Eddie Kim, Co-founder and CTO of Gusto, shares his inspiring journey of building a platform for small businesses. He discusses the nuances of co-founder dynamics and the importance of communication in leadership. Eddie reveals how he transitioned from a technical role to a leader, embracing a hands-off approach to enable his team. He also addresses the unique challenges faced by Asian founders and emphasizes a growth mindset. Bonding traditions among co-founders showcase how friendship fosters stronger professional relationships.

In this episode of From Start-Up to Grown-Up, host Alisa Cohn sits down with Daniel Yanisse, co-founder and CEO of Checkr, to discuss the exhilarating rise and the challenges of sustaining a high-growth company. Checkr revolutionized the background check industry, scaling from a $1M revenue run rate in just three months to processing millions of background checks annually. But with hypergrowth came intense operational, cultural, and leadership challenges.Daniel shares how he navigated:Hiring at hyperspeed—and why some employees quit on day one.The "hangover" after hypergrowth—losing key executives and investor pressure.How to hire and retain top executives—and avoid common leadership hiring mistakes.Revising a company mission to balance fairness and safety while scaling.The "Fly High, Fly Low" leadership approach—balancing strategy and deep operational insights.This episode is packed with real-world lessons for founders, CEOs, and startup leaders facing the challenges of rapid growth, leadership transitions, and market shifts.🎧 Listen now and learn how to build and sustain a high-growth company. Timestamps & Key Topics00:00 – Introduction02:30 – The Early Days of Checkr06:20 – The Downside of Hypergrowth08:45 – Facing Leadership Challenges & Executive Turnover15:30 – Hiring and Managing Executives21:00 – Redefining Checkr’s Mission: Fairness vs. Safety28:00 – Leadership Lessons & Overcoming Challenges39:00 – Confidence, Imposter Syndrome & Founder Loneliness45:00 – Final Advice for FoundersConnect 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

Dr. Peter Attia, founder of Early Medical and host of The Drive, dives deep into the interplay of health and wealth. He explores how daily habits can significantly boost longevity and healthspan. Attia discusses the evolution from Medicine 2.0 to 3.0, advocating for a new paradigm to tackle chronic illnesses. He highlights the concept of the 'centenarian decathlon,' encouraging fitness goals for maintaining capabilities as we age. Additionally, he addresses mental health challenges in entrepreneurship, emphasizing the need for compassion and timely intervention.

Isabelle Freidheim, founder of Athena Capital and the youngest chairman of a publicly traded company in the U.S., shares her inspiring journey. She discusses the unique challenges women face in finance and the importance of creating opportunities through SPACs. Freidheim emphasizes the benefits of empowering women in leadership roles and shares personal anecdotes of overcoming self-doubt. Her early entrepreneurial experiences shaped her innovative approach to investment, highlighting the value of resilience and collaboration in building successful, women-led teams.

Ethan Evans, former Amazon VP and executive mentor, shares his extensive experience in helping leaders level up their careers. He discusses the importance of self-promotion and strategic relationships in navigating managerial roles. Listeners learn to tackle career challenges by seeing them as puzzles, and Ethan emphasizes the value of mentorship in professional growth. He also addresses overcoming imposter syndrome and highlights the role of self-confidence in fostering career success, encouraging everyone to embrace their unique journey.

Chip Conley, founder of the Modern Elder Academy, offers rich insights as a leading voice at the intersection of psychology and business. He shares how to turn regret into future fuel and the necessity for founders to embrace identity shifts. Chip also discusses strategies for managing older team members and reflects on vital lessons learned from mentorship. Plus, he reveals his favorite interview question that uncovers deeper cultural fits—proof that wisdom truly transcends age in the workplace!

Gary Vaynerchuk, also known as "GaryVee," is a serial entrepreneur, the Chairman of VaynerX, and 5x New York Times Best Selling Author. He is a leading global mind on what's next in culture, relevance, and the internet. Gary possesses an uncanny ability to recognize trends and patterns early to help others understand how these shifts impact consumer behavior. He is one of the most forward-thinkers in business. Gary's approach sits at the intersection of business and culture. He keenly understands how to bring brand relevance to the forefront. “It's not a hokey thing to say you have to enjoy the journey. It's the only sustainable thing.” That’s one of the wisdom bombs from my latest guest on From Start-up to Grown-up, the legendary  Gary Vaynerchuk- Chairman of Vayner X and the author of his brand new book, Day Trading Attention.Here are a few more of the many great takeaways Gary offered during our discussion:“Chasing the short-term is the number one strategy that makes people fail.”“Entrepreneurship is a constant game of losing with occasional wins.”“There’s nothing that happens on earth that doesn’t start with attention.”Learn more about his book, Day Trading Attention | Website garyvaynerchuk.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

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.