Thoughts


Pathways
Returning to Plaid -- Evaluating Tech Offers and Pathways
Written: March 5th 2025.
Many people would know me as a low risk person. All my holdings are in index funds with a 50, 30, 20 split between the SP500, Rusell 1000 Growth, and Nasdaq 100. Perhaps, that makes it surprising that I am returning to Plaid, a smaller and thus more risky tech company. I think I made that decision with sound reasoning, and thought sharing it would help others navigate their offers and futures.

Compensation

I have been very fortunate to recieve a strong offer from Plaid. Compensation is an important part of any job - no one can pay rent in feelings, passion, or joy. Plaid has offered me a strong base salary, with a very generious stock grant. While their are current headwinds against fin-tech companies compared to the 2021 boom, and strong tail winds for AI companies, I beleive that the compensation at Plaid remains strong. Furthermore, I am given my stocks at a lower implied valuation than the last round. Current tech stocks are significantly overvalued, and AI companies more so, and I think that Plaid is better poised for growth.

Based on the math, had I returned to Tesla, its stock would need to 10x to match the TC I got with Plaid. Plaid's base is higher than the entire TC I would have been offered at Tesla.

Had I gone to a FAANG, like Google, its stock price would need to double to match my TC or Plaid's valuation would need to be cut by half. Compensation

Plaid is still a scale up, and I am really excited by the internal metrics I am watching. That is not to say we have no challenges.

The Information recently wrote an article where they claim:

Plaid is a victim of circumstance. The fintech startup is working on a secondary share sale, led by mutual fund Franklin Templeton, at a valuation of $5.5 billion or $6 billion, I've learned. That's less than half the $13.4 billion valuation it notched at the height of the zero- interest-rate startup boom in 2021.

Being granted stock at that lower valuation, insulates me from the risk of a lower tender offer raise and positions me to capitalize on growth.

Growth

Plaid positions me better for personal growth. I watched it first hand when I was interning there. They are not shy in promoting engineers that deserve a higher level. If you are willing to grow into the role, Plaid is willing to grant it to you. From my understanding the average time to promotion for a new grad is around 1 to 2 years, but some hit L4 in 10 months.

When I spoke to Zach last year during breakfest and questions, one thing we both strongly agreed on is the strength of talent at Plaid. As a rough approximation, the top four schools our engineers come from are: U.C. Berkeley, Stanford, Massachusetts Institute of Technology, and Carnegie Mellon. Not only that, but as I wrote in a blog post for Plaid:

However, of my four internships, I found my team members at Plaid to have been both the smartest and most inclined to help.

And, I seriously beleive that. I'll touch on that in the culture section.

Culture

The culture at Plaid is incredibly unique and I cannot wait to return. I still remember the gestures of kindness I experienced. Some examples (using initails to protect privacy):

WT: Bought me very nice Japanese Whiskey, Sake, and upgraded my plane ticket home back to UCLA. Kept me company when I was alone in New York, responded to slack messages all the time because he knew I needed someone.

TW: Took me to the strand bookstore. When I was stuck on a techincal challenge, he hopped onto a Google Meet and we worked throught it. Similar to WT, he responded to slack messages all the time because he knew I needed someone.

HZ: The best manager I ever had! He cared about my career growth and personal life, included me in the team onsite despite not having the allocated budget from Plaid to do so. Plaid has a reputation of having amazing ICs, but less strong managers. It is my luck to get what is considered one of the best leaders at Plaid. This is probably because he never stopped really being an IC. Despite leading one of the largest teams at Plaid, he still asked me technical questions and helped me with my technical challenges.

HS: Despite being a high level manager, he always had time to talk (and play ping pong with me!).He is also considered one of the best managers at Plaid. He helped me understand the business side of Plaid, and was always willing to help me with my career growth. He visited me at UCLA. Most of all, he bought me a small protien powder keychain that he also had.

EL: One of the strongest tech leads (or I think software architects I have met). Invited me over to his appartment for dinner. Willing to help me with any technical challenge I had. When I left Plaid, he gifted me two books: "The Mythical Man Month" and "The Phoenix Project" where he wrote, "read this and you'll quickly ascend to E8 -- this book is the I-ching of software eng."

MW: Certaintly the coolest engineer I have met - I love that he let me rev his motorcycle! We talked a lot about my personal problems and he taught me how to get fit. I loved that our 1 on 1s were at the gym. Best stock picker as well.

Not Blind Loyalty

While there are many upsides for Plaid, I am not naive and I am not blindly loyal to the company. The most likely reason I leave would be if there is a doom-spiral. Falling growth, leading to falling morale, leading to a lower valuation, leading to our best engineers and leaders leaving, leading to falling growth.


Quotes


Cacophony
“Music and silence—how I detest them both! … No inch of infernal space or time has been surrendered to those abominable forces; all has been occupied by Noise—grand, exultant, ruthless, virile… Noise which shields us from silly qualms, despairing scruples, impossible desires. We will make the whole universe a noise… The melodies and silences of Heaven will be shouted down. But we are not yet loud enough.”

-- C.S. Lewis, The Screwtape Letters

One of my biggest concerns has been the proliferation of noise in my life, and its effect on my attention span and ability to perform deep work. How addicted are we to constant distractions? How difficult do we find reading long pieces of text? I think podcasts are a good example of this. I started to get into it when I was in high school -- starting with Hello Internet as a way to entertain myself while walking or doing mindless tasks. But, how soon that became a constant habit. I subvocalize, so I need to listen to my own internal monologue to think. I realized that if I kept letting other voices into my head, I could not hear my own.

HK
"To the parade commander, the 41-year-old Lieutenant Commander Alasdair Loudon, falls the task of giving the last command on parade to British troops in Hong Kong ... a slow march into a new order"

-- BBC, Hong Kong Handover

Modern empires aren't built with tanks -- they're financed by banks.


Mentors

A lot of my success is because of the many great mentors that have helped me be a better man, software engineering, and learner. I wanted to honor them here (using initials to protect privacy):

At Plaid: HZ, HS, EL, MW, TW, WT
From UCLA: KY, ET, CC
From Others Places: AY