The Hustler

You spend enough time with enough startups and you genuinely come to appreciate the importance of The Hustler.

The Hustler plays a few levels above where he* should, but gets away with it because of sheer willpower, ego and perceptivity. Tweet

The Hustler learns the rules quickly — breaks those he needs to — and dances around those he shouldn’t. Tweet

The Hustler is focused on big vision, but marries that with strategy, telling a compelling and actionable story at all times. Tweet

The Hustler also gets into the nitty-gritty. He’s not just there to wave his arms around and mesmerize people with a vision — he gets things done. Tweet

The Hustler does not network for the sake of networking. The Hustler does not attend conferences to hang out, or pitch his startup every which way. The Hustler isn’t in stealth, he’s just smart about the use of his time. Tweet

The Hustler goes into every meeting knowing exactly what he wants out of it. Tweet

The Hustler is insanely focused. I’m talking crazy, crazy, crazy focused. If you meet someone that seems like a real Hustler but is unfocused, be careful … you’re most likely talking to a Schmoozer — someone who walks and talks like a Hustler but never gets anything substantial accomplished. Beware of bullshit artists. Tweet

The Hustler isn’t a loudmouth. Tweet

The Hustler surrounds himself with talented, complementary people. He knows what he’s not good at and makes sure to bring on the best. Tweet

The Hustler leads by example. Tweet

The Hustler is decisive. He surrounds himself with great advisors, gathers input, but makes the final decisions. And the Hustler does so quickly. Tweet

The Hustler is bold almost beyond reason, not because he’s insane or delusional, but because he knows that’s what it takes. (OK … he’s a touch delusional too!) The Hustler is confident but not an egomaniac; it’s a fine line that The Hustler walks. Tweet

Startups need to be run by a Hustler. The Hustler can’t survive on his own, but I’m not sure a startup without a Hustler is worth pursuing at all.

* I’ve written “he” throughout this post, but it can just as easily be “she”

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  • Ken Seto

    These are great general guidelines but I disagree with the networking part. I’ve seen far too much benefit from serendipitous networking that I don’t believe you can truly plan or be as smart about it as you say. I’d say err on the side of being out there more than you might think you need to be. It’s a win-win if you are more generous with your time and are helping others while you’re at it.

  • Benjamin Yoskovitz

    If I may push back a bit — can you (without revealing names or any info that should be private) specifically list some examples of serendipitous networking that’s genuinely helped Massive Damage?

  • Ken Seto

    It’s actually hard to think of a single example that doesn’t owe itself to previous networking efforts. I think it’s a slow, steady build-up of your personal brand and presence that creates opportunities for serendipity. You don’t get an intro to the top VC firm in North America just because you showed up one time.

  • Benjamin Yoskovitz

    I’m not arguing against networking, but I think a lot of founders overdo it. They hang out in the same circles, with the same people and it’s not moving the needle significantly enough.

    You don’t get an intro to a top VC firm b/c you attended an event either. Or even presented at one.

    But let’s dig in further:

    * Have you ever attended a conference/event, met someone that you later hired, or who later gave you a referral to someone you hired?

    * Have you ever attended a conference/event where you saw a speaker or networked with someone where it fundamentally changed your startup — the product specifically or your vision for Massive Damage?

    The answers may be YES (that wouldn’t surprise me) but how often have you attended an event, “re-met” for the most part, the same people, felt good about it, but where it didn’t really have a huge impact?

  • Ken Seto

    Yes to the first question, no to the second.
    Can’t speak for others but at StartupFest, I didn’t have an obvious agenda so I just decided to help others by making intros an giving them feedback on their pitches and fundraising. It is hard to quantify the effects of that activity but it felt good :)

  • Abdallah Al-Hakim

    I think the networking is a valid point. I make an effort when attending events of not hanging out with the people I know. Hanging with the same people reduces the chance or serendipitous networking. I have seen at least one VC who makes an effort to talk with younger crowd at a conference and even follows up later for a breakfast or lunch meeting.

  • Abdallah Al-Hakim

    this is excellent and reminds me of the ‘the world’s most interesting man’ commercials :)

  • Benjamin Yoskovitz

    I agree that it’s hard to quantify those efforts and it feels good. I do those things too. And I thought about whether or not I should put something into this post that said something like:

    The Hustler helps others all the time, not for glory or fame, but because it’s the right thing to do. And he knows it’ll come back later in some positive way.

    I left it out for a very specific reason though; a lot of people help others –and that’s awesome– but they’re not real startup founders or The Hustler. Build up all the juicy karma you want in the world, do sing-a-longs with your friends to feel good, genuinely add value to the universe … but it’s so easy to get caught up in that and make yourself believe you’re creating value for your startup. Suddenly you’re more focused on helping others, hanging out, doing intros, etc. that you’ve forgotten what you were supposed to be doing in the first place: building a kick ass company.

