Tent Talks Featuring Cassidy Williams – Connecting Worlds: The Synergy of Tech Expertise, Creative Pursuits, and Community Engagement

Tent Talks Featuring: Cassidy Williams
Cassidy Williams
Cassidy loves to make memes and dreams and software. She's currently the CTO at Contenda. She's worked for a variety of companies, large and small, advises startups, and she's had the honor of working on the board of various non-profits.

Join us for a dynamic Tent Talks session with Cassidy Williams, a renowned startup advisor, investor, developer experience expert, and all-around tech innovator. Dive into an engaging conversation that explores Cassidy’s journey through the tech world, from her early days to her current role as CTO of Contenda, and her myriad side projects that blend creativity with technology. Discover how Cassidy balances her passion for development with her dedication to community and education, offering insights into her approach to productivity, learning, and navigating the tech landscape.

Expect to leave inspired by Cassidy’s experiences and advice on how to carve your own path in tech, balancing professional growth with personal projects and community involvement. Whether you’re a developer, aspiring tech professional, or just a tech enthusiast, this session promises valuable takeaways on innovation, creativity, and the power of a supportive tech community.

Session Notes

Session Overview

In this engaging episode of Tent Talks, Cassidy Williams, the CTO of Brainstory.ai, shares her insights on thriving across varied tech environments, balancing side projects with professional responsibilities, and her passion for education in the tech industry. Cassidy discusses her approach to career decision-making, her creative process behind innovative projects like W9 Crafter and Jumblie.com, and the role of teaching in her life. She also provides a look into her personal productivity system and continuous learning strategies in web development.

Navigating Varied Tech Environments:

  • Cassidy emphasizes the importance of self-audits to determine personal and professional likes and dislikes, strengths, and weaknesses.
  • She mentions that these audits help her decide when it’s time for a change, ensuring she’s always aligned with her interests and skills.

Side Projects and Balance:

  • Discusses the genesis and development timeline of her side projects, such as W9 Crafter and Jumblie.com.
  • Highlights the use of the Obsidian app to organize ideas and manage time efficiently, especially around her responsibilities as a new mother.

Passion for Education:

  • Cassidy shares her drive to provide learning resources she wished she had when starting in tech.
  • She recounts impactful moments in education, like helping friends secure jobs through her guidance and resources.

Organizational Techniques and Productivity Tools:

  • Describes her reliance on digital tools like Obsidian, Brainstory, and others for productivity and organization.
  • Cassidy values scheduled planning and strategic use of apps to manage her diverse commitments.

Adapting to Technological Changes:

  • Cassidy uses her newsletter as a tool to stay updated with new technologies, ensuring she reads the materials she recommends to her audience.
  • She explores building projects from scratch to deepen her understanding of new technologies without relying on libraries.

Notable Quotes

  • “Do a life audit regularly to figure out if you are where you want to be.”
  • “I want people to have the resources I didn’t have when starting out in tech.”
  • “Using a calendar and obeying it helps me stay organized amidst my busy schedule.”
  • “Having a baby has made me very efficient with my time.”
  • “Seeing people succeed as a result of my help is immensely gratifying.”
  • “It’s fun to build something from scratch, to be close to the metal with the browser.”
  • “Paying it forward and lifting as you climb benefits everyone.”

Reference Materials

  • Obsidian: A versatile note-taking application that allows users to create a linked network of notes. Cassidy uses it extensively for organizing project ideas, writing newsletters, blog posts, and general note-taking.
  • Brainstory: Described as “rubber duck debugging as a service,” this tool helps users articulate and refine their thoughts through Socratic questioning. It was developed to facilitate deeper thinking about projects or problems, simulating a conversation with a bot instead of a human.
  • W9 Crafter and Jumblie.com: These are examples of Cassidy’s side projects. W9 Crafter was developed over a few years and aims to simplify tax-related processes, while Jumblie.com is a fun word game created in just a week to accompany a video project.
  • Raindrop: A bookmarking app that Cassidy utilizes to save and organize web resources effectively. This tool is handy for keeping important links accessible and categorized.
  • Sukha: An app that combines Pomodoro-style timers with focus music, helping to enhance productivity through structured work and rest periods.
  • Dabble.me: A journaling app that Cassidy tries to use daily. It helps her keep a personal log of her thoughts and activities, which is beneficial for reflection and mental organization.
  • todometer: Another one of Cassidy’s creations, this app is essentially a glorified to-do list with a progress bar feature. It visually represents task completion and allows for task pausing, enhancing the satisfaction of seeing tasks completed.

