? “No?” If so, we’ll call back an hour later and pay 170 Euros. It’s not like they’re going to tell you ‘no’ in an hour. You might as well try!”

Classic Mexican Road strategy.

Here’s the thing. They NEVER said ‘no.’ Such were the times. They weren’t fully occupied.

She began to love it. It was liberating. I taught her to make it a game. I would challenge her to see how cheap she could get rooms. I can still hear her giggle at how ridiculous it was in her mind’s eye. And yet how eye opening it was that you could have almost anything you wanted. If you just asked.

Story two.

Fast forward. My son Jacob. He’s now 10. When he was 7-8 my wife used to sit down with him to do homework and train him the importance of getting it done early and well. Luckily I have such a terrific and organized wife. Or Jacob would be screwed.

They sometimes did homework at Le Pain Quotidien. And if Jacob was good he could get a treat.

Tania once took him up to the counter to pick out a treat. He pointed at a chocolate cake and told Tania he wanted a piece.

“No, honey. That’s a whole cake. You can’t have a piece. It’s not cut. Why don’t you find something else?”

Jacob, “Of course I can have a piece. Just ask them!”

Jacob has IJ. He knows to ask for what he wants. He is respectful. But he has an inner compass that in stead of saying “ok” to adversity he says “why not?”

She had him ask the lady behind the counter directly. She said, “no problem.”

My wife smiled and couldn’t wait to tell me the story.

My wife thinks Jacob’s an over negotiator but she secretly loves it. I always take it as a compliment.

Both stories have something in common. Not being ashamed to ASK. As I tell people almost weekly, “What’s the worst that could happen? That they would say, ‘no’?”

And I mean it. I promise you that 95% of the people I meet are afraid of people telling them no. They are personally embarrassed by it. Or insulted. Or view it as failure.

I’m told “no” all the time because I often ask for more than others do and therefore you need to be willing to hear “no.”

I was on a flight last year from DC to LAX. I had a business class seat due to status of flying a lot and my family was in economy. I felt bad and was planning on rotating.

But when I sat down I asked if my family could upgrade since there were 3 open seats. I assumed the answer would be “no” but I figured I had nothing to lose.

The flight attendant said “ok. but you’ll have to pay a small upgrade fee and I can’t move them until after take-off.” But move them she did. And she decided it wasn’t really important to make me pay since the seats were unoccupied.


We had also just been upgraded from London to Baltimore.

2 times in a row – unreal. My wife was a bit incredulous (but grateful). I simply pointed out that our kids learned a more important lesson than the downside consequence of their expecting to always sit in business class (which isn’t going to happen!).

They learned to ask, “why not?”

You don’t ask. You don’t get.

And here’s the thing about “no.”

I know first hand just how chicken people are about hearing it. I’ve sat through so many meetings where sales reps didn’t ask for the order. I’ve been pitched by hundreds of entrepreneurs who never actually asked me whether I would invest. Very few people do.

Here’s an experiment for you.

Hold interviews with tech people, marking people, ops people, finance people – whatever. They always finish the interview with a “thank you” and barely ask next steps.

Any great sales person will ask you at the end of the meeting, “So, how’d I do? Who else have you spoken with? How do I stack up? What do I need to convince you of to get an offer? What is the next step in the process?”

Great sales people are trained to “ask for the order.” If you interview a sales person and they don’t ask for the order, be worried.

I like to flip things on their heads. I like to ask in reverse in interviews, “If we did get aligned to offer you this role, do you plan on accepting? What other offers do you have? What do we need to do to win? What steps do you still need before you decide to go with us?”

I want to know. And I have nothing to fear in the answer.

My favorite (not!) is dealing with lawyers (or VCs) who say, “as a firm, we never do a, b, c.” Let me tell you now that often this line is BS. But my standard response is, “I don’t care what you normally do. I think it’s right for our situation. So unless you explain to me logically why it doesn’t make sense at our company, my assumption is that it’s a good idea.”

In summary, I recommend some honesty with yourself. “Asking” is a skill that can be practiced and learned but you need to be self aware.

How comfortable do you feel with asking for the order? How confortable do you feel with asking awkward questions or asking for things that are out of the norm, “Could we have your room for 120 Euros so we don’t have to stay down the road?”

If you don’t find it within your confort zone – practice in small ways for asking for slightly unreasonable things just to get used to it. It’s a skill you’re going to need as an entrepreneur.

After all – you don’t ask, you don’t get.

