Office Hours with Spencer Rascoff

Spencer speaks with Ian Cinnamon, the CEO and co-founder of Culver City-based startup Apex, which manufactures productized, configurable satellite buses for the expanding space industry. As access to space becomes democratized, Apex's is poised to offer its scalable solutions to both commercial and government customers.  Prior to Apex, Ian founded Synapse, a startup that built AI systems for the defense and security worlds, which he helped grow before it was acquired by Palantir. Ian is an alumnus of the Y Combinator accelerator program and received his undergraduate degree from MIT and MBA from the Stanford Graduate School of Business. (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Apex.)

Eddy Lu, CEO of GOAT, explains his pivot from a restaurant meet-up app, the ups and downs of working with his co-founder, and how insight into the sneaker vertical on eBay helped build the start-up into what it is today. This episode was originally released in February of 2011. 

Howie Liu is the co-founder and CEO of tech decacorn Airtable, a connected apps platform that lets users build and customize apps using shared data. As a no code platform, Airtable has iterated and innovated their product by combining the features of a relational database by using an interface that looks like a spreadsheet. Since it's founding in 2012, the company has raised nearly $1.4B in funding and is currently valued at $11B. In this episode, Howie talks about starting his first company, taking part in the Y Combinator accelerator, and how selling his company Etacts to Salesforce led him to innovating and creating products with enterprise clients in mind. Liu is a graduate of Duke University.

In this episode of Office Hours, Spencer speaks with L.A.-based entrepreneur Shiloh Johnson, the CEO and founder of ComplYant, a digital tax assistant tool. The technology platform offers small business owners and entrepreneurs an easy way to handle business taxes. The fintech startup was originally bootstrapped by Johnson, who as a Black female founder thought she'd be overlooked by VCs. Since then, Shiloh raised $5.5M in seed funding through Techstars’ Los Angeles program.

Bill Gurley, Legendary Silicon Valley VC, is a general partner at Benchmark and famously known for investing early in trailblazing companies including Uber, GrubHub, Zillow and so many others. Hear this conversation with Spencer from the dot.LA Summit where they discuss marketplace-based companies, how work-from-home will accelerate business opportunity, and why startups—though they might be attached to their autonomy—should pick up the phone when a big company calls. Plus, hear Bill’s thoughtful take on big tech and antitrust. This interview was originally published on December of 2020, and was recorded at the inaugural dot.LA Summit held October 27th & 28th.     

Growing up as the son of a nationally renowned veterinarian, Brandon knows first-hand the importance of having access to experts when your pet is sick. In 2018, Werber launched Airvet, a Beverly Hills-based digital health company for pets. Airvet works with employers and business partners to make sure pet parents get affordable and fast access to virtual vet care via video and chat. (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Airvet.)

Roy Swan, Director of The Ford Foundation's Mission Investments team, is committed to increasing the impact of their portfolio of mission-related investments (MRIs). He works alongside the organization's leadership to identify opportunities and guide decision-making processes as they relate to its global activities. Prior to joining the Foundation, Roy served as managing director and co-head of Global Sustainable Finance at Morgan Stanley. While there, he oversaw massive community development transactions that generated over $13 billion in value for investors.  Roy received his bachelor’s degree from Princeton University and a JD from Stanford Law School, where he was an editor of the Stanford Law Review.  

Spencer speaks with Isa Watson, the Founder & CEO of Squad. Watson, author of the upcoming book, "Life Beyond Likes: Logging Off Your Screen and Into Your Life." In the book, she raises awareness around how social media has impacted our daily lives, self-worth, and real life relationships. With so much of our lives lived online, Isa argues, we’ve never been more connected—or disconnected—from what’s most important to us. It’s time to let go of our curated online worlds and get beyond our need for likes. As the founder of Squad, an audio- focused app, Watson created a fun and easy way to stay in touch with your best friends everyday—away from the distractions of traditional social media.  

Diankha Linear, CEO of Community, an SMS marketing platform for business, speaks with Spencer in this episode of Office Hours. Ms. Linear was an officer and early executive team member at Convoy, serving as General Counsel and corporate secretary—overseeing one of Seattle’s largest VC transactions with a Series D Round of $400M, among other roles in the startup. Diankha comes from a strategy and leadership background, built on her years of military education and training with the Army and as a Judge Advocate General (JAG) officer. Ms Linear spent nearly a decade in leadership roles at Nordstrom and Expeditors International of Washington. Her early career was spent at big firm antitrust, complex commercial, constitutional, and employment law counsel. Diankha is a graduate of the University of Pennsylvania Law School and the University of Washington. (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Community.)  

Steve Case, co-founder of AOL and CEO of Revolution speaks with Spencer about his current mission to locate compelling investment opportunities outside of the traditional tech hubs like Silicon Valley. Case's Rise of the Rest Seed Fund is a Revolution initiative aimed at accelerating the growth of early-stage startups across the country. The ideas is that there's more opportunity for investors to back companies in other parts of the country during their early stages, since valuation and arbitration are lower in less competitive sectors. Starting about eight years ago, Case hit the road on a bus tour where he visited various cities around the U.S., contributing seed funding to local startups through pitch competitions, and speaking to local innovators, business, and policy leaders. Steve's latest book The Rise of the Rest: How Entrepreneurs in Surprising Places are Building the New American Dream is available now.

Spencer speaks with Sami Inkinen, the CEO and Founder of Virta Health. After winning the Ironman 70.3 World Championships in 2011, the triathlete found out that he was pre-diabetic that same year. Unsatisfied with the conventional wisdom of “exercise more and eat less,” Sami dug into the science of type 2 diabetes, by consulting experts on the science of carbohydrate restriction and metabolic health. Seeking to raise awareness about the dangers of sugar, Inkinen and his wife rowed across the Pacific Ocean for 45 days—completely unsupported—from California to Hawaii for 2,750 miles. While on that journey, the idea for Virta was born. His personal mantra on that trip was "Use Sisu, not Sugar"—with the Finnish concept of Stoicism, tenacity, and grit, as determination to help himself and others reverse their diagnoses.  Virta is an app-based, health technology start-up that offers treatment to reverse type 2 diabetes without surgery, allowing patients to work with medical providers and health coaches on a nearly real-time basis. Virta’s approach helps patients get off of all diabetes-specific medications while achieving sub-diabetic HbA1c (blood sugar)—in 60% of patients who complete one-year of the Virta Treatment. Of those patients prescribed insulin, 94% reduce or fully-eliminate usage.  Previously, Inkinen was the co-founder of real estate marketplace Trulia, serving as its COO and president and board member until its IPO and sale to Zillow Group. Sami is also an active angel investor in healthcare. Inkinen started his career as a radiochemist at a nuclear power plant. He holds a Master of Science in engineering physics from the Helsinki University of Technology, and a Master of Business Administration from Stanford University.  (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Virta.)

