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. 

We’re hiring—A Developer

theSkimm is looking for an all-star developer. Please send resumes to

Title:  Fulltime Fullstack Developer with Java/Groovy Experience.

Requirements: Comfortable with Ruby, PHP,   HTML/Javascript and CSS.

An ideal candidate has:

- Background in writing backends that are scalable and perform well under sudden spikes and without too much intervention.

- Experience dealing with Grails/Groovy and the Java language.

- Solid knowledge of HTML, CSS, Javascript

- Experience working with AWS (Amazon Web Services) infrastructure and scaling services such as load balancers, autoscaling groups and RDS database.

- Comfortable changing between front and backend programming as needed by the company’s growth objectives

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.

Advisors Anonymous

A note on advisors…

The first week we started theSkimm, people asked us who was on our advisory board. We said we didn’t have a board yet, not realizing that an advisory board is entirely different than a board of directors.

We quickly learned that just like the word ‘equity,’ people throw the word ‘advisor’ around very casually and it means different things to different people.

What should it mean to founders? Someone who is involved with the company, who is not an employee, and who is not necessarily an investor. But is more than just a friend. Someone who will get equity. Someone who can offer expertise or be able to help in a specific area of your business. And someone who can and will give you time. 

This is what we’ve found it can mean to other people.

Scenario: “Hey, Skimm A and Skimm B, we went to college together and I’ve been working in finance for a few years now and so I know a lot about deals and things. Give me some equity and I’ll advise you.”

Takeaway:  This person has never worked with startups. This person doesn’t know what they would be advising on. 

With every industry becoming more and more entrepreneurial, more and more people are trying to get their feet into the startup scene—and position themselves as experts, when they may not be. 

Scenario: An interview applicant said rather than join the team they would love to formally advise us so we could learn from their “business acumen.”

Takeaway: This person has about 3-5 years work experience in junior and mid-level positions. Sometimes people need to check themselves.

Scenario:  A very well-connected and influential person who could be very helpful to us informed us they would not make one introduction on our behalf without an advisory agreement.

Takeaway: There’s a fine line when it comes to gaining access to someone’s rolodex. There’s the stage of general and generous intros and then there’s a stage when someone becomes a professional networker for you. The latter stage is usually an advisor. The first stage is a normal human.

Scenario: A serial startup advisor said they’d love to get involved. For 8% of our company.

Takeaway: HAHA.

Scenario: "I’m advising all the companies in your space. And actually plan on starting my own company just like yours!  I should advise you too!"

Takeaway: Too close for comfort.

Scenario: I’d love to advise you. You can use my name. But I have no time to talk to you ever.

Takeaway: Sometimes it is helpful to have advisors for name recognition and credibility. But at a certain point, you need to realize what it means to give someone a piece of your company and a name can only help so much.

New Entrepreneur Lesson of the Day:  Focus is as important here, as in other parts of your business. Know what areas you need help in and line up advisors who are different from one another and can give you the time you need. Each relationship will be different but each should have a distinct value to the company.

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.

Flair or not to flair?

2014 is already a big deal at Skimm HQ. We will have our first office and our first employees start (today!) and the two-(wo)man team known as Skimm HQ will be no more. We’ve been preparing ourselves for what it means to grow a team and create a company culture. And have been thinking a LOT about what type of CEOs we want to be.

We’ve heard horror stories. Like the time we went to one office where all the employees had to wear black flat shoes because the CEO liked to be the only one in bright high-heeled shoes. Or the one where the co-founders would only take meetings while they were on their TrekDesk.

We’ve been compiling some of the best advice we’ve gotten over the years from our former bosses and managers, our current mentors,  and fellow business owners. Below are some of our favs. 

- The best CEOs respond to email themselves. Quickly.

- There is a known balance between work and life. Find it. Hold onto it.

- There is also a known balance between when a boss is a friend and when a boss is a boss. 

