Dropout Chronicles — Episode 3: Becoming Silicon Valley #Basic

Hallie Lomax
7 min readNov 15, 2017


Step 1: Drop out of school ✔
Step 2: Move to the Bay ✔
Step 3: Start a start-up ✔
Step ?: ????

OK, story time:

Let’s rewind here for a minute, cuz there’s a lot of catching up to do.

In last year’s episode, I left y’all hanging with some weird handwaving about joining a company full-time, with a bit of info on the few months I spent stress-interviewing and interning leading up to that point. To be a little less vague, for those of you who don’t stalk me on LinkedIn, that place was LendUp — a social-good start-up that strives to be an ethical alternative to payday lending.

As someone who hopes to one day be a good person, I thought surrounding myself with morally-driven smart people definitely sounded like a step in the right direction. Not only were we all professionally in the business of trying to make the world a better place, you could also see it reflected in the smaller day-to-day decisions people chose to make. Like when a shoe-shiner outside of our building got hit by a car, and a slack channel was immediately made to share updates on how he was doing, and post links to resources for sending him help. Or how a book club was started to read about how systemic racism impacts our society as a whole. Or when the founders sent a message out to the company telling people to go home if they needed a mental health break after a week of back-to-back police shootings took over the news.

Basically, you really learn how to be socially conscious when it seems like everyone around you is already #awake.

So why’d I leave? Good question. Keep reading, and maybe you’ll find out.

Last year was an interesting year, to say the least. We got a new president, and some people had opinions about it.


While carpooling to SixFlags with some of my housemates in the Fall of 2016, we got into a conversation about encouraging a stronger millennial turnout for the upcoming races. We figured a quick way of lowering the threshold would be making voter registration a whole lot easier. The next week, we started meeting together after work to hack something together.

Fast-forward a few more, and hello world — its VotePlz.

You can read more about it here. If you look at the comments close enough, you can catch these hands typing out some strongly-worded opinions on why voter disenfranchisement is an issue we should all care about.

“Wait, is this what you left LendUp to work on??”

Short answer: Nope.

Long answer:

In the months leading up until VotePlz became a thing, I’d started to feel this void inside me growing, and I had no idea what was causing it. I felt unfulfilled. On paper, I shouldn’t have had anything to complain about: I had a steady job at a company with a meaningful mission, surrounded by talented people who shared my dream of a world with less financial insecurity. What more could I have asked for — especially in a first job — as someone who didn’t even finish school?


When VotePlz first started, I felt this immediate pull at my heartstrings. It quickly took over most of my thinking during the daytime. Even when I was working on tickets at LendUp, I would daydream about closing some of VotePlz’s GitHub issues. In my one-on-ones with my manager, it was the only thing I could talk about. So, with his approval, I started taking every Tuesday leading up until the election off to work out of the VotePlz office. He thought it would be a good use of my mandatory vacation time, since I’d apparently forgotten to use it that year.

For all intents and purposes, I was having an affair. And, much like any affair, the thing I was cheating with turned out to just be a distraction from what I really needed, rather than the answer.

You see, VotePlz operated as team of <10 people, and, even there, I felt like my contributions as a volunteer engineer were negligible. It made me feel more individually important than my full-time gig, which is how it drew me in — but it still wasn’t enough.

It was while working there that I realized, though the work I did was important, I wasn’t what made it important. LendUp and VotePlz would both still be what they were without me, and that’s why I couldn’t personally find meaning in the work that I did for either of them.

Answer: It was time to do my own thing.

A question: What should I do?

Through a series of conversations with some people whose opinions I value, I came to the conclusion that the growing economic inequality in this country is arguably the greatest driving force for the issues that we face. You could easily make the argument that most forms of group-based hatred — from racism, to sexism, to xenophobia — are fueled by the anxiety produced living paycheck to paycheck, and the fear of losing one’s livelihood to some existential “other.”

And while sociopathic capitalism — which creates an environment where large corporations lobby against minimum wage increases, call for decreasing taxes on the wealthy, and attempt to cut financial services to the poor — pulls at one end, the prison industrial complex pulls at the other. It targets poor people in low-income neighborhoods, and makes it harder for them to find work after release by holding their records over their heads for the rest of their lives. This increases the likelihood of them returning to prison, and staying trapped in a cycle of poverty.


A follow-up: How should I do it?

I had this theory that a good starting point would be helping people with criminal records find work, but I wasn’t sure the best way to go about doing that. I figured a pretty straightforward way to find out would be to ask people who knew more than I did.

This was a space that I had no experience operating in, so I was very transparent about how little I knew, which made people open up a lot about the ups and downs of working towards this overarching goal of reducing recidivism rates.

Through these conversations, I started to see some patterns in problems people were facing, and began to form ideas around how I could help tackle them with the skills I already possess.

But I’ll save those details for next time.

The important takeaways here were that I

  1. Knew I wanted to do something else, and
  2. Knew what I wanted to do

The only question left was: When should I do it?

Insert: The Tipping Point

Earlier this year, something pretty traumatic happened to my family. For the sake of the specific victims’ privacy, I’m not going to go into details about what exactly that was.

What I will say is that, between the charges, the fact that everything was caught on camera, and that the perpetrator has admitted (without remorse) to what they did: someone is very likely going to spend the next 25 years behind bars.

And while I will admit that I have very little — if any — actual empathy for this particular individual, it’s really hard to ignore the fact that they’re younger than me, and that this New Year’s Eve will be my 25th birthday.

What’s even harder to ignore is that we lock a lot of people up for doing a helluva lot less. And that all of the money and resources we waste putting those people away means the likelihood of this one specific person getting rehabilitated is low.

What could I possibly spend my next 25 years doing that would be more important than making sure their time doesn’t go to waste?

Leaving LendUp

The more awkward part of the timing around my decision to leave was the fact that both of the founders were out of office (Sasha was on paternity leave, and Jake was in Italy), and I didn’t really want to officially start telling people I was heading out until I let them know.

Because I’m mostly the worst kind of person, I sent Sasha one of those “I need to talk to you at some point” messages no one ever wants to see, and he ended up calling me while on leave, which I still feel a little bad about.

I word-vomited all over the phone everything that had been on my mind, and he quietly listened from start to finish — all the way up to me saying that it was time for me to go.

It was then that he told me the story of when he realized the important role building good credit played in helping people gain financial independence:

“It was like seeing a problem that I couldn’t unsee.”

He said he understood that this was something I needed to do, and that — though he was sad to see me go — he was happy to see where I was going. He actually even went on to write a blog post about me and a couple of other people leaving to start our own purpose-driven companies, and I still can’t really get over how cool that was of him to do.

Next up: Jake.

As I alluded to in my last post, a conversation I’d had with Jake was what helped ease me into making my decision to join LendUp in the first place. On top of that, in the months leading up to me deciding to leave, he’d been acting as my direct manager. We even had a one-on-one scheduled the day that I got the news about what happened to my family, and he told me to leave early and take a few days off to collect myself if I needed them (which I did).

In hindsight, it really shouldn’t have come as a surprise that he’d also understand.

As I started to let more people in the company know about my next steps, I found the support to be pretty overwhelming.

I don’t know how people put up with me

Anyways, that’s been me. Its been almost 6 months since I left, and the ride’s put me through a rollercoaster of emotions. I’ll tell ya’ll more about it once I’ve finished processing.

To be continued…here!

If you liked what you read, please hit the clap-dooter and give me a follow~

In case you missed it, don’t forget to checkout Episode 1!