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5 Things NOT To Say To an Entrepreneur

Until I started my company, Headbands of Hope, I probably would have said some of the points below. Honestly, I didn’t know what to say and what not to say to entrepreneurs until I became one myself. These are all easy mistakes to make.
Therefore, I want to establish 5 things not to say to an entrepreneur…


1. “Why don’t you go on Ellen?”

You want the real answer? I’ll let you know if she decides to respond to my dozens of letters and headbands. I hate to break it to you, but being on a talk show with millions of viewers isn’t a groundbreaking idea. Being on Ellen or any of the big media opportunity doesn’t happen because you decide you want it. Trust me, Ellen and Oprah have received dozens of headbands and letters from me. Someone telling me I should be on World News or Good Morning America doesn’t help anything but remind me that my efforts haven’t worked yet. I appreciate marketing ideas and suggestions, but do me a favor and filter out the obvious.

2. “How much does it cost to make your product?”

Do you want a copy of my paycheck too? Never ask an entrepreneur their distribution costs. It’s really none of your business. No matter what their answer is, it’s asking to be judged on their profit margins. I understand you might be curious or you want to seem like you’re interested in the dynamics of the company. If you want to show your interest, ask about their inspiration behind the idea, not the cost of it.

3. “You should…”

I don’t have kids, but I imagine when someone tells you what you should do with your company, it’s the same feeling a mother gets when someone tells her how to raise her child. Never start your sentence with “you should…” I’m not being closed-minded. I appreciate suggestions and feedback. However, when someone tells me to do something like, “you should put more pictures on your website,” or “you should make winter headbands” it makes me feel like you’re telling me what to do, not suggesting it. Instead, ask, “would you mind if I gave you my feedback?” Or, “I have a couple suggestions. Mind if I shared them with you?” This approach is much more respectful. I’m more open to hearing ideas you have if you ask me instead of telling me. It also helps if you back it up with reasoning. Instead of saying, “you should get more pictures on your website.” Say, “Pictures really tell the story of your company and what you do. I think the more pictures you have on your website, the easier it will be for people to hear your message.” This shows that you’ve done your research, you believe in what I’m doing and you want to give a helpful suggestion. Next time you have an idea for an entrepreneur, ask them first, then give support for your suggestion.

4. “How many people work for you?”

You may not see it this way, but this question sounds like you’re measuring a company based on the number of employees they have. No one looked at Harvard and said, “if only they had more professors, then they’d be a good university.” Tumblr has only eighteen employees, and I think they’re doing alright. Just because you can hire someone, doesn’t mean you should. I never thought I’d be doing all my own graphics but I didn’t have the funding in the beginning to hire someone to do it, so I did it myself. I would argue that hiring too many people could kill your company. Too many cooks in the kitchen can dilute the mission and culture of the company. Also, with technology, you can wear a lot of different hats instead of hiring people for individual needs. What I’m trying to say is how many employees you have or if you have someone that does your laundry and brings you coffee isn’t a measure of how successful your company is. So maybe leave this question out.

5. “I want (insert product). Can I have one?”

Just because we own the company, doesn’t mean we get our products for free. And just because you know the CEO, doesn’t mean you’re entitled to free products. If I want to give you a discount or a complimentary headband, I’ll give you one. But it certainly won’t happen if you ask me for it. If you were a good friend or family member, you’d understand that one of the reasons I started a company is to make a living. Sure, it may seem like just one headband, but it’s more than that. Not only do they add up over time, asking for free product shows you’re not supporting what I do. If you offer to pay and I say no, that’s fine. But don’t assume since you’re making the purchase through me that it’s free. A good way to approach an entrepreneur about getting his or her product is, “Hey, I really love your (insert product here). Would it be easier for me to purchase that through you or should I go online?” This shows that you want to support the business, but you also want to make it as easy as possible for the entrepreneur to make the sale. This also makes me aware that you want the product so if I want to give you a discount, I will. But don’t assume that. That’s great that you love my products and what I do, but respect me enough to make a purchase and not ask for me to pull from my inventory.
Like I said in the beginning, these are all easy mistakes to make. I didn’t realize the sting of them until I was on the receiving side.
There are some things people say that are more obviously wrong like, “When are you going to use your degree?” or “It’s not the right time to start a business.”
Or, my favorite, “you’re too young.”
Those quotes are extreme (but they still happen). The above 1-5 points are just reminders that you might not have realized before. If you have an entrepreneur friend, significant other or family member, just remember some of the points above. And as always, support is the best thing you can communicate.
Jess Ekstrom is the 22-year-old founder of Headbands of Hope and Headwear of Hope.