Scott built his career by identifying new markets and shaping innovative products for them. In 1995, he identified search engines as a significant advertising medium and invented the first products to automate marketing across multiple search engines, ultimately creating the bid-for-placement business model used by GoTo/Overture (and now Google AdWords) and serving as VP Ideas at GoTo-incubator Idealab. As an initial investor and Director at PayPal, he was a co-inventor of the ‘email payments’ product now widely used on eBay. In 2000, Scott saw opportunity in the unbounded growth of email traffic, co-founding IronPort Systems and serving as CTO. Now the market leader in anti-spam technology, IronPort was acquired by Cisco Systems for $830 million in 2007.
| Company | Date | Round | Size | Participants |
| Zivity | 8/07 | Seed | $1M | 3 |
| Powerset | 6/07 | Series A | $12.5M | 4 |
| Causes | 1/07 | Series A | $2.35M | 2 |
| Slide | 2005 | Series A | 2 | |
| Zappos | 5/02 | Series A | $5.7M | 2 |
| iLike | 2002 | Angel | 2 | |
| LiveOps | 2001 | Series A | $1M | 2 |
| PayPal | 1/99 | Series A | 2 |