Saturday, August 2, 2014

The Last 5 Years in Baltimore

I never believed I was in Baltimore by accident. I woke up one morning in my senior year of college with the sort of impulsive conviction to move here that can only be attributed to fate. When I met a guy a matter of weeks after moving here, I was sure he was the reason I was here. When it fell apart the following year, I questioned all of my instincts and shook my fists at the fates and desperately wanted to run very far away and never look back.

And yet, here I am.

In the winter of 2011 I had been living here discontentedly for a year and a half and gave myself 6 months to find my people or pick up and go. Of all places, I started to find my people on Twitter in the technology community. I have to credit Kate Bladow for being a connector extraordinaire. It was on Twitter that I learned about Create Baltimore, and having declared to Crystal that I was going to Do Things and Go Places and Meet People, I went. Something clicked that day - I found a community of people that inspired me. I decided to stay. Relying on instinct again, I put an offer on a house the very next week.

I found myself in a dark place a year later, feeling completely at odds with my career, which was essentially my whole adult identity. We'll call this a quarter life crisis. I made a sharp turn into the world of venture capital, which didn't quite fit me, either. There were a lot of restless nights in the fall of 2012 as I wrestled with the spark of an idea that would not leave me alone. I saw it, but I didn't know how to build it. I didn't even know where to start. It was an utterly absurd, terrifying notion. I considered the worst case scenario and imagined abject failure, humiliation, bankruptcy. In this case, I supposed I would book a one way ticket someplace far away and open a waffle stand on the beach. That sounded pretty ok, actually. For a third time, I trusted my instincts.

And so, here I am.

Since I'm a big nerd, here's a little infographic of some Life Olympics highlights from my last 5 years in Baltimore.

Cheers, hon.


Thursday, April 10, 2014

Remembering Michael

In the pre-Facebook days, Penn had a separate online portal for newly admitted students to gossip about dorms and classes and clubs, and other pre-college chatter. Michael and I were both admitted early decision and we quickly progressed our friendship from Penn portal to AIM to the regular old telephone. We were 17 and it seemed impossible to wait 9 months to become in-real-life friends, so we decided to rendezvous at his house, just about 45 minutes north of mine. I met his lovely parents and then we made our way to the Wendy's drive-thru and took our cheeseburgers to a nearby park to listen to all our favorite music. Ok, Michael's favorite music, which became my favorite, too. It was the most ordinary thing for a bunch of high schoolers to do, but it was a memory made extraordinary by virtue of being with Michael.

Photo by Raymond Colon
I was shocked when Michael told me before winter break freshman year that he wouldn't be returning to Penn in the spring: he was joining the Navy. I balked at the idea. You? The Navy? The same guy who fiercely debates the merits of the Oxford comma at 4am? Michael made the case that he didn't really know what he wanted to do, and couldn't see the sense in spending all that tuition money figuring it out. Well. That may sound like a well-reasoned response, but Michael had gone to the same kind of parochial high school as I had, so we both knew he was supposed to graduate from an ivy league school with honors and settle into something suitably professional. He was deviating from The Plan. 8 years later, I found myself in the same situation, and I found myself channeling Michael's courage to carve out a different path. He was one of the first people besides my parents that I told about leaving my job to start the company, because Michael had a way of making you feel like you were destined to make all the big decisions you were making, and he'd just been patiently waiting for you to figure them out.


For the 7 years that Michael served in the Navy, he was mostly based in far-away places. Somehow, we knew our friendship was special, and diligently kept in touch with letters, emails, phone calls, Facebook, and a visit whenever he was on the east coast. He came to speak to my class during my first year teaching in Baltimore, which I think was an enlightening experience for all parties involved.

Getting older and moving around makes staying in touch with old friends harder. There's an illusion of intimacy since we're all constantly aware of each other on Facebook. It's easy enough to say, "We should totally get together the next time I'm in your city!" But Michael really meant it. If we were within 200 miles of each other, we would find a way to see each other.

We said we loved each other a lot. As a society, I think we're bashful about loving too much. We get wrapped up in the implications and insinuations and we treat each other so casually. Michael did nothing casually and we were unabashed in our mutual expressions of love and affection. Imagine if we were all so unapologetic about loving our friends? Just big, bold, audacious love. If anyone is afraid that too much love would make it any less special or intimate, trust me that Michael's whole existence was evidence to the contrary.


