Editor’s note: This post originally appeared on the Unusual Blog.

Today, Unusual Ventures is thrilled to announce that we have partnered with Arrikto to execute on its mission to overcome the barriers that keep data science teams from quickly implementing machine learning initiatives in production environments. We are pleased to lead their $10M Series A round.

Arrikto introduces an enterprise-grade version of Kubeflow, the leading Kubernetes native platform for data scientists and MLOps teams who want to rapidly and reliably deploy data models into production. Arrikto’s solution empowers data scientists to seamlessly move models and data from laptop to production and fully realizes the automation potential of an enterprise grade MLOps solution. Arrikto’s assets — MiniKF, Kale, and Rok — fill key gaps that exist today in a standard Kubernetes and Kubeflow installation to help companies get models to market faster, more efficiently, and securely. In effect, Arrikto helps companies manage “Data as Code” — an approach that gives data teams the ability to process, manage, consume, and share data in the same way we do with code for software development. Data science teams are no longer burdened with needing to learn infrastructure technologies or native cloud configuration strategies. With Arrikto, a powerful model that used to take months to deploy and benefit from can now be pushed into production in minutes.

The Unusual Team was first introduced to the Arrikto Team via one of our successful founders, Spiros Xanthos, and we were immediately impressed by two things. First, the founders, Constantinos Venetsanopoulos and Vangelis Koukis, stood out as an extremely talented group of technologists and were some of the brightest minds in cloud infrastructure and data science that we’ve come across. Not to mention, it was hard to look past the team’s perseverance and dedication to the problem they were trying to solve — they had largely bootstrapped the company for a period of years when they could have taken more lucrative jobs. It was clear they had assembled a team that truly believed in their differentiated approach and long term vision. Second, we shared the belief in the emerging market opportunity to provide the leading cloud native solution to empower data scientists to deploy models into production with a Kubernetes native foundation. Arrikto has assembled a toolkit that meets data scientists where they are building models and makes the transition to the MLOps teams frictionless. Data scientists are empowered to do what they do best — focus on experimentation — and MLOps teams can deploy and manage models in production with the leading cloud native infrastructure technologies.

A big reason the Arrikto team was eager to work with Team Unusual was our hands-on approach to early stage company building, specifically in the form of our Get Ahead Platform (GAP). Our GAP Team has been working closely with the Arrikto team to help build an adoption-led go-to-market strategy and we’ve been impressed with their hunger to learn and willingness to put in the work to become the industry-standard platform for MLOps automation.

As data science becomes more and more valuable and the ability to put that data into action continues to be what separates market leaders from the rest of the pack, any company — regardless of size — should have access to the tools that will help them build a great business. The Unusual Team believes the Arrikto team is well on their way to breaking down the technical barriers to democratize machine learning capabilities in the enterprise. We’re excited to see what’s in store for this innovative team and are humbled to be partners with them on this journey. Onward!

Read more about Arrikto’s Series A announcement from TechCrunch

Learn more about how to set the right goals, approach the right investors, and craft a winning pitch in order to raise your seed or Series A round

Arrikto — Unlocking the Acceleration Potential of Machine Learning Ops in the Enterprise was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on the Unusual blog.

Earlier this year, we launched our completely redesigned website that was built on one non-negotiable principle — “Founders First.” At the heart of this redesign was our Field Guide, which decodes the best practices of the most successful entrepreneurs and packages their learnings in an innovative way to help founders win. Though we were humbled by the positive feedback we’ve received from founders, we set the goal to consistently improve our offerings in order to continue delivering on our mission — raising the bar for what early-stage founders can expect from their venture partners. Today, we are excited to announce the launch of our brand new Founder Portal.

The Unusual Ventures Founder Portal can be thought of as “mission control” for our portfolio founders, where they can go to get the resources they need. Specifically, we designed our Founder Portal to help Unusual founders:

• Access recommended vendors and exclusive discounts via our Partner Program
• Revisit exclusive content from our Unusual Academy sessions, Insight Series, and more
• Learn about upcoming events and advanced deep-dives with industry experts
• Get to know the entire extended Unusual family in our private community directory

We understand early-stage founders are busy. Our goal in creating this portal was to make the onboarding process as seamless as possible for new Unusual founders joining our portfolio and to give them access to all of the support and resources they need in one centralized place. We are pleased with the feedback so far:

“As a startup with a grand mission in a competitive space, we appreciate that we can rely on the tight network Unusual Ventures provides via its internal team and fellow founders. The Founder Portal enables us to pick the best partners at the best terms based on recommendations from people we trust. That’s invaluable for a company at our stage.” — Till Pieper, Co-Founder and CEO, CoScreen

“There’s a lot of thought leadership in the startup world but very little on the tactical day-to-day. How do you run a board meeting? How do you actually make the offer to a potential hire? The Unusual Founder Portal has put resources together in a way that’s easy to digest and discover exactly what you’re looking for as an early-stage founder.” — Dennis Xu, Co-Founder, Mem Labs

As with the website redesign, we know our work isn’t done yet and will continue to seek out new ways to innovate and better serve early-stage founders. To our portfolio founders, thank you for selecting us to be on this journey with you. We look forward to making the portal better with your input. For other early-stage founders, we’d love to hear from you to get your input on what kind of resources would be beneficial to you as you get started on your journey — reach out!

Onward!

Check out the Unusual Field Guide, which provides founders with all of the best practices and tools you need to solve the most challenging early-stage problems

Introducing The Unusual Ventures Founder Portal was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on the Unusual blog.

Today, Unusual Ventures is excited to announce that we will be continuing our partnership with portfolio company Vivun to further execute on its mission of unlocking the strategic potential of presales in the enterprise. We are thrilled to participate in the company’s $18M Series A financing in partnership with Accel.

Vivun, the creator of the first software platform specifically designed for presales teams, Hero by Vivun, transforms the way B2B companies go to market. Hero leverages the strategic potential of presales, which consists of sales engineers, solution architects, or Field CTOs — i.e. the people at a company with technical backgrounds who understand the product from the functional level and can explain the details to both the user and buyer. In addition to providing sophisticated tools for Presales management, Hero keeps product and sales teams aligned, identifies in-demand product features and automatically alerts salespeople when new product releases could bring opportunities back to life.

We first met the Vivun team after learning about the solution from the Presales team at Harness, where our Unusual co-founder Jyoti Bansal is the CEO. We were intrigued by the passion surrounding how intuitive Vivun’s product is, its ease of use, and its ability to greatly improve productivity across the entire company by unlocking the knowledge within the Presales organization. The potential and buzz around the product had our full attention, but then we met the incredibly talented management team and realized we were onto something truly unique. The four founders — Matt Darrow, John Bruce, Dominique Darrow, and Claire Bruce — all brought distinct skill sets around product, operating, sales, and marketing to the table. Matt and John also understood the pain they were trying to solve firsthand based on their experiences running the Presales teams at Zuora and SignalFx. It was clear to the Unusual Team that the Vivun Team was creating an exciting new market opportunity and there were no other products out there quite like it.

Since the Unusual team made the seed investment in Vivun and began working with the team less than a year ago, we have witnessed tremendous progress. Vivun has cultivated 600% growth in ARR and doubled their customer base, including enterprise customers like Autodesk, Dell SecureWorks, and Okta. The Vivun team has also tripled in size adding notable positions to scale the company, such as a VP of Sales, VP of Marketing, and Chief Data Scientist. As if these updates don’t speak for themselves, the team is also a joy to work with, humble, and incredibly hard working — important attributes the Unusual team looks for in our portfolio partners.

We believe the Vivun team is onto something special and are carving out a new category. The Unusual team is excited to tackle the next leg of the journey with Team Vivun and are excited to see what’s in store, as this is certainly just the beginning. Onward!

Read more about Vivun’s Series A announcement

Learn more about how to overcome obstacles founders face going from seed to Series A

Vivun — Empowering Presales Teams to be the Heroes of the Enterprise was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on the Unusual blog.

Compliance audits are painful, manual, and time-consuming, yet are critical business processes. Though audits happen year after year, research shows more than 70% of CISOs are struggling through the process due to poor tools, conflicting priorities, limited resources, and now, in the era of COVID-19, remote management. Today, Unusual portfolio company, Shujinko, is continuing to pioneer the automated audit preparation process with the launch of two critical products: AuditX™ and the industry’s first Automated Evidence Collection Engine on the AuditX platform.

By launching the AuditX platform, Shujinko is reinventing audit preparation, evidence collection, and readiness with purpose-built software. Specifically:

• AuditX simplifies, automates, and modernizes enterprise audit preparation
• Makes audit preparation 3x faster, simpler, and delivers 360 degree visibility
• Eliminates the current painful, manual, and time consuming process that still relies on shared spreadsheets, scripts, back and forth email, etc.

