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Hi there,

It has been overcast and rainy here. One might imagine that would put me in a dour mood. Instead, it's a festive fall season. I got pumpkins! 

Today's Contents:

  • Weekly Song: Om Mani Padme Hum
  • Why VCs Say No
  • Good Reads
  • Om Mani Padme Hum - In Memory of Stephen Smith

Weekly Song: Om Mani Padme Hum

Is it a song? Or a mantra? What's the difference, anyway? Om Mani Padme Hum is the most ubiquitous mantra in Tibetan Buddhism. Those Sanskrit symbols etched into rocks, painted into hills, or written on prayer flags?  It's Om Mani Padme Hum. I particularly like this version of the recorded mantra.

What does it mean? Loosely translated something like: May all beings live in peace. I bring up this mantra this week for two reasons.


First, this time last year, I was hiking the Annapurna Trail in Nepal on a trip with a friend and his closest friends and family. It was billed as a 'spiritual, one-in-a-lifetime, awe-inspiring trek'. Om Mani Padme Hum was everywhere. It was wonderful, but also challenging and difficult. Most of all because one member of our group did not make it to the end. I'll discuss that later.

Second, this time this year seems to an incredibly stressful time for many people, particularly in the US. Everywhere there seem to be groups of people taking the election week off, struggling to communicate with family and friends, or taking a break from social media.  Om Mani Padme Hum is there for you. Stable. Serene. Ancient.

Om Mani Padme Hum by Veet Vichara & Premanjali

Om Mani Padme Hum. 
Om Mani Padme Hum. 
Om Mani Padme Hum. 
Om Mani Padme Hum. 
Om Mani Padme Hum. 
Om Mani Padme Hum. 

You get the idea. 

May All Beings Live in Peace: Why VCs Say No.


I love reading friends newsletters as much as most people love scrolling through Instagram. This week, I especially enjoyed a conversation my friend Jonathan Friedman discussed in his LionBird Bites newsletter. Lionbird is a healthcare VC out of Israel. The topic that Jonathan was covering was 'Why do VCs say no and how to say no'. 

He starts quoting a new micro VC in a podcast. The investor (not Jonathan) says:

Frankly, the #1 reason I pass is that I am just not impressed by the founders. How can you say that? How can you tell someone to their face “sorry the reason I didn’t want to invest in you was because of you”...The incentives just aren’t there for a VC to say “Look, you’re just not impressive enough.” 

Jonathan reflects that:

At the surface, you’d assume it’s almost always an issue with the team, but having done this exercise myself it turns out that ~40% of my no's are to “VC fundable” teams (VC fundable = we would fund them if they were pursuing another idea).

For those interested, "this exercise" is explored in the Google doc of why Jonathan passed. 

My view: saying  'Not VC fundable' is much better than saying "you're not impressive enough". Impressive carries a judgment of worth, while 'VC fundable' is more analytical, potentially on the business model, or a hole in the team or story. You might also be saying, simply put, "not for my VC."

I also think that often the 'no' comes because it's a company that's not backable at that moment for that portfolio.  The fund might be in an odd place in its life cycle; they might have a competitive company; or they might just be distracted by another deal.

One of the potential advantages of the new era of micro-funds and solo-capitalists is the ability to underwrite for many different risk portfolios. Anyone who has crossed my inbox that has pitched an investment has been impressive to me. It is impressive to take a risk. To ask someone else to back you. But not every investment opportunity will be backable by any one particular pool of capital. 

Sensible Investing: Good Reads


Momentum Investment strategy: A Primer. What is momentum? Momentum refers to the tendency of assets that have outperformed the market in the recent past to continue outperforming in the future. In fact, momentum has been the subject of much research and discussion in the financial industry and in some cases has been shown to have the potential to generate excess returns in individual equity markets, foreign equity markets, country equity indices, global interest rate markets, and in commodities

The End of Insurance. Good read on the analytical premise of traditional insurance models - risk-pooling and law of big numbers - and that of tech-startups using "AI-enabled big data" to measure risk more precisely for the individual. Relevant for the upcoming public offering of Root auto insurance. 

Model Performing Monitoring Cloud could not be more jargon-laden, but is it the future? A recent Two Sigma Ventures report posits yes. The premise: the last decade witnessed a wave of application performance monitoring (APM) companies (like Datadog, New Relic, PagerDuty, etc.) that enabled companies to prevent outages, monitor uptime, and catalyzed the migration to cloud. Next up will be data-driven systems, enabled by machine learning to help with data quality, drift, model performance, and system reliability.

Start-Up Pitch Research: According to a new study, those with cheerful and enthusiastic presentations are more likely to get venture capital funding and less likely to build successful ventures. Surprise! Or not.  

We're Hiring! I made a curated job board. It seems like everyone is hiring. You (or your cousin or student or younger sibling) want to work with fantastic people making a positive dent in their segment of humanity. People and culture matter. I highly recommend each of these companies and know the founders personally: Delivery Associates, Upperline Code, Coding Dojo, The Social Institute, Uplift Groups, and Reduct Video. Please spread and check it out in the link above.

Om Mani Padme Hum - In Memory of Stephen V Smith

I appreciate that you open this email presuming we are going to discuss SPACs, tech multiples, value investing, the best ways to grow your startup, and more of that ilk. 

My belief is we know that all these professional/company building/asset allocation decisions we do are a game. That’s why it’s measured with money, with interest rates, etc. It's competitive. It's important, yes, but 'winning' is not the most important feature. For investing and for living, your most valuable asset is time. 

One of the themes of this newsletter is it’s all personal. The actions people take. The things that are important to them. The events and memories that are meaningful.

On Day 8 of our trek in Nepal, Stevie, one of my new best friends and father to my friend, had a heart attack on the trail and passed. One minute, he was with us laughing, joking, and taking pictures; moments later, his heart had stopped. He was there with two of his children, in one of the most beautiful settings in the world, loving every minute of it. 

My friends knew their father, a retired episcopal minister, would have deeply appreciated a Buddhist cremation beside the river, in the shadow of the mountain, and for us to finish the trek. And that is what we did, spreading Stevie's ashes on the top of the Thorong La Pass at 18,000 feet two days later. 


We know that death is an inevitability, yet the finality might always feel shocking when it happens. Stevie had joined the Declarative Statements community only a few days prior. 

He also had his own email list. I had been added only 5 days before he passed. I was excited to receive his periodic reflections. I liked how he would thank the Lord for the great experiences of life, like tasting his daughter's organic peaches: 'I take no small comfort in the fact that when a donut peach or a red haven explodes in my mouth, and drips down my chin, and transports me to a singular state of bliss, I am in the presence of the Almighty.' and that he signed off with 'blessings'. 

It took only a few days into the trip for me to send Stevie a reflection I wrote on Burning Man in the context of us talking about modern religion and spirituality. And, in response, he wrote,

"Burning oneself down is a rich archetype and a central part of the mystical tradition of all faiths from time immemorial. Personal identity is no more than a construct, as ephemeral as my next breath, and to face this in ourselves takes great courage and determination, even and especially in my ripe old age. God willing, I will get to Burning Man someday, but for the moment, let us keep a gentle grasp on this fleeting life for the gift that it is."



Stevie was deeply thoughtful like that. And caring and eternally optimistic. I am grateful that I met him and become friends in his last days. 

Since this experience, I frequently ask myself: What will I do to keep a gentle grasp on this fleeting life for the gift that it is?  

Thanks for reading, friends. Please always be in touch. 

Friend and DS community member, Miles, would like to remind you to vote. October 24th, tomorrow, is National Vote Early Day.

Blessings,
Katelyn

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