Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Calvin Sun, Founder and CEO of The Monsoon Diaries, located in New York, NY, USA.

What's your business, and who are your customers?

Our unique style of international travel brings the solo travel experience to a group; in other words: "group travel for people who hate group travel." You no longer have to choose between a normal life and a life of travel: You can do both. We're a community of students and regular folks with full-time jobs who have visited 190 countries in 10 years without skipping class, quitting jobs, missing shifts, or breaking budgets. We find ways around the excuse of "I don't have time or money" and make it work. We come home with too many stories to share, fill ourselves with setsunai, saudade, and maktoub, and then we do it again. We don't take a vacation, we monsoon.

Tell us about yourself

When my father died of a sudden heart attack and my mom was diagnosed with Parkinson's Disease in 2006, I was left with hundreds of thousands of dollars of student debt with no job or any foreseeable sustainable source of income. It seemed I was destined to be confined to the shackles of my birthplace, and being that it was NYC, I reasoned I would be OK with that. Travel was never on the radar.

For the next few years, I was getting by with a few odd jobs and a handful of bartending gigs. Then in the winter of 2010, I jokingly made a bet with two friends that I would join them on their last-minute trip to Egypt on the condition that roundtrip tickets would be less than $800. I was not serious at all: Flight prices were nearly triple that amount! But then I checked the prices on a whim a few hours later: $650 roundtrip. Damn. The reasoning was I would rather be a man of my word and $650 poorer than someone who flakes on their promises (plus it was a great last-minute deal, and how could I look away from that?); within less than 48 hours, I woke up at 3 am in an uncomfortable bed to an unfamiliar ceiling in Cairo.

What soon ensued afterward was a continuing series of comedy of errors that compelled the very same friends who I made a bet with to leave Egypt earlier than expected. I ended up traveling solo without having planned to be alone. Although rough in the beginning, by the end, I couldn't imagine having traveled any other way. I soon quit all my jobs and left for another three months, beginning in the Philippines and snaking my way to end in southern India. I also started a travel blog called The Monsoon Diaries to document my daily progress.

There were no lofty ambitions, no plans to "make it a business," no expectations of "being an entrepreneur." I've remained this hopelessly oblivious Forrest Gump now with this lovely crowd running next to me, and when asked over and over why I move or "how I did it," all I can answer is with the exact genuine answer that Forrest Gump gave: "I just felt like running. "

As more people who were reading my blog asked to join my trips, I couldn't deny them the opportunity. On my trips, they began calling themselves monsooners, even running into other self-ascribed monsooners around the globe on trips of their own. Serendipities and synchronicities were happening worldwide. A community emerged. More people started to ask if they could join and who I was to deny them the opportunity.

Even when it seemed obvious that taking time and money off to travel would jeopardize the stability of our lives back home (let alone our professional futures!), we continued to encourage one another to believe in the magic of travel. Whether it was just for a single day in Ireland, a three-month epic from Turkey to North Korea, or just the magical eternity moment of complete strangers falling for each other, travel became an investment in our lives instead, not an interruption.

What's your biggest accomplishment as a business owner?

I was a full-time first-year medical student when I started The Monsoon Diaries and still was able to graduate on time after four years of medical school and four years of residency training in Emergency Medicine, becoming a full-fledged Emergency Medicine attending physician by 2018. My experiences then and since are now being turned into a book being published by HarperCollins (September 27 release), which title the publisher chose to be named after the blog itself!

And even as The Monsoon Diaries has grown so much over the past 12 years, I continue to travel and organize my trips in the same spirit and with the same style as I have and had done when I first started traveling solo back in 2010.

What's one of the hardest things that come with being a business owner?

Maintaining your authenticity and not letting the desire for profit get in the way of what should be your main focus of building something that is meaningful, fulfilling, and can help other people.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

It depends on the industry and the type of startup! Specifically for the travel space:

  1. Know yourself first before you jump into anything. For example, with travel, perhaps go on a few solo trips on your own and see if you truly can be your own best friend in a space where you don't know anyone in a 1000-mile radius, don't speak the language, can't read any of the signages or what's on TV, and nobody knows you in a 1000 mile radius. If you can't take care of or be comfortable with yourself even in the loneliest of settings, you're not in an ideal position where you can take care of anyone else, let alone a startup —whether it's being amongst or even leading a group of strangers in a foreign land away from home, the latter of which may feel even lonelier and more challenging.
  2. Travel authentically. Channel and even celebrate your inner Forrest Gump that's jogging around the country -- doing it because you "just felt like running." — then maybe that's a sign you're jogging in the right direction.
  3. The irony I learned with The Monsoon Diaries is to never do it for the money. The less you look to make a profit and recognize true value from within when you travel, genuinely, the more the right people will seek you. And perhaps in the grand irony of life, the powers that be may reward you for that authenticity.

Is there anything else you'd like to share?

My experiences (including when traveling stopped during the pandemic) are being turned into a book published by HarperCollins, with a September 27 release. If you would like more insight on the experiences that led The Monsoon Diaries from a travel blog into whatever it is today, please order or buy a copy from anywhere that sells books! Amazon Link.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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