Did you ever see yourself being a venture capital investor when you were younger? I grew up the son of a child psychiatrist. I always knew he was a doctor but never knew what type of doctor until I was much older. I always remember when people would ask what I wanted to do when I grew up, I would reply, “work with people.” That was a very generic response, but fast forward to today, and that is truly what I do as a seed-stage investor. I underwrite and invest in people, and manage people/relationships/founder dynamics on a daily basis. Being a seed-stage investor is the closest you can come to working deeply with people and building trusted relationships. The success or failure of the companies we back is largely dependent on the people, and providing the resources to ensure alignment, execution, and having the ability to influence management and company strategic decisions depends on one’s ability to work intimately with the founders, CEO, board, and investors.
How does Spider fit in the crowded market of 100s of seed funds and dozens of traditional funds? Every traditional industry is being disrupted. So too is the venture capital industry. Dozens of venture firms which existed in the 1990s and 2000s have gone by the wayside, just like the Blockbusters and Xerox’s. A new generation of great firms have emerged. Many of the large firms due to fund size have moved up market. While no shortage of seed funds exist across every strategy and geography, we created Spider as a product with a singular focus around the digital transformation of industry (i.e. enterprise cloud software) based on insights we had as operators and investors, along with our unique strengths as enterprise founders and operators. Entrepreneurs select Spider as their first partner due to our track record building and investing in some of the most iconic enterprise cloud software companies, along with the high trust factor which is a core part of our operating DNA. And we are just getting started.
What aspects of your childhood had biggest impact on you? My father was always very persistent. Perhaps that was the New Yorker in him that rubbed off on me (I am a San Francisco native). As a founder, persistence and resilience in the face of countless obstacles and roadblocks is one of the key traits to success. Call it grit or a healthy disregard for the impossible. I remember wanting to be an investment banker out of college (all of my college friends went to work on Wall Street). I was rejected the first two times I applied to be an analyst. But I kept applying the following year and eventually received several offers at leading firms. Fast forward to today. Starting a company or a fund requires persistence and resilience. This is an attribute that we also probe deeply on before we arrive at an investment decision, to truly understand what drives and motivates the founders and how they have overcome past challenges. We love investing in founders with a chip on their shoulder or something to prove. Maybe they are an immigrant, were #2 at their last few companies and never had the recognition they deserved. Understanding the underlying drivers (why are you doing this) is critical.
What do you enjoy most about being an investor? Being an investor at the earliest stages of a startup’s formation is a true honor and privilege. I love listening to founder’s problems, learning about new markets that are ripe for disruption, and interacting and spending quality time with people. This is a people business. Having been an investor now for over a decade, one of the biggest joys is actually watching the founders we have backed grow into leaders of world-class companies, some of them now public.
How did you end up in venture capital? A lot of life is about timing, some luck, and of course hard work and persistence. I ended up in venture capital via a pretty fortuitous route. LiveOps had acquired my second startup. LiveOps was run by Maynard Webb, who had come out of retirement from eBay to lead LiveOps, one of the pioneering enterprise cloud software startups. It was April 2010. I had the privilege of getting an hour on Maynard’s calendar each month for a mentoring session (mentoring is a big part of what Maynard focuses on). It was during that session that Maynard’s early seed-stage investment in Admob was acquired by Google for nearly $1BN. Maynard decided he wanted to set up a family office to reinvest his family’s capital and asked if I would partner with him to create and run it. We partnered together for nearly five years with an amazing team before I spun out and launched Spider Capital in 2015. It was an incredible experience and I am forever grateful for the opportunity.
What are you most proud of at Spider? Well, we are literally just getting started. While we celebrated our five year anniversary in 2015 and have over 35 companies in the portfolio, one very meaningful early exit (Bonfire’s acquisition by GTYH), and two flagship seed funds with a world-class group of institutional LPs, we remain in the early innings of the digital transformation of industry, driven by AI-led enterprise software. I am really proud of our investment team and the impact they provide to our companies on a daily basis. The expertise they provide and coaching to the startups is really unparalleled for an enterprise seed-stage fund. I am also proud and humbled by the investors (LPs) who took a bet on me and Spider, especially having not come out of a traditional venture capital firm. Raising the first fund without a deep LP rolodex was one of the most humbling and challenging experiences. It makes you a lot more empathetic as well to the experiences founders go through with raising capital. The net is we have a lot of work to do, especially around driving meaningful returns to our LPs who have entrusted us with their capital.
What are the attributes you look for in founders? The most important attributes I look for in founders are vision, resilience, and integrity. Visionary founders lay the foundation for company culture and they naturally attract exceptional talent. Strong culture combined with exceptional talent will lead to successful companies. Being a founder means that you will almost certainly have ups and downs. Many successful companies emerged from hardships and challenges. I want to back founders who won’t give up easily. Last but not least, integrity is a very important attribute because it builds trust. Without trust, there is no meaningful relationship. Integrity means doing the right thing in the right way.
