Chapter XVII

because you never know someone from the very beginning



Vacation Response

Almost vacation time! 

I cannot wait.  It’s been a while, a good year and now it’s time to recharge, unplug and gear up for autumn by powering down in August.  I will set an email auto-response that says something like “I am away through blah blah and if you need to talk to someone urgently please contact blah blah blah.”

This is factual and directive, but not that much fun. I am considering a few alternate responses:

“GO AWAY”** Tempting

“Out smelling roses. It’s the end of August. I suggest you do the same.” Too preachy?

“LOOK! Over there!” The art of distraction

“Got your email.  Maybe just hug it out.” Peace

“Sorry I missed you.  I am on the beach building sand castles with my kids who are three and six and if asked, think Mommy and Daddy spend too much time on our phones. In fact, they (and we) have decided that since we are away digging in sand, eating messy ice cream, playing chase and star gazing that phones/screens are a distraction and we will only be looking at them twice a day.  Consider switching places with us right now.  Would you like to take a call from me and interrupt your time with your three year old who’s experiencing mint chocolate chip for the first time?” GUILT

“I am away right now.  Everything will be fine.  There are very few actual emergencies and truly urgent situations.  Please review your emails from the last year.  In what percent of them did you use the word Urgent, include ALL CAPS in your subject line or choose the red exclamation point?  If you did any of the above in more than 5% of your communications, please go HERE.”

“I am on vacation. If the word ‘vacation’ is hard for you and you think less of me for taking time away please read THIS ARTICLE.  And let me rephrase, I am in the middle of task-negative pursuits. Talk to you in September.”


** An idea from my mother-in-law, a very direct and wise individual who, while maintaining a very active life, is also a master of all things non-screen and comfort-oriented.

Stranger In A Strange Land OR Being A Woman In Tech

In the last year, there has been a lot of talk about “the woman thing” and “the black thing” in tech – or specifically, the dearth of women and African-Americans in the technology industry. Is Silicon Valley/the Tech Industry racist and/or sexist? As a woman in tech who works at a minority run/founded/managed firm, I thought I would weigh in with a few thoughts.

First, broad sweeping statements only get you so far and are frankly not that interesting (Dramatic? Yes. Media generating? Possibly. Helpful? I am not so sure). The truth is, we can only speak from our own experiences and we SHOULD do our best to listen when someone else discusses what they’ve been through. The data tell a grim picture, to be sure. But the data doesn’t necessarily get to the root causes and more importantly, the solutions. When people tell you what they’ve experienced and how they’ve dealt with it, sit with that before judging or being dismissive. Gauge your own reaction. Does this feel familiar to you? If not, imagine what it would be like to be in that person’s shoes. I think that it is through this type of thoughtfulness that we will see change over time.

Here is what I know…

  • When my firm Ascend was raising our second fund we were asked “How much are you raising?” to which we replied “Target is $150 million; our first fund was $55 million.” And one time we heard back “OK. Seems like a lot for YOU GUYS.” Hmmm…you guys. What does that mean? As it happens, what we were raising was in line with industry trends at the time. Why would that have been a lot for us when we had the traction to back it up?
  • When I first entered venture capital, I made my way to a lot of conferences for entrepreneurs and investors. I would meet someone and introduce myself “Kylie Sachs with Ascend Ventures” So far so good, right? Well, sort of. It was pretty common that after my normal, standard intro I would get asked “Oh, what do you do for Ascend…marketing?” “Ah, nope.” “Are you doing HR and Admin for them?” “No again! I invest for Ascend. I am on the investing team.” I would bet that not too many guys had to tell someone at such a conference FOR INVESTORS that they were in fact AN INVESTOR. Just a hunch.
  • In a meeting with an entrepreneur a couple of years ago I asked how he thinks the open source community’s efforts would impact his business. He gave me a hand wave of sorts and moved right along in his presentation. 20 minutes later one of my partners asked the same question. The entrepreneur acted as if that was the question that would make or break his business, and then went on to wax strategic about open source for 30 minutes. I was dumfounded. Had he not heard me? Did I speak in a different tongue?
  • Recently I was at a meeting and a private equity guy looked at me across the table and said “Wow, so you are a working mother. What is that like?” There I was, like a stranger in a strange land…a working mother. A hush came over the room. Maybe it was silent because all of the other guys were reflecting on their own experiences as “working fathers”? What do you think? He then went on to say how he never “let” his wife work since there was no way she could make more money than the babysitter would cost. The table laughed. Awkwardly. Needless to say we didn’t spend much time on his original question. But I tucked into the back of my mind that it might be fun to ask a guy like him what it’s like to be a “working father.”
  • I had breakfast with a young woman who is an associate at a very well-known firm. She is the only woman investor. On the down-low she asked me if I think about wearing glasses or contacts to be taken more seriously (Yes, I have thought about that) and did I have any strategies for making my voice heard in a room full of men (Yes I do). She was dismayed that she was thinking about these things – she was a couple of years out of college and in her words “I’ve never been so aware of my gender than I am now. I really didn’t think I would have to think about this stuff.” Welcome.
  • Last but not least, I left a meeting a few months ago where the gentleman across the table, to whom we were pitching a business, would not look at me. Oh he said hello, but all questions and all answers and all discussion was with my partner, a man. He didn’t look like a Neanderthal. He just seemed like he didn’t know how to have a business discussion with a woman. I was prepared to move on after we left. But as we debriefed on the meeting afterwards, my colleague asked me if I’d noticed it and could I imagine working with that guy. Apparently I was not alone or being overly-sensitive.

