Playing the Long Game

Danielle's sustaining motivation for working on 1517

Nick is the most quiet of us, at least externally, at 1517. But he’s one of those quiet but deadly types. You’re not going to see him on Twitter much — he keeps a low profile, but he’s always insightful and thinking about the big picture. He’s great at keeping us on the right path with our mission and is very intuitive.

We were talking about how our standup meetings have become more tactical and to be honest, boring. He posited that our best meetings have centered around big questions that have gotten us into a creative flow and brainstorming. Surely harder to do over Zoom, but certainly worthwhile to try (and since drafting this post over a week ago our Zooms have gotten better!). One great question that Nick put out, that I realize our team has yet to answer either really to ourselves or publicly, is “Why are we each individually doing what we’re doing at 1517?” We ask teams about their motivations regularly, we need to take our own medicine.

For Nick, it’s about accelerating technology and directing our world into a brighter future — but he’ll have to write more here as that’s not my story to tell. That said, what I saw is that our reasons are quite different from each other.

For me, 1517 comes from my own personal mission to empower young people to have freedom and autonomy in their lives. Side note: For a while now I have wondered if the world of crypto could open up to minors because I think once “children” are considered more a part of the economy that additional freedoms (at least in some of their decision making) could be granted to them, or at least not taken away (I could likely write a much longer post on this point alone but I’m putting it here for time keeping’s sake). I crafted my personal mission statement in 2003 after figuring out that I was headed towards grad school for all the wrong reasons and wanted to get back on a path of doing work that lit me up from the inside out (thank you Zen and the Art of Making a Living for helping me to craft what has been nearly two decades of positive impact).

What’s great about having a personal mission isn’t that you know what the path laid out will look like, but that you will know in your soul if you are going in the right direction or not even when the destination is unclear — a personal compass.

After figuring out my calling, it pulled me into action to start my own tutoring company, Heightened Learning. For the first year of running my business I worked with children in private and public school, mostly teaching math. My edge was in teaching students using their cognitive strengths which I had been trained in assessing from my time in the Neurology department at Beth Israel Deaconess Medical Center as well as teaching towards students’ passion and interests. But neither public or private school students at the time had much freedom or autonomy and there was only so much I could bring to them besides some relief at having support and gained skills.

It was probably towards the end of my first year running my business that I randomly met my first homeschooling family through Craigslist (it used to not be creepy long ago in a far away land). I was accustomed to non traditional education but hadn’t been able to work with a family so intimately. I say intimate because it was more than tutoring, I got to know the lives of the children and especially the mother. We would talk sometimes for hours after sessions and through osmosis I got to learn more about how they had chosen to do something different for their family and the ups and downs therein — in the words of startups, I was taking customer discovery to the extreme. I loved working with them because the children were working in a more free environment where they could choose their interests and go at their own pace. I was no longer homework help and feeling like a bandaid for a bullet wound for my students in a more institutional environment.

Around 2005 I received an interesting inquiry. I got a phone call from a woman named Christine Kuglen:

“Hi, we have a small secular homeschooling co-op here and I heard that you teach creative writing. We’d love to have you teach a class for our group since none of us can get our kids to write. It’s mostly boys around 9 years old.”

I had no idea where she got the idea that I was a writing teacher — I had tutored some in writing, but never taught a class in anything. Fake it til you make it they say…

“Yeah, that sounds great, I’d love to teach a class for you!”

And we started just a couple weeks later.

The co-op was held in Christine’s house. A lot of people think homeschoolers then and now must have lots of means. This particular group was very mission driven about why they homeschooled their children and it was clear that they were giving up a lot to do it. Christine’s house was chaotic to say the least and the co-op kids would jet around because rooms and activities. My writing class would take place in a converted garage with fold out tables and chairs.

That first lesson felt a bit like being on trial. Ten-ish kids in the class and an equal number of moms (some with young children on the hip) in the back watching what I was doing. This co-op didn’t hire out much as the parents taught most of the classes.

I don’t remember what topics I brought up that day but I do remember the moms accosting me at the end of class with their desires for what each of their children would learn. It took a little time, but I got them on board with what I wanted to do which was to do a more Socratic dialogue based class — bringing up big ideas in philosophy and engaging their thought process over getting them to immediately put pencil to paper. We’d get to writing with time.

