Below is the copy of an email I sent my team on June 30, 2015:

On Friday afternoon, I sat down to be interviewed by a high school student interning at my company this summer.

She had prepared a number of thoughtful questions about the path that led me from the classroom to running a company, including this one: what's the best part, and the hardest part, about being CEO?

I explained that, for me, the answer was the same for both questions - what I enjoy most about my role is being in charge - setting the vision, charting the path towards that vision, inspiring others to join me on that path, deciding when and how to adjust course in highly ambiguous situations. And what is most difficult is the fact that no one is telling me what to do, advice is often conflicting, and there are many people relying on me to make decisions in situations where there is often no "right" answer. 

Yet, as I've been reflecting this weekend, there's more to it.

When you're the CEO, your words and actions carry more weight than the average person's. The feedback you give to employees, the questions you ask in meetings, the topics you choose to discuss - and those you gloss over - send a message about what matters within your company.

That weight has felt heavier than ever to carry in the past two weeks.

I woke up two Thursdays ago to the news of the shooting in Charleston, and started my work day by leading my company's Board meeting - without stopping to acknowledge the terrible news.

In the emails and meetings and Hangouts and Skype calls with colleagues since then, I've continued to skip over current events like the tragedy in Charleston, the history-making Supreme Court decision about marriage equality, terrorist attacks abroad, instead choosing to proceed like it's business as usual.

All the while, I'm beating myself up on the inside for not knowing what to say, for being afraid to say the "wrong" thing, for wondering what good it will do to invite dialogue about inequality and injustice in a work environment, for knowing that it will require us to own our struggle to build a truly diverse team and acknowledge that we're far from perfect.

For feeling like talking about prejudice and inequality isn't enough. And simultaneously feeling that, as a mission-driven company, we're already working to address injustice in our country's education system; what more can we do?

As Gabrielle Blair writes:

"There are deeply smart, endlessly eloquent people that have written, and continue to write, thousands of good, moving words on the subject of race in America, and specifically the brutal killings in Charleston. What can I possibly add to the conversation? Well, probably nothing. But that’s not the point. The point is to have the conversation. To talk about this. To not just read and click “like” and move on. But to actually talk about this, to discuss it, to communicate about it. To share an opinion, and to be open to having that opinion change if necessary. I can read something or follow a hashtag and shake my head in disbelief and shame, but if I don’t speak up and talk about this with everyone that falls within the sound of my voice, then I’m adding to the problem, not helping."

As hard as it is to admit, adding to the problem means that when I, the CEO, keep my mouth shut about current events, I'm sending a message to my team that these topics aren't important, that you shouldn't be talking about them at work, that we're too busy or have more important things to do. 

So here's what I want to say to my team: That's not true. We can't show up to work acting as if it's business as usual when it's not. We need to be able to acknowledge current events happening beyond our corporate walls, even if we don't know what to do about them. Because talking about it isn't enough, but that doesn't make it ok to ignore the conversation all together.

A couple weeks ago, Neerav Kingsland asked, "why aren't more people crowdfunding schools?" The argument was primarily financial in nature; using back-of-the-envelope math, he estimated that a family considering private school could save $150k over a child's lifetime by financing the startup costs of a public charter school.

It's been a busy September. Here are my belated thoughts -

Call me pessimistic, but I see ideas like this potentially widening the achievement gap, not closing it. I'll let Matt Candler take the "yes, and" approach. I'm feeling very "hey, wait a second" about this question.

For starters, it makes me think a LOT about whose money we're taking at the charter school whose board I sit on, the inevitable influence of those donors, and the power dynamics between those who give financially and those who give in other ways or not at all. I agree with Neerav's premise that we should be innovating with respect to the way schools are funded, but also need to be mindful of how direct/crowd funding can unlevel the playing field. 

A friend who runs a charter school mused, "What if we did a 100% anonymous crowdfunding (anonymous even to us at the school site)?  Might that be able to get at the ends that Neerav and Matt suggest while still side-stepping the implied consequences of money as influence?"

To which I replied, "Would seem to me that in order to make philanthropic contributions completely anonymous, you'd have to set up a separate 'holding' 501c3/fund, that takes in individual contributions, documents them for tax purposes, and then allocates the aggregate funding to the school in one lump sum. I really like the idea of making all contributions - from a parent's $10 donation to a Walton grant - anonymous, so that no one donor gets special privileges like information rights, etc. Except how realistic is this? Seems pretty idealistic. Would Walton ever agree? Worth thinking through further though."

This week, more than a few people have sent me a link to BusinessWeek's current cover story, the title of which attempts to claim that tech arrogance is a good thing.

Friends, can we please call this what it is? Complete and utter nonsense, if you're building a company that seeks to have a sustaining impact. It's also, as the BW article points out, a front - mostly surface-level showmanship and fear of vulnerability.

