Many founders only know their own experience fundraising and don’t hear much about what other founders went through. On Extra Crunch Live on Wednesday, we’re going to remedy that.

Grafana Labs has raised upward of $75 million since it launched in 2014. Lightspeed Venture Partners, and partner Gaurav Gupta to be specific, led both the startup’s Series A and Series B rounds. As far as commitments go, that’s a pretty significant one.

The new and improved Extra Crunch Live pairs founders and the investors who led their earlier rounds to talk about how the deal went down, from the moment they met to the conversations they had (including some disagreements) to the relationship as it exists today. Hell, we may even take a peek at the original pitch deck that made it all happen.

Then, we’ll turn our eyes back to you, the audience. That same founder/investor duo (in this case, Grafana Labs CEO Raj Dutt and LVP’s Gaurav Gupta) will take a look at your pitch decks and give their own feedback. (If you haven’t yet submitted a pitch deck to be torn down on Extra Crunch Live, you can do so here.)

The hour-long episode is sandwiched between two 30-minute rounds of networking. From start to finish, it goes from 11:30 a.m. PST/2:30 p.m. EST to 1:30 p.m. PST/4:30 p.m. EST. And Extra Crunch Live will come to you at the same time, every week, with a new pair of speakers.

So let’s learn a little bit more about Gupta and Dutt.

Before becoming an investor, Gupta enjoyed a rich career in the product development sphere, holding positions at Elastic (where he led product management), Splunk (VP of Products), as well as Google, Gateway and the McKenna Group. He joined Lightspeed in 2019 as a partner, focusing primarily on enterprise software. He’s led investments in Impira, Blameless, Hasura and Panther, and of course, Grafana. He sits on the board of the last three companies in that list.

Dutt is the co-founder and CEO at Grafana Labs, but the fast-growing company isn’t his first go at entrepreneurialism. Dutt also founded and led Voxel, a cloud-hosting startup that was acquired by Internap for $30 million in 2012.

We’re absolutely thrilled to have Gupta and Dutt join us on our first episode of Extra Crunch Live in 2021. As a reminder, Extra Crunch Live is for Extra Crunch members only. We’re coming to you with a new pair of speakers every week, and you can catch everything you missed on-demand if you can’t join us live. It’s worth the cost of the subscription on its own, but EC members also get access to our premium content, including market maps and investor surveys. Long story short? Subscribe, smarty. You won’t regret it.

Oh, and here’s a look at other speakers you can expect to see on Extra Crunch Live:

Aydin Senkut (Felicis) + Kevin Busque (Guideline) — February 10
Steve Loughlin (Accel) + Jason Boehmig (Ironclad) — February 17
Matt Harris (Bain Capital Ventures) + Isaac Oates (Justworks) — February 24

And that’s just the February slate!

All the details to register for this upcoming episode (and more) are available below. Can’t wait to see you there!

Another hour, another billion-dollar round. That’s how February is kicking off. This time it’s Databricks, which just raised $1 billion Series G at a whopping $28 billion post-money valuation.

Databricks is a data-and-AI focused company that interacts with corporate information stored in the public cloud.

News of the new round began leaking last week. Franklin Templeton led the round, which also included new investors Fidelity and Whale Rock. Databricks also raised part of the capital from major cloud vendors including AWS, Alphabet via its CapitalG vehicle, and Salesforce Ventures. Microsoft is a previous investor, and it took part in the round as well.

But we’re not done! Other prior investors including a16z, T. Rowe Price, Tiger Global, BlackRock and Coatue were also involved along with Alkeon Capital Management.

Consider that Databricks just raised a bushel of capital from a mix of cloud companies it works with, public investors it wants as shareholders when it goes public and some private money that is enjoying a stiff markup from their last check into the company.

The company has made its mark with a series of four open-source products with a core data lake product call Delta Lake leading the way. You may recall that another hot data lake company, Snowflake, raised almost a half a billion dollars on a $12.4 billion valuation a year ago before going public last September with a valuation twice that. Databricks has already exceeded that public valuation with this round — as a private company.

When we spoke to Databricks CEO Ali Ghodsi at the time of his company’s $400 million round in 2019, one which valued the company at $6.2 billion at the time, he said his company was the fastest-growing enterprise cloud software companies ever, and that’s saying something.

The company makes money by offering each of those open-source products as a software service and it’s doing exceedingly well at it, so much so that investors were tripping over each other to be part of this deal. In fact, Ghodsi said in a conversation with TechCrunch today that his company had targeted a much more modest $200 million raise, but that figure grew as more parties wanted to invest funds into the company. Even with that, Databricks had to turn capital away, he added, after deciding to cap the round at $1 billion.

The extra $800 million that the company raised will be used for M&A opportunities with an eye on talent, spend on establishing a Lakehouse concept, international expansion, while also expanding its engineering team, the CEO said.

