50 Shades of Grey (and Orange) Accelerating my journey of self-renewal with a dash of grey and orange.

I turned 34 four days ago, not long after my daughter turned 2 and a little ahead of my son who will soon be 4. Singapore turned 50 two days ago – its SG50, its Golden Jubilee – amidst much fanfare and against the backdrop of an increase in social spending and impending general elections. It’s been almost 6 years since I left service and embarked on the wildest ride of my life as an entrepreneur and investor. Guess what? That life is going to get even wilder from here on.

This is not a post about BDSM in orange-colored hosiery. Hold your horses, bear with me for a bit and my apologies if you were expecting something raunchier ;-).

I really should have written this post 2 months ago, but felt I could only do this post justice once I’ve had more time to let things soak in a bit more. If you’ve been reading my recent articles, you’ll know I’ve been in a pensive mood for much of 2015. I mused about my need to belong for much of the first half of this year before realizing that I had inadvertently built my own prison and served as my own jailkeeper with my previous train of thought. A sequence of events transpired to accelerate my realization, culminating in a series of decisions I made.

I pulled out of Myanmar after having spent 45 days in 2014 in Yangon; Silicon Straits relinquished majority equity stake in our Myanmar subsidiary to the amazing team of Kaung Sitt, Aung Kham and Sandi Thein, which has now been renamed to Digital Kaway. I was involved in its restructuring and business repositioning. Silicon Straits continues to hold a meaningful minority stake while I remain as an advisor to the team. It was a frontier market that showed great promise but ultimately needed more time and attention than I could afford. I also didn’t think I knew the market enough parachuting in from time to time and preferred to continue my Myanmar journey vicariously through the trio.

I convinced Jonas Eichhorst to join the Silicon Straits tribe and take over my day-to-day responsibilities at Silicon Straits and re-designated myself as Executive Chairman. I was only spending between 10% to 20% of my time getting actual work done anyway, and felt it was time for me to focus on our meta-game and leave the macro- and micro-level execution to the excellent management team (Jonas, Kent, Andy and Sandra) that is in place at the Silicon Straits group. We booked a substantial one-time investment-related transaction that saw the company recover almost all of Silicon Straits’ seed round I had raised in 2013, which will be reinvested for our expansion into Indonesia. I had overseen the company’s founding in Singapore and steered our entry and expansion into Vietnam (more so), Myanmar (less so) and the early bits of our Indonesia strategy. I didn’t want the group to be all about me and my vision and felt it was time to let the team shape more of our collective destiny. I embark on my new role as Executive Chairman confident of the playbook we have devised and with the group’s mission statement to be clearer than ever – building products, companies, fostering communities and making seed investments.

I remain as a board member of E14 fund and Burpple, and also joined the board of a Singapore-based startup as part of an investment in their recent seed round; I can’t share more since the company has yet to release the news on its funding, but I look forward to advising the founders on their market expansion and Series A strategy. I also made a small investment in a US$1+ million seed round of a Hong Kong-based e-commerce startup co-founded by a Carnegie Mellon peer of mine. The US$5 million Neoteny Labs (“Neoteny 2”) fund that I started with Joi did not have any new liquidity events, but we did return over US$6.7M to LPs and ourselves, with a further US$12+ million in unrealized portfolio value. One of our fund investments, littleBits also recently announced their US$44.2 million Series C funding led by DFJ Growth, which is pretty awesome. I’m hoping for no more than US$1 million in write-offs and a further 2X to 4X gain on the remaining unrealized investment portfolio over the next 3 to 5 years. Joi recently raised his 3rd fund in Neoteny 3, of which Silicon Straits also became an investor to; Neoteny 3 won’t be leading any investments unlike Neoteny 2.


I want to pause for a bit and turn your attention on a great speech by the now-deceased John Gardner that was shared with me by my friend Jia Chuan that I’ve read and re-read many times over this past long holiday weekend. It struck all the right chords in me and served as my bible for self renewal as I finally take up the challenge to join GreyOrange as Vice President (International) on 1 June 2015 – a company that I’ve been advising since October 2013.

