Hello Twitter! For my first post, I thought I'd share the slides of a talk I've recently given at a large tech company and institutional investment funds on qualitative aspects of enterprise software investing and the way to identify the quality companies
Probably will close out 2019 w/ 45 books read, ones I thought were most impactful:
Poor Charlies Alamanc
Alchemy
The Halo Effect
Why We Sleep
Boyd
Red Notice
Thinking In Bets
Farsighted
Rereads: Fooled By Randomness and Thinking Fast & Slow
So yes stocks are down but can we all talk about how freakin crazy the execution of $DDOG has been!!
When people talk about expanding TAM and using a core product as a wedge into a core workflow, Datadog is the case study to bring up 🤯
👀 customers w/ 4+ products section
❤️ Twitter
@JerryCap
asked how many companies trading at >10x sales have been multi-baggers
@jaminball
did the excellent analysis:
27 companies (not including M&A like Mulesoft) all beat the Nasdaq with > 10% CAGR trading > 10x NTM sales at one point
@sethrosen
Coming out of banking and joining a startup was the worst day of my life
Went from having a great Intel laptop to a MacBook with no freaking Excel access and none of the keyboard shortcuts id worked so hard to learn were applicable 🤣
Now I can’t go back to a PC lol
Some Personal News
🔥 up to be a partner
@Boldstartvc
🥳 to my colleague
@ellenchisa
for also becoming a partner
Wanted to share a few things I've learned along the way to commemorate the occasion
Check out our new fund announcement in 🧵below!
@pitdesi
@bchesky
Hotels > Airbnbs
Used to be the opposite when first started out but now the novelty has worn off and the experience is just terrible compared to hotels
4 yrs ago multiple people took a leap of faith
Me transitioning from growth to inception investing
@edsim
,
@etdurbin
and the entire
@Boldstartvc
crew taking a bet on me
When I first met Ed, the longest job I had held was 2 years, I’d done multiple things for 1 yr stints from
Great thread on the risks that Germany and places like California face by shutting down nuclear power facilities
@wolfejosh
you’ve been talking about this for awhile and this thread lays out the risks coherently
Really hope California does not weaken the power grid further
1/ By systematically shutting down baseload-critical nuclear power facilities and replacing them with intermittent renewable energy, Germany has left itself – and by extension, the entire European Union – vulnerable to shortages of reliable sources of electricity.
Some personal news
I'm taking my talents to South....ern California 🤣
Moving to Santa Monica in early Oct
Yes, still
@Boldstartvc
, our companies are all over the globe so doesn't matter where I am
If you have folks I should meet in LA, please tag them below or DM me!
Some personal news....just messing with y'all 🤣
I created a personal website on Notion w/ talks, blog posts & other random stuff (link in bio)
Also I'm 🚀 a blog called Software Snack Bites! It's free & <5 min reads weekly on Weds
Subscribe below!👇
Some fun news 🥳
Couldn’t be more excited to have additional 🔥power to support more incredible founders at company formation 🏗
For the IT nerds out there, see if you can spot the Easter egg 👀
Announcing $367M in new
@Boldstartvc
funds, vi $192,168,111 + opp iii $175M for existing cos🚀
Same mission + more excited than ever to be a Day One partner for technical, under🐶 founders building the future of Developer First, Crypto Infra & SaaS
Who's ready to build 🏗️?
The classic VC response is “sorry it’s not a fit right now but let’s stay in touch for the future”
Fun thing about being a first check seed investor means when you say this, you legit mean let’s keep hanging out since I just lost our chance to ever invest 🤣
Software Snack Bites
#17
: Constellation Software & Org Design
- Why $CSU.TO makes 💵
- How CSU's competitive advantage is more of a function of org design than anything else
- What can we learn from the org design and how does it help CSU operate
Damn
@sequoia
gets complimented by Charlie Munger as the "most remarkable investment firm out there"
That may be the highest compliment a VC fund has ever received!
Snack Bites
#48
: I'm Moving Back to SF!
❤️ LA but the network effect in SF especially in enterprise software is too 💪 to keep me away
Can't wait to see everyone much more often especially around conference time and other events!
