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Should Dell have pursued a more aggressive debt-reduction move with VMware?

When Dell announced it was spinning out VMware yesterday, the move itself wasn’t surprising; there had been public speculation for some time. But Dell could have gone a number of ways in this deal, despite its choice to spin VMware out as a separate company with a constituent dividend instead of an outright sale.

The dividend route, which involves a payment to shareholders between $11.5 billion and $12 billion, has the advantage of being tax-free (or at least that’s what Dell hopes as it petitions the IRS). For Dell, which owns 81% of VMware, the dividend translates to somewhere between $9.3 billion and $9.7 billion in cash, which the company plans to use to pay down a portion of the huge debt it still holds from its $58 billion EMC purchase in 2016.

Dell hopes to have its cake and eat it too with this deal: It generates a large slug of cash to use for personal debt relief while securing a five-year commercial deal that should keep the two companies closely aligned.

VMware was the crown jewel in that transaction, giving Dell an inroad to the cloud it had lacked prior to the deal. For context, VMware popularized the notion of the virtual machine, a concept that led to the development of cloud computing as we know it today. It has since expanded much more broadly beyond that, giving Dell a solid foothold in cloud native computing.

Dell hopes to have its cake and eat it too with this deal: It generates a large slug of cash to use for personal debt relief while securing a five-year commercial deal that should keep the two companies closely aligned. Dell CEO Michael Dell will remain chairman of the VMware board, which should help smooth the post-spinout relationship.

But could Dell have extracted more cash out of the deal?

Doing what’s best for everyone

Patrick Moorhead, principal analyst at Moor Insights and Strategies, says that beyond the cash transaction, the deal provides a way for the companies to continue working closely together with the least amount of disruption.

“In the end, this move is more about maximizing the Dell and VMware stock price [in a way that] doesn’t impact customers, ISVs or the channel. Wall Street wasn’t valuing the two companies together nearly as [strongly] as I believe it will as separate entities,” Moorhead said.

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How startups can ensure CCPA and GDPR compliance in 2021

Data is the most valuable asset for any business in 2021. If your business is online and collecting customer personal information, your business is dealing in data, which means data privacy compliance regulations will apply to everyone — no matter the company’s size.

Small startups might not think the world’s strictest data privacy laws — the California Consumer Privacy Act (CCPA) and Europe’s General Data Protection Regulation (GDPR) — apply to them, but it’s important to enact best data management practices before a legal situation arises.

Data compliance is not only critical to a company’s daily functions; if done wrong or not done at all, it can be quite costly for companies of all sizes.

For example, failing to comply with the GDPR can result in legal fines of €20 million or 4% of annual revenue. Under the CCPA, fines can also escalate quickly, to the tune of $2,500 to $7,500 per person whose data is exposed during a data breach.

If the data of 1,000 customers is compromised in a cybersecurity incident, that would add up to $7.5 million. The company can also be sued in class action claims or suffer reputational damage, resulting in lost business costs.

It is also important to recognize some benefits of good data management. If a company takes a proactive approach to data privacy, it may mitigate the impact of a data breach, which the government can take into consideration when assessing legal fines. In addition, companies can benefit from business insights, reduced storage costs and increased employee productivity, which can all make a big impact on the company’s bottom line.

Challenges of data compliance for startups

Data compliance is not only critical to a company’s daily functions; if done wrong or not done at all, it can be quite costly for companies of all sizes. For example, Vodafone Spain was recently fined $9.72 million under GDPR data protection failures, and enforcement trackers show schools, associations, municipalities, homeowners associations and more are also receiving fines.

GDPR regulators have issued $332.4 million in fines since the law was enacted almost two years ago and are being more aggressive with enforcement. While California’s attorney general started CCPA enforcement on July 1, 2020, the newly passed California Privacy Rights Act (CPRA) only recently created a state agency to more effectively enforce compliance for any company storing information of residents in California, a major hub of U.S. startups.