Julia Boorstin is CNBC’s Senior Media & Tech Correspondent and has been an on-air reporter for the network since 2006. She also plays a central role on CNBC’s bicoastal tech-focused program “TechCheck” delivering reporting, analysis, and CEO interviews with a focus on social media and the intersection of media and technology. In 2013, Boorstin created and launched the CNBC Disruptor 50, an annual list she oversees, highlighting private companies transforming the economy and challenging companies in established industries. She also helped launch the network’s ‘Closing the Gap’ initiative covering the people and companies closing gender and diversity gaps. Boorstin speaks with Spencer in this fireside chat recorded at the third annual dot.LA Summit, held on October 20 at The Petersen Automotive Museum located in Los Angeles. Julia’s new book When Women Lead: What They Achieve, Why They Succeed, and How We Can Learn from Them, profiles female entrepreneurs and businesswomen and draws lessons and inspiration from their stories. A graduate of Princeton University, Boorstin has been a reporter for Fortune magazine, as well as a contributor to CNN and CNN Headline News. She was also an intern for Vice President Gore’s domestic policy office. She lives in L.A. with her husband and two sons.

Tricia Han, the head of MyFitnesesPal speaks with Spencer about her journey from being a Product Manager to becoming a CEO in this episode of Office Hours. MyFitnessPal is a leading health and wellness tech brand, whose popular mobile app allows users to track their daily food intake. Tricia talks about the differences of working in East Coast tech vs West Coast tech, heading a start-up through a change management process, and the importance of representation in the tech space. Tricia also shares some suprising data points logged from L.A. users of the app.  Prior to MyFitnessPal, Tricia was the Chief Product Officer of Care.com, a U.S. marketplace connecting families and caregivers, CEO of Daily Burn, a fitness tech brand, and Chief Product Officer at Dotdash, all operating businesses of IAC. Her professional experience also includes leading product management teams at a variety of technology companies and start-ups including WebMD, DailyCandy, and Vindigo. Han earned her Bachelor of Arts from Cornell University.

Host Spencer Rascoff speaks to David Fields, founder and CEO of both Afterparty and Wander. Afterparty is looking to evolve the event-ticketing space with NFTs to assist creators, musicians and collectors. Previously, Fields worked at Disney and was part of the team that helped acquire Pixar. David was also formerly the head of acquisitions and investments for Disney CEO Michael Eisner’s Investment group, The Tornante Company. Fields has a BA in Economics from Harvard. (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Afterparty.)

As CEO and co-founder of Tomo, Greg Schwartz leads the company in its mission to transform the home buying experience. Tomo was founded in the fall of 2020 and raised a $70 million seed round, reportedly the largest in U.S. history. The company’s initial product, Tomo Mortgage, launched in June of 2021 to streamline the mortgage process by bringing e-commerce to the paperwork heavy part of home transactions. Previously, Greg was the lead business executive of Zillow Group for 13 years. Before Zillow, Greg was vice president of advertising sales at CNNMoney, where he launched the advertising sales team and platform. He also served as national accounts director for Yahoo's automotive and finance properties and held multiple senior roles at DoubleClick.  (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Tomo.)

Rand Fishkin, co-founder and CEO of SparkToro, and formerly of Moz speaks with Spencer in this revealing conversation about the ups and downs of entrepreneurship. Rand started out as an SEO enthusiast writing about increasing organic traffic through his SEOmoz blog, and then realizing that his expertise had the makings of a business, he began consulting and then developing Moz into a SaaS. Rand helped grow Moz to more than 130 employees, with over $30M in revenue, and traffic reaching 30M visitors per year. Rand is known for his marketing videos, public speaking, and his book Lost and Founder, in which he reveals with incredible candor his struggles with depression.  Rand Fishkin is an investor in dot.LA. 

In this episode of Office Hours, Spencer speaks with Colin Walsh, CEO and Founder of Varo Bank about the importance of their startup getting its charter and being FDIC insured, what it's like leading the way of a "challenger bank" in the fin-tech space, the tough decision he's had to make to stay competitive, and how the bank aspires to create financial inclusion by focusing on its younger customer base. Colin also talks about his journey through the financial services industry having worked for large corporate institutions like Wells Fargo, Visa, American Express, and Lloyd's Banking Group.  (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Varo.)

Blackstone Growth's Jon Korngold joins Spencer on this episode of Office Hours for a conversation about how the recent stock market downturn is affecting the tech sector and whether a market correction lies ahead. Korngold is Senior Managing Director and Head of Blackstone’s global growth equity investing platform, where he focuses on funding growth-stage companies. Prior to joining Blackstone in 2019, Korngold was on the Management Committee of General Atlantic, leading both the global financial services and health care sectors. Korngold also worked at Goldman Sachs and is a member of The Council on Foreign Relations. He's also active with Harvard University, where he serves on the Harvard College Fund’s Executive Committee.

Roman Kaplun is the CEO and Co-founder of Zoolatech, a custom software development company specializing in high-end software engineering based in the San Francisco area. Born in Leningrad in the former Soviet Union, his family moved to the United States as Jewish refugees in 1988, right after he completed High School. Zoolatech has workers in the U.S., Ukraine, Mexico, and Poland. The startup was able to evacuate, relocate, and resettle many of its employees from Kiyv after the Russian invasion of Ukraine on February 24.  Prior to Zoolatech, Roman held a number of Engineering Management and QA roles for Hotwire, Expedia, and IAC. Roman's career began in the maritime sector where he spent a few years at sea, mostly in commercial fishing. Roman has more than 20 years of experience overseeing critical information technology deployments for leaders in the e-commerce, Travel, Media, and Mobile space. Kaplun holds a Bachelor of Science degree in Transportation, Logistics, and Business Administration from California State University Maritime Academy.

On this episode of Office Hours, Spencer speaks with John Shegerian, CEO and chairman of ERI, the largest cybersecurity-focused hardware destruction and electronic waste recycling company in the United States. Shegerian is a serial entrepreneur who helped found FinancialAid.com, Addicted.com and Engage, LLC, a speaker-booking platform, among other organizations. In the early '90s, Shegerian co-founded Homeboy Tortillas and Homeboy Industries, led by Father Greg Boyle, to help improve the lives of former gang members in East Los Angeles. The organization has since evolved into the largest gang-intervention, rehab and re-entry program in the world. John is co-author of "The Insecurity of Everything" and "101 Tips from the Marketing Masters: Ways to Supercharge Your Marketing & Exponentially Grow Your Business." He also hosts "Impact with John Shegerian," a weekly podcast featuring conversations with some of the greatest business minds and thought leaders known today.