- Be a leader — an organized one

- Know what your team does on a daily basis

- Put a name next to each task you want done

- Be a mama bear when it comes to protecting your team

- Look out for the future. It’s coming. 

- Focus. Focus. Focus. So others can as well. 

- Make sure your office is inviting. No one wants to wake up and go work some place that makes them sad.

- Incentivize your team by thinking long term

- Read “The Secret” — again. You’ve got to see success to be a success. Or something like that. 

- Say ‘thank you’ 

-Your team needs to believe in you and see you confident. If you don’t know an answer to something, come up with one

-No one will care about your company more than you. But try and make them.

We’ll let you know how our transition goes this year. We are currently looking into having a long table instead of a TrekDesk and making Friday meetings BYOB. Thoughts?

How not to get a job at theSkimm

We are very excited to add to our Skimm team in 2014 and so thrilled with the new hires we’ve already made. We have been interviewing a LOT of people. Turns out it’s actually not more fun to be on the other side of the interview process. 

Putting aside everything that’s about to follow, the biggest takeaway we have from the job application process is how amazing it is to see how excited people are to join our team and how much they believe in theSkimm. Truly, nothing has meant more to us than that.

Things we’ve learned:

  1. An interview is as much about you interviewing the candidate as it is for them to interview and learn about you. Both sides need to bring their A-game and want it.
  2. People need direction and it is hugely important for the employer to lay out what they expect from this position. 
  3. Negotiating is an art. And you (the employer) will be very bad at it your first few times.
  4. People need to hear your short term goals and long-term vision. Share it. Make them excited.

The process has also brought to light a lot of major mistakes we’ve seen from potential candidates. Examples below.

Things people need to learn:

Skimm A: Hey I like Applicant X  and Y. Did X send in a thank you note?

Skimm B: Nope.

Skimm A: OK, let’s talk to Y.

      *Thank you notes

Your parents weren’t just being annoying when they made you write them. It seems like such an obvious thing to do but so many people do not take the time to do it. We literally have a column on our interview spreadsheet indicating who wrote a thank you note and who didn’t.  First, they show you have manners. And if you are talking about a role where you will be representing the brand and interfacing with clients, these are things we are are paying attention to. Secondly, they show an interest in the product and the know how to follow up. 

    *Apply for a specific position

Applicant: Hi I have a lot of talents. Let me know where I’d be a good fit.

Early startups have very specific problems that need solving. Positions are specific to skill sets that can offer solutions. Having us do the work to translate your talents into positions we’ve already posted doesn’t make us excited. This is a big mistake Skimm A and B made in pre-Skimm lives when applying to jobs and something that is very annoying to see on the other side.

      *Apply for the right position

theSkimm: Hi, what are you applying for?

Applicant: I’m a college senior and I’m going to be your head of Business Development

theSkimm: We have an entry level position you may be better suited for

Applicant: No, no, I have a lot of experience

We have gotten so many applications with people saying they are interested in both our most senior role and our most junior role. That is a big red flag.  If you are graduating from college this spring, you are likely not qualified for a senior role. 


theSkimm: Thanks for applying! Please send us a sample Skimm in our voice 

Applicant: Sorry, I’ve been writing so many applications I’m not interested in doing another writing sample.

theSkimm: Goodbye

We ask most candidates to complete a homework assignment. This is a test to see how you think, that you can complete tasks specific to the role, and that you can meet deadlines and follow through. Getting your trial homework in late is not a good start.

For editorial candidates,  we ask them to write a sample Skimm in our voice. This is to see they can master what we do on a daily basis.  When candidates write it in a different format or ask to see examples of our format (read: try signing up for the email) it goes to the “No” pile.


theSkimm:Thanks for coming in! Would love for you to tell us more about yourself

Applicant: Let’s actually start with you. How did you get investors to give you money?

Candidates are 100% interviewing us as much as we are them (see above) but there’s an art to doing that. We are the first to say we are new at this, that this is an early-stage company, and that we are learning a lot. But that doesn’t mean we aren’t professionals. We have had too many meetings when the interview asks us questions like “do you really think this is a business?” Yes — one you won’t be joining. 

