Advice from a Failed Startup Founder

Advice from a Failed Startup Founder

This business took everything. Two marriages. Two cars. Homes. Money. Sanity. Everything. How ready are you to open a business?

There is no founder on the planet who has lost absolutely nothing in the process of gaining success. If anyone has ever told you that, call bullshit immediately. I refuse to believe that someone opened a business, and shot to success without hindrance of any form. The reason why I say that is because a business is like a needy baby with an ongoing temper tantrum and never eats anything you prepare for it. Constant resistance. Hey, if you’re reading this and you somehow magically were able to open a business and not have the entire world pull you back, then hats off to you. Please direct me to the fairies who assisted you.

Am I bitter? Yes. My business went tits up and three people lost everything as a result, and we’re now all neck deep in debt, struggling to recover. But I am so very grateful for the experience, because it has taught me so much about myself, and about business, specifically how not to run one for future reference. Will I stop? No. This isn’t about winning, or success, or money. This is about life.

So, how prepared are you? I wasn’t, at all, in retrospect. I quit my stable day job thinking that this client we got, being the biggest beverage company in the country, would have been a career changing, life altering move. Big fucking mistake. We did everything right. Set up a limited liability company. Distributed equal shares. Had a solid business plan. Offered a service no one else did. Offered prices no one else did. Gave away a lot of free shit. We should have dominated the market easily. But we didn’t. And it’s taken the last three months for me to finally admit why, to myself mainly.

There are three people involved in this business venture. Out respect for their privacy, I will call them John and Tony. We all know who I am, and I could care less about privacy at this point. (I mean, this entire blog is about my life experiences and it’s not under a pseudonym.) Also, I’m glossing over a lot of the details here. This is two years of constant drama with no day being without some shit happening. So I have to just give an overview, unless you want to read a book, which I’ve not yet written.

Mistake #1: We rushed.

Timing was shit. We got the call on a Thursday to start working on a brand “ASAP”. My mother was having a procedure done at hospital the following day, so my head was pretty clouded with that drama. On Sunday, I was asked for a confirmation. I made a quick decision without being careful. I said yes.

Now, I wasn’t in an unstable financial position at this point, so it didn’t seem risky at the time. We (John and I) were okay. Just had a car on finance and did not have to pay rent where we were staying. But we could not both be working, as this client needed at least 10 hours a day from one of us. So, given that my job was with a company that was a little less stable than John’s, I signed and delivered my resignation letter to my General Manager the next day. I honestly thought this was going to work. I believed it in my bones. I was so very fucking wrong.

We weren’t foreign to the industry entirely, which is why we believed it would work. I had a business plan in my head already, since I was consulting over the last three years in this industry. I knew the competition, I knew the pricing, I knew the work load, I knew what resources we needed, I did not know the people personally, or the lengths some people would go to just to destroy you or snuff you out.

Mistake #2: We didn’t separate our finances.

This business was everything to us. So we did what every new founder does: we poured our hearts, souls, organs, and bank accounts into it. And we also stirred the two together. Never will I ever do that again.

We required a credit card for the business, but because the business was under three years old, we did not qualify for one, so you know what we, the big idiots did right? We used our personal credit card… YES, we made that mistake. Looking back, all I can think is, “Des, you stupid, stupid girl.” So, when clients did not pay on time, and this was our reality, we had to cop the bills. Which meant, we either paid the bills to keep the business open, or ate.

After a couple months of this, we had to make a tough decision. John and I reluctantly went to the bank to take the loan they had been offering us for months. Des, dig that hole girl, dig that hole. And it brought some breathing room, because we had car insurance to pay, and the credit card needed to be cleared. So, for a little while, we weren’t constantly looking over our shoulders in panic.

Now, this is about five months into the mayhem. Which also meant that I had not been paid yet. Which meant that John had been carrying all of the bills, just about, for five months, and some of the business’ as well. You can just imagine the pressure here. There were even days when we didn’t have enough money to put petrol in the car for John to get to work. Yep. All for the love of business. [insert snarky sarcastic comment here.]

Mistake #3: We didn’t really have a backup plan.

