OakStone Ventures

OakStone Ventures was a strategic seed-stage investment fund in Palo Alto. Frank served as its general manager from January 1999 to December 2010, through the peak of the dot-com years, the bust that followed and the recovery after it.

He ran the fund while building and running companies of his own, including NanoSpace, Neopolitan Networks and CityNAP. Several of the fund's companies crossed paths with his operating work, as the portfolio shows.

• Kana Communications. Later a public company. Yipes also ran Kana internally, one of the systems Frank led its migration to.
• Keyhole. Later acquired by Google and now Google Earth. Neopolitan Networks hosted and helped scale it.
• Yipes. Later acquired by Reliance Communications for $300 million, in 2007.
• YY Software. Frank also sat on its advisory board from 1997 to 1999.
• SpaceCurve. A new kind of database.
• HeavyMail. Frank sat on its board from 2004 to 2010.

Seed investing is mostly saying no, and learning exactly why. Frank carried the same work into the San Antonio Technology Accelerator Initiative, where as a director from 2007 to 2010 he vetted and advised funding candidates.

Not every outcome is decided by the product. HeavyMail finished development and then stopped after a death in the founder's family just before launch. A founder hears about the companies that exit. An investor sees the ones that stall, and learns which risks a plan can cover and which it cannot.

• Fundraising readiness. A pitch, a model and a data room reviewed by someone who has sat through the diligence from the investor's chair.
• The questions before they are asked. Technical risk, market timing, burn and what the next round needs to see, named early enough to fix.
• Board experience from both sides. Investor, director and operating executive, often at the same company.
• A technical read on the technology. A fractional CTO who can tell an investor what the product actually does, and tell the founder what an investor will make of it.