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My Worst Client Experiences and What They Taught Me

Part of being an entrepreneur means putting on your customer service hat and serving people well – but what happens when things go bad? What implications does it have on not just your business but your life? And how do you pull yourself out of those situations and use them to sincerely grow? I’ll be honest, in my seven years of entrepreneurship, I can count these awful experiences on one hand – maybe two if I took some time to really remember the things that I’ve likely blocked from my memory but when I look back, those were some of the best growing moments in my business, even though those times were rough – like really rough.

So today, I want to break down some of the worst experiences that have happened to me in as an entrepreneur and then shed a light on what I ultimately ended up learning the really hard way.

The bride who wanted a refund:

I’ve never shared this story publicly, probably because I’ve willed myself to forget it but it’s time to share about one of my first weddings EVER and how the bride came back months later asking for a refund. There were red flags from the beginning – there usually is – and I ignored them because I was just starting out, I needed work, and I was willing to bend in any requested direction in order to get my start as a wedding photographer. The couple was in a fight on their wedding day and refused to shoot photos together, they grumbled when I asked them to post and avoided one another at the reception meaning it was impossible to get many photos of them together… Okay, typing this story is too complex for a blog post, but you’ll just have to tune in to hear all the juicy details!

The deleted memory card from a wedding day:

I’ve told this story on the podcast before – because even when I think about this today, I still feel like I’m going to throw up. It was my first year of shooting weddings and I had a wedding season with 25 weddings. I had one of the most incredible couples, Brooke and Rob and I was shooting their wedding day alone. They didn’t do a first look, so I went to be with the guys, did their photos, then went to be with the girls and did their photos.

    • I need to have systems for everything: how I prepare for wedding days, where my memory cards go, how to differentiate what is full and empty, no re-formatting cards on wedding days.
    • I need to have a second shooter for every wedding (and I’ve had one at every single wedding ever since.)
    • I have to slow down and be prepared for anything and everything. This changed how I carried my gear, where I left it, how I stored it, and my entire backing up process.
    • Work with people who believe the best in you. Rob and Brooke were so incredibly kind, gracious, and forgiving. I remember just crying and apologizing.
    • I offered to move heaven and earth for them – offering them photos for life! I’ve photographed them twice since and met up with them on a vacation.
    • Mistakes happen, you have to own up to them, face them head on, and then figure out your plan to never let anything like that happen again.
    • Have a contract in place that protects you but also protects your clients, contracts don’t need to be scary legal documents but more of an expectation setter when situations arise. jennakutcher.com/contracts

The person who hated my course:

If you do any sort of online education, you’re bound to get the person who thinks what you teach is absolute garbage and they want their money back. Now, coming from a girl with a refund rate of less than 1%, I am pretty darn confident that my courses are filled with good, tactical information, and they truly help people but trust when I say, it’s not easy to hear from the people who sincerely want to hate on the content you worked so hard to create.

The first time I got a refund request, my heart sank and I immediately questioned EVERYTHING. What am I teaching? Do I even know what I am talking about? Why do I think I’m qualified to do this? I remember when I was talking with someone in the industry and she asked me who was going to handle my support for the course and I said, “Well, I am, silly!” and she warned me that I should get help and let that help serve people – especially the unhappy ones so that it doesn’t threaten to steal my shine.

Well, that advice was well warranted because she was right. The first time someone wanted their money back for content they had consumed, I was devastated… I wanted more information from them, I wanted to know how I could do better or where I went wrong. Unsatisfied customers can be a wealth of information, so here’s what they’ve taught me:

      • Refunds can’t mean failure, they have to mean that you’re casting your net wide enough.
      • If you aren’t getting ANY refunds, chances are, you aren’t reaching a broad enough audience with your message or offer.
      • There will always be people who don’t think like you do, use your judgment and honor what they are saying. If you can learn from them, do it, if it’s just crap cast on you due to their own insecurities, let it go.
      • Set up boundaries that will protect you from refunds. I have my team handle them using their best judgment and I trust them to process refunds and follow up with any requests using the process we’ve created.
      • I ask for feedback from my students and keep track of questions, where they are getting stuck, and ways we can update the content to make my courses the best ones out there.
      • Refunds can teach you a lot about any holes you have in your program or pitch, so it’s good information to have.