  • Keith West

    I like this. I never have the card either…

  • Keith West

    Followup– I got the introduction!

  • Daniel Aguiar

    Could u take a look at my slide deck?

  • Jason Kaplan

    Track “No’s” – As a sales leader you sometimes track calls, meeting, touches , etc, for your sales people. Many years ago we used to track “No’s” for calls and emails and reward for No’s. Especially when cold calling/emailing you have to get some “No’s” to get a yes so why not recognize that effort (of course we dug deeper to make sure they were getting the right number of “yes’s” too).

  • Carl Jackson

    Great post – My mother also instilled the same thing in me when i was very young too starting with ‘you don’t ask you don’t get’.

    As I got older she evolved it to “You can get anything in this world, you just need to ask the right person the right way at the right time”

    She included knowing who is the right person and timing (building rapport) so the person you ask is already invested in the social relationship and it’s even harder to say no. I’ve also successfully used it in business and for everything personal much to my wife’s initial horror. Now she uses it too – much to her delight.

    Works great in interviews – “is there anything that gives you any reason you can’t offer me the job right now?”
    I used it in final interviews to get accepted into an accelerator program “is there anything that concerns you in the team or our business that would preclude you from offering us a spot right now?”
    There’s almost zero downside as you’re instantly seen as a closer, if there is concerns you get to address those in the room right then which then allows you to ask the question again.
    ‘keep going till they buy or die’ – but that’s another quote :)

  • Kelly Watson

    Great post! I totally agree – and women are especially bad at asking for stuff. I love how you describe “asking” as a skill to practice. I think this makes it easier for people to give it a try and feel ok about getting it wrong once in a while. Developing a skill through practice takes away the perfection expectation. Love it! I’m going to link to this from our website.

  • Erika

    There is a word for it, (iie in romanji) for Japan. What you’re talking about, though, is that when someone asks you to do something, rather than just say “no” (or iie), you say “chotto” which equates to a hesitation and “well… I’d love to but I really have this other thing I have to do… etc.”

  • BenGranola

    If he is going to Chattanooga then he can stop off in Memphis. See Mark, nice little trip to the Mid-South.

  • anne weiler

    This is a great talk on how to ask and how asking connects you. I’ve been practicing and it works. Getting free accommodation for my whole team for a tradeshow is one of the baby steps in my journey!

  • Rhonda Marable

    Excellent post. I used to think that I feared hearing “no” but what I used to fear was hearing the explanations when I asked “why not?” I’m working on fixing this fault but it really bothers me when I get crap answers from people. Whether they be illogical, ill-advised or just plain stupid, it’s hard for me to shake it when someone’s answer to my “why not?” is something I can’t understand because, frankly, I’m not mean/rude enough to get it. My girlfriend and close friends tell me to laugh it off and throw it into the “doesn’t matter” pile…but it’s hard. I think this all stems from me growing up in a “because I said so” home. Never did get any real reasons for hearing “no” when I asked for reasonable or unreasonable things….guess that’s why I stopped asking for things in the early part of my career. OH well…over that now.

  • Chris McCoy

    Asking for help. Asking for the order. Hard. Necessary life skills. Thank you for sharing this Mark. Timely and good knock upside the head for me.

  • Elia Freedman

    I have to admit, I miss her a lot. She was a great salesperson, great ethic, and a lot of fun.

  • Elia Freedman

    You were way more polite than I!

  • Philip Sugar

    They do. It is a breath in with your teeth clenched and the air sucking through them.

  • Ricardo Sanchez

    Asking for something, negotiating and arguing is something I’ve been doing since I was a kid, watching my family do it, all the time. For example, as a kid my mom will take me to the market and it was perfectly natural and expected to negotiate the price of the items we were buying such as eggs, milk, fruit, etc…

    Today, as a naturalized citizen (I am originally from Mexico and came illegally to the US), I am in a good place, with a great job in software engineering and a startup in the works. I also help other entrepreneurs get together to start projects and startups, and everything I have accomplished so far has been in good part for my inability to stay quiet when others do, I always ask!

    Another example, as a meetup organizer I have always asked other companies to sponsor the drinks, food, space, etc… I have been running the meetup for over two years and I have yet to find a venue, or company to say no to my request :)

    Lastly… when I was about 12 yrs old I called a pizza place a couple of times and told them that the pizza we’ve just picked up was not the right one, then I asked if we could have another one made “correctly” and to please send it our way, it worked both times, I got free pizza! but then my mom found out and explained that while it was great I had the guts to do this, it was a lie and it was just wrong and never did it again. She was right about it and I learned a lesson.