    It’s similar to my argument re: startup incubators designed to “improve the ecosystem.” Accelerators can do the most benefit by making a shit ton of money off companies that become crazy successful. That’s going to help the ecosystem…

  • James Ferguson @kWIQly

    I disagree with most of these :
    >>The Hustler goes into every meeting knowing exactly what he wants out of it.I go to learn !>>The Hustler is insanely focused.On Cash, Team,Market, Benefits, Compliance, Networks, Product – This is silly
    >> The Hustler isn’t a loudmouth.
    Some are.>>The Hustler surrounds himself with talented, complimentary people. He knows what he’s not good at and makes sure to bring on the best. Agreed>> The Hustler leads by example.And learns by listening – Mentorship is keyThe Hustler is decisive. He surrounds himself with great advisors, gathers input, but makes the final decisions. And the Hustler does so quickly.>> Nope he optimisesThe Hustler is bold almost beyond reason, not because he’s insane or delusional, but because he knows that’s what it takes. Only if he hasn’t got the quiet confidence of a worldbeating team and an irresistable force – Watch how continental plate tectonics move – they build mountains

  • Benjamin Yoskovitz

    James – thanks for stopping by and commenting.

    A couple comments:

    * I don’t think The Hustler is a loudmouth. A loudmouth is a loudmouth, and counter to your point of “Learns by listening” which I do like. You can’t listen if you’re always yapping…

    * Going to a meeting to learn = knowing what you want out of the meeting when you get there. Don’t think we’re saying anything different there.

    * Focused on building the business. Not focused on celebrity, not focused on reading TechCrunch 24×7, not focused on distractions. Focused on the company. What they should be focused on will vary depending on the stage of the business.

    * I have a feeling we’re saying basically the same thing about an “irresistible force” and “bold almost beyond reason.” I didn’t say “bold beyond reason” — the difference is important.

    * re: “breaks the rules” — I’m not sure what rules you think I’m referring to. I’m talking about social norms, finding exploits you can leverage (that aren’t illegal). I don’t think successful founders win by breaking the law — that’s quite the extreme.

  • Jon @jonl1200

    Love this post. Hustlers are a precious commodity, thier diamond in the rough. Organizations should cherish then when found.

  • philgo20

    I would replied yes to both. First being the hire we had been wishing for for months and the second keeping us from going into a dead end by meeting someone I had never managed to get a reply from, face to face.

    But great list nonetheless Ben.

  • Benjamin Yoskovitz

    Phil — I’m glad that’s the case for you. And I know it’s possible to get great, specific results from networking and events.
    But my point still stands –at least in my mind– going to every startup event there is doesn’t make your startup a success. It may be fun but it’s noisy and distracting and creates a false sense of success.
    Ben Yoskovitz
    514 582 4749
    Sent from iPhone, so please excuse any typos

  • JLM


    Fabulous, well played.


  • philgo20

    And I do agree with you Ben. I don’t go to “every startup event”. But I also agree with Ken that there’s value in serendipitous networking and just showing up with your ears open at random intervals.

    My 2 cents.

  • Brian Mayer

    Nice. Based on this, I’m happy to be The Hustler.

  • Jonathan May

    You mean “complementary”, not “complimentary”.

  • James Ferguson @kWIQly


    I think you adopt the term Hustler as positive, and then go on to support this, by correlating it to entrepreneurial-ism which we both respect.

    If you consider “Hustler” conventionally as defined by the urban dictionary.

    “someone who knows how to get money from others. selling drugs,rolling dice,pimpin. your hustlin for that money.”

    You will see my start position and it is not someone I care to associate myself with, (nor do you I suppose :)
    So – perhaps you chose a provocative title to win attention (and it worked), I do the same. But for the reasons I gave I believe you are trying to redefine the vocabulary and not concentrating on description of the honest hard work ethic that a startup founder must have.

    Please also note – I am debating and not seeking to offend – I am sure your integrity is not that as suggested by the term “hustler”.


    Well put, Ben. Regarding the Networking thing: I agree with you. You shouldn’t be at a networking event if you haven’t done the research of who’s there, who you need to meet and know exactly why you need to meet them. I think three people is the max number of people you can create meaningful connections with at an event. Meaningful connections happen when you prepare and do your research on them. That takes time. I’d say a hustler is at a networking event if he knows exactly why he’s there. There’s serendipitous encounters at the grocery store but you don’t go there to find them. The opportunity cost of the six hours involved going to a networking event at a startup is way too much time that’s better spent on something else. If you could go to every networking event without giving up anything, we’d go to all of them but that’s not the case. Time is way too important for a startup founder.

  • Paul Careless


    100% on the money. Every. last. bit.

  • William Mougayar

    As a hustler myself, I like all of them except the one about being a Loudmouth. Maybe it’s the choice of words, but a hustler needs to be a mouthpiece/spokesperson for what they are doing. They have to say something.

