Full Ratchet

I’ve landed back at SJC yesterday and put in a full today of start-up reviews, including our Monday morning management meeting (really just a chance for our founder to show off) and made the mistake of going on a date on a Monday night.

My trip home to Long Island — and specifically seeing my mom in such a physically weakened state — definitely helped reset some priorities, and I’m even more motivated now to find and help fund startups in the biotech or healthcare space that show promise in making cancer patients’ lives easier. Or really any type of patient. I know they’re out there.

I also still believe the right guy for me is out there, but it certainly wasn’t who I went out with last night. Let’s call him…Smarmy. Hi profile made him seem normal: claimed to be a pharmaceutical sales rep who loved sushi, stand-up comedy and traveling the world. I am purposely trying to avoid guys in the tech/startup/VC/PE/banking scene, so Smarmy had already cleared that hurdle. And I like sushi and stand-up…though not necessarily at the same time.

But when I showed up at Mitsunobu, my spider sense tingled. Something was off.  First, Smarmy had arrived before me, was already seated and was talking to a guy at another nearby table who I know to be an i-banker. He also looked about 10 years older than the pictures on his profile. Now, both of those things alone wouldn’t have been enough to bother me except: 1) when I questioned how he knew the banker, I learned that Smarmy had “forgotten to update his profile,” had left the pharma sales role months ago and now was at a biotech startup, and 2) he was purposely being cagey about his age when I started talking about my high school reunion and asking if he’d ever been to one of his. Why was he acting like this?

After he downed a few cups of sake like an uncultured a-hole, he went on to divulge that he was very veryrecently divorced — and it sounded ugly. He also had two young kids. And of course there had been no mention of them on his profile, either. 

Again, I’m not saying that I’m taking divorced men or men with kids off the table, but if someone’s already dropped 4 major lie-bombs on me within the first hour of our date — and they’re about critical things like YOUR JOB AND YOUR FAMILY — then hey, it’s not going to end well. I’m pretty sure when you try to sell a used car, you have to disclose its accident history. Just sayin’.

Per usual, I had Alice call me about 45 minutes into dinner so I could make up an excuse to leave, and I did. Now that kind of lying is OK with me. Sayonara, Smarmy.

Ah, well. Another one bites the dust. But I hold out hope for my date/meet-up/whatever it is with Nice Guy Cooper from my high school reunion … and then of course I still have tentative plans to see my college ex Chris again in a week or so, even though obviouslynothing is going to come of that except the satisfaction I’ll get from rejecting him ever so not-subtly. Onward.

I’m still on the east coast where I’ve been working this week from our New York “office” (well, a WeWork goldfish bowl in midtown with nice free tea and gross free beer…more on that later), but for now, here’s a rundown of my day…

4:30 p.m.

I have of course waited until the ultimate last minute to decide if I’m really going to go to my high school reunion. I’m frustrated with myself because I cannot figure out why I feel so nervous and conflicted — I mean, if I’m being blunt, I deal with a lot scarier people on a daily basis at XL.

4:45 p.m.

OK I decided I’ll go because I’m hardly ever back home and it seems dumb to skip it since I’m here, but now I’m not sure what to wear so I don’t stick out as “the one from the othercoast.” Have gone through three outfits already but I just really didn’t bring back that much to choose from. Argh.

5 p.m. 

OK I’m leaving in my parents’ car and went with a basic-but-safe black dress pants and nice short-sleeve top with minimal jewelry combo.

5:30 p.m.

I’m here in the parking lot of this hotel the reunion’s at, once again having doubts, but I’m just going to force myself to go in. It’s not like I was unliked or had no friends or something, but I really haven’t kept up with anyone and feel like my life is so drastically different now and SHUT UP SARAH JUST GO.

7 p.m.

Jotting this down from the bathroom stall (classy, I know): this night has taken an unexpected turn. In a good way. The first hour was lots of small talk and fake smiles and trying to not stare at name tags too long to give away the fact I remembered almost no one, but then about 30 mins ago this guy comes over and he knew who I was … from work. As in, he’s also out in the Valley at a PE firm that I’ve heard positive things about. He had seen the press release about me joining XL and it sparked his memory and he said he was hoping I’d be here. He seems normal and nice… ? He said he only transferred to our high school during senior year. Maybe that’s why I don’t remember him?

