Missed part 1? Click here!

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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

• Can you define unit economics & how they work? [1:17]
• The optimal number of months & years for payback period in startups [4:36]
• The different nuisances to unit economics [5:06]
• The 2nd thing people look at, lifetime value / cost of acquiring & servicing [6:04]
• How Jakub worked on the sitter side and unit economics were at play [8:09]
• The chicken or the egg problem: which one comes 1st when coaching founders? [9:54]
• Could you tell us more about Yesler and how they got their 1st customer? [16:17]
• And what is Yesler? [19:00]
• How did Yesler fare with the market for lumber during COVID-19? [19:14]
• What about getting the 1st “supplier”? [20:05]
• Rapid mayhem questions! [22:35]
• Greg’s Kosmo.com story [24:00]
• How the Internet was the most under-hyped thing [29:01]
• What’s the next big step-change in marketplaces? [33:01]
• Where can we find you? [35:44]

Links from Episode

• Connect with Greg: LinkedIn | Twitter |  Email
• Pioneer Square Labs
• StarkRaving VC (Greg’s blog)
• Rover.com
• What unit economics are
• Joon
• Yesler
• Amazon
• Kosmo.com
• Junior Mints
• Fundrise
• Arrived
• Joon
• Seattle Mariners
• Ever.green (marketplace to invest in green energy & climate action projects)
• If you’re interested in being a founder or funded, email Greg

What marketplace would YOU be? Comment below!