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My Failed Startup Almost Destroyed Me



If you know who Peter Thiel is, you probably also know what most people referred as Thiel’s law: “A startup messed up at its foundation cannot be fixed.”

That’s what happened to us. I wish I knew what I know now. Perhaps I should write another article about how we failed, if it’s useful for people.

I was under the impression I was supposed to sacrifice everything to make it work. I didn’t pay enough attention to my health and I let myself go. For me, the only important thing was my startup and nothing else.

The number of people I have encountered that think like I did is alarming. This is a warning for other entrepreneurs that might be going through the same, or if they think there would be time later to take care of themselves.

It Was Bad From Day 1

Since my co-founder and I decided to create Pathfinder, we were psyched and pumped by the infinite possibilities of what we could do and what we can achieve. We felt we had all the energy in the world, even if we didn’t have the experience or any idea or what the f**k we were doing.

That adrenaline you get when you’re building a startup made me push my limits. We knew it was a rough journey, and so I made it worse by forgetting to take care of my body, among other things you will read below.

You get caught up in that bootstrapping state of mind. You’re so pumped you don’t think or do anything else than your startup. You live, breathe and dream about it. No weekends, no time off, you just work 24/7.

Also when you’re bootstrapping, you cut your expenses as much as possible to save up money, dedicate every penny to your startup, or like in most cases, you’re giving up your regular sources of income.

You start going back to the cheap fast food diet you had during your first year of college. You think it’s okay, that your body can take it, and besides, it’s only for a few months.

I was eating a lot of crap for the sake of not spending time hopelessly trying to cook (I’m terrible at it). I found junk food convenient because it was an already-made hot meal I could get for cheap. My eating habits were and still are terrible.

It Got Worse With Time

It’s hard to break the cycle of eating poorly when you’re in a startup. I tried several times. The emotional roller coaster you go through as a founder could make you relapse in your down moments. When you’re in a startup, there are far more downs than ups.

I became abusive of bad food choices as if it was an addiction. In my many days of sorrow, I tried to make myself feel better with fast food. In my good days, I wanted to treat myself with something ‘delicious’. It ended up being a more expensive version of the same sh*t I was eating before.

I did nothing but work. My mantra was “eyes on the prize, eyes on the prize.” I was not exercising, not giving my mind some rest, not eating right, no sleep and never unplugging.

And I was always tired. Even when I took some time off I didn’t really rest. But I didn’t care. I just wanted my startup to take off, and then we can talk about everything else.

I had a few episodes of stomach pains so severely that there was a time I was hospitalized for a night. I was so stubborn and stupid, that wasn’t enough of a wake-up call to make changes.

Now I’m sure those habits made it harder to succeed. Not that my startup failed because of this, but I’m sure I could’ve been better at it if I was in a better shape.

Skipping Through Life

I let this toxic mind set control my life. It also deprived me of precious life moments and people I would never get back.

You tell yourself “don’t worry, keep going! Don’t lose focus on your dream! You’ll enjoy the rewards when you succeed.” You’re wrong. I learned this on the hardest way possible.

I am originally from a beautiful Caribbean island where the Dominican Republic is, but I live in Spain. Even though I love the old España, its people, and it’s the place I consider home since 2006, it really makes it complicated for immigrants to build companies here.

The struggle of being a startup founder is worse when you add the incredibly painful process of being an immigrant. But what it feels like to be a startup immigrant, the overcomplicated migration system here and the pain in Spain of being an entrepreneur are whole new subjects we can discuss in other articles.

Not only it’s been extremely hard for me to go through the Spanish migration process constantly, it seems like it never ends. In December 2012, I was not on top of it. I said to myself “It’s okay, I won’t be able to go home for Christmas, but I’ll fly there later, even for a more extensive period.”

Yes, I rationalized it in my head. Tickets were very expensive anyway, I could use that time to work on some things and I was permitted to renew my resident card later on anyway. I could do it later on and it’ll be fine. “Eyes on the prize, Rui, eyes on the prize.”

