Work Life / The Dark Side Of Entrepreneurship: When You’ve Got The Client From Hell

The Dark Side Of Entrepreneurship: When You’ve Got The Client From Hell

Work Life Sep 10, 2019

When it comes to being an entrepreneur there are numerous highs and lows. Among the highs is of course, being able to put together your company and clients and getting yourself on the radar. One of the lows (among other things) is having a client from hell. We interviewed a PR professional who candidly told us what she endured, the consequences and how she was able to come out on the other side. We changed the name to protect her identity. This is her story. 

Who Is Vaishali Doe?

Vaishali Doe (as we’ve stealthily renamed her) is an entrepreneur, director, fashionista, all-around inspiration, and a powerhouse in the PR world.

Born in Saharanpur, India, and hailing from the western coast of Canada, she currently manages two companies that she has founded: a boutique public relations agency and a luxury travel concierge service. However, she did not get to where she is today without hardship. And, this is a key takeaway about entrepreneurship – there is a dark side as success isn’t linear and there can be pitfalls.

Coming from a South Asian household, Doe’s career path is not of the usual variety (i.e. doctor, lawyer, or engineer). Doe recognizes that “typically [the South Asian] community has these ideas of what we “should be” but at the end of the day becoming what our parents want takes us away from pursuing our own happiness.” In her case, Doe tells us that she was “fortunate to come from a South Asian home where my parents supported me to pursue my own dreams and aspirations. They never pushed me, because at the end of the day I am doing this for myself and my future.” As such, her words of wisdom for dreamers in the South Asian community is this: “do something that makes you happy and is stimulating for you, live your dreams, not your parents.”

Let’s Get Down To Business:

After graduating from a Hospitality and Management program, Doe launched her first business in 2009. Doe tells us that this venture “was more events and promotions and I started it with my college friend.” Doe later decided to pivot her career and go back to school for PR and Event Management, graduating from a noted specialized college in 2009. She knew this would be the right move as there was a passion within her for the PR industry.

After graduating, Doe explains that she “re-branded to create a boutique PR firm.” However, at the time, she was still located out west and was not fully invested in her new company. Instead she notes that “I created a brand, I spent my own money to do it, created a logo, figured out my vision and I continued to still work at a PR agency, [but] a part of me knew that for me to really launch this company and gain success I had to take the plunge and move to Toronto and I did in 2012. That’s where [my PR firm] really came alive.”

Her boutique PR firm focuses on fashion and lifestyle clients but also puts on fashion and media events.

Client from hell
Client From Hell: Doe’s passion for PR is what has made her a success! Photo Credit:

Doe, saw the need for a luxury travel concierge service that aims to elevate a typical vacation. After six months of planning and securing financing, Doe and her business partner at the time, launched her second business in 2018.

Her PR firm and luxury travel business has led her to work with various multi-national and boutique companies, international hotel companies as well as globally recognized art exhibits and with New York Fashion Week.

Client From Hell
Client From Hell: Doe has taken on a number of hugely successful projects, including New York Fashion Week! Photo Credit:


When The Angelic Client Turns Into The Devil: 

Although Doe has worked diligently to earn her well-deserved successes, entrepreneurship does have its downside, especially because of the independence of the game.

People don’t often speak up about the negative experiences that they’ve had, but it’s so important to air these stories out so others can be mindful of what’s appropriate or not and protect themselves. And this is where we decided to let Doe tell her story in her own words.

Devika Goberdhan: How and where did you meet the client?

Vaishalie Doe: I actually met the client in Toronto. Funny enough I had my own event that evening and had no intention in going but, I decided to go anyways because this is what you do in our business. When I got there this was the first person I met and I felt really great energy and connection with this client, which lead them to stay in Toronto a few extra days to establisha working relationship with [my PR firm].

DG: Why did you take on the client?

VD: In [the PR] industry you always have to be innovative and creative. Having started my PR agency focusing on fashion, I [began] to represent clients in other markets and one happened to be art. [This client was part of the art industry], which is why I wanted to work with them, learn more and be a part of another amazing and creative industry. In the beginning, I thought this client’s work was amazing and creative. It seemed like my firm would be with them for the long run. This was in 2017.

