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Product Discovery Leader Andrew Chapin on What’s Next in E-Commerce

Andrew Chapin is a product discovery specialist and tech writer with a long history of operating at the intersection of e-commerce and media. Chapin is most known for his work as a pioneer in shoppable media with his adtech startup Benja, which failed under the weight of an accounting scandal in 2020, and his strong track record assisting early-stage tech companies find their product-market fit.

What is Andrew Chapin up to these days?

I’m doing what I love: working with pre-revenue tech startups, helping illuminate the path to their first millions in revenue. I’m fortunate to have a diverse set of challenges in front of me at the moment – it keeps things fresh.

I’ve also enjoyed writing about tech and business, something that I do in many different places. I try to link to everything from my personal blog but it can be difficult to keep up.

And I’ve started talking to incubators and venture firms about my experience as a failed founder. I think they’re finding value in hearing how things went wrong for me, and I’m certainly finding meaning in those conversations.

You’ve long operated at the intersection of e-commerce and media: what trends do you have an eye on?

There are many reasons to be optimistic about the direction and energy in e-commerce, it’s an exciting time. The recent layoffs at Amazon, Google, Microsoft, and Meta means there has been a ton of talent pushed to entrepreneurship. These are brilliant folks who were involved in social and e-commerce, suddenly available to pursue that thing their companies wouldn’t build.

I’ve had a bunch of conversations with people who are building such ambitious projects, and they left me saying “wow.” 

This is especially the case with product discoverability. We reached a point six or seven years ago where online marketplaces became inundated with low-quality, Alibaba white label so-called “direct to consumer brands.” That has been a race to the bottom as they compete on price – but the sheer volume of “new” products made discoverability harder. So much noise.

While those brands focused on long-tail keywords and searched for their winning micro-niche, others focused on shoppable media which has struggled to find its footing because of failures by the major players in social. The shoppable media user experience on Instagram and others is just terrible.

In other words, it’s been a tough path for product discoverability the last few years and while I know everyone is talking about the ways in which artificial intelligence will impact business, there is none greater – in my book – than in marketing, both paid and organic. I’ve talked about reaching people where they live and spend time online for years, but it was surface-level. The level of direct engagement that is about to be enabled via AI marketing tools was totally unthinkable five years ago. Direct-to-consumer brands who embrace these tools are going to really feel the benefit. 

You mentioned the struggles of shoppable media, which is an area where your company was a pioneer in 2014. What did you learn from the failure of your adtech startup in 2020?

How many pixels can we use for this question? I could go for days on this one. It’s impossible to share it all.

From where I stand today, the company failed because I failed to build a healthy communication environment. I failed to communicate with stakeholders and employees as an individual and I also stood in the way of open, honest, direct communication amongst the team. When the company started to struggle in year four, no one knew how to talk about it and I isolated myself, thinking that rolling up my sleeves and showing strength was the only way through it. I clearly should have been more collaborative and invited people like investors to the table rather than being afraid to disappoint them. The worst part is not the one-off act of isolating when it gets tough but how it can snowball: once you start down that path, it’s very hard to walk it back. Had I been a better communicator, the company wouldn’t have imploded like that and even if it failed, it would have been a far better outcome for everyone. A painful lesson learned.

On a personal note, the whole experience pushed me to be more deliberate, intentional, and mindful in my life. The sudden collapse of the company directly hurt a lot of people which is something I didn’t understand until it happened. The depth of my remorse is difficult to put into words so I’ve focused on putting it into action. There’s a quote I think of daily: “When something bad happens, you have three choices. You can either let it define you, let it destroy you, or let it strengthen you.” With the help of friends and family, I’ve been able to take the experience and figure out how to leverage it for good going forward. That’s my north star.

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