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Alexi Robichaux is the Co-Founder and CEO of BetterUp, the first leadership development platform to connect coaching to sustainable behavior change. Prior to BetterUp, Alexi was Director of Product Management at VMware. Alexi is Chairman of Youth Leadership America (YLA), a nonprofit he co-founded in 2003, to foster peer-to-peer leadership development and civic engagement in high school students. YLA has collaborated with leading companies including Disney, Google, and Hilton Hotels to coach and mentor future leaders.This episode is chock-full of so many stories! We literally dive right into it, talking about what Navy Seals taught him about running his company, handling a cacophony of pain and misery, why it took him two years to hire a CRO, the frameworks he has in place to scale his business, and the mentors who have helped him learn them.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!If you like what you hear, please subscribe to the podcast!Learn more about BetterUpFor more stories and advice on founders and CEOs, head to alisacohn.com
Oleg Rogynskyy is the Founder and CEO of People.aiI was introduced to Oleg by Robin Matlock, who has also appeared on this podcast! Oleg is an incredibly thoughtful and intentional leader in how he builds his company. In our conversation, we talk about specifics for board management,  why he hires people that are "way out of his league," and his strategy to maintain and grow his extensive network.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!If you like what you hear, please subscribe to the podcast!Learn more about People.aiFor more stories and advice on founders and CEOs, head to alisacohn.com
Episode 19 - Jon Stein

Episode 19 - Jon Stein

2022-05-0901:06:16

Jon Stein is the Founder and Chairman of the Board at Betterment.Jon was the first person I interviewed for my book, From Start-Up to Grown-Up! We start at the beginning of his journey that led him to founding Betterment, then discuss how important culture is to the success of the company. Later on, we got into why he stepped down as CEO, and how he would end up finding his successor.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!If you like what you hear, please subscribe to the podcast!Learn more about Jon's company, Betterment, at betterment.comFor more stories and advice on founders and CEOs, head to alisacohn.com
Episode 18 - Paul English

Episode 18 - Paul English

2022-04-2501:11:39

Paul English is the co-founder and CEO of Boston Venture Studio,Paul has been a founder for multiple companies and organizations, one of his companies being Kayak. Paul shares how he found his co-founder Steve Hafner and how they decided to build Kayak together. He is also a master of the hiring process, and shares step by step his process for determining whether to hire someone and how he does it within seven days of hearing their name!To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!If you like what you hear, please subscribe to the podcast!Learn more about Paul at paulenglish.comFor more stories and advice on founders and CEOs, head to alisacohn.com
Episode 17 - Kara Goldin

Episode 17 - Kara Goldin

2022-04-1201:04:49

Kara Goldin is the co-founder and CEO of the beverage company Hint Inc.She discusses co-founding Hint with her husband Theo, why and when she decided to bring in outside investors after bootstrapping for so long, and why singer-songwriter John Legend became an investor.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!If you like what you hear, please subscribe to the podcast!Learn more about Hint at drinkhint.comFor more stories and advice on founders and CEOs, head to alisacohn.com
Episode 16 - Julien Smith

Episode 16 - Julien Smith

2022-03-2801:06:11

Julien Smith is the Founder and CEO of Practice, a WSJ bestselling author, and former CEO and Founder of Breather.He discusses what he learned stepping away from his former company, Breather, how he strengthens his co-founder relationships, and the insight he gained watching another CEO operate.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!Learn more about Practice at practice.doFor more stories and advice on founders and CEOs, head to alisacohn.com
Episode 15 - Ilan Twig