This ties into mistake one. We didn’t have a backup plan, because we didn’t think we really needed one. Yeah, if shit got bad, then we would fold, I’d go back out to work and call it a day. But that did not happen. In fact, the very linear plan we created never actually happened. Somehow, we ended up on the other side of the map, in undiscovered territory. Were we prepared? Fuck no. Were we happy? Absolutely not. Was this nightmare going to end? Didn’t feel like it.

So, we brought a third partner on board to help with the work load, since I was delivering a shitty product I was not qualified to produce in the first place (which really made me feel like a fraud to the point that I never wanted to leave the house), and I could not be in two places at once, so I can’t be at home at the computer and out there selling the service. Enter… Tony. Tony was a long time friend of mine, who was an experienced designer with lots of awards to his name. Tony was freelancing and looking after his newborn baby girl, one year old son and wife, when I approached him with the offer of being a part of the agency. His freelance business wasn’t doing too great, so he took me up on my offer. The risk was big, but so was the reward, and his talent and skill opened a lot of avenues for us. So this meant, we could do more… and make more money… HA. HA. HA.

This was not a part of the linear plan we had. This now meant that we had to hold our course, as there was now a very real risk of two children not eating as a result of us not getting the job done, or building the company. This was my motivation to get everything moving. And we were moving at a good pace.


Mistake #4: We were too hungry.

We were like blood thirsty ravenous wolves, which meant we took anything we got. We were desperate. We took work on for half the price, and sometimes did not even bill for it. And this cycle only got worse.

We did this for the love of the business and the brands we worked with. We got emotionally involved. Another fucking mistake. Getting emotionally involved in what you do gives the other person the upper hand. In the end, these clients easily turned around, after all the work we did for them, and went with a competitor, not because of quality, or even price, but because of nepotism. We trusted, and we never saw it coming. That hunger is blinding.

Don’t get me wrong. Being emotionally involved about what you do isn’t always a bad thing. It’s sometimes even a good thing. What’s bad is when the person you’re working with doesn’t share that passion and interest, and it becomes one-sided. Save the passion for your personal projects, and your own intellectual properties, not for the clients’. In the end, the only person who will lose is you. And you’ll lose big time. It’s a business, and think of it like that. That’s what we did not do.

Mistake #5: None of us were cut out for this kind of industry.

“Know who you are getting into bed with,” rings true here. I knew both John and Tony fairly well. I lived with John for five years and I knew Tony for an odd ten years. But did I personally really know them? Honestly, in retrospect, no. John and I had grown so far apart and neither of us really wanted to admit it for fear of being alone. Tony and I spoke once or twice a year, always about some business idea, but beyond that, we hadn’t spoken much in nearly 8 years. And John and Tony didn’t previously know each other. So, I was the common ground between everyone. And guess what? We all had serious trust issues.

To further compound that issue, we were all highly emotional creative people. We were all super passionate, but all suffered from severe depression, and were all quite volatile. Again, something you only see in retrospect. We all had our own personal issues which only grew with the stress of starting a company. Lots of hours had to be dedicated to this, and as tensions continued to rise, so did the number of and intensity of arguments. This was a business made up of two young families, on the brink of starvation and holding onto life by a degenerating thread.

Now put that combination with what was happening above. Add the fact that clients weren’t paying on time. Add in the increasing arguments. Add in the emotional attachment to our work. Add in the sacrifice of time and money for people who did not give a shit. What do you get? Chaos in its purest form. Everyone turned on each other in some way. And it all came to a head one night. I had enough and called it quits with John. This caused more stress between the partners and how we were going to separate the business. Within two weeks, Tony and his wife split up. It was nothing short of hell.

If I could do it over, what would I do?

Nothing. If I had to do it again, I wouldn’t. I wouldn’t open the business because I cannot work without investing myself into what I’m doing. It’s just how I work.

Today, I am 23 months into this nightmare. I am now finally able to sit up, and not be flat out on my ass. I’m not yet in a position to stand, or even think about crawling or walking. But I’ll get there.

Do I regret this? In some ways, yes, but as a whole? Not in a million years. I have gained some very valuable insight and hopefully, I can pass that on to you, so you can learn from those mistakes.

Now here is the interesting turn of events. If none of this happened, I would not be sitting in England, writing this. I would not have had that push to come back home and I would have been struggling with the same issues back in Trinidad. Also, by having these extreme circumstances, I’ve learned a lot about myself, the way I work, what really motivates me, and what I want out of life. It has also prompted a complete career shift, and has opened avenues I had not previously thought of before.