    But it’s a great list. Besides Jevon, who else do you consider as model hustlers in the Canadian scene?

    Oh, one more thats related to your last one. A hustler never takes No for an answer.

  • Benjamin Yoskovitz

    William – of course The Hustler has to say something, but to me, a loudmouth is someone that speaks when there’s nothing to say. It’s someone that would rather hear the sound of their own voice over anything else. Loudmouths don’t listen, they blather…

  • Benjamin Yoskovitz

    Thanks. Appreciate it.

  • Benjamin Yoskovitz

    Yup, fixed.

  • Benjamin Yoskovitz

    No one’s offended … but the term “Hustler” has been used by many in the entrepreneurially community, not b/c of the definition as you’ve described it but as something different, which is what I’m describing in the post.

  • James Ferguson @kWIQly

    OK Ben – I have not seen (or have not noticed) this elsewhere. If I substitute “go-getter” for “hustler” it makes sense largely – which is your point I think.
    BTW I do enjoy some of your other posts and insights :)

  • jonathan hegranes

    Lacking amazing coding skills, I fall squarely in the ‘hustler’ camp — and this list speaks to me on many levels!!

  • Benjamin Yoskovitz

    Glad you like the list Jonathan. But it’s important to note that hackers can be hustlers too. A Hustler isn’t someone necessarily w/o coding experience, although it makes sense for a non-coder to “fill” that role.

  • alexeberts

    Great stuff Ben – I’ve printed this out and put it over my desk! Let’s get together for a beer next time you’re in MTL.

  • Benjamin Yoskovitz

    Beer sounds good to me. Glad you liked the post Alex.

  • Kirsten Lambertsen

    Nice, inspiring post for us hustlers. I am definitely a hustler – everyone is always telling me that’s my gift :) (Right now I wish it was coding, ha!)

    I would like to add that hustlers are always giving to get. Hustlers know that offering to be of service first is the best way to create a powerful loyal network. Hustlers are givers.

  • Michelle Bixler

    Great post! This should clarify any confusion related to “hustler” or any context of the word when we (startup/entrepreneur community) use the term.
    Hustler (noun) #1 Hustle (verb) #1#2#3 The verb can be used at different levels depending on the person. :)
    1. an enterprising person determined to succeed; go-getter.
    2. Slang . a person who employs fraudulent or unscrupulous methods to obtain money; swindler.
    3. Informal . an expert gambler or game player who seeks out challengers, especially unsuspecting amateur ones, in order to win money from them: He earned his living as a pool hustler.
    4. Slang . a prostitute.
    5. a person who hustles.
    HUSTLE hus·tling, noun verb (used without object) 1. to proceed or work rapidly or energetically: to hustle about putting a house in order. 2. to push or force one’s way; jostle or shove. 3. to be aggressive, especially in business or other financial dealings. 4. Slang . to earn one’s living by illicit or unethical means. 5. Slang . (of a prostitute) to solicit clients.

  • adamslieb

    Awesome. Thank you for the defense of the hustler. I hear a lot lately about hackers & designers, both critical to startups, but sometimes I see the hustler get pushed to the side as if “anyone could do it if they tried.” I appreciate this.

  • Benjamin Yoskovitz

    Glad you liked the post — but to clarify: hackers and designers can also be the Hustler. A Hustler does not automatically = a non-technical founder. I’ve argued in fact in other posts about the fact that non-technical cofounders are problematic as well.

  • adamslieb

    Absolutely. Good clarification. These aren’t necessarily mutually exclusive. My particular sensitivity is to people that think that if you are an A quality designer/hacker, you can easily just become a hustler. I would argue that transition is just as difficult as a non-technical founder who decides he is going to be an A quality hacker. Sure it can happen, but it is exceedingly rare to find an A anything, even more rare that you will be A at two things.

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  • Amrita Mathur

    Question: In the context of a startup, can a Growth Hacker be a Hustler? Or is the GH the loudmouth that the Hustler is not?

  • Benjamin Yoskovitz

    I think a GH can be a Hustler, but not sure they’ve got the all-encompassing view of a company to be THE Hustler. It’s splitting hairs a bit, and the definition of a Growth Hacker is in flux somewhat as well. I think a GH spends most time building user base vs. anything else. The Hustler — particularly as I’ve defined the Hustler (which is really as CEO) — is doing more than that.

  • Amrita Mathur

    You’re right, there’s a bit of overlap so feels like splitting
    hairs. Basically, the Hustler is a CEO/Founder archetype, while the GH could be an early hire that is focused specifically on growth. Would it be fair to say GH = user growth while Hustler = company growth?

  • Benjamin Yoskovitz

    I think that’s a good way of defining GH vs. Hustler, particularly if we define user growth and company growth as equally success.