Clearing the (mental) clutter

When I read Marie Kondo’s book Tidying Up a few years ago, I promptly purged the overwhelming majority of my clothes (some from high school), knick-knacks, expired makeup, mismatched glassware, paper, and other junk that I had collected and stuffed in drawers and closets over the years. To my surprise, I’ve been able to maintain the system by seasonally going through clothes and systematically discarding stuff that I formerly would have held onto for years. I’ve been more conscious of what I let into my house  – I’ll turn down swag at conferences or ditch it in the hotel room; I donate or share books after reading them; I’m more discerning in the fitting room.

Even amidst a rough 2018 of homeowner problems, my house looked pretty tidy, but my mind still felt cluttered. Throughout much of the last year, I felt scattered, exhausted, and just generally unwell. For years, I had neglected the Health category on my Life Olympics and I was feeling it. I committed to finally making my mental and physical health a priority for 2019… and that was going to require setting some boundaries.

One month into 2019 it is not an exaggeration to say that I feel like a different person. I feel clear-headed, healthy, and full of energy. Perhaps most importantly, I have indeed reignited a feeling of deep joy after removing some mental and emotional clutter. Here are some things I put in place this month to declutter my mind and body:

  • A bedtime routine: Far too often last year, I found myself compiling spreadsheets and compulsively sending emails until the minute I went to bed. Shocking, then, that I wasn’t sleeping well. Technically, I was in bed for 7-8 hours a night, but I was maybe getting 3-4 hours of actual sleep. I woke up feeling groggy and lethargic every morning. I implemented the following routine and I stuck to it for all but 2-3 nights for the month of January when I made exceptions to stay out with friends:
    • 9:00-9:30 – wind down work-mode. I finalized emails and messages; brain-dumped to-do lists, and settled my work devices into their charging stations for the night.
    • 9:30-10 – 30 minutes of yoga. I started the Commit30 planner this year and my January goal was at least 30 minutes of yoga every day. Even with a month of nearly 20 days of travel (my usual excuse for slacking on exercise), I got it in all but two days, which I made up with doubles. I can’t overstate what this does for my mental and physical health.
    • 10-10:15 – get ready for bed and do my new skincare regimen because I see those lines creeping on my face and I am not ready to age gracefully.
    • 10:15-10:45 – light some candles and read for 30 minutes.
    • 10:45-11 – listen to the Daily Calm meditation while I fall asleep.

I actually started waking up before my alarm and not feeling like I’ve been hit by a truck all the time! I also have energy to spare for fun activities on evenings and weekends.

  • Taking control of my calendar: An undeniably important part of my job is taking meetings – with current and potential customers, partners, employees, and investors. It’s a LOT of meetings. And for years I have felt like I should make myself available to all of these people, anytime, anywhere. This often resulted in a calendar that consistently looked like a game-over screen of Tetris. I had meetings all day with 30-45 minutes between them, leaving me no time for deep-focus work (cue late night spreadsheets and such). I sat down and blocked out an ideal weekly calendar with strategic periods of time for 30- or 60-minute meetings and 2-3-hour chunks for focused work. I created appointment slots using Calendly and now use that to schedule meetings. I have occasionally made exceptions for conference schedules and such, but overall my schedule feels more manageable. In addition to carving out more time for strategic work, I also feel more clear-headed and attentive for each meeting that I do schedule.

None of these things is particularly drastic but the cumulative effect has been amazing. So why have these minor schedule improvements felt so impossibly out of reach for me for years? My big transformational life changes involve taking two hours a day of personal time and setting some modest parameters on scheduling?

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But it was, in fact, really hard to make these adjustments. At times, it was nauseatingly difficult for me to say no. I take a lot of pride in being available to my team and partners. There is also a lot of social pressure for entrepreneurs to appear indefatigable and I’m not immune to it. The media hype around the “hustle and grind” image makes it easy to feel like needing time to relax and unwind is a weakness – and there is even more pressure for female CEOs to feel like they can keep up.

I realized that my unwillingness to draw boundaries was rooted in fear. It sounds silly, but when I reflected on it, I realized that saying no/turning off prompted feelings of fear that people would think I was lazy or ungrateful or maybe not worth their time anyway. I am a big believer in the notion that speaking your fears takes away their power. Do I really think this partner won’t ever work with me if I tell them I can’t meet tomorrow? Do I really think a teammate will feel demoralized if I tell them I can’t meet until Thursday? Do I really think people will deem me lazy if I respond at 9am instead of 9pm? Probably not! I’m not totally cured of this insecurity/anxiety. I still feel it, but I’m working on recognizing it for what it is and literally asking myself these questions.