We all have our stories and anecdotes. I don’t think a lot of the – let’s face it – White Men understand these types of interactions. They don’t think they are racist or sexist. They don’t know they are asking questions, making assumptions, introducing irritations to women and minorities that they simply wouldn’t ask/make with other white guys. We tell these stories behind closed doors because we don’t really want the White Men to look at us and think “Oh there she goes again playing the chick card!” Non-sequitur: Card? There’s a card!?!? Do I get benefits and discounts?

So in the end, what to do?

Does this matter? Of course it matters, of course it’s annoying, of course we would rather not have it this way. But it’s in my power to deal with it. There are big, structural ways to deal with it through women’s initiatives (ASTIA, Springboard, 85broads), outspoken awesome women like Rachel Sklar, African-American incubators, and generally greater exposure (like CNN’s “Black in America” series). These all get us part way there. The other important part is simply what we do every day as women and/or minorities in this world. We execute. We push ahead. We keep working and perform to the best of our abilities. And we try to avoid or manage jerks along the way.

Is our bar higher? I think so. Is that fair? No. BUT, I can scream and shout about that or I can be commercial about it. I choose the latter. The best defense is a good offense…particularly when you are dealing with a combatant who doesn’t even know he’s initiated a battle. If I have to work harder to be recognized and acknowledged, that means whatever I am working on might perform better than the competition because I am THAT MUCH MORE on it. And if that is the case, I (we) should win in the end. We will have more points on the board. And if that’s the case, more of us will be in the game. The outcome of greater focus on winning ultimately will be, winning.

Breaking Down the Barriers that Stop the Start-up…

I asked a question earlier today on Twitter – if you have an idea for a business, big or small idea, what is holding you back from starting that business?  I got a few replies, mostly around money or lack thereof, and also a lack of confidence that he/she could raise enough money to start the business.  The reason I am asking is actually to get to another question – how have people done it?  Starting a business is hard.  There are many hurdles.  How have people successfully addressed those hurdles? 

If you had a money hurdle, what did you change in your life to manage that?  Did you move?  Did you vow to eat ramen?  Did you use your credit cards? 

If you had a confidence problem, what did you change in your life to manage that?

So first, I am trying to get at what holds people back, then I am trying to get at the solutions – boring or even better, creative, that allowed people to move ahead.  It seems to me a lot of folks want to do something on their own, but for a variety of reasons they don't.  I suspect that a lot of issues that typically stop people are shared – and some people say "oh well, I can't do it" and others push through.  In the start up world we talk a lot about what makes a business successful – but we don't as often hear the personal stories behind the people who make it happen – what choices and trade-offs they chose to make to pursue their dream.  People love to say "I can't do it because of [insert excuse]".  Of course you CAN, you are choosing not to for some other reason.  Let's break that down and give people some real life ideas for how to make it happen.

If you have some thoughts on this, comment here or send me an email to  I would love to hear from you.  I meet a lot of people with interesting ideas who STOP.  I would love to help them move past that with some interesting examples of people who pushed ahead.

What I Wanted To Be When I Grew Up

The very first thing I remember wanting to be was…

A doctor.  I remember sitting in our house in Sodus, NY (so I was no more than 5) looking at an anatomy book (really) and thinking I should be a doctor.