So, while it is a pile of shit and I feel like it was unnecessary and none of us deserved this heartache and stress, in many ways I am grateful for it, because it’s brought me to this very moment, where I can now, finally, build my life as I want it.

Another important lesson in all of this is my situation opened up a lot of avenues for me to see what people truly are. I’ve seen who I can and cannot trust and that experience and knowledge is invaluable. I’ve also seen how cruel people can be when all you’re doing is fighting for them. I’ve learned what real support is, what genuine people do and how to sift out the people who have a hidden agenda. I wasn’t completely naive to this before, but I’d be lying if I said I knew it could have been on this scale. Quite an eye opener this has been.

And now…

Advice time:

Take your time. Do not rush this. Write a business plan. Take six months to evaluate the market. Do not quit your day job. Think about what you are doing.

Start small. Do not quit your day job. Slow and steady. Do not depend on the money. Save as much as you can. Bootstrap everything. Outsource as much as possible. Don’t quit your day job.

Do not panic if you see a competitor pop up. Competition is good and healthy. See how well they do; it is an indicator of the market health.

Be passionate, but trust no one but yourself. Clients and companies do not have your best interest at heart. Always safeguard yourself. Do not get attached or emotionally involved. The world is very selfish, and it takes nothing for someone to pull the rug from under you. Trust in only you.

You are not a charity. Repeat after me. YOU. ARE. NOT. A. CHARITY. Do nothing for free, because people do not respect free. Charge full price. Stand your ground. Do not quit your day job.

Know your partners. This might be a bit tough as stress and certain situations can change this, but put as many safety measures in place if you’re not sure. Always be careful.

Have a safety net.

Do not quit your day job.

Why is Business Planning Important?

Why is Business Planning Important?

We’ve all wondered if a business plan actually makes sense.

I didn’t do a thorough business plan for my first serious startup and it flopped, in ways I was not expecting it to. My justification for not taking the time to do it, was that it was all in my head and we didn’t need it because we were all aware of the financial milestones ahead, but I did not take into consideration that my two business partners weren’t psychic (neither were the employees) and probably needed validation that the idea would really work. Six months and six clients later, the partnership broke up, and the remaining two founders had no plan to keep us grounded and focused in the chaos and stress. So, we spiralled out of control until we hit ground bottom. And then we did a business plan.

A business plan keeps you focused and grounded

When the monkeys are running around like headless chickens and the storm is raging, you’re going to be grateful for that business plan. Many times, a business will start at point A, and the right path should be A through B through C, et cetera, but what tends to happen is A, F, X, W, H… ERJUIP… NQYBZ…. A business plan helps you to expand your business in a healthy manner, and keeps you on the right track, so you won’t have a host of disjointed items and a confused consumer market. It’s a good place to refer to when you’re stuck, or disenchanted.


A business plan holds you accountable with milestones

Milestones are key to businesses; they keep us accountable with a date. They also tell you from a glance where your business should be in year or two from now. As a business owner, or even an employee, you can think of milestones as personal KPIs that you’re trying to reach, so every little bit contributed to the overall effort helps. Milestones also indicate to employees that you have a vision and a plan; you’re going places! And if you miss a milestone, you can rally your team together to try to make that milestone happen.


A business plan helps you in a ugly times

Any business plan should highlight the major threats which exist to put you out of business, or to cause you to fail. Once your risks have been properly assessed, you should have some step by step guides to tell you how to deal with your situation. This should (or may not) keep you from panicking and making the wrong decision. So many startups fall at the point where they hit a snag, because there is no planning in place that looked at where they could go wrong; in fact, most startups don’t have a business plan due to a lack of knowledge, a lack of funding to pay for one, or a combination of the two.

Can anyone write a business plan?

Can anyone perform open-heart surgery? No. So why do we so often try to do specialized tasks ourselves and become disenchanted by the result? Business plans should be written by someone who can map your business out properly, while looking at all of the possible instances or roads your business can take over a defined period. It’s also unbiased and removed from your emotional attachment to your business idea. If a business plan is the blueprint to a business, I wouldn’t want just anyone writing mine.

A business plan should also provide some level of validation and comfort that your business is in fact possible, and should give you enough courage to push through regardless of the circumstances.