Customers like Delta Dental, Oomnitza, mParticle, Kloudio, and independent audit firm partners are already seeing the value of the AuditX platform. Here’s what Erin Coburn, Director of Cybersecurity Delta Dental of Washington, had to say about the value of the AuditX platform: “The first pass at SOC 2 compliance is always the hardest, and Shujinko offered guidance on both engineering best practice and the cloud compliance particulars. Without a tool like AuditX, we would have had to deprioritize SOC 2 compliance because it just wouldn’t have been achievable given the volume of work on our plates.”

The second piece of Shujinko’s product announcement is their Automated Evidence Collection Engine on the AuditX platform, which automatically crawls and collects evidence directly from AWS and Azure cloud native infrastructures. With the push of a button, Shujinko’s Automated Evidence Collection Engine collects technical evidence, including encryption of data at rest, encryption key management, network segmentation and configuration, and provides the results in a formatted .pdf report. The engine’s extensible, scalable, and robust architecture automates security and compliance to match the speed and iterative nature of modern cloud development. By automating these activities, valuable engineers and DevOps resources are freed up to work on critical priorities versus spending time manually capturing screenshots for audit preparation.

Shujinko’s co-founders, Scott Schwan and Matt Wells, keenly understand how painful cloud compliance audits can be, as they worked to solve this issue for Starbucks, an early adopter of the cloud. The Unusual Team believes they are the right team to solve this compliance issue and are one step closer to achieving their vision of automating the painful audit process with these key product innovations.

Congratulations to Scott, Matt, and the Shujinko team! Onward!

Read more about Shujinko’s AuditX™ and the industry’s first Automated Evidence Collection Engine on the AuditX platform

Shujinko — Simplifying, Automating, and Modernizing Audit Preparation was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on the Unusual blog.

Since its inception, cloud computing has polarized IT experts, with many early adopters extolling its value and traditionalists sounding the alarm on security concerns. However, embracing cloud solutions has become increasingly important for the enterprise as we’ve witnessed a massive evolution in how we build, deploy, and run applications, which includes the rise of containers, serverless, and the move to microservices. In addition to technology shifts, COVID-19 has forced enterprise companies to quickly rethink and adapt how they do business — from the way they manage their now fully remote workforces, how they sell their products, and more. Cloud platforms and cloud security are no longer nice-to-haves in the COVID-era, and companies are left scrambling to figure out what services and operations they need to shift to the cloud and how they can protect their data across a distributed workforce.

Tim Prendergast, founder of Evident.io, is a long time supporter of the cloud and has helped guide iconic companies’ cloud strategies, such as Adobe and Palo Alto Networks. We recently sat down with Tim and Noah Carr, Unusual Partner with a focus on enterprise infrastructure and security, to discuss how the cloud ecosystem has changed over the past decade, how the pandemic has impacted cloud adoption, the biggest opportunities for startups entering the cloud security space, how startups should think about their GTM approach, and more.

Can you give us a little background on yourselves?

Tim: I’m a career technologist who has spent a lot of time in the technology operations and cybersecurity space. For the past 10 years, I’ve been playing a lot with cloud infrastructure — since the technology’s inception — originally as an end-customer at Adobe, where we built one of the most recognizable cloud transformations. Based on that experience, I co-founded Evident.io, and built out a category in the cloud security space that led to a great exit to Palo Alto Networks. I was Palo Alto Networks’ first Chief Cloud Officer and helped them transition focus to the cloud with a series of acquisitions and moves that have set them up to be one of the largest cloud security providers out there.

Noah: I joined Unusual Ventures earlier this year with a focus on enterprise — more specifically, I spend most of my time in enterprise infrastructure and security. Prior to Unusual, I co-founded a fund at Point72 focused on early stage enterprise infrastructure and security. Before Point72, I spent 5+ years at Bain Capital Ventures, where I similarly worked closely with the enterprise infrastructure and security entrepreneurs that we invested in and supported, including Tim.

How has the cloud ecosystem changed in the last 10 years?

Tim: Honestly, it’s been amazing to watch this industry evolve over the past decade. In 2010, we were just toying with AMIs on early AWS EC2 services. Now, 10 short years later, we have fully encapsulated, distributed, fault-tolerant containerized services available and no-code application building technology. I think we’ve really seen enrichment come in three ways: Native learnings from cloud providers that feed their innovation, customer-side responsibilities being innovated and delivered by third party companies, and finally, the open source community improving and expanding the suite of tools and services that can be run on cloud by customers. There’s a more robust, richer set of tools and solutions that are purpose-built for cloud environments available, which is helping drive adoption and innovation inside companies.

Noah: The biggest change over the last decade is adoption — competitive enterprises need to move to the cloud and it’s evened the playing field with smaller companies, allowing them to ramp up quicker and have similar resources on hand to compete (when you consider the trends around AI/ML, remote collaboration, and SaaS.) On top of that, we’ve seen a massive shift from a development standpoint given the rise of containers, the move to microservices, the importance of being cloud native, and the amount of open source code used to build applications today. With all of these shifts in cloud infrastructure, we’ve had to rethink managing, monitoring, and security. From a business standpoint, the way we sell software has also changed. If you go back 10 years, most software was sold as a perpetual license. Today, subscription models are the norm. Additionally, a large amount of technology built today is delivered as a hosted solution versus on-prem.

Do you believe the global pandemic and with it, the accelerated shift to remote work has impacted the rate of cloud adoption?

Tim: I don’t think we’ll know for sure until numbers come out about a year from now. I’d look at the incremental peak of, “Oh my God, we have to do something in the cloud,” as temporary, while the long term transition will depend on how companies and organizations evaluate their performance and long-term view of the ecosystem. I have no doubt the pandemic will change the way we perceive the value and viability of a distributed workforce. I don’t know that it will be enough to push companies to give up their sunk costs in physical infrastructure, but early indicators may tilt my views. A good example is Pinterest. They just said, “Forget it. We’re going to pay $90 million and bail out of our 49,000-square foot SF office we built out, rather than move into it and have everyone come into the office.” They realized they could make their business work as is. I think we will see an uptick in the usage of SaaS services and the cloud-delivered solutions that Noah mentioned earlier, as well as remote security improvements — people will be dusting off their ancient VPNs and putting modern zero trust distributed access technologies in place to support their remote staff. Companies will adapt and find ways to support their staff in this new model that we’re all operating under. And a lot of that’s going to be either delivered from the cloud or natively run on the cloud by those organizations in the future. We just won’t know how big of a shift that is until next year when earnings for Amazon, Google, and Microsoft come out to truly understand how much money really poured into that investment that was otherwise going into buildings, tangible infrastructure, etc.

Noah: I think accelerating is probably the right word here. As we discussed, adoption was already happening, but now that adoption has picked up. To Tim’s point, we won’t know for another year or so whether this shift will be systemic. My guess is yes. Initially when the pandemic started, expectations were we’d be remote for only a few months — “We’ll just put a Band-Aid on it and figure it out later.” Now that the pandemic has persisted to the extent it has and we understand it will continue for the foreseeable future, I believe a systemic change is happening more broadly. This changes how we live, how we buy goods and services, doctors’ visits, exercise, etc. The number of things that are now going digital and need to be supported digitally end up pushing towards more cloud adoption. The way we work has obviously also changed — more collaboration, how we share information, and how we interact with customers, etc. And so, more of that development that may have initially been on-prem is going to have to be pushed to the cloud and all the laggards who were investing in more of that physical infrastructure will now be forced into a cloud world. Based on the conversations I’ve had with leaders — CIOs, CTOs, etc. — living in this COVID world, cloud budgets are expanding. Now that there is this forcing function and people can see that workforces are capable of effective remote work, we’ve started to see large organizations change — even to the extent of people expanding HR practices and thinking about hiring the right talent, expanding the scope of locations they’ll hire talent to get people with cloud experience. And, of course, this all has security repercussions.

Beyond cloud adoption, what are the largest technology market trends that you believe directly impact cloud security today?

Tim: I think the heavy leftward shift of security is a big one — it really does mean predictive security and engineer-driven security practices are becoming more normal and no longer fall into the “that’s not my job” bucket. I also think no-code application development and hosting part of cloud environments is going to be fascinating for security. Can the providers do it all as part of the service and totally abstract security from the customer? Can the third-party security companies get enough access to actually protect those abstracted workloads? We’ll see.

Noah: I completely agree with Tim. Most broader tech trends in some way impact the security market and we are seeing numerous shifts within technology. Look at AI and machine learning adoption and the work companies need to do with sensitive data and workloads in the cloud — it’s just how you stay competitive at this point. Combine that with automation, infrastructure as a code, a general shift to abstracting away infrastructure, and it means security teams have far less control. You lose control of your infrastructure and of what you traditionally think of as your resources. This equates to impacts on security — you don’t have the same visibility you did before and it’s significantly more difficult to manually go in and remediate issues. We are also leveraging a lot more open source technology today, which opens enterprises up to more vulnerabilities and again creates gaps in visibility. This is a huge shift in the market, how we think about security, the code that we’re using — especially if it’s not directly ours, and how we make sure that people don’t find vulnerabilities in what we’re trying to build today. The last piece is this massive trend around remote work and distributed teams. Those trends directly impact a lot of the things that Tim mentioned like how you think about your enterprise perimeter and what you need to do to protect your company as people work remotely.