Spencer speaks with Maria Colacurcio, the CEO of Syndio Solutions on this episode of Office Hours. Syndio is a software startup helping companies around the world create an equitable workplace for all employees, regardless of gender, race or ethnicity. Syndio’s workplace equity platform helps companies close pay and opportunity gaps, mitigate legal risk and turn diversity, equity, and inclusion (DEI) goals into tangible results. Prior to joining Syndio, Colacurcio co-founded Smartsheet.com, which went public in 2018, and spent three years at Starbucks, one of the first Fortune 50 companies to make their pay equity results public. Colacurcio serves on the board of the nonprofit Fair Pay Workplace and has been named one of the 100 most intriguing entrepreneurs by Goldman Sachs' Builders and Innovators Summit. As a CEO and a mom of seven, Colacurcio is walking the walk on eradicating workplace inequities; she was able to raise a $17.1 million Series B investment in January 2021 while eight months pregnant (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Syndio.)

This episode features Nick Green, co-founder of Los Angeles-based ecommerce startup Thrive Market in conversation with Spencer. Nick speaks about selling his first company, a college test prep startup which was purchased by Revolution Prep, in his early twenties after graduating from Harvard. From there, his involvement with Launchpad LA helped him connect with Thrive co-founder Gunnar Lovelace. Nick saw firsthand the challenges of eating healthy while growing up in the Midwest. He says sticking with the core mission of solving America’s food access problem and mitigating "lifestyle diseases" has helped Thrive stay on track to scale their online marketplace concept. Thrive Market is an online health foods shop that offers its products at a lower cost from other retailers due its "Costco-styled" membership model. Thrive offers its own lineup of products, in addition to the many health and wellness brands that are found at other stores. Since its launch in 2014, Thrive Market has grown to more than 1 million paying members and become a case study of how mission-driven companies can scale through approaches that include carbon-neutral shipping, a focus on "zero waste" practices and getting certified as a B Corp.

On this episode of Office Hours, Spencer speaks with entrepreneur and venture investor David Beatty. David is a managing partner and co-founder of Gaingels, an LGBTQ investment syndicate. Started in 2014, Gaingels' mission is to foster social change through their investment portfolios by creating a more diverse, inclusive and accessible venture capital ecosystem. Their network does this by working with accredited investors interested in diversifying the startup world by building leadership among startup founders from traditionally underrepresented groups. David is also co-founder of Digital Irish Angels, a nonprofit organization investing in innovative companies in Ireland. This episode was recorded at the The Milken Institute Global Conference on May 2, 2022.

On this episode, Spencer speaks with iconic global business leader John Chambers in a live conversation that was recorded at the Montgomery Summit on May 24. Chambers, the former chairman and CEO of Cisco, currently serves as the founder and CEO of JC2 Ventures. The firm is focused on helping build and scale disruptive startups from around the world, largely by investing in companies that are leading market transitions. The Montgomery Summit is an exclusive, annual gathering of over 1,000 senior-level investors, thought leaders, corporate development teams, technology executives and top private company CEOs at the iconic Fairmont Miramar in Santa Monica.

Spencer speaks to Miami Mayor Francis Suarez on this episode of Office Hours. In this conversation he talks about his broad based views on the city’s tech economy, why he supports cryptocurrency, and took his salary in crypto (the city even has its own MiamiCoin). Mayor Suarez talks about the evolution of the local technology ecosystem through Venture Miami and its growing fintech, medtech, and greentech sectors. He is the son of former Miami Mayor, Xavier Suarez and is the first Miami-born mayor, and currently also serves as the president of the US Conference of Mayors.

In this episode of Office Hours, Spencer speaks with Congressman Derek Kilmer who serves as the United States Representative of Washington’s 6th Congressional District. Rep. Kilmer started his career as a business consultant for McKinsey & Company, then moved on to work for the Economic Development Board for Tacoma-Pierce County. He then began a career in local government in Olympia, serving in the Washington State House from 2005 to 2007 and the state Senate from 2007 until he was elected to the U.S. House of Representatives in 2012. Rep. Kilmer is now serving his fifth term in the U.S. House and is a member of the Appropriations Committee. He currently serves as the Chair for the Select Committee on the Modernization of Congress—which in this interview he dubs “The Fix Congress Committee.” The Committee was formed to develop recommendations to make Congress more effective, efficient and transparent. It looks at potential technology solutions, along with other ways to increase civility and collaboration. Kilmer was ranked the 33rd most bipartisan member of the House of Representatives during the 114th Congress by The Lugar Center's "Bipartisan Index."

Host Spencer Rascoff speaks with Ian Siegel, CEO and co-founder of ZipRecruiter on this episode of Office Hours. ZipRecruiter is an online employment marketplace that uses artificial intelligence to match businesses with job candidates in every industry. More than 1.8 million employers have used ZipRecruiter since its founding in 2010. Ian previously held leadership roles at CitySearch, Stamps.com and Rent.com. He received his B.A. in sociology from Oberlin College. He's now based in Santa Monica, California. His book “Get Hired Now!” is a Wall Street Journal bestseller. 

Spencer caught up with Mayor Stephen Adler at the Milken Institute Global Conference on May 2. Mayor Adler is the 58th mayor of Austin, Texas—a city that, along with L.A., has grown into a thriving hub of tech startups over the past two decades. Mayor Adler has received praise for his administration’s focus on innovation while staying true to the city’s slogan: “Keep Austin Weird.” Mayor Adler was born in Washington, D.C. and attended Princeton and the University of Texas Law School.

Aero CEO Uma Subramanian speaks to Spencer on this episode of Office Hours about her love of everything that flies. Her appreciation of flight was sparked by her visit to Space Camp as a child which led her on the path to study aerospace engineering. Uma got her start in the aviation industry working at Northrop Grumman under contract to NASA. After receiving her MBA at Harvard Business School, Subramanian went into consulting, then returned to aerospace. After a brief stint as the director of European operations for TaskRabbit, her career pivoted towards innovation in the aviation world. Uma was the founding CEO of Voom, an Airbus company, which built the world’s first urban air transportation system in São Paulo and Mexico City using helicopters–effectively creating one of the world’s first vertical takeoff and landing (VTOL) networks. Uma shares the strategies that Aero has used to build its luxury air travel brand by offering private flights at a lower price point.

On this episode of Office Hours, Spencer speaks to Philip Rosedale, CEO and cofounder of High Fidelity and founder of Linden Lab, for a wide-ranging conversation about Web 3.0 and the future of the metaverse. Rosedale, who recently rejoined Second Life as a strategic advisor, speaks about his vision on what the future of metaverse holds, and how startups can prepare to innovate around it. As a true pioneer in the early iterations of the metaverse and virtual reality, Rosedale shares what he’s learned about the challenges and opportunities that face the growth of what has become the biggest new buzzword in tech. This talk was originally broadcast as a live online discussion on Zoom that took place as part of Madrona Venture Labs “Launchable: Web3 Startups” event on March 18, 2022.

Liz Jenkins, the COO of Hello Sunshine talks about how the media company looks to put women at the center of the narrative. The L.A.-based company was founded by actor Reese Witherspoon and dedicated to female authorship. Their stories aspire to be both fun and informative and to spread contagious joy through the women at the heart of their storytelling. Liz, who joined the company as its CFO in 2018, talks about the career path that took her from investment banking to the entertainment industry. During her time at Hello Sunshine, she’s helped grow the company’s business, including their scripted, unscripted and kids & animation studios, plus Reese’s Book Club. Previously, Liz served as the head of strategic ventures for Sony PlayStation and senior vice president of corporate development and strategy at Media Rights Capital (MRC) where she developed and implemented innovative distribution models, strategic partnerships and new businesses across film and television. Liz serves on the board and audit committee of Snap Inc. and is a board member and the Treasurer of GLAAD. Liz received her M.B.A. from The Wharton School at the University of Pennsylvania and her B.A. from Stanford University.

With her longstanding Wall Street career (Citigroup, Merrill Lynch) and unique perspective as a woman in a predominantly male industry, Sallie Krawcheck is tackling a question that has mystified investment banks for decades: how to successfully market wealth management services to women. As CEO of digital financial investment platform Ellevest, she sees diversity as the greatest advantage in cracking the code. Krawcheck encourages each employee to bring their "whole self" to work, and emphasizes hiring the best fit for the team, which in some cases could be a different choice than the person who traditionally would be considered the best fit for the role. This interview was originally published on September of 2016.

Ryan Serhant, one of the most visible real estate brokers in media, chats with Spencer about his inventive approach to sales on this episode of Office Hours. Ryan is known as one of the stars of Bravo’s Emmy-nominated "Million Dollar Listing New York," and its spin-off show "Sell It Like Serhant." Ryan tells the story of how he wound up working as a real estate agent after arriving in New York to support his dream of becoming an actor. It started as a way to cover his rent and living expenses. What followed was a wildly successful career in real estate. His team was ranked number 1 in New York by the "Wall Street Journal" for three straight years. After a decade of leading that sales team he founded SERHANT, a cloud brokerage designed around the digital marketplace. The brokerage’s in-house production team and tech platform has reinvented the traditional business model, bringing in over $4 billion in sales and selling more than 80 new development projects across New York, Los Angeles and Miami.

Spencer speaks with Calvin Selth, program manager for AnnenbergTech at the Annenberg Foundation on this episode of Office Hours. In his role at the foundation, Calvin leads operations and program management for PledgeLA, a collective of more than 220 tech companies and venture capital firms hosted in partnership with L.A. Mayor Eric Garcetti. PledgeLA's mission is to connect civic, private sector and nonprofit partners to increase access to jobs and capital for underrepresented communities.  Calvin began his career as a bilingual K-8 educator, and has used his past experience in talent recruitment, nonprofit development and event marketing to gather people from diverse backgrounds around shared goals. He graduated magna cum laude from Cornell University and holds a certificate in leadership and management from the Wharton School. 

Paul Hanges, CEO of JibJab speaks with Office Hours host Spencer Rascoff about how the L.A.-based digital entertainment studio has attained success beyond its viral videos by moving into the eCards space and using its unique blend of satirical humor to compete with rivals Hallmark and American Greetings. Founded in 1999 by brothers Evan and Gregg Spiridellis, the company first achieved widespread attention during the 2004 U.S. presidential election. Their video of candidates George Bush and John Kerry singing “This Land Is Your Land” became a viral hit. JibJab has produced commercials and short videos for clients including Sony, Noggin, Cartoon Network, Nickelodeon, PBS Kids, Sprout, NBC, Qubo and Disney before focusing on what eventually became their flagship personalized eCard and messaging services. They've seen surprising success with their animated sticker-making program which became a top App Store download. In 2019, JibJab was acquired by the private equity firm Catapult Capital.

Steven Wolfe Pereira, CEO of Encantos talks with Spencer about how the EdTech start-up uses "storyteaching" to help kids learn 21st-century skills. With diversity, equality, and inclusion (DEI) baked-in to the Public Benefit Corporation's mission, Encantos seeks to unlock talent from creators around the world to help build inclusive Storyworlds around the characters that make up its Intellectual Property. The platform, co-founded with author/illustrator Susie Jaramillo, who serves as President and Chief Creative Officer helped create Canticos, an Emmy-nominated bilingual baby and toddler brand. Headquartered in Culver City, the start-up has raised a total of $8.5M in over three rounds of funding. Steven Wolfe Pereira began his career in finance at The Blackstone Group and has had roles as the CMO of Datalogix, Neustar and Quantcast. He earned a B.A. from Tufts University, was a Fulbright Scholar and earned his MBA from MIT’s Sloan School of Management. A Dominican-American born and raised in New York, Wolfe Pereira now lives in Los Angeles with his family. (Disclosure: dot.LA co-founder Spencer Rascoff is an investor in Encantos.)

Russ Glass, CEO of Headspace Health, a digital mental health and wellbeing platform, speaks with Spencer about his involvement overseeing the surge in the Telehealth market after the merger of Headspace and Ginger. Glass, a serial tech entrepreneur—who was also formerly Founder of Bizo, Inc., aqcuired by LinkedIn— speaks candidly about his successes and failures with previous start-ups and why he believes that there is such overwhelming demand for the healthcare services that Headspace offers.

Allison Ellsworth and her husband Stephen, formerly employed in the oil and gas industry, quit their jobs to bet on themselves and and started a health-based soda alternative. Their concept, a prebiotic drink called Poppi masks the strong taste of apple cider vinegar using less than 6 grams of sugar to help support gut health. The Texas based start-up was funded by Rohan Oza after the couple went on Shark Tank who helped them work on a rebrand. Allison, who was 9 months pregnant shares how the company has focused on its digital and retail sales strategy, and why they are moving their team from Dallas to Austin.

This conversation explores the L.A. tech scene and venture investing featuring two of the industry's leading voices. Spencer Rascoff and Dana Settle discuss Pacaso and Greycroft while sharing their thoughts on L.A.'s evolving ecosystem. Dana Settle is a founding partner of Greycroft, where she heads the firm’s West Coast office out of Los Angeles. Prior to joining Greycroft, Dana spent several years as a venture capitalist and advisor to startup companies in the Bay Area, including six years at Mayfield, where she focused on early stage companies in the mobile communications and consumer Internet markets. Dana currently manages Greycroft’s investments in Anine Bing, AppAnnie, Avaline, Bird, Bumble, Citizen, Clique, Comparably, Goop, HamsaPay, Happiest Baby, Merit Beauty, Seed, Thrive Market, Versed, and WideOrbit. She also managed the firm’s investments in The RealReal (IPO), Awesomeness TV (acquired by Dreamworks), Maker Studios (acquired by Disney), Pulse (acquired by LinkedIn), Trunk Club (acquired by Nordstrom), Sometrics (acquired by American Express), Viddy (acquired by Fullscreen), and Voicea (acquired by Cisco). Show notes and resources: Dana Settle bio on Greycroft Both sides of the table Diversity Ride for the Term Sheet  

In this fireside chat with dot.LA and Pacaso co-founder and chair Spencer Rascoff, Jam City President and co-founder Josh Yguado explores what the acquisition of Ludia means for the future of Jam City and mobile gaming. The discussion covers what it means to sit at the intersection of traditional entertainment and mobile gaming and why L.A. is the perfect place for this work.  Jam City is reimagining the future of mobile gaming. Already an award-winning company behind the world’s most enduring mobile games, the company’s recent acquisition of Ludia bolsters its global portfolio of top studios that develop and publish top-grossing games.

