I am thrilled to begin a new entrepreneurial journey with the launch of Optimist Ventures.

The firm is built on my accumulated observations, learnings, network, passport stamps, successes, and failures over the past 15 years of global tech investing and advising.

The name Optimist is inspired by the most popular sailboat in the world. The Optimist has been the de facto starting point for generations of sailors. Like this boat, we plan for our investing platform to be for those curious about the unknown future, spiritedly competitive, adaptive to the elements, resilient to the crowds, team-oriented yet self-reliant, first-principles oriented and very fun.

Our mission is to be foundational investors in backbone sectors of the economy. We will back entrepreneurs across technology sea changes in three complex & dynamic sectors: insurance, healthcare, and industrial automation.

Gratitude

First, I have to thank my Antler teammates across the 30-city, 20-country footprint, and specifically on the Antler Elevate Global Fund for everything — you taught me that we all have entrepreneurial energy in us and working together we can go farther, faster. Indeed, the last 3+ years has been a thrill, helping build a team, a brand, and a network, and surpassing 1,200 companies funded and $1B in AUM with our distinct Day 0 model. Antler is now the most active investor in the world. Magnus and team live their ambitious belief system: “founders first”, “extreme ownership”, “failure is not an option”, “do more with less” and “disagree and commit” — these are the ingredients that propel progress and fuel growth.

Tech Investing

In launching Optimist Ventures, I’ve reflected on what it means to be a technology investor. I’ve drawn on my experiences over the last technology cycle from Antler, SoftBank, Comcast Ventures, and Goldman Sachs. This experience spanned emerging markets, like Indonesia, India, and MENAP, as well as leading innovation centers, like Silicon Valley and Silicon Alley. At times, it feels like we tech investors are part of an odd, crypto-crazy, rocket-obsessed, AI-mad lot, so estranged from the Buffet value-investing disciples, forensically studying intrinsic value and lamenting revenue-based proxy valuations as bogus and SPACs as another four-letter expletive.

However, over the last 15 years of tech investing practice, it’s become clear to me that there is a credible value system in tech investing. Weirdly enough, when done well, tech investing’s foundations are not so divorced from the foundations of value-investing as they initially seem. Both require deep study, differentiated insights, robust networks, uncommon access and analysis, a disciplined work ethic, and betting with conviction at the right time.

This brings me to my SoftBank learnings. To the public, Masa and, inextricably, SoftBank are an enigmatic, Rorschachian brand of tech investor, somewhere between inveterate gambler and visionary, calculated risk-taker. My 6 years at SoftBank across 3 cities, multiples roles and funds, and my extra-curricular study of SoftBank leads me to believe that there is method to the madness. Masa possesses these foundational investing qualities in spades but may lack a certain discipline and patience. What he lacks in restraint, however, he makes up for in imagination. Imagination can run the gamut from a fever dream, devoid of any reality, to the much more grounded skill of connecting past and present to a future state. SoftBank carefully connected disparate dots across sectors, scales, geographies and time periods and, in doing so, created unique opportunities. Imagination of what can be is a required trait of all great tech investors.

While some may know him for his Vision Fund capital spree, I took from Masa an ability to laterally connect seemingly disparate trends. He brought the iPhone to Japan in 2008 with a $15B+ successful (calculated) bet on turning around Vodafone Japan; he bet on Internet and mobile adoption in China with a $20M Alibaba investment in 2000, a stake subsequently worth $144B at peak; he acquired Arm in 2016, and a mere 8 years later SoftBank’s 90% stake is worth $100B more than what was paid. Even Sprint, which many considered a blunder, was a 25%+ IRR, 8x multiple on invested capital. By these numbers, Masa really is the Babe Ruth of technology investing, and yet he is not studied with a fraction of the focus of those Omaha-going Buffet devotees.

As F. Scott Fitzgerald wrote, “the test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.” Carrying both SoftBank’s rare imagination as well as a respect for timeless investing principles and industry knowledge is the first-rate intelligence for which I want Optimist Ventures to be known.

AI & The Real Economy

Beyond this intelligence, Optimist Ventures will be an exploration of how artificial intelligence and other critical technology collide with real sectors of the economy. At Comcast Ventures, I witnessed and studied the changes to media and advertising wrought by Internet and mobile. The rise of social media aggregators, like Facebook/Instagram, YouTube, TikTok and Snapchat, upended the video distribution landscape even faster than video killed the radio star. By 2016, I caught the second half of this Big Media upset by Big Tech, and then came Fintech’s rise, led by Chime, Sofi, Acorns, Lemonade, Hippo Insurance, and Stash in the US, and by many others globally. During my tenure at Comcast, we invested or evaluated most of these. The collision of tech into financial services was powered by a superior mobile/cloud-first user experience, massive scale, seamless product bundling, regulatory arbitrages (i.e., Durbin Amendment), and a cool $500B+ of venture capital over a decade. The Fintech era yielded many venture-backed winners, many more that didn’t make it, and a lasting resolve among incumbents to sharpen their offerings.

Today, talent and capital are flowing to Artificial Intelligence at an unprecedented rate and a mind-boggling $1T+ is going into AI infrastructure. If history rhymes, we anticipate that after infrastructure will come a vertical AI adoption cycle, currently in its early innings.

At Optimist Ventures, we think AI is starting to permeate large, complex sectors, and like cloud or mobile before, will give rise to better business models and customer value propositions. We believe the transformation will be most remarkable where issues are the most acute, where workers are most stretched, where data is most siloed, and where historical returns on equity lag peer sectors. Today, coding and insurance claims co-pilots, manufacturing cobotics and remote telesurgery show that tech can augment our skills for the better. These technologies have the capability to reduce repetitive administrative burden, address long-standing inefficiencies, drive consumer surplus, and optimize our lived experience.

At Optimist Ventures, we will focus on greater efficiencies in the $1T of healthcare admin spend; in the $7T insurance industry; and for the ~20% of American labor in manual labor industries, like manufacturing, construction and warehouse/logistics. We are seeking technologies that create a positive, constructive, and symbiotic relationship with the 60M+ US workers in these sectors, who represent nearly 40% of the American workforce.

However, we recognize that technology can cause displacement, turbulence and stress — the transition may be difficult on society at large. Optimist Ventures will serve as a research project to monitor these changes to enhance better public and corporate policies. We are in the early innings of understanding this complex interplay of work and technology.

Opening Day

In 1954, Rear Admiral Dr. Grace Hopper — the pioneering computer scientist, inventor of the UNIVAC computer, the COBOL computer language, and the phrase “debugging”, whose eponymous Nvidia GPU is powering AI workloads in datacenters globally — said, “A ship in port is safe, but that’s not what ships are built for. Sail out to sea and do new things.” At Optimist Ventures, we are doing new things.

We believe that optimism is the catalyst for innovation and progress. This isn’t blind, happy-go-lucky positivity, but rather a growth mindset that sees challenges as opportunities and fuels the courage to pursue ambitious goals. We will partner with founders who embody this spirit, driving transformative change through their unwavering belief in a better future.