Spurred on by the podcast between
@collision
&
@patrick_oshag
I continue to think one of the most fun things about studying public companies is the broader learnings you can use to apply to company building at the earlier stages, 👇🏾
This was soooo good. Zuck Harvard CS 50 lecture in 2005, a year after starting Facebook. Talks about scaling distributed systems, managing database complexity, mental models for building a company, etc. Some particular thoughts I enjoyed in thread below 👇
For the 1st time in
@Boldstartvc
history we are hiring an Associate!
If you're passionate about enterprise software and helping founders achieve their goals, we'd love to hear from you!
Please apply below. We're excited to meet!
Wow never looked at Amazon’s products like this before. Pretty interesting framework. Betting on infrastructure in all parts of of a business not just software
🎧 Nivida, Groq & HBM - What's Ahead for Semis
@_fabknowledge_
dropping knowledge as always
- What is High Bandwidth Memory
- Where Inference Specific Chips Fall Short
- ASICs vs GPUs
- Why $NVDA is well positioned to keep winning
More in 🧵
Weight loss update
Down 22 lbs in 5 months
Can see from graph below that have fought plateaus and increases (mostly from going out to eat more with friends post vaccine)
@territoryfoods
has been a godsend
Also some light macro focus, eating more protein as % of each meal
Just got cleared to 🚴 again!!
Almost 6 months since the Achilles tear, let’s go!!!
If anyone wants to hit the road with someone who will be slow and with limited current stamina (sounds like a good time i know 🤣), give me a shout!
Announcing the $INFRA index, the worlds first pure Software Infrastructure Index powered by
@go_thematic
Read more in post below or this 🧵
Mission critical software infra will continue to power the world going forward & we need a way to capture it
This is THE BEST tactical podcast I've heard to date on leadership, recruiting, sales practices, & engineering an amazing gtm engine
John McMahon created the MEDDIC sales qualification framework & board member on $SNOW, $MDB, etc
Learnings in a 🧵👇
I don't think investors (me included) think about enough is Base Rates, essentially the probability of something occurring based on historical context, it's a bayesian way of probabilistic thinking, I want to use this thinking in the context of Slack
I've been quoted saying "the market won't bottom until $DDOG hits 10x sales"
Well we're there
Hard to call a bottom especially since so much uncertainty around NTM rev # but at ~$2B ARR with the steady state FCF margin profile of this biz, the dog is cheap imo
🎩
@KoyfinCharts
The classic
@okta
state of Apps report is out and it’s a great one to read. Some standout charts to me are threaded below but there’s tons of good detail in the report
My colleague
@edsim
stands quietly behind the founders he supports to help them achieve their visions
He has accomplished a huge amount and is finally getting some recognition as
#1
on this list
Incredible transcript on multidisciplinary learning from Peter Kaufman, author of Poor Charlie's Almanac (best book I've ever read on thinking). Kaufman in the paragraph attached describes how he went about learning the big ideas from different fields
@trengriffin
@patrick_oshag
Oooh that’s a good one, also Munger’s Psychology of Human Misjudgement just playing in repeat to sear incentives into your brain
New SSB pod w/
@chrishuskey
, Partner at Octahedron Capital
The
@databricks
deep dive you've been waiting for!
- GenAI impact
- The fast evolving competitive landscape
- Overview of platform components
Audio clips in 🧵 below
There's a quote by
@FrankQuattrone
on success that I love because of its simplicity
90% is showing up
9% is likeability
1% is smarts
Qatalyst performs consistently at the top of its field and its employees still repeat this quote to remind them of what matters
Ain't no better feeling then having enough 💰 to give your parents whatever the f*$k they want 🤣
Past yr gave dad a new grill and my mom a water rower, stuff that they wouldn't purchase on their own & couldn't when younger as they were saving up for my sis and I 🙏
In a world where all the focus is on Net Retention
ServiceNow $NOW stands alone on consistently reporting renewal rates every year
The results are 🤯
Cohort chart showing expansion is below
Teams that work out together stay together 💪🏾
Nearly all the
@Boldstartvc
team getting pumped for the AGM!
