Viewpoints

On Big Ideas, Serial Entrepreneurs & Marathons


April 20, 2016 – Navin Chaddha Shares Learnings from Serial Entrepreneurs Jake/Brighter & Manish/Poshmark

Today, Jake Winebaum, founder & CEO of Brighter, a Saas-enabled dental marketplace, announced a $21 million financing round.  This follows last week’s news of a $25 million financing round announced by Manish Chandra of Poshmark, a mobile fashion marketplace. The ability of these two companies to raise healthy amounts of capital and attract best-in-class investors (General Catalyst & GGV Capital respectively) got me thinking about the learnings from championing Jake and Manish over the last 5+ years.

  • Big ideas inspire: As CEO of Disney.com and co-founder of Internet incubator eCompanies and CEO of Business.com, Jake made his mark as an entrepreneur and executive in the late 90s to mid 2000s.  We invested in Brighter in April 2010, and in our conversations leading up to that, Jake knew he wanted to disrupt healthcare. He very quickly focused on the dental space and vowed to build a platform that delivered price transparency and great service to over 100 million consumers. Today, Brighter is the choice of major insurers and employers and the saving grace for millions of consumers.  For Manish, leading up to our investment in February 2011, the big idea was to leverage his learnings from his first company (Kaboodle) to build the first online fashion brand which put mobile & social in the center of the user experience. Today there are over 1.5 million sellers who curate over 3M items a day; Poshmark sellers upload inventory which is the equivalent of a Nordstrom store every 2-3 days; top influencers have 2 million or more followers; and the average user spend 20-25 minutes a day in the app, opening it 7-9 times daily.    I believe that their success has a lot to do with the truly big ideas that Jake and Manish laid out at the inception of their companies.
  • Serial entrepreneurs execute: Both Jake and Manish have been through lots of hard learnings over the last 5+ years – Brighter’s business model pivot from consumer marketplace to Saas platform, Poshmark hitting wall (shipping) after wall (payments) in its quest to create a simplified and seamless mobile selling platform that anyone could use – but they have never wavered from their original mission.  As a former entrepreneur who was the founder of 3 companies in the mid 1990s to early 2000s, with experiences of early success as well as challenges, I believe that there is no better measure of character than grit. Focus and methodical execution day-after-day is hard and often unsexy, but people with those traits succeed in attracting and inspiring world-class talent which is key to scaling companies beyond founding teams.  Jake and Manish have surrounded themselves with excellence and it has been exciting to watch them grow into elite founder CEOs.
  • It’s a marathon, not a sprint: If you ask Jake or Manish, they will say they are still in the early stages of delivering on their promise, and that they are invigorated by their new investors and capital to move even faster. For Brighter, the next phase is to recruit enterprise software engineering talent to expand the product, while Poshmark has ambitious plans to further extend its reach into the retail industry and expand into new categories and geographies.  I’m thrilled to be on the front lines of these marathons and am confident that these two races will deliver on that exciting finish that every entrepreneur dreams about.