I’m only a month into the year, so I’m not yet ready to award myself the Gold in the 2019 Life Olympics, but this is honestly the longest streak of healthy behavior that I’ve been able to maintain since starting the company, so I’m taking a moment to celebrate. Cheers!



The #family channel

About 4 years ago, when an Allovue team member was expecting his first child, we created a #family channel in Slack as a repository for baby pictures while he was on paternity leave. As our team has grown and evolved over the years, the #family channel has remained one of my favorite bastions of our corporate culture.

Importantly, the #family channel leaves “family” open to interpretation. Diversity and inclusion are celebrated company values, so everyone’s definition of family is a little different.

In the #family channel, we share the joys of life milestones big and small: graduations, weddings, babies, haircuts, piano lessons, first days of school, vacations, meltdowns at the dinner table, science projects, new homes, workouts, renovation projections, pet snuggles, and all of the silly just-because moments that make us feel grateful and loved every day.

Because life happens, the #family channel isn’t all happy moments. We also share moments of grief: a death in the family, a relative in the hospital, a friend diagnosed with a terrible illness. While I welcome the daily dose of cute children and animals, the more somber updates have convinced me how critical the #family channel is to our work.

I’m not sure anyone has ever successfully siloed their “work life” and “home life”; it’s all just life. And frankly, why should we want to? To pretend that these categories exist in an emotional vacuum is to ignore the basic humanity of our coworkers and deny our team the opportunity to connect and empathize on a higher level. Our company culture is richer and our work is more fulfilling because we get to know our colleagues not just through their professional skills and contributions, but also who they are as parents, spouses, friends, siblings, caretakers, and fur-parents. We grow to understand each other as whole people.

The #family channel makes us better colleagues and managers. We subscribe to Kim Scott’s philosophy of Radical Candor – a management approach that exists at the intersection of caring personally and challenging directly. It’s naïve or delusional to dismiss the impact of personal matters (good or bad) on someone’s productivity at work. As managers, we must care about who people are outside of work and understand the circumstances of their lives in order to support and grow our team members to their full potential.

If your team doesn’t already have the equivalent of a #family channel, I encourage you to start one. Come for the cute pictures, stay for the meaningful connections.

In support of the Maryland Angel Investor Tax Credit Program


Last year, the Greater Baltimore Committee worked with Delegate Brooke Lierman and Senator Catherine Pugh on a bill that would have created an Angel Investor Tax Credit. The credit would function similarly to the very popular Biotechnology Investment Tax Credit but would be available to a much wider range of industries and companies. Despite two very good hearings, they did not get a vote on the bill last year.

Delegate Lierman has reintroduced the bill this year (Senator Pugh will be reintroducing, as well). Although I was unable to attend the hearing in person, I sent a written testimony in support of the bill, which is reproduced below.

Angel Investor Tax Credit Program
FEBRUARY 16, 2016

My name is Jessica Gartner and I am the CEO and Founder of Allovue, an education finance technology startup based in Baltimore City. I moved to Baltimore in the summer of 2009 as a Teach for America Corps Member. I taught middle school humanities in Baltimore City and completed my Master’s degree at the Johns Hopkins School of Education. In 2011, inspired by the energy and potential of Baltimore, I bought a house in the Hollins Market neighborhood, thanks to homebuyer grants from the Live Baltimore program.

In February of 2013, I quit my job to start Allovue. I was haunted by the inefficiencies of school financial management, as I had observed first-hand the direct impact that resource allocation has on teaching and learning. I believed that innovation in education finance technology could drastically improve access to timely financial data and help education leaders make better resource allocation decisions by connecting spending to student achievement data.

By all accounts, this was a completely insane idea. I had no previous experience in business, technology, or finance, but I was intensely driven by a vision for an education system that allocated dollars effectively to meet the needs of our students. I believed that I could rally a team of brilliant software engineers, data scientists, education finance experts, and designers to build a product that met the uniquely complex needs of education leaders everywhere.

