How to find a Hustler?

We’re an techies-only, 100% bootstrapped startup. We’ve got a great (working!) product, some paying customers, and quite some traction within our niche. Which is nice πŸ™‚

But we need to sell more. Right now, our team is composed of Hackers only. Read: the product sells itself. So we feel the time has come to add a Hustler. And maybe a Hipster in the longer term, we’ll see.

And so the question is triple.Β First: how do we find a good Hustler, what channel do we use? Secondly: adding someone to a small team is quite a risk – what if it fails! What are practical ways to limit this risk? And third: probably linked to question #2: what do we offer him/her?Β 

Thanks for the input!


  • First the hackers need to learn how to hustle (do sales) themselves. This way you’ll figure out what works and what doesn’t, and you’ll be in a position to evaluate whether potential candidates are suitable for the job.

    If the person doesn’t work out, fire them. The first few hires are super risky, which is why you shouldn’t hire anybody unless you absolutely need to. When you hire somebody to do a job you don’t understand you’re setting yourself up for failure.

    • No offence, this is an absolutely terrible answer. Sales is a significantly different mindset and product development always sucks at product marketing/sales.

      • I disagree (or don’t think you understand the point the person is making) and no offence to you either.

        Of course sales is a different mindset from product development all together and I don’t think they were implying that they try to fill that role going forward. Just that they can learn an awful lot about their market, product and what they need in a sales person by putting in the initial effort themselves.

  • If the product sales itself, then why do you need a hustler? You need to spend more on advertising and promotion. If the product needs some help selling itself, then you need to look for a sales rep who has worked in a startup environment before. Trust me, hire someone from a big name and you are heading for disaster. If you are looking to add resellers/business partners look for companies where your product helps them sell more of their product.

    • +1 on hiring someone who has done it successfully at a startup before. They can be pricey but are so much better qualified than people who come out of big companies.

  • Outsource to East Europe. Have a look at Estonia and Latvia (don’t mess with Litheania). Despite dict-p in Belorussia goverment there strongly supports outsources. In Russia look at Novosibirsk – a town of science (Moscow and St.P. are very expensive – USD3000 and USD2500 per month respectively).

    • Seems like an answer from someone who has no clue about being a founder member. Let us help this friend out.

  • A hungry horse is better than a fat elephant. Unfortunately you’re going to have to keep trying people until you find one that works. Look for smart, hungry people that have ridiculous hustle stories and get your product. Don’t be fixated on prior experiences / titles.

  • You haven’t said salesperson, you’ve only said Hustler. But to clarify, I don’t think you want to hire a salesperson. Here’s why:

    As a hacker myself, I think it’s really tough to manage the technology and the business. Personally, I would make it your goal to change the markup of the team such that one person is running the business (making sales, setting vision, building audience) and someone else is managing the technology.

    Two ways you can do that:

    Hire another hacker, and one of the existing team members becomes CEO.
    Find a CEO

    Find other software startup CEO’s you respect, and ask them about their day to day to find out what being a startup CEO is really about. A CEO of a small team is really cheif executive, finance and sales officer. Sometimes marketing too, depending on your business model. You’ll need marketing eventually. A lot of teams usually make someone else on the team chief of technology and product, which is difficult in it’s own right.

    Really, its however you want to divide up the roles. I’ve just found that trying to be CTO/CEO is really hard. I think you already know that CTO/CSO is tough. Honestly, CTO/CPO can be at odds in the same person, but startups seem to make it work.

    Hopefully this helps you determine the roles your team is lacking, and what you should be evaluating for. Actually evaluating for those things is beyond this anonymous answer, but talk to people who you respect and have been through the early stage already.

    • That’s the dumbest thing I’ve ever heard. While they need to know about business themselves, hiring another hacker won’t help. They need diversity to succeed.

      I really want to say that real hustlers find you, but as a hustler myself, I know that that’s a 50/50 shot.

      You need to go to meet ups and/or research startups with traction that may be lacking hackers. Like ones that have customers already or tech that was built by a contractor in the U.S. or in China or the Ukraine. Trust me when I say China or the Ukraine. Pitch them your “it sells itself” product. Let them use it. You know when you are in the presence of a hustler and if they get excited about your idea and have feedback to help you get more customers, improve the product, build a relationship with them. They will want to help you. If you like them, ask them to help you. If they say yes and are worth their salt, they will have you more customers within 90 days.

      The other note – if your product sells itself, you wouldn’t be in need of a hustler. There’s something wrong. I know you think it’s great and it may have excellent potential… But if you aren’t connected to your market or it’s not solving a pain point for customers, it needs to be modified. Check those two things first before wasting a real hustlers time. Something tells me that you aren’t going to believe them when they give you feedback when you say things like “sells itself”.

      Most hackers don’t realize this, but hustling is a science and an art as well. Great hustlers have the innate ability to connect dots and see behavioral patterns and statistics without realizing they do it. There’s a genius and survival instinct they have that most hackers won’t ever have. It’s not that one is smarter than the other. One specializes in Selling product and the other in building product. It takes different mind sets.

      Good luck finding someone and REAL hustlers will work on 100% Commission. They will take equity or a percentage of sales/contracts. If they don’t want this, they don’t believe in your team and/or product. RUN.

  • OP here. Thanks for the answers!

    On “it sells itself”: what I meant was: our current (limited) turnover is not the result of us doing sales, because we don’t really, so it must be because we build something people need.

    I did not mean that we hit the motherload πŸ™‚

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