Colin Bryar, a former top executive at Amazon and co-author of 'Working Backwards,' shares invaluable insights from his time shadowing Jeff Bezos. He discusses how Amazon's unique six-page memo process transforms communication and decision-making. Colin highlights the importance of customer obsession and long-term thinking in the company's culture, offering gems about how resilience and mental well-being factor into leadership. He also details the intricate hiring processes that uphold Amazon's high standards, providing practical advice for startups looking to adopt similar frameworks.

David Heinemeier Hansson, the mind behind Ruby on Rails and co-owner of 37signals, shares his unconventional management philosophies and innovative journey. He advocates for starting from first principles and adapting strategies for smaller organizations. The discussion delves into the benefits and challenges of remote work, and how clarity in policies like unlimited vacation can enhance employee satisfaction. Hansson emphasizes the importance of bold decision-making as founders, encouraging a mindset that embraces change and values real-world feedback.

Shegun Otulana, founder and CEO of Harmony Venture Labs, is a successful entrepreneur who bootstrapped his way from Nigeria to building a $1.25 billion healthcare tech company. He discusses how constraints can drive growth and the importance of vulnerability in leadership. Shegun shares insights on maintaining company culture in remote settings, the emotional journey of entrepreneurship, and the impact of education on empowering communities. His reflections on overcoming imposter syndrome and the significance of nurturing local startups make this conversation inspiring and enlightening.

Jake Schwartz is a serial entrepreneur, investor and advisor. Until 2020, Jake Schwartz served at CEO of General Assembly (GA), the global leader in education and career transformation, which he co-founded in 2011. He grew GA to over 1,000 employees on five continents. In 2018, GA was acquired by The Adecco Group. Jake Schwartz co-founded and serves as Chair of Brave Health, a mission-driven company focused on expanding access to high-quality, affordable care for mental health and addiction. Jake Schwartz was named E&Y Entrepreneur of the Year in 2014 and one of Crain’s “40 under 40” in 2015. Jake holds a BA from Yale and an MBA from The Wharton School of Business at the University of Pennsylvania. He is a former CFA Charterholder.When you hear the founding story of any startup, it can often feel like it was destined.That the end was clear at the beginning and the founders held an unwavering gaze.We often think launching a successful company requires:Defining roles from day oneHolding to an unchanging visionWork through a clear path to get there.That's one way to do it!But what if there's another approach?What if building a successful startup isn't about following a strict formula, but about embracing serendipity and intuition?Jake Schwartz, Co-Founder and former CEO of General Assembly, didn't have a conventional playbook. Looking back a decade later, he felt like they were forming a band.Just get together, start creating, figuring things out as you go.What I took away from this discussion:Passion > perfect plan. Flexibility > rigidity early on. Evolution > clear vision.By following their intuition and leaning into serendipity, Jake and his co-founders discovered a unique formula for success.Learn more about Jake and Brave Health | Websitehttps://bebravehealth.com/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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Jake Kloberdanz is the founder of ONEHOPE, a pioneering wine brand with a mission to create a positive social impact. Under his leadership, ONEHOPE has donated tens of millions of dollars to over 40,000 non-profits and grown from zero to producing over one million bottles per year. The company boasts a world-class vineyard in Napa Valley and has garnered more than 30 wines with 90+ point ratings. Recognized as one of the fastest-growing private companies by Inc. Magazine, ONEHOPE has raised over $100 million in funding. Jake has been honored as a "Top 40 Under 40" by Wine Enthusiast and a "Top 30 Under 30" by Forbes. He serves on the boards of 8VC and After the Fire, and is a sought-after speaker, having presented at the UN Global Summit, TED, and leading universities like Stanford and MIT. A graduate of UC Berkeley's Haas School of Business and a two-time national rugby champion, Jake is an advocate for "Cause-centric Commerce," integrating purpose into business models.This new episode of From Start-Up to Grown-Up features an in-depth conversation with Jake Kloberdanz, the Co-Founder and CEO of One Hope Winery, who’s reshaping how business and philanthropy intersect. From selling wines out of a U-Haul to building a company that’s donated over $10 million to meaningful causes, Jake's story is nothing short of inspiring.Jake talks about his original idea to create “Girl Scout Cookies for adults” and how that evolved over time. He also talks about his evolution as a leader as the company overcame turbulence, how he learned the importance of clarity and how he developed his frameworks for communication. Learn more about One Hope Winery | Websitehttps://www.onehopewine.com/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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Susan McPherson, founder and CEO of McPherson Strategies, is a seasoned connector and angel investor with over 30 years in corporate responsibility. She shares her wisdom on the importance of reigniting dormant ties and the long-term benefits of networking. Susan discusses overcoming outreach fears and emphasizes that proactive networking, such as hosting events, can transform relationships. With practical tips and personal anecdotes, she encourages a selfless, empathetic approach to building connections that empower others.

Jeff Shiner, CEO of 1Password, shares his journey from leading a 20-person team to a $6.8 billion global entity. He dives into the importance of earning respect as a new leader and the challenges of hiring during rapid growth. Shiner discusses the art of bootstrapping and strategic fundraising, emphasizing customer needs over external investment. He opens up about personal growth and the loneliness of leadership, while also finding joy in managing a farm and restoring a tractor – showing how he balances work and personal fulfillment.

Seth Godin, an influential entrepreneur and best-selling author, discusses his journey from career challenges to significant life awakenings. He reflects on how a near-death experience reshaped his views on creativity and relationships. The conversation delves into seeking personal significance over conventional success, emphasizing empathy and authenticity in leadership. Seth also shares insights on embracing creativity, facing rejection, and the importance of feedback in fostering a supportive work culture.

David is Nash Squared's Group Technology Evangelist. He crafts podcasts, hosts video debates, speaks, moderates conferences, and chairs keynote stages. He's a passionate advocate for technology, dissecting its challenges and opportunities. David has worked at Nash Squared since 2007, where he has developed a deep understanding of the technology and talent markets. Recognised as Computing's Digital Ambassador of the Year (2018), he brings a wealth of experience and knowledge to every conversation. Since 2015 he has been editor and host of Tech Talks, a show about leadership and technology currently ranked as one of the most popular podcasts in the world.David Savage is this episode's guest, who reinforces why it’s so important to realize that trusting ourselves is a skill. And like all skills it can be developed! In addition to learning about trusting yourself, you’ll also hear from David how to become an “intrapreneur,” the importance of establishing consistent behavior, and how that applies to strengthening our personal branding.Learn more about David and Tech Talks | Website https://www.nashsquared.com/techtalksConnect 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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!

Kim Scott is the author of Radical Respect and Radical Candor. Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google.Being able to hold a candid and caring conversation with someone is an essential part of leadership.  My next guest on From Start-Up to Grown-Up is Kim Scott, bestselling author of Radical Candor and her new book, Radical Respect.Kim delivers a masterclass in building respect and kindness as the foundation of a company’s DNA with several strategies you’re going to want to use immediately.You’ll learn how to create an environment where employees feel safe. You’ll also learn that empowering yourself and your employees to challenge openly and diplomatically can lead to building a successful company.Learn more about Kim | Websitekimmalonescott.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 AmazonLove the show? Subscribe, Rate, Review, Like, and Share!