9 p.m.

Wow, this night was not what I feared it would be at all. The PE guy — his name is Cooper — asked for my number so we can connect when we’re both back in California. But it wasn’t like he was hitting on me … it was like he was just a normal human being who happened to be a good-looking single male who was wanting to hang out again. And I found out he transferred high schools from the Midwest, so that’s probably why he’s so nice.

10 p.m. 

Wow I just got home and Cooper actually texted already just to make sure he had the right number. I don’t know what’ll end up happening when I’m back home, but this reunion was definitely worth it no matter what at this point. I’m glad I went. One more day here with my parents and then it’s back to the “real” world, if you can count the Valley as in any way real. But now at least I have something kinda interesting to look forward to: I have plans with Cooper on Thursday night. 

I didn’t want to admit what might be going on here, but now there’s no denying it. When I finally had some time to catch up on social media feeds during my mom’s chemo treatment earlier this week, I noticed that Chris — my college boyfriend who I thought was “the one” for years, until I found out he’d been cheating on me for a few months after graduation — just reconnected with me on not one, not two, but basically allthe platforms. Facebook, Twitter, LinkedIn, IG, you name it.

I was like “WTF”because he ended up marryingthe girl he was cheating on me with. But then I got distracted and pulled back into reality when my mom’s doctor came in to chat with us. The chemo is taking hold, but it’ll be a long, uncertain road and I can tell that she’s scared. Truth be told: so am I. Dad’s taking some leave starting next week, so Mom will have someone at home with her to take her to treatments.

After she fell asleep, I put the earbuds for five hours of conference calls. Not only does the Valley work 16 hour days, but they’re 3 hours behind the East Coast, so I didn’t hop off until well after midnight.  But I got through Li-Sa’s new branding proposal, the XL investment review, Jonathan Roper pitching me a new start-up (software that writes software), and the CFO of one of our companies who somehow burned over a million dollars in three months.

It’s now nearly 2 am and I’m finally heading to bed (STILL in my childhood room … I’m staying here through the weekend to go to my high school reunion, which I hope I don’t regret) I just checked my personal email and see that Chris wrote me yesterday, saying that he will be in San Jose in a few weeks and wanted to know if I’d be up for dinner. Hmm.

Then I checked his Facebook and, sure enough, all pictures and mentions of his wife have been scrubbed, and it looks like he’s back on the dating scene. I didn’t scroll back far enough to see if they had any kids, but so far it doesn’t look like it.

I know better than respond right now at the end of a long day, and I also know better than to respond before I have a chance to discuss this with a more objective friend (namely Alice). But there is definitely a big part of me that doeswant to see him again after all these years, if for no other reason than to bring some closure to the whole mess once and for all. 

I mean, I’m pretty sure that’s why I want to see him. 

Yeah … gotta talk to Alice ASAP about this.

I’m writing this while sitting up.in my childhood bed, in my childhood room, in my childhood home. It’s kind of amazing how all I need to do is set foot in my parent’s house and I can feel myself regress. We all fall into our old patterns from when I was a teenager, with my dad gently scolding me about needing to eat more vegetables, and my mom warning that I push myself too hard. And both of them still wondering if I’m dating someone I’m not telling them about.

But the biggest difference on this visit is that I have no choice but to feel like an adult. I’m here to go to a chemo treatment with my mom, and I had to stop myself from gasping in shock when I first saw her. My parents aren’t ones for Skype or FaceTime, so while I’ve been talking to them regularly for months, I haven’t actually set eyes on them since I went to my mom’s very first chemo treatment with her four months ago. And now I regret not coming back sooner. She’s lost a lot of weight and just seems diminished … smaller. It’s terrifying.