That is why in this age, data privacy compliance is key to a successful business. Unfortunately, many startups are at a disadvantage for many reasons, including:

  • Fewer resources and smaller teams — This means there are no designated data privacy officers, privacy attorneys or legal counsel dedicated to data privacy issues.
  • Lack of planning — This might be characterized by being unable to handle data privacy information requests (DSARs, or “data subject access requests”) to help fulfill the customer’s data rights or not having an overall program in place to deal with major data breaches, forcing a reactive instead of a proactive response, which can be time-consuming, slow and expensive.

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Billion-dollar B2B: cloud-first enterprise tech behemoths have massive potential

More than half a decade ago, my Battery Ventures partner Neeraj Agrawal penned a widely read post offering advice for enterprise-software companies hoping to reach $100 million in annual recurring revenue.

His playbook, dubbed “T2D3” — for “triple, triple, double, double, double,” referring to the stages at which a software company’s revenue should multiply — helped many high-growth startups index their growth. It also highlighted the broader explosion in industry value creation stemming from the transition of on-premise software to the cloud.

Fast forward to today, and many of T2D3’s insights are still relevant. But now it’s time to update T2D3 to account for some of the tectonic changes shaping a broader universe of B2B tech — and pushing companies to grow at rates we’ve never seen before.

One of the biggest factors driving billion-dollar B2Bs is a simple but important shift in how organizations buy enterprise technology today.

I call this new paradigm “billion-dollar B2B.” It refers to the forces shaping a new class of cloud-first, enterprise-tech behemoths with the potential to reach $1 billion in ARR — and achieve market capitalizations in excess of $50 billion or even $100 billion.

In the past several years, we’ve seen a pioneering group of B2B standouts — Twilio, Shopify, Atlassian, Okta, Coupa*, MongoDB and Zscaler, for example — approach or exceed the $1 billion revenue mark and see their market capitalizations surge 10 times or more from their IPOs to the present day (as of March 31), according to CapIQ data.

More recently, iconic companies like data giant Snowflake and video-conferencing mainstay Zoom came out of the IPO gate at even higher valuations. Zoom, with 2020 revenue of just under $883 million, is now worth close to $100 billion, per CapIQ data.

Graphic showing market cap at IPO and market cap today of various companies.

Image Credits: Battery Ventures via FactSet. Note that market data is current as of April 3, 2021.

In the wings are other B2B super-unicorns like Databricks* and UiPath, which have each raised private financing rounds at valuations of more than $20 billion, per public reports, which is unprecedented in the software industry.

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Do you fit the mold for the next generation of values-driven VCs?

More individuals than ever are donning the investor cap. Almost a fifth of U.S. equity trading in 2020 was driven by mom-and-pop investors — up from around 15% in the previous year. With such impressive returns to be made, many are deciding to set up a full-fledged investment business.

With the fundraising world becoming more democratic and accessible, we should help people find the right path to setting up a venture capital firm and also make sure the right people are entering the VC sphere. Startups are changing, and any new investment manager will have to adapt to the shifting landscape. VCs today have to provide more than money to get the best portfolio, and they must have a strong focus on impact to get the best institutional investors into their funds.

Startup investors can be the financial backbone for mass disruption. That’s why, at Founder Institute, we believe in the need for more VCs with strong values: Because they will prop up the companies that will build a brighter future for humanity. We’re not the only ones — our first “accelerator for ethical VCs” was oversubscribed.

VCs today have to provide more than money to get the best portfolio, and they must have a strong focus on impact to get the best institutional investors into their funds.

So if you want to lead your own VC fund in 2021, here are the main questions aspiring investors need to ask themselves.

Are you doing this for the right reasons?

Investing in startups is not just about making money. In selecting the startups that will become future industry leaders, VCs have a lot more power than most to do good (or harm). If you’re only interested in money, you likely won’t go too far. Identifying the greatest businesses means seeing beyond their capital into the longevity of their vision, their real-life impact on society, and how much consumers will love or hate them.

After all: Most startup founders pour their blood, sweat and tears into building a business not just to make money, but also to make an impact on the world and build products that align with their mission. Any new venture capitalist looking to attract the best founders needs to think about the vision and mission of their fund in the same terms.