Given this accelerated adoption and need for improved cloud security, do you believe the market is better served today by a new entrant standalone startup or is it more effective to have a larger platform provide a solution?

Tim: This is a really interesting dichotomy — the emerging startups are really pushing the envelope and trying to make something exponentially better than what exists in the larger platforms. At the same time, they are limited in scope and can’t satisfy all of a customer’s needs. The large platforms do a lot of things well, but often favor stability over innovation and serve the lowest common denominator customers instead of the real innovators. This drives the acquisition cycle we see so frequently — big tech company buys sexy startup to add their super cool capabilities to the larger platform. I personally like the startups because they are eager to listen and deliver solutions to customer pains. Each customer matters more to the startup. It really depends on the maturity of the customer — if they are a bleeding-edge innovator, startups will give them the best return on investment. If they are a technology follower or later adopter, they will do well to use their existing big platform relationships to just add the features they need to their existing commitments.

Noah: This has always been a challenge across our industry, platform versus stand-alone. To Tim’s point, there’s value to both. I’ve always believed where specialization is paramount and organizations have high priorities, it’s harder to trust the large platforms. It’s harder for them to effectively solve these more detailed and complicated problems because it’s not as core to what they do. And to Tim’s point, some of it depends on the organization. If they need to be on the bleeding edge and a startup has built a solution for them, it’s more difficult for them to go with a platform vendor. However, there will always be this “good enough” paradigm that exists within the market. When Tim and team started Evident, there were Inspector and Config Rules from AWS. But again, for the people who prioritized security — where the specialization mattered — they wanted to buy it from a company like Evident that had the expertise, knew how to build a tool that could be easily operationalized, and that came from founders who directly experienced this pain. Even after the first wave of cloud security companies, we still haven’t seen the cloud platforms put forth a competitive enough solution to fully satisfy enterprise needs. The place I see an opportunity is for HashiCorp. Given their position with Terraform and Vault they could potentially release an automated tool that is well integrated, provides effective visibility and could do some level of remediation.

Where do you draw the line between approaching the problem as a security challenge versus a broad engineering or QA challenge?

Tim: Personally, I believe that security has always been a broader engineering/QA challenge and that those departments just refused to acknowledge how much of their job it actually entails. My views don’t jive with big enterprise-land, though, and silos are a real issue. I’ve long advocated the DevSecOps approach where security is embedded in engineering. The ability to osmotically influence each other on a daily basis is a huge win for the organization and product, and ultimately, the end user of the product. If you want to have all domains represented in the quality of the final product, you’d better include them in the planning, preparation, and execution phases. Standalone solutions and the “toss it over the wall” methodology of security issues and remediations don’t work in these integrated process teams. The days of a job where you sit in front of a keyboard and monitor and “operate” these standalone solutions are long gone. Now teams need to — and in some cases do — use more heavily automated solutions and technologies to orchestrate, validate, and even remediate technology functions and issue management.

Noah: I absolutely agree. There’s so much you can do in terms of integrating into these broader engineering solutions, and leveraging APIs, existing tools, etc. It goes back to that initial “triple sale” challenge with selling application security. You’d sell security to the security organizations, but security would have to sell it internally to the developers and the operations teams. Now we’re seeing a lot of these lines blur with the rise of DevOps and DevSecOps — there is this broader convergence happening. And so — Tim mentioned it before — security is shifting left where it needs to, which means a lot more of this work can already be done or should be done and embedded into existing software development and CI/CD processes. Then, we can proactively fix a lot of these issues before they are ever pushed into production. It’s an alignment for those teams internally, especially now that the world is more application-centric, and developers are far more involved with this process. I think we continue to push down that road and it’s the right way to solve the issue going forward.

What are the security implications as a result of the rise of infrastructure as code?

Tim: I think there’s two sides of this coin — the positives and the negatives. The positive aspects are all pretty amazing. You get item import infrastructure, the ability to regenerate new complete infrastructures every time you deploy with no real penalty, and a truly identical dev test and production environment that your QA team can actually get a good read off of. Plus, like Noah said previously, you get what I call a pre-flight auditing of your infrastrastructure and the ability to verify everything is going to come out the way you expect it, so know that that you’re already in compliance and you’re already going to meet your security policy before you even push the button for deployment. Imagine getting the compliance done on an infrastructure template because they’re so accurate in how they portray your environment — it would be so painless compared to where we live today. On the flipside of the coin, if you can spin up 10,000 servers at the push of the button, you can make 10,000 mistakes with the push of a button with infrastructure as code. So, one wrong machine image attached to a template — say something that’s vulnerable to a known exploit — and you could deploy it to a massive infrastructure. It’s really difficult for humans to detect those errors because there’s just too many parameters and components in the infrastructure out there to manually examine. An attacker could potentially find and exploit a mistake at scale before the operational staff and their systems detected it in this type of edge case situation. Similarly, exfiltrating data and data loss can happen on a monumental scale — it’s really easy to kick off a recursive copier back off a large data store and improperly secure and store the results. We saw this with the big S3 exposures in Amazon years ago where someone would mark a tick box in the UI and explore 100 million peoples’ motor information, for example. It touched all of us, no matter if we know it or not in this country, and it touched a lot of people around the world in the same way and can have powerful repercussions. I think the power of declarative infrastructure templates and the pre-flight auditing to secure environments far outweighs the risks, as long as we live in a world where the carbon-based life forms can keep their dirty appendages off the keyboard long enough to let the system do its job, because most of those issues are totally human-inspired and human-led.

Noah: Yes, there’s absolutely a challenge. The existing ways that we try to solve these problems are still manual, and there are people with hands on keyboards trying to fix things. Infrastructure automation is a wonderful thing, but to Tim’s point, you can make massive mistakes, it can explode out of control very quickly and you have far less visibility into all of your infrastructure resources. However, there are now easier ways to solve these problems leveraging automation. With infrastructure as code you’ve been able to simplify environments and make them far more efficient. Automation comes with a lot of responsibility and that means that people need to adapt to it and leverage solutions that integrate closely with those new solutions to make sure that it remains secure.

As the market becomes more application-centric does cloud security need to shift left and be more embedded in CI/CD? Developer-centric?

Tim: Yes. Yes. There’s no more to be said other than: YES — IT’S ABOUT TIME PEOPLE.

Noah: Yes. At this point, security teams are setting the guard rails. And then the onus is on the development team or DevSecOps professionals. Historically, devs cared primarily about deploying code, not making sure it was secure. Now we have that convergence and we need to continue to push in that direction, especially as we abstract away infrastructure and backend work. Developers can continue to focus on building applications. We just need to embed security in that development process, so security doesn’t become a blocker.

How does this market shift change how startups in this market should think about their GTM approach?

Tim: I don’t think they should change their go-to-market approach a lot, but I think they should reevaluate a bit. Startups in this market should be heavily selling to the pain-bearers — those who are suffering most and stand to reap maximum benefit from your solution. Just because somebody could buy your product doesn’t mean that they understand the intrinsic value of what it will mean in their day-to-day if they were to have the product. Selling the true value of what you have as a product is key to the right people, specifically how you can tie it in and amplify the value of what they already have and how you can free up human brains/hands to do more important work goes a long way to getting into the door with organizations. Everyone is competing for the same human resources, the same budget. You really have to differentiate in what makes you the best partner for the organization or customer and how you’re going to make their lives better in very short order. The days of one-year long proof of concept evaluations and things like that are long gone. You got days or weeks to prove that you have the best technology to solve their particular issue. And if you can’t do that, they’re not going to talk to you again for two or three years until the life cycle passes by. You have a very short window in which to very quickly demonstrate value, find the champion inside an organization, and then get them to become a customer. And now, you have to do all of this remotely in the COVID-19 era. So, it’s really an approach that no longer depends on taking people to lunch and having these long in-person meetings, but more focused on can your company and its products stand on their merits and actually do really well inside these organizations?

Noah: Even before we hit the global pandemic companies were selling less and less top down. The world is becoming more developer-centric — developers have far more power within an organization to make the decisions around buying different technologies like security, especially as we see the convergence around DevSecOps. Now, it’s more about getting broader adoption and to Tim’s point, getting people excited about what you’re building. My suggestion would be to think about what you can open source. How can you leverage that open source to drive adoption and iterate on a solution that solves an acute pain? For example, can you show some level of cloud resource visibility early on? By finding that beachead use case and wedge that you can give away for free, you’ll be able to drive adoption and build a strong community of developers and security professionals who love you. That community can guide your product direction for years to come by telling you where the pain is most acute and which features really matter to build next.

What do you think the biggest opportunity is for startups entering the space?

