On Setting Crazy Goals and Running Toward Them.

Yesterday was a pretty special day for the Lightspeed family.

In the morning, we announced the closing on $1.8B of committed capital for our new funds, Fund XII and Select III. And in the evening, we hosted our Annual “Leading Lights” Series at the beautiful SFMOMA, where my partner Ravi and I sat down with John W. Thompson, Chairman of Microsoft, and Bipul Sinha, Co-Founder and CEO of Rubrik, and discussed the good, the bad, and the ugly of building an enduring company.

The name of this event, “Leading Lights,” originated with our desire to celebrate leaders who have unique insights, not obvious ones. John and Bipul are the perfect embodiment of this. From West Palm Beach and Calcutta to Silicon Valley, John and Bipul spoke of their journeys to becoming CEOs, the importance of radical transparency, and why everyone should set crazy goals and run toward them.

Thank you to the over 200 entrepreneurs, founders, investors and friends of the firm who showed up last night and helped drive meaningful conversations and connections. It was one of those gatherings that will be easy to remember and tough to forget.

Below are some highlights from our conversations. If you are as passionate about entrepreneurship as we are and would like to attend our next “Leading Lights” event, send us a note with your LinkedIn profile to events@lsvp.com.

Q&A with John:

Tell me about growing up, and how your experiences and upbringing prepared you for a leadership role, whether CEO or Chairman?

• I grew up in West Palm Beach, Florida. My mom was a school teacher and my dad was a postal worker. They gave me the foundational pieces that structured my career. I learned from my dad the importance of focus and dedication. And my mom has a simple philosophy about life — it’s about life-long learning. That’s part of the reason I wanted to join Lightspeed as Venture Partner.

You spent 28 years at IBM. Let’s start there. Tell us about that?

• It was actually 27 years, 9 months, and 13 days…

What attracted you to the Valley?

• I thought software would change the world and wanted to be a CEO of a mid-size company. My wife and I had been married 6 months. I was about to be 50 and I thought if I really want to be a CEO, I might as well get on with it. I knew I wouldn’t be a CEO at IBM. I ran the software / biggest most profitable part of IBM. I wanted to make sure my dad knew about it before anything ran in the local paper. I told my dad I got a CEO job and he asked what is a CEO and what about your pension…

Symantec? What led to your success and tenure that led to 10X growth over a 10 year period?

• In the first three years, we went from 60/70% consumer to 60/70% enterprise and focused on how to scale from there. Veritas acquisition didn’t work well because I misjudged the cultural mismatch between the two companies. You should never dismiss cultural symmetry when evaluating a M&A opportunity.

So you went from CEO of a $6B company to a $6M company. What was that like? Learnings there?

• I never expected to take on the CEO role at VI. I asked another board member and he couldn’t do it because his wife was having health issues. I thought I might do it for a few years until we found someone else. After my first quarter there, we had our best quarter ever. So my view was, there’s no better time to go raise capital than right now. Lightspeed was the firm that said yes. That became the glue that caused me to stay. I would never walk away after raising money.
• As for learnings, when you go from something so big to so small, you can over-manage. You have to dial back your own point of view when you’re running a small company. Particularly when you’ve been around as long as I’ve been around.

That brings us to Microsoft…what major shifts did you witness?

• First step was cloud. True acknowledgement that the cloud was real. Second step. Focus on things other than Windows. If the company was going to sustain itself, it had to find another path.

Why Satya?

• We looked at a ton of external candidates and couldn’t find any that we really loved or that wanted the job. So we looked internally and Satya was the best candidate. What I didn’t know was just how emotionally connected Satya was to the culture of the company. He’d been there for 20 years and knew what worked and what didn’t work. He knew more than I did about the culture.

Why did you join Lightspeed? What excites you? Are you happy?

• I wouldn’t be here if it were not for you, Arif. And your relationship with Chris and Ravi. And everyone’s belief that my background and experience in the industry could be helpful to Lightspeed and your portfolio companies. I’m hopeful that I can find a couple deals and that will be validation of Chapter 4 of my career. (Chapter 1, IBM. Chapter 2, Symantec. Chapter 3, VI. Chapter 4, Lightspeed.)

Are you writing a book?

• I will never write a book!

Why not?

• Too focused on me. Sounds terrible. I guess my ego just isn’t big enough?

How should young entrepreneurs think about their roles in today’s world?

• Back in the day, people had more of a sense of loyalty to the company they joined. Turnover was minuscule compared to today. People in tech today have a stronger loyalty to their craft or their team within the company. There’s this notion today of creating a cohort of people that I know and love and like and respect and we all move from place to place together. Far more common today than it was 40 years ago when I started.

You serve on four boards. Two public and two private. Why?

• The answer on Microsoft is, I felt like it was in the same predicament as IBM circa 1990. I thought I could help Steve.
• At Illumina, it’s a business that I know nothing about. It surfaced right around the time that my sister who is two years older than me passed away from Alzheimers. This is a chance for me to learn about something totally different. In the spirit of life-long learning. I also coached the CEO throughout his career and couldn’t say no.
• In the case of private boards, it’s simple. I have capital invested. Any place that I put money, I’m more than willing to be an advisor but only in select cases will I consider being a board member. My dream with VI was to take it public. I hope to be with Rubrik when Bipul takes it public.

