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 Uber’s Series B and has made a hefty sum
over the year selling shares in the ride-hailing company. I’ll
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; it’s
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
I’m going to go connect with everyone and apologize.”

Today, Carolan encourages founders to own their
vulnerabilities.

“It’s OK to admit when you’re wrong,” he said. “Now I
can see it on [founders’] faces, I can see when they’re scared.
And they’re not going to say they’re scared but I know it’s
tough. This is one of the toughest things that you’re going to go
through. Now I can be there emotionally for these founders and I
can say ‘here’s how you do it, here’s how you talk to your
team and here’s what you share.’ A lot of founders feel like
they have to do this alone and that’s why you have to
get comfortable with your vulnerability.”

After Handle shuttered, Carolan returned to Menlo full time and
made the firm a boatload of money from Roku’s IPO and now Uber’s. 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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Ok, on to other news…

IPO corner


Funds on funds on funds

There were so many fund announcements this week; here’s a
quick list.


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.
TechCrunch’s Brian Heater hopped on the phone with the
startup’s CEO
this week to learn more about those bumps, why
its terminating accounts en masse, a class-action lawsuit its
battling and more.

Photo by Stephen McCarthy / RISE via Sportsfile


Startup capital

Battlefield!

TechCrunch’s Startup Battlefield brings the world’s top
early-stage startups together on one stage to compete for
non-dilutive prize money, and the attention of media and investors
worldwide. Here’s a quick update on some of our BF winners and
finalists:


#Equitypod

If you enjoy this newsletter, be sure to check out
TechCrunch’s venture-focused podcast, Equity. In this
week’s episode, available here,
Crunchbase News editor-in-chief Alex Wilhelm, myself and Phil
Libin, the founder of Evernote and AllTurtles, chat about the
importance of IPOs. Plus, in a special Equity Shot,
Alex and I unpack the Uber S-1.

Source: FS – All Tech News 2
Startups Weekly: Lessons from a failed founder