On a road trip with their Bernedoodle, Milo, Ellen Diamant, the creative genius, and Michael Diamant, the business guru, decided the dog gear they could buy was not good enough. So they started making their own. That trip became Cleverpup, a New York direct-to-consumer brand selling training and travel essentials for dogs, founded in 2023 [Spa and Beauty Today].
The Diamants are not first-time founders. In 2003 they launched Skip Hop, the design-led baby gear company whose diaper bags ended up in Target, Pottery Barn Kids, and most American baby showers of the late 2000s [Bloomberg, 2011]. They sold a majority stake to a private equity firm in 2013 [The New York Times, 2013], then sold the company outright to Carter's for $140 million in 2017 [WWD, 2017]. Cleverpup is, in effect, the Skip Hop playbook pointed at a different aisle of the pet store.
The bet
Cleverpup's positioning is narrow and deliberate: "innovative dog products for training and travel" with "smart features, durable materials, and timeless style" [Cleverpup website]. The company sells direct through cleverpup.com rather than chasing PetSmart shelf space on day one. That mirrors how Skip Hop began, with a single hero product (the Duo diaper bag) that solved a specific carry problem for new parents, then expanded outward into a full catalog.
The wedge here is design taste applied to a category that has historically been split between cheap commodity gear and luxury fashion collars. The Diamants spent two decades proving they can sit in the middle of that barbell at premium-but-attainable price points. Whether dog owners will pay Skip Hop prices for the dog equivalent of a diaper bag is the entire question Cleverpup is built to answer.
Why it could be big
The US pet industry has expanded almost every year for two decades, and the post-2020 cohort of pandemic puppies is now aging into the years where owners spend most heavily on training tools, travel crates, and replacement gear. Premium DTC pet brands like BarkBox, Wild One, and Fable have shown there is shelf space, online and physical, for design-driven challengers to the legacy incumbents.
Cleverpup also benefits from something most seed-stage consumer brands lack: a founding team that has already built the supply chain, retail relationships, and licensing playbook required to scale a physical-goods company. Skip Hop reached more than 50 countries before the Carter's deal [Bloomberg, 2011]. The Diamants know how to take a product from sketch to a Target endcap. If Cleverpup's first hero SKUs find traction direct-to-consumer, the path into specialty pet retail and mass channels is one the founders have already walked.
Michael Diamant was the featured speaker at the Founder Institute's New York Fall 2024 graduation, billed there as the founder of Skip Hop [Founder Institute]. The signal is modest, but it places him back in the active New York founder ecosystem rather than in post-exit retirement.
The team and traction
Ellen Diamant, the creative genius, co-founded Skip Hop with Michael in the early 2000s and was profiled by The New York Times in 2006 on the strategy of charging premium prices for everyday parenting gear [The New York Times, 2006]. Michael Diamant, the business guru. At Cleverpup, the two are listed as co-founders, with Michelle Rodriguez serving as Director of Ecommerce [The Org].
Headcount is small by design. Third-party trackers list the company at four employees [RocketReach] and in the one-to-ten band [The Org], consistent with a brand still in its first product cycles. Skip Hop itself ran lean for years before scaling, so a tight early team is not out of character for how the Diamants build.
| Metric | Value |
|---|---|
| Skip Hop sale to Carter's (2017) | 140 $M |
| Cleverpup employees (2024) | 4 count |
| Milestone | Year | Source |
|---|---|---|
| Skip Hop founded | 2003 | NYT, 2006 |
| Skip Hop majority stake sold to PE | 2013 | NYT, 2013 |
| Skip Hop acquired by Carter's for $140M | 2017 | WWD, 2017 |
| Cleverpup founded | 2023 | Spa and Beauty Today |
| Michael Diamant headlines FI New York graduation | 2024 | Founder Institute |
The honest counterfactual
The bear case is straightforward: premium DTC pet is crowded, customer acquisition costs on Meta have climbed for every consumer brand since 2021, and a four-person team competing against venture-funded peers like Wild One and Fable will need to be ruthlessly efficient on every dollar of paid spend. Skip Hop's category, baby gear, also had a structural tailwind Cleverpup does not: gift registries that drove zero-CAC customer acquisition at scale.
The bull answer is that the Diamants have done this exact motion before, in a category with similar emotional dynamics, and reached global distribution. They also appear to be self-funding or quietly funded, no priced round has been disclosed [captured sources], which means they are not yet under pressure to grow into a venture-scale outcome before the brand is ready. A lifestyle-business growth profile, paired with founders who know how to license and exit, is a defensible posture in consumer goods.
What to watch
The next twelve months should clarify three things. First, the catalog: does Cleverpup stay focused on training and travel, or does it broaden into beds, bowls, and apparel the way Skip Hop broadened from diaper bags? Second, distribution: a specialty retail partnership, even a small one, would be the clearest signal that the Diamants are running the Skip Hop playbook again. Third, capital: a named seed round with consumer-savvy investors would shift the story from second-act passion project to scalable brand.
For a category as full as premium pet, the question is not whether Cleverpup can ship good product. The Diamants' record makes that the safest assumption in the file. The question is whether dog owners in 2025 will reward design taste at the same premium that new parents did in 2007. What would you pay for a leash that looks like it belongs in your apartment?