20VC: Slack Founder Stewart Butterfield on Leadership Styles, Decision-Making, The 3 Levels of Wealth, IPOs vs Direct Listings & Why Effective Entrepreneurship is Like Parkour

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC

Finance, Venturecapital, Tech News, News, Siliconvalley, Technology, Investing, Startups, Business

4.4 • 637 Ratings

🗓️ 16 November 2020

⏱️ 44 minutes

🔗️ Recording | iTunes | RSS

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Summary

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek.

In Today’s Episode You Will Learn:

1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey?

2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it?

3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour?

4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises?

5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding?

Item’s Mentioned In Today’s Episode

Stewart’s Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked

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Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Transcript

Click on a timestamp to play from that location

0:00.0	This is the 20 minute VC with me, Harris Debbings, and stays a very special day. I think a lot of
0:04.3	people forget I started 20 VC from my bedroom with just $50. And so having guests like ours today
0:09.6	is a real pinch-me-dream moment in many ways for me. And so with that, I'm thrilled to welcome
0:14.0	Stuart Butterfield, founder and CEO at Slack, the leading channel-based messaging platform
0:19.1	used by millions to align their teams, unify their systems,
0:22.8	and drive their businesses forward. Prior to their direct listing in June 2019, Stuart raised over
0:28.0	$1.3 billion from the likes of Excel, Thrive, SoftBank, Kliner, IVP, T-Rode, GV, and Andreessen,
0:35.9	to name a few incredible investors. Prior to founding Slack,
0:39.2	though, Stewart also co-founded Flickr, a company he built into one of the largest web services
0:43.1	in the world. And due to his many incredible successes, Stuart's also been named to the 100
0:47.5	most influential people in the world by Time magazine and one of the top 50 leaders by Business
0:52.6	Week. I'd also want to say a huge thank you.
0:54.6	This schedule was a massive team effort, Andrew Briccia at Excel, Josh Kushner at Thrive,
0:59.2	Mamun Hamid at Kleiner at Perkins, and Paul Razanja at Balser. For some amazing questions suggestions
1:03.9	today, I really did so appreciate that. But before we move into the show today, I want to take
1:08.4	a moment to mention HelloSign, a great example of a company that found success in building a product focused on user experience.
1:14.6	HelloSign is an effortless e-signature solution used by millions to securely send and request legally valid digital signatures and agreements.
1:22.1	They raised a total of $16 million in funding and recently got acquired by Dropbox for an impressive $230 million.
1:28.7	Check out HelloSign.com forward slash 20VC to join the thousands of companies and founders
1:34.1	who value fast, secure and simple e-signatures.
1:37.6	And last but by no means least, and staying on the theme of amazing, beautiful products,
1:41.6	the team over at Pendo, the product cloud company, is expanding rapidly throughout Europe
	...

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