Although VC firms have been slow on the uptake when it comes to environmental, social and governance (ESG) goals, there are signs that times are changing. Some firms are forming a community around implementing ESG, not only because of the external impact but because it furthers their business goals. To help accelerate this trend, we asked our VC Lab participants to take The Mensarius Oath (Latin for “banker” or “financier”), a professional code of conduct for finance professionals to create an ethical, prosperous and healthy world.

What value do you bring to the table?

The number of VCs are growing and the industry is increasingly becoming concentrated. This means that simply offering large sums of money won’t get you traction with the best startups. Founders are looking for value over volume — they usually want mission alignment, connections, value-added services and industry expertise more than a blank check.

Remember that the best founders get to choose their VCs from a menu of options, not the other way around. To convince them that you’re the right match, you’ll need a proven track record in the same industry (or transferable experience from another industry) and referrals from credible people. You’ll also need a strong value proposition or niche that sets you apart from other funds. For example, Untapped Capital invests in “unexpected” and “undernetworked” founders, while R42 Group invests in AI and longevity-focused businesses.

If you don’t think you’ve got the profile to offer value to founders just yet, it’s worth taking some time to lay out exactly who you are. That is: what you hope to achieve as a fund manager, the vision you have for your portfolio companies and how you alone can help them get there.

What’s your secret sauce?

As a new VC fund without historical data points, limited partners (LPs) will naturally be cautious to invest in your fund. So, you have to build a brand that tells your story and proves your reputation.

Go back to the basics and pinpoint exactly what your strengths are. If you’re having trouble finding inspiration, use statements like, “I can get the best deal because I have X,” or, “I help grow my portfolio companies by X” to get the ball rolling. Be wary of saying that the amount of money you have is your strength — at this stage, your bank balance isn’t your competitive edge. Focus instead on what makes you unique, credible and relevant. Having a high number of strategic contacts, extensive industry experience or a backsheet of successful exits could be your secret ingredients. For extra guidance, check out this resource my team put together to help fund managers consolidate their niche in an “investment thesis.”

Once you have a list, choose your top three strengths and write a followup sentence detailing how each of them can be enriched by your network and expertise. Ideally, share these with a test group (friends, family or fellow entrepreneurs) and ask them which is the most compelling. If there’s a general consensus toward one point, you know to make that a large chunk of your VC fund’s thesis.

Do you have a solid network?

Who you know is just as important as what you know, and the most prominent VCs tend to be in the middle of a flow of information and people. Your network tells founders that you’re respected and reassures them that they will probably be brought into the fold to connect with future mentors, customers, investors or hires.

If you’re a thought leader, the alumni of a well-known company like Uber or PayPal, or if you’ve started a community around an emerging vertical, you’re more likely to form a positive deal flow. But this status and these relationships have to be established before you launch your fund — if you try to network from zero, you’ll be spinning too many plates and won’t have the social proof to back yourself up.

Don’t just rely on your gut to tell you whether your network is satisfactory. Map out your personal ecosystem, sorting people based on familiarity (close contacts or acquaintances) and defining characteristics (consumers, finance, ex-CEOs, etc.). That “map” can be as basic as an Excel sheet with a column for each category, or you could use more attractive visual tools like Canva — great for sharing with your future team and encouraging them to fill any network gaps.

What size fund do you want to launch?

A VC fund runs like any other business — you have to develop a vision, recruit a team, form an entity, raise money, deliver value and report to stakeholders. To kick things off, you need to consider what size fund you want, and then secure significant commitments from LPs — at least 10% of your total fund. LPs can be corporations, entrepreneurs, government agencies and other funds.

Also keep in mind that most LPs will want you to personally invest at least 1% of the total fund size so that you have “skin in the game.”

For that reason especially, it’s best to start small, somewhere between $5 million and $20 million, and use this “training fund” to demonstrate returns and create a launchpad for bigger raises to follow.

Can you help founders from launch to exit?