Thankfully her attitude doesn’t seem to have changed. She’s still determined to beat this thing, and she seems like she still has a decent amount of energy. But that didn’t stop my Aunt Patty — mom’s sister — from making me feel like shit when she picked me up from ISP. Going on and on about “Why’d you have to move across the country?” and “Can’t whatever it is you do be done from New York, for god’s sake?” I kindly reminded her that Big Sis was also in California … with my parents’ only two grandchildren. But honestly, trying to deflect Patty’s wrath onto Big Sis’ didn’t make me feel any better, or less guilty.

We have to be at the hospital early, and it’ll be 3 hours earlier to this poor jet-lagged body and mind of mine. Luckily mom left dear old Flopsy on my bed (my beloved, battered bunny from back in the day). It’s weird how this little stuffed animal is so oddly comforting to a grown-ass woman. But I’ll take it. It’s times like these that I’m glad mom doesn’t throw anythingout.    

I’d been looking forward to this night out with Alice all week, and it did not disappoint.

First on the agenda was dinner at Madera in the Rosewood, which would normally be too scene-y for my taste when I want nothing more than to forget about work on a gorgeous Friday evening, butit’s Alice’s favorite restaurant (I think she has a crush on Reylon, the (very handsome) head chef) and this night was going to be about her, so I rolled with it. (And it really is so, so good. I tried to ignore everyone surrounding us who I either knew or thought I might know.)

Then we went next door to The Library & Bar — one of myfavorite places — for drinks. We miraculously managed to get a seat out on the terrace (OK maybe I pulled some strings … again, for Alice) and were able to finish up our convo from dinner about The Idiot (I will not speak his name, he’s just going to be The Idiot) who broke Alice’s heart after she slowly but surely fell for him over the past six months.

I had met The Idiot a few times, and I, too, had been fooled into thinking that he seemed perfect for her. They’d been set up through a friend, he was NOT in the tech industry (a teacher!), and while in retrospect I guess he might have felt a little out of place with our usual crowd, he treated Alice like the queen she is.

And then poof!He ended things, and she still has no idea why.

I wasn’t sure what to expect from her tonight. She’s not usually one to let her emotions rule, but over I knew she was hurting. What I got was a few tears at first, then some bewilderment, and then the defiant kick-ass woman I know emerged once again — still nursing her wounds, perhaps, but confident in who she is and the kind of partner she wants and deserves. 

We got approached by a couple of guys from Sequoia (the Rosewood is across the street from their office, it’s basically their canteen), but she was in no mood to flirt and I was annoyed that men even attempted to bust in on what was clearly a deep conversation we were having. Overall, we had a great, great time, talked late into the night, and then got another date down on the books that’s actually not months away for once. 

I know she’ll be OK, and I’m so happy we had this bonding time. But now there is a little voice in the back of my head asking, “If The Idiot seemed so wonderful for so long and then ghosted with no explanation, are either of us ever going to find someone we can truly trust?”

The biggest surprise to me from flipping over to the VC side of the table is how many pitches are terrible.

When I was on the other side (At Hi5, we took three rounds of venture funding, and probably pitched over 200 times to get those three rounds), I’d just assumed that everyone who turned us down was inundated with perfect pitches, but boy was I wrong!?

Right now, I’m taking about 5 pitches a day. I set up in the XL conference room with my S’well battle, an extra-hot turmeric latte, and a notebook (I’m surprisingly old-school like that). The founders file in for 45-minute meetings all morning.

Without naming names, this morning I got…

• Rent-The-Runway for ski gear (not bad, but too niche);
• Netflix for Books (nobody reads anymore);
• Uber for podiatrists (um, thanks but no thanks);
• AirBnB for rest-rooms (would people really rent out their toilets?)

Every founder was a guy, all white, and I could guess got a GroupOn voucher for bulk buying dark hoodies. These guys were all Zuck wannabes.

And then, finally, a Queen-Bee walked through the door.  She pitched a home nutrition system that was basically Nespresso for food. It was hardware plus software and met a huge pain point…what to cook for dinner?

Queen was dynamic, well-prepared (fact: female founders need to be twice as good as guys to even get half as much money), and committed. 

She demonstrated the machine (like a high-tech version of my mom’s crock pot) and each meal came with a QR code, which the machine used to calibrate itself. Maybe because it was bumping against lunch time, but the steamed salmon and new potatoes were incredible.  I also tasted the Chicken Kiev and it melted in my mouth.