    Most people dislike saying No as much as they dislike hearing it.


  • Robert

    An excellent and valuable article. Thank you. I’ll be sharing.

    Consider one alternative to the “95%…are afraid of people telling them ‘no’.” I do find the “no” uncomfortable, but it’s not fear. My discomfort comes from making other people uncomfortable.

    Putting someone “out” is my struggle – cutting people off in traffic, taking too long to order (or to leave afterward), golfing too slowly, or asking someone to leave their comfort zone. Each of these causes physical discomfort. It can be handicapping, and it doesn’t change the value of your article in any way.

    I just wanted to broaden the scope of the challenge.


  • Peter Tippett

    Loved this, it is what our business is at it’s core. Getting the Video/TV world to engage with their audience in real-time by “asking” is so hard as they have been taught to tell a story, a one way conversation. The ones who do learnt to ask using our tools, get engagements of 15%+ with their viewers creating new compelling content. We are converting more everyday to what we do.

  • Peter Tippett

    Loved the video as it linked with what we have been doing for the last 5 years of adding an “ask layer” to Video which we have expanded to TV. The work we have had to do to get over the “fear of asking” we learnt by doing videos of ourselves and sending them out using our feedback tool. We have pivoted this to Live TV and got commentators onboard. Once they overcome their fear and start asking, they have become addicted to it as it is so refreshing and they feel so connected, just like what Mark says, once you start and have a few wins, you keep doing it.

  • Dan Berger

    At Social Tables one of our 5 cultural pillars is “Yes if instead of No because” and we embody it in everything we do, from speaking to each other to dealing with customers.

  • Susan

    Super…. Would you feel comfortable fixing the typo…. the word is the last “comfortable” in the story. Then you’ve got “confort” zone instead of comfort zone. Is this a test?

  • Bob Schwartz

    Thanks Mark, i sent this to my two boys (19,21), nice overview… they are pretty darn good at asking, and asking for the ‘order’ 3+ times…i just tell them not to use this on me and their mom 😉

  • Marcy Capron

    I suppose the “waspy” version of that (or perhaps the “my dad grew up on a farm, the youngest of 7 in a family with no money, and determined his own fate” version) is :

    “it’s only no until it’s yes.”

    And that is what I was raised on. My dad is a tech entrepreneur and I followed in his footsteps, but if I hadn’t spent 7th grade thru college negotiating for everything I wanted I never would’ve gotten the custom experiences out of highschool and my [hand-created, multidisciplinary] university degree that have gotten me to where I am today. I was able to have a fascinating career while still in highschool and essentially finishing atypically early, and it stunned the highschool administrators that I had the balls to ask for what was best for me. Precocious? Sure. But I have no regrets. That highschool career (fine-art photographer: doing gallery shows, selling prints and running a studio out of my parents’ house) actually taught me entrepreneurship hands-on and informed my current career in technology.

    I don’t have any IJ in me and I do sometimes struggle with the ability to haggle when it comes to purchasing things, but when it comes with getting what I want on a conceptual/achievement/education level, I push without even thinking about it. My dad has been known to pit car dealerships against each other to get the best deal, so I know I have the cultural tendency in me I think I just fight against wanting to come off rude. I’m still learning!

  • Vincent van Leeuwen

    Truly great read. Thanks!

  • Gaston Irigoyen

    Great stories Mark! And since it’s important to ask, did you forget to answer the comment on your post about online video networks? :)

  • Greg Mand

    Cannot tell you how many times I have put this into practice over the years though I would modify one of your statements just a bit. Assuming it’s not a direct ask (via in-person or phone) the worst is not that they say ‘No.” The worst is they simply ignore you and you don’t get yes or no. :) My wife has similar reactions as well to my asking for better tables, etc. but she’s learning my ways as well.

  • Serge Kozak

    Cant wait to read them.

  • Laurence Trifon

    Mark, have you read “Getting More” by Stuart Diamond? It’s like a manual for “don’t ask, don’t get.” Best negotiation/life skills book I’ve read.

  • Daniel Tawfik

    I just saved 250 bucks at a Kinkos in Mountain View because of this blog. That’s 250 bucks to acquire users. Big thanks from Vonjour!

