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We’re excited to announce our partnership with and investment in Kustomer. Kustomer is a New York City-based company building the next-generation of customer support platform.

In my first role at Google, I provided account management and customer support to internet publishers.

I remember trying to understand the context around a particular customer case. How large is the customer? What recent interactions have we had with the customer? How satisfied are they? Who is the point of contact? Which products are they using? The information was found in five or six different systems.

2018 is a blockbuster year for software M&A multiples. The prices companies fetch relative to their revenues surpass any of those in the past 7 years. Billion-dollar plus acquisitions in 2018 have commanded a median 17.7x trailing enterprise value to revenue multiple. Nothing in the past seven years is close. In fact, there is not a single acquisition in that range.

Last week, Microsoft acquired Github for $7.5B. It’s a massive acquisition at a massive price relative to other software acquisitions. Why is Microsoft willing to pay so much?

1. Developer identity. Identity has been critical to Microsoft success. Active Directory (AD) forms nexus of the Microsoft enterprise ecosystem. AD contains all the users, their roles, and their rights. The Skype acquisition was also about identity, consumer identity. Github brings identity of a third important demographic: developers.
2. Hard left toward open source. Satya Nadella has pivoted Microsoft toward open source since he became CEO. These are some of the efforts. Microsoft supports Ubuntu on Windows 10. Microsoft has published Linux and FreeBSD for Azure. Microsoft bought Xamarin to help open source .NET. That’s the beginning. There are plenty more open source initiatives here. This acquisition capstones the commitment.
3. Box-out Amazon and Google in the Cloud Wars. “Every” business is moving to the cloud. They will migrate applications, data and code. Microsoft now owns the largest repository of open source software, and the most popular version control system. To migrate enterprise on-prem code to Azure is a huge competitive advantage. It will be easier than any alternative.
4. Cross-sell Github enterprise. Enterprises pay millions of dollars for Github enterprise. Microsoft has one of the largest enterprise customer bases globally. Mix the two, chill, and shake, and you have a new billion dollar revenue business unit for Microsoft.
5. Anticipate the serverless and function-as-a-Service (FaaS) wave. Serverless is a movement in the developer ecosystem. For the past 15 years, developers have shared open source applications and libraries. Today, developers have begun to publish and share individual functions. Imagine pushing a button on Github to instantiate a function or an application. Elegant on-ramp for a developer to become a paying Azure customer.
6. M**&A Intelligence.** Microsoft will observe which open source projects gain momentum. With that first party data set, they can acquire or compete with the teams building those technologies.
7. Network effects. There are very few enterprise companies with network effects. Github is one. They should enjoy winner-take-most dynamics within the developer ecosystem.

Microsoft’s acquisition of Github is a bold strategic bet that will position Microsoft at the forefront of open-source and reinforce their strength in the Cloud Wars.

You’ve just raised a round of financing. Your next step is to build your management team. There are several criteria for finding the right executive. Competency in the field, cultural fit, communication skills, management experience. All of those should be obvious. There is one that is often overlooked. Network.

Recruiting is one of the most important responsibilities for a head of a department. That head will need to scale the team to meet the objectives of the company. Within the first 3 to 6 months, the executive will likely hire several people, maybe 4 maybe 10.

There are five forces driving the startup ecosystem today. They are working together to reinforce a high valuation environment. These forces are:

1. An infusion of capital into Startupland. There are many reasons for this. The money supply in the US has doubled in the last 10 years. A low interest rate environment means a low cost of capital, which means yield is hard to find for cash.
2. VCs raise larger funds and more frequently. Core funds, opportunity funds, supergrowth funds. Private capital has become so abundant that it supplies hundreds of millions and billions to startups. In addition to the size, venture capitalists are raising funds more frequently. Instead of every three years, many VCs are raising every two years. Greater dollars means more competition. And we all know what happens when demand exceeds supply: prices increase.
3. Market maturity. Software models are well understood. Many of the metrics that formerly were applied only to public companies are now applied to SaaS companies. We talk about valuation as a function of new quarterly bookings or revenue multiples/ARR multiples, even at the early stages. There are standard metrics for sales, customer success in marketing efficiency that are used broadly within the industry. There are books written about the ways to build a go to market for software company. All of this means more efficient pricing of startups.
4. Aggressive Acquisition Market and Strong Multiples in the IPO Market. SaaS forward multiples are at ten year highs. The average forward multiple is now 8.5x. This means public companies are worth more when they go public and as they are public. Acquisitions also occur at much larger multiples. The recent Github and Mulesoft acquisitions occurred at astounding multiples relative to public comparables. When startups are valued this highly in the late stage markets and the public markets, the effect is also felt in earlier rounds.
5. Balance Sheets as Competitive Advantage. Balance sheet sizes have become a moat. In addition to technology, network effects, and expertise, a startup’s cash position is a competitive advantage. Imagine two startups in the same space with similar funding. The one that can raise a $250m round from a later stage mega-fund suddenly has a huge and difficult-to-assail advantage.

The question is whether the trade is positive, negative or neutral for founders and investors.

Imagine you came across this ad.

Scientists have discovered a revolutionary new treatment that makes you live longer. It enhances your memory and makes you more creative. It makes you look more attractive. It keeps you slim and lowers food cravings. It protects you from cancer and dementia. It wards off colds and the flu. It lowers your risk of heart attacks and stroke, not to mention diabetes. You’ll even feel happier, less depressed, and less anxious. Are you interested?

Technology innovations swing to a pendulum’s cadence. Sometimes innovations begin with infrastructure changes and reverberate up the stack. Other times, front-end engineers innovate at the application layer, which demand downstream changes in the infrastructure to scale.

The last major epoch of front end evolution has celebrated its ten year anniversary. We’re in a period of punctuated equilibrium. When will we see rapid speciation?

Web 2.0 and mobile applications built on iPhone and Android transformed the way users interacted with technology.

I remember the first time I wrote an OKR (objective and key result) at Google. “You should set your goals so that you attain 70%. That’s success,” my manager told me. “Even better if you have a moonshot goal in there, with a 5% likelihood of success.” I was uneasy with calling 70% goal achievement as success. The habits formed from 17 years of schooling and a 100 point scale run deep.

At Redpoint’s annual investor meeting earlier this year, I quipped, “The day-trading taxi drivers of the dotcom era have been replaced by crypto-trading Uber drivers.” But over the weekend, a grizzled Uber driver with a mane of grey hair and wind-and-sunburnt cheeks asked me about crypto. “Can you explain to me why public key/private key technology is important on the Blockchain?” He pointed out the Bitcoin ATM that charges 10% from his cigarette-infused Prius. “That’s for suckers; Coinbase charges only 2%,” he said as we whizzed past.

There’s the challenge of dealing with uncertainty, where you’re operating in the weird zone that you’re making decisions that have significant long term impact or that are difficult to reverse or course-correct in the face of great uncertainty.

Uncertainty is often unnecessary in the sense that you could, in principle, reduce the uncertainty. You could go research the question more. You could obtain more information, or run an experiment.

It’s not cosmic uncertainty, without absolute knowability. When there’s true, deep, un-mitigatable uncertainty then it’s not to hard to say, “we’re just going to choose something and make the best decision we can.”