I WhatsApped my father telling him I was not going home, but not to worry, I’d be there in a few months to spend really quality time with the family. He then responded that he was very sad I wasn’t going to be there. By then, it had been more than a year since the last time we saw each other.

My father was diagnosed with cancer in 2007. In 2012 it seemed he finally won that long battle but then it came back a few months later. It never ocurred to me that it could’ve been fatal this time.

In January 2013, things got a turn for the worse. I tried to rush my papers to be able to fly home ASAP. Since it was during the holidays there was not much to be done to fix it.

And then it was too late. One evening my mom called me to tell me dad passed away. We thought he had a few months, I thought I had time.

I didn’t see him and I wasn’t there to say good-bye. I cheated myself out of more time with him thinking I could always do it later. Even if my startup would’ve succeeded, sacrificing that would’ve never been worth it.

Your Environment Affects You

After my father died and the excruciating guilt of not being there, I took my habit of abusing of fast food to a whole new level and gained even more weight.

I carried on with my startup and didn’t want to think about what was going on. And then, I got to spend some time in Silicon Valley and a few months in New York and that helped me get out of that mental funk.

It started when I flew to San Francisco for the Evernote Conference. It was a long journey and I arrived there pretty late at night. I took an Uber to the InterContinental Hotel, checked in and went directly to bed.

At 5AM, my eyes were already wide-open. In Spain the local time was 2PM so I couldn’t sleep any longer. I turned the TV on and wandered around my hotel room. I stood on a weight scale while I was checking my Instagram feed on my phone.

It was the first time in years I saw my weight in pounds instead of kilograms. It was 231 lbs. My first reaction was “this can’t be right.” I checked the scale, threw my phone to the bed, took out my pajamas and tried again: 230 lbs.

I googled how much it was in kilos and it was, in fact, the right number. I’ve been seeing it for months but never converted it to pounds because I preferred to stick with a measurement unit I didn’t quite understand.

I immediately put on my training clothes and went to the hotel’s gym to work out until the morning. I have finally received my wake up call.

After that, I spent a few months in New York, and over there it was easier to make smarter choices. There are better food options and when you’re tempted to eat junk, you see the calories right there on the menu. It forces you to think twice about it.

I was in a great environment. I fell in love with the startup NY community. I pushed General Assembly to let me use their coworking space. They did even though they were closing the service and were not accepting anybody new.

During that time I ended up losing 30 pounds. It was a combination of feeling good and productive, surrounding myself with great minds and being in a better headspace. I was happy.

written by Rui Delgado, Startup Entrepreneur and Startup Author at Medium. see more.

Callum Connects

Benjamin Kwan, Co-Founder of TravelClef



Making music to create a life for his family, Benjamin Kwan, started an online tuition portal and his music business grew from there.

What’s your story?
I am Benjamin and I’m the Co-Founder of TravelClef Group Pte Ltd, a travelling music school that conducts music classes in companies as well as team building with music programmes. We also run an online educational platform which matches private students to freelance music teachers. We also manufacture our own instruments. I started this company in 2011 when I was still a freshman at NUS, majoring in Mechanical Engineering.

I was born to a lower income family, my father drove a taxi and was the sole breadwinner to a family of 7. I have always dreamed of becoming rich so that I could lessen the burden placed on my father and give my family a good life.

After working really hard in my first semester at NUS, my results didn’t reflect the hard work and effort I put in. At the same time, I was left with just $42 in my bank account and it suddenly dawned on me that if I were to graduate with mediocre results, I would probably end up with a mediocre salary as well. I knew I had to do something to gain control of my future.

During that summer break, I read a book “Internet Riches” by Scott Fox and I knew that the only way I could ever start my own business with my last $42 would be to start an online business. That was how our online tuition portal started and after taking 4 days to learn Photoshop and website building on my own, I started the business.