Your partnership with companies will be for the long haul, so you can’t rely just on offering value when you wire the money. Founders need consistent support across the full startup lifecycle, meaning you need to be conscious not to overpromise and fail to deliver. Think of the startups you’d most like to work with: How could you help them now? How could you help them in the future? And how could you help them exit?

You can take a skills-centric approach, where you reserve different resources and connections based on marketing, hiring, fundraising and culture-creation that can be applied as the startup grows. Alternatively, you might want to make sprint-like plans, where you check in with founders on a repeating basis and iterate the support you offer based on their progress. Whatever way you chose to structure your support, ensure that you’re realistic about what you can bring to the table, your availability, preferred involvement and how you’ll document it.

The future of VC will be driven by venture capitalists with strong values who have built funds with the new needs of founders in mind. VC may once have been exclusive and mysterious, but 2021 could be the year VC becomes a more open and fair space for businesses and investors alike.

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Autonomous aviation startup Xwing hits $400M valuation after latest funding round

The safety pilot has his hands off the controls during an Xwing demonstration flight. Image Credits: Xwing

Xwing has scored another win two months after it completed its first gate-to-gate autonomous demonstration flight of a commercial cargo aircraft. The company said Thursday it has raised $40 million at a post-money valuation of $400 million.

The company is setting its sights on expansion — not only tripling its engineering team, but eventually running regular fully unmanned commercial cargo flights.

Xwing has been developing a technology stack to convert aircraft, including a widely used Cessna Grand Caravan 208B, to function autonomously. But it’s had to solve a few problems first: “the perception problem, the planning problem and the control problem,” Xwing founder Marc Piette explained to TechCrunch. The company has come up with a whole suite of solutions to solve for these problems, including integrating lidar, radar and cameras on the plane; retrofitting the servomotors that control the rudder, braking and other functions; and ensuring all of these are communicating properly so the plane understands where it is in space and can execute its flight.

The company has already performed close to 200 missions with its AutoFlight system. For all these flights, there’s been a safety pilot on board. In addition, a ground control operator sits in a control center and acts as a go-between from the autonomous aircraft to the human air traffic control operator.

“We don’t anticipate automating [communication with air traffic control], trying to do natural language processing and having a computer make the response to the air traffic controller,” Piette said. “For safety critical applications, we don’t view that as a useful path…but what we do, though, is we have a ground operator in our control room that just talks to air traffic control on behalf of the aircraft. So for the air traffic controller, it’s seamless. As far as they’re concerned, they are just talking to a pilot onboard the aircraft.”

Image Credits: Xwing

For its autonomous flight activities, the company has authorization from the Federal Aviation Administration to fly under an experimental airworthiness certificate for research and development that was expanded in August of last year to include a special flight permit for optionally piloted aircraft (OPA).

The company is looking to eventually remove the safety pilot, but only once full safety redundancies are in place, Piette added. That includes redundancies across all sensors and computer systems. Fortunately for all of us that fly, commercial aviation safety levels are extremely high. It means a high airworthiness standard for aviation startups. Smaller Class III aircraft like the ones Xwing is targeting must demonstrate a risk of one catastrophic failure per hundred million flight hours.

Xwing’s activities have garnered attention from investors. This most recent funding round was led by Blackhorn Ventures, with participation from ACME Capital, Loup Ventures, R7 Partners, Eniac Ventures, Alven Capital and Array Ventures. Including this round, the company has raised $55 million in total capital.

The autonomous flights are only one part of Xwing’s business activities. It’s also been flying manned commercial cargo operations under a contract with a large logistics company signed December 1.

“We set up what’s effectively an airline,” Piette said. By modifying these aircraft with sensors to collect data, Xwing is able to feed this valuable flight time into a training algorithm, and collect other useful data, such as how often the pilots communicate with air traffic controllers and the types of directions the craft receives.

Looking ahead, the company will be significantly scaling its workforce over the next 12 months, in addition to increasing its commercial operations in parallel. On the technology side, Xwing is looking to fly autonomous commercial cargo flights, with a safety pilot onboard, under an experimental ticket and exemption from the FAA. The company will likely reach this milestone also within the next 12 months, Piette said. After that, it would look to remove the safety pilot from the aircraft. Even then, the company would still need to get its systems certified to completely remove any constraints on its movements in airspace.

