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Greg Gottesman is the co-founder and managing director of Pioneer Square Labs, former managing director at Madrona Venture Group, and is a co-founder of Rover (ROVR), the biggest pet sitting marketplace in the nation.

Greg has spent his entire life authoring his journey. At 22 he published a book that became the survival manifesto for the 1980’s college student (7 editions), at 24 he became a lawyer which he soon left so he could start working in business, and has been an investor in venture capital ever since.

Greg has plenty of noteworthy accomplishments too long for this introduction, including a TED talk, getting both an MBA & JD from Harvard, and his cousin being Fred Savage (no joke).

This conversation was remarkable; Greg is super generous & a well of knowledge of not only marketplaces, but startups in general. As well, a gifted storyteller.

We dive deep into…what spurred Greg’s entrepreneurial journey, the genesis of Pioneer Square Labs, how to build a marketplace startup from scratch & what makes it tricky, obsessing over marketplace dynamics, the 80/20 rule for marketing funnels, killing great ideas, and “starting with 1” (what does this mean?).

This episode is particularly valuable for digital marketplace founders, COOs, and CEOs. Greg has both founded AND funded several marketplaces, so he’s able to share deep specifics on key principles & secrets.

Please enjoy!

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Show Notes

• Why should you keep a cup of change on your nightstand? [4:25]
• How long did it take to write the manuscript for the book? [6:50]
• We saw you wrote for GeekWire. Was this specific to Seattle? [9:00]
• When you say ‘studio’, do you mean Pioneer Square Labs? How is it different than Madrona Venture Group? [10:09]
• 50% of the ideas, come from within? And you need to then source the founders? [14:01]
• What does it mean to make decisions based on “the who”? [16:22]
• Do you have a company that comes to mind (that took advantage of COVID-19)? [18:49]
• What do you think about differently, when you build a marketplace from scratch? [21:50]
• A real secret to marketplaces: conversion & marketplace dynamics [24:49]
• How do you coach founders and start to solve conversion/marketplace dynamic problems? [27:30]
• Did you figure out conversion? Were you ever supply constrained? [32:00]
• Picking a marketplace as a business model. What was the decision around this? [34:13]

Links from Episode

• Connect with Greg: LinkedIn | Twitter |  PSL
• Pioneer Square Labs
• College Survival by Greg Gottesman
• High School Survival by Greg Gottesman
• Law School Survival by Greg Gottesman
• GeekWire
• StarkRaving VC (Greg’s blog)
• Rover.com
• Madrona Venture Labs
• Fortive
• Fluke
• Ted Dintersmith
• TeamSense
• Craigslist
• Aaron Easterly
• Brent Turner
• DogVacay
• Joon
• Kevala
• What unit economics are
• Xiao Wang
• Boundless

What ‘startup secret’ did you learn from Greg? Comment below!