My friend, serial entrepreneur and legendary real estate coach, Tom Ferry, shares his career trajectory from sales to coaching phenom, the single biggest pitfall for work performance and his take on California’s business climate.

Chris Webb rejected attending college in favor of diving into a finance career at eighteen years old. Now, he’s the CEO and co-founder of ChowNow, an app and online ordering system for restaurants that doesn't charge the onerous fees required of other delivery services. Hear Chris share how his education steeped in Wall Street and his mother’s surprise restaurant investment came together to ultimately inspire ChowNow.

Shoeboxes full of invoices and receipts ignited the idea of Service Titan for Ara Mahdessian, the company’s CEO and cofounder. An Armenian immigrant from Iran, Ara came to the U.S. with his family as a young boy. He watched his parents assimilate to their new country while toiling into late hours of the night in order to give their family a good life. Their hard work paid off. Ara attended Stanford where he studied software engineering. He and his cofounder, Vahe Kuzoyan, also a software engineer, applied their knowledge to create automated software for home and commercial service businesses like plumbing and electrical. This includes scheduling, dispatching, payroll, recording, payments, invoicing, etc. Hear why Ara feels having an engineering background makes him a better leader, what to look for in investment partners and the values he emphasizes at Service Titan to ensure a high-quality, supportive and productive company culture.

Before PayPal, there was Bill Point, a company cofounded in the late 90s by Keith Richman, now cofounder of Boosted Commerce, which buys top-rated companies on Amazon and other e-commerce ecosystems and helps take them to their next level. Hear how the arc of his serial entrepreneurship follows the trajectory of the internet, what Boosted looks for in their acquisitions and what Boosted offers their companies to help them grow.

As a self-taught teenage computer programmer in Brazil, Henrique Dubugras launched his first company, Pagar.me at age 16. After he sold it, Henrique was accepted and enrolled at Stanford, but dropped out early to follow his entrepreneurial instincts. This led him to co-found Brex with Pedro Franceschi, a business-to-business fintech unicorn disrupting the century old industry of banking small businesses.

Birds were the first dwellers Austin Allison, CEO and co-founder of Pacaso, served with his boyhood bird-house business. Now, with Pacaso, the serial entrepreneur aims to democratize second home ownership by enabling people to co-own an amazing second home --- for 1/8 the cost. Hear his take on what it meant to have his first company acquired, his number one tip on how to keep his crew focused and how to best navigate what seems like weekly iterations of the start-up environment.

If there’s one thing to be learned from CEO and co-founder of Health-Ade, Daina Trout, it’s to pay attention to the opportunity in front of you and be prepared to pivot. Hear how Health-Ade Kombucha evolved from a hair-loss remedy to a huge brand of healthy drinks, learn about Daina and Spencer’s philosophy around hiring and gain insightful learnings around fundraising.

Hear from GOAT cofounder and CEO Eddy Lu about big, public and most importantly, resolved founder fights, insight on when to know it’s time to pivot or quit, how GOAT differentiates itself from other sneaker e-commerce sites -- and one of GOAT’s early and clever growth hacks to convince consumers the company had more merch than they actually did.

The burgeoning Los Angeles start-up and tech scene led to the founding of dot.LA one year ago. Today, we hear from its CEO and Spencer’s cofounder, Sam Adams, on how its mission both celebrates and holds accountable the burgeoning Los Angeles tech and start-up scene, how it’s baked DEI into its mission -- and why LA is the place for entrepreneurs to dig roots.

Ynon Kreiz served on the board of Mattel before stepping in as CEO in 2018. Hear about how Mattel is leverage its massive brand portfolio across multiple platforms, from toys to films, how Mattel is working towards environmental sustainability and the priority Mattel places on DEI. Also, hear the answer to a burning UNO game question hotly debated in Spencer’s family.

A free-flowing conversation packed with entrepreneurial lessons with serial entrepreneur, Beauty Counter founder, Gregg Renfrew. Hear what to look for in an investor, ideas about scaling, her passion for multi-channel business -- and why people should get rid of non-stick pans.    

Cameo’s highly-anticipated 2017 launch tanked. Its only talent was furious. But the startup persisted, and through grit has grown massively. Hear Steven Galanis, founder and CEO of Cameo, share the colorful story of the young company’s turnaround, how Galanis breaks down the best way to handle employee dysfunction and how he built up Cameo’s roster of tens of thousands of celebrities and influencers ready to send custom-crafted messages.

Bill Gurley, Legendary Silicon Valley venture capitalist, is a general partner at Benchmark and famously known for investing early in trailblazing companies including Uber, GrubHub, my company, Zillow and so many others. Hear a conversation he and I had at the recent dot.LA Summit where we discuss marketplace-based companies, how work-from-home will accelerate business opportunity and why startups, though they might be attached to their autonomy, should pick up the phone when a big company calls. Plus, hear his thoughtful take on big tech and antitrust.

Huge musical success is not enough for the electronic musical group, The Chainsmokers, made of Alex Pall and Drew Taggart. As part of their hunger to grow and learn, they've started their VC firm, Mantis, where they focus on investing in Seed and Series A startups. Hear about how they see the similarities between building startups and making music, the value add they give to companies beyond their fame and reach, how they write their songs and the why behind what might be considered a controversial move -- selling their music catalog.

How tough is it to infuse a retail website with entirely new products every day? Very. Nonetheless, that’s what Zulily, an ecommerce site that sells unique retail brands primarily to women, did when it went live in 2010. Ultimately, Zulily sold for $2.4 billion in 2015. Hear Darrell Cavens, founder and former CEO of Zulily, Spencer and Harvard Professor Jeffrey Rayport discuss the why behind Zulily’s astonishing success and some granular lessons learned born of a company that grew incredibly big incredibly fast.

It’s not easy to turn around a company. But some executives seek out that challenge. An experienced turnaround expert, Brad Stewart is the relatively new CEO of Fair, an app to lease used, affordable cars for as long as desired. Brad started out in management consulting before becoming CEO of then-struggling XO Jet. After seven successful years at XO Jet, Brad now brings to Fair a wealth of experience. Hear his insight on the steps he takes to fix companies, the unique issues facing Fair and the plan he’s putting into action to help the company thrive.

