May 12, 2021

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

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

Scott Belsky is a modern polymath. He founded Behance, which he later sold to Adobe. He’s a Venture Partner at Benchmark and has invested in companies like Uber, Pinterest, and sweetgreen, and he’s currently the Chief Product Office at Adobe. We discuss the lessons he’s learned along the way, his investment methodology, and surviving the messy middle in any ambitious endeavor.

“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: 

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