People have different style preferences. So much of what makes advice good is the right style.


So I randomly came up with this system last night (applicable to any advice that is given or received in any kind of relationship, not specifically formal advisor/advisee relationships) to be good at advice

Different levels of advice

  • Level 0 — words of encouragement and acknowledgement: You don’t actually give advice.
  • Level 1 — anecdotes and sanity checks: You don’t actually give advice and mainly listen. Your advice is implied with your anecdotes and the questions you ask.
  • Level 2 — tactical and strategic: You diagnose the immediate situation and give direct advice without value judgments.
  • Level 3 — philosophical and principles: You diagnose the false belief underlying the question and guide them to view the situation through a different lens. …

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  • Guidance to shut down all non-essential services; business owners have right to defy
  • Employees have right to work from home; protected from retaliation
  • Retail, restaurant, other in-person workers have right to leave of absence; can collect PUA (Pandemic Unemployment Assistance — $600 per week allocated for those unemployed due to Covid in addition to regular unemployment benefits; part of the CARES Act).

The way I see it, net we would have ended up in the same place:

  • Hosting a social gathering became taboo among my peers not because of breaking the law, but because of some mix of wanting to stop the spread and wanting to be seen as a morally upright citizen. …

This is the part 2 following 33 Books I’ve Read and Reread in the Past 3 Years from March 2018 (2 years ago). I love to read and here are a few select picks from the past couple years. I drafted this article, didn’t finish it, and forgot about it for a couple months so I’m opting to hit publish because I want to get it out of my drafts folder and into the world, so please excuse the typos:

Books worth reading more than once:

Never Split The Difference by Chris Voss: As someone who was slow in youth to pick up on the emotional nuance of persuasion and how to communicate effectively, this has been incredibly helpful. For those not naturally gifted with EQ, this book is for you. …

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Building Products That Help People be Their Aspirational Selves Without Going Bankrupt

It’s hard to succeed with a product that only makes money if people behave as their aspirational selves. Your churn is too high.


  • Gym memberships
  • Goal setting apps
  • Meditation apps

If you want to make money on these you have to get paid upfront or on a lock-in subscription with a low enough price that the user thinks “I won’t cancel because the sunk cost will make me engage” and doesn’t feel bad about how much money they’re wasting if they don’t.

What you cannot do, however, is make an “aspirational self” product that makes money on the basis of user performance/engagement. …

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I remember sitting in on a meeting with an angel investor who decided to pass on the deal and asking why. Investor: “She wasn’t likable enough.” Me: “Oh yea, what did she do?” Investor: “You heard the way she was talking to me.” Me: “Yea… she was quite direct I guess. But was there something that didn’t match with the dd you reviewed up until this point?” Investor: “I just didn’t like her attitude. She was arrogant.”

This entrepreneur was not arrogant. She was brief, direct, and confident about the future prospects of her company. …

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I went back and forth for a long time whether people are black and white or many shades of grey; whether morality is relative or absolute. To make sense of a worldview based on a framework of moral relativism I had to do all sorts of mental gymnastics and the end result was that I couldn’t see people with harmful intent staring me in the face. When it came to this area of life, I was dumb. I experienced what it was like to have a bad person win to re-examine my views. At first, I fretted that maybe this person just didn’t understand my culture (mistakenly thinking perhaps it was a question of relative morals). I questioned that maybe we had a miscommunication. I thought maybe I just didn’t understand them. I finally distanced myself and had time to reflect and see that no, the person just had harmful intentions towards me. …

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I love to read. There’s richness and complexity in the concepts you absorb through reading that you can’t get from listening to talks or having someone explain something to you. My reading list skews towards the philosophical, historical, sciences, startups and venture capital. This isn’t an exhaustive list, but excluding the venture capital books which would be too specific, I think the books on this list can be interesting to most anyone who is interested in understanding how the world works and how to function better in it.

Books worth reading more than once:

Sapiens: A Brief History of Humankind by Yuval Noah Hariri: What a brilliant, honest account of the world we live in. Armchair philosophers love to criticize this book as suited only to armchair philosophers but he pushes no agenda but truly informs and I loved reading it. It is not through an Eastern lens, a Western lens, an Israeli lens, an Arab lens, or any other lens, just reason by someone who sees outside their own prejudice and is willing to go against convention. My only disappointment is he came up with no logical answer as to why the subjugation of women has been so ubiquitous across the cultures and eras, despite his ability to come up with true answers to many other anthropological/sociological questions that have stumped entire departments/the news media. Throughout the book I went “that makes sense!” on his theses that directly conflict with popular consensus. …

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When you think of Silicon Valley what do you think of? Maybe you think of Elon Musk going to space or Peter Thiel searching for immortality. Maybe you think of scrappy entrepreneurs using breakthrough technologies to change the world. In Silicon Valley, entrepreneurs benefit from networks that provide insider information, venture capital, human capital, mentorship, and support resources galore. It has a sprinkling of hippie counterculture in there to encourage outside-the-box thinking.

Now what do you think of when you think of an emerging startup ecosystem, such as the one in Dubai? What is Dubai’s brand as a startup ecosystem? What kind of startups come out of here? …

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Successful venture capital in fragmented, emerging markets differs from the developed world.

Since WOMENA’s launch a year and a half ago I have seen over eight hundred pitch decks, listened to over a hundred live pitches, conducted due diligence on about thirty startups, and finally overseen investment in four startups. My investment thesis has changed and the startups I do due diligence on are different. For one, I now outright reject startups that solve first world problems but target emerging market customers.

When I first arrived, I evaluated “first world startups” with the same framework as I evaluated them with back home. If a startup solves a real problem and it is in a large, untapped, and growing market, why wouldn’t it be of interest to me? Let’s say said startup provides a similar solution that has already been successfully implemented, scaled, and acquired in the US. Of course I would want to take a closer look. …

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Both optimistic and delusional people see how things could be better

Delusional and optimistic people. Sure, both appear to have a positive attitude. Both talk about changing the world. Both are confident, and often charismatic. But there are big differences, and they are important.

Delusion ruins optimism for everyone. Delusional people mislead people, wasting time, money, and energy along the way. They leave behind chaos, and society responds by telling the optimist to be more cautious, more risk averse, more fearful. Optimists are told we’re “playing a fool’s game,” and optimism gets mislabeled as hubris and elitist arrogance.

A large chunk of my work sourcing deals for WOMENA, investing in startups, and doing due diligence, is parsing out optimism from delusion, and I’ve become good at it. I’ve learned that the key to identifying whether I’m looking at an optimistic person or a delusional person can be broken down to 1) roadmaps or lack thereof, and 2) the pursuit of immediate gratification versus an end goal, and 3) the drive to action versus the drive to feed the ego. …


Chantalle Dumonceaux

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