#30 The Messy Middle: Lessons Learned as a Founder, Investor, and Bestselling Author | Scott Belsky, Author & Venture Capitalist

“Great opportunities never have ‘great opportunity’ in the subject line.” – Scott Belsky

In this episode of Outliers, I’m talking with Scott Belsky (@scottbelsky). After starting his career at Goldman Sachs, he left to found Behance which he later sold to Adobe. He’s now the Chief Product Officer at Adobe as well as a Venture Partner at the world-renowned venture capital firm Benchmark. Scott was an early investor in Uber, Pinterest, Carta, Flexport, Airtable, and sweetgreen. And finally, he’s the best-selling author of Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality and The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture.

Scott is a modern polymath. We explore his journey from entrepreneur to investor, how he approaches investing in early-stage technology companies, as well as the lessons he’s learned at Benchmark, Adobe, and Behance.

Chapters in this interview:

• 00:00:05 – Scott’s learnings from his start at Goldman Sachs
• 00:05:35 – On co-founding Behance, and attempting to manage the “most disorganized community on the planet”
• 00:09:15 – Tactics for entrepreneurs and their teams
• 00:13:26 – The transition from startup (Behance) to large company (Adobe)
• 00:16:29 – How the desire to buy an education led to Scott’s interest in investing
• 00:18:59 – Seeing an investment grow from Seed to IPO
• 00:22:47 – How design can move the needle for a business
• 00:28:21 – Scott’s foray into venture capital and finding his ideal role melding investing with company-building at Benchmark
• 00:34:04 – On writing Making Ideas Happen and The Messy Middle
• 00:39:11 – Startups avoiding the fate of the “one-hit wonder”
• 00:43:32 – Investment trends that Scott is focusing on
• 00:47:31 – Scott’s favorite failures

Show notes with links, quotes, and a transcript of the episode: https://www.danielscrivner.com/notes/scott-belsky-outliers-show-notes 

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