From Start-Up to Grown-Up

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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.comConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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!Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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!Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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/5scriptsCheck out Superhuman on https://superhuman.com/You can also follow Rahul on his socials:Twitter | LinkedIn | InstagramConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon

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/5scriptsConnect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon