One year ago, my dear friend Alex and I were sitting in her backyard, sipping ginger tea, when she asked me to write down “An Ideal Life List.”
The first two things on my list were:
1. Take a solo trip once a year (at least 7 days)
2. Transition from a therapist to an ops role at startups, practice operational skills and take consulting projects with good money (well, after being a therapist, you are just starving)
A year later, I’m proud to say I’ve completed 1 and 2, repeatedly. And I had no idea how far I’d come.
Let's dive into number 2 (will write more about 1 in my next blog):
Over the past year, I graduated from a post-modern (aka, hippie-style, just joking, CIIS is pretty legit) therapy school. I found myself in Silicon Valley, a la-la-land where everyone believes they’re the next Elon if they try hard enough (or loud enough). I often felt like an outsider. I have shared here- how the first crazy startup experience reshaped my identity and worldview. As a result, I don't have much fantasy about startup & VC life.
When I interviewed for startup operations roles after the founders shared their headaches and challenges, I’d open my “crazy notion documents” (as a friend called them) and outline all the projects, saying, “Here’s what we can do right away, here are the steps, and I can add value here, here, and here!”
Nine times out of ten, the founder would look at me and ask, “Gatsby, why this startup? Why us?” (Interpreter: Why me?!) At first, I tried to use their fancy, trendy words to blend into the Silicon Valley vibe. More often than not, both the founder and I would end up laughing because it was hilarious to hear myself use jargon I didn’t really relate to, and sometimes I couldn’t even pronounce it right (facepalm). But hey, at least I was trying.
Rejection, rejection, and more rejections.
I asked my friends J and B for coaching. J told me to sit down with the founders, listen to them like a therapist, figure out the gaps, and create projects to address those gaps, instead of parroting their buzzwords. B helped me organize my notion documents even better and added storylines. I was so prepared, but I felt weird psychologically—my ego was holding me back. Another friend, N, took over and coached me on my psychological barriers by sharing his ridiculous life stories and his philosophy of not giving a F, and laughing at being a human because life sometimes is just ridiculously hard.
Somehow, it started to work.
One day, I was interviewing with the 996th founder when I got a trial offer as the Chief of Staff. Only this founder had no clue where he wanted his company to go. I quickly figured out he didn’t actually need a Chief of Staff but rather a 24/7 therapist (or a mommy).
Of course, I turned down that offer. Thank you, thank you very much.
In another interview, the founder was grilling me—“Gatsby, tell me your passion? Why this industry? Why this company?! You have zero background in this industry. You can’t code.” (But I just hired two AI engineers for you? I know how to run your office in a lean way, help you with your deck for investors, and I can design your GTM right away!) After two weeks of talking and co-working, I turned it down.
In my opinion, what really makes an interview go south for candidates is when the founder feels entitled to gauge how much passion they have for the company—especially if it’s not a C-level position. A good employee is someone who gets things done, not necessarily someone who shares your grand vision. Let’s be real, they’re more concerned about their paycheck, insurance, and maybe even egg-freezing. And honestly, that’s how it should be.
A month later, an old friend (also a founding team member at a phenomenal startup) was catching up with me. We started to talk about the definition of a good investor. This friend is very grounded and hardworking, with a legit resume from years working in big tech to now his own startup. He took a pause and told me: that there are many ways to define a good investor. But in an entrepreneur’s eyes, a good investor should be able to help raise the next round. Period.
This is the type of smart people I like the most—they are knowledgeable and talented, but also not trapped in their head. They gaze at the stars while keeping their feet on the ground.
I showed him my notion document with a GTM plan for their product. I got their interviews. This gave me inspiration—what kind of companies and founders I should talk to and skip those “always-big-dream-and-forever-seed-round” ones.
The interview dynamic improved immediately—in the sense that we are partners working for the same goal with different skill sets. Of course, I’d have an outline of the industry and product, but more importantly, I would highlight my strengths ten times bigger instead of areas I’m not familiar with. And I truly believe you don’t need to be 10/10 to be hired, just as you don’t need to be perfect to be loved. (If after everything I complete for the company the founder is still focusing on why in Silicon Valley I still can’t code, I’d walk away with grace, immediately. It doesn’t mean anyone is bad, it’s just that we aren’t compatible.)
The interview negotiations started to become productive. And I have connected with a handful of down-to-earth founders and teams. (Why did you choose us? Because this is the inevitable future-facing industry, your company is first-tier, your product is sexy enough, and you guys just closed the A round. You guys just need a well-designed GTM plan, and here is what I’m going to do…)
I got two consulting projects with good money by being the authentic me. I mean, what else can I be anyway?
Job hunting is no small task. In addition, this year the economy isn’t the best. But from my own experience, I know it’s possible to transfer industries and find a fit by just being yourself.
Cheers to this Valley! (And a special Thank You to my dear friends)