Three years ago, I was a 26-year-old girl with a bold idea, a few PowerPoint slides, and an incredible passion for improving educational outcomes. The Emerging Technology Center in Baltimore took a big bet on me. I was accepted to the Accelerate Baltimore cohort in 2013, which provided our first investment of $25,000 from the Abell Foundation.

During the next two years, I raised two rounds of seed capital for a total of $1.8 million. 42 percent of that seed capital came from Baltimore angel investors. I used this capital to hire our founding team and build a product that was ready to go to market in school districts across the country. In December [2015], we raised an additional $5.1 million in Series A funding, led by Rethink Education, which will catapult our growth to a new level in 2016.

Today, I hired our 22nd employee, representing nearly 300% team growth over the past 90 days. Of those 22 people, we are in the process of relocating 7 of them to new homes in Baltimore City. We have just begun offering Live Baltimore matching grants up to $5000 to all employees who choose to buy homes in Baltimore. I sincerely hope they all take advantage of this.

Our sales are up 1000% since this time last year. In 2016, we are projecting 4000% growth over 2015 revenues. We are now working with school districts and state departments in 10 states across the country, helping education leaders manage and analyze over $3 billion in funding. And we’re just getting started.

None of this would have been possible without the early capital from angel investors. Angels make the riskiest investments in innovation – they bet on crazy, unproven ideas from inexperienced and unlikely founders, yet this is origin story of nearly every major technological breakthrough in America. Let’s make sure that more of them come from Maryland.

We should offer every incentive for betting on innovation and economic growth that starts and stays in Maryland. I hope you will vote to support the Angel Tax Credit, ensuring that all Maryland entrepreneurs with crazy ideas will have the best opportunities to access the capital necessary to build the next big thing.

For these reasons, I urge you to support House Bill 471.

Magically Redefine Your Team Roles and Responsibilities


Last quarter, a few things happened at once with our team at Allovue. 1) We were at a major inflection point, shifting my focus as CEO from mostly on product development to mostly on sales & marketing 2) Our CTO’s wife was 7 months pregnant, so we wanted to free up some of his time to spend at home once the baby arrived 3) One of our senior developers expressed interest in more autonomy and more responsibility. Here’s how we redefined our roles & responsibilities in a process that we completely pulled out of thin air and resulted in everyone on our leadership team being happier and more productive in their jobs. I’m telling you: magic.

I gathered the leadership team into the conference room and started by writing our names on the whiteboard. One at a time, we went around the room and each person named every process or category over which he or she currently felt ownership and responsibility.

After everyone listed responsibilities, we made a list called “No Man’s Land” for processes that we felt someone needed to own, but no one had named. (Note: We also put things on this list that people forgot to name earlier, because we figured this was an indicator of a responsibility that was not high priority or top of mind.)

This next step is the most critical ingredient of the magic. DO NOT SKIP THIS STEP. I went around to each person again and asked them to tell me “Yes” for things on their list that they felt were the right fit for them, and “No” for anything on their list that they wished for any reason was NOT on their list – you don’t like it, you don’t think you’re good at it, you think it’s stupid… whatever. “Yes” items got a check and “No” items got an X and were moved to No Man’s Land.

At this point in the process, everyone had a list of responsibilities that they loved and felt were appropriate for them to own. Now we had to contend with No Man’s Land: all the things we felt were important for somebody to own, but either no one did, or the person who owned it until now didn’t want to own it.

For the final step of this process, we went through each item on the list and decided to either 1) assign it to someone else on the team 2) find a way to make it suck less for the person who crossed it off their list 3) hire someone to do it.

And that’s when the magic happened.

As we went through the list, my team’s secret interests, skills, and talents emerged as, one by one, people volunteered to snap up items from No Man’s Land and take ownership of them. Rosalyn admitted to secretly enjoying close-reading of legal contracts, whereas I hated it and had been slogging through them. Jason volunteered to take on Sprint Planning, a process that was a total drain for Ted, but a natural fit for Jason. Jake took ownership of all front-end and design processes, which had been awkwardly and inefficiently split between me and the dev team. Ted reclaimed some technical processes, once we realized that a week of time could set up playbooks to automate all the stuff that was wasting his time.

At the end of this exercise, there were only four items in No Man’s Land, and they exactly mirrored the job description I had just written up for our new Venture for America hire. MAGIC. We went around once more to confirm that everyone felt comfortable with their new roles. Ted said, “Wait – that list is my job now?” “Yes…” I said hesitantly. A huge grin spread across his face. It’s a really good day when your CTO is happy.