Episode 15 - Ilan Twig

2022-03-1701:04:05

Ilan Twig is the Co-Founder and CTO of TripActions.Ilan talks about how his first company was acquired after nine months, how the pandemic nearly ruined their business, how they leaned on their mission and culture to create and survive, and why a diagnosis helped define his leadership style.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!Learn more about TripActions at tripactions.comFor more stories and advice on founders and CEOs, head to alisacohn.com
Sid Viswanathan is the Co-Founder and President of the digital health platform, Truepill.This was such a rich conversation! We talked about how he was reverse-pitched on his first startup, founder market fit, how company culture evolves as your business grows, and how when he solves a problem, it's a failure.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!
Ragy Thomas is the Founder and CEO of the social media and customer management company, Sprinklr.We really got into it in this discussion, from how he grew up in a family that looked down on business, becoming a multi-time entrepreneur, his abundance mindset, and the advice that changed his life.To stay up to date on future episodes and learn more from Alisa, sign up for her newsletter!
Episode 12 - Rahul Vohra

Episode 12 - Rahul Vohra

2022-01-1001:04:06

Rahul Vohra is the Co-Founder and CEO of Superhuman.Rahul Vohra is the Founder and CEO at Superhuman. According to Crunch Base, he is also a Technical Advisor at Boldstart Ventures, an investor and advisor at Partender, and an investor of sendwithus and Easy Post. He received his bachelor of arts in Computer Science at the University of Cambridge.Rahul shares the lessons he learned from being a serial entrepreneur, how and why he learned to meditate, what he does to build trust with his team, and the pros and cons of being a celebrity founder.[1:41] Rahul’s Gaming Life[3:57] Rahul’s Past Experiences[6:48] Rahul’s Experience on Rapportive[8:07] Motivation and Driving Power of Rahul[11:25] Maintaining Spiritual, Mental, and Physical Health[26:06] Taking Feedbacks[31:56] Building up Trust[38:29] Change of Mindset as a Leader[44:12] Is there a Downside about Waiting so Long to Launch?[51:52] The Challenges of Change[56:11] Advantages and Disadvantages of Being a Celebrity CEO[59:55] Experience on Self-Doubt[1:02:50] Advice in Growing as a LeaderTo stay up to date on future episodes and learn more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Robin Matlock was the former CMO of VMware, an independent Board Director of startups including People.ai and Cohesity.Robin is a seasoned Silicon Valley GTM executive with over 30 years of marketing, sales and business development experience in the enterprise software and services market. Currently an Independent Director with Iron Mountain (NYSM: IRM), serving on Technology, Compensation and Risk/Safety Committees. Advisor to People.ai, a fast growing AI and Revenue Acceleration company, and Calamu, an early-stage disruptor in the data security market.She talks about her own career growth and about the importance of not putting limits on yourself and how a fateful lunch totally changed her career trajectory. She talks about how you need to promote yourself in your own mind to lead at a different altitude as you become more senior, and then again when you serve as a board director. Robin also shares a recipe for how to bring culture to life, why you need to get better at failing, and how playing the harp prepared her for her very successful business career.[01:58] Silicon Valley’s Ethos[03:54] Robin’s role model[08:38] A CEO’s Influence[15:41] How Robin’s career began[36:36] The Importance of Culture[46:16] Struggles[52:48] AdviceTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 10 - Greg Galant