Tim: I think it’s the same as it has always been — the biggest opportunity is to innovate on the groundwork laid by your predecessors. There’s unrivaled computing power, data storage capacity, and network capacity at your fingertips. How do you reframe the problem statement and use infinite infrastructure capacity to unwind the legacy mess that has been left at most organizations? How do you get butts out of those legacy seats and put them in the driver’s seat of innovation? Don’t think about how you do X better than the incumbent — think about how your ability to do that is unlocking new opportunities for the people who embrace your product. I think that’s really the mindshift difference that will make a big change in cybersecurity. We see a lot of startups in cybersecurity that are basically feature companies — the idea that’s a one-trick pony. And they raise money and then they never go anywhere specific as a scaled company because they run into walls where they’re not contemplating all the problems a customer has and they’re not a platform. I think that’s a dead end approach from the beginning. In order to build companies that truly scale and solve mass customer issues, we need much more thought going into what problems we’re solving, rethinking the questions we’re asking about security, and truly innovating with this new power at our fingertips that we didn’t have before.

Noah: Tim is exactly right. So many people — especially in security — build these features for a singular problem that they see, but don’t take the next step of asking, “What does that grow into? How do I leverage that into a broader platform?” I see the opportunities to build better visibility in and control of your cloud resources. Additionally, I think there needs to be a next generation of IAM that really understands who is accessing what, who is allowed to access what, and when they can access. Most existing solutions today I’ve seen don’t even come close to the granularity needed to effectively solve the current IAM problem. Largely, technology that is application-centric, plays into this DevSecOps convergence, and continues to shift security left, I believe will have a leg up going forward. It’s all about adoption. As Tim mentioned, a lot of these feature-based companies fall down because they’re just never operationalized internally. Sometimes they’re able to sell and get that early traction around the space, but what builds a longstanding company is the ability to understand who is using your technology and make them successful. So much of it is having the right UI/UX today. So, how do you make sure that it’s operationalized internally? Continue to be dynamic and iterate on customer feedback, figure out what’s need-to-have vs. nice-to-have, what is the next piece that fits into this platform puzzle, and adapting your longer-term product vision as you go along.

For more on technologies that are pushing the enterprise to embrace cloud solutions, read our white paper on serverless computing

State of Cloud Security — Q&A with Tim Prendergast and Noah Carr was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: Welcome to the Unusual Founders Spotlight series! The goal of this series is to introduce the founders in our portfolio who have the rage to master and are currently building the future across categories and industries. This post originally appeared on the Unusual blog.

As technology advances each year, so does the amount of data that is generated by users. Internet users generate about 2.5 quintillion bytes of data each day and in 2020, every person will generate 1.7 megabytes of data each second. The quality and ability to analyze this data is critical to today’s businesses, as it enables decision making and business strategy. Yet, the 560M global knowledge workers — financial analysts, product managers, middle managers, etc. — have no efficient way of accessing the data they need to help provide business insights. Today, the US economy loses up to $3.1 trillion a year due to poor data quality and 95% of businesses cite the need to manage unstructured data as a critical business problem. As the number of SaaS applications within the enterprise continues to grow, this problem will only become more prevalent.

For many companies, the current process to run an ad-hoc analysis on something simple like revenue from a specific product and region requires the business analyst to ask IT to query Tableau or Looker to create a report for them. Depending on the size of the organization and other priorities of the IT team, this can take days or even weeks. This bottleneck and dependence on IT engineers ends up costing companies valuable time and money to enable such basic queries.

Sathish Raju and Krishna Bhat, co-founders of Kloudio, experienced the distinct struggle financial and business analysts faced during their time consulting for various large companies, such as Oracle, SAP, and Capgemini. Both felt there had to be a more productive way for knowledge and information workers to access data and started to play with the idea of a connected spreadsheet that could extract data from any cloud or database. They quickly realized they were onto something and Kloudio, a spreadsheet-based application, was born. Kloudio enables financial analysts to automate routine processes and directly access data from multiple sources — such as Salesforce, Oracle, Netsuite, and more — all without involving the data engineering team. By eliminating the data middle man, Kloudio has greatly reduced inefficiencies and enabled financial professionals to be 10x more productive and saved their customers around $4–5M.

We recently sat down with Krishna and Sathish to discuss their vision for Kloudio, how they stay focused through the ups and downs of scaling a startup, the best piece of advice they’ve received on navigating challenging times like 2020, and more.

Unusual: Can you give us a little background on yourselves?

Krishna: I’m originally from Mumbai, India, and grew up in a middle-class family. It was quite competitive in Mumbai, but I was a decent student and got into a well-respected computer engineering college. Once I graduated, I joined Oracle Corporation in India as an engineer, which is actually where I met Sathish. In 2005, Oracle sent me to the US on a business visa. I liked the Bay Area so much that I decided to apply for a H-1B visa and came back to the US at the end of 2005. From 2005–2010, I worked at large consulting companies — like Capgemini and Fujitsu — where I was involved in various tech consulting projects, involving Fortune 500 companies like ADT Security Services, McDonalds, etc. As a Solution Architect, I would be involved in the overall global solution architecture for huge finance and product teams and first felt the pain of knowledge workers depending on data engineers to gather data in spreadsheets for their everyday analysis needs. After attending Columbia for business school, I joined Amazon as a product manager involved in international expansion projects and went on to lead the software subscriptions category for Amazon. Sathish and I kept in touch and spoke about the pain business analysts faced accessing various data sources via spreadsheets and the dependence on data engineers to do so. Sathish started working on this problem on the side and we’d come together to brainstorm ideas. We ended up winning the TechCrunch Disrupt Hackathon in San Francisco for another idea we had in 2011, which boosted our confidence and made us think that we could take the leap full time to focus on a startup.

Sathish: I grew up in Chennai, India, and was from a not so well-off family, so I had to struggle to get an education and degree. I was accepted into one of the prestigious institutions in India where I studied computer science and engineering. After graduating, I really wanted to continue my studies, but due to my financial situation, I needed to get a job so I joined Oracle and that’s where I met Krishna. After a few years at Oracle, I was thinking of my next step and was really interested in entrepreneurship. A chance to go to the US presented itself, so I thought, “Maybe if I go to the US, I can gain more contacts and do something better.” So I moved to the US around 2007–2008 and worked in consulting for enterprise software companies, specifically with Oracle, SAP, Salesforce, etc. I also worked at big corporations like Cisco, NetApp, and ADT, as well as very small firms. While consulting, I kept coming across financial analysts and business analysts — who were trying to get data out of various systems — struggling because they were always dependent on IT engineers. I started to think about a connected spreadsheet that could integrate with any cloud or database and import data directly into the spreadsheets. As Krishna mentioned, at the time, we were brainstorming a number of ideas, including this spreadsheet concept. We did a few TechCrunch hackathons together and kept coming back to the spreadsheet idea related to data analytics. Data was only growing and it was very clear we were on to something. One day, we wrote a LinkedIn article about our idea and that’s when the magic happened. A Senior Manager from Netflix came across our article and reached out, asking to see our demo. He mentioned Netflix was experiencing similar issues and he thought our product could help. We went to Netflix, demoed the product, and within a week, they signed up for 10 user licenses. Everything really took off from there. Shortly after, we joined the LAUNCH Incubator run by Jason Calacanis, and we soon had around 200+ paying customers. This year, we raised funding thanks to Unusual Ventures and we are well on our way to delighting our customers with some exciting new product launches as we continue to scale the company.

Unusual: Can you tell us more about Kloudio, your vision, and the problem you’re trying to solve?

Krishna: If I were to summarize Kloudio in one sentence, it’s like a spreadsheet interface to an e-SAS. We want to democratize data access for everyone, starting with financial analysts. Today, there’s a gap — all the data sources that are exploding (SAS applications, databases, etc.) are being managed by data engineers, but the business metrics are actually being calculated by financial analysts. We call this the “business insight gap” and we want to bridge this gap and make it really easy for end users (financial analysts) to not only get access to data, but have robust control in the spreadsheet interface at SL level without being dependent on data engineers.

Unusual: Talk us through the “aha” moment that made you realize you were on to something with Kloudio.

Sathish: When I gave my consulting customers the Excel add-on, it was clear they really saw value in it. They immediately started requesting new features. When we pitched Netflix and saw that they too were experiencing this pain point despite being a technology pioneer, we thought, “Okay, if Netflix is having this problem and nobody else has solved it and we have, we are on to something really great here that definitely has value.”

Unusual: What excites you the most about the potential of Kloudio?

Sathish: The potential of Kloudio is huge. We are not just providing access to data governance, but also adding data intelligence in the future. The intelligence component will make analysts smarter without working harder and that in itself is exciting for me. We see in all our demos that customers are excited about what we are building and what this means for their business.

Krishna: The potential really comes down to the user: we’re creating an interface for all the knowledge and information workers who want to be more productive, especially when it comes to data. Data is being created more and more everyday from all the apps and devices we’re using, and Kloudio delivers the potential to harness all that data to provide intelligence to the end user in a way that is easily consumable. If you think about it, a spreadsheet is the closest thing to a programming language that everybody understands, and we want to make data accessible for people who are comfortable with spreadsheets like financial analysts. We want to make data analytics as easy and accessible as a Google search. The prospect of accomplishing that vision is truly exciting and keeps us going through the ups and downs of building a startup.

Unusual: What has been the biggest challenge you’ve experienced getting Kloudio up and running? How did you overcome this challenge?