What excites you most about your industry?
Music itself is a constant form of excitement to me as I have always been an avid lover of music. As one of the world’s first travelling music schools, we are always very eager and excited to find innovative ways to a very traditional business model of a music teaching.

What’s your connection to Asia?
I was born and raised in Singapore and I love the fact that despite our diversity in culture, there’s always a common language that we share, music.

Favourite city in Asia for business and why?
Hands down, SINGAPORE! Although we are currently in talks to expand to other regions within Asia, Singapore is the best place for business. I have had friends asking me if they should consider venturing into entrepreneurship in Singapore, my answer is always a big fat YES! There’s a low barrier of entry, and most importantly, the government is very supportive of entrepreneurship.

What’s the best piece of advice you ever received?
I have been blessed by many people and mentors who constantly give me great advice but right now, I would say the best piece of advice that I received would be from Dr Patrick Liew who said, “Work on the business, not in it.” This advice is constantly ringing in my head as I work towards scaling the business.

Who inspires you?
My dad. My dad has always been my inspiration in life, for the amount of sacrifices that he has made for the family and the love he has for us. He was the umbrella for all the storms that my family faced and we were always safe in his shelter. Although my dad passed away after a brief fight with colorectal cancer, the lessons that he imparted to me were very valuable as I build my own family and business.

What have you just learnt recently that blew you away?
You can not buy time, but you can spend money to save time! With this realisation, I was willing to allow myself to spend some money, in order to save more time. Like taking Grab/Uber to shuttle around instead of spending time travelling on public transport. While I spend more money on travelling, I save a lot more time! This doesn’t mean that I spend lavishly and extravagantly, I am still generally prudent with my money.

If you had your time again, what would you do differently?
I would have taken more time to spend with my family and especially my father. While it is important to focus our time to build our businesses, we should always try our best to allocate family time. Because as an entrepreneur, there is no such thing as “after I finish my work,” because our work is never finished. If our work finishes, the business is also finished. But our time with our family is always limited and no matter how much money and how many successes we achieve, we can never use it to trade back the time we have with our family.

How do you unwind?
I am a very simple man. I enjoy TV time with my wife and a simple dinner with my family and friends.

Favourite Asian destination for relaxation? Why?
Batam, it’s close to Singapore and there’s really nothing much to do except for massages and a relaxing resort life. If I travel to other countries for shopping or sightseeing, I am constantly thinking of business and how I can possibly expand to the country I am visiting. But while relaxing at the beach or at a massage, I tend to allow myself to drift into emptiness and just clear my mind of any thoughts.

Everyone in business should read this book:
Work The System, by Sam Carpenter. This book teaches entrepreneurs the importance of creating systems and how to leverage on systems to improve productivity and create more time.

Shameless plug for your business:
If you are looking for a team building programme that your colleagues will enjoy and your bosses will be happy with, you have to consider our programmes at TravelClef! While our programmes are guaranteed fun and engaging, it is also equipped with many team building deliverables and organizational skills.

How can people connect with you?
My email is [email protected] and I am very active on Facebook as well!

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
Download free copies of his books here:

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Before you enter a Startup or before you choose your founding team or new hires read, “Entering Startupland” by Jeff Bussgang



Before you enter a Startup or before you choose your founding team or new hires read “Entering Startupland” by Jeff Bussgang.

Jeff knows how to spot and groom good culture, as the book session was held in Zestfinance a company he invested in and now, “The Best Workplaces for Women” and for “The Best Workplaces for Tech”, by Fortune.

These are the questions during the Book Launch.

How to know if a hire including the founder is Startup material?
Jeff says to watch for these qualities.

First, do the hires think like an owner?
Second, do the hires test the limits, to see how things can it be done better?
Are they problem solvers and are biased toward action?
Do they like managing uncertainty and being comfortable with uncertainty? And comfortable with rapid decision-making?
Are they comfortable with flexible enough to take in a series of undefined roles and task?

How do we know if we are simply too corporate to be startup?

