Hello hello and welcome to this week’s tea-time Tuesday! I’m a few days behind this time (traveling a lot for work, attending a lot of events, and very much in do-mode with all the life changes…more on that later).

As I write today’s newsletter, I’m sipping on an earthy, almost-grassy flavor Japanese green tea called sencha. To my surprise, it smelled just like matcha but tasted a bit bitter in comparison but it does get better with more brews. The brewing temperature of sencha is 175°F and it’ll come out a very beautiful light green as you pour this into your tea-cup.

This bitter tasting tea brings me to write about a slightly bitter time in my career journey: the quest to break into the startup world.

🫖 Backstory

My entire career had consisted of the perfect ‘corporate’ background. A big 10 school, an engineering degree, all internships at Fortune 500 companies, and moving to the Bay for a great corporate tech job starting with a best in the class training program.

Yeah, no, I wasn’t kidding when I said I fit into the corporate image…

The challenge was this: I was HIGHLY interested in the startup space. I was fascinated with founders, building a business, and seeing an idea come to life. The entire concept of founding a company impressed the hell out of me.

To the point where I remember never wanting to wash my hands when I met my first ever founder/ceo in real life. I was starstruck. This was the life of a silicon valley corporate employee. I cared 0 about movie stars or song artists - I just wanted to meet more founders and CEOs.

To be honest, I think it’s because deep down I know I want to have my own company at some point. My desire to leave an impact on the world is stronger than any other feeling I’ve ever had. There’s way too many problems that still exist and instead of sitting on the sidelines, my dream is to help alleviate them.

But alas, I had major anxiety, mostly because of two things: my fear of failure and my imposter syndrome. I could’ve given up here, I really could’ve. Life would’ve been so much easier.

Instead, I thought to myself: “I only feel this way because I don’t know how. I just need to learn.” and decided to join a start-up to learn the skills I needed to start my own company.

🔑 Narrowing it Down

When I was in corporate, the golden cufflinks were TIGHT on me. I was working a job I LOVED with people I adored and with flexibility I desired. The only downside? I wasn’t learning what I wanted…. I had reached an upper limit on my learning 😕 and at 24 years of age too.

That didn’t sit well with me.

For a few weeks, I did go on job boards and LinkedIn to apply for roles. I didn’t even know what roles I wanted. I just kept uploading my resume and clicking ‘submit’. Anyone wanna guess what happened next??

rejection. and……………………………. another rejection………………..and another……………

ouch. my days were filled with these emails. I could’ve given up again. But I didn’t. I realized I just needed to learn more - this is different than what I’m used to.

The next several months, I spent time learning more about startups:

• What does it mean to fundraise? How do you go ask VCs for money?

• What does Series A mean? B? C?.. how many rounds are there even?

• How do they grant company shares for employees? And founders? And investors?

• Who do they hire for leadership positions? How do you grow within a startup?

• What kind of roles are the most important for them? Who are their first, second, and third hires?

• Do they keep track of money spent? And their runway? What’s a good runway amount?

• How do they know if they’ve reached product-market fit?

• What if it fails? Do the founders have a back-up plan?

• and the list goes on…..

How did I learn these things? Well, some by googling, some by asking a few friends in the startup world, and to be fully honest, mostly by reaching out to founders online, connecting with them, and asking about their specific use case.

That’s right: I was slowly building my startup network. I was HUNGRY to learn.

Here’s when things became fun: through my questions, these founders realized my value - noticed that other people (their own employees) aren’t asking these questions. They realized I had more to offer and I was able to help them think differently. 😲 😀 

They wanted to work with me and I was ready to try!

The problem was this: my corporate brain didn’t understand or realize the role/job description. I was so used to structure (LOL).

But then I realized, the whole point of me learning & working with startups was to do everything. Basically be a mini-ceo and help run the company. That’s when I realized the job description of a Chief of Staff is what I wanted.

🔑 Getting the Job

So I became super specific about my goal: I wanted to become a Chief of Staff for a Series A, B, or C Fintech or Proptech company. I had my role, industry, and size of company in mind. Again, it was aligned on what exactly I wanted to learn.

Here are the 3 different ways I took to land 3 Chief of Staff jobs:

1. Cold Emailing the Founder

   This is the story of my very first CoS gig. A friend of mine had just told me about this amazing tool she uses to manage her short term rental. As a new Airbnb owner, I was fascinated by this app and wanted to learn more. I went on the website, learned more, lowkey stalked the founder on LinkedIn and on the websites ‘about’ page. After digging deeper, I found a way to schedule a call with the founder/ceo.

   Without thinking further, I booked a call for the next week, prepped a list of questions, and had my first call with the founder. He was impressed by my questions/skills and the 30-minute call ended up lasting an hour.

   We scheduled a second call, where I proposed being a CoS for him and the company. He agreed, sent over a contract, and that was that 🙂 

2. Leveraging my Network

   My second offer/work came from a friend I’d made during my conversations when I was trying to learn more about startups in the first place. Months after our first call, a friend of mine reached out sharing the fact that she knew someone looking for a CoS and would be happy to connect us.

   I reached out to the founder/ceo, set up a coffee chat in person, and soon figured out a start date that works for the both of us.

3. Showcasing my skills on LI and being reached out to directly

   Lastly, I tailored my resume and LinkedIn to showcase more skills than were first presented from my big corporate jobs. I started connecting with founders online. Soon enough, a founder reached out to me directly sharing that he’s looking to hire a CoS. We hopped on a call, had a discussion with his HR person, and shortly got the offer!

💡 Significance

There’s a few learnings that come out of my story:

First and foremost, having highly specific goals helps you get things faster. The clearer you are, the better it is. It’s easy for your friends/family/network to identify exactly what you’re looking for too.

Secondly, knowing when and how to pivot is important. I very very quickly found out that cold applying to jobs was NOT working. So I pivoted. I quickly realized my network didn’t consist of startup folks so I built those connections up. Know when and how to pivot! (as always, let me know if I can help you here)

Lastly, understanding your why for doing something. My why was to learn how to run your own company. Because I knew the reasoning, I spent countless hours on that goal. It wasn’t just about a job or the salary - it was about learning and growing out my skills. At times of rejections, I came back to my why to find other ways I could learn.

📝 Closing Notes

It was a long one this time but I really hope it sparks even a little something for you. Startups are a fully different beast than corporates. Both extremely challenging in their own ways. If you’re ever considering a switch between the two, let me know how I can help!!