The Best We Ever Had

We’ve spent a lot of time talking about ‘What Not To Dos’, meetings that left us scratching our heads, and times we’ve messed up, but that’s not to take away from all the good meetings we have had. Especially the ones that came with lessons we think about pretty much everyday.

These are the types of meetings that have helped us the most:

Meeting #1: Will you give me money?

Backstory: For 370 days, we did everything we could to get in front of one particular investor. We were told he would not meet with us, wasn’t investing, and wasn’t interested. We finally got an in and he agreed to a meeting. We were given 15 minutes.

What happened: We researched EVERYTHING we could about him, his meeting style, how he likes his coffee, when he likes the hard sell, when he doesn’t. And we brought it. At the end of the 15 minutes he said ‘let me get some skin in the game,’ and the deal was done. We left the meeting saying, all fundraising should be like this.

The Lesson: Do your homework. Always. And don’t force something to fit, when it won’t.

Meeting #2:  Will you give me advice?

Backstory: We were dying to meet Alexis Maybank, one of the Gilt founders. We told her we were fundraising, trying to navigate our way, looking for mentors like her, hint hint.  She just smiled.

What happened: She told us her biggest advice was when you want something, ask. Want someone to invest? Ask them. Want someone  to advise? Ask.

The Lesson: Ask for what you want. Up until then, when we took meetings, we’d flirt around the issues on our mind—money, advisors, partnerships, advice. We assumed people knew why we were there and what we wanted, and were hoping they’d just bring it up. After this meeting, we realized if we wanted something, we had to be upfront.

Meeting #3: Will you tell me what to do?

Backstory: We got a chance to meet with Jon Steinberg from Buzzfeed. We had lots of questions for him on business development and management style. Read: Tell us how to do our job well.

What happened: Jon told us our only job was to fire ourselves.

The Lesson:  Fire yourself everyday. A good manager hires well and hires to fix current problems they’re currently multitasking. The goal is to fire yourself from those problems and move onto the next fire and the next big thing. We are very excited to be firing ourselves.

Meeting #4: Will you work with me?

Backstory: We had a meeting with a BIG brand.  Everyone told us it was a waste of our time, that 2 years would pass before anything would come from it, due to all the red tape. We went anyway.

What happened? We said we’re a startup, and we move quickly. They said if you had come to us 6 months ago, nothing would happen, but we’re ready to work with startups. In 2 weeks, we had signed and executed a partnership.

The Lesson: Work with people ready to work with you. Some brands say they want to work with startups and don’t know what that means, or don’t really mean it. You’ll waste your time to trying to make it work. 

Meeting #5 Will you give me a pep talk?

Backstory: We were lucky enough to meet someone in the space who not only gave us her time and contacts, but has become an invaluable part of our extended team. 

What happened:  A friend introduced us to our now advisor way back when. From then on, she has understood our company’s vision and our relationship as founders in a way no one else really has been able to. On cold days in February when we are very pale and very run down, she reminds us why we are good at what we do. And she means it. 

The Lesson: You need someone to support you when things are good and when they are bad who is not your mother, father, or spouse, and actually knows your business. We are lucky to have that. 

Our favorite position is CEO, too

We haven’t wanted to write this one. 

But yesterday we were interviewed on NPR (!). When we checked the website, we saw this in the comments section from a Gordon:

"Wow. So, with a million plus in funding, they produce a *newsletter* that gives me headlines? One can only politely speculate on the techniques they employed to drum up that funding. btw "career" is not pronounced "creer", ladies."

Thanks for that, Mr. G. 

Often times we are asked to talk about what it was like fundraising as two women in the industry. We firmly believe that fundraising is hard for ANY new entrepreneur —man or woman. That being said, we’ve had some interesting experiences along the way.

