If you want a strong and diverse team, absolutely.

Several years ago while helping to grow a mid-stage VC-backed start-up, we had budget for only one additional full-time hire in a critical operating team. Experience dictated we needed at least three humans to cover all of the skills and background we wanted to add with just one hire, so we spent extra time crafting a very long and very detailed job description. We were specific about degrees required (undergrad and specific doctorate), years out of school (not too junior or too senior), start-up and public company experience (preferably with an IPO in the mix), substantive areas of mastery (drafting…


Identifying priorities in a SaaS company

This past weekend I spent some time with the cofounders of an early stage start up, looking over their draft vision and mission materials. As I was reviewing the summaries, I was struck with a perplexing hurdle, the identity of the customer wasn’t clear. Without a clear customer, it was difficult to settle on a vision or a mission statement. Building any product without a clear customer in mind is like designing a custom house for an unknown client; there is a lot of room for expensive errors and waste.

First, identify the core pillars.

We jumped on a call to talk this through. I…


About three years ago I decided to take a 30 day break from drinking. It was like dry January right after the holidays, but instead it was August, starting while at Burning Man.

My reasons were pretty specific. I was starting the scary process of separation — ultimately divorce — and knew I needed to be as crystal clear as possible. I couldn’t afford a fuzzy moment and didn’t want to look back on a single regrettable signature, text, conversation, or kiss.

I was scared and disoriented. My life was being turned upside down. In a way, a commitment to…


Photo by NASA on Unsplash

Dear Humanity,

I am sorry it had to come to this. Many of you are suffering during this global health crisis. Some of you will die. However, things had gotten a little out of hand. Please trust me: this was an absolute last resort.

While I have been impressed with your individual and collective intelligence and evident ambition, you all seem to have forgotten what really matters. In your races to advance, acquire, own, control, and indulge you have lost touch with some of the basics.

I have been sounding a range of alarms to alert you of the consequences…


“It’s not a faith in technology. It’s faith in people.”
- Steve Jobs

First, a bit of context. I have twenty years of experience working in NY/Silicon Valley-based media and tech companies, primarily as a lawyer. I coach emerging talent, advise founders and CEOs, invest in start-ups, and teach at UC Hastings. I have throughout all of this been part of several teams behind drafting and enforcing Terms of Use (including app/platform age restrictions) and privacy policies, many designed to protect minors.

I’m also a mom. In fact, that is my first (and most important) job. I have two sons…


“Whatever you do, don’t tell people you don’t drink. They’ll think you’re weird.”

Bhutan, April 2018

Last night I attended an international boarding school reunion at a lovely rooftop venue on Park Avenue in New York City. I was among approximately 75 people of many ages, diverse backgrounds, and exotic nationalities, our experiences at a Swiss boarding school at some point in the last seven decades being the thread that tied us all together. I attended the reunion alone and knew nobody.

It’s always interesting to experience these types of events as a non-drinker. Whether it is a professional networking happy hour, a…


Taken from VA Flight #1024 from SFO → JFK on 9/25/17

I am regularly asked “how do you do it?” It is usually a young professional considering having a family, or a parent trying to imagine adding an out-of-the-home full time job to his or her already demanding schedule. Men and women approach me about this topic weekly.

Until recently, I didn’t take this all that seriously. I’ve candidly shared that parenting and balancing personal/family life while advancing a career is challenging but worth it. …


My law school students encouraged me to publish this one: a few tips on how to inspire confidence in and ensure unintended habits don’t hold you back.

Do:

Maintain Eye Contact

Learn how to hold eye contact throughout an entire communication — both as the speaker and the listener. It can be uncomfortable, particularly during the speaking part, but this can be mastered with practice. What is more uncomfortable is trying to communicate with someone only to have them not believe you/trust you/want to continue working with/communicating with you because you seem all over the place or lacking conviction. Be confident…

Cecily Mak

reflections are my own. mom, investor, advisor, author. thrive in overlap between tech & human betterment. clearlife is my jam (ig @clearlife108); book in ‘22!

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