Years of work experience, largely solving business problems for his family, gave Jiake Liu a fundamental understanding of how to run a successful business. It also fed his entrepreneurial thirst and ultimately led to his cofounding and leading Outer, an outdoor furniture and lifestyle company. Hear some hard-earned lessons from Jiake about startups, his Shark Tank pitch day experience and how he maintains investor relationships even if they pass on investing -- like Spencer did.

Too many fashion options is a pain point Terry Boyle, cofounder and CEO of Behold, aims to solve with his newly launched retail platform. Hear how Terry, who’s been in fashion tech for over ten years with most of that time spent at the venerable Nordstroms, is competitively positioning and running his trailblazing company.

Inspired in the midst of the MeToo awakening, Claire Schmidt founded All Voices. It’s a platform that allows employees to anonymously share feedback with company administration without fear of reprisal. Hear Schmidt, CEO, share the problems All Voices is trying to solve, how the communication process works -- and an early lesson learned that forced All Voices to quickly make a radical pivot. And yes, All Voices uses All Voices!

On a mission to improve healthcare for every American, by offering steeply discounted prescription drugs, Doug Hirsch, cofounder and CEO of GoodRx, speaks with Spencer about how he built the business with a slow and steady attitude, how paranoia keeps him on his toes -- and why naivete is an entrepreneurial strength.

Sunil Gunderia, Chief Strategy Officer of Age of Learning, says two-thirds of America’s fourth graders are not proficient in english language arts or math despite the $700 billion spent on K-12 education. This disparity spurred the creation of Age of Learning, whose flagship product, ABC Mouse, has 30 million young learners on the platform since its launch in 2010. Hear Gunderia describe the Age of Learning business model, how it’s expanding during the time of Covid and what diversity, equity and inclusion measures Age of Learning is taking.

Stripped of their outdoor gear before their move to Los Angeles, Rachelle Snyder and her husband, Ross Richmond, arrived, surrounded by tantalizing outdoor adventure, but unprepared to enjoy it -- and nowhere to turn. That problem led them to cofound Arrive Outdoors, a company that rents camping, hiking and skiing gear and attire. Hear Rachelle dig into the details of partnering with brands, how best to service the consumer -- and why running the business with her husband works.

With so many people out of work, how is it the stock market is soaring? To make sense of it all, listen to Spencer as he speaks with John Scuorzo and Zaheed Kajani, both senior managing directors at Evercore, a global independent investment banking advisory firm. This is an edited version of a webinar that took place on June 23, 2020.

No matter how challenging, if given the choice, Jason Kilar, founder of Hulu and current CEO of WarnerMedia, would willingly disrupt the way television and film was distributed, all over again. Listen to Kilar’s account of contextualizing business during the burgeoning days of the internet, the early, tumultuous times at Hulu, his predictions about where media and entertainment are heading -- and a missed opportunity Jason wishes he had captured.

During the past decade, the Hollywood entertainment industry has worked towards more inclusivity in their ranks and storytelling. Can Los Angeles Tech employ those learnings? Angela Robinson and Alexandra Kondracke are film and television writers, producers and directors, known for their work on Professor Marston and The Wonder Women, True Blood, Hung and The L Word. They’re also founders of Time’s Up, a movement that aims to create a safe and equitable society free of sexual harassment. In this high-energy, frank conversation, hear Spencer, Angela and Alexandra share insight into both the Tech and Entertainment industry, how far the industries have come and how far they have to go. This was recorded well before Covid-19 hit and the protests related to George Floyd’s death.

Led by Tim Ellis, Relativity Space is radically upending the aerospace industry by manufacturing rockets using 3D printers. Hear Spencer and Tim dig into Relativity’s engineering feats, its vision for the future of humans in space, what the cutting-edge company values above all, and how in the not-too-distant future Relativity hopes to send a 3D printer to Mars to print rockets there.

Los Angeles has come a long way in the 20 years that Brian Lee has built up startups. Brian co-founded LegalZoom in 2001, ShoeDazzle with Kim Kardashian in 2008,  and The Honest Company with Jessica Alba in 2012. Now, Brian is co-founder and managing director of BAM Ventures, an early stage fund and startup studio, based in Los Angeles. Hear Spencer and Brian, recorded at the Montgomery Summit earlier this year, discuss Los Angeles’ evolution as a tech hub. They dig into the exciting state of the current Los Angeles start-up scene, what BAM looks for in founders, thoughts on building brands -- and a company Lee regrets he passed on. 

Managing through crisis is difficult, but great leaders and great companies are created during challenging times. Spencer grappled with crises at two companies he cofounded, Hotwire and Zillow.  Hear him and Katie Curnutte, former SVP of Communications at Zillow and now a partner at Kingston Marketing Group, discuss how to manage a company through the strain of calamity while keeping a steady eye on the big picture and the opportunities that can arise.

Earlier this year, Spencer had an opportunity through the Navy’s Distinguished Visitors Program to visit the USS John C. Stennis, an aircraft carrier. During his time aboard the ship, Spencer met Rear Admiral Michael Wettlaufer, who’s spent 32 years serving in the Navy. Throughout his career, Admiral Wettlaufer has received multiple medals for his service, logged 3,500 flying hours, flown 49 different aircraft types and made over 800 arrested landings. To say he’s a brave and accomplished leader is an understatement. In this episode, Spencer returns to the USS Stennis for a conversation with Admiral Wettlaufer about leadership. The two cover a lot of ground, including the admiral’s impressive career in the Navy, the importance of teamwork and how to build a culture that’s committed to excellence.

Nick Huzar is co-founder and CEO of OfferUp, the largest mobile marketplace in the U.S. The company has reinvented the model for local, peer-to-peer commerce, and its engagement metrics are incredible. In 2017, the company reported that it had over 60 million downloads and 43 million users who use the platform as frequently as popular social media apps. Today, OfferUp is one of the highest valued private companies in the Pacific Northwest, officially gaining “unicorn” status. In this episode, Nick offers advice for leaders about scaling a company, the importance of building trust and how his leadership style has evolved with OfferUp’s growth.

In this episode, Russell Wilson joins Spencer at Zillow Group’s Seattle headquarters for a live recording in front of employees. Russell is the starting quarterback for the Seahawks, leading the team to its first Super Bowl win in 2014. He’s also one of the NFL’s most charitable athletes. Russell founded the Why Not You Foundation, which has raised millions to support Strong Against Cancer and other children’s charities. When he’s not on the field or engaged in philanthropy, Russell is also an entrepreneur; he founded TraceMe, a social media platform, and Limitless Minds, a leadership development company. In this episode, Russell and Spencer discuss Russell’s approach to leadership on and off the field, how to overcome adversity, his latest business ventures – and even his proposal to Ciara.

