Andrew Chapin

Andrew J. Chapin is a tech entrepreneur and writer who says he focuses on the intersection of commerce and media. To say that’s where his focus is doesn’t quite do it justice – commerce and media is where Chapin works, plays, eats, breathes, and sleeps. He lives there.

Chapin has had a wide range of startup experiences. He was an early hire at a startup acquired by Apple, the founding business director at what became the largest independent sports brand in the United States, and was the first business hire at a company which is considered to be one of the most successful startups in the southeastern United States.

And he’s experienced the lowest-lows of entrepreneurship. In 2020, the adtech company he founded and operated for six years filed for bankruptcy, culminating in his conviction for securities fraud.

Humbled and armed with a subsequent “fundamental shift in perspective,” Chapin is doing what he loves: helping startups achieve their first millions in revenue while he produces niche commerce and media properties, emphasizing product discoverability which he says “is paramount, especially with recent shifts in social media, search, and AI.” In his words, Commerce Media Studio is focused on “the fun stuff.”

What is your typical day, and how do you make it productive?

I’ll have to let you know when I experience once of these “typical days.” There are a lot of different projects going, each at its own stage with its own demands for energy. I love handling something different each day.

How do you bring ideas to life?

I chase problems, especially the little ones that pop up when something is a little too clunky or it’s difficult to find what you’re looking for. I’ll stand up a Minimum Viable Product as quickly as possible. If there’s something there, the internet will usually let you know right away. If not, I move on.

It’s important to remember Steve Blank’s definition of a startup, especially during the ideation stage when you’re churning through Minimum Viable Products: a startup is a “temporary organization designed to search for a repeatable and scalable business model.” Startup efforts are ephemeral in their nature.

What’s one trend that excites you?

My primary focus has been on discoverability – information, products, everything digital – and the tectonic shifts that are happening right now are both terrifying and thrilling. Google announced it would experiment with replacing the “above the fold” search results with an AI-based experience. Social media platforms are crumbling before our eyes and people increasingly seem to be allocating their social media minutes with niche digital communities.

All of these ways in which we previously discovered content – search, social – are shifting in a fundamental way. I’m excited to see how all of this works out.

What is one habit that helps you be productive?

Meditation. It took me a long time to get to a place where I was able to feel the benefits but once I got there, I quickly learned there’s nothing better than the centering that comes from a good meditation.

What advice would you give your younger self?

Learn to fail. This is one I learned the hard way. It’s difficult to find the words to convey how it felt to stand in front of a judge and hear her say, “It seems like you just didn’t know how to fail.”

She was right. When I was faced with the prospect of failure, my response was to inflate revenues at my adtech startup and that landed me where I belonged: with a conviction for securities fraud. That was a much more painful failure, impacting many more people than it needed to.

American entrepreneurship culture celebrates “never giving up,” “winning at all costs,” and a sort-of violent tenacity in pursuit of a business but there is a serious downside to that kind of approach. It needs to be said that it’s okay to fail and that it’s far better to fail fast and move on. Don’t get married to an outcome in your mind.

Tell us something you believe almost nobody agrees with you.

Physical media is on the way back.

What is the one thing you repeatedly do and recommend everyone else do?

Challenge every belief and ask yourself “why” at every turn. If you’re able to be objective and honest with yourself, you’ll uncover valuable insights.

When you feel overwhelmed or unfocused, what do you do?

If meditation or going for a walk aren’t doing the trick, I find myself with a pad of paper hashing out all of the things that I need to get done, and then I schedule out my day (or next few days) to the minute. If I don’t get the task done in the allotted time, I move on to the next thing.

What is one strategy that has helped you grow your business or advance in your career?

People spend too much time focused on being transactional with their energy – I’ve found there’s nothing better than just being helpful for the sake of being helpful. If you put that good, helpful energy out into the universe, it will come back to you.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

I made false representations on financial documents when securing a line of credit for my adtech startup and was convicted of fraud as a result. This was an incredible failure in both my professional and personal life, with far-reaching implications – it brought suffering for so many people which I deeply regret.

What I’ve come to learn is suffering ceases to be suffering when it finds a purpose. I know what purpose this failure served for me personally, and I’m working to make sure I make good use of these lessons to do good.

What is one business idea you’re willing to give away to our readers?

Social media is splintering: people who are into politics are retreating into their own knockoff-Twitter platforms, gamers are heading to theirs, media people seem to have congregated in one of their own. Think about these niche communities and who isn’t being served with an option. It won’t be the next Twitter or Facebook but there’s certainly a viable business there.

What is one piece of software that helps you be productive? How do you use it?

Notion. It took awhile to really understand the value but it’s become the best way to keep projects organized and do my writing. I spend most of my day with Notion open.

What is the best $100 you recently spent?

After years of ducking and bobbing and weaving paywalls, I finally paid up for my favorite news websites. I used to think that I’d get the news one way or another and that I didn’t need to pay, but there’s something undeniably valuable about having something you can count on especially in the disinformation environment we live in today.

Do you have a favorite book or podcast from which you’ve received much value?

The Second Mountain by David Brooks has been a life-changer, especially right after my startup failed. I don’t feel I can do it justice unpacking the “why,” but let’s just say it’s the perfect book for people seeking to make a change and live with more meaning and purpose.

What’s a movie or series you recently enjoyed and why?

As a business nerd, I am loving the recent trend where businesses are at the center of such great shows and movies – Air, The Dropout, Tetris, BlackBerry, Super Pumped, and others. There is so much to learn from each of these and they’ve been so well-made.

Key learnings:

• It’s absolutely critical to be objective and honest with yourself.
• Don’t be afraid to fail and fail fast. The alternatives can be much worse.
• When working through failure, remember suffering ceases to be suffering when it finds a purpose.
• Steve Blank said a startup is a “temporary organization designed to search for a repeatable and scalable business model.” Startups are ephemeral in their very nature.