@edsim
& I didn’t coordinate outfits I promise 🤣
Special guest appearance from the newest Boldstart partner Walter (joining George…hard to tell ‘em apart 😀)!!
Whoa! Hands down the best movie I’ve seen recently is “Molly’s Game” on Netflix. True story about a 2 time Olympic skier who ran legal and illegal poker games with some of the richest people in the world and got indicted by the govt in a RICO case involving mobs
Well the cats out of the bag, excited to be joining
@Boldstartvc
. The companies that we back are defining the enterprise software ecosystem and I can't wait to be spending all of my time helping founders accomplish their goals. Looking forward to hustling hard for our founders!
Some books that I've read this yr, most impactful ones that I either reread or will reread in future were:
Halo Effect
Poor Charlie's Almanac
The Score Takes Care of Itself
Boyd
Why We Sleep
Dead Companies Walking
Thinking Fast & Slow
Thinking in Bets
Never Split the Difference
Counting calories works!
Down 5 lbs in a month simply by logging cals & sticking to target
Biggest thing you notice is evaluating tradeoffs in food
You want a cupcake and that may mean no pizza or that hot chocolate that tastes like crap?...prob not worth it
Still lots to do!
Software Development Lifecycle market map from Morgan Stanley
What's most interesting is how many winners there are in each area
Rising tide lifts all boats
This post by
@itunpredictable
is a must read. I've been looking for a concise overview of dev tooling for awhile now and Justin's post is the only one I've seen. Covers writing, shipping, and monitoring code! Best thing I've read this week!
A case study should be written on $DDOG (Datadog) execution in APM from GA to best of breed in 5 years!!
The below marked up magic quadrant is from
@hhhypergrowth
excellent premium newsletter
Highly recommend subbing for those who closely watch software infra
The dog 👀
Software Snack Bites
#22
: State of OpenCloud Report Deep Dive
- 1st post of 2022 covering some personal news 🤣
- Diving into my favorite annual report on OSS and infra software from
@BatteryVentures
- GTM models, software trends, and of course the ☁️
🙏to the 200+ people that signed up for my substack already
1st <5 min read post delivered!
Its about the convergence of product & gtm as told through the lens of product, messaging, & onboarding website screenshots from
@CrowdStrike
and
@snyksec
👇
The Future of FinTech: A Venture Capitalist's Perspective Ft. Marc Andre... Excellent podcast with some great anecdotes about business models and founders; favorite quote is Stripe co-founder saying our customers do not exist yet
🔥 This was a masterclass on Semiconductors 🔥
SSB Pod
#4
-
@FoolAllTheTime
, Founder of
@_fabknowledge_
Detailed Primer on Semis Industry, AI's effect on Chips, Trends in Chip Specialization
Full Episode 👇
Apple:
Spotify:
Snack Bites
#25
: Atlassian $TEAM - Racing to the ☁️
- Why Atlassian is so focused on cloud
- How are they pulling of the migration
- Why Jira Service Mgmt is such a big deal in attacking a massive market with a new gtm and product approach
- 🤯 stats
Purchases that have changed my life recently
Cordless dyson vacuum
Vitamix
8 Sleep mattress
(Cleaning, smoothies, and sleep highlights are how I know I’m getting old 🤣)
Slow summer month they said...
Partnering with 4 new companies
@Boldstartvc
in the last few weeks!!
Quality of founders utilizing LLMs to AUGMENT core products and REIMAGINE existing legacy categories has us fired up over here!
Crazy to look at trends overtime
In 2013 I was 180lbs, from there a steady climb for 8 years till Jan 2021 when I was 219
A health scare and I was able to drop to 200lbs and bounced between 200-205
Recently started working w/
@bencanning87
and am now 192lbs w/ better body comp
What a nightmare in the data landscape currently looks like from a real customer:
Use Redshift for data storage, MySQL for operational data, Periscope for BI, dbt for ETL into Redshift, and Stitch to ETL crm data
😱🤯
Officially purchased a Nintendo Switch
I haven't played a video game in like 10 years
But suddenly got a craving to play Wii Tennis and DDR 🤣
Apparently the only way to do that these days is through the Switch so any game recs, throw them my way!