Van Jones hosts his own show on CNN, and he’s the founder of The Dream Corps, an accelerator that supports economic and environmental innovation. Its #YesWeCode initiative aims to help 100,000 young people from underrepresented backgrounds find success in the tech sector. Van is an important voice on social justice and STEM education, and Time Magazine named him one of the 100 Most Influential People in the world. In this episode, Van joins Spencer at Zillow Group’s New York office for a live recording in front of employees. The two discuss Van’s impressive background working in communities and promoting green jobs, how to increase diversity in tech and why young people have the power to change the world.

Stewart Butterfield is the co-founder and chief executive officer of Slack, a collaboration hub beloved by more than eight million daily active users. In this episode, Spencer joins Stewart at Slack’s San Francisco headquarters to discuss their recent partnership with Atlassian, Slack’s unique origin story, managing through growth and adversity, and how Slack is fundamentally changing communication at work.

John MacFarlane served as CEO of Sonos from 2002 to 2017 and was instrumental in building the company’s loyal customer base. Just last week, Sonos filed to go public in a $100 million initial public offering, and the company is on track to do $1 billion in revenue this year alone. In this episode, John discusses Sonos’s decision to partner with competitors like Google and Amazon, why he stepped down as CEO and why it’s important to be relentlessly progressive.

Adena Friedman is president and chief executive officer of Nasdaq, which operates the second-largest stock exchange in the world by market cap. Named one of Forbes’ most powerful women, Adena built her career at Nasdaq, starting as an intern straight out of an MBA program. Outside of a three-year stint as chief financial officer at The Carlyle Group, she’s been with Nasdaq ever since. In this episode, Spencer joins Adena in New York City to discuss the power of mentorship, the future of the U.S. capital markets and why going public can spark innovation.

Emily Chang is a best-selling author and host and executive producer of Bloomberg Technology. Earlier this year, she made waves with her book “Brotopia,” an expose on how sexism became pervasive in Silicon Valley, despite its utopian ideals. Drawing on interviews with some of tech’s biggest names, Emily shines a bright light on a big problem. In this episode, Emily joins Spencer at Zillow Group’s San Francisco office to discuss her inspiration for the book, how the tech community got to this point and what we can do about it.

Alaska Airlines CEO Brad Tilden is in the midst of his "what's next" agenda following the company's successful acquisition of Virgin America. Acquisitions, no matter how well executed, are almost always tough on companies. But the commonalities between Alaska and Virgin - their focus on customers and building alignment among employees - lays the foundation for the former competitors to work together and adopt the best features of both airlines as they move forward under a single brand.

What will the home of the future look like? Imagine built-in Wi-Fi, voice-activated digital assistants and other technological innovations that will render older homes obsolete before long. Earlier this month, the nation’s largest homebuilder, Lennar, took a big swing in this direction, announcing that all of its new homes will include smart locks, Wi-Fi, thermostats and lights — all controlled by Amazon Alexa. In this episode, Lennar’s former CEO Stuart Miller, who now serves as its executive chairman, joins Spencer to discuss how technology will impact homebuilding and design — and how he helped create a culture that embraces innovation at the 60-plus-year-old company.

Comedy writer and producer Robert Carlock's spectacular career includes writing and producing credits on iconic shows such as "Saturday Night Live," "Friends" and "30 Rock." Most recently he co-created the Netflix original series "Unbreakable Kimmy Schmidt,". As a leader in a creative field, Robert doesn't rely on data to make decisions. Instead, he draws largely from his intuition and simply knowing what's going to be funny. And untethering creativity is a lesson all companies and industries can learn from.

Dara Khosrowshahi is CEO of Uber, a company that’s become a household name for transportation. Uber’s dominance hasn’t come without controversy, however. Uber’s reputation as an innovator has often been overshadowed by negative revelations about its culture. In 2017, Dara left his role as CEO of Expedia to take over the reins at Uber from founder Travis Kalanick. His mission: Get the company on the path to cultural reform, profitability and, eventually, IPO. In this episode, Dara and Spencer discuss why he made the move to Uber, what he’s learning – and the role of “flying taxis” in Uber’s future.

We revisit our conversation with Eric Holder. Eric knows a thing or two about introspection. In his current role, companies tap the former U.S. Attorney General to ask difficult questions and help businesses improve everything from diversity to how they work with foreign governments. With the democratization of information and the rise of social media, today's leaders and companies can no longer hide behind a great PR team. According to Holder, "Companies can always be introspective in the same way that we can be as individuals and ask tough questions of ourselves or as corporate entities. What are our strengths? What are our weaknesses? How can we do better?"

It’s no wonder Fortune Magazine called Cindy a “tireless force of nature.” She’s the entrepreneur behind the first-ever FDA approved drug to treat decreased libido in women, and she’s built two businesses from the ground up, selling them for over $1.5 billion. After securing FDA approval for ADDYI, dubbed “female Viagra” by numerous media outlets, Cindy founded The Pink Ceiling, an incubator and venture capital firm dedicated to helping women-focused businesses. In this episode, she and Spencer discuss the importance of empathy in product design, how the #MeToo movement will alter the venture capital landscape and why Cindy is an unapologetic proponent of the color pink.

Arianna Huffington needs little introduction. The author of 15 books, including best-sellers Thrive and The Sleep Revolution, Arianna has been named to Time Magazine’s list of 100 Most Influential People and Forbes’ Most Powerful Women list. In 2016, she stepped down from her namesake Huffington Post (now HuffPost) to launch Thrive Global, which aims to eliminate the stress and burnout that leave so many of us in survival mode. Arianna also joined Uber as its first woman board member, advocating for a culture where “brilliant jerks” aren’t tolerated. In this episode, Arianna joins Spencer at Zillow Group’s New York City office to discuss her newest venture, why leaders need to model balance for their employees and why we all need to prioritize downtime.

Sukhinder is a serial entrepreneur and longtime technology executive who had stints at both Google and Amazon. In 2015, she founded theBoardlist, a talent marketplace for leaders to find highly qualified women to join their boards. Among startups, 57 percent have no women in executive positions. On boards, more than three-quarters of privately funded tech companies have no women, and the picture is even worse among public companies. In this episode, Sukhinder discusses why the tech community should add more women partners, executives and board seats – and why she’s optimistic about the future of women in tech.

Companies that transform our lives with one innovation (like Microsoft Windows) often find it difficult to repeat the same feat because everything - from product to revenue to culture - is built on top of that one big idea. This is the challenge Satya Nadella faced when he took over the reins at Microsoft. How could he ensure that the 43-year-old company seized new opportunities and warded off potential threats? The answer: Build the ability to hit refresh into the culture by focusing on mission, leadership and growth mindset.

Eric Holder knows a thing or two about introspection. In his current role, companies tap the former U.S. Attorney General to ask difficult questions and help businesses improve everything from diversity to how they work with foreign governments. With the democratization of information and the rise of social media, today's leaders and companies can no longer hide behind a great PR team. According to Holder, "Companies can always be introspective in the same way that we can be as individuals and ask tough questions of ourselves or as corporate entities. What are our strengths? What are our weaknesses? How can we do better?"