One of the boys, Alec, had a blonde jew fro to put it mildly and would often stick things in it, I imagined as adornment. He had a big smile to go with his cherubic body. And he was whip smart and very articulate but couldn’t hold a pencil to save his life. By the end of our class he was writing whole stories and no longer hated the process.

I remember those days fondly of discussing big ideas, learning equally from them since most of the children had the time and motivation to deep dive on topics within history and the sciences. I’d take their papers home and spend quite a while reading through each piece and offering feedback on what they had produced. We didn’t believe in traditional school though — so there were no grades, I was just “Danielle” to students, and we’d build our studies together.

This co-op group was really showing me what was possible in terms of learning in an environment where young people are respected for their abilities and how we can collaboratively learn from each other — they were my tribe.

In 2006, Christine and I, would start a charter school Innovations Academy to scale our work that we started in the co-op to families that didn’t have the opportunity to do independent learning. Today our school is respected as a best school in San Diego and teachers from around the world visit to observe our methodology — focused heavily on a social emotional foundation that lays the groundwork for great learning. We serve 400 children a year and I’ve been on the board for 15 years and directed the school for the first two years. It’s been the best and most challenging thing I’ve ever done. I was able to cut my teeth on founding a larger organization and running it — many parallels to startup stories (having funding, losing funding, hiring/firing staff, over time making the delta smaller between what we envisioned our school to be and where/how we got started) but in a nonprofit package.

Two weeks ago I heard from Christine’s son, Martin. I’ve watched Martin grow up since he was about seven. He’s in college now and has always had very deep interests. When I was at the Thiel Foundation, he attended one of our summits and began being mentored by an expert in chemistry. He wanted to touch base about a new project he’s working on so we scheduled some time and I thought nothing more of it.

I hop on Martin’s Zoom and my brain starts to break a little bit. There are five people on the call and I start looking at their names and then doing triple takes. “Nick E. wait, is that you?”

“Hi Danielle! It’s been a long time.” And he shared that he still has a very vivid memory of me teaching him ergonomic hand position.

My eyes scan another team member: long blonde intensely curly hair with something like a hair comb sticking straight out of the top, thin face, and then I look at his name.

“ALEC?! WOW!! Oh my god, that’s you. You look SO different!”

I am speechless for a second collecting myself. This team is mostly made-up from children in that first  creative writing class and one young man who attended Innovations Academy in the first year.

I start feeling a bit overcome. Imagine being the person who used to help these same children to get their thoughts coherently on paper, working out of a dimly lit garage, offering them writing prompts (“If you could change one thing about our world, what would it be?”) and now asking them how their work might be venture scaleable, if they have novel IP, and what the division of labor on the team is. My mind was breaking not just noting their growth, but also my own. When I started working with them in 2005 I could have never predicted that I’d be working in venture capital (I didn’t know what VC stood for 10 years ago) let alone running my own fund.

I collected myself and heard their pitch — a part of me so proud to see how far all these young men have come and in addition knowing their journeys of their families overall. Our first call was more conversational and this week we’ll have a more formal pitch meeting between their team and mine about potential investment.

People often ask me how my past ties in with what I do today and of course I explain my personal mission and connect the dots for others. I just didn’t ever see it coming that my own students would be pitching me 16 years later.

For me, 1517 is another instantiation of my personal mission. At our last team retreat a couple months ago the four of us were brainstorming that we have gone from being a fund (having a single investment entity), to a firm (having multiple), to now moving towards becoming an institution. That said, we have always seen ourselves as more than a venture firm -- we see what we do as building a new type of self directed educational institution for misfits and mutants (in fact we are kicking off a program where our founders can use the title Scholars in Residence at 1517 as part of their education or work experience and as they progress they will graduate to Faculty at 1517 and pay their knowledge forward). Our community members and founders educate themselves through building a company and novel technologies rather than at the hands of a bureaucratic institution.

If you’re a high school, college student, or without a BA/BS degree (or work with these groups or know someone that would benefit) we’d love to hear from you about what you love to build! We offer grants, investments, workshops, and community to help you get ahead and plug you into other likeminded and passionate peers. And if you’re part of a school that fosters a different type of learning environment that empowers young people to have agency, we’d love to work with you and your students!

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