The following things happened during fundraising:

-We were asked if we shared a bedroom

-We were asked if we had any ‘crazy ex-boyfriends like that girl at UVA’ (the one who was MURDERED)

-We were told to make sure we find time to get married

-We were told (by a very famous feminist) to get a rich boyfriend to fund us

-We were told by a very famous female founder that she got a rich boyfriend and it helped her, when we repeated the story above

-We were asked who writes our sports coverage

-We were asked who we paid to come up with our business plan

-When we finished our round someone Tweeted:  ”Diligence consisted of: “Eh i dunno the one on the left is actually cuter than the one on the right…”

For the record: The only ‘technique’ used in our raise was a lot of hard work mixed with sleepless nights. We write our own sports coverage. We do not share a bedroom (Skimm B snores).

If you thought all of this was said to us by old men in suits, you are very wrong. Although some of it was. Half of these interactions came from other women.

Amid the huge push right now to support women in tech and for women in tech to help other women rise in the industry, we are incredibly grateful that there are resources for us to grow our network with female mentors. We’ve been amazed by the support system (of both men and women) that has rallied around us.

And we’re sure many people out there probably have stories a lot worse than these.

NEW ENTREPRENEUR LESSON OF THE DAY: Raising money is hard and scary. For men and women.  Especially first timers. And people shouldn’t  write or say stupid things.

Why We Said ‘Yes’

We’ve talked a lot about learning to say no. No to various opportunities, no to job seekers, and no to certain interview skills we’ve seen. But we’ve grown to a point in our business where we have to start saying ‘yes.’ Yes to opportunity and yes to people who want to build theSkimm with us.

We have now hired half of our team. Making our first hire was the weirdest thing we’ve done to date. We’ve been in our own bubble (literally—our apartment is quite small) and no one has had a stake in our day-to-day…until now. It is the most surreal — and special — moment to hear someone believes enough in what you’re doing enough to commit to take the leap with you and build it together. Hearing someone quit their stable job  to join us made us simultaneously want to vomit, jump up and down, pop the champagne, and get to work. 

The three people we’ve hired impressed us with their passion, skills, ideas, and plans for execution.

PS We’re still hiring for business development and editorial  


Ryan-Growth Skimm’r

What’s his job? To understand our user growth and strategize how to grow more

What’d he do before? Director of Analytics at Fab

Why’d we hire him? When we came up with this job posting, we thought about what types of problems this person would need to solve and what type of experience they likely had. And then we trolled LinkedIn and found Ryan—to say he’s the man of our dreams is awkward but Ryan fit everything we were looking for. He had a background in finance with experience in e-commerce, newsletters, and scaling. He is someone who likes to hear about problems because he wants to find innovative ways to solve them. His focus is on growth, so is ours. Match made in heaven.

Daniel-Developer Skimm’r

What’s his job? To make theSkimm user experience better

What’d he do before? Software engineer at Meetup; flew planes (NBD)

Why’d we hire him? Daniel has been a friend of theSkimm for a VERY long time. He has been our 911 call when things break, when we panic, and he still likes us. Daniel likes to build things and from day one has said he wanted to build theSkimm with us into a lifestyle brand that would transform the news experience. He is passionate about the product and our playlists and never says “No,” always “We’ll find a way.”

Kaylin-Community Skimm’r

What’s her job? To grow our base on college campuses and help with other grassroots outreach.

What’d she do before? Strategy consultant at IBM

Why’d we hire her? Kaylin is theSkimm demo. She had been a longtime reader and could explain why theSkimm was the right product to start her day better than we could—she embodied our brand and who better to sell what we are than the customer? But she also came with ideas and an execution plan. We’ve seen so many people come in with thousands of great ideas that are either not realistic or cost wayyyy too much money; Kaylin’s consulting background showed us she was a problem solver.

New Entrepreneur Lesson of the Day: Don’t rush into a relationship but when you meet the one, pop that question.

Fake It Till You Make It

Now that the fundraising process is complete, we can be honest: We had no idea what the F we were doing when we started. Our pre-Skimm lives had nothing to do with a business background. The following are things we learned that  may seem very obvious to many of you. But they weren’t for us. And they aren’t for many out there who are thinking about starting something (don’t let it scare you). 