Session Transcript

[00:00:34] Chicago Camps: Cassidy, with your vast experience across startups, major tech companies, and now as CTO of Brainstory.ai, what’s your approach to navigating and thriving in such varied tech environments, and how do you decide what’s the next right move?

[00:00:50] Cassidy Williams: Great question, because I think a lot of it comes down to me just trying to not be bored, which is probably not the best answer to that question. I love working with startups and I’ve worked with some larger tech companies and I once read something that you should regularly do like a life audit of yourself and ask yourself some very honest questions.

And the four questions that I started to ask myself regularly were what are the things that I like? What are the things that I don’t like? What are the things that I’m good at? And what are the things that I’m not good at? And then just breaking that down and being very honest with myself, because those things can change and morph over time.

And I try to like, actually sit down and do that regularly, and I think in doing that and being very honest with myself, I can learn, Okay, clearly the role that I’m in currently isn’t the one that is for me. And it’s like something that I’m good at, but it’s not something that I like doing right now.

So maybe I should start considering something. And that sort of thing. I do those kinds of audits and I think that’s just helped me navigate around and know like when it’s time for a change or when I’m doing what I want to be doing and it’s led to a lot of really good conversations and just learning opportunities as well.

[00:02:05] Chicago Camps: You’ve created some incredible side projects like W9 Crafter and Jumblie.com. Can you share how these projects begin for you, what your process is from ideation to launch, and how do you balance these projects with your primary work responsibilities?

[00:02:21] Cassidy Williams: So a lot of my projects, I ship them, but it takes a long time.

I will say that W9 Crafter one, I first pitched that to friends three years ago, and I finally shipped it about a month ago. So that’s how long it took for me to actually do some of those. Although Jumblie, that was one where I just thought it’d be fun to make a word game. And a friend of mine asked me to do a video with him and I was like, Oh, I’ll make a word game for the video.

And so that I got done in a week. So really the time span truly varies, but yeah, a lot of those projects just began with me wanting to do something and finding some time in the day to do it, where I use the note taking app Obsidian and I could talk your ear off about it, so I won’t go too deep into it, but I do everything in Obsidian, write down project ideas, write my newsletter, write blog posts, all kinds of things, take notes on general topics, and I just have a project ideas tag where every single time I think of something that might be a good idea, I just tag it with a project idea and then move on. And so if I ever want to get my ideas out and code on something, I consult my list of project ideas and pick one. So that’s the ideation side where I start by just this would be a cool app. Yeah, I’ll just write it down. Can’t do it now, but I’ll do it eventually. 

And then actually working on them and balancing. And yeah, my baby turned one yesterday, whoo, but yeah that’s a whole time commitment in itself. I don’t get very dedicated blocks of time where I can work on something, but I will say having a baby has made me very efficient with my time.

Because I know if she’s napping, I’m like, okay, I have anywhere between 20 minutes to two hours. Okay, I’ll just do what I can in this time span. Or if she goes to bed after a certain hour, I’m just like, okay. Before I get sleepy, I have about two to three hours, I’m just gonna do what I can do. And so it has been a forcing function for me to actually work on things that I want to work on in the limited amount of time that I do have to be able to.

[00:04:17] Chicago Camps: Your commitment to teaching and helping others grow their coding skills is evident from your weekly newsletter to offering resume reviews and mock interviews. What drives this passion for education and what has been one of your most rewarding experiences in this arena?

[00:04:32] Cassidy Williams: Oh man, I just love teaching people.

I think it’s so fun. And I think in general, too, I want people to have the resources that I didn’t have when I was getting into the industry because there, a lot of the things that I learned, like I stumbled upon tech where my parents aren’t very technical people. When I was in middle school, I heard someone say, check out my website when I was walking home from school.

And I was just like, wait, you can have one of those and truly just started learning how to code from there. And this was before even YouTube and stuff. And so I was like viewing the source of websites, figuring out like what HTML tags meant and everything. Cause I didn’t know how to learn it. And granted, there’s so many other resources out there now and so many things out there, but to the point where there’s probably too much, but I love being able to help people not be just like in the dark, trying to flounder and find their way through the way I did. 

And I think it is so fun to be able to get that aha moment when someone, when it clicks for someone or where they say, Oh, actually, wait, this was really valuable. 

And so many people in the tech industry have given so much to me and provided so much to me as I was floundering, figuring things out that I want to be able to give back to everyone.

And there’ve been so many good experiences with it. It’s hard to pick one. One of them was probably a friend of mine where I helped both him and his partner with some mock interviews and resume reviews, and then they both got jobs and they both just said, thank you for employing our entire household.