A strong theme has emerged in the dedications to Michael over the past few days: It didn't matter if he knew you for 10 minutes or 10 years, he made you feel special. Michael had some sort of super power in that he could immediately pinpoint all of your insecurities, gently make you face them, and just dissolve them, leaving only the beautiful parts. This gift for seeing the beauty in every person he met made him a remarkable photography, and a truly extraordinary human.


“You know when you've found it, that's something I've learned, cause you feel it when they take it away.”

Love you, Michael.
 







Monday, March 10, 2014

Don't Ban Bossy, Rebrand It

As someone who has been called aggressive, overbearing, loud, bitchy, smartypants, smart ass, intimidating, and, yes, bossy, since age 2, I do not approve the Ban Bossy campaign. I earned that title and I own it.


Being bossy is about as fundamental to my sense of self as being female, and I am not relinquishing the trait. I was on board with Lean In - that was a calling to step up, to take ownership, to stake claim. But banning bossy is about taking away - and that rarely ends well. Instead, let's reclaim it.

I have been bossy since the day I learned to talk. Being bossy has helped me to become captain, editor, president, teacher, director, CEO and founder of the various activities of my life. I was so bossy when I was a kid that my aunt wrote a book series called Smartypants that was loosely based on my antics. As recently as last year, I earned an award for my Bossiness (fittingly, the Tony Danza Who's the Boss and Tina Fey Bossypants award), courtesy of the Emerging Technology Center Accelerate Baltimore. I know bossy. I am bossy. And I own bossy.

I was bossy in the classroom, on the playground, on and off stage, at home, on the soccer field, on the pitching mound, and now, in my office. I suspect I will continue to be bossy until I take my last dying breath, with zero apologies.

Bossy is not the problem. Bossy has a branding problem.

Yes, women are called bossy more than men are. Men are also called assholes, jerks, and dicks more than women are. Yet, in the business world, being an asshole has a culture of idolatry around it, because that's how it's marketed these days. If you're a male CEO, being an asshole is a pretty high order compliment, because you know who else are framed as assholes? Steve Jobs and Jeff Bezos. I have great disdain for this particular reframing, because I don't think the world needs any more dickhead bosses running around with a god complex, but it's a great example of reclaiming a word.

So rather than banning bossy (which is bound to backfire, because nothing invites ridicule like prohibition), let's reframe it, reclaim it, rebrand it, and run with it.

Bossy steps up.
Bossy knocks it out of the park.
Bossy knows what she wants.
Bossy asks the right questions.
Bossy owns it.
Bossy runs the show.
Bossy gets shit done.
Bossy is efficient.
Bossy takes the lead.
Bossy doesn't whine.
Bossy makes no excuses.
Bossy takes risks.
Bossy doesn't take no for an answer.
Bossy finds a way.
Bossy wins the day.

Who's bossy, now?

Monday, December 30, 2013

The Year in Review

2013. I don't want to tempt (or limit) the fates by awarding this year any premature superlatives, but I have a suspicion that I will always look back on 2013 as a pivotal year in my life.

It's a little surreal to think that so much of what brings me daily joy and fulfillment didn't even exist a year ago.

For the past few years, I have come think of adulthood as the Life Olympics: the constant striving for balance between Career, Home, Relationships, Health, and Wellness.

The results are in for 2013:


Career - Gold Star
Founding and growing Allovue has been a thrilling and fulfilling journey, and I can't wait to see what next year brings. Despite the popular myths about startup founders failing to sleep, eat, or do anything unrelated to business orders, I think I succeeded in striking a pretty fair balance with the other 4 realms of my life, but there's still plenty of room for improvement.

I resigned from my job the first day back after the New Year holiday. I had come across this quote on Pinterest from We Bought a Zoo, and just kept repeating it to myself:


20 seconds of insane courage. Emphasis on insane. I had no plan, no funding, and no experience - just some gnawing intuition that I had to go bring this idea in my head to life, or feel the churning discontent of regret forever. So, into the abyss. 