So, if you have a business idea, it’s time to validate it with a proper business plan.

Not Keeping Promises to Myself and my Struggles as a Writer

Not Keeping Promises to Myself and my Struggles as a Writer

When I made the decision to start writing and blogging again, it wasn’t an easy one. I’ve always felt very naked and exposed, and always got nervous when I realized that someone out there was reading my words, the words which I clacked out on the keyboard. That feeling was also far worse when someone I knew personally was reading my work.

One lucky blessing is that I’m now in a relationship with a writer, and we’re able to encourage each other, share notes, and validate each other’s words. Validation is an important part of writing, especially in the beginning; in fact, validation is a really important part of being human. He can tell me where I’m going wrong, because he is a far better writer than I will ever be, and give me clear, concise criticism in my weaker areas.

A piece of advice for new writers: if you don’t have a writing partner, you should join a group, whether physically or digitally, for writing support because it’s vital, especially in the early stages.

Today I updated my Twitter and Instagram bios to simply, “writer”, instead of marketing executive and blogger, yada, yada, yada… To be honest, I’m not just a blogger anymore, and my career focus on a long term basis isn’t about marketing or business, or blogging about it. I have learned so many lessons along the path of my so-far-failed career journey, and these lessons will help me along the way of writing and becoming a successful writer.

So why ‘writer’? Because that’s what I spend 90% of my day doing: writing. Whether it’s a short story, a blog post, a book, or a strategy, most of my time is spent writing, or researching on a topic I’m going to write. And it’s relieving to be able to just say “writer”, when someone asks me what I do. Will I accept contract work to write for brands? Probably not. I own what I write and these are my words, my brand.

Excuse #1: Never good enough

I never felt like I was good enough to call myself a proper blogger, far less a writer. I’d like to think that everyone thinks that they are a terrible writer, when they first start out; and on some level, that does make me feel less shitty about myself. I am pretty crappy writer when compared to the likes of Tolkien, Hemingway and Austin, but I believe that my style of writing is my own, and it is not in the same league, or even the same genres! I would never compare myself to the literary greats, even if by some minute shred of luck I become a best-selling author (although, you have to actually publish something for this to happen!).

So, suddenly my writing capabilities have morphed into something that’s a little more than average? No. I have simply grown as a writer, and will continue to. I spent some time looking back on some of my articles and blogs from about five years ago, and man… what a train wreck! From the venting, to the sloppy grammar; I really want to unpublish all of that work. And I did have it all unpublished for nearly a year, until I realised last week that I’d rather readers see my growth over time, rather than just what’s current.

To tackle this excuse, I just had to admit, and keep admitting, to myself that I’m not a J.K. Rowling, but I am a Désiré Roberts, and my skill will continue to grow. Five years from now, I’ll probably look back on this and think, “what a load of crap!”

Excuse #2: Never had the time

Busy is as busy does, and boy was I a busy bee! Honestly, I wasted a lot of time thinking about writing, and not actually writing. I reckon most of that came from not feeling like I was good enough, but, it also stemmed from my lack of routine and workflow. When I was working full time, back in 2013 and 2014, I seemed to find the time to write at least one thing a month, or maybe every two months, but the second I fell out of that routine in 2015, my productivity fell through the floor of my glass house.

As of the last month, I’ve spent a lot of time thinking and introspecting into what I really want to do with my life, and what I hope to achieve in the future, near and long term. Now that I have those goals in perspective, and I’m working full time again, I strangely have more time and focus to dedicate to writing and researching.

Finding your footing, grounding yourself, stabilising your finances and getting into a good routine (and sticking to it!) are all really necessary to leading a successful life, not just a career. But I can safely tell you, it’s far easier said than done, and takes a hell of a lot of sacrifice.

I’ve bought myself Scrivener, and have begun writing on the tube to and from work. It’s a great way to spend my time, and it’s a good 90 minutes of my day at the very least. So, gone is the excuse that I can’t write because I haven’t the time. I now have to make the time in order to publish something half decent every Monday.

Excuse #3: Not honest enough

Another issue I had was simple to identify, but not easy to rectify: I wasn’t being honest. I never lied about statistics or data. But I was lying to myself for a long time. I spent the better part of five years trying to decide if I wanted to write about my sexual abuse and its effect on me. It has taken me five years and just under 5000 miles of physical distance for me to finally make the decision to just write it.