Haters on Instagram:

If you listen to this show, it’s no surprise that you know that I’ve gotten my share of hate on Instagram. It’s nothing new, it’s nothing that really needs to be talked about at length, but it’s absolutely taught me a ton about running a business, having a platform, and knowing how to respond when nasty things are said to you or about you. From being called “fat” to being blasted for being a scammy saleswoman, I’ve gotten hit with my share of nasty internet trolls. I think people can’t believe that it happens or when you hear someone else talk about it, you want to shake them and tell them: just focus on all the good, don’t give them the attention or energy they want, but when it’s actually happening to you and you’re attacked, it feels so personal. So here’s what it’s all taught me:

        • Those people who have a million followers? They’ve also got thousands of haters, so before you think they are living the dream, remember that everyone is facing adversity and I honestly don’t envy people like the Kardashians who get so much hate on everything they post.
        • Fight the urge to fight back – seriously, give people who leave you love more attention than the haters BUT if you ARE going to respond, do so in love. Hurt people like to hurt people and it’s easy to want to say nasty things back, but just refrain. K?
        • Don’t delete the bad stuff, let your tribe see how you rise up — and trust me, if you have a true community they will go to bat for you, just make sure it doesn’t turn into more bullying in the form of comment wars.
        • Shoot the person a DM to show them that you noticed their comment and start a dialogue, you might learn something new — or at least remind them that a human is on the other side of the screen in case they forgot.
        • No matter how kind you are, there will be people who just want to get attention or a rise out of you – don’t give them that joy.
        • If you need to block, do it and move on. It’s your platform and you’re in control of what you let into your life.

Being copied by people I trust:

Episode 47 was devoted to being copied – because if it’s ever happened to you, you know how much it sucks. I’ve had some pretty crazy experiences when it comes to people copying whether it was something that just felt a little fishy to being ripped off word for word on an hour-long webinar, I’ve been through it all and kept pretty quiet – because it doesn’t really get you anywhere to blast anyone. One circumstance that totally derailed me for a few years was after I started mentoring other photographers.

I would spend anywhere from an hour to a day with a local photographer and open up my entire process for them, giving them access to all of the resources I created for my business and sharing everything that I believed had led me to a 6-figure photography business while living in a small town. Well, in one circumstance, I had shared everything with a girl I was mentoring from my email templates to my pricing guide only to find out an entire year later that she was using the word for word but undermining my prices by a few thousand dollars. I found out because someone had inquired with both of us and noticed and called her out with me CC’ed on the email. I was SO disappointed, so crushed, and so hurt that not only had she taken advantage of what I had given to her, but also that she had been undermining me for over a year.

I was tempted to hire a lawyer because I knew that her decisions had ultimately impacted the bottom line of my business but we ended up settling out of court and she fulfilled terms that I set (which included paying me for loss of income) but this one situation sidelined me from ever wanting to teach again. It literally made me rethink everything and held me back from sharing ANYTHING for a few years. It’s really scary to think if I would have continued to let that fear win, because it was strong and I was fragile. Thankfully, I started to open up again and started to share, because at my heart I believed in community – not competition but after being burned so intimately it made me really question if I could share information with the true hopes of helping others.

          • You absolutely are in the right to defend your business but you have to 110% sure that the copying was intentional, that it was known and it just isn’t a few similarities. Have an extra set of eyes help you to decipher if you’re being sensitive or if it’s an intentional case of copying.
          • Take the high road and remove emotions. One of the biggest things after being copied is that you’re likely emotional because you care about your work, but the thing about being copied is it can ultimately impact your business and income. So when you are copied you need to remove that emotional aspect and look at it from a more business/income standpoint.
          • Screenshot everything so that you can show side-by-sides of what is being copied and have proof in case denial happens. In the best cases, I’ve shared the side by side and addressed the issues so that it is clear why I believe I am being copied and what I request to be changed.
          • Do your best to preserve the relationship, if you remove the emotions and approach it from a: here’s what I noticed, here’s my concerns, would love to work with you to remedy this and move forward. Friendships can be lost over this, so it’s important to really aim to preserve the relationship.
          • Don’t harvest bitterness, if you approach it and they deny you have a few options: let it go, like really, let it go. Use it as a challenge to change up your own stuff. Hire a lawyer to help you.
          • Keep your head down and do your best work, because at the end of the day there is only one you and when you truly believe that, the threat of being copied suddenly seems minor when you know all ya gotta do is focus on shining the light only you can shine.


So there you have it, the top 5 bad client experiences I’ve had that have shaped me – let me tell you, there are countless others that can’t be covered on one episode but if I’ve learned anything, it’s that everything can move you forward — even the crappy stuff. The truth is, no matter what type of business you own, you will face those critics and the stuff that makes you want to throw up or throw in the towel, and maybe you roll your eyes whenever someone says, “I still wouldn’t trade it for the world because it taught me how to move forward” but it’s true: those hard times challenge you and make you learn how you can be better, do better, and serve better.

I’ve learned a lot in my seven years as an entrepreneur and can only imagine that every day I’ll keep learning! Whether you’re riding high or questioning everything today, I want you to know: you’re doing a great job, keep doing big things, and don’t shy away from the call! You’ve got this, Goal Digger!


by Jenna Kutcher 

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