What it means:  How much your company is worth before and after you raise money

How we learned it:  In one of our first meetings in the earliest of Skimm days we were asked what valuation we were raising at. We had never heard this term before so Skimm A held up her hand and put a few fingers down to indicate a number. We didn’t know if we were talking hundreds, thousands, millions, or giving up a kidney. Turns out it can be a bit of a made up number that everyone else like to judge you on.

Pitch Deck

What it means: Essentially your sales pitch presentation you send around, ask others to forward, and bring to investors to look at. It’s your vision and your plan in a few slides. It should get you the meeting or help you close.

How we learned it: Right around launch, a friend sent over examples of some stellar pitch decks. We created our presentation and thought it was brilliant and gorgeous. It was neither.  So then we met with some consultants who said they would do it for us. They’d write out our vision.  It wasn’t until  the end of our raise that we sat on a stoop eating turkey sandwiches and forced one another to present to the other. We realized that no one could explain our vision except, well, us. The rest is history.


What it means: An investor who likely puts the most money into the round and sets the terms for the deal. It’s a stamp of validation for other investors who want to make sure someone is invested enough in you.

How we learned it: An early potential investor asked us who our lead was and we said we were. We were leading ourselves. That was very, very much the wrong answer. We then learned that everyone likes to say they’ll give you money once you have a lead. It’s as fun finding one as it sounds. You should also seriously consider finding one you really want to have a relationship with because it’s compared to ‘a marriage’. Think about how picky you are just dating. 

Term Sheet

What it means: The terms of the deal as agreed upon with the lead investor.

How we learned it: When we had a signed one we thought our deal  was done and could break out the champagne. Our parents thought we were done and told the world. You are not done until the fat lady sings and your lawyers go through and edit the hundreds of pages of documentation that the term sheet is mean to summarize. You are engaged, you are not married—this is pre-nup time. Again, as fun as it sounds.

New Entrepeneur Lesson of the Day: Fake it till you make it. And have a few close friends and advisors who you can ask A LOT of questions.

The Good, the Bad, and the Ugly

Last week, we announced that we had raised a round of funding. We could not be happier about who our partners are and what is to come. We have been in full hiring mode since the announcement but have had time to reflect on the fundraising process.  Our next few posts will cover different parts of the raising process but here are some initial thoughts.

Things we learned:

Fundraising is hard.

Fundraising is really hard when it’s your first time doing it.

Fundraising is a lot like dating. It’s really fun to talk about the good ol’ days once you’re settled down in a relationship. Going through it, however, can be miserable

We went into the process admittedly naive. We thought we’d show investors the email. Some nice press articles. Give them a Skimm T. They’d fall in love. Money would be in the bank in three weeks. We’d all have a glass of champagne. 

That is not how it went.

The process was long, stressful, and brought about the first tears in Skimm HQ ever. But it was necessary and transformative. Being able to pitch our company to someone else forced us to rearticulate, redefine, and sharpen our vision for theSkimm. It turned us into better co-founders and co-CEOs. It brought us focus, tougher skin, and made us so excited for what we could get done with the right partners and funds.

Things that are great about fundraising:

You focus

You meet so many new people. We have developed such an incredible network of mentors through the process and never would have met them had we not been out there

You get more excited than you ever thought you could be about your company

It is very surreal to talk about more money than you ever imagined seeing in your bank account

Things that are not great about fundraising:

It’s awkward asking people for money and doesn’t get less awkward over time

People can be rude and condescending…especially during your first time

You are giving up ownership in your company

It’s very hard not to take things personally

You say your pitch so many times that you sometimes blurt it out while ordering dinner

Things we are happy we’ll never hear again

"Is this your first time raising money?"

"Have you even thought about your business plan yet?"

"Do you two hate  each other yet?"

"Who did you pay to put your deck together?"

