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My Tae Kwon-Do instructor is looking to make a little extra money on the side. He's hired me to do some graphics work for him, which I'm more than happy to do, but now I'm beginning to wonder if he's done his research.

The area he's looking to get into is very niche-oriented - there isn't a lot of consumer traffic and the startup costs could be huge. I'm afraid he hasn't done his research and is about to sink a lot of money into something that isn't going to pan out.

I want to tell him this, at least ask him if he's done his research, but I can't just come out and say that. I've only known him for six months, and then only through TKD and the graphics work I've done. We are friends, but I just haven't known him that long. I wouldn't know about his proposed business at all if it weren't for the graphics work. That being said, I don't want to see him sink a bunch of money into something that isn't going to deliver.

How can I tell him what he's doing might be a bad idea? I don't want to offend him by suggesting that he doesn't know what he's doing, but I also don't want to see him sink a bunch of money into something that won't deliver.

Note that I am not an expert in starting up small businesses. It's what my family does, so I know the general principles, but it's not like I've done extensive research on it.

  • 3
    The student has become the master, on the basis of what? - He might teach at home or in a friend's gym as a contract employee (self-employed, a business owner). You both trust each other, now suddenly you question his decision. You don't know he's going to sink a ton of cash into this or if he has spare cash and can easily afford to try. You need to find out more before cutting him off. Has he demonstrated poor judgment outside of his ability to teach. He succeeded in convincing you to become a student what does he need to do to convince you he can operate a larger business? We need more info. – Rob Dec 10 '17 at 23:03
  • @stannius We are self-employed, so running our own business is what we do. We do not, however, have any experience in the field he is looking at. It is a very small field though, with a very limited customer base. – Thomas Myron Dec 11 '17 at 18:17
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    Thomas, I know a dozen people who know martial arts and chose to mention it. Half those people attend their father's business and 3 have there own somewhat successful businesses. They have students with enough experience to guide the newer students while they fly overseas to attend or judge matches. Some places, and sometimes, martial arts are more popular. My prior question was undeleted, I don't know if you missed it. Additionally could they wish to invest as a 'source of pride' to be a small/family business owner - like you will inherit your family business. Why do people climb Everest? – Rob Dec 11 '17 at 23:34
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I would put together a list of common problems and hurdles that you think he might face, then ask him about how he plans to overcome them.

Word the questions so that you are assuming that he is prepared and you want to know how, rather than asking if he's prepared.

If he answers the questions well then you'll know that he is prepared and can rest easy. If he answers poorly then it will hopefully draw his attention to how unprepared he really is.

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    It can come over as very patronising if he detects it as an insincere assumption, it might be best to be honest if you are not 100% sure you can pull it off. – PStag Dec 10 '17 at 23:00
  • Best of all, if he does have a generic plan, this will probably help crystallize it. – Nic Hartley Dec 11 '17 at 7:35
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    This is the best way to help someone who is starting a business refine their strategy: ask them about their plans and challenge their ideas. One important note though : try and understand their business first. – WirelessKiwi Dec 11 '17 at 10:44
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    I could see this working if it's brought up in casual conversation with a friend, posed as being curious and interested in what's going on. However, it sounds like the OP's relationship is more as an acquaintance/business associate. I think this would be very difficult to pull off effectively without obviously questioning the person's business knowledge. – David K Dec 11 '17 at 14:26
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    So don't be insincere. "I heard that's a really challenging market, how are you handling <x challenge>?" – stannius Dec 11 '17 at 19:26
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Honestly, I wouldn't say anything unless or until he asks for your advice. As a former small business owner, I can say with some authority that these problems tend to work themselves out and they do so fairly quickly.

I'm assuming that he'll need to obtain funding for this venture, since you mentioned your concerns about the expense involved. That's typically the first and often insurmountable obstacle.

Where people go wrong is when they invest their own money into their idea. That's a problem because it demonstrates that the business owner was not able or willing to sell the idea to an investor or venture capital firm and so the question concerning the profitability of the venture has gone unanswered.

You are in business to produce creative. If I only accepted programming contracts from small businesses that had a sound business plan, my company would have collapsed, almost immediately.

That said, it is very often the case that prospective business owners approach people like yourself with the intent of obtaining a business partner if you could provide services via your labor that the business owner can't afford him or herself. If you believe the professional relationship is headed in that direction or you believe he can't pay you for the work he's commissioned, one course of action might be to explain that you've had a recent and unexpected uptick in business and that you can only spare x amount of time. Then, refer his to someone else.