This entire process took 45 minutes.

A few months in, here are some things that have resulted:

  • Our dev team velocity is higher than it has ever been. I attribute this to a combination of the fact that Jason enjoys Sprint Planning, and Ted has more time freed up to write code.
  • We have fewer errors in legal documents, because Rosalyn is a true Eagle Eyes and catches every. single. thing.
  • Rosalyn has also taken major ownership over customer on-boarding and project planning, demonstrating her unique strengths as a leader in this area
  • Jake has streamlined design processes, which has further contributed to increased velocity
  • My time has been freed up to focus on sales and marketing

Here are some of my key takeaways from this exercise:

  • Don’t let corporate dogma dictate the roles and responsibilities of your team.
  • Making people do something because “they’re supposed to” will drain your employees and slow down your team’s velocity. Sure, everybody has to do some things once in awhile that they don’t love… but make sure it’s really “once in awhile” and not “most of the time.”
  • Take a strengths-based approach. Hopefully, you hired people who are uniquely qualified to contribute to your team. Play to their strengths. They will thrive, and the whole team and company will thrive right along with them.
  • Listen when people ask for more responsibility. Don’t let talent and leadership sit dormant in the organization. This doesn’t mean promoting everyone to an executive position, but find ways to give people opportunities for leadership when they crave it. This might mean giving someone a leadership role over a single project or feature in the short term, and it might unleash new skills and talents you never saw before.
  • Just because someone “can” doesn’t mean they “should.” Founding team members tend to be multi-skilled individuals. It’s easy to assume that because someone is capable of doing something, it makes sense for them to keep doing it. Take inventory of these things regularly – can someone else on the team do it faster, with more joy? This goes back to the strengths-based approach: are people spending their time in the most efficient way, given the skills and talents of the team as a whole? Make sure that people who are uniquely qualified at high-value, mission-critical tasks are spending as much time as possible on those tasks.

I expect that we will return to this process as we grow, consistently reevaluating how team members are spending their time, and ensuring that we’re leveraging leadership capacity across the organization – because a happy, healthy, productive team is nothing short of magic.

If you try this magic process, or have done something similar, I’d love to hear about it!

Everything I know about being a CEO, I learned being a teacher


“How can you be a CEO when you were just a teacher?”

This is one of the most common questions I have fielded as the CEO and founder of Allovue, an early-stage financial analytics company. Initially the question offended me; I prickled at the insinuation of all the worst teacher stereotypes: teachers aren’t as smart or shrewd as other professionals, teachers are lazy, teachers are fluffy.

Now, I’m amused by the question. After all, teachers are the unsung CEOs of the world. Teachers manage hundreds of people every day (who are not paid to show up!) Teachers prepare and present 4–6 hours of unique content every day, and are evaluated based on those hundreds of students’ ability to process and retain this new content. Teachers make all their own agendas, PowerPoints, and reading materials. They often buy their own presentation tools and office supplies — for over a hundred people. Sorry, no T&E reimbursements! They make their own photocopies of materials they created or purchased themselves. They give individualized feedback to over a hundred people on a regular basis. Hey, CEOs — when was the last time you reviewed and evaluated the daily work of +100 employees after doing all your own work and meetings for the day? And don’t forget to call all of your employees’ parents at least once a week to let them know how they’re doing at work! Great teachers are virtually superhuman masters of management and logistics.

I’ve come to realize that most of my favorite management strategies were fire-tested in the classroom, not a boardroom. Having taught students from kindergarten age up to the graduate level, I’ll let you in a little secret: managing adults is not all that different from managing children.

Public praise, private punishment

This is a staple of classroom management. Can you remember a time that you were called out in front of your peers for doing or saying something wrong? Can you feel your cheeks getting warm just thinking about it? Now, think about a time that someone praised you for a job well-done in front of all your colleagues. I bet your chest is still swelling with pride. This is a pretty basic tenet of human psychology: most people appreciate public recognition for good work, but feel humiliated by screwing up in front of their pals. Publicly chastising people for mistakes might create results in the short term, but it’s no way to build a strong culture in the long term.

As often as possible, we make an effort to let our team know about all the awesome things their teammates are doing — we also share a weekly newsletter with team shout-outs and appreciations, ranging from small helps (“Thanks for giving me a ride home”) to big wins (“Great job closing that sale! Coffee for everyone!”)

