Kyle Hensey Chubbies started in 2011 Teamed up with three Stanford friends to create a brand of fun shorts with a weekend and beer vibe.
Irreverent direct-to-consumer clothing brand – one of its popular products is ripped shorts Wearing a Speedo-style swimsuit underneath — “probably objectively a bad idea,” Hensey said, half-joking. Still, the company took off—revenues increased from $1 million to $8 million. While Cupis was still around Acquired by Solo Stove In 2021, it marked a rare exit for retail just as the direct-to-consumer boom was beginning to collapse.
After sitting on the sidelines for a few years, Hency is back: He co-founded Good Day in 2024 with former Chubbies CFO Dave Wardell, and the startup just raised a seed round to solve one of retail’s biggest problems: managing inventory.
Hency has hard-earned first-hand experience in this area. While Chubbies was ultimately successful (Hency said it now does $100 million or more in sales under new ownership), Chubbies nearly ran out of cash three times, and at one point was $2 million cash negative in 18 months. Managing inventory became critical, and Hensey said he had difficulty using the software tools available at the time.
Hensey said that in today’s market, apparel brands face greater pressure to tightly manage and focus on everything below the revenue line.
“Every brand now has to manage revenue down to profit because those profits are the only way they can fund their business,” he said. “Lenders have gone out of business. VCs are no longer backing brands like they once were. If you look up how much VC investment in consumer transactions has decreased since before this period, some numbers show a decrease of over 90%.”
Good Day exclusively told Fortune that the company has raised $7 million in seed funding from existing investors including Ridge Ventures, FirstMark Capital, and Flex Capital. New investors include Long Journey Ventures, Adverb Ventures and Seguin Ventures. This brings the total funding raised by Good Day to $13.5 million, with current clients including Hill House Home, The Normal Brand, Margaux NY and Kenny Flowers.
Amish Jani, co-founder and partner at FirstMark, describes Good Day as “AI-native, ERP-lite”—an enterprise resource planning system that differs from traditional options. He believes there is an opportunity for startups to capitalize on the AI boom as retailers redesign their systems of record for this new era.
“If agency solutions can drive real utility and directly replace labor costs, I expect e-commerce brands to be among the first adopters of these tools,” Jani said via email. “GoodDay is a great example in the ERP space, but you can also see this happening rapidly in every major vertical SaaS category in consumer and beyond.”
While Hensey’s latest venture may look a little more staid than the fancy Chubbies he once whipped, the entrepreneur isn’t completely ditching that attitude. An important part of Good Day’s brand marketing is to mock established ERP competitors such as Netsuite.
“Do you think NetSuite, which was founded 20 years ago by a bunch of guys in suits, was going to be helpful to anyone during Black Friday and Cyber Monday?” Hency said.
Hensey’s comments were not accidental but strategic. He knew he was new to the ERP jungle, but he thought he could convert customers away from established competitor NetSuite. There is some evidence that this may happen. For example, Jimmy Sansone, co-owner of The Normal Brand and Good Day accounts, said via email: “From an operational perspective, we do not have accurate visibility into inventory balances and our operations team must rely on offline spreadsheets and manual tools to move, fulfill, purchase and receive inventory.”
Hensey’s forthrightness is part of his business philosophy.
“I think that’s really important when you’re building a brand that’s different,” he said. “That’s more important than staying calm.”