Transamerica Ventures

Transamerica Ventures was born from a simple mandate: help a global insurance and asset management company stay competitive in a rapidly changing financial technology landscape. Rather than building innovation labs internally, the parent company Transamerica decided to deploy capital into promising early-stage companies across InsurTech, FinTech, and enterprise software. The fund was officially launched in February 2014 with an initial $140 million commitment, though the first official investment didn't happen until June 2014—the same month Andrew Pitz joined the team.

The early strategy relied heavily on fund-to-fund partnerships rather than direct company investments. Andrew and his team made two notable fund-to-fund bets: a $1 million investment in FinTech Collective (which itself raised a $10 million fund at the time, now significantly larger) and a $2 million check into Lear Hippo Ventures for digital marketing expertise. These weren't traditional venture returns plays—they were strategic bets to gain access to deal flow, expertise, and founder networks in areas directly relevant to insurance. As Andrew explained, "We can do whatever deals they want, but eventually some become relevant to us. We're co-investors in Next Capital together, for example."

Transamerica's "customers" are founders and fund managers willing to partner with a corporate venture arm. The firm built a systematic deal sourcing process: reviewing approximately 5,000 opportunities per year (from newsletters and market intelligence), conducting deeper research on about 500, holding 100-150 in-person meetings annually, performing due diligence on 25, and making roughly 5 investments per year. By three years in, they had deployed $60 million across 17 unique companies in 23 total investments (with 6 follow-on rounds).

The hybrid corporate-VC model created interesting tradeoffs. On one hand, Transamerica could offer relationships and insights to portfolio companies that independent VCs couldn't. On the other hand, the fund occasionally had to pass on exceptional deals that weren't "strategic enough"—a decision Andrew deeply regretted. He mentioned missing Moat (which eventually sold for $850 million to $1 billion) and earlier in Transamerica's parent company's history, passing on Facebook's B-round and Skype's A-round because "George Telecom said these aren't strategic enough."

What worked exceptionally well were their portfolio picks. Andrew highlighted strong conviction bets on PolicyGenius (backed by Steve Case and Norwest), Hixme (a unique health insurance model), and H2O (an open-source predictive analytics company signing seven-figure contracts). The open-source-as-lead-gen model particularly impressed him—seeing firsthand that developers could build free tools and successfully upsell enterprise contracts.

By the time of this interview, Transamerica Ventures had proven the CVC model worked well enough that parent company executives committed to a second fund (size TBD). The team was exploring geographic expansion into Asia and Brazil, where the parent company had existing operations and leadership open to startup partnerships. Andrew was 30 years old and sleeping 5-5.5 hours per night, reading deal flow from newsletters like Term Sheet and Mattermark Daily. The firm had moved beyond pure fund-to-fund deals to focus primarily on direct technology investments that could create genuine partnerships with the corporate parent while still chasing 10-100x returns.