This was top of mind for me this morning, after my colleague and Head of our Professional Services team sent the following note to our team of Implementation Coaches and Coordinators:

Dear Team,

I was reflecting on my time spend in schools over the past week. It was a privilege to be invited to join the opening session of school at Washington High School yesterday. As I listened to the hopes that the visionary principal shared with her teachers, some their first day and one teacher who is in his last year before retiring, I was taken back to so many "first days of school" I have had in the past.

As a former administrator, I know how hard it is to make the decisions about how to spend this precious professional development time. I just want to thank all of our partners who are trusting us with this time. Enjoy it with your new friends - our clients - and make it a great day! I am humbled by this opportunity.

Within the entrepreneurial path, there is a culture of "faking it till you make it." You pump your company up and say "everything is up and to the right" whenever someone asks. Meanwhile, you're stressed out and wondering how to take the next step. There has recently been a growing acknowledgment of mental health issues being very much part of the entrepreneurship culture in part because, even in the world of startups, people are afraid to fail in an excruciatingly public manner.

Coming off a week of working out of 4.0 Schools as an Entrepreneur-in-Residence, I am struck by how much I have learned about operating a business over the past five years since leaving the classroom. 

Been reflecting on this and asking myself: 

Given all that a first-time founder with zero business background needs to learn in order to be successful, how might we condense all of this and explicitly front-load it in order to rapidly accelerate someone's development as a business person, instead of hoping they'll just figure it out because that's what we all had to do?

Here's a first stab at explicitly modeling and coaching one minor but important technique critical for success in early stage entrepreneurship: the art of the e-intro. I'm writing this from the perspective of the coach, not the entrepreneur, because I want to highlight how important it is not to assume first-time founders know how to maneuver through the implicit social norms of startup culture. 

Note my deliberate effort to follow up and "check for understanding" (yes, you can take the teacher out of the classroom but I'm still forever a teacher) - this is admittedly tough to do, because you run the risk of being patronizing or overbearing. Even writing this post feels a bit patronizing, but I ran it by the people who are a part of this story, and they assured me that they would have benefitted from reading this to learn, hence, I write on.

The Three B's: Blurb, BCC, Boomerang

One of the companies I worked with last week, Vidcode, is building a business to address the pipeline problem in software development. I had a contact at Google to whom I wanted to make an intro. I asked the co-founders to send me a blurb (3-4 sentences that summarized their company and what they were hoping to get out of the connection) that I could pass along in my e-intro, and used it as an opportunity to recommend that next time they wanted an intro, they could proactively offer to share a blurb with the connector, in order to increase the likelihood that said connector would follow through.

I then explained that sometime in the past couple years, "moving you to bcc" has become an industry standard in responding to e-intros, and that not adhering to this convention may subtly indicate you're new to the game and make it less likely to be taken seriously. It took me a few email exchanges with VCs to pick up on this back when I started, and because this convention does not exist in the education realm, it's especially important for first-time education entrepreneurs to be aware of the "accepted" way to address a new connection from the get-go.

Lastly, Boomerang (or similar email plugin). I basically proselytize Boomerang by explaining that most likely the person to whom you have just been introduced is very, very busy. Making sure that first-time entrepreneurs don't interpret radio silence as lack of interest is key. If there was one takeaway I left with the 4.0 Launch cohort, I hope it was "Boomerang every outbound email" and if no initial response, always followup.

The Check for Understanding

It's one thing to explain these techniques. It's quite another to followup and make sure that what you taught is actually sticking. Here's exactly how I did this:

To: Alex, Vidcode co-founder
From: Me
Subject: another lead

Spoke with the head of [local school board] the other day - he mentioned that one of his schools would be interested in learning about Vidcode. Wanted to double check that you'd welcome the intro and sales opportunity before I made it. Please let me know.

Also, were you able to connect with Tara [original person I e-intro'ed them to last week]?

To: Me
From: Alex
Re: another lead
We haven't heard back from Tara yet.  I'll shoot her another email tomorrow AM to touch base?

I've followed Joe Manko, Principal of Liberty Elementary School in Baltimore, on Twitter for a few years now. So I was pretty pumped when I found him live-tweeting the same session at a conference I attended recently and got to meet him in person.

Fast forward a couple weeks, and I just had the pleasure of visiting his school.

Some observations -

1. The average number of years of teaching experience at Liberty is 14. Two teachers just celebrated their 42nd year of teaching. (!!!) Seeing them in action (the summer program was in session during my visit), it is immediately apparent how much we grossly undervalue the power of experience in the public discourse on education reform.  