Krishna: Hiring has been one of the biggest challenges we’ve faced. Getting a solid team together simply is not easy, especially in a competitive environment like Silicon Valley. Founders tend to underestimate how challenging this can be. We’ve had to do so many interviews and even after raising money, it’s still not easy. Fortunately, Unusual Ventures has really helped us find talent through its Get Ahead Platform (GAP), which we are so grateful for. Your company is only as good as the people you hire.

Sathish: When you start a company, it’s only the founders and you have to figure out how the company is going to grow and get funding. These are all challenging initial tasks, but we were lucky in that we had some market validation from the very beginning. We had some big wins in terms of customer validation so we could focus on other areas that presented bigger challenges like hiring. When you talk to people at bigger companies like Facebook, Twitter, Amazon, etc., they hesitate joining a company like Kloudio that is so early on. Hiring and convincing experienced people at these larger companies has been a challenge, but one we’ve welcomed.

Unusual: Starting a business can be overwhelming with everything you need to get done. How do you stay focused?

Sathish: Frankly, this journey is a bit of a rollercoaster ride. Some days, you are so high and some days, you are so depressed. Despite the ups and downs, it’s so important to stay focused on the end goal by taking care of the other areas of your life. I’ve found I need to carve time out for my family, health, creating a daily routine, taking time for myself, etc. Personally, in the evenings I try to go for a walk or cook. Cooking helps me relax. Channeling some time into things like cooking and spending time with my family helps me to balance the day-to-day stress I face building Kloudio.

Unusual: What is the biggest tip that you would give aspiring entrepreneurs who are just starting out on their entrepreneurial journey?

Krishna: Talk to as many potential customers to get feedback on the product as possible. You need to validate the product as much as possible before building the product. Actually talk to customers and then build. If it’s an enterprise product, build designs and mock-ups, show them to customers, validate that it’s in the right direction, and then build. This will help save you a lot of time. Also, be prepared to be very persistent — it takes more time to do a lot of things in the startup process than people estimate, such as fundraising, hiring, etc.

Sathish: A startup is a long journey and you need to have a compatible partner to help you run the business, just like we have compatible partners in life. Make sure you have a co-founder you trust, can lean on, and completely rely on no matter the time of day. I can’t stress enough the critical role a cofounder plays in your entrepreneurial journey.

Unusual: What is the biggest tip that you would give entrepreneurs in terms of fundraising?

Krishna: Sathish and I had probably 75–80 investor meetings. You need to be prepared to hear “no” a lot. However, if you believe in the product, you have good customers, and believe in the team and yourself, trust the process and really use the feedback you receive to make improvements. We received almost 70 rejections before we received our first term sheet. But that one term sheet turned into four term sheets within a week. Grit and persistence are so important.

Sathish: For me, I can’t stress enough the importance of having early customers for many areas of scaling your business, but especially for fundraising. Get customers to start using your product in production and give you feedback — even if they don’t pay for it. The feedback you receive will be a big plus when it comes to fundraising because the first question you will face is, “Who are your customers?” Even in the early stages, VCs are very cautious and want to know how your product will resonate with customers. It is very key to VCs to see you have some customers and that you have a bigger vision. When we started pitching, we quickly realized we needed to have an answer to what Kloudio will be in five years. Ask yourself, “In five years time, where do you see your company?” And be ready to explain your larger vision during the fundraising process.

Unusual: Getting a startup off the ground is difficult on a good day, but this is especially the case with all the curveballs 2020 has thrown our way. What has been the best piece of advice you’ve received about leading during this unprecedented time?

Krishna: For me, it was the advice to stay focused on making sure that current customers are happy, so that they are renewing and expanding. It’s easier to expand with a current customer than to get a new customer during a crisis. We are fortunate that our product is necessary and very applicable for a business, no matter what the temperature of the world is — a business needs data and software to help make better decisions, even if you’re going through a period of layoffs and cost cutting.

Sathish: I’ve read this and heard from many people that a time of crisis is also the best time to focus on the product. In a time like this, you may not win many new customers, but you do have a lot of time to focus more energy on the product itself. For us, we are turning this time into an opportunity and are focused on building product capabilities that our customers have been requesting.

Learn more about how Kloudio is democratize data access for everyone

Democratizing Data: Krishna Bhat and Sathish Raju, Co-Founders, Kloudio was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on Unusual’s blog.

Today, Unusual Ventures is thrilled to announce that we have partnered with Traceable to execute on its mission to protect cloud-native applications and APIs from modern and evolving cybersecurity threats. We are pleased to lead their $20M Series A round.

Traceable, the only application security platform built on distributed tracing and machine learning, delivers end-to-end protection — from user to API to code — for cloud-native applications. “We felt the market desperately needed a modern approach to application security, due to the massive transformation application architectures, development methodologies, and operational processes have undergone over the last decade, and if there was one team to bet on to build a world class solution, this was it,” said John Vrionis, co-founder at Unusual Ventures.

Application security teams have been stuck protecting modern applications with solutions that were built for a previous era. Traceable brings development and security teams together to protect and monitor production cloud-native applications and investigate threats and vulnerabilities with drill-down, code-level analytics, and forensics. Driving these capabilities is TraceAI, Traceable’s machine learning technology, which is fed by distributed tracing data collected in real time directly from the application. This rich trace data enables TraceAI to continuously learn normal application behavior (even as code and APIs change) and immediately detect malicious activity when user and/or application behaviors deviate from this norm. The Traceable team is proud to announce that they have made their distributed tracing platform available as Hypertrace, an open source project freely available to the developer and ops community.

Traceable is founded by Sanjay Nagaraj (former VP Engineering of AppDynamics) and Jyoti Bansal (yes, that Jyoti — the founder and former CEO of AppDynamics, co-Founder and CEO of Harness.io, and co-founder of Unusual Ventures). Together they have assembled an incredible technical team and worked tirelessly over the past several months hand in hand with Unusual’s Get Ahead Platform (GAP), to prepare the company for exiting stealth mode. Bill Hodak, marketing partner at Unusual Ventures, said, “Together, we have developed the company’s messaging, created a phenomenal website, iterated to define the initial ideal customer profile, and put in place all of the demand generation operational infrastructure.”

Liam Mulcahy, director of sales GTM at Unusual Ventures, added, “In working with the Traceable team as their first head of sales via our GAP engagement, we were able to craft and execute their go-to-market strategy encompassing everything from setting up sales-tool infrastructure, outlining discovery questions, creating a sales deck, and establishing qualification stages, etc. Working with such a strong team allowed us to iterate quickly to find product-market-sales-fit, leading to closing our first paying customers and working with companies ranging from the Fortune 500, Cloud 100, FinTech 100, and 2020 Unicorn Class”.

This type of collaboration between Unusual and our portfolio companies was exactly what John and Jyoti envisioned when they founded Unusual and brought GAP to life. At Unusual we aspire to reinvent the early stage venture business by partnering with product visionaries, providing unprecedented levels of operational support, and concrete deliverables to advance the company through product-market fit. We’ve successfully done this with a world class team at Traceable and couldn’t be more excited for the impact this group will have on the ecosystem. Congrats team Traceable!

Read more about Traceable coming out of stealth from its co-founders

TechCrunch with more on Traceable’s vision and opportunity

Traceable — Protecting Cloud-Native Applications and APIs from Modern Cybersecurity Threats was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: Welcome to the Unusual Founders Spotlight series! The goal of this series is to introduce the founders in our portfolio who have the rage to master and are currently building the future across categories and industries. This post originally appeared on the Unusual blog.

The invention of the automobile started out as a simple technology that solved a transportation problem for people, but quickly came to dominate transit and many other elements of people’s lives around the world. To accommodate the growing popularity of cars, cities rushed to develop their infrastructure and planned their layouts based on this technology, leading to congestion and other issues. With the introduction of new technologies, such as car sharing, ride sharing, e-hailing, and micromobility, today’s cities and their needs look vastly different from the past, introducing the need for governments to quickly adapt in order to undo a lot of the damage that’s been done by building cities around cars.

Of these technologies, micromobility — a category of light-weight transportation designed for individual use, such as bikes and scooters — has generated a lot of interest in recent years. According to McKinsey, micromobility operators have attracted a strong customer base roughly two to three times faster than either car or ride hailing due to the speed of trips compared to car-based trips and the freedom of fresh air. Consumers aren’t the only ones benefiting from micromobility. The economics benefit industry participants — it’s a lot easier to scale up micromobility assets compared to car-based sharing solutions — and micromobility options are taking cars off of city streets, thus reducing congestion and creating sustainable transportation options for communities around the world. Though there are significant upsides to micromobility, the market also introduces new challenges for stakeholders, specifically cities and operators.