    * Know your stage

theSkimm: Tell us what you’re looking for in this position

Applicant: Well I don’t do ad sales, I hate powerpoint, and please never ask me to deal with Excel.

Startups are not for everyone. That’s OK. Early stage startups are definitely not for everyone. Sometimes people forget that.  They weren’t for us pre-Skimm lives. When you list all the things you don’t want to work on, it’s a sign you are not cut out for the constantly changing environment of a new company. It’s fine to know these things but should also help you redirect your job search to something more stable.


theSkimm: We’d like to make you an offer

Applicant: Great, I’d like to be paid $200k and have 8% of your company. 

No one joins an early stage startup for the salary. It’s very common place for compensation to be a mix of cash and equity and as a new company we have decided to grant all of our first employees equity, as a sign we are invested in them as much as they are in us. If you’re looking at a startup, see how much money they’ve taken in, how many people they are hiring, and do the math. And know, there are no “departments” yet.


Applicant: I’m 110% taking this job if you offer it

theSkimm: It’s yours.

Applicant: Actually, I’m up for a big promotion at my current job and probably would want to get that first.

  The best kinds of candidates are the ones that are very candid. Honesty about what you want out of the position and if you’re talking to other companies is totally OK. It does no one any favors—on either side of this process—to lead someone on if you’re not serious. 

    *Start what you finish

theSkimm: Great chatting! We’d love to take next steps

Applicant: Well, I don’t  know if I’d take the job if I got it 

While this may seem contradictory to the point above, this one is for the benefit of the interviewee. It is always best to go through an interview process just to see what happens.  We benefited from this in our pre-Skimm lives and recently tried to return the favor and helped a candidate who wasn’t right for us get a new job. She starts next week.  

      *Know how to lie

theSkimm: Great to meet! What do you think of the product?

Applicant: It’s meh.

Again this may seem contradictory to a point above but there is an art to lying in an interview. When we ask what you think of the product, you might want to make us feel like you like it. And when we ask what you want to do we aren’t impressed when you say “I have no idea.” We are all figuring it out but there’s a way to artfully do it and sometimes it involves a fib or two.

        *Know the time

theSkimm: We’d love to talk with you about opportunity to join our team

Applicant: That’s amazing! I really like my job now  so can I join in a year?

Startups move very quickly. A year in startup land could mean new funding, acquisition, or disbanding. Waiting too long to act means missed opportunities. We’ve made the mistake of waiting too long to close a candidate and losing the opportunity and many applicants have made the mistake of thinking our needs now will be the same a year from now.

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. 

Up that resume game—-Insta-Gram style

If you’re thinking of applying for a job at theSkimm, better up that resume game, because Skimm A’s Grandma just applied. And we’re impressed.  See below:


To whom It may concern:

I hereby offer my services to any and all interested parties (even those not interested).

My qualifications are as follows:

  1.  I don’t drink, smoke or sleep on the job (except on weekdays).
  2. I take minimum amounts of time for lunch breaks and for normal restroom visitations (except when I really have to go)
  3. I smile often and nod my head in agreement even when I disagree with decisions made by higher-ups in the firm (which will probably be often.
  4. I wear attractive and well fitting attire with a demure aspect so far as colors are concerned (altho I’m partial to red, purple, green, yellow and pink all on one outfit).
  5. I can type with the best of them (also with the worst).
  6. I wear drugstore glasses (I’m cheap!)
  7. I’m a Democrat (in moments of need)
  8. I’m a Republican (under duress)
  9. I’m usually an independent (for what it’s worth)
  10. 11. My bank account is nil but I’m hoping to get a salary soon (is this a paying job?)
  11.  I don’t know anything about your company but I’m sure I’m right for this job)
  12. Call me soon as I’m much in demand (oops!  I forgot my e-mail address) (I’m old!)
  13.  When do I start?

Also known as Insta-Gram