I woke up on Monday February 4 - my first day as an untethered, fun-employed entrepreneur - feeling an odd mix of liberation and terror. For the first time in my adult life, (maybe my entire life?) I felt solely responsible for myself. There was no one to tell me what to do or how to do, but then, there was no one to tell me what to do or how to do it. I was a bit paralyzed by the weight of my newfound freedom at first, and then at 9:49am, I remembered: "To begin, begin," and so I began. I'm not sure what I did that first day, but I must have felt some vague sense of accomplishment, because I had this to say at the end of the day: 
I know it won't always be this fun...But isn't it ok to bask in the sheer exuberance of it - just for a little while? Just for today, I'll relish in the joy that accompanies the audacity to live the very life I imagined. Just for a moment, I'll play in that narrow intersection of pleasure and purpose, feeling infinite and electric.
Fortunately, that feeling lasted more than a day. The chaos of "startup life" feels oddly natural to me in a way that the routine of other jobs never had before. I think I worked on 8 different jobs this year to make it work, but I did it on my own terms, so I can finally read this speech without the nagging feeling of being slightly off center:
The only way to do great work is to love what you do. If you haven't found it yet, keep looking. Don't settle. As with all matters of the heart, you'll know when you find it. 
- Steve Jobs
Relationships - Gold Star
Speaking of matters of the heart, two weeks before I started Allovue, I decided I was tired of eating dinner alone and revamped my online dating profile for what I promised would be the last damn time. I agreed to exactly one date the day after I activated my profile. On the way there, I reminded myself (aloud) that I was officially done compromising on my non-negotiables in relationships. Maybe the universe just wanted to hear me say it out loud, because I went into Brewer's Art that night to meet the actual man of my dreams in real life. I don't know if there's ever a good time to start a new relationship, but I'm pretty sure it is not two weeks before you leave your job to start a company. I've heard it said that you find love when you find yourself - I just wasn't expecting it all to happen, like, immediately, all at once, very fast.

Home - Silver
In the Home category, I include basic home maintenance, cleaning, and keeping personal finances in order. My home was probably cleaner than usual this year, because I was constantly hosting new AirBNB guests. Talk about an incentive to keep the house in order when people are literally rating your house on its cleanliness! Of course, part of my strategy was to just relegate the mess to my room, but even that's had to change with the addition of our new kitty, Darwin, who likes to scratch, sniff, claw, and eat anything in reach. I'm running out of room to stash junk and mess, so it looks like I will finally have to be a grown-up and either purge excess or keep things tidy! #likeanadult


Health - Bronze
As it turned out, it was a good year to start dating a doctor/lawyer. At the end of January, I found myself engaged in a class-action lawsuit after it was discovered that my doctor had been allegedly secretly photographing patients with a camera pen and subsequently committed suicide. Feeling anxious about the care I had been receiving for the past 4 years, I quickly sought a new doctor and was diagnosed with endocervical adenocarcinoma in situ - stage 0 of a fairly rare form of glandular cervical cancer. My doctor said it was usually difficult to catch this type of cancer so early, but since we did, I was able to have a minor surgery to remove the cancerous cells. I just had my 6 month check-up, and my tests came back normal!

So this whole litigation/investigation process turned out to be a bizarre, potentially life-saving blessing. Unchecked, the cancer would have very likely progressed and I would have been facing far more invasive treatment options. This made me think about all of the men and women who put off visiting a doctor for routine check-ups because they lack basic insurance. If my father hadn't harangued me about securing private insurance before I left my job-with-benefits, a health crisis would have been a financial catastrophe, too. Even my small surgery would have cost over $10,000 without insurance. This whole ordeal gave me a deeply personal lens with which to view the Affordable Care Act debate this year. I'm thankful our country is finally making an attempt to fix what I can attest to be a very broken system.

Despite attending more Bikram yoga classes this year than either of the past 2 years I've been practicing, I still didn't get to as many as I had aimed for. This is an area of my life that I really to need to work on making it a permanent habit. It's (sadly) looking like the best way to do that is to just get up at 5:30am to make the 6am class. I've gotten better at it, but it's still going to take some practice to make it less of a struggle-fest in the morning.

Wellness - Honorable Mention
No surprises here. Personal wellness falls to the bottom of my priority list, year after year. I define personal wellness to include the things that feed my brain, creativity, and soul - probably not where I should be slacking off. This realm looks different for everyone, but for me it includes reading, writing, singing, cooking, taking pictures, and going to yoga. I fell woefully short of my book-a-week reading goal this year and abandoned my photo-a-week project in February. I did maintain my singing lessons every other week, which is a small victory, and I've started to carve out time for cooking delicious things on Sunday afternoons. This area definitely needs more work in 2014, and I think it needs to start with a shift in value judgment. In my gut, I know most of the inspiration for my "real" work comes from this personal creative time, but it's so indirect and quiet that it's easy to write-off these activities as less essential. No more! Wellness is essential.

