What's 🔥 in Enterprise IT/VC #208

Going big and leap of faith investing 🌜

Paul Graham wrote a great essay this week on how to not let fear of being lame hold you back from doing great and ambitious work. He shares some great mental models on overcoming these fears.

We just don't have enough experience with early versions of ambitious projects to know how to respond to them. We judge them as we would judge more finished work, or less ambitious projects. We don't realize they're a special case.

And this mental trick is spot on when investing on day one and imagining the future…

"The right way to deal with new ideas is to treat them as a challenge to your imagination — not just to have lower standards, but to switch polarity entirely, from listing the reasons an idea won't work to trying to think of ways it could. That's what I do when I meet people with new ideas.”

This is a mental model I share and think about constantly @boldstart.

Ed Sim @edsim

so easy to talk yourself out of an opportunity to invest early due to competition and easy to say why someone can’t do this, but flip the question and ask if someone were to take this down, how would you do it? what is team, product, GTM?

With a deeper dive into enterprise (click for thread)

Ed Sim @edsim

1/ Enterprise is 🔥 + few net new areas to invest w/out competition. Always easy to pass because of this, but in order to put $ to work, you need to flip the ?, + ask if someone were to take this down, how would you do it? what is team, product, GTM?

Semil Shah from Haystack similarly shares this sentiment when discussing his miss on Retool (just closed $50mm round led by Sequoia)

Semil @semil

this is one of my biggest oversight mistakes, think about this one quite often. David had the entrepreneurial hustle in spades, but I couldn’t understand what this could be.

We all have these big misses! And I’m continually thinking about our first principle at boldstart which is to partner with incredible technical founders who can see the future (especially hard in new markets - click for full thread).

Ed Sim @edsim

First impressions matter! Looking back at many of our best investments, we knew in that first meeting that we wanted in Diligence ends up being confirmatory Same goes 4 companies where you r on the fence, usually end up not doing because your brain is wired to look for issues

Ultimately, it comes down to the founders and not overthinking it.

Ed Sim @edsim

and on day one, we can turn ourselves sideways if we overthink it, need amazing founder who builds, product obsessed, atomic + narrow use case/persona and not broad architectures, unique insight, with potential to expand over time

Since we are in the business of seeking asymmetric returns, those seemingly crazy ideas are the ones that may be your fund returners. And sometimes it just requires that Indiana Jones moment, stepping into the unknown and taking that leap of faith.

So net net, reframe your mental model, think about why something can be big, ignore the skeptics, and shoot for the 🌝. Continue to look back at what went well and what you missed and iterate! This isn’t easy but so much fun!

As always 🙏🏼 for reading and please like and share with your friends and colleagues!

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Scaling Startups

1. Thanks Alex Yampolskiy, cofounder of Security Scorecard, for sharing this gem with Tom Mendoza from Netapp and board of UIPath, Varonis

   Great advice from an excellent visionary leader Tom Mendoza: "When times are tough be supportive, when times are good inject tension" - most managers do the opposite.

   Goes back to my 3 Chs - know when to cheer, know when to challenge, know when to cheer

   Ed Sim @edsim

   The emotional aspects of founder/investor relationship often overlooked for the Xs + Os, but IMO, this is 1 of most important dynamics, esp. early What I’ve learned over many years is that investors who r truly supportive + engaged know when to: 👏🏼 Cheer 🧑‍🏫 Challenge 😎 Chill

2. 👇🏼💯 even harder in today’s day and age then when written by Rich Barton, Zillow, Glassdoor, etc in 2009!

   Bill Gurley @bgurley

   If you are trying to name your company or product — this is the best thing ever written on the subject. hopperanddropper.com/syllables-scra… I would amend one extra argument. An unusual name is over discussed which reinforces brain pointers. Generic brands are forgotten & have no spirit.

   

   hopperanddropper.comSyllables, Scrabble Letters, and Picking Brand Names - Rich Barton | HopperandDropper.com

3. Finally got to this from my saved articles - Trista Myers from Salesforce Ventures shares learnings from the Cloud 100 virtual event and how you can run an amazing one yourself

4. Remember, new features drive more usage and growth for product led growth companies - Superhuman one of the best at driving this. Here’s the latest on their “select all” archive functionality. Last big launch was calendar 2 months ago with similar results.

   rahulvohra @rahulvohra

   1.8M threads archived just today! 🔥📈🚀 #HitZero

   

   

   rahulvohra @rahulvohra

   We just launched our most requested feature: Select All, redesigned for @Superhuman! 🎉 Select All in other email apps is broken. Why? We almost never want to select everything; we almost always want to select everything _past_ a certain point. You can now do just that! 😄 https://t.co/qrl6BGyoXO

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Enterprise Tech

1. Goldman Sachs with its Software Sector Report for Oct. 2020 - notice the Dev First segment up 92% - so much more room to grow

   

2. Interesting stat from Retool blog post announcing their $50mm round led by Sequoia.

   A large chunk of software built is actually purely internal-facing — Gartner estimates that up to half of all code is written for internal usage, and Forrester estimates that $120B / year is spent on custom, internal software. All companies (including those mentioned above) have an enormous amount of internal software, just so the sales, marketing, support, operations, legal, and finance teams can continue operating.

3. 3rd Annual State of AI Report is out (Nathan Benaich and Ian Hogarth)! Great overview of the latest in research, talent, industry, and what’s next. Over 170 slides of goodness.

   

4. My friends at Tackle.io published their state of the cloud marketplace. 35% of the Cloud 100 are marketplace sellers and if you’re a startup thinking about offering on one of the cloud marketplaces, this is all you need to know - why buyers and why sellers

   
   

5. Great read on how Netflix builds its distributed tracing infrastructure - from use of open zipkin for tracing to Mantis for stream processing and the decisions on why each was chosen.

   

6. Kelly Shortridge from Capsule 8 has a great keynote from SnykCon on Security Chaos Engineering and the whys and hows

   Kelly Shortridge @swagitda_

   Thanks to everyone who caught the live stream of my #snykcon keynote on eradicating security theater! Loved the live comments, collaborative snark, and appreciation for my theater analogies. Slides are up on my personal site here: swagitda.com/speaking/Exit-…

   

7. Paypal enters crypto market and also looking to make acquisitions

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Markets

1. Tomasz Tunguz breaks out why we will see more public market activity in startupland as valuations in public better than private

   

2. No more on-prem for Atlassian as it moves to all ☁️ - stock moves 8%+ on day of announcement

3. Surprised and not so surprised…Tech accounts for 40% of S&P market cap now with Apple representing 7% alone, last seen during Internet bubble (more from WSJ)

   

4. Top tech stocks for 2020 according to the Information…