So that was probably the funniest one, but it’s always just really gratifying to see people say, hey, the practice that I got from your newsletter and the coding questions, that helped me with my interviews and I got a job as a result. And just hearing people get jobs and get roles and figure out their next thing is so satisfying.

And it’s, I’m so happy to be able to do that. And I also think that in general, a lot of companies and organizations are geared towards the more advanced people, like you say, because that honestly, that’s where the money is. And so if you can provide that kind of support to people early in their careers, it just plays out tenfold.

It’s a long game, but it helps people so much more in the long run. 

[00:06:42] Chicago Camps: With your busy schedule, how do you keep yourself organized and productive? And could you share some of your favorite note taking techniques or productivity tools that help you stay on top of your diverse projects and commitments?

[00:06:54] Cassidy Williams: I’ve talked about Obsidian.

I’ll get into a little bit more of that, but I think for the main organized and productive thing, it’s I use a calendar. If I need to dedicate times to it, I just put it on a calendar and I just obey whatever the calendar says and that has seemed to work so far. And so if it’s on the calendar, it’s going to happen.

And sometimes it’s just like an all day event where it’s eventually at some point today, you need to write the Stack Overflow newsletter. It works. It’s a job done, or sometimes it’s just like a dedicated half hour here and there to do stuff, but in terms of other tools, again, Obsidian, that’s where I write all the things, even if it’s just like to get a thought out of my brain, and then also to be a shill, I use Brainstory. What that is, it’s a tool for helping you talk out your thoughts.

Tech people, I usually say it’s rubber duck debugging as a service, but what you do is you talk things out and it uses Socratic questioning to ask you questions and force you to think a little bit deeper about what you’re working on. And so if I ever have a project or a problem or anything, I usually like to talk it out, which is why we started to build BrainStory because people didn’t want to talk to me.

They wanted me to talk to a robot instead. I like using tools like Brainstory to be able to talk out my thoughts, whether it’s Obsidian or Brainstory. I spam it somewhere. And then I use some tools like Raindrop for bookmarking. I use an app called Suka to, that’s of Pomodoro timers and focus music and stuff.

And then I use an app called Dabble.me, Dabble.me, that is like a journaling app that I try to do daily. And so I think that’s generally the tools that I use day to day. I usually use digital things, but the way I describe it and the way my husband can tell is the more I’m actually physically writing down, the more stressed I am.

Cause that’s something where I like actually physically writing down is helpful, but then if it’s just a note I can do for later or something I can do for later, I’ll just put it in Obsidian and move on. I built another app that I didn’t even mention called todometer, but todometer, it’s literally a glorified to do list, but it has a progress bar.

And so as you check things off, a little progress bar fills up, and you can also pause tasks for later, but that’s it. But I like checking things off and getting a little satisfaction from that. 

[00:09:09] Chicago Camps: Given your extensive background in web development, how do you stay adaptable and continuously evolve your skills amidst rapid technological changes?

[00:09:18] Cassidy Williams: My newsletter is a big part of it because when I am curating links for my newsletter, I force myself to read the articles that I’m actually having other people read. And that’s been really helpful to keep up with just okay, this is the latest thing that’s out now, or this is the latest thing that this publication came out now.

And that, that definitely helps a lot. And I think a combination of writing my newsletter, sharing content, and then also just building like building side projects or building a prototype or something that has forced me to experiment with libraries that I wouldn’t normally experiment with or read something I wouldn’t normally read.

And I feel like those are the core things that help. And in terms of being adaptable, I definitely. established principles that I sometimes I’m a bit more lax on here and there, depending on what I’m working on. And lately, my latest thing is seeing what can I build without using any libraries whatsoever, fully from scratch?

How painful will that be? Probably very painful, but it’s still fun to be close to the metal quote unquote with the browser and then seeing, okay, this is where this kind of library will help, or this is where I can do like minimum viable product in just the basics and then add more of them later. And so it forces me to learn a little bit more deeply.

Pay it forward might be the latest and greatest trendy one or lift as you climb. As you are moving up in your career and navigating different things, if you’re helping others, teaching others, as you go, you’re just paying it forward to the next person, you’re lifting the person up to where you are so you can keep moving up as well.

Event Details
Connecting Worlds: The Synergy of Tech Expertise, Creative Pursuits, and Community Engagement
April 22, 2024
4:00 pm
April 22, 2024
5:00 pm
Tent Talks Featuring Cassidy Williams Connecting Worlds: The Synergy of Tech Expertise, Creative Pursuits, and Community Engagement Join us for a dynamic Tent Talks session with Cassidy Williams, a renowned startup advisor, investor, developer experience expert, and all-around tech innovator....


May 2024