"Who’s doing the raise for you?"

"Do you just do this on the side and have day jobs?"

New Entrepreneur Lesson of the Day: Fundraising is hard and it’s very tempting to hire people to help you. But it’s extremely valuable to do it yourself. It’s your company. Make it happen. 

Big News!

A little over a year ago, we sent the first Daily Skimm email out of our tiny apartment and prayed for the best (slash nearly had a stroke). And with that first send, theSkimm was born. All that has happened since has surpassed our wildest expectations.

We launched theSkimm because we could not ignore a big void in the market — we saw that our friends, who are highly educated and very busy, were not engaging with news in a way they enjoyed, fit into their routine, or made them keep coming back for more. As news producers, we knew we could fix this and had the passion to take it on. So we gave theSkimm a voice that would cut through the noise and that our target audience could connect with, using a delivery mechanism — email — that they already use daily.

Through the power of word of mouth, theSkimm has become one of the fastest growing e-newsletters to date with unprecedented user engagement. You — our readers — are waking up with us and Skimm’ing before your coffee, before you brush your teeth (thanks for that) and before you talk to anyone else… and then you’re telling your friends and co-workers about theSkimm all day long. We want to build upon that, which means it’s time to take things to the next level…

We have raised a round of funding.

This next year is about scale.  Scaling our user base in a way that maintains high user engagement and scaling our team from the two-(wo)man band it currently is. We are hiring a team made up of highly skilled engineers, a designer, business experts, growth strategists, and journalists to help us expand theSkimm’s reach. We will be focusing on improving the user experience, implementing key partnerships, and doubling down on strategic growth opportunities. We’re going to do all this with the help of a $1.1 million Seed financing led by Homebrew and supported by  RRE Ventures,  Troy Carter of  Atom Factory, Bob Pittman, Gordon Crawford,  Richard Greenfield, and our earliest angel supporters, including Lizzie & Jonathan Tisch, Nancy & Jeffrey B. Lane,  Five Island Ventures, and advisors like Dany Levy, founder of DailyCandy, and Laurie Racine, founder of Startl. We could not be more excited!

We chose Homebrew as our lead for Satya Patel and Hunter Walk’s unprecedented knowledge of product building at Twitter and YouTube and because of their obvious desire to help us build the company that we envision. We knew we had found the right partners when the four of us had lunch and each knew what the other’s co-founder was ordering.

theSkimm isn’t just about reading an email, it’s about living a Skimm life. Our goal is to redefine information consumption to fit into a streamlined modern routine and turn the news experience into an actual lifestyle brand.

How will this affect current Skimm’rs? It won’t, there will just be a lot more of you. Knock on wood. Oh, and the Daily Skimm will be prettier.

There are no words to adequately thank you — our friends, our mentors, and our family for all of the support over the past year and for appreciating the fact that sometimes we have a one-track mind: theSkimm.

To our Skimm’rs — we cannot thank you enough. To everyone else — better join theSkimm life right now. Seriously, go sign up.  And tell friends.

Did we mention we are hiring?

Anger Management

One of the most exciting things about starting theSkimm has been talking to bigger companies that would like to partner with us. But we recently had an experience we weren’t expecting.  In a ‘friendly’ conversation, an exec at a company said we could either partner or they would just make their own Skimm. And then smiled. 

Our internal reaction went something like this: areyouf*ckingkiddingme/ihateyou/theSkimmisours/youremean/ihateyou

But then we remembered a great piece of advice we received from a mentor who once had similar things said to her.

Just smile and say I completely respect that and wish you all the best.

NEW ENTREPRENEUR LESSON OF THE DAY: Know who you are and have confidence. Imitation is the best form of flattery. And shows you’re on to something. 



In startup land, it’s easy to fall into the trap of feeling like a college student. You’re running around, often wearing sweats, working weird hours, and eating a lot of junk food. But then there are those moments, where you feel for a brief moment that you are a big time successful CEO. Not going to lie, it feels kind of cool. And then you come back to reality. That’s happened to us with the following milestones.