Q&A with Bipul:

How has being a VC influenced your approach to being a CEO?

• 90% of VCs don’t know what they’re doing. It’s critical to find a partner who understands the space and can help you think big.

Let’s take a step back. Can you tell us more about Rubrik’s work and mission?

• Rubrik delivers instant application availability to hybrid cloud enterprises for backup, recovery, search, cloud, & development. Our mission is to simplify how businesses around the world keep and use their data. Our goal is to build the next 20–30–40 year public company. We’re growing fast and thoughtfully. We’ve built the right leadership team and are focused on the people aspect of the business, which has served us well.

How did you find a product-market fit? How did you find early customers?

• When you start a company you need to have a thesis with a unique perspective about the market. But the source of truth is with the customer. You need to understand the customer’s pain and you need to understand how they perceive your product. Before we actually hired our first sales team, I had made 60 unique customer calls. You have to sell to believers in the early days.

How do you differentiate from your competitors?

• We’ve helped create a new market, bringing a fresh approach to a $50B market that hadn’t seen innovation in 10 years. When a new market is created, it attracts competition and big dollars. We’re proud to be the leading player in the space.

The arc for Rubrik is unlike anything we’ve ever seen in enterprise. You have a growth mindset. How do you think about growth?

• Many companies that I observed when I was a VC all had one key problem holding them back: nobody was actually making decisions. People were too terrified of a negative outcome. That creates a lack of an accountability within an organization and slows everyone down. While many startups boast that they can move fast, there are few that actually do. And in order to move fast, you need to be informed. That’s where transparency comes in.

Rubrik has made headlines for its “radically transparent” culture. Is it true that you invite the entire company (1200+ people) to your board meetings?

• Everyone — from junior level employees to senior leadership — is invited to attend the meeting via phone or in person. We welcome any employee to ask clarifying questions about where the business is going or ask a board member a question. In our view, encouraging management to show vulnerability and tackle uncomfortable questions makes for a better culture and better managers. The tone of these meetings isn’t “how do we make board members happy,” but rather, “how do we build a long-lasting company?”

What’s the thinking behind that? Has it ever backfired?

• Companies — large and small — suffer from poor information flow and lack of trust. Most employees tend to be in the dark and don’t know what’s really going on behind the scenes. This creates distrust and a culture of secrecy and exclusion. Employees want to work at companies that provide visibility. They want to work with executives that will bring them into higher-level conversations beyond the projects they are working on. The benefits of this approach are clear: If achievements and challenges are out in the open, everyone can align on long-term strategy and think at the business level.

Will that continue if/when you go public? How will you maintain a radically transparent culture at scale?

• Transparency will remain a key value at Rubrik. To build a long-term company you need to build trust. And trust comes from transparency. We believe our culture has greatly contributed to our hyper growth. We would not be here today had we adopted the typical approach of selective information sharing.

You’ve made some big hires recently — Jeff Vijungco from Adobe as Chief People Officer and Pete McGoff from Box as Chief Legal Officer. Hiring is a common pain point in this industry, maybe every industry. What’s your approach to attracting top talent?

• Yes. We’re thrilled to have Jeff and Pete on the team. They are here tonight. Please say “hi.” As I’ve said, Rubrik’s culture is our secret sauce. Jeff will be responsible for all aspects of employee success at Rubrik. He comes to Rubrik from Adobe. He helped scale the company culture as it grew from 3,000 to 18,000+ employees. So he knows a thing or two about growth. Pete joins Rubrik from Box where he served as its Chief Legal Officer and contributed to its successful IPO. At Box, Pete created a compliance framework to support customers from a broad array of verticals, including regulated industries. I think this was a significant differentiator for the company and can be for Rubrik. When it comes to attracting talent, many people come to Rubrik because they want to quickly make an impact. The tendency is, the bigger the company the harder it is to make your imprint on the product, the culture, the business.

So, what’s next for Rubrik? Are you going to IPO soon?

• I am focused on scaling Rubrik and building the next phase of growth for the company. We’re approaching a $300 million bookings run rate and have grown to 1200 employees across the world. Last FY we grew our customer base 4x YoY. My dream is for Rubrik to become an iconic 30+ public company.

Arif Janmohamed is a Partner at Lightspeed Venture Partners. He focuses on investments in enterprise IT and infrastructure and sits on the boards of a number of rapidly scaling companies, including Netskope, Qubole, Mist, Split, TripActions, and OverOps. In his free time, Arif plays ice hockey with his wife, who yells at him for never passing the puck to her.

Lightspeed is an early stage VC firm focused on accelerating disruptive innovations and trends in the enterprise and consumer sectors. Lightspeed has backed 300+ companies globally in the past two decades including Nutanix, AppDynamics, MuleSoft, Snap and Nest.