You'll Figure It Out.
In 2012 I wrote a lot about gender politics in the tech world. One day, I stopped and took a hard look at my own life. Technology, specifically as it related to solutions for education, was clearly a big passion of mine. Why wasn't I doing work in that field? Why wasn't I taking a leadership role in the very area that I was lamenting a lack of female leadership? The answers were all rooted in blinding fear. I was afraid I wasn't appropriately "certified" to do what I wanted to do. I was afraid I didn't know how to do what I wanted to do. I was afraid of what people would think, or say. Then, I realized that none of these were particularly good reasons to not do a thing that I wanted to do. So, I decided to just muster up that 20 seconds of courage, and force myself to figure it out. I surrounded myself with smart, helpful people, and asked a LOT of questions along the way. "Leap and the net will appear," says an old Zen proverb. Sometimes, you just have to build your own net.





Monday, November 4, 2013

Scenes from an Indian Restaurant

SETTING: An Indian restaurant in California.

JESS sits down and scans the menu, which is unusually lengthy - a booklet of perhaps 15 pages.

MAN: You eat Indian food a lot? You know a lot about it?

JESS: I... eat it pretty frequently.


MAN: We don't really eat like that in India, you know. I mean, who could possibly eat like that every day? That would be ridiculous. It's much too rich. It's not real Indian food.

JESS: I think that's probably true of most ethnic food restaurants...

JESS, now self-conscious about what she is ordering, goes to the other side of the restaurant to submit her order. Upon return:

MAN: Do you work for Cisco?

JESS: No. My father and brother do, though.

MAN: What department?


JESS: My father works in the optics division and--

MAN: Oh, I don't know about that. Do you work in the software industry?

JESS: Yep. My company builds financial insight software for school districts. 

MAN: No... that's... public education is not very good. You should sell to private schools. There's no money in public education.

JESS: Well, about $600 billion is spent annually on K-12 public education - the private education market is only a small fraction of that.

MAN: Really? I guess you would know. So what do you do? Like marketing or something?

JESS: A little bit of everything, these days! I founded the company.

MAN: You can code?

JESS: I can, a bit. But I don't do development for the company. We have a great team of engineers, and I primarily drive the business development.

MAN: What made you do this? Just start a company?

JESS: Well, I used to be a teacher, and I thought there was a better way to think about resource allocation for public ed, so I started the company to build those solutions.

MAN: You just saw this problem... and started a company? You sound like a very aggressive woman.

JESS smiles politely.

MAN: Hm. Starting a company to solve a problem. Beat. You don't hear that very much. 

JESS nods.

MAN: A lot of people out here start companies. Beat. They have different motivations, though.

JESS: Like what?

MAN: Um... financial, mostly. 

Food arrives and JESS and MAN arise to leave.

MAN: Well, good luck. It sounds like it would be very difficult to do what you're doing. 

JESS: Thanks, enjoy your dinner. 

END SCENE.






Wednesday, October 16, 2013

Don't be a jerk... please

Every once in awhile I read something on the internet that affects me on such a visceral level that I feel the need to respond at length.
Source: http://xkcd.com/386/

Today, I came across this headline from Entrepreneur: "Why It Pays to Be a Jerk Like Jeff Bezos" by Gene Marks. He begins with a story of how his teenage sons routinely failed to comply with cleaning up their plates of food at night until one evening when he hurled the soiled flatware at their bedroom walls while screaming, "Clean up your f--ing mess and don't let this happen again!" He (proudly?) claimed victory on the matter. Father of the Year!

The rest of the post included anecdotes of Steve Jobs, Jeff Bezos, and the author (imagine?) acting like petulant jerks to employees and even clients (in the author's case). He pulls quotes from a recent book on Bezos and the evolution of Amazon:
"In the book, Bezos is quoted as saying things like "Why are you wasting my life?", "I'm sorry, did I take my stupid pills today?" and "This document was clearly written by the B team. Can someone get me the A team document? I don't want to waste my time with the B team document." Or my personal favorite response that Bezos gives when someone resists him: "Do I need to go down and get the certificate that says I'm CEO of the company to get you to stop challenging me on this?" Geez, what a jerk."
The prescribed takeaway for managerial excellence? "They have to be [jerks] in order to get what they want to grow their businesses. Maybe we should all be jerks sometime too."