Episode 10 - Greg Galant

2021-12-2001:09:35

Gregory Galant is the co-founder and CEO of Muck Rack, a platform enabling PR teams to work together to find the right journalists for their stories, send customized pitches, build meaningful relationships with the media, monitor news and quantify their impact. It’s used by thousands of organizations, including Taco Bell, Pfizer, Golin, International Committee of the Red Cross, Knight Foundation, Kauffman Foundation and Penguin Random House. Muck Rack is also the solution of choice for journalists, who use Muck Rack’s free, automatically updated portfolios to showcase their work and provide information about what stories they’re looking for.Greg’s also the co-creator and executive producer of The Shorty Awards, which honor the best of social media. Past winners include Lizzo, Ricky Gervais, Rebel Wilson, Trevor Noah, Conan O’Brien, Issa Rae, Marques Brownlee, Sesame Street, Neil Patrick Harris, Mike Bloomberg and NASA.Greg is a frequent speaker and writer on topics related to social media, marketing, PR, entrepreneurship, remote work and journalism. He’s presented at SXSW, Web Summit, Harvard Business School, Le Web and The International Journalism Festival, and his columns have appeared in Fortune, Forbes and Business Insider.Along with his companies, Greg has been cited in and interviewed by numerous media outlets, including The New York Times, The Wall Street Journal, The Associated Press, Business News Daily, Editor & Publisher, Entrepreneur, Fast Company, Inc., Poynter, PR News and PRWeek. BusinessWeek named him one of the “Best Young Tech Entrepreneurs,” and Crain’s honored Muck Rack as one of the “100 Best Places to Work in New York City.”In this episode, Greg shares why he decided to bootstrap instead of taking VC money, the constant state of change his job is as a CEO, and why he’s become grateful to sit around and be bored.[1:33] Early Days of Greg's Entrepreneurial Career[3:22] Greg's Founding Story[11:04] Greg's View on Failure[15:45] Greg's Opinions on VC Money[19:39] Downsides on the Decisions Made[24:38] Greg's Journey as a Leader[33:00] What Greg Felt When He Gave Way [40:13] Setting Learning Goals[42:27] Working Remotely – The Remote Culture[52:22] Greg on Firing People[57:56] Self-doubt in Greg's Entrepreneurial Journey[1:07:42] Final RemarksTo hear more from Alisa, sign up for her newsletter at alisacohn.com/5scripts
Episode 9 - David Sax

Episode 9 - David Sax

2021-12-0851:08

David Sax is the author of The Soul of an Entrepreneur.An award winning writer, journalist, and keynote speaker, David has been at the forefront of reporting and dissecting the intersection of business and culture for nearly two decades, including four internationally bestselling books, articles and appearances in nearly every major global news outlet, and dozens of keynote speeches to audiences around the world.We talk through the startup myth, what entrepreneurship really looks like, the emotional and personal journey about what it takes to be an entrepreneur, and the highs and lows of being a solopreneur.[0:48] Going Beyond the Start-Up Myth[3:30] David’s Interest in Entrepreneurship[9:23] Accidental Entrepreneurs[15:56] What does it take to be an Entrepreneur?[22:49] Occupational Hazard on Entrepreneur[25:39] David as a Solopreneur[28:55] David’s reminder during downs[37:58] Is Entrepreneurship a Mental Illness?[41:07] The Change after Writing the Book[44:40] What David is Working on for NowTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 8 - Rick Nucci