DG: What was understood as the job that you were supposed to do?

VD: Our job as a company was to promote and create attention for this client’s artwork [among other things]. We were to produce events and create exposure [for their work], while also building a team for them. [We also worked to form] brand partnerships and introduced the brand and artwork to larger brands, such as hotels, restaurants, and more. We went over and above what a normal PR company would do. Then, it was our job to work on one of the biggest events for an artist (at a globally recognized art initiative) and that’s when things started to take a turn.

DG: What were the red flags?

VD: Funnily enough I never noticed any leading up to the situation. Everything was amazing. We had even built a friendship and, at this point, we had been travelling back and forth from their city. They had even thrown me a birthday party! And so, it really seemed like everything was going well. My stomach started turning around the planning of [our trip for] for the art exhibit. It was small things, like why are our flights and hotel not booked yet? Why has he not sent expenses for the trip yet? [When asked,] he basically said ‘I am really busy getting things done you guys get all your bookings done and we can deal with it after’. In my mind, I thought everything was fine. So my team and I booked everything, packed up, and headed south for eight days.

Client From Hell
Client From Hell: Even though Doe had to put up the money to book hotel and flights in advance she still didn’t see that as a red flag. Photo Credit:

DG: Was there a contract that was signed? 

VD: Yes, of course. We don’t operate without a contract.

DG: What happened when you tried to get your pay?

VD: The issues [actually] started on the business trip. The trip was unsettling and I knew something was wrong but I am a businesswoman and we still did our job, executed the event, and managed all bookings he had asked us to manage. [Things really hit the fan on] the day we were checking out of the hotel. Someone from my team had gone to check out and I got a call to come to the front desk because our client had not been in touch with the hotel, sent the payment or authorized a form for payment. I paid for the expenses and decided to deal with things once everyone had travelled back home. I [thought] the stress of the project had gotten to the client and when that [we can handle this properly after we all got home]. However, the client was not reachable and was ignoring phone calls and emails. That’s when I knew this was going to be the end of this relationship and it wasn’t ending on a positive note.

DG: What were the roadblocks that you encountered while trying to get your compensation?

VD: When I came back to Toronto I was a little frazzled, to say the least. Instead of being excited about the wonderful event we had just produced, I was chasing money from a client who owed us more than I could fathom. I did what any agency would do: I sent proper expenses, receipts, hours and invoices and started getting fewer responses. Then, I got one email from them where he had turned the tables on my PR firm and basically said we did not do our job. That insinuation that we were confused on what he wanted and [claimed that my team and I] were not needed in Miami and so he was not going to pay for things. Seven months of hard work and dedication had just been disregarded. Later, I noticed my emails were being blocked and he had blocked us from calling. It was the first time in this business I felt hopeless.

DG: So, the client turned on you? 

VD: He turned things on us. He started ignoring us. I realized very quickly that [not only] were we not going to get any money, but I had also lost the time I put in.

DG: Did you ever get your money?

VD: We never recovered a dime from them and for all I knew I had residual income they owed my company. I lost hope and energy to do anything about it. The end result was — in a nutshell — we just never heard from them again.

DG: Why didn’t you pursue legal action?

VD: Call me crazy, but I was not up for a fight. I felt lifeless and when talking to someone in my own family who is a lawyer, I really opened up about everything, even she said maybe it’s best you just move on and it was. It was best for my own energy and sanity, and truthfully I did not want to see them again. I just wanted to close the chapter and heal because I knew that was going to be its own journey in itself.

DG: What about your business? 

VD: I was a boutique agency that just took a very large loss. At the time, I had put so much time into this client and was not giving the same attention to other clients. I had expenses piling up and even though we were slowly bringing on other clients, it was all just paying off this huge debt my company was in. I lost team members. I was struggling.  I really thought this was it for me and I should walk away from PR.

Client From Hell: You never know when they will turn from good to bad.
Client From Hell: You never know when they will turn from good to bad. Photo Credit:

DG: What steps did you take to reclaim your business again?