William Henderson, founder and CEO of Ride Report, built his career as an early employee at product-focused companies like Apple and Square. Upon leaving Square in 2013, William knew he wanted to start a company and decided to work on a market that he was deeply passionate about, which led him to micromobility. The moment scooter sharing started taking off in the US, William realized there was a new model for government regulation that would require new technology, and so Ride Report was born. Ride Report, a solution that empowers cities with tools to help them make transportation more equitable, efficient, and sustainable, has monitored more than 100,000 unique vehicles in 2020 alone and has partnered with over 70 cities worldwide to help prioritize people-friendly communities and a robust transportation system built for everyone.

We recently sat down with William to discuss his vision for Ride Report, leadership insights he picked up from Jack Dorsey as an early employee at Square, and why his team is his biggest inspiration.

Unusual: Can you give us a little background on yourself?

William: My background is in engineering, but I didn’t actually go to school to be an engineer. I studied math and philosophy in school and graduated without many of the skills needed to be in the tech industry. Early in my career, I was particularly drawn to Apple due to its product-centric nature and managed to find my way there after a lot of pounding on the door. At Apple, I realized I wasn’t a big company person at all, but this experience was really important for my growth — I saw what it was like to build a great product, and most importantly, had the opportunity to work on a team that not only sweat the details, but was constantly thinking empathetically about the user. Around the time I was ready to start looking for my next opportunity, I was lucky enough to meet Jack Dorsey and hear about Square when the company was still operating out of his apartment. Intrigued by the idea, I joined Square as one of its first engineers and led the mobile team that delivered the original credit card acceptance and point of sale applications on iPad. Pretty soon after launching these apps, Jack had me spearhead the consumer division, which I ran until I left in 2013. This division acted like a company within Square and gave me a lot of core startup experience, as well as relevant domain knowledge around payments, data security, and data privacy that has proved to be valuable at Ride Report.

Square was the classic, crazy startup ride. We went from 10 to 1,000 people in three years and faced a lot of challenges in a difficult product space. By the time I left, I knew that I wanted to start a company and whether I liked it or not, this was who I was — leading a team and building products. But I also understood that if I was going to get back on the crazy startup rollercoaster, it had to be for a mission that I really cared about — something that was core to what I believe and what I want to fight to have exist in the world. That’s what led me to the micromobility market. I was in this place where I wanted to work on something, but I didn’t know what the product idea was. I picked the market first, which is a little bit unusual. I didn’t say, “Oh my gosh, I have this brilliant insight into micromobility.” Micromobility didn’t exist at the time. I picked a market I knew I cared about, built things, and hung out with potential customers. Basically, I just dwelled in that market for a while before I really figured out what I wanted to do. I like to say I was in the right place at the wrong time. I found if you are willing to wait around in the right place long enough, your time will come. And that’s exactly what happened. As soon as we saw the emergence of the new dockless models, scooter sharing, and bike sharing in China, we knew that this was our calling and micromobility was going to be really important in this country. We didn’t predict the actual form factor — that definitely caught us by surprise — but the moment that scooter sharing started taking off in the US and we saw a new model for government regulation, we knew that this was our big moment and we jumped on it. At that point, we had a few customers and a small team, and we were able to just go after the opportunity full throttle.

Unusual: Can you tell us a bit more about Ride Report and its mission and vision?

William: If you look at where we are as a society, we have one mode of transportation — the personally owned car. The car started out as a simple technology that solved a critical problem for people, but it quickly came to dominate transportation and many other elements of our lives. Making and selling cars became an economic tool for our country and building the infrastructure that cars run on has had a massive impact on how our cities are laid out and what our foreign policy looks like. Today, cities have a very specific set of problems they are trying to solve. They’re trying to undo a lot of the damage that’s been done by building everything around cars and create cities that are more people-centric. Cities are also trying to combat congestion and the fact that automobile infrastructure really doesn’t scale past a certain point. The energy efficiency of a car will never be that great because you’re driving around two tons of metal just for one person, which makes them a major driver of climate change.

At the very highest level, Ride Report is trying to help cities imagine what their infrastructure should look like in the 21st century. We want to help cities take back control of their streets. We believe that transition has to happen independent of whether Ride Report exists, but our goal is to accelerate that evolution by giving cities smart API-driven tools to regulate micromobility. Through Ride Report, cities are able to regulate with a lot more control, but also in a way that’s much more efficient for the micromobility companies. These same tools capture revenue, so that cities are able to finance maintenance and reallocation of space to more efficient modes of transportation. This is a huge problem right now where every city is facing a crisis because they rely on the gas tax. The gas tax is going to drop off a cliff as vehicles are electrified and become more fuel efficient. Additionally, the gas tax has a lot of strings attached and doesn’t allow cities to really have complete autonomy in terms of how they re-imagine their cities and their streets. Our mission is to accelerate the transition to a more sustainable, equitable, and efficient transportation system.

Unusual: Did you always know you wanted to be an entrepreneur and when did you know you were ready to start your journey?

William: Yes and no. I’ve always been someone who just creates products. Even before I really knew what I was doing, I was making things. I remember releasing products when I was just sitting around in high school. No one used them, but I made them anyway. I made websites for each product I created to try and emulate the companies that I admired. But I didn’t know I wanted to start a company until I was leading a team at Square. One of the biggest things I learned from Jack Dorsey and will always remember him saying to me is, “You’re a product person — you can’t change that. But you can’t stay as involved with the product as you are right now. If you’re going to scale as a leader and scale this team you’re leading, you’ve got to be able to step away.” He taught me to think about a company or team that you’re leading as a product. What are the inputs and outputs? Who is using it? And what can you do to use that same attention to detail and empathy to improve the environment of the team, how it’s structured, and the processes it uses to communicate and collaborate? That really stuck with me and by the time I got done at Square, I had some pretty specific notions for how I wanted to run a company differently from Square and what that would look like.

Unusual: What has been the hardest aspect of entrepreneurship that nobody warned you about or that you just were not expecting?

William: The hardest thing is staying out of react mode. When you first get started, it’s a good thing to react to everything because you’re still learning and the team is really small. In those early days, the quicker you can respond to a new opportunity or a new challenge, the better. But as you start to scale the team and vision and go out to fundraise, you’re suddenly not just thinking about what you’re doing tomorrow and next week, but need to think months or even years out. You can’t stay in react mode. As a founder and a team leader, you need to make that transition pretty early in order to spend your time more intentionally and be really thoughtful about what you need to do, even when nobody is asking for it. What do you need to do right now to make sure you can be where you need to be in six months or a year down the line? I’ve put a lot of systems in place to help me plan. As an example, I treat my calendar as a product, which is another thing I learned from Jack. Jack would have one day a week where he just focused on marketing, one day a week where he just focused on products, and another where he just focused on the team. I don’t do exactly the same thing, but what I took from his exercise is that he’s very intentional about designing how he uses his time — he didn’t just let his calendar fill up and then hope that it was the right stuff. I also do a lot of writing for myself. Some of it I share, some of it I’d never share, but I start off every single week with that practice and think about my goals for the company and myself. What do I view as my job? What are the responsibilities of my job and how would I rate myself in each of those responsibilities today? This exercise helps me gain a sense of what’s most urgent, not in terms of what’s the loudest thing I can react to right now, but what’s the most pertinent when it comes to where I want to be or where I want the company to be at the end of the quarter and at the end of the year. Each week I plan my week around that objective or set of objectives. Taking this time every week has been a grounding and powerful exercise — it puts me in a totally different mindset for the rest of the week.

Unusual: Who is your biggest influence or inspiration and why?

William: My employees. We are a very values-driven company and put everything we believe and how we are upholding these beliefs into a public handbook. Anyone who is interested in applying to the company ends up reading it and it usually is a major reason why they apply. Then they show up and start looking for ways to make the company even better. And a lot of the time, that means doing things that I never would have thought of or asking me to do things better in a way I might not have done on my own.

After both of our fundraising rounds, I shared our term sheets with the company. Obviously, it was very exciting to have a term sheet, but the team went off and started kicking the tires. They started by looking at the investors’ websites, who else they invested in, what they care about, and how they put what they say they care about into practice. I love that they didn’t just say, “Ooh, we have a term sheet!” Instead, they said, “Is this good enough for us?” It really was awesome — both times they came back and said, “Wow, these investors are amazing. We didn’t even think there were investors like this out there and they chose us.” Both times were incredible moments — to feel like I had such good alignment between what I cared about, what the team cared about, and what our investors cared about. This team really is a huge source of inspiration and growth for me.

Unusual: What is the biggest tip you’d give aspiring entrepreneurs just starting out in their journey?

William: I have a different tip depending on which stage of the journey they are on. If they are really just starting out, don’t have a team, and maybe don’t even know which market they are in yet, I suggest keeping a list of ideas. I call this list “the shelf”. Every entrepreneur is different, but someone who is a product-centric entrepreneur like myself probably already has a list they’ve been keeping. At some point they’re going to decide, “Hey, I want to start my own thing.” The first week after I left Square, I took my list and decided to build one idea every week for eight weeks. At the end of each week I reevaluated to see if I wanted to keep working on the idea. If I didn’t want to, I started another idea the following week. This method works for me because it’s always clear after a week if I’m excited about something. If the idea feels like it has potential, I keep working on it and if after a week I’m not excited, I give myself permission to start something else and maybe pick back up on the idea further down the road. By proceeding this way, I have found you go with whatever idea has momentum and lo and behold, a lot of times the thing that has momentum for you will also get other people excited.

