A thread on Career Choices

I posted the above thread on Twitter and figured I’d cross-post here:

1/ I’ve been working as a Product Manager for a decade now. The word ‘decade’ makes it sound like a long time. It doesn’t feel like it, but it’s a good time for some reflection.

2/ I started as an intern at a company called Bill Me Later in 2007. BML was a pioneer in the online transactional credit space… they kind of paved the way for the Blispays, Affirms, Breads, of the world.

They got bought by eBay/PayPal in 2008 for almost $1 Billion.

3/ Interviewing for this job was wildly uncomfortable. I didn’t know anything about anything & was bored w/ school, so I put myself out there.

These years were extremely formative. I was exposed to an entirely new world. Product, marketing, e-commerce, acquisition processes, etc.

4/ I think BML was ~300 people when I joined… a solid ‘medium’ sized company. Considered a ‘startup’ but clearly had product-market fit. Very experienced founding team. They bucked all startup stereotypes I had at the time. And PayPal was 10k+ people.

Looking back, what an incredible first job.

5/ I left in 2011 to join the leading independent mobile advertising company at the time, Millennial Media. Founded in 2007, around the time of the iPhone launch. Major competitors were Googles AdMob & Apples Quattro Wireless (iAd).

6/ I think I joined around employee # 130sh & left 2 years later after more than doubling in headcount, and going through an IPO in 2012. Another company with clear product-market fit, and really focused on fast growth.

7/ I left a comfortable job w/ PayPal to join MM because mobile advertising was hot, they were a market leader, it was walking distance to my house & mainly because I wanted to see if I could be effective in a new environment.

8/ Looking back, I’m super happy with my decision to leave a comfortable place for a new experience. Learned a ton about product development in fast growth environments, and gained access to a host of new disciplines that I wasn’t exposed to previously (sales, account management, etc.).

9/ While happy with my rate of growth, I learned that I didn’t enjoy working on things that I didn’t find interesting or relatable. Advertising networks is one of them.

Fortunately, PayPal recruited me back to work on a super high profile initiative.

10/ Going back to PP wasn’t something I thought I’d do again. But I was excited to work in a completely new environment. My first stint at PP was really just a resume + (I was just working on BML).

This time, I’d own a distributed team within a monstrous international project.

11/ The project included hundreds of people, involved building for 3 countries, and had relatively tight deadlines. It was also largely being driven by a PMO w/ a sea of ‘agile consultants.’ Tons of daily frustrations. Tough environment but rewarding. So many big company lessons!

12/ I cannot stress enough how valuable it can be to spend time in a large company. For certain types of people, it can be really difficult. But you learn a lot. And those lessons will apply to every work environment you end up in, not just at other large companies.

13/ Onto Blispay after ~2yrs at PP. I joined on day 0 w/ a small group of ppl I worked with at BML/PP & some I brought from MM. Dream team. When joining a pre-product startup, u have to analyze the risk. I determined the risk was as low as it could get for this stage. No brainer.

14/ My risk framework (applicable to any job) is probably pretty similar to that of some investors:

• Career Risk
• Market Risk
• Technical Risk
• Execution/Operational Risk

(any others I should be including going forward?)

15/ Most people aren’t ever presented with an opportunity to join a day 0 startup, with a relatively low risk profile. I’ll probably never experience this again.

Incredible experience.

I have no regrets as far as joining and working here for the past 4 years.

16/ One of the biggest lessons (more-so confirmations) was that I wouldn’t have been nearly as effective or productive without my prior experience across numerous industries & co. sizes.

It’s confirmation that every learning opportunity is valuable.

17/ If you want to join a startup one day in any capacity (product, sales, engineering, marketing, etc.), know that big company experience can help you later on in smaller environments.

For most roles & levels, we don’t need to be pigeon holed as a ‘startup’ or ‘big co’ person.

18/ I’m a big fan of mantras & quotes. Here’s 1 thats always helped me make career decisions:

“All life is an experiment. The more experiments you make the better.” Ralph Waldo Emerson

Gain experiences in various size companies, industries, etc. Embrace change & keep learning.