Corporate mindsets more interested in going deep into a particular functional area? These corporate beings are more comfortable with clear and distinct lines of responsibility, control, and communication? They are more hesitant or unable to put in the extra effort because “it’s not my job”.

If you do still want to enter a startup despite the very small gains at the onset, Jeff offers a few key considerations on how to pick a right one.

He suggests you pick a city as each city has a different ecosystems stakeholders and funding sources and market strengths. You have to invest in the ecosystem and this is your due diligence. Understand it so you can find the best match when it arises.
Next, to pick a domain, research and solidify your understanding with every informational interview and discussion you begin. Then, pick a stage you are willing to enter at. They are usually 1)in the Jungle, 2) the Dirt Road or 3) the Highway. The Jungle has 1-50 staff and no clear path with distractions everywhere and very tough conditions. The Dirt Road gets clearer but is definitely bumpy and windy. Well the Highway speaks for itself, doesn’t it?

Finally Please – Pick a winner!

Ask people on the inside – the Venture Capitalists, the lawyers, the recruiters and evaluate the team quality like any venture capitalists would. Would you want to work for the team again and again? And is the startup working in a massive market? Is there a clear recurring business model?

After you have picked a winning team and product, how would you get in through the door?

You need to know that warm introductions have to be done. That’s the way to get their attention. Startups value relationships and people as they need social capital to grow. If you have little experience or seemingly irrelevant experience, go bearing a gift. Jeff shared a story of a young ambitious and bright candidate with no tech experience who went and did a thorough customer survey of the users of the startup she intended to work with. She came with point-of-view and presented her findings, and they found in her, what they needed at that stage. She became their Director of Growth. Go in with the philosophy of adding value-add you can get any job you want.

And as any true advisor would do, Jeff did not mince his words, when he reminded the audience that, “If you can’t get introduced you may not be resourceful enough to be in startup.”

Startupland is not a Traditional Career or Learning Cycles

Remember to see your career stage as a runs of 5 years, 8 or 10 – it is not a life long career. In Startup land consider each startup as a single career for you.

Douglas Merrill, founder of Zestfinance added from his hard-earned experience that retention is a challenge. Startup Leaders to keep your people, do help them with the quick learning cycles. Essentially from Jungle to Dirt road, the transition can be rapid and so each communication model that starts and exists, gets changed quickly. Every twelve months, the communication model will have no choice but to break down and you have to reinvent the communication model. Be ready as a founder and be ready as a member of the startup.

Another suggestion was to have no titles for first two years. So that everyone was hands-on and also able to move as one entity.

Effective Startupland Leaders paint a Vision of the Future yet unseen.

What I really enjoyed and resonated with as a coach and psychologist was how Douglas at the 10th hire thought very carefully what he was promising each of his new team member. He was reminded that startups die at their 10th and their 100th hires. He took some mindful down time and reflected. He then wrote a story for each person in his own team and literally wrote out what the company would look like and their individual part in it. In He writing each of the team members’ stories into his vision and giving each person this story, it was a powerful communication piece. He definitely increased the touch points and communication here is the effective startup’s leverage.

Douglas and Jeff both suggested transparency from the onset.

If you think like an owner and if you think of your founding team as problem solvers. Then getting transparent about financials with your team is probably a good idea. As a member of a startup, you should insist on knowing these things
Such skills and domain knowledge will be valuable. There is now historical evidence of people leaving startups and being a successful founder themselves because they were in the financial trenches in their initial startup. Think Paypal and Facebook Mafia.

What drives people to enter a startup?

The whole nature of work is changing. Many are ready to pay to learn. Daniel Pink’s book Drive showed how people are motivated by certain qualities like Mastery, Autonomy and Where your work fits into big picture. Startups do that naturally. There is a huge amount of passion and the quality of team today and as it grows then the quality of company changes.

The Progress principle is in place, why people love their startup jobs is not money rather are my contributions being valued? Do I see a path of progress and do I have autonomy over work and am I treated well?

Find out more about StartupLand on Amazon

And learn from Zestfinance

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