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Tecton teams with founder of Feast open source machine learning feature store

Tecton, the company that pioneered the notion of the machine learning feature store, has teamed up with the founder of the open source feature store project called Feast. Today the company announced the release of version 0.10 of the open source tool.

The feature store is a concept that the Tecton founders came up with when they were engineers at Uber. Shortly thereafter an engineer named Willem Pienaar read the founder’s Uber blog posts on building a feature store and went to work building Feast as an open source version of the concept.

“The idea of Tecton [involved bringing] feature stores to the industry, so we build basically the best in class, enterprise feature store. […] Feast is something that Willem created, which I think was inspired by some of the early designs that we published at Uber. And he built Feast and it evolved as kind of like the standard for open source feature stores, and it’s now part of the Linux Foundation,” Tecton co-founder and CEO Mike Del Balso explained.

Tecton later hired Pienaar, who is today an engineer at the company where he leads their open source team. While the company did not originally start off with a plan to build an open source product, the two products are closely aligned, and it made sense to bring Pienaar on board.

“The products are very similar in a lot of ways. So I think there’s a similarity there that makes this somewhat symbiotic, and there is no explicit convergence necessary. The Tecton product is a superset of what Feast has. So it’s an enterprise version with a lot more advanced functionality, but at Feast we have a battle-tested feature store that’s open source,” Pienaar said.

As we wrote in a December 2020 story on the company’s $35 million Series B, it describes a feature store as “an end-to-end machine learning management system that includes the pipelines to transform the data into what are called feature values, then it stores and manages all of that feature data and finally it serves a consistent set of data.”

Del Balso says that from a business perspective, contributing to the open source feature store exposes his company to a different group of users, and the commercial and open source products can feed off one another as they build the two products.

“What we really like, and what we feel is very powerful here, is that we’re deeply in the Feast community and get to learn from all of the interesting use cases […] to improve the Tecton product. And similarly, we can use the feedback that we’re hearing from our enterprise customers to improve the open source project. That’s the kind of cross learning, and ideally that feedback loop involved there,” he said.

The plan is for Tecton to continue being a primary contributor with a team inside Tecton dedicated to working on Feast. Today, the company is releasing version 0.10 of the project.

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Greylock GP Mike Duboe to discuss how to scale your company at TechCrunch Early Stage in July

While the money flowing into Silicon Valley is reaching historic heights, the competition for getting customer attention and growing businesses is still a major challenge.

At TechCrunch Early Stage: Marketing & Fundraising, we’re diving into the topic of growth and scaling and bringing in experts across the startup landscape to share what they’ve learned in the pilot’s seat. We’re thrilled that Greylock General Partner Mike Duboe will be joining us in July to discuss what’s hot and what’s next for growth in consumer and B2B technology.

Before joining Greylock and being promoted to his current role as a GP, Duboe led growth at Stitch Fix as the company built out its online styling empire. Previous to that, Duboe was the first growth hire at Tilt and has had stints on YC’s growth advisory council and as a growth lecturer at Reforge.

Duboe’s interests as an investor have centered on commerce infrastructure, marketplaces, creator tools and more, with investments in no-code visual editor Builder, SMS marketing platform Postscript and online wholesale marketplace Vori. We’ll chat with Mike about where he advises founders to focus their efforts and how to make the most of budgets across channels.

Tickets for TC Early Stage: Marketing & Fundraising  are available at the early bird rate which gives you an instant $100 savings if you book before May 1!

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Casa Blanca raises $2.6M to build the ‘Bumble for real estate’

Casa Blanca, which aims to develop a “Bumble-like app” for finding a home, has raised $2.6 million in seed funding.

Co-founder and CEO Hannah Bomze got her real estate license at the age of 18 and worked at Compass and Douglas Elliman Real Estate before launching Casa Blanca last year.

