Joining Boldstart

Work is an ambiguous word. We use it to convey two completely separate concepts. Our "work" is what we do to make an income to fund our life. Our "work" is also the thing that we create, a labor of love.

As it turns out, the two types of work completely overlap for me - it just took a long time to figure that out1. While I figured out what to do after Dark, I joked that I just wanted money to appear in my bank account, so I could keep doing what I was already doing.

Because so much of what I like to do is help founders and startups, I've thought about going to a fund on-and-off since 2013. I never took the plunge because most of the time (rightfully) investing means you don't get to build! Most funds separate investing and platform. There are good reasons for this, but not every fund is the same. Because Boldstart is hyper-focused on being great for pre-product, dev-focused, enterprise companies, they can interweave the two.

I got to know Boldstart when they invested in Dark. I don't know many investors who are willing to sit down and code in order to give you feedback. Boldstart did, even when people described our user tests as "like being on a terrible job interview." Every fund likes to say they're the "first call," but Boldstart was always mine. Ed, Eliot, Shomik, Natalie, Charlotte, and Max have built something really special.

They're still willing to experiment with their platform to help founders. We created my role as an experiment, and we'll see how it evolves. My priority is making sure this work continues to help other founders, and feedback on that is always welcome. Generally speaking, this job means I will do "everything I was doing before."

Things I do

(Angel) Investing

Over the last couple years I've been writing angel checks. I love being able to learn from and help founders. If you reach out to me about investment, you should be hoping for money from me! I'm still going to be doing that. My default assumption will be that you're talking to me as Ellen, a founder, who happens to be at Boldstart right now. That said, I have a lot of leeway. If I'm interested individually and more support from Boldstart is interesting to you, we can talk about it (yes, this is intentionally vague).

Extra Hands

Being a founder is hard. Sometimes you wish you could clone yourself. Boldstart was already a first call for me, but sometimes you need more than a call. It's time to help with learning how to do something, or executing on it. I can take the call, and I can take a few weeks to work on content, community, or user research, or metrics for anyone in the portfolio.


I've made a lot of mistakes, and have a pretty length list of "I wish someone would have told me X" from my time at Dark. From talking to friends, a lot of us make the same mistakes (even after stints in other early stage startups!) Plus, things move quickly. Being an extra set of operating hands means I'll see the most common issues that our founders are facing today. I love figuring out how to make that information available. My goal is to create ways to improve the first 180 days for every founder. This will be a lot like all of the work I put into demystifying Product Management between 2013-2016.

Founding Something New

I alluded to this at the beginning, but here it is: you'll see another company out of me. I don't know when the right set of things will align, but when they do, we're all on the same page about that.

I'm excited to join Ed, Eliot, Natalie, Shomik, Charlotte, and Max in partnering and supporting early stage founders! It's an experiment. You can learn more about Boldstart at

Want to chat? Curious about the mechanics between getting a job like this? Wish a piece of content existed? Something went really well and you want to share your story? I'm or AMA on Twitter, @ellenchisa.

1 I've had five real "gaps" from professional jobs, all of which slowly turned into this type of work:

  1. Started Alight Learning, and tried understand engineering education.
  2. Invested heavily in The Awesome Foundation and building local community. This ended up with me having the "job" version of that, and joining Kickstarter.
  3. I taught my first full length course at GA, which eventually led to writing pm@olin.
  4. The fourth became Lola.
  5. The fifth resulted in this experiment.