Hope this helps.

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    Honestly, having an investor owning a large portion of the business, and making demands counter-productive to how I want to run the business doesn't sound very appealing, so that is why I invested my own money into my business -- and it is doing fine. There are several reasons to not seek an investor. – user4788 Dec 12 '17 at 1:01
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    > Honestly, I wouldn't say anything unless or until he asks for your advice. Not to mention money. :) – Kaz Dec 12 '17 at 2:02
  • > when they invest their own money Oh, the hapless fools! Always use other people's money whenever possible! – Kaz Dec 12 '17 at 2:05
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How can I tell him what he's doing might be a bad idea?

He's starting up his own business, odds are he is fully aware that it might be a bad idea.

Note that I am not an expert in starting up small businesses

Nor do you seem to know his business plan, source of finance or how much research he's done. If you were a close friend or a family member that's fine - but:

I've only known him for six months, and then only through TKD and the graphics work I've done

You don't know him well enough to be questioning his intentions. There will almost certainly be people much closer to him than you who will ask these sorts of questions. Starting a business is not something done in isolation and most people who think about doing so quickly give up when they discover the time and effort that it will cost to do so.

It isn't your place to be questioning him (unless your Graphics work for him is being paid for at a later date in which case I would rectify this immediately). If I've misread your post and you're actually really good friends then of course ignore this advice but from what I can tell you are his customer (TKD) and he is yours (Graphics). Don't jeopardise these good business relationships by intruding on another aspect of his life. On the other hand, if he asks you for advice or your opinion then he is inviting you into that part of his life and such questions about his research are perfectly valid and shouldn't offend him.

If I were in his position and had not asked for your opinion, I would consider your suggestion that I hadn't thought things through to be offensive no matter how you phrased it.

  • There are a Lot of people who start a business without thinking things through. As one of them, I've tried several times to "just wing it" and it hasn't worked, even for small ventures. Right now, it's working, but only as a side gig. I want it to be my only gig, so I need to do more work on the business of it being a business, and this takes a Lot of thought and planning. Researching a business for viability will bring up things that won't just work themselves out. I did the full research on starting a business, only to realize it'd take more time finding funding than anything else. – computercarguy Dec 11 '17 at 18:28
  • BTW, most of the people who start a business without thinking things through fail in the first year, only to have a massive debt to repay on something that didn't make them any money. If you are even a sort of friend to this person, express some interest in what they have planned, and ask questions. – computercarguy Dec 11 '17 at 18:30
  • @computercarguy That's exactly why I want to make sure he knows what he's doing - so he doesn't wind up with a business going nowhere and a lot of debt. – Thomas Myron Dec 11 '17 at 20:28
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How can I tell him what he's doing might be a bad idea? I don't want to offend him by suggesting that he doesn't know what he's doing, but I also don't want to see him sink a bunch of money into something that won't deliver.

Don't tell him it might be a bad idea.

Ask him about his plan and offer any advice you like at that point.

But trying to stop him is not your right. You have the right to offer help and advice, but not to stop him.

I appreciate you're trying to help him not waste money, but you don't know he will and he has the right to try and make a success of it. You need to offer suggestions that will make it more likely to succeed. Sure warn him of a possible fail but the reason to start a business is not always to make money, but the need to try and do it.

Starting a business is, in many ways, always a bad idea. It eats time and it typically won't make a profit for years (they say budget for two or three years of losses). But those are not reasons not to try, they're just things to be aware of before you start. Plenty of people try and fail at starting a business, but even people who fail often regard it as a necessary thing they had to do for themselves and they don't really regret it.

Your friend has the right to try. You have the right to try and help him with advice. But you should not presume to try and stop him.

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It's a pretty common situation and I've faced some of those, so I guess I have an universal approach.

You are trying to appear as an outsider to the problem(since your work is drawing) and tell the person "I've got some thoughts about your plans and I think, you haven't done your homework on the topic and ...", so that what you think his situation is. But rather than stating it, I would like to recommend trying an reversible approach. You've got some thoughts on the topic and your logical chain has come to the dead point, so why don't you state it. You don't need to start with what you think of it, but rather say something like "I do want to know, how are you planing on developing the start-up?", "don't you think it's a niche-oriented field? How can we work with it?", so the conclusion of your dialogue may match your own one as well as it may not, but anyways, you'll get your boss to think of all this stuff himself (with your help as a collocutor) and you will be the one facing the problem with your boss rather than thinking of it as an outsider.

