Many have watched the HBO comedy series “Silicon Valley,” but in Nitin Rai’s own words, he lived that life. After college, he moved to the tech capital of the world, sleeping on couches with $50 in his pocket. Years later, Rai remains the CEO of First Insight, the company he started in 1994, as well as a major figure in Oregon’s investment landscape; as the President of TiE Oregon and a Founding Partner of Elevate Capital, Rai is one of the first people Oregon startups look to for getting their big ideas off the ground. In this episode, Rai recalls his rags-to-riches story, how his opinion of angel investing changed over time, and how being a person of color affected his ability to rise through the ranks of corporate America.

Recently, Cybersecurity has been a prominent topic of conversation for the entire world, which makes Malcolm Harkins’ role of paramount importance. He is Chief Security and Trust Officer at Cymatic, a start-up that works with clients to improve their cybersecurity infrastructure. Perhaps the most important word in Harkins’ title is “Trust,” given the numerous companies that have faced breaches recently, as he explains. For this reason, Harkins is devoted to putting security and privacy before compliance in the hopes of rebuilding that “trust” for clients and their thousands of users around the world.

In her mother’s own words, Ruby Zefo can’t go through a day without accomplishing something. With degrees from Berkeley and Stanford Law School, a stellar career at Intel and her current job as Chief Privacy Officer at Uber, it’s hard to argue with that statement. But perhaps her biggest challenge thus far is turning the seemingly unglamorous field of privacy law into something exciting. In this episode, Zefo discusses the role of privacy in providing great user experiences, and what it’s been like joining one of the most prominent tech companies in the world.

Being a leader at one of the largest tech companies in the world is certainly a challenge, but for Joel Levinson, what was even more challenging was searching for any semblance of work-life balance. After 30-hour trips around the world to locations which Levinson says he “will likely never see again,” he decided that the all-consuming work he was doing wasn’t worth the mental strain it caused him. Since leaving, he’s moved from Arizona to Vancouver, BC in search of a job that both satisfied his desire for a demanding, enjoyable position and his desire to spend more time with his wife and his two young children.

In this episode, Levinson discusses how being a leader doesn’t just involve leading a team but also managing yourself, emphasizing the importance of mental health along the way.

Earning the title of Chief Marketing Officer at any corporation is a major achievement, but to do it at Nike without prior marketing experience is incredible. Liz Dolan is no ordinary leader. Following her stint at Nike, she has worked as the CMO of the Oprah Winfrey Network, FOX Sports AND the National Geographic channel.

But on top of that, she’s also the co-creator of the Satellite Sisters. The wildly successful radio show-turned-podcast sought to give a female voice to a form of entertainment heavily saturated by male (usually conservative) personalities like Sean Hannity and Rush Limbaugh. 20 years, numerous awards and a book later, Satellite Sisters continues to bring Liz Dolan and her sisters together to give “pep talks for modern women,” as they have done since day 1.

In this episode, Dolan recalls her time at Nike, her relationship with her fellow Satellite Sisters and how gender bias forced her to resign from a board of directors.

TEDx’s mission is founded on the concept of “ideas worth spreading” and TEDxPortland curator and leader David Rae has taken that to heart. He developed TEDxPortland into one of the largest and most successful TEDx events globally by continually challenging the status quo and striving to get better. To help open the event to more great ideas, they created the “Ideas Booth,” a replica of a British telephone booth that allows anyone to share any idea in 90 seconds, in the hopes of becoming a speaker at their event.

It hasn’t always been smooth sailing. 2020 would have been their tenth anniversary, celebrated by hosting the largest (indoor) TEDx event ever held. But COVID-19 forced Rae to adapt once again to face the reality of life in a pandemic.

In this episode, we discuss how TEDxPortland has learned to thrive in the pandemic, and David shares the story behind TEDxPortland, what he’s learned along the way and a whole lot more.

The phrase “Leadership is no accident” is especially true when it comes to leading one of the most successful MLB teams in recent memory. Former San Francisco Giants GM Bobby Evans has transitioned from playing on college teams to managing some of the greatest rosters in the history of the sport. In this episode, Evans discusses a baseball team’s player-manager dynamic and what makes sports leadership distinct from other professions.

Mary Beth Martin is the Vice President of OHSU’s Doernbecher, one of the nation’s leading children’s hospitals. With hospitals undergoing huge changes in response to COVID, Martin is on the frontline helping her brave employees navigate the pandemic. In this episode, Martin talks about the administrative side of the healthcare industry, her employees adapting to new working conditions and her heartwarming adoption story.

Ex-MMA Fighter Daniel Puder takes the term “all hands on deck” to a whole new level. Using his My Life My Power academy to help underserved youth become the best version of themselves, Puder is relentless in his efforts to create positive changes in his community. In this episode, he talks transitioning from professional sports to nonprofit leadership and how significance breeds success.

Barbara Duffy is the president of Lane Powell, one of the oldest and most successful law firms in the Pacific Northwest. In this episode, Duffy talks about her position as the firm’s first female president, how Lane Powell is seeking positive opportunities during COVID-19 and her advice for anyone looking to follow in her footsteps.