First Business Card order

What you think it means: Have your people call my people

What it really means: I need a case for these things and I’m definitely going to misplace your card.

First Corporate card

What you think it means: ONE MILLION DOLLARS

What it really means: I can’t pay this thing off

When someone asks to talk to a different department on our team

What you think it means: One day I’ll have a team! And departments!

What it really means: It’s me, myself, and I. And my couch

When you tell someone you have to ask your lawyer

What you think it means: My team is made up of sharks and they’ll destroy you

What it really means: I have no idea the answer. And this just cost me more than my rent.

The Sexless Marriage

Last week, we went to an event and Skimm B ordered for Skimm A. Someone commented that ‘you guys spend too much time together. It’s like you’re  in a sexless marriage.” That got us to thinking, that we kind of are. When you start a company with someone you are basically saying ‘I do’ til bankrupt-do-us-part. We know each other’s likes/dislikes/breaking points/stress snacks/go-to drinks/Netflix marathon of choice. But like in marriage (so, we hear) the true test of a good partnership is to pick up the slack when one is down.

Exhibit A

Skimm B has a nut allergy.


The Scene: A meeting with one other person. Popcorn has just been consumed.

THE PROBLEM: SKIMM B TEXTS Skimm A. They are sitting next to each other.

SKIMM B: I think that popcorn had peanut oil on it. My lip is starting to blow up. Please note my epi-pen is in my bag. Benadryl is in my wallet. I’m placing my wallet on the table now.


SKIMM A: Roger, that.

THE SOLUTION: And without missing a beat, SKIMM A took over in the meeting, so SKIMM B could anxiously rub her lip. Team Skimm survived the meeting, with the other participant none the wiser. NOTE: Severe reaction was thankfully avoided.

NEW ENTREPRENEUR LESSON OF THE DAY: Make sure you and your co-founder are a team, in every sense of the word.

Party like it’s your birthday

Today is our birthday.  The big 1. This year has flown by in a blink of an eye and has been the wildest adventure we could have ever imagined. A year ago we sat in our very tiny apartment and pushed ‘send’ on an email, with no sleep, a lot of hope, and maybe a few drinks (yes, it was early). We have had even bigger rewards than anything we could ever have thought up as kids—the Today Show, Vanity Fair, a tour of “60 Minutes,”  invitations to breakfasts with our business idols, personal notes from readers on how theSkimm has impacted them. And some real stressful times (no need to talk about those!).


All in all, Year 1 has surpassed expectations and given us a lot to reflect on.

Things we’ve learned:

-how to make GCal invites

-how to set up a printer/scanner (ok maybe we didn’t learn this well)

-how to make financial models

-how to ask friends to help us make financial models

-how to ask what a pitch deck is

-how to make a pitch deck

-how to ask for money

-how to speak in public

-how to smile on camera without getting lock law

-how to recruit

-how to negotiate

-how to fire

-how to respond when someone says ‘you write like a dude’

-how to be managers

-how to network

-how to do business taxes

-how not to introduce one another as partners (turns out when you are two female founders, people may think you are lesbians)

-how to code (ish)

-how to turn a coffee table into a supply closet 

-how to win a fight with our cable company

-how to talk to strangers and give them Skimm cards

-how to make schedules to remember to shower and go to the gym

-how to sleep in shifts

-how to manage a love/hate relationship with Mailchimp

-how to embrace crying at the Genius bar

-how to accept that we are terrible drivers

-how to decide who to listen to and who to totally block out

-how to prioritize

-how to stick to a schedule

-how to smile when your credit card is declined in public

-how to convince people we don’t get sick of each other

-how to balance work and play (still working on this one)

-how important a support system is

-how important it is to know when to be humble and when to be confident

-how far we have come

-how far we have to go

-how “your” and “you’re” make people VERY passionate

From the bottom of our Skimm hearts—THANK YOU!