  • I agree with this in using the position of the graphic designer into getting more information. In order to develop the logo etc, you need to understand the target audience, so you can ask him about that in detail and go onto your other concerns from there. – user4788 Dec 12 '17 at 1:06
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I think that in order to tell him correctly that it's a bad idea you first need to establish that what he wants to do, the way he wants to do it, is a bad idea.

I think you need to obtain more information first before assuming that he will fail in what he wants to accomplish. Perhaps making lots of money isn't his goal.

I had two questions up top which I will draw upon for this next section:


  • You don't know he's going to sink a ton of cash into this or if he has spare cash and can easily afford to try.

  • Has he demonstrated poor judgment outside of his ability to teach.

  • He succeeded in convincing you to become a student, what does he need to do to convince you he can operate a different business?

We need more info.


  • I know people who have there own somewhat successful businesses. They all have slow growth and low attendance, but some are devoted and it's those people that they are pleased to teach.

  • I see many businesses where it's entirely clear that the business model is poorly convinced, executed, staffed, ran, you name it.

    It's 50% Advertising Company (to convince people to work their and convince customers to purchase and come back) and 50% Joke and Novelty Store (it's a joke and the novelty wore off long ago).

    Most of those places are out of business when the lease is up, others stick it out for a few years, rarely they have way more money than brains and attempt to peddle garbage for decades.

    Sadly, people have the right to do that unless they are subject to some sort of inspection or certification.

  • He might wish to invest in and develop their own small business as a 'source of pride' to be a small/family business owner - like you will inherit your family business.

  • Why do people climb Everest? The risk and challenges, not to be first or safe.


Simply ask if he understands the costs and success rates of starting a small business, tell him you are concerned about the prospects of growth and wish him success.

We need more info to do a business analysis, but that's getting off topic.

  • Some answers to your questions: He's renting a space in a business center and using that as the school. He intends to run a kickstarter campaign to fund his new business at first. He has demonstrated (like other masters I know) a lack of understanding about advertising and proper business models. He literally waits for people to walk in the door. – Thomas Myron Dec 12 '17 at 1:31
  • Thanks for your answer. Hopefully the business center has a lot of vacancies and low rent. The KickStarter funding is probably unusual, why would people out of town fund him - at least he'll get his answer quickly. Some places sit idle and some (near good transportation like a train/subway station) seem fairly well attended. – Rob Dec 12 '17 at 1:57
  • Remember we aren't talking about TKD here - we're talking about the side business he's looking to start up. That has nothing whatsoever to do with TKD. – Thomas Myron Dec 12 '17 at 4:56
  • ^ i think you should edit the question to make it really clear that the side business is not TKD-related; there are a lot of answers that assume it is. – Rob Starling Dec 12 '17 at 9:35
  • @Rob Starling - To contact Thomas in an answer (where you are here) you need to put an @ sign in front of his name. Your statement is more appropriate as a comment to Thomas' question so it ought to have been placed up top (when placed there you won't need the @ sign since it will be addressed to him by default). In short, Thomas won't see your comment from 4 hours ago unless he comes back to this answer and reads all the comments, he won't have received a Notification. -- I've updated my answer to reflect that the 2nd business is not martial arts related. – Rob Dec 12 '17 at 13:49
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There are two concerns when approaching this individual.

  1. You might deflate his well thought out and discovered bubble in just one second.

    Take care that you compliment him sincerely at first for his innovative idea before you proceed to the point at hand.

  2. Upon advising in such a matter you are saying that 'your inexperience and childishness led you to even thinking you have unveiled a new brainstorming business.

    It is of utmost importance that you tell him your concern about the matter, however being that we want to minimize the insult he inevitably and inescapably(being that we need to save him from this foresighted disaster)has to endure,he therefore, shall evade seeing his face upon receiving your advice,as watching his reaction to the news will immensely add to his shame.

Therefore I advise that upon finishing his message he should not just stick around near him, rather give him his privacy for the moment.

The advantage of this is twofold as some shame shall be avoided and the receiver of your advice upon noticing you took care not to see him at this moment of shame will feel cared for and loved.

  • I don't really understand your final paragraph. Could you maybe rephrase it to make it clearer? Something about the wording is just throwing me for a loop... – Thomas Myron Dec 12 '17 at 5:32
  • So... insult the guy then run away? – Lord Jebus VII Dec 12 '17 at 16:27

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