And from there I draw a blank until maybe, high school, when I wanted to be in fashion.  So the list starting in high school, through college was:

  • Fashion Designer
  • Something else in fashion when I realized I was not really a designer
  • Architect (still in high school)
  • International relations person (no idea what I wanted to do) specializing in Russia (applying to college)
  • Domestic security expert (freshman in college)
  • No idea (sophomore in college)
  • Corporate lawyer (later in my sophomore year in college when I realized I liked to argue and wanted to make a little money)
  • Cosmetics industry executive (junior in college; this interest led to an internship at Estee Lauder in London, where I realized I could not focus on lipstick all day)
  • Investment Banker (senior in college.  for obvious reasons.  I wanted to make money and live the Wall Street dream)

So what happened?

First job out of college: Kidder Peabody as a junior investment banker.  Kidder was quickly sold to another company – I was in the last analyst class at Kidder!  So I moved to another firm – Peter J. Solomon Company, to be a mergers and acquisitions banker (a junior one – don't be fooled).  I could write a LOT about being a banker.  Bottom line: I loved it.  Worked my tail off averaging 80 – 90 hour weeks for three years.  Amazing training.  Shaped so many aspects of who I am professionally today (I think first jobs really do that).

And then what?  For another post.  But fun to remember where my head was a long long time ago.  Funny thing is, I am still interested in cosmetics, not really in law, definitely in fashion, am bummed I speak a little as opposed to a lot of Russian, would love to design our own house one day (though will hire a proper architect of course), and domestic security…well, no knowledge of that (my experience in NYC on 9/11 does not qualify).

And the story of what I want to be when I grow up continues with a few other things in the past including hip-hop start-up, a variety of jobs in the media industry, and now VC.

Of course, these are only JOBS.  One thing I have learned is that this question is not only answered with what you do for a living.  My current definition is MUCH more expansive.  

How do you / did you answer this question?

Interesting Morning So Far

What an interesting morning so far.  Over a couple of meetings, I have had discussions on the following topics:

How to sell a system/product to a school district.

Navigating your career when you are 22 years old and highly analytical but don't want to be an economist or a researcher.

The benefits and challenges of being a venture capitalist.

Why be a venture capitalist.

What it's like to work at a start-up.

Living in London as a 20 year old (I met someone who, like me, lived there for a summer and interned.  Life changing summer).

How to navigate working in a male dominated industry (and whether or not it's true that many men categorize women they work with as one of the following: their daughter, granddaughter, wife or mistress). 

As a mother, how do you balance Correcting with Supporting your child?

When trying to raise money for a company from investors, you must address these three points head on: the Problem, your Solution, your Traction.

What Obama's service initiative means for schools/parents/school administrators and students.

So, what's next?

How to Interview with a Venture Capitalist (at least this one)

There have been a number of people who have written blog posts about how to get a job in venture capital.  Here are links (Seth Levine and Fred Wilson) to a couple of the most notable.  These are good posts with sage advice.

I rarely write about work, but in the past several months I have conducted several interviews and have witnessed some patterns.  This post is about how interviewees can be more effective…at least with me.  Several of my points will extend beyond getting a job in venture capital to the overall landscape of interviewing. 

In addition to conducting many an interview, I myself have had millions.  At Goldman Sachs alone, I met 29 people; 14 in one day.  I got that job, and thank GOD after all that.  Cripe.  I have not always been successful getting the job but I have received more offers than refusals, and have learned a few things along the way.  In addition, part of my job now is to interview lots of people for my companies, and I get pinged all the time by people wanting to get into VC asking for informational interviews.  Bottom line, I have gone through this process on both sides many times and think I have learned a few things about what works.  So here goes.

Lesson 1: Say you want the job.  This might sound shockingly obvious, but I am always amazed at how often I meet people who don't tell me that they want the job, and most importantly, why they want it.  They may tell me once I ask, but my point is, why make me ask?  Everything you say in an interview should tell your interviewer why you are right for the job.  This comment varies by level and circumstance.  The more senior the role, the more the conversation is two-way.  And if it's informational, I expect that you are exploring and not necessarily trying to sell yourself.  But if it's a real interview, assume I am interviewing others for the job; therefore, sell yourself.  Try to stand out from the pack.  Why are you here?  What is interesting to you about this role?  Why are you a fit?  This does not mean you cannot have questions – you should – but don't make me wonder if you are even interested in the job in the first place.

