What's 🔥 in Enterprise IT/VC #259

GitLab 😲 and the importance of doing things your own way

Once upon a time, the word was that you could not make money in venture selling to developers. Well, it’s been an insane past couple of years with IPOs of Datadog, now at a $48B market cap and Gitlab which ended the week after an IPO at a $16.5B market cap 😲. It’s amazing how we went from a world of investors who did not know what DevOps was to one where companies are decacorns many times over.

There are so many amazing angles to write about, but this one from Aaron Levie best sums it up for founders…

There is so much chatter and news and “how tos” on twitter and blog posts but in the end, there is no “one way” to start and build a company. If anyone tells you that, believe otherwise. Be an original, take the best from others and find your own path. The biggest outcomes also come from choosing your own path which in the beginning often feels like this.

My own personal experiences include folks telling Rahul at Superhuman he couldn’t scale a business by doing bespoke onboarding…a few years later there was a period of time when everyone was the “Superhuman of X”.

In fact, looking at our portfolio and the 🦄, I can tell you that almost all of them at some point in time had a hard time raising capital with excess of dozens of Nos because folks didn’t believe in the market size, the business model, or what have you but in the end despite what anyone tells you, remember…

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

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Scaling Startups

  1. Painful founder lessons from Ali in his meeting with Steve Jobs

  2. Speaking of exits…great 🧵 for founders…

  3. So true…

  4. Easier to sell the dream vs. being measured on revenue

Enterprise Tech

  1. Must read reports on the State of European/Israeli Tech (Accel) and State of AI (Nathan Benaich) - so happy to have over 60% of our investments in last few yeas in Europe and Israel!

  2. Was viewed as crazy at time by some but…

  3. 🤔…

  4. ☁️ security continues to be on 🔥 as Wiz raised $250M at $6 Billion valuation and Orca raised $550M at $1.8B valuation - both 4-6 months after their last rounds 🤯

  5. k8s on bare metal - upsides and downsides from Saad Malik (Spectro Cloud, a portfolio co) - The New Stack

    “One of them comes in the shape of running apps and the Kubernetes (K8s) platform directly on bare metal servers. The upside? Better performance and of course less cost (say goodbye to hypervisor licenses) and effort (one layer less to manage). Indeed, K8s has everything we need to run our apps directly on top of bare metal machines.

    The downside? Until now it has been generally quite challenging to install, run and manage bare metal K8s clusters, viewed often as a “disconnected” experience between the underlying server and the K8s nodes, let alone treating them as just another “location” of a multi-environment K8s management strategy. But what if there was a way to unify the experience and treat a bare metal server like any other cluster?”

  6. This is 🔥 from Replicated (a port co) - kubernetes theme song for Kubecon

  7. Must listen from OpenView with Kyle Parrish…we at boldstart also hosted Kyle for a chat on day one PLG sales and building out that initial motion


  1. Enterprise software - let’s go!

  2. 🤯 71x NTM Rev for Cloudflare!