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The Daily Bolster

Latest episodes

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Jun 12, 2023 • 6min

Taking On the Role of CEO from a Founder with David Rosenblatt

Can you gracefully take over the CEO role from a founder? David Rosenblatt is the CEO of 1st Dibs, where he joined the team, took over the role of CEO, and scaled the company. Tune in as he joins the podcast to share his thoughts on making the transition strategically, understanding company culture, and addressing disagreements.
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Jun 9, 2023 • 31min

Deep Dive with Max Yoder

Today, we’re diving deep with Max Yoder, founder of Lessonly. Max shares his experience as a young professional with an unusual career trajectory and what it was like moving straight into the founder role. He and Matt also talk about emotional liberation, receiving feedback, learning to be a CEO, and how his love of music helped him find harmony. Tune in for a great episode packed with insights on the founder journey and self-reflection.
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Jun 8, 2023 • 8min

Lessons Learned from Selling a Business with Mindy Lauck

Today’s guest is the former CEO of Broadly, which was recently acquired. Mindy Lauck joins us to share what she learned through the acquisition process, and what she wishes she’d known ahead of time. One of our biggest takeaways? Be ready to recalibrate your expectations. There will be delays, you’ll essentially be working two jobs as a CEO and a process leader, and decisions will be more complex. It’s important to be flexible. Tune in to hear Mindy’s thoughts and advice for walking through an acquisition as a CEO. 
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Jun 7, 2023 • 5min

How CEOs Can Get the Most From CXOs with Sarah E. Brown

Today on the podcast, we’re talking about how CEOs can get the best results from their leadership teams. Our guest, Sarah E. Brown, is the VP of Marketing at Sastrify. She’s also an author, startup mentor, and ecosystem builder. Her new book is called Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams (Wiley, 2022).
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Jun 6, 2023 • 4min

Deciding if Entrepreneurship is Right for You with Allie Egan

Some people aren’t founders, but they should be—and some people are founders, but shouldn’t be. Today, we’re sharing three questions you can ask yourself to determine whether entrepreneurship is the right path for you. Our guest, Allie Egan, is the founder and CEO of Veracity. Tune in to hear about her experience as a founder and what she believes is most important to consider before taking the jump. 
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Jun 5, 2023 • 6min

Strategies for Nurturing Alignment with Clare Hart

Clare Hart, CEO of Williams Lea, has a reputation for being a uniquely methodical leader. Today, she’s sharing strategies that help her keep her team aligned. Her first piece of advice? It’s important to establish a cadence of repetitive and transparent communication with your employees. Tune in to the episode to hear all four tips.
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Jun 2, 2023 • 35min

Deep Dive with Greg Sands

Today on the podcast, Matt is joined by Greg Sands, founder of Costanoa Ventures. Tune in as they dive into Greg’s career, starting at Netscape in 1994 during the dawn of the commercial internet, to getting into venture capital and the unique process of founding Costanoa. Matt and Greg also chat about extraordinary moments in the tech industry, empathy for founders, and what it means to run a healthy organization. Listen now!
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Jun 1, 2023 • 5min

Learning About Yourself While Growing a Business with Max Yoder

Today on The Daily Bolster, former Lessonly CEO Max Yoder shares what he learned about himself through the scaling process. One of our favorite takeaways? Conflict isn’t dysfunction, it’s information. 
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May 31, 2023 • 5min

How to Improve Your Board Meetings with Robert Wolfe

CEOs have an opportunity to make their boards more effective. How? Check out today’s episode to learn about snackable board books and more. Robert Wolfe—a successful multi-time founder—is the CEO of Zeck, where his team is reimagining the approach to board decks, board prep, and board governance. Board meetings don’t have to be miserable.
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May 30, 2023 • 7min

Interacting with the Board as a CXO with Cristina Miller

Expect the unexpected. From first communication to preparing to join a board meeting to sitting down for dinner with directors, Cristina Miller of Goldbelly shares her experience interacting with boards as a COO. Her final piece of advice? Don’t expect the board meetings to go as planned, but remember your day job has likely prepared you for those unexpected moments. 

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