Jeremy Wood’s company, OpenStore, offers founders the option to sell their businesses or have OpenStore operate and run them on their behalf. This innovative approach has not only provided a lifeline for many e-commerce founders but has also positioned OpenStore as a major player in the e-commerce market. Join Wood and Adam O’Donnell as they delve deeper in this episode of Sit Down Startup.

Self-belief is a muscle you can build

The journey from founding a startup to running a successful company can be notoriously rocky, and Wood’s was no exception. “It’s a continual set of low moments mixed in with high ones,” he says. “I think for the first year prior to that massive valuation, you are in this constant state of, ‘Is the world going to be as excited about this as I am? Is this as big a deal as I think it is?’”

One of the most challenging responsibilities for Wood as a founder was to share his vision and win people over. He recalls, “I was constantly having to go out and say, ‘Here is everything I believe to be true.’ That was a muscle I had to build over time. I got better, but there are definitely some low moments where I was like, ‘Oh man, how am I ever going to convince everyone else that this is as important as I think it is? I don’t think I can even properly express it.’ And then over time, I got good at expressing it.”

Wood also had to address doubts about his business’s viability from others. “We believed very strongly: Build the right engine and then start running it. That philosophy meant that OpenStore did not buy its first business for quite some time, causing people to doubt whether the company could succeed. That was kind of a deflating moment where I was like, ‘We will get there!’ And they were like, “Yeah, but you’re not there yet. Isn’t this your whole purpose?’”

Timing is everything

Hard work was crucial for OpenStore’s success, but luck also played a part. Wood’s startup began raising capital during the e-commerce boom that happened due to the COVID-19 pandemic. “The funding environment was super favorable,” Wood says.

Consumers were growing weary of giants in the market, too. “Seven months after we founded the company, Shopify surpassed Amazon in total number of monthly customers,” Wood recalls. “That was a really cool moment of people moving away from these Amazon-like experiences towards more of these narrative-driven e-commerce brands.”

Wood’s own experience has taught him the value of good timing in business. “One key question I ask people when they are fundraising, especially their first round, is: Why now? Why would you build your business now? What changed about the market that this couldn’t have been built 5 or 10 years ago? There are a lot of ideas out there and there are a lot of motivated people. You need to time the market correctly and come in with really motivated people and a strong idea.”

How AI will impact the future of e-commerce marketing

OpenStore currently manages 40 e-commerce companies. Handling multiple businesses emphasizes the need to leverage AI effectively. The use of AI has enabled Wood and his team to extract valuable insights from customer reviews. “It just helps us understand what the community likes about our products because you can’t always read every review. Synthesizing that means we can respond and improve our products.”

Wood is also excited about how AI will change e-commerce marketing. Influencers have pioneered live commerce, but soon, Wood believes that AI will dominate this form of marketing.

“Suddenly, people are able to ask questions and see a product interacted with live. … You’re seeing [the product] moving around and you’re seeing someone’s facial expressions as they interact with it. I think [AI] is also going to open the door towards really strong customization for customers that’s going to allow customized viewings of products so that they can get their questions answered about it in a reliable fashion. That’s something I am really excited for in the future.”