Today’s guest is Sherisse Hawkins, Founder and CEO of Pagedip. An engineer and technologist by degree, she got her start as a Disney Imagineer, designing theme parks around the world. Now, though, she considers herself a “corporate escapee,” driven by a love of starting new things and solving new problems.Sherisse and Matt are diving deep into her journey from corporate life to startup CEO. They talk about pivoting to find product market fit, finding balance and sustainability as a leader, and what makes becoming a CEO a compelling move.

Joining Matt on today’s Ask Bolster episode is Louis Bucciarelli, CEO of Playvox. His question comes after the SVB collapse and in the midst of unpredictable markets: how should a leader go about planning during uncertain circumstances? How can CEOs react to current events without overcorrecting or lagging behind?He and Matt discuss creating flexibility through an ongoing planning process, asking for help, and more.

As a Partner at The Venture Collective, Cat Middleton sees hundreds of pitches a year. Today on The Daily Bolster, she shares three things founders can do to stand out and earn an investment.  Curious if your startup is a fit for The Venture Collective? Stay till the end (a whole 6 minutes) for a big picture glimpse of their goal: investing in companies that are making the world a better place.

What’s on your to-don’t list? Fran Hauser is a bestselling author, keynote speaker, startup investor, and former c-suite exec. Today, she and Matt are chatting about her advice for CEOs experiencing overwhelm. Listen for tips on staying aligned with your priorities, using boundaries to create space in your day, and our new favorite tool: the to-don’t list.

Your customers are telling you something everyday, if you’re smart enough to listen. Lee Mayer is the Co-Founder and CEO of interior design start-up Havenly, where she creates delightful experiences around home shopping and design. Today, she’s sharing three tips for staying up to date on consumer trends, especially in a fast moving B2C environment.

Today’s guest is Nick Mehta, CEO of Gainsight. He and Matt are diving deep into Nick’s journey launching and scaling Gainsight to 1200 employees over 10 years. Nick considers himself a student of the craft of being a CEO—something that gives him an interesting and thoughtful perspective. They also talk about being values-based from the beginning, keys to a healthy board, the stages of building a leadership team, and why careers are like jungle gyms.

Joining Matt on today’s Ask Bolster episode is Sam Alexander, the often relentless and always over caffeinated CEO and co-founder of bitewell. As a seed stage business closing a round of fundraising, they’re beginning to think about board construction. Sam’s question for Matt: How should early stage founders approach building their boards? