What's 🔥 in Enterprise IT/VC #166

boldstart 2019 review and 2020 enterprise predictions

Happy New Year and decade to all! May this be a healthy and prosperous one for all of my readers. As promised from last week, here is my annual recap on boldstart in 2019 and thoughts on What’s 🔥 in Enterprise for 2020. Warning, I’m a VC so some of these trends may be biased 😃 as I name a portfolio company or two in each thread, but I hope it will at least give you a window into how we are thinking about this upcoming year. Here’s #8 on what to expect in 2020:

8. Rise of FinOps: As cloud and SaaS continue to dominate, the sheer costs of cloud hosting are becoming a bigger and bigger line item under cost of goods sold. While version 1.0 was all about analyzing cloud spend reactively, the next generation will need to be proactive and help companies set policies upfront and understand, control, and manage these costs dynamically. FinOps helps companies address this problem as it’s incredibly complicated for someone in finance to know why costs spiked because a new product release was made or because data science used more GPUs to train their model. Coordinating all of these processes and allowing companies to set policies while providing self service will be the basis of many new companies in 2020. With infrastructure as code rising, we believe that the opportunity to proactively manage and codify this is already happening and that’s why excited about companies like Env0 (a portfolio co).

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Scaling Startups

  1. must read from one of the best CEOs in enterprise tech, founder/CEO of MySQL one of first commercially successful open source companies and now CEO of HackerOne. I had the pleasure of being an investor in one of his former companies Eucalyptus Software which was sold to HP.

  2. Love this post from Lan Xuezhao from Basis Set Ventures on what traits make a successful founder.

Enterprise Tech

  1. Cyber security and nation state risk will be an ongoing theme in the next decade. First let’s start with Iran. Given the incidents in the past few days, it’s pretty clear that we can expect a massive cyber attack from Iran. Likely targets will include mission critical industrial control systems and financial services.

    One such avenue could be Triton which was hailed as the world’s most murderous malware. It’s designed to disable safety systems to prevent catastrophic industrial events.

    At first, Triton was widely thought to be the work of Iran, given that it and Saudi Arabia are archenemies. But cyber-whodunnits are rarely straightforward. In a report published last October, FireEye, a cybersecurity firm that was called in at the very beginning of the Triton investigation, fingered a different culprit: Russia.

    On a less threatening front, the WSJ has a deep dive into the Cloud Hopper attack orchestrated by Chinese (WSJ Paywall, try Verge for a summary as well) intelligence services and Yahoo news has an expose on how hard it is to maintain cover for spies in the digital age.

  2. A decade in review in software development and infrastructure from Cindy Sridharan - she is spot on with much of her highlights.

  3. Where does the RPA market go in 2020. Can bots evolve from mimicking tasks to taking on jobs? In addition as the number of bots scale in an enterprise

    "Few tools exist today to govern what bots do in the workplace," FortressIQ's Chowdhry said. For instance, a bot that is responding to an inquiry could wrongly answer several hundred questions to a customer without any oversight. Additionally, since bots are expected to work 24/7, when they break or stop due to an unforeseen reason, there's usually no human available to pick up the work, thus resulting in loss of overall productivity. This problem will become more serious as bots continue to rapidly grow in the enterprise.


  1. Small is the New Big Thing - interesting article from Ruchir Sharma, Morgan Stanley’s Chief Global Strategist, on what the next decade may bring

    These forces conspire to unseat the global giants, which are mainly American. The United States market accounts for well over half of the global value of stock markets, and has never been more expensive relative to other national markets. But remember, churn is the norm. Among the world’s 10 largest companies today, only one (Microsoft) was on the top 10 list in December 2009.

    If the usual pattern holds, it’s likely that America will peak and smaller nations and companies will make a comeback. If the 2010s were a golden age for the world’s largest economy and its megacorporations, the 2020s are likely to be remembered as the decade when smaller was beautiful again.

  2. The Information predicts Slack will be acquired in 2020 with potential suitors as Amazon, Cisco, and Salesforce. Competition from Microsoft means sales and marketing expenses increasing, growth slowing.

    The company’s annual sales grew 110% in fiscal 2018, which ended last Jan. 31, from the prior year. In fiscal 2019, that figure fell to 82%. In its most recent earnings report, Slack forecast that revenue growth for fiscal 2020 will fall even further to around 55%. Meanwhile, its net loss rose to about $88 million in the third quarter, from nearly $48 million a year earlier.