She launched the app last October with the goal of matching home buyers and renters with homes using an in-app matchmaking algorithm combined with “expert agents.” Buyers get up to 1% of home purchases back at closing. Similar to dating apps, Casa Blanca’s app is powered by a simple swipe left or right.

Samuel Ben-Avraham, a partner and early investor of Kith and an early investor in WeWork, led the round for Casa Blanca, bringing its total raise to date to $4.1 million.

The New York-based startup recently launched in the Colorado market and has seen some impressive traction in a short amount of time. 

Since launching the app in October, Casa Blanca has “made more than $100M in sales” and is projected to reach $280 million this year between New York and its Denver launch. 

Bomze said the app experience will be customized for each city with the goal of creating a personalized experience for each user. Casa Blanca claims to streamline and sort listings based on user preferences and lifestyle priorities.

Image Credits: Casa Blanca

“People love that there is one place to book, manage feedback, schedule and communicate with a branded agent for one cohesive experience,” Bomze said. “We have a breadth of users from first time buyers to people using our platform for $15 million listings.”

Unlike competitors, Casa Blanca applies a direct-to-consumer model, she pointed out.

“While our agents are an integral part of the company, they are not responsible for bringing in business and have more organizational support, which allows them to focus on the individual more and creates a better end-to-end experience for the consumer,” Bomze said.

Casa Blanca currently has over 38 agents in NYC and Colorado, compared to about 15 at this time last year.

“We are in a growth phase and finding a unique opportunity in this climate, in particular, because there are many women exploring new, more flexible job opportunities,” Bomze noted. 

The company plans to use its new capital to continue expanding into new markets, nationally and globally; as well as enhancing its technology and scaling.

“As we continue to grow in new markets, the app experience will be curated to each city — for example, in Colorado you can edit your preferences based on access to ski areas — to make sure we’re offering a personalized experience for each user,” Bomze said.

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Sales scheduling platform Chili Piper raises $33M Series B funding led by Tiger Global

Chili Piper, which has a sophisticated SaaS appointment scheduling platform for sales teams, has raised a $33 million B round led by Tiger Global. Existing investors Base10 Partners and Gradient Ventures (Google’s AI-focused VC) also participated. This brings the company’s total financing to $54 million. The company will use the capital raised to accelerate product development. The previous $18 million A round was led by Base10 and Google’s Gradient Ventures nine months ago.

It’s main competitor is Calendly, started 2 1/2 years previously, which recently achieved a $3 billion valuation.

Launched in 2016, Chili Piper’s software for B2B revenue teams is designed to convert leads into attended meetings. Sales teams can also use it to book demos, increase inbound conversion rates, eliminate manual lead routing and streamline critical processes around meetings. It’s used by Intuit, Twilio, Forrester, Spotify and Gong.

Chili Piper has a number of different tools for businesses to schedule and calendar accountments, but its key USP is in its use by “inbound SDR Sales Development Representatives (SDR)”, who are responsible for qualifying inbound sales leads. It’s particularly useful in scheduling calls when customers hit websites and ask for a salesperson to call them back.

Nicolas Vandenberghe, CEO, and co-founder of Chili Piper said: “When we started we sold the house and decided to grow the company ourselves. So all the way until 2019 we bootstrapped. Tiger gave us a valuation that we expected to get at the end of this year, which will help us accelerate things much faster, so we couldn’t refuse it.”

Alina Vandenberghe, CPO and co-founder said: “We’re proud to have so many customers scheduling meetings and optimizing their calendars with Chili Piper’s Instant Booker.”

The husband-and-wife-founded company was fully remote from day one, with 93 employees in 81 cities and 21 countries, long before the pandemic hit.

John Curtius, partner at Tiger Global said: “When we met Nicolas and Alina, we were fired up by their product vision and focus on customer happiness.”

TJ Nahigian, managing partner at Base10 Partners, added: “We originally invested in Chili Piper because we knew customers needed ways to add fire to how they connected with inbound leads. We’ve been absolutely blown away with the progress over the past year, 2020 has been a step-change for this company as business went remote.”

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