  • Edison Acuna


  • JamesHRH

    This is good advice, although there are two thoughts that come to mind:

    1) A lot of people care what people think of them. They don’t ask for discounts because they don’t want to be see as cheap or poor. Fear of No is not the only driver of not asking.

    2) I assume that you don’t find the phrase ‘I Jewed him down 15%” offensive.

  • rbutr

    Great post. I am usually an asker, but not nearly as advanced as you! My mum has always been a master at asking for things too, but I need to step up my game a bit and stop being so ‘reasonable’ with things some times, and ask for more unreasonable options, just in case.

  • Georgina

    This is by far the best article I’ve read in a long time. It doesn’t
    just apply to tech start ups, it applies to life in general and getting
    that piece of cake!

    I spent an hour on the phone with my brother who just took over the family hotel. I was trying to convince him to take a risk, make a decision, do something! He needs to know that if you don’t ask, you don’t get.

    Thanks for the pep talk. I forwarded it to my brother.


  • Péter Kádas

    Great article. I’m doing this kind of sport at car rental services. Usually a 2-3 class upgrade is achieved. However:

    ” I’ve been pitched by hundreds of entrepreneurs who never actually asked me whether I would invest.”

    of course they don’t: Ask for money and you get advice. Ask for advice and you get money. And this old wisdom seems to be working. Isn’t it conflicting with your suggestion to directly ask for an investment? …But let’s try it: I kindly ASK for your answer. :)

  • Scott Britton

    Awesomeness and thanks for writing this. You need to flex that discomfort muscle to have the balls to get good at this. When friends ask where to start I always recommend asking at fast food places for more of a certain type of condiment/ingredient.

    i.e. Chipotle – hey can I get a little more chicken?

    Flex the courage muscle enough and before you know it, its just something you do

  • Meganlisa

    Hi Mark. I’m a total believer in the don’t ask, don’t get rule. I trained in Merrill Lynch’s stock broker training years ago and that was what they counted as the top reason someone didn’t get an order…they didn’t ask. But I’ll caveat it…they also taught us that we only had so much time and people only so much patience…so use the rule wisely, when you have something the other person could want or deliver, when you’re ready and when you have time to follow through. Better to lose something than to put your reputation on the line and not deliver. No is temporary. Anything can be fixed, altered, improved, change, etc. If someone does say no….best to ask why not (and Merrill taught to ask three times and get three no’s before going on to why not, what might be better for you, and when can I ask again/call back)!

  • wfjackson3

    “My youth was filled with her arguing with vendors if they tried to pull a fast one. As my wife will tell you – arguing is cultural – you grow up with it or you don’t. I did. It’s very Jewish.”

    I suppose that’s true. Arguing seems very much like a learned behavior rather than an innate one. And more for the weird parallels between us: my mom, while not jewish, is where I got all of my arguing experience from. Retailers, restauranteurs, movie theaters, insurance companies, landlords, buying cars, everyone. She was always negotiating. It was great training.

  • AJ Kohn

    I love this post but I think it’s less about the word ‘No’, which I find to be very powerful to keep focused and on task, and more about the phrase you must have:

    ‘It never hurts to ask.’

    I believe in that mantra 138% and live it every day. That pretty girl in high school doesn’t get asked out as much you might think because the guys are afraid to ask. That’s amazing and sad.

    Gretzy has it right (as always). You miss 100% of the shots you don’t take. So take your shot. Ask for what you want. The worst that happens is they say no (or you never get a response from that email you sent or voicemail you left).

    But more often than not you get a response and you get some (if not all) of what you ask for. It never hurts to ask.

  • Michael Fainshtein

    Good and practical!

  • SocialNetworkSoftware

    Great story and advice. Ty for this!

  • Chaitanya Konher

    Thank you for such a simple yet potent advice. I have always subscribed to the idea of ‘why not?’, but had restricted it, more or less, to my work. I confess to being a little timid in the past and this often reflected in my professional life. I inherit this trait from my father, but chose not to bother myself with it until I joined his business last year. Our initial dealings with clients as a team were tragic, to say the least. A few things have changed for good since then, and I like to think that I have gotten a little better at asking what I want and have even managed to convince my father that there is no harm in doing so! Of course, my conservative upbringing does manifest into self-doubt at times and that is why I am glad I found your post. I realise there is a long way ahead and no stopping now. “You don’t ask, you don’t get.” I needed this so very much…

  • Wabi Sabi Ecofashionconcept

    Verry true. Great post