2. Because of the experience level of the teaching staff, and the leadership responsibilities they take on, Joe is the only administrator. No APs, no deans. This frees up budget for 5 full time interventionists, a social worker, and a speech pathologist. Note that the school is a 90-90-90 public district school (no admissions requirements). That means 90% of the students are performing on grade-level, 90% are students of color, and 90% qualify for free and reduced price lunch.

3. The tour of the building was quite a dog and pony show. Literally. Joe actively builds partnerships with community organizations to bring resources into the school. Liberty has a school dog as part of a pet therapy program, and the students have been training service dogs for several years. They also work with a local farm to bring horses to campus once a month (and daily during the summer!). Students use their "behavior bucks" to purchase pony rides (5 Liberty bucks). Or the full pony package (20 Liberty bucks) gets them a ride and the opportunity to feed, groom, and generally learn how to take care of the animal. An interventionist on our tour referred to this as the humane education movement, something I wasn't previously familiar with.

4. The children's art was EVERYWHERE. Walls. Ceilings. Windows. Pretty much every inch of space that wasn't covered with student writing samples was covered with art. They'd even wrapped colored ribbons around the railings in the stairwell just because. Metal trash cans had become painted masterpieces. The net result - you couldn't help but feel the joy and love and warmth in the building.

5. Best (and easy to implement!) display of data to demonstrate student growth in writing: outside of one 2nd grade classroom, each student had three pieces of writing posted side-by-side: from beginning, middle, and end of year. The growth in word choice, sentence structure, penmanship was a powerful visual display.

6. Yes, there was technology - in several classrooms, students were on individual iPads researching animals for their reports. I was struck by how unremarkable this was (in a good way) - the iPad was just another tool along side the construction paper, glue, and scissors. A few bulletin boards featured QR codes that linked to students' writeups on volcanos - again, I noted how subtle this use of technology was.

7. They're building a fablab in the library and have raised money for 3D printers and the like. Kids are already making things with Raspberry Pi, Arduino, and Makey Makey, and learning Scratch.

Biggest takeaway was the school's obvious commitment to the whole child, and the balanced investment in experienced staff, community partnerships, and the mix of modern and old-fashioned tools for kids to be creators. Far too often in the debate about education reform, we're pitting teachers against technology, or dangerously narrowing our definition of education to academic content mastery as demonstrated by standardized test performance. Liberty was as refreshing reminder that is in fact possible to be a neighborhood public school that takes a wider, holistic view.

Came across Hacker School's User Manual last night. For those unfamiliar, 

Hacker School is a free, full-time, immersive school in New York for becoming a better programmer. We're like a writers' retreat for programmers. People come from around the world to write code and grow as programmers.

Take three minutes and go read the part about Social Rules. I'll still be here when you get back.

Subtle -isms are small things that make others feel uncomfortable, things that we all sometimes do by mistake. For example, saying "It's so easy my grandmother could do it" is a subtle -ism. Like the other three social rules, this one is often accidentally broken. Like the other three, it's not a big deal to mess up – you just apologize and move on ... If you are a third party, and you don't see what could be biased about the comment that was made, feel free to talk to faculty. Please don't say, "Comment X wasn't homophobic!" Similarly, please don't pile on to someone who made a mistake. The "subtle" in "subtle -isms" means that it's probably not obvious to everyone right away what was wrong with the comment.

Breaking the fourth social rule, like breaking any other social rule, is an accident and a small thing. In theory, someone should be able to say "Hey, that was subtly sexist," get the response "Oops, sorry!" and move on just as easily as if they'd well-actually'ed. In practice, people are less likely to point out when this rule is broken, and more likely to be defensive if they were the rule-breaker. We'd like to change this.

For the last year, the "No subtle -isms" rule has carried some implementation guidelines. One of these is asking people not to debate whether or not something is an -ism. When we introduced this policy, many women in our community responded positively. At the same time, some men described their process of discovering what their female friends were going through, and worried that other men would miss out on this opportunity to become allies. That's a genuine cost of having this policy. Nevertheless, we believe that this cost is outweighed by two benefits. First, we want marginalized people to feel welcome, not like they have to defend their presence. Second, we don't want marginalized people to have to spend time educating non-marginalized people who might be coming to these ideas for the first time. Faculty - not other Hacker Schoolers - are happy to help people discover resources for learning about anti-oppression.

• Should you apply to Hacker School? (On applying: "Statistically speaking, if you’re a woman, you’re more likely to be underestimating your ability. Hacker School can’t accept every applicant, but please don’t reject yourself.")
• Mistakes We've Made
• Announcing the Fog Creek Fellowship with Flatiron School
• Do I Really Love Programming?
• Diversity and Startups (It's interesting to me to compare YCombinator's approach to solving this problem, and language choices in their blog post, to the Hacker School posts.)