Why was this such an issue? Because, even though I was writing about business and marketing, I felt like a fraud. I felt like my life was a lie, and to a great extent, it was. The most important part of my healing was for me to stand and say, ‘yes, I was abused as a teen’ but to also end it with, ‘I didn’t only survive, I thrived.’ I’m not broken as a result of my experiences, I’m far stronger for it. But in some really messed up way, no matter what I wrote about, that honesty was just struggling to break through, like a brewing volcano, waiting to explode. Everything I wrote that was personal was tainted, and for those who could read between the lines, they could tell something was not quite right.


Looking back, I’ve said on so many occasions that I’ve made the decision to write more often, and that I’ve re-worked the content strategy, and I was ready for a new chapter of my blog. All of it lasted for two weeks, max. I never stuck to any schedules and I never really wrote what I wanted to write, until now.

Today, my writing has a purpose and a responsibility, to connect with people on a very human and empathetic level, to guide them through their dark tunnels, and to help them thrive, too. Yes, there is a little bit of selfishness here; I hope to find some deeper healing with being honest. I hope that in writing what happened, and telling people that no matter what they will be okay, that I will be okay too. I’m not broken, but I still have wounds that need to be closed.

You don’t need to read it. But someone will.

Growing and Changing…

Growing and Changing…

As life flows around its obstacles, you grow and change; and I am no exception. This blog has seen so much change over the years and as I look back on the last five years, I see how much I have grown, changed and achieved. And I’m so very grateful for those experiences that molded me into the person I am right now, as I write this.

I haven’t had an easy life (and no one really has honestly) but the last year has been particularly hard on me. I’ve been good health-wise, but the obstacles I’ve had to face and the fears I’ve had to confront during 2016 are nearly unbelievable; recapping the year makes me wonder if it was even real or fiction.

On Hopes, Dreams, Loss, and Emotional Trauma

As with every new year, one looks forward to doing new things, making progress and achieving goals, whether or not they are realistic. My 2016 goals weren’t exactly unrealistic, but they relied heavily on other people pulling their weight and getting shit done on their end. Big mistake.

The lesson learned here is to be selfish and make goals for yourself. Being selfish does not make you a bad person. You need to put yourself first too, sometimes. You can’t help anyone if you’re not working at your best capacity, or if you’re unhappy (I learned this from a very special person). You will spend your life being unhappy but helping everyone else be happy and in the end, you’ll look back on your life and wonder what the hell you did, and wish that you made more selfish decisions sometimes. Look after yourself.

So, as you could imagine, my goal was not achieved, but that’s okay because life sometimes just does not work in the ways that we want it to. I do believe in a higher power that always wants the best of us. However, getting me off the path I was on, was a very painful process.

In early 2016, while struggling to build a sustainable business in an industry that’s respected globally, but not in Trinidad, the partnership went sour after my then significant other (and also one of the three co-founders), felt ‘strongly’ about the future of the business and our relationship, both of which subsequently descended in chaos within a week. To be fair, the relationship was already unstable whether or not he wants to admit it; we discussed a separation seriously at least half a dozen times since 2013. It wasn’t a simple separation, as it was fuelled with high levels of stress and emotion.

I learned a very powerful lesson that fateful night; choose your inner circle wisely. Never before had words been truer. Over the years, I watched my circle shrink and shrivel into nothingness, and I never put any real effort into making and keeping friends close. You are not an island; you really need people around you to keep you going and support you when things get tough.

As to what instigated such a dramatic breakup, I cannot put my finger on one thing because it was a build up of issues that we never honestly dealt with. But what I can say is that communication, and honest communication is so very important to any relationship. But as painful as that experience was, I did learn a lot from it, and the lessons from the relationship are there to help me grow and not continue to make the same mistakes; all of which I am grateful for.

I was not, however, prepared for what was up next.

We did an entire company restructure, restructured the service and tried to work more efficiently and effectively. And it worked for a while…

My good friend of ten or so years was also a co-founder of the business, and suffered a separation from his wife and kids at the hands of the business (and some personal stress); a mere two weeks after my breakup. So, it was chaos trying to deal with two breakups and a startup that was undergoing a severe shuffle (due to my breakup). Needless to say, we managed to make it out alive, just about!