Episode 8 - Rick Nucci

2021-11-3048:54

Rick Nucci is the Co-Founder and CEO of Guru.Rick Nucci is co-founder and CEO at Guru. Rick brings twenty years of experience in creating category-leading software solutions and companies. Prior to Guru, Rick was the founder and chief technology officer of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was acquired by Dell in 2010, where Rick went on to run the Boomi business for Dell as its general manager, helping grow the organization into the industry leader it is today. Rick frequently speaks at industry events about startups, SaaS and cloud computing. Rick holds a Bachelor of Science in Logistics, Materials, and Supply Chain Management from Penn State University.In this talk, Rick discusses the importance of having complementary founder skills, his philosophy about culture, what to do when he doesn't know what to do, and why he insists that people vent.[01:04] “Success is not a license for arrogance.”[02:55] What Rick learned from the trials and errors of leadership[15:03] Importance of Culture [19:42] Hiring Candidates [22:09] Downsides to Guru’s Culture [28:02] Maintaining Guru’s Culture during the Pandemic[34:19] The Change and Growth that Ricks has done as a Leader [40:30] Experiencing Self-Doubt and Impostor Syndrome [45:46] What Rick wished he knew before starting his journeyTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Jennifer Dulski is the Founder and CEO of Rising Team and author of the WSJ bestselling book Purposeful.Jennifer Dulski has a wide range of executive experience including leadership roles at Facebook, Google, and Yahoo!, and founder, CEO, and president roles at early stage and scaling startups. She is currently CEO and founder of Rising Team, a company that provides tools, data, and community to turn managers into amazing coaches that build happier and more successful teams.Prior to Rising Team, she led Facebook Groups, used by more than 1.5 billion people each month to create and participate in communities that matter to them. Her team was responsible for envisioning, building, and growing the Groups product. She also led the 2019 redesign of Facebook, “FB5,” to put communities at the center of the app.Before Facebook, Dulski was president and COO of Change.org, a social enterprise company that empowers people to create campaigns for change. Under her leadership, Change.org grew 10x, from 18 million users to 180 million, developed a profitable business model, rebuilt its tech stack, and supported thousands of successful campaigns globally.During our conversation, Jennifer shares her story of becoming the founder of a nonprofit when she was 21, how you can get fooled by thinking you have product market fit, why it's so helpful for founders to spend time at large companies, work/life mashup, and her love of acronyms.[01:49] Overcoming Challenges[03:20] Strengthening Teams with Similar Talents[05:30] Why Jennifer Appreciates Honest Feedback[08:45] Building a Nonprofit Company[10:03] Structure of the Organization[14:23] Developing Technology to Create a Consumer Product[17:53] Truths of Being a Serial Founder[26:12] Jennifer's Goal to Build Rising Team[37:25] Vital Life Lessons Learned[42:55] The Strength of Self-Confidence[49:55] Three Traits for Successful MovementsTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 6 - Jeff Wald

Episode 6 - Jeff Wald

2021-11-1501:10:08

Jeff Wald is a serial entrepreneur,  Board Member, Best Selling author, Keynote speaker and investor.   Jeff is co-founder and Chairman of two new technology startups, Bento Engine (toolkit for financial advisers) and Sonero (AI tool that provides summaries and action items from meetings).  Jeff’s previous company, Work Market, an enterprise software platform that enables companies to manage freelancers was acquired by ADP in 2018, where he served on the Senior Leadership Team until 2020.  Mr. Wald has founded several other technology companies, including Spinback, a social sharing platform (eventually purchased by salesforce.com). He began his career in finance, serving as Managing Director at activist hedge fund Barington Capital Group, a Vice President at venture capital firm GlenRock and various roles in the M&A Group at JP Morgan.Jeff has served on numerous public and private Boards of Directors including Steel Connect (NASDAQ: STCN), Costar Technologies (OTC: CSTI) and venture-backed TransfrVR.   Mr. Wald serves as an adviser to several companies and entities including the X-Prize’s Rapid Reskilling Initiative.Jeff is the author of the #1 Amazon Best Seller, The End of Jobs: The Rise of On-Demand Workers and Agile Corporations and The Birthday Rules: A Fun and Flexible Framework for Raising Children in a Technology Enabled World.In this episode, Jeff talks about cofounder drama, his depression when his first startup failed, and what he said to his investors when they told him to get a coach, frameworks, and what he now looks for as an investor.[02:48] How Jeff started[13:44] Sign of Weakness[20:37] Getting a Coach [27:33] Working Habit[37:28] Lifeline[45:05] Achievements[47:28] Jeff’s Imposter Syndrome[55:23] Advice[01:07:57] ConclusionTo hear more from Alisa, sign up for her newsletter at alisacohn.com/5scripts
Sadie Lincoln is the co-founder and CEO of the fitness franchise company, Barre3. Sadie is on Inc.’s Female Founders 100 list and the MO100 Impact list, has been featured on NPR’s How I Built This, and speaks regularly on the topics of mindful leadership, the power of body wisdom, and the movement to redefine what success in fitness means. Beyond running her company and being a global spokesperson, Sadie still enjoys teaching barre3 classes to many of her founding clients in her hometown of Portland, Oregon.In this episode, Sadie shares how their in-person business had to pivot during the pandemic, why she views running her business as a spiritual practice, the worst feedback she ever received, and the importance of having the right team around her.[2:17] Building business was a spiritual practice[5:14] Micro practices that bring her closer to her spiritual practices[7:46] Shifting into a more confident state[9:45] The founding story of Barre3[16:39] During the pandemic[33:26] A circle in Sadie’s leadership group[37:41] Female leadership[39:55] What else does Sadie wish she had known earlier on her journey?[41:04] Sadie’s AdviceTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 4 - Chris Hsu