On the contrary, if something is going awry with process or performance, we address these issues privately with team members, and we focus on figuring out why something isn’t working and what steps need to be taken to fix the problem. It is difficult to consistently do this without egos and finger-pointing. We are not perfect at it, but couching these discussions in terms of finding solutions instead of allocating blame goes a long way.

Give credit, take blame

As a general rule, when something good happens, my team did it. When something goes wrong, it’s my fault. As the CEO, you have little to lose by accepting blame. It takes pressure off the team and frees up their mental space to focus on solving the problem. Are you sensing a theme here? People don’t function well when they’re embarrassed or scared.

As for giving credit, let’s harken back to Obama’s “you didn’t build that” decree. No matter how much of a 10x-programmer-visionary-wünderkind you are, it’s extremely unlikely that you built something great alone. Give credit where credit is due — and then some. Elevating others does not diminish you. Take every opportunity to credit your team, investors, advisors, and customers because this is an all-ships-rise-win-win situation.

Bring cupcakes

I don’t care if you are 5 or 50 — people love cupcakes. I have studied this extensively, and the effects of cupcakes on a classroom or office are the same: good cheer and a burst of productivity. We are lucky enough to have the gourmet cupcake shop La Cakerie down the street from our office and we are frequent patrons. Birthday? Cupcakes! Engagement? Cupcakes! Good press? Cupcakes! Thursday? Cupcakes! Celebrate each other. Celebrate wins, big or small. Celebrate just because you are all in this together, doing the hard things, fighting the good fight, and goddamit, you deserve a cupcake.

If You Can’t Do Anything Else

Every theatre kid has a moment (or many moments) when they consider pursuing a career in acting.

I had my moments. Every few months or so for the decade between middle school and college graduation (the heyday of my theatre career, as life would have it), I would threaten my parents with pursuing acting. I even declared a second major in Theatre second semester of freshman year (which I later demoted to a minor).

I remember the popular maxim that often accompanied these ambitions: “You should pursue a career in acting if you can’t do anything else.” It wasn’t until several years post-college that I learned there were actually two interpretations of this adage.

I had always interpreted the phrase to mean that you should pursue acting if you couldn’t breathe without it; if you felt as though you would truly perish from asphyxiation, choked by your own unfulfilled potential on the screens and stages of the world. (I was a little bit of a drama queen, and perhaps prone to hyperbole.)

Another friend interpreted it more literally: you should pursue your thespian ambitions if you simply have no other skills with which to barter in the game of Life. If that is your one talent, then you may as well play your hand. If you can do something – really, anything else – definitely do that instead.

I still like my version better. It has poetic conviction: give me the Backstage listings or give me death!

In any case, my theatrical ambitions didn’t pass muster by either definition – I loved (and still love) theatre, but felt I could be happy leaving it as a hobby. In fact, I feared the opposite: that I would rely too heavily on the art as a meal ticket, take parts I didn’t love in shows I didn’t believe it, and slowly start to resent it altogether, the way people spoke of being sickened at the sight of ice cream after a summer scooping sticky globs of the stuff. And supposedly, after four years of a good college education, I had other marketable skills to lean on. (Time will tell, I guess.)

I spoke to a young(er) entrepreneur-in-waiting last week, and he told me he had a list of about a dozen business ideas he was thinking about pursuing. Without seeing the list, I told him none of them was the right one. He asked how I knew, and I said that when he found the right problem to solve, he would unquestionably know it to be the one to pursue. He wouldn’t be able to do anything else.

Two years ago, that is how I felt about a problem that I later started Allovue to solve. I couldn’t sleep. I couldn’t stop thinking about it. I felt certain of my impending death, crushed by the weight of regret (there’s that hyperbole again!) It’s a feeling not so unlike lovesickness. I couldn’t do anything else.

I think founding a business is a pursuit worthy of hyperbole. There’s plenty of rejection, the odds are not ever in your favor – it’s really not so different from a career in acting, when you think about it. For every break-out celebrity, there are thousands of people getting typed-out all day. For every Uber, there are thousands of wantrepreneurs honing their “Uber for X” pitches. Unless you’re Richard Branson or Elon Musk, you probably can’t just pick an idea off a list.

You should only pursue your business idea if you can’t do anything else.