Letter #1: This Is Not How It Was Supposed to Be

This is not a blog post about how I've shipped my 1,000,000th Shopify order or how I got my website to convert at 7.28% or how that led me to buy my first yacht. This is more about the reality of a majority of startup employees.

Learning yesterday for the fourth time in my career that the equity I received to join a startup in its earliest day is now nearly worthless was hard. While this happens often, what is heart wrenching though is knowing a few select people on the team were able to participate in secondaries that allowed them to sell their equity while the majority of employees whose back the company was built on in the earliest of days, were excluded.

Equity, you say? Tell me how.

While I celebrate all I and the teams I've worked with have accomplished at different stops in my career, nobody talks about the ugly side of equity and how stacked the odds are against positive outcomes for employees even if the company is successful. We often draw a direct line between “successful startup” and “everyone’s rich!!!” but the line isn’t as straight.

I empathize with what founders go through with their sets of challenges and problems as well, all valid, but for the moment I'm going to focus on mine as a startup employee.

As I now sit back and reflect on 13 years of helping build startups, I’m going to be honest and vulnerable for a second with some raw thoughts in the hope that others may take away something positive.

In this moment the first thought that comes to mind is how startup employees including myself often work as hard as possible, work late nights, selflessly putting companies first at the expense of our sleep, health, relationships with friends and most importantly family.

Last week on a call with a friend I joked tragically that my Carta was a graveyard of great visions, hopes and dreams!

I’d always been told “what you put in is what you get out” and today I sit back and look at all that I put in, from launching of successful products, scaling supply chains, shipping products to more than 5000+ doors, working on 100+ SKUs intimately, countless trips to China (probably 25 times or more), helping hire and interview hundreds of people, and the list goes on but today I would be lying if I said it feels like I have something clear cut to show for it. I know it’s not true but it in moments like this it can certainly can feel like it.

Of course, I now have more experience and all that comes with time, but when you lose out an opportunity on life changing outcomes, the emotions make it hard to focus on the wins. “Take risks now, they will pay off in the long run” I would tell my younger self, and in moments like this my motivation is to ensure I make that reality happen because if I don't that saying wouldn't be true. Except the long run is now my present.

I remember the times sitting in conference rooms when a founder was like, “I guess the only option is someone has to go to China tonight” and that someone was me and I had no issues doing it.

Like clockwork, 1 am. 🕐

14 hour Cathay Pacific flight to Hong Kong. ✈️

Land at 5 am. 🕓

2 hour van to Shenzhen, sometimes Dongguan. ✌🏽

20+ hour trip door to door. 🥱

Shower, have breakfast and head to the factory. 🚿

Repeat 25, maybe 30 times. 🔁

Only to often realize the “launch date” requiring me to fly out on a whim was often based on feels 😂

An ex-colleague I just spoke to yesterday called me gutted to hear about the disappointing outcome, “It was chaos, I’m surprised we made it as far as we did. I felt like you were the dad at (censored), guiding and directing the founders to make sure the wheels didn’t fall apart”.

While he was not wrong, I didn’t feel like I was the parent but did sense friction at times when I tried to reel in any behavior I thought could negative impac the company which in the long run could impact the value of all our equity. I do remember in my startup career having to be the adult in the room. Getting out of bed and rushing into the office at 3 am to help with the messy situations alcohol often creates when mixed with young teams. This time after a holiday party just weeks after I was looked at like I had two horns by leadership for saying “not every event should be centered around drinking and alcohol”.

I remember trying to fight for employees who did not have equity, to get equity.

I remember trying to get our team better benefits so that they felt them and their families were cared for while they worked hard everyday.

Today I think about how employees give it their all without realizing that while their hard work is in-fact increasing their probability for a positive outcome, given the obstacles employees face in exercising their options and other factors, they are effectively disproportionately increasing that probability for investors and founders first. Today I’m going to think about how I made amazing friends along the way to help take the edge off.

As an eternal optimist I know I’ll be fine and this is not the only way to look at it, but today I’m allowed to.

Tomorrow? We build.

If you enjoyed reading this letter and want me to send you the next letter, drop me your email here.

Appreciate you✌🏽