Happy Birthday to my colleague and friend
@edsim
!
Although you’re close to getting that senior citizen discount, I still learn new things from you everyday 🤣
Lots more to do together 💪🏾
This cake says it all about Ed’s mentality
Coatue has navigated the past few major market pullbacks like 🪄
Great short interview with
@plaffont
:
I liked this part, mind you still in 70% cash but seeing some good opportunities now and continued focus on transformational trends
The IPO window is basically closed until either Stripe or Databricks breaks it open and the public market remembers how crazy the growth of some of these enterprise software companies are 🤣
P.S. Yes I know growth is not the same as free cash flow or relative valuations
Fintwit is back to its fav topic of do DCFs matter. What matters is understanding expectations underlying the valuation & then examining drivers that could create upside/downside to that. If you want to use a DCF, eat a donut, or go running to do that then who the hell cares
We
@Boldstartvc
are excited to support startups building on
@Cloudflare
Workers 🎉
@liveblocks
a portfolio co, currently uses Workers & Durable Objects to provide APIs to devs efficiently!
We hope to find & support many more in the future
Congrats
@miawang__
on this launch 🚀
🎧 How Hackers Do their Work w/
@ArchAngelDDay
- Figuring out entry points for an exploit
- Most common vulnerabilities
- Bug Bounties vs Pen Testing
Douglas is a top grossing hacker,
@Hacker0x01
& Sr Security Eng
@elastic
Links to listen in 👇 tweet
Satya Nadella, CEO of Microsoft
Great talk about escaping the innovators dilemma and changing incentive structures to enact cultural change; I.e. moving into compute/storage was lower GM but generates more absolute FCF so comped team on engagement metrics
The Rise of Platform Engineering
(aka why DevEx is the best thing since sliced bread)
Combining thoughts from
@StackOverflow
,
@davidmcj
,
@danielbryantuk
, &
@GergelyOrosz
Here's a <5 min read on why Platform Eng teams have more 💰 these days
Just has Achilles tendon surgery so apologize if I am slower responding for next few weeks
Gonna be fairly immobile
Pls give me your best podcasts, interesting articles, hobbies to pass the time!! 🙏🏾
Reminder building enterprise software takes a LONG time, similar to fintech, revenue traction compounds in out years
Patience is needed, why we preach not pursuing largest revenue deal at early stage, product velocity & learning more important than $ at that stage h/t
@LennyIce
If y'all are interested in my thoughts on enterprise SaaS, the "sandwich" go-to-market model that is spreading through the SaaS world, & how we identify special founders check out this interview I did w/
@thecaptable
!
It's an awesome newsletter w/ interviews plus financing news
Looking through old investment memos of mine. This one for Anaplan's $PLAN pre-IPO round is hilarious. The sales multiples I used was 12x on the high end 🤣
Currently 21x FWD and $11B EV
Markets are a lot bigger than we all think!
A little pre wedding 🎁 for me getting to take the cover off our investment in
@cloudqueryio
@yevgenypats
@p0werhead
are building dev first ☁️asset inventory to increase visibility around infrastructure sprawl for devs everywhere
🙏
@ron_miller
for 👇
🎧 AI Agent-Assisted Flow Engineering w/
@itamar_mar
CEO of
@CodiumAI
on:
- AlphaCodium beating Deepmind & OpenAI
- Shift from Prompt Eng to Flow Engineering 🎩
@karpathy
Stream on X or other platforms 👇
Lots of tips/tactics on all things product led growth in this talk by
@KyleHParrish
of
@figmadesign
- Analytics & tooling
- What data signals the team prioritizes
- How product feedback from free and paid customers flows
Will rewatch multiple times!
We all know about Salesforce M&A: Heroku, ExactTarget, Demandware, Mulesoft, Tableau, Click Software, etc
But the ventures arm is also crushing it, amazing job by
@mdgarratt
and the team
Sampling in the pics below