The whole system needs a brand name, and some slick marketing, but Queen is onto something. 

I offered her a 2.5 pre-money valuation and a Series A injection of 2.5 to get to market. She agreed on the spot and I leaned in to shake her hand… Queen gave me a hug instead. 

She said I was the first female VC she’d met on the funding round and most of the men nodded, smiled, and either rejected her outright or said, “I’ll run this by my wife.”

It’s my first investment at XL and I can taste that it’s going to be a winner.

I just left Big Sister’s house. And I’m not even sure how to describe how I’m feeling right now. Mortified? Terrified? Incredulous? Sad?

I was there to spend time with my niece and nephew — and, of course, my big (I’m not “allowed” to call her “older”) sister. Just a little time before dinner and then dinner itself. And I don’t think enough Opus One exists in the world to calm my nerves after what just transpired.

Jackson and Janica are three-year-old (IVF) twins, whose shared operating system seems to be set to havoc mode. The wreak it on themselves, on each other, on anyone around them, and most definitely on Big Sis’ newly remodeled Mountain View house. It was just like a whirlwind of screaming and tantrums and fighting and accusing and crying and stomping. Basically, it was like a board meeting for a start-up facing a down-round. But with more snot. 

Little Jackson has So. Much. Energy. Even though their (faux Frank Lloyd Wright) house is crazy-huge, there was just not enough space to contain this kid. He wanted to run-run-run everywhere, and he was sliding all over their hardwood floors, crashing into Janica and their dog and their furniture, and wanting to show me all of these spinny-top battle things he has called Bey-Blades, which had nothing to do with Beyonce. 

Which I guess I gladly would’ve played with him had Janica not been tugging on my skirt and begging me to help her with her sticker book. Then she stole one of Jackson’s spinners and all hell broke loose. I couldn’t believe that Big Sis just kept on working in the kitchen like she didn’t hear World War 3 erupting a few feet away.

The funniest part was that she had this emo-vibey instrumental music playing on their sound system and I was thinking, “My dear sister, that is NOT doing anything to calm these hellions down.”

It did make me wonder about embarking on this whole single-parenting journey. Could I really handle all of this — alone? I mean, Big Sister seemedall chill, but the reality is that not only does she not work, but they also have a nanny from 9-5 to help her with the kids, errand-running, housework and chores and all of that. 

I realized that Anders has a built-in support structure that I might never have. He and I work the same hours at the same insane pace (though of course he was conveniently MIA tonight), butIwon’t have a spouse taking care of everything for me at home. He can pretty much just focus on deal flow and know that everything at home is handled. It’s not exactly a fair fight. And to be honest, I kinda resent Big Sis for enabling him to be laser-focused on his career. And I think she’d be more than judgmental of my ambitions to have kids without a partner.

So…I don’t think I can tell her about my egg-freezing plan anymore. But I will stop worrying about that for now and concentrate on finding some wine. Or maybe a shot of tequila. 

So I’m in a Lyft back to the office after having my first meeting with my fertility doctor, who I shall call Dr. Freeze from here on out, about this whole egg-freezing business. Half the time I felt like she was speaking another language — SO MANY new acronyms and terms and drug names to familiarize myself with now. I have to keep enough acronyms straight at work… do I really need to have more in my life? 

I guess I didn’t fully realize how extensive the process is … or how long it takes just for one cycle, which might only result in a few viable eggs when it’s all said and done. Yet in the waiting room beforehand and then later when I was checking out I witnessed 5 men who were clearly either sperm donors, partners or husbands being led back to “special” rooms where they could each make their, uh, contribution in about 5 minutes flat. 

Why oh why can’t I just fantasize about the hot priest from Fleabag and pop out some eggs??? Why do self-injections with two-inch needles have to be involved? Gah. 

Anyway, the good news is that I left feeling excited and hopeful — and confident that this is the right thing for me to do and the right time for me to do it. When I was waiting for my ride I saw a flustered woman in the parking lot struggling to get her flailing and screaming kid in a car seat while also juggling the keys, a sippy cup and various other kiddie paraphernalia. But it didn’t scare me. I know if I do end up having to go this route alone that it’s not going to be easy, but I’m not willing to give up on the vision I’ve always had for my future, which includes both a career and at least one child. 