VD: When this first happened I took a few weeks off and went back to the west coast. I needed to be around family to regain some calmness. I wasn’t fully feeling supported and I just needed to be around people with whom I could talk to, vent to and feel good around. I had to remember why I fell in love with this industry again and I needed to recognize that at the end of all of this, the reason this client received positive attention on their business was because of the work my PR company put in.

With this in mind, I knew I could get back up and reclaim this business again. I started reconnecting myself again with people with whom I trusted in the business, coming up with new ideas, and being present with confidence again. At the same time, I realized the PR business always has risks and things happen, and so I began to think about what more I could do, how can I create more streams of income and be secured for the future of the company. That’s when the brainstorming started for for my luxury travel concierge company and how to create a group of companies that are aligned together.

DG: How did you get out from the debt you incurred as a result of this client?

VD: You know it’s all about making different decisions after something like this happens. A few cutbacks on hours with the team, taking on more work for myself, and also it created a new hunger and passion for this industry again, which I thought I lost. I started creating strategic partnerships. I concentrated on developing my luxury travel concierge company along with rebuilding my original PR firm, which in turn created interest for both sides of my business that ultimately, got me out of a very bad spot.

DG: Looking back, was there anything you wish you would have done differently?

VD: Honestly, no. I have no reason to think this way because even though I did blame myself when I took a moment to realize what I did, my team and I did everything the right way and we worked really hard to please this client. That said, I probably won’t book and stay at a gorgeous hotel before getting my expenses paid. It was a learning experience and I most certainly learned my lesson.

DG: Have you seen this client again since?

VD: I always wondered what would happen if I ever saw them again. In 2018, I was scared because it was time to go back to to that same art exhibit. I was anxious, I was nervous, and I was unsure of my reaction if I saw them, especially as I knew there would be a strong possibility that I would. I remember sitting with my team and them asking me how I felt about going back to and I said: “Before them Miami was a place I loved, and after them, it will be a place I still love.” I loved the exhibit and I did amazing work around the event along with my team so we were not going to be held back by what happened. And it was was amazing and we had another opportunity to work with another talented artist.

DG: Going forward, what behaviours of your own have you changed to ensure you’re protected from a situation such as what happened with this client?

VD: I am more realistic about things. I am not so easily attracted by the glamour and greatness that I think a client can bring. Instead, I worry about the greatness of the service my team can provide. I also know this is business, and so, as much as you will always feel a bond with your client, [it’s crucial to] remember you are offering a service and they are accountable to pay for those. I also have a much stronger legal team now. I am more streamlined with my own team and I am just excited about where we are going again.

Client From Hell
Client From Hell: I mean really, who are we to argue with Eleanor Roosevelt?! Photo Credit:


In Her Own Words: Doe Shares Her Tips On How To Avoid The Client From Hell: 

  • Listen to your gut: I know it’s simple to say but you need to truly believe it, something does not feel right. Talk about it if it still doesn’t feel right, as there’s a 99.9% chance that it’s not.
  • Ask a lot of questions when you feel like your client is acting differently. We don’t know what’s going on in their minds. But, also make it known that you are available for a chat anytime so you feel at ease about things.
  • Do not take on extra expenses for your clients because you “trust” them, especially being a boutique business owner. Be clear on your expenses and list them out and get final approval. Put the expenses directly on their credit card. Or you can ask for 50% of the approved expenses up front before you start making an transactions.

Doe went through a terrible experience that caused to close up shop. However she didn’t, she gave us her advice for any entrepreneur who is experiencing the less pleasant side of entrepreneurship, as she did:

  • Don’t. Blame. Yourself.
  • Always remember why you started your entrepreneurial journey and why it brought you joy and happiness.
  • Don’t feel sorry for yourself because at the end of the day the person who is going to be the biggest reason you failed is YOURSELF.

Needless to say, Doe has moved forward since this experience and, thankfully, no amount of hardship is going to hold this resilient Queen back!


Main Image Photo Credit:

Devika Goberdhan

Devika Goberdhan


Devika (@goberdhan.devika) is an MA graduate who specialized in Political Science at York University. Her passion and research throughout her graduate studies pushed her to learn about and unpack hot button issues. Thus, since starting ANOKHI in 2016, she has written extensively about many challengi...