Lesson 2: Act the part.  If you want a job in VC, you are often given the advice that you should go get operating experience and then after 15 years you can be a VC.  This is a good idea, and arguably, the best path, but most people I meet are looking for something a little more immediate than a 15 year plan.  And I understand that.  So what to do besides meet as many people as you can and get lucky?  You should still meet as many VCs as you can, but also, try to make yourself more lucky.  You can do this if you position yourself properly, meaning, act like a VC.  Send me deals. Go meet some entrepreneurs doing interesting things and see if you can connect me to them.  Introduce me to talented managers.  Send me an industry analysis and create an investment thesis around that industry. It's draconian but clean – be of value to me, and I am more likely to think you might add value to the firm.  You may be saying "Free labor!  Why would I do that?"  Take a lesson from lawyers and investment bankers.  They do it all the time, and it often reaps big rewards, meaning, they get the business.

Lesson 3: Before you implement Lesson 2, find out if I am hiring anytime in the next…two years.  Not a great answer, but it's reality.  If I don't have a new fund, I don't have more fees with which to pay you, and therefore, it will be really hard for me to hire you.  So you might want to focus your efforts elsewhere.

Lesson 4: Don't say you want to be a VC because you are entrepreneurial.  It's a cliche.  If you are entrepreneurial, start a company or go work for a start-up. 

Lesson 5: If you are looking for a job at a portfolio company and we have never met before, please do not say you are flexible and will do anything.  I have heard this from even the most senior people and it is frankly not that helpful.  I don't really know what to make of that.  I need executors.  Killers!  And my portfolio companies have real needs, so learn what you can about them and have a view.  I appreciate generalist skills, and young companies often need athletes, but saying you are "flexible" can be translated as follows "I don't really know what I want to do."  Don't allow yourself to be viewed this way!  You have to present yourself as something more than just flexible. 

And a few more things.  Do some homework on the industry for which you are you are interviewing.  It's incredible how many people don't do this. 

And show up on time.  Just my 2 cents.

Maternity Leave

I don’t really know how to begin writing about maternity leave.  It ends now.  Tomorrow is my first day back at work.  So let me start simply, with just the facts:

Pregnant, and months of anticipation; give birth; about 12 weeks off to recover and learn to be a parent; go back to work.

And now, the sub-text.  Tomorrow I go back to work.  People say things like "I hope it will not be too difficult"; "Are you OK?"; "Nice to have you back."  And the answers are, it will be manageable, yes I am OK, and thanks, it’s nice to be back.

But wow, what a period of time this has been.  It’s hard to know where to start if you want to reflect on this time off called maternity leave.  It’s not a vacation, nor a sabbatical.  It’s not easy but it was not as hard as I had anticipated (the having a baby and learning to take care of her, that is).  I did not know what to expect and yes, it took me by surprise. 

There were times of loneliness.  I was at home with a being that could not talk.  None of my friends were at home.  I talked to a being that could not talk.  For weeks.

There were times of guilt…the baby did, after all, sleep.  During those times, what did I do?  Hello, Oprah.  I never slept in (that was not possible), I rarely napped (not my thing) but I did spend a lot of time in very comfortable clothes (I would not go so far as PJ’s all day but it would have been possible).  I had been warned that it would be so bad I would not be able to find time for a shower or even to brush my teeth.  That did not happen.  I managed to take care of myself and then some, thank you very much.  I had no intention of losing myself completely, and if that meant she cried for a few minutes, well, so be it.  I figured letting her cry and pulling myself together, was better than no tears from her while I felt like a disheveled disaster who could not manage a shower. 

There’s more.  I had this funny realization one day that from now on, and for at least the next 15 years, yes YEARS, we would need a sitter anytime we wanted to go out on our own.  That is a change.  OK, so I can swallow that, but that is WAY different. 

And then we found a nanny.  I remember the first time we had her stay and babysit one night.  We went out for dinner. It was the first time the Big H and I had been out in weeks.  And it was glorious.  It was sushi and only two hours and it was heaven.

I could not and did not anticipate the feelings associated with being a parent.  I heard someone say that having a child is like walking around for the rest of your life with your heart outside.  And that is about right.  It’s like getting hit by a train in a really great way.  We look at her sometimes and just stare.  I love my friends, family and husband but can honestly say, some of my most memorable and engaging conversations ever are with her now.  And she cannot talk.  That is saying something.