Alright, disclaimer: I don't have an MBA and I never took MGMT101, but I'm pretty certain that treating your colleagues, customers, children (or anyone? ever?) like crap is not a recipe for growth and success. However, I did spend the past seven years studying education and teaching in various capacities, so I picked up a thing or two about behavior and cognition. 

If you want a crash course in motivation, spend a day in a middle school classroom: emotions are erratic, hormones are flying, and tempers are flaring.  Never, ever, ever would a teacher succeed in motivating students through insults, anger, or humiliation. Threats and power flexing may have some short term effect of shutting someone down or forcing someone into submission, but the long term effects of these dynamics are anything but successful.

The real tragedy of this post is that too many startup-legend-wannabes will take the author's loose (and irresponsible) correlation between the bad behavior anecdotes of Jobs and Bezos at face value as a characteristic of great leadership. I would argue that if these tales of rude behavior are consistently true of Jobs and Bezos, these individuals are the very rare exceptions to the rule; Jobs and Bezos are legendary business leaders in spite of their harsh/foul language, not because of it. I fear that too many CEOs in training will presume causality where there is none, and flaunt insults, tempers, and rudeness in hopes that they'll someday be preserved in biographic lore.

For those startup-legend-wannabes in need of an idol to emulate, I might suggest instead Tony Hsieh, CEO of Zappos, whose personal and company philosophy is "delivering happiness." Hsieh empowers employees at every level of the company and regularly (and publicly) celebrates their successes in customer service, product development, and leadership.

Lastly, I think it's worth mentioning that there is an inherent double standard for male and female bosses being hard-asses at work. Research and case studies show that female leadership and likability are inversely correlated. Female bosses acting outrageously to the degree of the above examples would serve to perpetuate the stereotype that women are "too emotional" or "crazy" to successfully lead organizations. While outlandishly bad behavior from female CEOs would very likely make headlines, I'm quite sure they wouldn't be dripping with praise or recommendations for imitation.

Marissa Mayer created a media firestorm when she requested that employees actually start coming into work, and she gave several months notice before the policy change. In Mayer's memo, she stated:
"To become the absolute best place to work, communication and collaboration will be important, so we need to be working side-by-side. That is why it is critical that we are all present in our offices. Some of the best decisions and insights come from hallway and cafeteria discussions, meeting new people, and impromptu team meetings. Speed and quality are often sacrificed when we work from home. We need to be one Yahoo!, and that starts with physically being together."
In response, one disgruntled employee said, "It’s outrageous and a morale killer.”

Months later, Mayer seems pleased with the state of Yahoo's company culture, as evidenced by the fact that employees have stopped leaking her emails to the press. According to the Gene Marks school of management, Mayer should have thrown in some insults, cursing, and other invectives to get what she wanted, but then she would probably be condemned as a crazy bitch whose hormones never regulated after popping out that baby. She wasn't a jerk, and she got the job done anyway.





Thursday, September 19, 2013

Edtech rant: Stop iterating, start innovating

I'm increasingly distressed by the quality and nature of the new crops of edtech companies. It's more of the same incrementally better (well, marginally different) stuff over and over and over again. How can the market be so painfully saturated with me-too products and yet still so completely desperate for solutions to Big Problems? This is a listening failure of entrepreneurs that borders on the level of disconnect usually reserved for government agencies.



Want to be an innovator? Then innovate. There are so many colossally inefficient administrative systems gumming up the works of the education sector. Just pick a problem - any problem (a real one) - and get to work! Short on ideas? Talk to customers, maybe. They have LOTS of problems for which you can go off and design brilliantly engineered solutions!

Take BIG leaps. Go crazy!

Here are just TWO free ideas I heard from one teacher last night:

1) Build a better coursework database so students, parents, counselors, and teachers can monitor who's on track to graduate (or not) before it's too late. Think those things don't have an impact on student achievement? Tell that to the senior girl in CALCULUS who's being told she needs to retake Algebra I this year because someone entered the wrong code in the course registrar, putting her in danger of not graduating unless she retakes the course.

2) Build a better application for school choice selection that highlights the relative strengths and weaknesses of schools, transportation options, and achievement records. This would prevent parents from sending a high needs special ed student to a school with a weak or non-existent special ed program, as a completely hypothetical example.

For the love of school supplies, BUILD STUFF THAT MATTERS.