Unusual: What’s your biggest fundraising tip?

William: My biggest tip is to tell a story and start with yourself. When I was first preparing to raise money, I was so intent on making the case for the business and the market opportunity that I forgot to tell the story about why I’m so passionate about what we’re doing at Ride Report, who I am, and what I value. It turns out that at an early stage, your story is going to be the most compelling part of your pitch to investors. At the early stage, you haven’t figured out all the other stuff, but if you can get an investor to see through your eyes and share your passion in the first 20 minutes of the meeting, it’s so much easier to get through the rest of your pitch. And if you do get through the rest, you know you have an investor who actually cares about your mission and shares some of your values or your passions versus someone who just sees a big financial opportunity. It took me a while to get this right.

To be honest, I think I was perhaps intentionally avoiding speaking about why I was so passionate about this market and why it mattered so much to me. When I started in this space, there was no market, but I still went for it. Most investors were not paying attention to micromobility during this period and even in the summer of 2018 (when we were pitching) there was a lot of skepticism. At some level I was also worried that investors would see my passion as a liability — that I would be seeing the world as I wanted it to be rather than as it was. Because of these concerns, I was really intent on trying to prove the market opportunity and led with this in my pitch versus leading with my passion and dedication to the market. However, once I made the switch to leading with my story and passion, I saw a huge difference.

Learn more about how Ride Report is making micromobility work

Making Micromobility Work: William Henderson, Founder and CEO, Ride Report was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s note: This post originally appeared on the Unusual blog.

Adding a partner is a significant decision in the life of any growing team. At Unusual Ventures, it is not enough to just be a great investor or operator, our team and our culture demand that you put founders and the team first. Kevin Compton, someone I am proud to call a mentor, once counseled me: “When you add a partner, you’re going to ask yourself a million questions. But at the end of the day, there is one question that matters most: Are you proud to introduce this person as your partner?”

At a time when the world could use more positive news that brings people together, we are excited to announce that early stage founders have a new world-class executive available to help. Today we are extremely proud to introduce Sarah Leary as our newest member of Team Unusual.

We started Unusual Ventures with an ambitious mission to reinvent early stage venture capital and build a firm that would raise the bar for the entire industry. Building anything of importance starts with people and a shared set of values. Sarah is a tremendous entrepreneur and human being, having co-founded Nextdoor, one of the most important and successful consumer technology companies in history. A former collegiate national champion in lacrosse, Sarah has a long history of competing and winning. She’s a master practitioner when it comes to building and growing community-driven businesses and she joins Unusual with a passion to share all her lessons learned with the next generation of founders.

Our team met Sarah and immediately connected over our shared vision to provide an unprecedented level of support for entrepreneurs and our mission of greatly improving many of the entrenched dynamics in the venture capital ecosystem. When we walked her through our approach to provide founders with hands-on help via the Unusual Method, it resonated with her desire to roll up her sleeves and get in the trenches with founders in the early years of their journey. Equally important, she wholeheartedly embraced our intentional approach of working for HBCUs, hospitals, and foundations as LPs because she shares our passion for creating value for institutions that will help make the impact we want to see in our communities.

Sarah will partner with Andy Johns to continue to build out our consumer practice and will focus specifically on investing in opportunities that tap into the power of community, marketplaces, and social networks. She also will work with Andy to scale the consumer side of our Get Ahead Platform (GAP) and Unusual Academy. Sarah is a product and company builder, and will be a fantastic coach and partner for founders.

We could not be more proud to say we are shoulder to shoulder with Sarah Leary. The venture capital community just got a whole lot better with Sarah in the game and we can’t wait to see the impact she will have on our founders and the industry more broadly.

Onward!

Sarah shares why she’s excited to join Unusual

Forbes with more on Sarah’s move to Unusual

Welcoming Sarah Leary to Team Unusual was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.

Editor’s Note: Welcome to the Unusual Founder Spotlight series! The goal of this series is to introduce the founders in our portfolio who have the rage to master and are currently building the future across categories and industries. This post originally appeared on the Unusual blog.

Presales — known by a variety of different titles, such as Sales Engineering, Solution Consulting, etc. — is a crucial, but often overlooked function in enterprise companies. There is an outdated perception that presales is the “demo team”, yet over 30,000 companies around the world employ presales professionals to support sales in closing business via their technical expertise. In fact, Harvard Business Review recently found companies with strong presales capabilities consistently achieve win rates of 40–50% in new business and 80–90% in renewal business.

Despite the data that points to the benefits of strong presales support, there’s a surprising lack of technology built for this crucial business function. Matt Darrow and John Bruce, two of Vivun’s co-founders, felt this pain personally as they were building the presales organizations at their prior companies, Zuora (now NYSE: ZUO) and SignalFx (now Splunk). Frustrated by the lack of tools designed specifically for presales, they recognized there was an untapped market with a significant opportunity at hand. While armed with deep domain and engineering expertise, Matt and John understood getting a company off the ground would take more than a great product. They would need to tackle sales, operations, and making customers successful. To pull this off, they had to look no further than their partners, Dominique Darrow, who built and ran the global customer success and support teams across various products at Google, and Claire Bruce, an IP litigation specialist and prior general counsel for a large multinational footwear and apparel company. Together, they founded Vivun, the first platform designed specifically for presales. Vivun enables presales teams to scale their organizations, distribute insights across their companies, and drive alignment between sales and product management. Founded in 2018, the company has quickly added fast growing startups like Harness, pre-IPO unicorns like Seismic, and billion-dollar publicly traded enterprises to its list of customers.

We recently sat down with Matt, John, Dominique, and Claire to talk about their vision for Vivun, what it’s like to start a company with your spouse, their advice for aspiring entrepreneurs, and more.

Unusual: Can you give us a little background on yourselves?

Matt: I studied mechanical engineering at Berkeley and went on to get my Master’s at UCLA. While conducting research and writing software that simulated the heat distribution across server racks, I thought, “This isn’t for me.” From there, I decided to focus more on business and joined Deloitte as a technology consultant. I really enjoyed understanding how technology could be used to change the way companies operate and sought ways to move from the delivery side to the front end of the process. That desire led me to my first job as a sales engineer at BigMachines, which was Godard Abel’s company (one of Vivun’s initial investors) over 10 years ago. At the time I wasn’t quite sure what a sales engineer was, but being the technical expert coupled with a company’s strategic advisor was an alluring role. During my time at BigMachines, I witnessed more and more companies struggling with new, subscription-based pricing models. That experience led me to Zuora, the emerging platform to run a subscription company, which would become the dominant business model of our time. From Zuora’s Series B to IPO, I built out the global presales organization and then went into product management, running two of their four product lines. I knew I always wanted to start a company one day and after Zuora’s IPO, I had some time to step back, refresh, think about a big challenge I personally experienced, and recruit an amazing founding team to make it happen.

Claire: I studied Biology at UC San Diego and then attended Law School at Santa Clara University because of their robust Intellectual Property program. Initially, I thought I wanted to specialize in patent prosecution, but it turns out that was a little dry for me! Expanding my focus to IP generally allowed me to work on a variety of matters with a diverse portfolio of clients. Immediately out of law school I lead discovery efforts on major IP litigation cases. While I found litigation invigorating, I knew that I wanted to work directly with a company in-house to make a greater impact. For the last seven years, I was General Counsel for a multinational company, handling all facets of their legal work. I helped Vivun with their legal matters when the team first began building the company, and as the volume of customers quickly increased, taking over the operational matters was a natural progression.

John:

After pursuing a degree in computer science at UC Irvine, I immediately dove into software engineering at Broadcom working on their Peoplesoft ERP platform, followed by Panasonic Avionics where I helped prototype next generation in-flight entertainment systems. Neither of these roles really seemed to fit, but I eventually managed to join Pandora (now Sirius) as one of their first 10 software engineers. I was able to couple my love of music with my career, move back to the bay area and tackle some really cool problems with an amazing team. But something still wasn’t quite right. I had, for all intents and purposes, my dream job, but still felt like my calling might be elsewhere. So I started looking for a role that would allow me to stay technical and get closer to customers at the same time. This search culminated in joining FreeWheel Media (now Comcast), a video advertising platform, as their first Sales Engineer. The second step on my Sales Engineering journey was Zuora (NYSE: ZUO) where I first crossed paths with my co-founder Matt. Together we led different parts of the presales organization, and the challenges we faced together planted the seeds for what Vivun would ultimately become. I eventually joined SignalFx (now Splunk) and led Presales, Customer Success, Customer Support, Professional Services, and Training from Series A to the acquisition by Splunk. Matt and I reconnected when he asked me to test an early prototype of Vivun with the SignalFx team. When I saw, first hand, the impact the product could have on a Presales team, it was a no-brainer for me to join Vivun.

