Investing in Extraordinary Leaders: Announcing Our $36M Fund II

Since day one, my partner, Craig Cummings, and I have been laser-focused on finding, backing, and building strong bonds with the very best leaders in early stage technology. We believe the best ones are experienced trial-by-fire entrepreneurs or are military-trained and have the ability to motivate others to action, inspire trust, and plan heuristically. We invest with conviction when those attributes are present.

Our approach to extraordinary leadership — influenced by our own decades of training at West Point, then in the military, and subsequently as C-level operators in 15 different companies — is paying off and, today, we’re excited to share the news of the closing of Moonshots Capital Fund II and our first five investments.

Our $36M Fund II will enable us to double down on our commitment of investing in, supporting, and scaling companies led by extraordinary leaders, and we’re grateful to have the confidence of an incredible group of LPs — most of whom we consider close friends.

We will continue to invest in late Seed or Series A companies and will target 6–8 new investments per year. Of course, this fundraising process wouldn’t have been possible without the continued successes of our Fund I portfolio companies.

In Fund I, we were proud (but not surprised) to see open source AI platform Gretel, led by former NSA engineer Alex Watson, recognized by Forbes as a “Top 50 AI Company to Watch.” They subsequently closed their $12M Series A led by Greylock. Navy Veteran Marcus Carey, founder of cybersecurity platform Threatcare, exited with a sale to ReliaQuest in 2019 while aircraft augmented reality training company Red 6, led by a former British fighter pilot, Dan Robinson, recently raised a $30M Series A round led by Snowpoint Ventures.

In addition to traction and returns, our theory and practical approach to extraordinary leadership has led to a diverse set of founders: 86% of Fund I companies have at least one nontraditional founder with 36% having a Black or Latinx, 21% were founded by a woman, and/or 36% have a military veteran on the founding team.

Fund II: We’re Just Getting Started

We’re excited to share more about the incredible leaders behind our first Fund II investments. Two of the companies are already unicorns (Pacaso and ID.me) and the others are well on their way.

Omair Tariq & Jim Jacobsen of Cart.com, HQ’d in Houston, Texas

Omair and Jim are extraordinarily successful entrepreneurs and we were excited when our friends at Mercury Fund introduced us to Cart.com. Cart.com is the first full-scale E-commerce-as-a-Service (ECaaS) platform, delivering a fully integrated and owned suite of tools to scale businesses online. CEO Omair Tariq is an e-commerce superstar, formerly serving as the COO and CFO of Blinds.com, which sold to the Home Depot. Jim Jacobsen was the co-founder and CEO of RTIC Outdoors, which he grew to $220M in revenue its first year. Moonshots Capital invested in the $25 million Series A round alongside Mercury Fund, Arsenal Growth, and Scarlet Venture Fund.

Blake Hall of ID.me, based in Northern Virginia

Military veteran and bronze star recipient Blake Hall has been our “poster CEO” for extraordinary leadership. Working with both government and business partners, ID.me simplifies the online identity verification process — building the “identity layer of the internet.” Craig and I invested in Blake’s Seed Round in 2011 (and every round since then), and I have served on the ID.me board for over 11 years. Blake is the core reason why we invested in 2011, and most recently via Fund II in their $100M Series C alongside Viking Global, CapitalG, and other distinguished investors. With each new milestone the company achieves, we are increasingly bullish about ID.me’s potential to be one of the biggest, well-known, and well-respected tech companies in the world.

Karyl Fowler & Orie Steele of Transmute, based in Austin, Texas

Transmute’s platform solves vulnerabilities in trade compliance by increasing visibility and traceability in supply chains. Both Karyl and Orie have deep domain expertise, holding chair-level leadership roles at standards development organizations including the Decentralized Identity Foundation (DIF) and World Wide Web Consortium (W3C). Karyl exhibits all the leadership principles we look for in our Founders — domain expertise, high attention-to-detail, dogged perseverance and truly coachable, to name only a few. We led Transmute’s $2M seed round.

Austin Allison and Spencer Rascoff of Pacaso, based in Southern California

Pacaso enables fractional ownership of a second home with a completely managed experience. Founders Austin and Spencer are both former Zillow executives and serial entrepreneurs with exits under their belts. Chairman Spencer Rascoff is an extraordinary entrepreneur (founding CEO at Zillow), a long-time friend, an LP in our Fund, and a frequent investor in our syndicates. They’re joined by former Starbucks CEO Howard Schultz as an advisor. We invested in their $75M Series B which was led by Greycroft, Global Founders Capital, and Acrew Diversify Capital Fund.

Scott Painter of NXCR, based in Southern California

NXCR is building the future of automotive subscriptions, integrating all industry partners including OEM’s, car dealers, fleet operators, and more. CEO Scott Painter is a well-known, highly fundable automotive industry disruptor, as well as a military veteran. He previously founded and sold CarsDirect.com, and subsequently founded and took TrueCar public. We have been friends and avid supporters of Scott dating back to 1989 and invested in TrueCar, Fair and now NXCR as we participated in NXCR’s $6M pre-seed round from Fund II.

Moonshots Capital Syndicates

We also continue to provide our Fund LPs with extraordinary access to later stage deals via our syndicate vehicles. While raising the $36M for Fund II over the last twelve months, we deployed an additional $25M via syndicates into well- known companies, like Robinhood and Carta. The syndicate vehicle allows us to not only provide our Fund LPs with access to later stage deals, but also enables us to protect our positions in our hottest companies as they grow past what would normally be supported by a microfund.

Sign up for our newsletter to keep up with our progress and fill out our syndicate interest form if you’d like to participate in our syndicate deals.

Read more about our news reported from LA here and Austin here.