Now I just gotta figure out how in the hell I’m going to set up all of these time-sensitive appointments around my work schedule — board meetings don’t have a “stop for Sarah’s biological clock” agenda item — and if I’m going to tell my sister (or anyone else, for that matter) about what I’m up to…

I am so freaking annoyed right now that I just have to vent for a second. There’s this guy who’s always at the gym every single time I’m able to drag my ass there for a 5 a.m. workout. I would admire his dedication and maybe give him some points for at least being cute if it weren’t for the fact that he totally disregards the “no cell phone” policy on top of being a disgusting “grunter.” 

I want to scream, “Listen, asshole: anyone who’s here at the gym at 5 a.m. is here because we also have busy lives and important jobs and no other time to be here. But yet we can somehow survive without a phone for less than an hour — get over yourself.”

And beyond him using his phone, it’s what he’s talking about. It’s not like he’s an ER doctor on call and people’s lives are at stake if he doesn’t weigh in with critical advice or something. Instead, he’s pretty loudly discussing deal terms and company details that seem like they should be confidential. Does he think he’s impressing someone with that British accent? It’s not charming at 5 in the freaking morning. To make matters more interesting, I figured out which bank he’s with and which startup he’s repping for their Series A funding. If I were an evil person, I could retaliate when he brings them in for their pitch.

So I move to a totally separate floor from him and am doing free weights … and here he comes again. This time his phone is off, but this guy still can’t be quiet. Every single machine he uses or weight he lifts involves some sort of primal scream or gross-sounding grunt and I just cannot deal with it anymore. But dammit I really like this gym. And there is no other time for me to get here. I need to think of another strategy to avoid him, because I’m certainly not giving up my workouts because of this fool.

I need to document the ridiculousness of what just happened. Then I’m giving up on this day and going to sleep. 

First, let’s rewind to this morning and afternoon, where I sat through lame pitch (Spotify for pets — huh?) after lame pitch (Fitbit for toddlers — why?) after lame pitch (a life-coach chatbot — no thanks!) and could literally feel my brain cells dying. In the evening I had to make an appearance at a goodbye party/happy hour across town, where I planned to stay an hour max, but then couldn’t end up finding a way to make a graceful exit for three hours because I kept getting pulled into different conversations. Three precious hours of my life I will never get back.

By the time I finally got home, I was exhausted mentally and physically and wanted nothing more than to wind down with my favorite ritual: a Korean snail mask (I’m a K-beauty freak), a glass of wine and an episode of the new season of Queer Eye. Because no one can make me forget my troubles like the fabulous Jonathan Van Ness.

So my gloriously slimy mask was on, the wine was poured, and I had just hit play when my phone started buzzing. And my friends, there was nothing good on the other end of the line. Nothing good at all.

Turns out the founder of one of our portfolio companies had landed himself in jail … in Vegas. Seriously, dude? How much of a fuck-up do you have to be to end up behind bars there? And why in the holy hell are you calling me to bail your ass out?

I had no idea what to do, and there was no way I was going to put myself in the position of keeping secrets for this guy. He was freaking out not only for the obvious reasons, but also because he didn’t know if he’d be able to have access to a phone again any time soon and was adamant that I not hang up on him. So I had to peel the mask off my face 10 minutes early, shut off the TV, put down my wine and attempt to conference call in another guy from XL who I had a hunch had dealt with (or been directly involved in) this level of debauchery before.

I’ll spare you the details of our plan to cover this mess up, but I will say that the founder’s phone access did indeed get cut off while we were talking to him, and then I had to stay on the line with my colleague for another hour figuring out logistics … and whether or not we were going to tell anyone else. (We did. We told Brock and let him take over.)

As I end this post I’m staring at my crumpled up snail mask on the floor but am too tired to even be upset. At least I learned I need to add one critical step into my wind-down routine: before I open the mask, open the wine or turn on the TV, I need to turn OFF my phone.