Dominique: I studied economics at the University of California, Berkeley, which led me to my first career in finance. Straight out of college I was lucky enough to work with some amazing people at an ultra-high net worth brokerage firm and then at Standard & Poor’s before realizing the finance industry wasn’t for me. I landed my first job in tech at Wildfire, a social media marketing startup on the peninsula. The company’s tight knit culture and creative drive on it’s growth journey was inspiring to say the least and I never looked back. I then landed at Google for 5+ years, where I worked on multiple products and built out their customer success teams. When Matt shared the idea for Vivun, it just felt right to pivot back into a smaller company where I would have the opportunity to build a team and culture from the ground up.

Unusual: You all have different areas of expertise. How has that helped as you’ve gotten Vivun off the ground?

Claire: I consider us to be a puzzle with all the right pieces. We’ve struck a balance that is so unique. Matt and John have 20+ years of experience in product and engineering and have such an innate understanding of the presales function. John is incredibly forward thinking and Dominique knows how to work with customers so well. I handle all the operational day-to-day gritty things and ensure we are in the best possible place from a legal perspective for future investments and data privacy.

Matt: There was no accident in terms of the team we’ve assembled, which allowed us to bootstrap the company for the first 12 months. We didn’t take the strategy of one person coming in with a deck and idea, raising a bunch of money, and then trying to build the core team. We wanted to build the team first and then prove we could execute. This team has the expertise to handle everything from corporate compliance, customer contracts, building and shipping the right products, closing business, and making those customers successful after we onboard them. The core team was able to achieve all of this before we ever raised capital.

Unusual: You are unique in that there are two married couples as part of the founding team. What kind of reaction do you typically get and how do you balance the professional with the personal?

Claire: The response nearly 100% of the time from people is that they don’t think they could ever work with their spouse! In contrast, we’ve found there’s no one else we would want to work with. Founding Vivun has given us the incredible opportunity to work side-by-side with the people we respect most. We have a kind of counterbalance, not only between the four of us, but the couples as well. For example, John is data-driven and I am skilled at consensus building. We’ve been able to work with each other to bring out each other’s strengths.

John: I think if our skill sets had overlapped more, it may have been harder. But again, coming back to the way that the team is structured, we don’t step on each other’s toes. We have definitely received questions about the team itself, but the proof is in what we’ve been able to execute on and achieve. Additionally, all of our eggs are in one basket, which answers the commitment question: we are all in and very, very invested in making this work.

Dominique: Reactions have varied from delighted surprise to disbelief, which is expected since our founding structure isn’t common. When you’re building a company, and a team in general, trust is super important, which makes this partnership ideal.

Unusual: Can you tell me more about Vivun’s mission and vision?

Matt: We’ve built the very first platform for presales, which is normally the second largest department in the enterprise behind sales. Other names for roles within this department include sales engineers, solution consultants, technical architects, solution advisors, and more. These professionals are the folks who are experts in technology and simultaneously support closing business. John and I intimately lived in this space for decades, with 20+ years of experience between us. Like our beginnings, most people stumble into presales and say, “I didn’t even know this was a thing.” Not only is it a thing, but the presales function is critical for technology companies. This function helps customers understand the technology, helps product managers prioritize roadmaps, helps business scale with efficiency, and helps salespeople figure out the best deals to pursue in their pipeline. Yet, there’s no technology available to enable presales to scale their operations, distribute their insights across the company, and ultimately, become a strategic business unit and not just the demo team. These are all experiences John and I lived firsthand. We came up with the idea for Vivun while at Zuora and felt we needed to make it a real platform, so every company with presales could capitalize on its value. We’re currently laser focused on presales because it’s a huge market opportunity in its own regard; however, presales is just step one towards our larger goal. From an expertise point of view, presales team members are half product manager (PM) and half sales rep (AE). The normal DNA of someone in presales is that they know the technology as well as the PM, but they’re out there selling and driving revenue every day. We recognize that the companies that are going to win in the next 5–10 years are the ones that are going to close the gap between the teams that drive revenue and the teams that build the products. The only group that’s going to make those worlds converge is the group that has a foot in both camps, which is presales. So for us, our ultimate vision will be to make one linear reality from product to sales.

Unusual: You often hear the glamorous side of entrepreneurship, but what about the flip side? What’s the hardest thing about being an entrepreneur?

Matt: Building a company is very different from building a product. That’s the thing about our journey — we’re here to build a great business. That means there is a lot more on our plate than engineering, for instance: Can we calculate our subscription metrics? Do we have compensation plans and payroll? Do we have an expense policy? Are we collecting on invoices sent to customers? How do we onboard and offboard employees? It’s the complete machinery of the company that needs to be put in place.

Claire: Working with your spouse means that you have to be really cognizant of not allowing work to consume you 24/7. It can and will when it needs to, but you need to carve out time to exist as a couple and have a conversation about your own bills and your own chores. But really, it hasn’t been a challenge yet because we’re all so excited and driven to make Vivun successful.

Unusual: On the flip side, what has been the most fulfilling part of being an entrepreneur?

John: A) Knowing that we created something that is helping customers demonstrably make their life and business easier, better, and faster; and B) people wanting to join us on this journey. It’s incredibly humbling when you realize that people are staking their livelihood on the success of this idea that we as a founding team are bringing to market. I can’t overstate how humbling it is to look over at Claire, Dominique, and Matt and just think, “Wow, this is something — we’re really doing this.”

Matt: The one thing that I would add that I’ve found particularly fulfilling is that we are a category creator. We’re not Slack 2.0 — we’re not any other tech company out there. We’re bringing something new to market that has only previously existed in John and my mind, and seeing people not only like it, but really benefit from the product, is extremely fulfilling.

Unusual: Is there anything you all wish you knew before you started on this journey of building Vivun?

John: As an early stage company, a big mile marker is raising venture capital. I thought I understood the process because I saw how the machinery worked at SignalFX. I quickly came to realize that I saw how a company raised capital from Series A on, but I had no idea how to get an investor to write that first check. I had a lot of people in my network who had successfully raised money and told us, “This is what it’s like. This is how you need to do it.” Turns out we were getting different advice from different people. Don’t get us wrong, we were super appreciative for all of the coaching we received, but we quickly realized everybody had their happy path that they spoke to us about. When we were going through the fundraising process and we weren’t on that supposed happy path, it was a little disheartening. I wish I had known prior to this first fundraising round that there simply is no happy path. Every company is going to be a little different and every founder will have their own journey. Oftentimes, what people tell you is kind of an abbreviated version of what the path actually looked like and the amount of effort that truly went into closing that round. If I had known that before, it would have made our fundraising process a degree or two less stressful.

Matt: I wish we had known we didn’t need to wait as long as we did before kicking off our fundraising process. We put a lot of onus on ourselves to prove out the business, which entailed getting the core team assembled, earning the first dollar, winning the first contract, having a GA product in the market with customers using it — all before raising funding. In some cases, we found this to be a detriment because we had more data points to discuss and investors wanted to draw out the process with much more diligence vs. founders who would say to investors, “I have an idea, I’m willing to bet on our team’s background, let’s go.” I also think if we had gone through the fundraising process sooner, we’d be six months ahead of where we are now because we could have hired more people earlier. I really thought we needed to have more of an ironclad ship before fundraising, which I’m glad we had, but at the same time realized we really didn’t need.

Unusual: What is the biggest tip you’d give aspiring entrepreneurs?

Matt: Pursue something you have personal experience with which you care deeply about. Don’t create a startup just because you want to be an entrepreneur. That might be trite, but I feel like that helped us during our fundraise. John and I have over 20 years of industry experience. We’ve lived the pain, we personally care about it, and it’s what we’ve built our careers on. It just so happens that we want to be entrepreneurs and there was a market opportunity. We didn’t sit there and say, “Hey, we really want to build a company. What is trending right now that we could go after?” Instead, we felt very strongly that we knew this problem better than anybody else and that’s what will make us successful in the long term.

Claire: When you lead with integrity, you build a team that aligns with your values. When that happens, you create a team that you love working with to build something you are proud of.

Dominique: Outline your ideal company culture at the very beginning and always work towards these goals. The values you define early on can be instrumental in how you build your teams, the policies you create and the overall motivations that can drive your company forward during the best and worst of times.

John: I was introduced to the notion of a pre-mortem recently. It essentially entails looking in the future to analyze the ways that your company can fail. From that plan, work backwards to ensure those scenarios never happen. What you’re trying to do is figure out any kind of existential risk to your company. It’s an exercise I don’t think a lot of people go through. If you do this exercise with eyes wide open and dig into all the inputs, you’ll get some really interesting answers. It makes you reconsider whether you should start a company at all. On the other hand, you might find that all the things that could go wrong are actually manageable and that you can put a plan in place to overcome any issues.

Learn more about how Vivun can help unleash the power of presales in the enterprise

Discover how the Vivun team raised their seed round and lessons learned

Presales Champions: Matt Darrow, Dominique Darrow, John Bruce, and Claire Bruce, Co-Founders, Vivun was originally published in Unusual Ventures on Medium, where people are continuing the conversation by highlighting and responding to this story.