The companies within Bill Gurley's investment portfolio have some clear similarities: great user-generated content, a reliance on the network effect and a "power to the people" mentality, meaning they put consumers first. But companies don't succeed solely because of their business model or mission - they also need strong leadership. According to Bill, great leaders tend to be unafraid, innately curious and bold. He looks for these qualities in the founder pitching the investment opportunity because - while the idea is important - it's the person who is going to execute it. In this episode, Bill references his 2012 essay, "The Dangerous Seduction of the Lifetime Value (LTV) Formula." You can read it in its entirety here.

As a founding member of several successful companies (Fog Creek, Trello) in the software development space, you could say that Joel Spolsky knows a bit about developers. On his popular online forum, Stack Overflow, developers ask more than 8,000 questions a day to a community of roughly 40 million developers who visit the site every month. Joel talks about software developers with a reverence normally reserved for philosophers: "Every day, developers get a chance to make a decision that's going to impact the world," he says. But with that power comes great responsibility, and managers have an important role to play in helping developers consider unintended consequences and use their power for good.

When John MacFarlane and his co-founders started Sonos in 2002, they knew nothing about audio or hardware. They simply had an inspiring mission: Fill every home with music. And they knew that the future of music wasn't CDs - it was wireless, digital and connected. In order to stay competitive in an industry that's changing, you have to lead with disruption and never stop improving, and it's this commitment to continuous improvement that has propelled Sonos to outsell some of the world's biggest tech companies in the home audio category.

Comedy writer and producer Robert Carlock's spectacular career includes writing and producing credits on iconic shows such as "Saturday Night Live," "Friends" and "30 Rock." Most recently he co-created the Netflix original series "Unbreakable Kimmy Schmidt," now entering its third season. As a leader in a creative field, Robert doesn't rely on data to make decisions. Instead, he draws largely from his intuition and simply knowing what's going to be funny. And untethering creativity is a lesson all companies and industries can learn from.

Dubbed Silicon Valley's "oddest couple" by The New York Times, together Sheryl Sandberg and Mark Zuckerberg have driven Facebook's astronomical growth and supported one another along the way. The keys to their successful COO-CEO partnership: open communication, commitment to their relationship and shared values.

With a storied career that includes leading coalition forces and counterinsurgency efforts in Iraq and Afghanistan, Retired Army Gen. David Petraeus definitely knows a thing or two about leadership. According to Petraeus, effective leaders don't dictate the tactics; they establish the mission, boundaries and direction, then empower the team to determine the best route. Great leaders also understand that, sometimes, big ideas need to evolve — whether they're running a military operation or private-sector company.

Alaska Airlines CEO Brad Tilden is in the midst of his "what's next" agenda following the company's successful acquisition of Virgin America. Acquisitions, no matter how well executed, are almost always tough on companies. But the commonalities between Alaska and Virgin - their focus on customers and building alignment among employees - lays the foundation for the former competitors to work together and adopt the best features of both airlines as they move forward under a single brand.

With managing a relocation, a mammoth real estate development and significant leadership changes on the coaching staff, L.A. Rams COO Kevin Demoff has a had a tumultuous couple of years. So how does he measure his organization's success? It's all about confidence in the coaching leadership - from the players, the front office and the fans.

Gaming is big business - a fact that perhaps no one knows better than Brandon Beck, co-founder and CEO of Riot Games. Riot's League of Legends is an eSports juggernaut and ushered in a new era of competitive gaming where events draw tens of thousands of spectators and hundreds of thousands more via streaming. Riot hires exclusively gamers, something Brandon admits can be a pain point, but a policy that's essential in understanding League's audience and creating a product that will keep players entertained and challenged over the long term.

Nearly a year and a half ago, The Huffington Post's legendary founder Arianna Huffington recruited Jared Grusd from his role as head of strategy at Spotify to lead Huff Post as she transitioned to her newest business venture. Jared spent an entire year with Arianna learning the ins and outs of her vision for Huff Post and unpacking its core identity and the key drivers of its success. Jared's role, as he put it, was to "figure out the next chapter."

During her 27 years in the private sector, Secretary Penny Pritzker started five companies, led dozens of businesses and served on the boards of big corporations like Hyatt Hotels, LaSalle National Bank and the William Wrigley Company. When she answered President Obama's call to serve her country, Pritzker's arena switched from private to public, but her objectives and challenges as a leader didn't change.

About this episode's guest: CEO of OpenTable, which was founded nearly 20 years ago Previously CFO of Playdom, which was acquired by Disney in 2010 Left "armchair quarterbacking" on Wall Street for the gaming industry Topics covered in this episode: Broadening the scope of possibilities through technology Balancing a simultaneously mature and entrepreneurial environment Being an innovator in a traditional industry

About this episode's guest: Founded Box at age 20 with three friends from high school. Prolific user of social media, with 678,000+ followers. Known for wearing bright-colored sneakers. Topics covered in this episode: Why Levie chooses to be outspoken politically. How the future of work is changing. Which types of companies will and won't be disrupted -- and why. The benefits of being a publicly traded company. Differences between the San Francisco and Seattle tech and venture capital scenes.

With her longstanding Wall Street career (Citigroup, Merrill Lynch) and unique perspective as a woman in a predominantly male industry, Sallie Krawcheck is tackling a question that has mystified investment banks for decades: how to successfully market wealth management services to women. As CEO of digital financial investment platform Ellevest, she sees diversity as the greatest advantage in cracking the code. Krawcheck encourages each employee to bring their "whole self" to work, and emphasizes hiring the best fit for the team, which in some cases could be a different choice than the person who traditionally would be considered the best fit for the role.

Scott Svenson believes in second chances. The serial entrepreneur's latest venture, MOD Pizza, embraces what he calls "enlightened capitalism." Yes, the company aims for profitability, but not at the expense of its greatest asset -- its employees. Many MOD Squaders find the fresh start that they need at the company, earning a level of trust that in turn creates a great customer experience.

Citigroup CEO Michael Corbat believes that physical office space plays an important role in shaping a company's culture. In fact, you won't find the corner offices traditionally associated with the financial services industry in Citi's NYC headquarters. Instead, the space is completely open and modern, creating multiple "collision points" that foster a culture of collaboration. In this episode, Corbat explains how making the job feel personal helps attract and retain talent, especially millennials -- who often have different career expectations than previous generations.

Listen. Decide. Communicate. These three steps form Dick Costolo's model for open communication and honesty in the workplace. It's a lesson he instilled as CEO of Twitter and one that he carries with him as he builds his new company's culture from scratch. In this episode, Costolo shares more about his management style, the invaluable experience gained from repeat entrepreneurship and the characteristics that make teams truly great.