CEO Circle with Naman Trivedi, Caroline Caselli, and Randy Paris (#9)

On this episode, Aaron answers questions from three up-and-coming startup CEOs: Naman Trivedi, Caroline Caselli, and Randy Paris regarding:

How to think about strategic opportunities vs. fundraising.How to create psychological safety and engage their teams.How to balance managing people vs. doing the work themselves.

Naman Trivedi founded Wattbuy in August 2017 to help millions of Americans choose cheaper, greener electricity plans and advance the global transition to a clean-energy economy. They raised a $2-million seed round, which enabled the team to identify a solid product-market fit in real estate and energy. They’re now at an inflection point in the company’s history. To continue to grow, they’re wondering whether to capitalize on a strategic opportunity with a partner company or raise a next round of funding. 

Caroline Caselli (@cmcaselli) and her team at Haven Connect are on a mission to get more people into affordable housing. They connect low-income applicants and affordable-housing property managers to get people into units faster. They raised their $2.4 million seed round in 2019 and are scaling the company. Caroline is curious about how to create psychological safety and get buy-in from her team members.

Randy Paris is the CEO of BrewBike, a startup that serves coffee on multiple college campuses in three states via bikes and retail locations. This year they launched an e-commerce shop to serve thousands of online customers. To date, they’ve sold over 100,000 cups of coffee, paid student employees over $150,000 for their work, and raised over $2.5 million in funding. Because of the company’s growth, Randy is interested in managing people even more effectively rather than doing the work himself.

Aaron mentions the following resources:

Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future by Ashlee VanceHigh-Performing Teams Need Psychological Safety. Here’s How to Create It by Laura DelizonnaThe Five Behaviors of a Cohesive Team by Patrick LencioniClockwork: Design Your Business to Run Itself by Mike MichalowiczBlitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies by Reid Hoffman and Chris Yeh