Episode 4 - Chris Hsu

2021-11-0101:02:24

Chris Hsu is the CEO & Co-Founder of Azibo, a VC-backed real estate fintech startup focused on simplifying the rental property experience. Prior to Azibo, Chris served as an Advisory Partner at a16z and previously was CEO of Micro Focus, a $4B enterprise software company. He also was COO of Hewlett Packard Enterprise, where he successfully led the largest corporate separation in history. Chris spent the earlier part of his career in leadership roles at top consulting firms, including KKR and McKinsey. A military veteran, Chris graduated as a Distinguished Cadet from the United States Military Academy at West Point and completed his U.S. Army tenure as a Captain. He also has an MBA from Northwestern’s Kellogg School of Management.In this episode of From Start Up to Grown Up, our guest is Chris Hsu. Chris is the CEO and Co-Founder of Azibo, a financial service for rental property owners. He has various work experience with a variety of companies, namely: General Mills, McKinsey, KKR, HP, and Andreessen Horowitz. He also has an MBA from Kellogg School of Management.In this episode, we cover:[1:59] Chris’ Personal Life[7:33] Chris’ Experience on Ranger School[13:55] Azibo Founding Story [18:17] Co-Founding Azibo[22:02] Culture of the Company that Chris wrote down[33:40] Chris on Leadership [37:43]The Struggles of Chris in his journey[46:44] Chris as a CEO [54:09] Challenges in Talking to Employees and Executives[59:48] What Chris Wished He Had Known Earlier[1:02:02] Advice for other FoundersTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 3 - Jake Stein

Episode 3 - Jake Stein

2021-10-1901:01:27

Jake Stein is the cofounder and CEO of Common Paper. Previously, he was the co-founder of RJMetrics (acquired by Magento, then Adobe) and Stitch (acquired by Talend). Before RJMetrics, Jake worked in venture capital, started a landscaping business in high school, and was the 44th ranked table tennis player under 21 in New Jersey; achievements of which he is equally proud.In this episode, Jake discusses the pros and cons of distributed teams, the questions that he and his co-founder asked before they started their company, and the challenges he ran into once his former company was acquired. You'll also hear Jake's biggest mistake, how he invites company feedback parties, and all about Whale Wednesdays.[01:27] Entrepreneurship Origins[03:32] Aligning Company Plans[11:33] The Emotional Battle of Running a Business[28:03] Written Feedback vs. Verbal Feedback[33:23] Fostering Company Culture[45:36] Jake’s Biggest Professional Blunder[58:05] The Importance of Self-Care[58:51] Advice for New Business OwnersTo hear more from Alisa, sign up for her newsletter at http://alisacohn.com/5scripts
Episode 2 - Zvi Band

Episode 2 - Zvi Band

2021-10-1501:04:00

Zvi Band is the co-founder and CEO of Contactually, which has been acquired by Compass. He is also the author of Success is In Your Sphere. His new venture is called Talk Social, which is focused on bringing humanity back together.In this episode, Zvi and I had a conversation about how he got onto the path of entrepreneurship, how he learned to see himself as the leader, and the limits of transparency. Zvi and I also get into a real talk discussion about co-founder dynamics, mental health, and his surprising advice to founders who are getting ready to sell their business.To hear more from Alisa, sign up for her newsletter!
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