"I definitely didn't go seeking the crazy, tumultuous career I've had."

With high-profile stints at TechCrunch, Yahoo! Finance (where we overlapped) and Business Week, Sarah Lacy was well-established as a journalist and author when she founded the digital media company, Pando, in early 2012. Now, on the eve of launching her second venture-backed startup, Chairman Mom, Lacy recalls leaping into entrepreneurship via one of the most unlikely scenarios in the annals of Silicon Valley.

In late 2011, Lacy left TechCrunch -- which had been purchased by AOL the prior year -- while on maternity leave with her first child. "I took my baby fundraising with me," she says, recalling another thing few working parents would dare do -- especially given that less than 3 percent of venture funding goes to women-led startups, according to Harvard Business Review, never mind startups led by moms with a newborn.

That said, Lacy had one key advantage: after years covering the startup world as a journalist and author, she knew Silicon Valley's heaviest hitters, including Marc Andreessen, who invested $1 million in Pando's 2013 seed round, which raised $3 million.

"That was the largest angel [investment] he'd done in anything that wasn't one of his companies,"  Lacy recalls. "It was a stunning vote of confidence in me as a founder."

'A Stunning Vote of Confidence'

In fact, Andreessen had much more confidence in Lacy than she did in herself.

"I don't know why he always had belief in me -- belief I didn't have" in myself, she says. "I've been incredibly lucky to have several male mentors who had belief in me that was totally unwarranted...there was nothing I'd done to justify it."

Lacy doesn't lack for self confidence now, having guided Pando to profitability despite a high-profile battle with Uber, which allegedly tried to shut down the company and infamously sought to smear Lacy personally.

"People respected how scrappy we were, how we willed ourselves to stay in existence when the most highly-valued company in Silicon Valley history was trying to put us out of business," Lacy says. "What good investors prize is someone who has the courage of their convictions, and is never going to back down."

Maybe Andreessen and others saw that grit and determination in Lacy before she did. Today, she credits Pando's success and her personal experience as a (now) single mother for her self-confidence, which is brimming as she talks about Chairman Mom.

"I see being a mother as the most badass thing possible," she says. "I'm all in as mom, all in as a founder. It's exhausting. What I do on a daily basis is so much harder -- and takes more agility and problem solving -- than what 90 percent of 20-year male founders" have to deal with.

At this point, you're probably either cheering wildly or rolling your eyes...

Lacy, who calls herself as  "an unapologetic feminist" would no-doubt prefer the former... and certainly won't be deterred by the latter.

'Bigger Than Anything Else I Was Doing'

Either way, you can't deny Lacy has her finger on the zeitgeist with Chairman Mom, a subscription site that describes itself as 'a troll-free, abuse-free platform for working professional women.'

Chairman Mom grew out of a number of side projects -- notably a podcast and a series of private dinners with other female entrepreneurs - Lacy did to support her most recent book, A Uterus Is a Feature, Not a Bugwhich came out in late 2017.

"When I pitched the book, I thought we'd have the first female President," Lacy says.

Then Hillary Clinton lost...and then the #MeToo movement shined a light on shocking levels of misogyny in our society. As 2017 "got worse and worse," the so-called side projects around female entrepreneurship and empowerment "became bigger than anything else I was doing," Lacy says. "I realized 'this is what I should really be doing'."

Lacy remains committed to Pando and plans to run both companies for the foreseeable future. "If Chairman Mom grows to point where I can't do that, we'll cross that bridge."

As with Pando, Lacy raised venture funding for Chairman Mom -- $1.4 million in seed capital from investors including Tim Connors' Pivot North and Reid Hoffman's Greylock Discovery -- a decision over which she "agonized."

In the end, "I didn't have the luxury not to," she says, adding there's no simple answer to how'd she advise someone facing a similar decision.

"'Don't raise too much'...'raise as much as you can' -- both are true," Lacy says. "For every piece of advice, I can find a founder who can give you the exact opposite advice. There's no playbook. The whole point is you're doing something new, something innovative -- otherwise why would you do it?"

Published on: Feb 1, 2018