During this chaos, I was sleeping about 3 hours a night on my mother’s couch in her tiny apartment while living out of the boot of my car. I spent my day managing the few clients we had, and cold calling to grow the business. Honestly, we needed money, because we had real bills to pay, with clients who weren’t paying consistently. I just kept hitting wall after wall.

Finally, I got a place to live. It wasn’t easy and I had no idea how I was affording it over the next year, but I had to try. Something was bound to work right? Wrong. After months of trying, struggle, pain and tears… I lost my first car. And then, as life would have it, I had to make the hard decision to give up my apartment instead of digging my debt hole deeper.

So at this point, I was in more debt than I could imagine, no home, no car, the business was struggling as a result of my personal situation and no one was hiring in my industry. There was only one thing left to do…

Tearing it all down to build all over again

In December, I made the decision to migrate back to England, my home country. This wasn’t a light decision as I knew that there was a high chance I was never returning to Trinidad, leaving everything I’ve known, family, friends, business and network all behind, to start over in a country I left when I was seven years old. But, 26 is as good an age as any to start all over.

I got my clean slate. Finally.

There is light in this story. And a story of love, too. Remember that friend I mentioned earlier? He’s the one good thing that happened all year, along with all the valuable lessons learned. As the stress grew and pressure increased, we got closer. I don’t have to go into details to tell you what happened here. But what I will say is that he’s the most incredible person I’ve ever known, and he continues to grow and overcome his obstacles with grace and patience. He’s a constant inspiration to me and the one who inspired me to write and be the best version of myself. Why this didn’t happen years ago, I don’t know, but you know what they say: nothing good comes easy. Side note: I’m deliberately not publishing details regarding this yet because I do enjoy some level of privacy, and wish to respect his too.

So I’m in England, writing this blog post on the tube home from work, and slowly rebuilding my life.

I’ve learned a very powerful lesson about leaving everything behind: when you tear everything down, you choose what you want to build in its place. Loss is not always a bad thing. When you’ve lost everything and you’re standing in the ashes of what once was, you realize how much space you now have to build something better, and you also know what’s truly important to you. Letting everything go has been the most liberating experience of my life, albeit the most painful.

Now back to this blog…

I’ve decided to start writing about my past experiences and hopefully someone will eventually learn from it. I no longer have Trinidad and the people in it holding me back. For those who know me personally, you know which experiences I’m talking about. For the rest of you, you’ll have to just stay tuned!

It’s your job to create value, not chase revenue.

It’s your job to create value, not chase revenue.

For most, starting a business is about making money. I mean, that’s the crux of it, but should it be your main focus?

We’ve seen time and time again, especially on a local scale, how businesses with a money-only focus either fizzle out or end up perceived as corrupt or greedy, and the consumers are the ones who suffer in the long run.

What if you can have your cake AND eat it too? What if you can create a business where people want to work at, and people want to shop from, and you can make a sustainable revenue on a long-term scale? Sounds too good to be true? While some may say it’s idealistic, I call bullshit.

You love when you get great customer service, right? I do, too. I remember those places, and recommend them frequently. So build your business on that touch point of value.

People don’t buy a product for what it is, they buy because of how they value it.

When you create something that’s worth something to someone, not only yourself, you’ll find that your consumers will become brand ambassadors, and those are the people who keep your business alive. Repeat business is the most valuable business in a sustainable long-term revenue model.

As entrepreneurs and business owners, it’s up to us to change the landscape in Trinidad in terms of value and customer service.

We always think that local items are of lower value and customer service is always crap, but what are we doing as business owners to change that? We have to add more value to our product bases and look at our offerings in a new light, putting a consumer first, not money first.

The money will come, it always does, but you have to be patient. You’ve got to run this one like a marathon, not a sprint. One of the issues here is that many small business owners are unaware of the struggles in the first two years, but I’ll get into that in another post.

Start by building something of value, something that people want, something that people will remember, with happy employees, a great company culture and fantastic customer service… You will outsell every single one of your competitors with this strategy.

When is it the right time?

When is the right time?

The right time to start a business?

The right time to start a family?

The right time to start a degree?

It’s never going to be the right time. The right time is NOW. You’ll never really know if you’re ready for that next step unless you actually take it.

So empower yourself to take that step… Now.

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