You come to understand that most people are neither for you nor against you, they are thinking about themselves. You learn that no matter how hard you try to please, some people in this world are not going to love you, a lesson that is at first troubling and then really quite relaxing.

Life reminder 1: The above segment from John’s speech reminds me not to try to please everyone even as I remain true to myself without unnecessarily being blunt and abrasive. I have on occasions been overly blunt in my interactions with people in the name of truthfulness; more tact and awareness wouldn’t hurt, even as I try to spend more of my life around people who react positively to my sincerity and don’t misjudge my intentions.

You come to terms with yourself. You finally grasp what S. N. Behrman meant when he said “At the end of every road you meet yourself.” You may not get rid of all of your hang-ups, but you learn to control them to the point that you can function productively and not hurt others.

Life reminder 2: I am not and can never be perfect, and I certainly don’t need my imperfections to stir ripples in my wake, no matter how effective I may be. I also don’t need to try to be someone I think people want me to become, and have more faith in the better bits of me while restraining the poorer bits of me.

You learn the arts of mutual dependence, meeting the needs of loved ones and letting yourself need them. You can even be unaffected — a quality that often takes years to acquire. You can achieve the simplicity that lies beyond sophistication.

Life reminder 3: Sweet surrender; be it as an entrepreneur working in a team or in a marriage with my better half who can also bring out the worst in me. The zen of making things work without pining for a better deck of cards is what maketh a man.

One of the enemies of sound, lifelong motivation is a rather childish conception we have of the kind of concrete, describable goal toward which all of our efforts drive us. We want to believe that there is a point at which we can feel that we have arrived. We want a scoring system that tells us when we’ve piled up enough points to count ourselves successful. So you scramble and sweat and climb to reach what you thought was the goal. When you get to the top you stand up and look around and chances are you feel a little empty. Maybe more than a little empty. You wonder whether you climbed the wrong mountain. But life isn’t a mountain that has a summit, Nor is it — as some suppose — a riddle that has an answer. Nor a game that has a final score.

Life reminder 4: Enjoy the journey and not the outcome, for ambition != motivation.

Keep a sense of curiosity. Discover new things. Care. Risk failure. Reach out.

Life reminder 5: Things always come full circle at the start of every new beginning. Neoteny FTW!


It’s one thing to have started and run a seed-stage venture fund, and another thing to try and scale a company past 200 employees and beyond and open new markets while you’re at it. Since October 2013, I’ve seen GreyOrange grow from 20 to over 200 pax and undergo 2 funding rounds. I think we’re now ready for international expansion which is where I can best apply myself and my abilities. I am delighted to be part of Samay and Akash’s management team at GreyOrange and look forward to applying these John Gardner-inspired life reminders as I work with our fast-growing team to expand into China, Japan, Indonesia and other parts of Asia Pacific.

Me posing with our Butlers

The next big leap is here.

NB 1: The “Grey” in GreyOrange refers to experience and brain cells, while the “Orange” refers to youthfulness, spunk, and creativity.

NB 2: We just announced US$30 million in Series B led by Tiger Global. It’s an incredible achievement given that Series A was only slightly over a year ago; kudos to Samay, Akash and the rest of the GreyOrange team for the ongoing client and investor validation.

NB 3: I’m actively hiring to add to our Singapore, Hong Kong, China, and Japan efforts. Please drop me a note if you’re into robotics or any multi-disciplinary combination of engineering disciplines, field engineering and warehouse design and supply chain optimisation.

About James Chan

James Chan is an entrepreneur, investor, geek, photographer and husband/father based out of Singapore. Apart from frequent travels to Vietnam, Myanmar and Indonesia for work, James can also be found online via his trusty 15" Retina MacBook Pro or iPhone 6+.