Inspired with Alexa von Tobel

In 2011, as the rise of digital media cast doubt on the survival of print, Sarah Harrelson broke from convention and launched her own independent magazine: CULTURED. Sarah set out to spotlight artists, writers, curators, and designers overlooked by mainstream outlets and has since become one of the most trusted voices in the world of art and design. Beyond the magazine’s editorial prestige, CULTURED collaborates with leading fashion houses, luxury brands, and galleries. Sarah has had a decades-long career in magazines, beginning with an internship at Elle and including launching the Miami Herald’s Home and Design section, becoming the editor-in-chief of Ocean Drive and Art Basel Magazine, and ultimately founding her own publishing company. In this episode, Sarah shares how intuition shapes her approach to talent discovery, why her belief in the staying power of print remains unchanged, and how the magazine’s strategic focus has evolved to span global markets and adjacent industries.  

In 2013, when Ryan Petersen launched Flexport, he approached the problem from a customer’s perspective. Early in his career, he had worked at his brother’s import-export business, sourcing and selling ATVs, scooters, and dirt bikes from Asia to markets around the world. They built the entire technical platform to facilitate these transactions, and Ryan saw an opportunity to make the freight forwarding industry more efficient. He founded Flexport to make global trade easy and accessible for everyone and has since raised $2.3 billion to fuel the business. Today, Flexport’s platform coordinates logistics from factory floor to customer door, serving companies of all sizes. In 2023 alone, Flexport’s technology moved over $32 billion worth of merchandise. Ryan discusses how he leverages the U.S. Air Force’s OODA (Observe, Orient, Decide, Act) strategy, how AI is helping automate 1% of its freight forwarding workflows each week, and why Flexport’s agility remains the company’s greatest strength.

When Eliot Horowitz, Founder and CEO of Viam, was locked down with his family during COVID, he did what any engineer might do—he built a robot to play chess. Once that project was complete, he turned his attention to his ever-problematic sprinkler system. After that? He added smart software to his HVAC system. Through this series of home improvements, he uncovered a problem he was eager to solve, and his third startup was born. Eliot founded Viam to build a product that connects hardware to software and unlocks AI, automation, and data for the physical world. A career software developer and technology leader, Eliot previously co-founded MongoDB, writing the core code base for the pioneering database and leading the engineering teams for 13 years as CTO. MongoDB went public in 2017 and has a market cap of over $20 billion. Eliot shares why he enforces a no-jerk policy when it comes to hiring, how he evolved as a founder from the seed stage to post-IPO, and why he believes that being the product’s biggest user is essential to success.

In 2007, Emmett co-founded a live streaming service called Justin.tv along with his childhood friend and neighbor, Justin. That first entrepreneurial spark grew into Twitch, an interactive livestreaming service that spans gaming, entertainment, sports, music, and more. Today, at any given moment, more than 2.5 million people globally are engaging with Twitch. While Twitch was acquired by Amazon in 2014 for nearly $1 billion, Emmett has stayed on as CEO and continued to scale. Emmett shares why the company's hardest engineering challenge was scaling live video, why the future of the creator economy is "micro-patronage," and the role Twitch plays in combating loneliness. 

Original airdate: Aug 2022

From the time she was a child in East London, Emma Grede knew she wanted to work in fashion. After a long career at the intersection of fashion and entertainment, Emma now sits at the helm of Good American, the fashion label she co-founded with Khloe Kardashian in 2016. The first fully inclusive fashion brand kicked off with the largest denim launch in history, bringing in $1M on day one, and has evolved to include ready-to-wear, swim, shoes and activewear. Emma shares what it was like to experience the roller coaster of launch day, why the ability to understand what customers want is a superpower, and why she thinks in-person retail experiences will be here for decades to come.

Original Air Date 06-02-2021

Most startups set out to tackle massive problems, but working to develop a low-cost, long-duration energy storage solution that will enable the electric system to be 100% renewably powered? That's a big one by any standard. At Form Energy, Mateo Jaramillo and his co-founders are working to bring that very vision to life, leveraging the smartest minds in the energy storage space. Mateo shares why he bet his career on the climate tech industry after attending Yale Divinity School, how his time at Tesla taught him the importance of top-quality talent, and what it was like to step into the shoes of a founder at age 40.

Original Air Date: 12-16-2020

After a career spent inside a hospital, Brian Whorley envisioned a future for American healthcare that, to him, seemed not just possible but inevitable. Witnessing firsthand the growing number of patients burdened by high deductibles, Brian understood that when people have better financial tools to afford care, they seek treatment sooner, leading to improved health outcomes. In 2018, Brian co-founded Paytient, the company that empowers people to pay for care over time with no interest and no fees—ever. Fast forward seven years, and his vision is becoming a reality. Starting in 2025, every single Part D health plan in the U.S. will be required to offer plan members the option to spread their out-of-pocket pharmaceutical costs over time with interest-free monthly payments. Given this new regulation, Paytient is expected to help nearly 25 million Americans more easily access and afford care next year. Brian shares why he believes founders are forged as children, how he built a business among a sea of skeptics, and why he thinks that healthcare entrepreneurs have to partner with America’s existing health system stakeholders to implement the most impactful change.

Growing up, Annie Lamont was an avid reader with an insatiable thirst for knowledge. This led her to attend Stanford—which coincided with Silicon Valley's tech boom and ignited her passion for entrepreneurship. Immediately, she found herself gravitating towards healthcare investing because of the incredible impact it can have on communities. Today, Annie is the cofounder of Oak HC/FT and is recognized as one of the most influential investors in healthcare and fintech. With over $5 billion in assets under management, she boasts an impressive track record, having backed iconic companies like One Medical, athenahealth, and Devoted Health. To date, she has successfully exited more than 70 companies and achieved 15 IPOs. In addition to her venture career, she also serves as the First Lady of Connecticut. Annie shares her take on how generative AI will impact healthcare and fintech, why she believes the smartest rule in venture is to never compromise on integrity, and how she distinguishes ordinary entrepreneurs from exceptional ones.

What if businesses were empowered to consistently attract and hire the best-possible candidates—every single time? In 2012, Daniel Chait set out on a mission to help every company become great at hiring. He launched Greenhouse and scaled the business into the leader in hiring software. Almost a decade later, private equity leader TPG acquired a majority stake in the company in a $500M deal. Daniel shares how leadership’s involvement in hiring sets the tone for the success of a businesses’ recruitment and retention practices, why he believes that magical interview questions are a myth, and how AI is actually making life much harder for both applicants and employers.

When serial entrepreneur Bill Smith relocated his family across the country to build his third startup, the seedling of an idea for his next startup was born. In 2019, Bill founded Landing, the first membership-based leasing model for flexible living. He has since scaled the business to cities around the country with a network of thousands of apartments. Along the way, he’s amassed $255M in funding and been named Forbes Next Billion Dollar Startup, all while making renting your next apartment as easy as ordering takeout. Prior to Landing, Bill founded, scaled, and exited three companies, including the online grocery delivery marketplace, Shipt, which sold to Target for $550M. Bill shares his advice on navigating negotiations, how he discovered product-market fit by asking customers to pay before his product was even built, and why true partnership is critical for a successful acquisition.