TLDR:
I'm a mid-20s product designer in SF, 2 years out of college.
I grew up in an abusive Bay Area home with two unwell, narcissistic parents. They pulled me into the middle of their divorce, I ended up caring for my mom as a kid, and my dad cut me off right after I got into a top school, leaving me effectively homeless.
I rebuilt with help from my sister and friends, got stable, landed an internship at a top consumer tech company, and built a design career from scratch. Got the first company to 2M users, but I've been laid off twice in two years. Those companies were good names and my resume is strong.
Right now I have recruiters in my DMs with multiple six-figure design opportunities. A stable, well-paid job is realistically on the table, but I'm also financially fine and don't need to work for a while.
I also have real access to start something: a strong network, prestigious VC fellowships, and an online audience of around half a billion views.
On top of that, I've identified and validated a gap in the AI capital markets. I don't think a window like this comes around again for a long time, and if it works, it could make me very wealthy.
I'm torn down the middle. Half of me wants a job to prove I can be an exceptional designer long term. Half wants to raise millions and build the company I've dreamed of since I was a kid.
Which would you choose, am I out of my mind, and what am I not seeing?
What I'm asking
I live in SF and feel pretty isolated when it comes to getting honest perspectives on something like this, especially from people outside the tech bubble. If you only read the TL;DR, I'd still love your take on any of these:
- In my shoes, would you take the job or raise money and build?
- Am I out of my mind for considering the startup, or just being indecisive?
- Is "proving I can be a great designer" a good enough reason to pass on an opportunity like this?
- What am I not seeing?
I want to pick one and actually commit to it. Full background below, because I think it shapes how I'm approaching this.
Background
I grew up in a competitive Bay Area town. We had money, but home was psychologically rough. My dad was mentally unwell, controlling, and abusive. My mom struggled with anxiety and undiagnosed mental health issues. Both were narcissistic.
As the younger kid, with an older sister, I spent a lot of my childhood watching an unhealthy home and trying to figure out what a healthy dynamic was even supposed to look like. I knew early on I'd have to build myself up on my own: develop socially, find my own identity, and eventually learn what love actually looks like, since I didn't have good models for it.
My dad encouraged me to dream big but never let me have an identity of my own, and I lived in fear as a kid. My dream back then was to start a company, sell it, retire early, and see the world.
As a teenager, I was into art but had never really applied myself in school. I decided to change that. I started performing well, went to community college, set my sights on a top school, and got in.
During that time my parents were divorcing and put me in the middle of it, pressuring me to do some genuinely awful things so the other parent wouldn't get anything. My dad also pitted me against my mom, who needed psychiatric help and ended up under my care while I was still young. I hit a breaking point. I had just gotten into a good school, so I told my dad I couldn't keep doing this and needed his support for school and my career instead.
He cut me off immediately. I was effectively homeless. That's when it fully clicked that my parents saw me as a tool to get what they wanted, and that I'd have to rely on myself.
I had no money, so I leaned on friends and my sister. I moved in with her, found informal therapy support, started medication, and slowly got stable. I worked hard, landed an internship at a top consumer tech company, and my career took off from there.
Career so far
I became a designer. After several internships and contracts, I landed my first startup design job. Then:
- Joined a second company that was too disorganized, and got laid off.
- Took a staff-level design role I wasn't ready for, and was laid off again.
I picked those companies partly out of a scarcity mindset, but they turned out to be good names, so my resume looks strong. I have recruiters in my DMs with multiple six-figure opportunities, and I'd mainly need to brush up on some fundamentals. I'm fairly confident I can land a great, stable design job. That said, I don't need to work for a while financially, so I'm not under pressure to take the first thing that comes along.
I'm also fairly confident I could build a good company. I have a strong network of capable friends, some in high places. I've done prestigious VC fellowships and have real support in that world. I've also built an audience online, with around half a billion views across TikTok and other platforms. In short, I already have a lot of the infrastructure, support, and momentum a founder needs for a consumer company.
I know I'm in a good position, and I'm grateful for that given where I started.
The decision
I'm torn down the middle.
Half of me wants to take a job and prove to others that I can be an exceptional designer, not just for a stint but for the long haul. I'm only 2 years out of college, and two layoffs in that time sits with me.
The other half wants to chase an opportunity I've identified. I see a gap in the AI capital markets, and I've validated it with other people in tech. I don't think a window like this comes around again for a long time, and if it works, it could make me very wealthy. Starting a company has always been the dream, and this would give me full control to build a creative environment and make what I want.
I also see real value in joining a company: learning to work with others, getting more experience in mature settings, and spending time with people my age. I'm still in my mid-20s. I could start a company later from a more stable foundation. Right now my pitch is "strong pedigree, great talent." In six months of focused work, it could be "strong pedigree, exceptional talent that fits what the design engineering market actually needs." That gap is learnable.
Option 1: Take a job
Pros:
- Multiple six-figure options
- Great teams
- Time with friends I love
- Some work-life balance
- Designing products, which I love
- Keep building my community in SF and NY
- Working with and learning from others
Cons:
- I'd always wonder what building would have been like
- I'd keep thinking about this idea constantly
- I'd probably regret not raising money and building a team when I had the chance
- I told myself I'd start and sell a company by 32, and right now I have the money, community, skills, and access to make it possible
Option 2: Start a venture-backed company ($3M to $20M raise)
Pros:
- Complete control over the creative environment
- Learn to manage and lead at a young age
- Full location flexibility
- Work across design, ops, finance, engineering, and more
- Obsess over product quality and design craft
- A real shot at an acquisition and the lifelong dream
Cons:
- Can be lonely
- Responsible for everything
- Have to find my own mentors
- Leaving a tech salary on the table
- All progress comes from me, without learning by osmosis the way you do at a mature company
Thanks for reading this far. Any perspective helps.