For entrepreneurs, too often the holidays are anything but happy

For entrepreneurs, too often the holidays are anything but happy

ON NOVEMBER 27, 2013

For most people the holidays are about family, escaping work, overindulging on food and drink, and overall checking out. Those with jobs as teachers, bankers, and mechanics put their work lives on hold for a few hours or days. But for entrepreneurs, that’s not possible. Depending on where they are along their entrepreneurial journey, this time of year can be any combination of suffocating, exhausting, or jubilant.For the lucky entrepreneur, who has found some measure of success, the holidays become a personal victory lap where friends and family tell her how smart she is, how proud they are of her, and how they always knew that she would do something great. These are the good times. This is what we all strive for.

But that’s not how it goes for most entrepreneurs.

For the wantrepreneur or the still-toiling-away-at-the-drawing-board entrepreneur, time with family typically amounts to justifying her life and career choices, explaining the genius behind her billion dollar idea, and generally avoiding questions about “getting a real job.” These are stubborn times.

For the entrepreneur who has found that breakout idea, the holidays turn into a never-ending pitchfest for that oh so important friends and family (and fools) round of funding. Everyone with two nickels to rub together becomes a potential investor, and everyone who was once a mid-level executive becomes a potential advisory board member. These are optimistic times.

For the entrepreneur who raised that friends and family round in years past, the holidays are akin to a board meeting, “Groundhog Day”-style. Every family member who wrote a check needs an update. If things are going well, this is a labor of love. Our founder shares details on her current product roadmap, recent business development wins, new hires, fundraising status and valuations, and all the wonderful things the press has had to say about her company since the last update. These are hype-filled times.

And when things are not going well, this never-ending board meeting becomes death by a thousand paper cuts. Every “investor” (read aunt, uncle, grandfather, neighbor, t-ball coach, and mailman) who backed the company – most who presumably haven’t seen the entrepreneur in months, if not years – wants “an update.” What they really want to know is “What did you do with my thousands of dollars and how ‘gone’ is it, really?” Often, this will be the first time most of these investors hear the naked truth, or more accurately, see the painful reality of that truth in the entrepreneur’s eyes. These are crushing times.

Finally, for many entrepreneurs, the holidays are a lot like every other day. Rather than consisting of some long pilgrimage home and time spent with loved ones, the holidays are spent toiling away, probably in front of a computer screen, hoping to make a dent in the mounting list of to-dos, but surely nowhere near a fireplace, a turkey dinner, or any eggnog. These are lonely times.

There’s a reason investors and fellow entrepreneurs ask those starting out in this game whether they’re ready and willing to dedicate several years of their life to the all-consuming pursuit of a startup dream. It is the most relentless and unforgiving of quests.

So if you have an entrepreneur in your life, remind them this year to put work away this holiday season. And if you were part of a friends and family round, maybe leave that fact at the door, at least until your entrepreneur has gotten a few glasses of eggnog under their belt.

If you are an entrepreneur yourself, remember why you got into this game in the first place. Rediscover a bit of that sense of excitement and possibility from a time when failure seemed impossible.

And most importantly, put family before company. The hustling, disrupting, and non-stop selling can wait, at least for a little while.

About bambooinnovator
Kee Koon Boon (“KB”) is the co-founder and director of HERO Investment Management which provides specialized fund management and investment advisory services to the ARCHEA Asia HERO Innovators Fund (, the only Asian SMID-cap tech-focused fund in the industry. KB is an internationally featured investor rooted in the principles of value investing for over a decade as a fund manager and analyst in the Asian capital markets who started his career at a boutique hedge fund in Singapore where he was with the firm since 2002 and was also part of the core investment committee in significantly outperforming the index in the 10-year-plus-old flagship Asian fund. He was also the portfolio manager for Asia-Pacific equities at Korea’s largest mutual fund company. Prior to setting up the H.E.R.O. Innovators Fund, KB was the Chief Investment Officer & CEO of a Singapore Registered Fund Management Company (RFMC) where he is responsible for listed Asian equity investments. KB had taught accounting at the Singapore Management University (SMU) as a faculty member and also pioneered the 15-week course on Accounting Fraud in Asia as an official module at SMU. KB remains grateful and honored to be invited by Singapore’s financial regulator Monetary Authority of Singapore (MAS) to present to their top management team about implementing a world’s first fact-based forward-looking fraud detection framework to bring about benefits for the capital markets in Singapore and for the public and investment community. KB also served the community in sharing his insights in writing articles about value investing and corporate governance in the media that include Business Times, Straits Times, Jakarta Post, Manual of Ideas, Investopedia, TedXWallStreet. He had also presented in top investment, banking and finance conferences in America, Italy, Sydney, Cape Town, HK, China. He has trained CEOs, entrepreneurs, CFOs, management executives in business strategy & business model innovation in Singapore, HK and China.

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