What does being a venture investor mean to you? Being a venture investor means listening to founders and helping them realize their visions. One of the first things I learned when I got into venture investing is that a venture investor is a kingmaker or queenmaker, not a king or queen.
What do you enjoy most about working in venture capital? I love listening to the founders’ stories and visions. I genuinely think this is the best part of my job. I feel very fortunate to have this incredible opportunity early in my career.
What are some of the questions you like to ask founders during your first meeting? So naturally, I often start first meetings with founders with “tell me your story.” I am eager to hear their full story from the beginning (often as early as childhood). I also ask “why” a lot, as it often elicits deeper and more engaging responses.
Where did you grow up? I grew up in Seoul, Korea before coming to the U.S. by myself to go to a high school in New Jersey. I had to adjust to a completely new environment and learned how to be independent and resilient. In that regard, I am highly sympathetic to immigrant and foreign founders and I believe in them.
How did you end up in venture capital? I studied Neuroscience in college because I wanted to understand how the human brain works. After college, I started my career as a management consultant at Bain & Company. It was an incredible two and half years of real world business training and learning managerial skills. I then joined NGP Capital, a global growth-stage venture capital firm where I focused on digital health and enterprise software. After two years at NGP Capital, I was connected to Michael and after five rounds of interviews, joined as the first investment professional at Spider Capital. It has been really rewarding helping build and scale Spider, and we are just getting started!
What do you enjoy most outside of work? I got into golf after moving to the Bay Area in 2016 (…after all, I had to take advantage of the nice weather!). The more I play, the more I realize that golf can be self-reflective and used to exercise introspection and learn about my nature and tendencies. Or maybe I just love socializing in nature for four hours – walking with others provides a great way of forming relationships.
What role are you most proud of in your career and why? The role I am most proud of is being the President of Zoom Video. We grew from $20M in ARR to over $400M in three years. The growth was amazing but even more important was our commitment to delivering happiness to our customers and employees. Our Net-Promoter Score was in the 70’s and employee turnover was less than 10%. Zoom does it right, if you take great care of your customers and employees they will take care of growth.
What advice would give to founders that are starting out? Be extremely hands-on with early customers and partners. These lighthouse accounts will help you fine-tune your product-market fit and are the glide path to scale. Conversely, if a customer leaves, it’s super important that you understand the root cause and what else you could have done to keep them as a happy, engaged, and paying customer. Churn is the silent killer in a recurring revenue business and customer success is everything.
Why did you become a Venture Capitalist after 20+ years as an Operator? I love working with intelligent founders that are solving difficult problems. My expertise is in Go-To-Market and I made a lot of mistakes over the years. It fires me up to have passionate conversations with entrepreneurs about the different ways to scale their Marketing, Sales, and Customer Success organizations. I have been in SaaS since the very early days and have seen it evolve and the cutting edge, early-stage startup is the most fun.
What was your first job in technology? My first job in technology was selling payroll and tax filing systems at Automatic Data Processing (ADP) in 1993. Our sales demo consisted of an MS-DOS based payroll application on a 15-pound Hitachi personal computer. The sales training was terrific but carrying the computer around in a full suit on hot summer days is something I don’t miss.
Matt is a seasoned operator with 15+ years of experience as a senior-level executive across sales and operations. Currently, Matt serves as COO / Executive Vice President at Tristar Products, managing sales and operations with P&L responsibility.
Prior to Tristar Products, Matt served as EVP, American Sales at LiveOps, a cloud-based contact center and labor marketplace, where he directed sales for the enterprise solution division. Prior to LiveOps, Matt was in Product Management at Lycos and he started his career as Engineer at Netscape.
Matt received BS in Applied Mathematics from UC Davis and MBA from UC Berkeley.
Why do you enjoy working with Founders? Founders are a unique type of highly creative people manifesting change in the world. By starting businesses, they are demonstrating tremendous courage, commitment, and capacity for hard work. I appreciate and have a deep respect for every founder I meet. I know how hard it is to “move the mountain” in face of the natural state of inertia. It gives me great pleasure to be one of the people that truly helps founders on their way to where they are going.
How do you help Founders in the portfolio? I have been the founder and CEO of several companies over my career. I have executed many financings, hired and managed many people, built technology and commercial operations, and bought and sold companies. While I certainly haven’t seen everything, I do have a deep reservoir of experience to share with founders that can help inform their perspective and decisions. I try always to be available to our founders to help them in any way I can.
What advice do you have for founders who are starting out?Remember to take care of yourself. Founders often put themselves last in terms of giving their energy to the company and their other commitments, which can lead to exhaustion and anxiety. This is a long and difficult journey, and the warrior who does not know how to rest will quickly be unfit for battle.
How was working through several downturns informed your view as an operator, advisor, and investor? I have been involved with tech startups since the late 90s, first by co-founding and leading several companies, and later by investing in many high-growth startups. As such, I experienced quite a few downturns and was able to see how the ability to face such negative events and to grow from them was a key long term success factor absolutely required for the best startups. In downturns, I have learned first-hand, that many of the following elements could have a life or death impact on the business: the presence of a strong and positive company’s culture; the alignment of all the founders; the flexibility, persistence, and resilience of the management team: the underlying strength of the unit economics, the level of satisfaction of the company’s partners and customers.
