What eBay, Napster, and Banks have in common
4 min read

What eBay, Napster, and Banks have in common

What eBay, Napster, and Banks have in common

Me. And sorry– that was the most clickbaity title I’ve ever published.

I published a post last month about the acqui-hire experience, and as we approached the new year, I wrote a post reflecting on changes that took place in my life in 2019. I often wonder where the line between reflection and ‘too much’ reflection is, and if crossing it prevents you from moving forward. I don’t know the answer to that question but realized I’ve only ever reflected on the recent past. So in this post, I look back much further.

I’ll keep this high level because I’ll touch on it later (and I’ve already written about it here, plus LinkedIn exists). I’ll summarize my experience by saying that I’ve primarily worked as a Product Manager in the “payments” space (mainly from the angle of a consumer credit issuer). Most of my work has focused on customer servicing and acquisition. I also spent some time in mobile advertising. I know I suffer from imposter syndrome, but I’m honest with myself when I say I’m not a credit expert. I’m a generalist. Experience would say that I’m effective at making progress within complex environments (sometimes dysfunctional or chaotic), which is pretty much every org that exists. My job is to drive a team towards a successful outcome regardless of what we’re working on, and I’m able to do it by being the voice of our end customer(s), among other ways.

The rest of this should make more sense with an understanding of what I do for a living.

I decided to write down a ‘random’ assortment of things that I’ve been attracted to over the years to see if they’re actually random. It’s not an exhaustive list… things like airports, hospitals, security, criminal justice, health, reputation & trust, investing, etc. just didn’t fit in well without doubling the length of the post and boring you to death.

Companies (aside from 1 of the blocks):

WealthfrontBettermentPlaidVanguardBond Street Marketplace


I looked at these lists and quickly noticed some commonalities shared amongst many of the entities: Platforms, networks, business, empathy, underdogs…

Some of these books were read a decade ago.
Some of these companies were the hot thing more than two decades ago. Our interests don’t fluctuate much. We are who we are. I was pretty excited when I quickly noticed the strong commonalities. It was becoming clear why my career journey has evolved as it has so far.

Company list w/ Empowering or Platform, Network marking.

Theme: Networks & Platforms
I’ve always been drawn to platforms, especially marketplaces and networks or network enablers. Craigslist, eBay, Visa, Shopify, LivingSocial, Banks, crypto, PayPal…

Then I wondered, why? Was it because size is cool, and platforms are a great way to reach a huge scale? Sure, maybe. They’re also super complex. I think I’m attracted to both of those things. But another theme was apparent, and platforms can help them; the little guys (or gals).

Theme: Empowering the Little Guy/Gal
I’m not sure what it is. Maybe the fact that I was never the best at anything aside from trying hard. Not the best in school or sports. Usually pretty good, but not great. Or maybe it’s not that at all, but because 2 of my 5 signature themes according to Clifton Strengthfinder are: ‘Restorative’ (I like to solve problems) and ‘Responsibility’ (I take psychological ownership for anything I commit to, and whether large or small, and feel emotionally bound to follow it through to completion). Maybe it’s none of those things. Regardless, I love a good come back story or rooting for the underdogs.

I’m pretty amazed when I look back at my career journey so far, with these themes top of mind. I never reflected far back enough to see the bigger picture of how it all connects.

1. I started my career at BillMeLater, a pioneer in online transactional credit. It enabled people to make large(r) purchases online and helped businesses sell more. We were acquired by eBay/PayPal in 2008, many years after my fascination with eBay and PayPal began.
Relevant theme: Networks

2. I then went to Millennial Media where I was on a team that tried to help small budget, local advertisers compete with larger budget, national advertisers.
Relevant theme: Networks, and Empowering the Little Guy/Gal

3. I went back to PayPal for a 2nd stint after Millennial. And PayPal is, well, PayPal. A massively impactful set of service offerings connecting businesses to consumers, consumers to consumers, businesses to businesses and is itself a business connecting to businesses to connect to consumers.
Relevant theme: Networks, and Empowering the Little Guy/Gal

4. Next came Blispay. A seed-stage startup. A dedicated, small team of us hit the ground running starting when it was just an idea. Pre-product/customer(s). Far and away, the most fun few years of my career. Blispay became a network of merchants and consumers, built on top of a network (Visa), and focused on SMBs (small & medium-sized businesses). We helped people buy things and helped small businesses compete with the bigger guys.
Relevant theme: Networks, and Empowering the Little Guy/Gal

Commerce and payments are ultimately at the heart of most companies/services highlighted in this post. The payment space is incredibly complex and is continually evolving.  The more time you spend in it, the less you realize you know (and I don’t think that’s the imposter syndrome speaking). It’s an intellectually stimulating area that can do real good for people, so I’m glad I found myself here.

And after this thought exercise, I don’t think it was just a coincidence.

Further Reading
a16z (especially Jeff Jordan, Boris Wertz, Li Jin) produces a lot of incredible content on Marketplaces & Network Effects.