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Startups Weekly: Lessons from a failed founder

I sat down with Menlo Ventures partner Shawn Carolan this week to talk about his early investment in Uber. Menlo, if you remember, led Ubers Series B and has made a hefty sum over the year selling shares in the ride-hailing company. Ill have more on that later; for now, I want to share some of the insights Carolan had on his experience ditching venture capital to become a founder.
Around when Menlo made its first investment in Uber, Carolan began taking a step back from the firm and building Handle, a startup that built tools to help people be more productive. Despite years of hard work, Handle was ultimately a failure. Carolan said he shed a lot of tears over its demise, but used the experience to connect more intimately with founders and to offer them more candid, authentic advice.
People in the valley are always achievement-oriented; its always about the next thing and crushing it and whatever, Carolan told TechCrunch. When [Handle] shut down, I had this spreadsheet of all the people who I felt like I disappointed: Seed investors who invested in me, all the people at Menlo and my friends who had tweeted out early stuff. It was a long spreadsheet of like 60 people. And when I started a sabbatical, what I said was Im going to go connect with everyone and apologize.
Today, Carolan encourages founders to own their vulnerabilities.
Its OK to admit when youre wrong, he said. Now I can see it on [founders] faces, I can see when theyre scared. And theyre not going to say theyre scared but I know its tough. This is one of the toughest things that youre going to go through. Now I can be there emotionally for these founders and I can say heres how you do it, heres how you talk to your team and heres what you share. A lot of founders feel like they have to do this alone and thats why you have to getcomfortable with your vulnerability.
After Handle shuttered, Carolan returned to Menlo full time and made the firm a boatload of money from Rokus IPO and now Ubers. Anyway, thought those were some nice anecdotes that should be shared since most of our feeds are dominated by Silicon Valley hustle porn.
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Startups Weekly: Lessons from a failed founder

IPO corner



Uber dropped its S-1: Weve got the basic deets, a rundown on key stakeholders, the companys plan to help drivers buy stock, a look at all the money its has made from global divestitures and a glimpse at the companys R&D spending for self-driving cars.




Pinterest is an undercorn: The visual search engine set its IPO range at $15 to $17 per share earlier this week. That translates to a midrange valuation of $10.64 billion, nearly $2 billion less than the companys most recent private market valuation of $12.3 billion, hence undercorn.




PagerDuty pops: The SaaS businesss shares began trading on the NYSE on Thursday, popping more than 60 percent on their debut.




Jumia makes history: Jumia became the first startup from Africa to list on a major global exchange this week when it debuted its shares on the NYSE under the ticker symbol JMIA.




Lyft declines: The Uber competitor finished out the week trading at less than $60 per share, significantly below its initial share price of $74. Ouch.



Funds on funds on funds
There were so many fund announcements this week; heres a quick list.



Source Code Capital raises $570M




B Capital nets $406M




Defy.VC gets $262M




Slow Ventures grabs $220M




LiveOak Venture Partners secures $105M




Octopus Ventures nabs ?83M



Extra Crunch
Lots of great new exclusive content for our Extra Crunch subscribers is on the site, including this deep dive into the challenges of transportation startup profits. Plus: When to ditch a nightmare customer, before they kill your startup; The right way to do AI in security; and The definitive Niantic reading guide.
Lawsuits
Sinema, that one MoviePass competitor, has run into its fair share of bumps in the road. TechCrunchs Brian Heater hopped on the phone with the startups CEO this week to learn more about those bumps, why its terminating accounts en masse, a class-action lawsuit its battling and more.
Startups Weekly: Lessons from a failed founder
Photo by Stephen McCarthy / RISE via Sportsfile
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