Becoming a CEO

Matt Blumberg on Storytelling, Crisis Leadership, and the Many Faces of a CEO

What does it really mean to become a CEO? For Matt Blumberg, multi-time CEO, founder, author, and board member, the answer isn’t about titles or authority, it’s about responsibility.  Matt explains that the CEO carries the weight of the entire company, navigating the highest highs and lowest lows, often at the same time. Drawing on decades of experience scaling companies, leading through crises, and mentoring founders, he shares candid lessons on what the CEO role really demands. You’ll hear: * Why great CEOs act as the company’s chief storyteller and ambassador * What Matt learned leading through the dot-com crash, 9/11, and the financial crisis * Why hiring for values is just as important as hiring for competence * How successful companies stay ahead by constantly reinventing themselves * Why writing and publishing content can clarify a leader’s thinking Today, Matt is the CEO of Markup AI, the global leader in AI-powered content governance for enterprises. He also serves as Chairman of Bolster and hosts ‘The Daily Bolster’, a podcast for CEOs and senior leaders. 🌐 Learn more about Matt‘s work: https://startupceo.com/ [https://startupceo.com/] 📘 Order Matt’s book Startup CEO: https://www.amazon.com/Startup-CEO-Scaling-Business-Techstars/dp/1119723663/ [https://www.amazon.com/Startup-CEO-Scaling-Business-Techstars/dp/1119723663/] 🎙️ Listen to The Daily Bolster: https://podcast.bolster.com/public/142/The-Daily-Bolster-29d59cf2 [https://podcast.bolster.com/public/142/The-Daily-Bolster-29d59cf2] 🔗 Connect with Matt on LinkedIn: https://www.linkedin.com/in/blumbergmatt/ [https://www.linkedin.com/in/blumbergmatt/ ] Follow Becoming a CEO for more conversations with founders and CEOs about what it really takes to lead.

Jay Hummel on Succession and Leading with Intention

Why do so many succession plans fail? For Jay Hummel, Co-Founder of Wealth Advisor Growth Network, the answer is rarely about numbers - it’s about leadership. Jay believes leadership is about intentionality: preparing for succession well before it’s needed, building cultures defined by accountability, and having the courage to make decisions when others stall. He also unpacks why emotions often derail leaders more than strategy or finance ever do. You’ll hear: * Why true succession planning starts years before the transition * The difference between hiring harvesters and hiring planters * Why indecision at the top kills momentum everywhere else * How culture is built through clarity and accountability, not perks * Why emotions derail more businesses than financials ever do Jay now advises leaders and firms on growth, succession, and culture, helping them navigate the financial and human side of leadership and transition. 🌐 Learn more about Jay’s work [https://wagn.biz/ ]: https://wagn.biz/ 📘 Order Jay’s book Success and Succession here [https://www.amazon.com/Success-Succession-Unlocking-Potential-Professional/dp/111905852X]: https://www.amazon.com/Success-Succession-Unlocking-Potential-Professional/dp/111905852X 🔗 Connect with Jay on LinkedIn [https://www.linkedin.com/in/jay-hummel/]: https://www.linkedin.com/in/jay-hummel/ Follow Becoming a CEO for more conversations with founders and CEOs about what it really takes to lead.

Eytan Wiener on Grit, Growth, and the Founder-to-CEO Journey

What does it take to grow from hustling founder to seasoned CEO? For Eytan Wiener, co-founder of Quantum Networks and former CEO of GETIDA, the answer is grit, agility, and relationships. Eytan’s leadership journey wasn’t learned from theory. It was built through trial, error, and relentless persistence. From learning the hard way that money isn’t the ultimate motivator, to realizing that business success comes down to people and integrity, he shares candid lessons from scaling, exiting, and starting again. You’ll hear: * Why grit and agility matter more than having the “perfect” plan * How scaling forces leaders to change their role and let go of control * Why relationships and integrity are the real currency in business * What Eytan learned about success after exiting his company * Why he finds more fulfillment in the journey than the destination Eytan now advises and invests in high-growth companies through his new company Potentiate Ventures, helping founders scale, raise, and exit with the benefit of real operator experience. 🌐 Learn more about Eytan’s work [https://www.potentiate.vc/]: https://www.potentiate.vc/ 🔗 Connect with Eytan on LinkedIn [https://www.linkedin.com/in/eytanwiener/]: https://www.linkedin.com/in/eytanwiener/ Follow Becoming a CEO for more conversations with founders and CEOs about what it really takes to lead.

Adam Enbar on Recruiting, Trust, and the Core of Leadership

What separates good CEOs from great ones? For Adam Enbar, co-founder and former CEO of Flatiron School, the answer is simple: it all comes down to people. Adam’s leadership philosophy is built on two principles: hire people who are better than you, and then trust them to do their work. He believes recruiting is the most important job of a CEO - more important than strategy, operations, or fundraising. And once the right people are in place, the CEO’s job is to create an environment where competence and caring drive everything. You’ll hear: * Why recruiting is a CEO’s #1 job * How Adam decided to step back and let his team lead * The two qualities he looks for in every leader * Why communication failures always fall back on the CEO * How luck shaped his journey as much as hard work Adam is an active investor, advisor, and speaker, focused on the intersection of leadership, entrepreneurship, and education.  🔗 Connect with Adam on LinkedIn: https://www.linkedin.com/in/adamenbar/ [https://www.linkedin.com/in/adamenbar/] Follow Becoming a CEO for more conversations with founders and CEOs about what it really takes to lead.

David Siegel on Culture, Kindness, and the Cost of Leadership

What does it really mean to lead at the highest level? For David Siegel, former CEO of Investopedia and Meetup, leadership isn’t about titles or power. It’s about culture, kindness, and carrying the weight of decisions no one else wants to make. In his time leading companies like Meetup and Investopedia, David learned that leadership is less about strategy and more about people. His philosophy - built on culture, kindness, and communication - challenges the idea that CEOs need to be ruthless to succeed. You’ll hear: * Why culture always starts, and ends, with the CEO * The surprising truth about kindness and firing * Why authentic relationships are so rare at the top * How to think about life after the CEO role * Why he regrets not investing more in personal branding David now coaches CEOs and founders, and serves as Chairman of the Israel Tech Mission. He is also the author of Decide and Conquer: 44 Decisions That Will Make or Break All Leaders. 📖 Read David’s article on 'Life Without a Title' in Inc [https://www.inc.com/david-siegel/life-without-a-title/91192739].: https://www.inc.com/david-siegel/life-without-a-title/91192739 📘 Order David’s book 'Decide and Conquer' here [https://www.amazon.com/Decide-Conquer-Decisions-Break-Leaders/dp/140023087X]: https://www.amazon.com/Decide-Conquer-Decisions-Break-Leaders/dp/140023087X 💻 Book time with David [https://intro.co/DavidSiegel?source=intro]: https://intro.co/DavidSiegel?source=intro 🔗 Connect with David on LinkedIn [https://www.linkedin.com/in/davidmsiegel/]: https://www.linkedin.com/in/davidmsiegel/ Follow Becoming a CEO for more conversations with founders and CEOs about what it really takes to lead.