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Happy fourth anniversary to the Mama Bear!

Newsletter editor Lily here.

On September 7, 2017, I published the first-ever issue of Chairman Mom’s Mama Bear newsletter. While I don’t have an exact count for how many newsletters I’ve created since then, rough estimates put it at around 1,000 emails. WHEW.

Whether you’ve received all 1,000 of those messages or you just subscribed today, I want to say a gigantic THANK YOU to you for being part of this journey with me and the entire Chairman Mom team. I think I speak for all of us (readers included!) when I say that it feels like we’ve lived a million lives in the past four years since that inaugural email. Read more...

One is not enough

We saw something strange in the last few years in venture capital. 

There was a concerted push to get more women into partner roles, the belief being that it was the quickest way to get more than 3% of funding flowing to female founders. There was a massive increase in women joining top venture firms and being funded to start their own. But the percentage of funding going to female founders went down. 

It’s infuriating. But at the root of a lot of the problem is the trap of being “an only.”  Read more...

Challenges, challenges

There are clearly a lot of challenges in building this company. 

I’m a woman. We don’t get a lot of funding. I am building a company for women, which is even harder. Most of the people who write checks have wives who don’t work, so their spouse may not even get the problem we are trying to solve. 

And when you are a startup, everything is harder when access to capital is harder. You have way less room to make mistakes. You lose more ownership faster because the capital you get can be expensive.  Read more...

Life is too short for toxic people

On Friday night, I took myself to dinner and a movie. It was a shit day of major personal upheaval. 

At the next table, there was a woman who could have been me today or at other points in my life, only louder. She was venting about an absolutely toxic family member and half the table (who had none of her lived experience) was telling why she was overreacting and the other half was sitting unsupportive and mute. 

I didn’t have to know much backdrop: The person in question was an addict. The person in question was constantly trying to one-up relationships by throwing around cash and status. And yet, the person in question was also a total user. On this occasion, he’d convinced them all to go to this restaurant, run up a huge bill, and then suddenly realized he had a flight to catch and dashed out, leaving them a $300 tab.  Read more...

Avoiding the old boys’ club

Women have spent centuries trying to break into the old boys’ network. When I was a reporter for some 20 years, I heard the same refrain again and again from women who’d made it in tech: I was able to beat the odds because I’m basically a guy. Or, I socialize like a guy. Or, I talk like a guy or drink like a guy. I like sports. I grew up with brothers, so I’m comfortable around men. 

Ah, yes the bit of internalized misogyny that’s really familiar for me, because this was me too: “The honorary man.” It’s adjacent to another branch of internalized misogyny: Female exceptionalism. That’s when you draw your superiority and ego and satisfaction from being the woman who can make it in a boys’ club. The high of beating the odds. (No judgement, I did this too!) Read more...

Welcome (again)

There are a lot of new people in the Chairman Mom community after the last few months. 

I know you get onboarding emails, but I wanted to pause for a minute and tell you a little bit about who we are and how we all got here. 

My name is Sarah Lacy, and I was told every moment of my existence that becoming a mother would end my career. When I had my first child, Eli, the opposite happened. I became more intense, more driven, more ambitious. I took more risks, and I became better at my job.  Read more...

On the road

Newsletter editor Lily here.

By the time you read today’s newsletter, I’ll be somewhere up in rural Maine, where I’m whitewater rafting with a few book club friends over a long weekend.

To be completely honest, I’ve been waffling on this trip for weeks. I signed up back in the winter, when August seemed far off and we all thought we’d be in a different place in the pandemic. As my summer got rougher, I couldn’t decided if driving seven hours in each direction for a three-and-a-half-day trip was worth it. Read more...

Home away from home

Newsletter editor Lily here.

The dynamic duo is back together again: I’m in upstate New York staying with my mom for the next month or so.

Many of my friends still marvel at the fact that my mom, brother, and I spent the first three and a half months of the pandemic trapped in a small apartment and didn’t have a single fight. I also spent another three weeks up here last Christmas, and guess what? No fighting then either.

Obviously, we have a few things going for us. My brother and I are full-fledged adults (the not-so-little man just turned 21 earlier this month!), so we’re able to entertain ourselves and do our own things. My family is very, very known for being good at physical boundaries; for example, everybody’s aware of when I need to do work, and no one bothers me about it. And my mom and I have been close for a long time. Read more...

Belief is transformative

Someone believing in you is an incredibly transformative thing. 

I know that is obvious, right? But it doesn’t make it any less powerful when you spend your life so constantly underestimated because of who you are, where you came from, the color of your skin, or your gender. 

Yesterday, we had our first IRL Chairman Mom board meeting in a long time. We have an expanded board and a lot more pressure and expectation to build something HUGE. People have made serious bets on us. 

There’s always stress and pressure that comes along with that. But there was something else palpable to me in the room yesterday: BELIEF in us. Not just our idea, and the market, and WHY a company focused on leveling the playing field for women is something worthy of millions of dollars of investment. But our team, of Paul and me as founders.  Read more...

Sign up for New Media Mastery before it’s too late

Today’s intro is from Megan Harding, Chairman Mom’s Head of Courses & Events.

Many of you know me as the person who coordinates all the amazing free Zoom events and courses for Chairman Mom. As someone who’s been to a lot of virtual and in-person events, it’s not too often that I feel truly energized and excited after working an event (especially since they typically end at 10pm on the East Coast where I live!). Our event last Thursday on how to be polarizing (in a good way), promoting our course New Media Mastery: Lesley Gold & Sarah Lacy’s PR Academy, was one of those exceptions. Read more...