I remember the first time I took her out on my own.  I caught a glimpse of myself with the stroller and freaked out.  That was me.  In the window.  With the stroller.  It was a Thursday and I was not at work.  I was wearing jeans on a Thursday, mid-day, walking around with my new baby.  As I was out with her, she started to cry.  And she cried loudly.  And I had to keep going.  I was in the drugstore with the crying baby and had to take a deep breath.  I was THAT LADY with the screaming baby.  And that was OK.

And none of this makes sense.  I can feel myself rambling.  But I am going back to work tomorrow.  This time has passed and I need to reflect on it.  And so here I am, reflecting.  Trying to pull these thoughts together in a neat package with a thesis is hopeless.  So I ramble.

And then there was the change from feeling like she was totally dependent on me, to liberation.  I could be with her, and then leave her with the trusted nanny, and know she would be OK.  This did not happen overnight.  She refused a bottle, and I thought she would starve.  Yes, starve.  The fear of starving your child is not easily overcome.  But one day after hiring the Trusted Nanny, I left the house.  Left her with the Trusted Nanny.  And 20 minutes later, said nanny called me and said "She ate three ounces.  Don’t worry."  At this moment I burst into tears.  I was in a restaurant a block away fearing my child would starve, and then learned she would be OK.  I was thrilled and sad.  Thrilled I knew she would eat.  Sad she did not totally need me.  I was not immune to the guilt this caused…"But shouldn’t I WANT to be attached like that?  What does that say about me that I feel trapped by this need?". 

I have since gotten over that.  I realized I am a better parent when I am confident these duties can be shared.  I don’t think this makes me a bad parent.

The interesting thing is, I did not realize how scared and clueless I was until now.  Now I am much more confident with her.  If maternity leave started now, I would do it differently because I can.  I did not realize then how lacking in confidence I was until now when I actually feel more confident.  I wonder if this phenomenon will continue as she gets older.

But it’s funny.  It’s only been three months, and I am much more confident, and am OK leaving her with the Nanny while I go do something else…but I still miss her even now as she sleeps in the next room.

I am a nostalgic, sensitive, feeling person, but damn it, I never thought I would be this sappy.  I am now embracing my inner sap.  I am, after all, sappy.  It could be worse.

And now it’s time to learn to be a Working Mother.  I have read about this experience before.  I have heard women talk about it.  And here I go.  I am at the top of the water slide called "Working Mother"…you know, the kind where you can see the first bit but not much thereafter, and you pray there is a cool welcoming pool at the other end.  I am thankful I have a great job. If I didn’t, I would be miserable. 

I am now bittersweet.  I am sad.  I am moving to the next chapter, but yes, I am sad.  First Child Maternity Leave is a time of unexplainable emotions, and therefore, rambling blog posts with snippets of thoughts and reflections.  I wish I could go back to many of the moments I had.  It went too fast.  She is already in size 2 diapers and though this is trivial, it is yet another example of time flying.  The only answer to any of this, the somewhat melancholy piece of having a child, reflecting on the early days and going back to "real life" is the lesson that applies to so many things…to Be Here Now.  Focus on the immediate and relish every bit of it. 

Letting Go…temporarily

I packed a bag last night for the hospital.  That was very odd.  To plan to take a bag somewhere and come back not just with the bag but with a kid.  Surreal does not begin to describe the feeling.

Even more odd is how to deal with work.  I am directly involved with seven companies at my firm, a mix of east and west coast.  While I am out, certain responsibilities have to be "transitioned" to others.  This phenomenon, though temporary, is very unsettling.  Don’t read that wrong – I am thrilled to work at a firm where we plan for these things and people are willing to take the ball when I pass it.  But just the same, I am not typically one to ask others to do things for me, to take over, to manage something I feel is primarily my responsibility.

I guess the answer is "Get used to it" because when I come back I will be transferring some of that other responsibility – motherhood – to someone I don’t even know yet.  Someone I – WE – that being the husband wife unit – DO NOT EVEN KNOW yet.  That is going to be very very odd.

But for now I will focus on work.  I am trying to tie up lose ends, get things in order, allow for an easy transition.  We’ll see how it goes, and I hope that what comes around (what I ask for) goes around (I can return).  I suppose this is what would happen if a man had a heart attack, or had to take a leave for some other reason, but let’s be honest, this is about the realities of women in the workplace.  And I thank my lucky stars every day that there are people here who get it, offer to help, seem excited to carry the ball for a while and are generally supportive. 

But all that said, it goes against the grain for me, and it still feels odd, uncomfortable and weird.

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