Transitions

One of my favorite comedies growing up was Trading Places. It was a fascinating story of what happens when you reverse the fortunes of people from rich to poor and poor to rich. The movie also happens to involve the commodity futures business, which was where I started my career.

In the film, the villains of the movie, the two owners of a commodities brokerage firm, make a wager to test whose views on nature vs. nurture were true. They setup one of their employees for theft and drugs, fire him from his job, and freeze his bank accounts. Meanwhile, the owners took in a conman from the streets, installed him in the old job of the employee they setup, and provided him access to housing and wealth. It did not take long for the main characters to adjust into their newfound life situations.

Of course, this was work of fiction and to keep the story going, they had to have the characters settle into their new lifestyles. We have seen plenty of real life situations though of people making radical shifts in a short period of time. Take for example all the crypto bros that all of a sudden became AI gurus. One day it was blockchain everything and the next day it was LLM’s everywhere.

I have gone through plenty of my own large shifts in my life and career over the years. While I started my career in commodities trading, I quickly jumped to software engineering. Years later, I did another huge turnaround from developer to salesperson. Then I launched a startup as a founder, became a community builder, and shifted to developer relations.

All of these changes were challenging. While I had some programming experience growing up and had graduated with an Electrical Engineering degree, I did not know anything about writing production level code. For the first six months, I walked into the office every day thinking I was going to be fired for not learning fast enough. Fortunately, I managed to learn enough to launch an app and not drop any production databases in the process.

I definitely thought I would be out of the job when I got transferred to sales. I knew next to nothing about sales and got zero training or mentorship from my manager. Luckily we sold a technical product to engineering teams, so I muddled through as a sales rep that actually knew the product and could explain things to engineers. Eventually I switched to a company that excelled at enterprise B2B sales and provided me incredible experience to learn the ropes from experienced professionals at the top of their careers.

Each of these stages in my career were hard. I often felt I was an imposter stepping into these roles and had intense doubts about my abilities. Nothing prepared me however for how jarring of a transition it would be from working at a big company to jumping into startup life.

There are two directions you can go between corporates and startups. The easier transition is going to corporates. This is not because it is easier from a cultural adjustment standpoint. That is often the most jarring experience. It is easier because you have more time to onboard and adjust into your role and new company. There are resources, teams, and processes to support you with whatever you need to succeed. Even if the work becomes overwhelming, the company is big enough to provide help, such as peer and mentorship programs to talk through the stress and management processes to mitigate and adjust workloads.

When I arrived at AWS, I joined the startups team that was staffed with formed startup founders and operators. A lot of the folks I talked to in my first few months of onboarding joked that they joined AWS as a vacation from startups. Even though working at Amazon is absolutely not like a vacation, I could understand what they were saying. As crazed and stressful as things might get at a massive company like Amazon, it is nothing compared to the stress of startups.

The much harder transition is from corporate to startup. I recently spoke with another former Amazonian who made the transition to launch a startup three years ago. Though he prepared himself financially and had already started work on his startup, he shared that nothing could truly prepare him for the shock once he left. He spent the first year of his startup just trying to unlearn all of the habits he had picked up while at Amazon.

Though big companies will talk a lot about ownership, you do not truly understand what that means until you are in a startup. As a founder, you quickly realize that there is no one else to do the work. If a problem comes up with a customer, if an operational snafu stalls momentum, if a bug takes down the software, you just got to roll up your sleeves and fix it. And if something does not get done, that’s how it will remain until it is forgotten or blows up into a bigger issue you simply cannot ignore. Even as an employee, the startup does not have the resources or staff to cover you if you cannot do the work.

The other thing you realize is the difference in speed. Corporation life moves, but it can feel like slow motion video when you have been in startups. Building, iterating, testing, experimenting, deploying, learning, and pivoting happen at breakneck speed. Decisions do not wait for the status meeting next week. There are no meetings to coordinate the next meeting. You are not writing a 6-page narrative to propose a new feature. No one cares about the new cover letter on the TPS reports.

Startups are pure execution machines. This is by design as a startup is a hypothesis by founders to find a repeatable and scalable business model. Until they land on that business model, they are essentially on life support. A corporation has a business model that is working and generates profit. Corporations are pure optimization machines, taking what already works and figuring out ways to further expand the business and increase profitability. While speed is not irrelevant, big companies care more about capital utilization.

Returning to my ex-Amazonian startup friend, that is what he meant by unlearning. You have this weening off period where you realize the things that made you successful in your role at a big company are simply not helpful as a founder. There is no time to be right about something or wait for the perfect situation, you just have to continuously iterate and ship.

I am now going into my second corporate to startup transition. The first time was leaving Oracle to launch a startup over fifteen years ago. My biggest mistake then was pretending our little startup was some big company, leading us to waste a lot of time and money. I also assumed that everyone on the team had the same bias for action and level of personal ownership that I did, which ended up not being the case. This is why choosing your co-founders well is so important!

I did not think this second transition would be as hard leaving AWS. It is actually hard in another way that I did not expect. After four and a half years of pouring myself into a role that I loved, I have found it hard to stop being the Global Startup Advocate. Though I had some obligations to finish up towards the end of last year, I still miss that side of who I was.

The other challenge has been getting mentally focused. The reality is that it was an exhausting few years that was compounded by the travel. When I came back from Taiwan for the holidays back in mid-December, there were days when I could do nothing but alternate staring out the window and at my laptop without accomplishing anything. It felt massively unproductive, but I did not have the energy or desire to snap myself out of my zombie state.

Now that I am out of my post-AWS funk, I am shifting into startup focus with renewed energy and excitement. It simply took me some time to realize I needed to clear my mind first. This is something a lot of founders jumping from corporate to startups neglect. Once you get on the startup train, there are precious few moments to stop for a mental and emotional cleansing. If you can afford to, take that time upfront to prepare yourself for the long journey ahead.

Did you make the transition from big corporate to startup founder? What was the most difficult adjustment for you?

MARK BIRCH

I am back in NYC for a couple of weeks before I head back to Taiwan on February 5 after the Lunar New Year. It has been great to catch up with folks from other startup founders to fellow Amazonians. I even attended an impromptu happy hour last night with some of the 42Geeks based in NYC.

Speaking of 42Geeks, the former Chief Geek and startup founder Chok Ooi joined me for an interview on TaiwanPlus, and English-language live streaming and an international television channel based in Taiwan.

The show is called Connected featuring stories of startups and entrepreneurship that are relevant to Taiwan. Over thirty minutes, we discussed Taiwan's startup ecosystem, building startups overseas, and how programs like the Taiwan Gold Card attract international talent.

Check out the interview here on their YouTube and please give it a thumb up!