On entrepreneurship: Thiel, Dorsey, Conwell [Technical.ly Podcast] - Technical.ly


Nov. 5, 2014 11:19 am

On entrepreneurship: Thiel, Dorsey, Conwell [Technical.ly Podcast]

Turning an idea into a company is hard. In this month's Technical.ly Podcast: lessons from repeat entrepreneurs.
HubBub Coffee owner Drew Crockett with fellow entrepreneur (and Square CEO) Jack Dorsey, during Dorsey’s recent visit to Philadelphia.

HubBub Coffee owner Drew Crockett with fellow entrepreneur (and Square CEO) Jack Dorsey, during Dorsey's recent visit to Philadelphia.

(Photo by Kimberly Paynter/WHYY)

Most startups fail.

So what can we learn from those who took an idea to launch, beat the odds (or not) and then did it all over again? This month on the Technical.ly Podcast we hear from repeat entrepreneurs. Internet titans, sure; but also founders feeling their way toward success.

We start with Peter Thiel, the cofounder of PayPal and Palantir Technologies, and the celebrated investor behind FacebookAirbnb and a bunch of other tech companies you’ve probably heard of.

Thiel was in Philadelphia in late September talking about his new book, Zero to One: Notes on Startups, or How to Build the Future.

The Franklin Institute event featured an onstage Q&A, but we also taped an interview afterwards about how Thiel spots a good pitch, what the next big thing may be and why he’s so into the future, anyway.

After that, we check in with 21-year-old Thiel Fellow Maddy Maxey. The designer and technologist was recently interviewed by Venture for America Fellows Shilpi Kumar and Mike Wilner for their InOverOurHeads podcast. Check out the full interview with Maxey here.

Then it’s back to a leading man of the social internet era: Jack Dorsey, cofounder and chairman of Twitter and cofounder and CEO of Square.


Dorsey was in Philadelphia spreading the word about Square Capital, a cash advance program that helps entrepreneurs strengthen their businesses.

We met up at HubBub Coffee to talk about his vision for zapping funding to select entrepreneurs using the Square platform. “If it’s growing our seller’s business, it also grows our business as well,” Dorsey said. “We have a nice virtuous cycle in that sense.”

I also asked the St. Louis native about his decision to head to Ferguson in the aftermath of the controversial killing of Michael Brown. You can hear the entirety of his candid response in the audio player below:

We close out this month’s podcast with some #realtalk on startup (and relationship and financial) failure — and why it’s not stopping McKeever Conwell from going back for more.

The Baltimore entrepreneur reprises a talk he delivered at Baltimore Innovation Week’s #Failfest. His first startup may have gone down in flames, but his second one, RedBerrry, is currently being accelerated at DreamIt Ventures.

Because, like a hitter in baseball, failing seven times out of ten is greatness.

  • Listen below, download the episode or subscribe to the Technical.ly Podcast on iTunes or Stitcher.

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