Enter , a Seattle-based VC firm focused on digital media. In February 2006, DVDPlay closed a $4.5 million Series A . The term sheet was brutal: 8% preferred liquidation preference, a full ratchet anti-dilution clause, and a board seat for Voyager’s managing director.
No round occurred.
The initial funding model was almost quaint: . Each machine cost $12,000 to build and $500 per month to service. If a kiosk pulled in $1,200 a month (roughly 40 rentals at $1.50 per night, plus late fees), Phillips plowed 90% of that back into building the next machine. By 2004, DVDPlay had 47 kiosks in Oregon and Washington. They were profitable, but tiny. dvdplay funding
Phillips raised one final round: from a group of angel investors in Portland. The terms were a Hail Mary: 20% discount to the next round’s valuation, but if no round occurred by December 2011, the notes would convert at a $0.25 per share valuation (down from the $4.50/share of Series B).
The funds were earmarked for one thing: . DVDPlay ordered 500 new kiosks from a manufacturer in Ohio. They hired 50 part-time “route drivers” to restock discs. By Christmas 2006, they had 600 kiosks in 19 states. Revenue hit $8 million. Losses hit $2.1 million. Enter , a Seattle-based VC firm focused on digital media
Then came Redbox. In late 2005, Redbox—then a joint venture between McDonald’s Ventures and Coinstar—rolled out 800 kiosks nationwide, pricing rentals at $1.00, undercutting DVDPlay’s $1.50. Overnight, Phillips’ bootstrapped model became unsustainable. He needed scale. He needed funding.
| Round | Year | Amount | Lead Investor | Notable Terms | Outcome | |-------|------|--------|---------------|----------------|---------| | Series A | 2006 | $4.5M | Voyager Capital | Full ratchet, board seat | Burned for expansion | | Mezzanine debt | 2008 | $3.0M | Wellington Financial | 14.5% interest, convertible | Defaulted | | Studio rev-share | 2008 | $2.0M (imputed) | Lionsgate/Warner | 15% of revenue | Raised COGS to 47% | | Series B | 2009 | $12.0M | Oak Investment | 2x liquidation pref, pay-to-play | Lost on streaming pivot | | Convertible notes | 2011 | $2.5M | Portland angels | 20% discount, $0.25 floor | Converted to zero | | | | $24.0M | | | Recovery: $3.1M | No round occurred
“We wrote the check because DVDPlay had the best software stack,” recalls a former Voyager associate (speaking anonymously). “Redbox machines required a dedicated phone line. DVDPlay used cellular modems. That was the edge.”