Do you miss being a founder/operator? What are some highs and lows of being a founder? I tremendously miss my experience of starting and running companies. The thrill of figuring out the market dynamics and defining a vision for the company, of identifying the path forward, of bringing on board, motivating and learning from an exceptional group of operators and investors, of going outside of our comfort zone and adjusting to all kind of complexities, of closing the first large deals, of listening to delighted customers, of seeing team members fulfill their tremendous potential, etc. All of this was so incredibly exciting, but I don’t miss the lonely periods I sometimes felt as a CEO and the times when I would wake up in the middle of the night being worried about (often-insignificant) issues.
Courtney is passionate about helping startups execute, deliver, scale, and build excellent teams founded on strong cultures. She has an investment portfolio of over 30 startups.
Courtney has held executive leadership and management positions in technology for over fifteen years at both startup and Fortune 500 companies. She joined Salesforce when it was fewer than 60 employees and was a key technology leader in building the 1+B market-leading SaaS service and company that defined the cloud. She scaled her organization from 2 to 300+ over her 10 years at Salesforce.com, delivering innovation with excellence and defining the industry standard on how to consistently deliver scalable, reliable on-demand software with renowned quality.
Charles is a seasoned technology investor, executive, and advisor with over 20 years of experience spanning private equity, venture capital, corporate development, and investment banking. He is a recognized strategy and deal leader with a successful track record of over $25 billion in investments and acquisitions across the technology industry. Charles is currently an active investor, board member, and advisor to several emerging growth companies and investment firms.
Previously, Charles was a Partner and Managing Director at Warburg Pincus where he led the firm’s multi-stage investing efforts in growth companies across the Enterprise and Communications technology sectors. His areas of focus included software, infrastructure, and services at the intersection of cloud computing, mobility, and data.
Prior to joining Warburg Pincus, Charles was the Vice President and Head of Corporate Development at Cisco where he managed a global team responsible for driving Cisco’s worldwide acquisition and venture capital strategy. During his 10 years at Cisco, Charles led more than 30 acquisitions totaling over $20 billion including some of Cisco’s largest and most successful transactions. He was also responsible for Cisco’s $2 billion global venture capital portfolio that spanned across segments and stages creating significant strategic and financial returns.
Charles holds an MBA from the Stanford Graduate School of Business and a Bachelor’s degree with honors from Tufts University
Yuri served as a visiting/part-time partner at Y Combinator. In addition, Yuri is an active angel investor with portfolios including Flexport, Boom Supersonic, Mattermost, and others.
Prior to Y Combinator, Yuri was Co-Founder and CEO of AeroFS, an enterprise collaboration platform which got acquired by RedBooth in 2017.
Yuri graduated from the University of Toronto’s elite Engineering Science program, majoring in Computer Engineering. Yuri was studying towards a Masters of Applied Science focusing on Distributed Systems at the UofT before taking a leave of absence to start AeroFS.
Judy was employee number 50 at Salesforce, where she was instrumental in the Company’s early product and marketing efforts. She was also acting CMO at Zuora and several other leading enterprise SaaS startups such as Servicemax and Conga. A tech industry veteran, Judy has 20 years’ experience investing in and building enterprise SaaS companies from the ground up.
In addition, Judy Loehr is a VC investing in early-stage tech companies with enterprise SaaS and AI products. Judy transitioned to the VC world in 2014, building a firm in San Francisco and investing in early-stage cloud business application companies. With Bayla Ventures, Judy is now investing in a new portfolio of successful enterprise SaaS and AI companies.
In her spare time Judy mentors cloud executives, and is the Executive Producer for Makeshift Society – the first-ever tv comedy series about a female founder in Silicon Valley.
Ofir is currently Chief Business Officer at Indoor Robotics and Insoundz. Prior to Indoor Robotics, Ofir was General Manager and VP Ventures of Open Innovation at Johnson Controls (“JC”) where he led select JC investments and startup partnership. Prior to JC, Ofir was CFO at Tyco Israel and was at P&G for 10 years with various roles including Co-Founder & CFO at Duracell Powermat JV and CFO of P&G Israel. Ofir started his career at Deloitte in Israel.
While we are investors and ditched our pagers years ago (if we ever had them), we are like doctors in that we are always on call 24/7. We have a high degree of urgency. We are highly competitive and like to win. We know you walk through or over walls and we should be expected to do the same as well.
We make hundreds of highly curated introductions per year that drive tangible business value. These include intros to the Series A, B, or C investors who end up leading your round, intros to the key CTO hires to scale your engineering teams, intros to the CMO to drive your enterprise marketing efforts post-Series A round or to the F1000 customer prospects that translates into a large six-figure enterprise deal.
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