Ghodsi also made clear that he does not intend to let the percentage of revenue that the company spends on R&D to drop, as is common at modern software companies — as many SaaS companies grow, they expend more of their revenue on sales and marketing efforts over product spend, something that Databricks wants to avoid by continuing to invest in engineering talent.

Why? Because Ghodsi says that the pace of innovation in AI is so rapid that IP becomes outdated in just a few years. That means that companies that want to lead in this space will have to stay on the bleeding edge of their market or fall back swiftly.

The Databricks model appears to be working well, with the company closing 2020 at $425 million in annual recurring revenue, or ARR. That figure, up 75% from the year-ago period, is also up from a $350 million run rate at the end of its Q3 2020. (For more on Databricks’ business, product and growth, head here.)

Notably Ghodsi told TechCrunch that this deal only started to come together in December. It’s February 1st today, which means that it took on this bushel of new funding remarkably quickly.

Finally, at $425 million in ARR, is the CEO worried about having a valuation sitting at roughly a 65x multiple? Ghodsi said that he is not. He said that he told his company during an all-hands earlier today that the AI market is a long journey, one that he hopes to be on for decades, and the stock market will go up and down. His point, as far as I could read into it, was that so long as Databricks keeps growing as it has, its valuation will take care of itself (and that seems to be the case so far with this company).

What’s certainly true is that Databricks is now as rich as it has ever been, as large as it has ever been, and in a market that is maturing. Let’s see what it can do with all this money.

Enterprise IT has been completely transformed by SaaS the past decade. Okta last week published a report that showed that the largest companies now use 175 apps, a doubling over the past few years. More professionals have more tools to do their jobs than ever before. It’s an explosion of creativity and expressiveness and operational latitude — but also a recipe for disaster.

It’s one thing to give people and businesses tools — and something else to train them to use those tools effectively. Worse, as the number and complexity of software has skyrocketed the past decade, it’s only become harder for end users to grapple with offering their customers the best possible experience.

That’s the opportunity for a range of new tools that are designed to guide — sometimes forcefully — people to use the software they have in the best possible way, in what you might dub “best practices as a service.” It’s software that is opinionated on what “best” looks like within its domain, and ensures that as many people follow that model as possible with minimal dissension. It’s simplicity-in-a-box for a complex world.

Let me give some examples from a few major fields of startups in e-commerce, security, web development and finally, in my chosen profession, writing to illustrate what I mean.

Each year Okta processes millions of SaaS logons via its authentication system. It kindly aggregates that data to find the most popular apps and publishes an annual report. This year it found that the most popular tool by far was Microsoft Office 365.

It’s worth noting that while app usage popularity varied by region, Office 365 was number one with a bullet across the board, whether globally or when the report broke it down by geographic area. That wasn’t true of any other product in this report, so Office 365 has extensive usage across the world (at least among companies that use Okta).

But as with everything cloud, it’s not a simple matter to say that because lots of people signed onto Office 365, Microsoft is the clear winner in a broader sense. In reality, the cloud is a complex marketplace, and just because people use one tool doesn’t preclude them from using tools that compete directly with it.

As a case in point, consider that the report found that 36% of Microsoft 365 customers were also using Google Workspace (formerly known as G Suite), which offers a similar set of office productivity tools. Further, Okta found that 42% of Office 365 customers were using Zoom and 32% were using Slack.

This is pretty remarkable when you consider that Office 365 bundles Teams with similar functionality for free. What’s more, so does Google with Google Hangouts, so people use the tool they want when they want, and sometimes it seems they use competing versions of the same tool. The report also found that of those Office 365 users, 44% are using Salesforce, 41% AWS, 15% Smartsheet and 14% Tableau (which is owned by Salesforce). Microsoft has products in all those categories.

Microsoft is clearly a big company with a lot of products, but the report blows a hole in the idea that because people like Office 365, they are going to be big fans of other Microsoft products, or that they can count on any kind of brand loyalty across the range of products or even exclusivity within the same product category.

All of this, and much of the other data in this report makes tremendously interesting reading as far as it goes. It’s not a definitive window on the state of SaaS. It’s a definitive reading on the state of Okta customers’ use of SaaS, on the Okta Integration Network (OIN), a point the company readily acknowledges in the report’s methodology section.

“As you read this report, keep in mind that this data is representative of Okta’s customers, the applications and integrations we connect to through the OIN, and the ways in which users access these tools through our service,” the report stated.

But it is a way to look at the state of SaaS taking advantage of the 9400 Okta customers using the network and the 6,500 integrations to the world’s most popular SaaS tools. That gives the company a unique view into the world of SaaS. What you can conclude is that the cloud is complicated, and it’s not a zero-sum game by any means. In fact, being a winner in one area is not a guarantee of winning across the board.