Jon Nordmark founded eBags.com in 1998 as one of the first Internet e-commerce companies and grew it into the largest online retailer of luggage, bags, and travel accessories. Jon was previously a successful corporate executive who led marketing for Samsonite.

eBags raised $30 million of VC funding in 1999 and survived the dot-com boom and the 2001 bust era, but the crazy growth expectations of VC investors often felt misaligned with the profitable growth path of the company and the market. eBags was eventually acquired by Samsonite in 2017 after selling $1.65 billion worth of products.

Jon's second software company is Iterate.ai, a low-code enterprise innovation platform allowing big companies to integrate, test and scale new technologies quickly and efficiently. The company was initially funded by services revenue and then by software sales. Jon eventually raised $3 million in angel funding and a strategic investment from a large customer.

Iterate.ai has grown to over $10 million in revenue with no salesperson and an $82,000 marketing budget. It is now profitable, with no plan to raise outside funding from big VC or PE investors. This company overcame the recent challenges of the COVID-19 pandemic and emerged stronger.

In this episode, Jon explains:

• How he started and grew eBags.com into one of the largest and the only profitable online retailers in the early 2000s
• The brutally frustrating challenges he faced after raising big VC funding when the company was growing but didn’t meet investors’ extreme expectations
• How he kept returning as CEO of eBags after retiring, then eventually sold the company
• Why he is staying away from big VC funding with his second company, Iterate.ai
• How they approached a strategic investment from their largest customer
• Why it took them 7 years to get to real, scalable product-market fit

Learn more at practicalfounders.com.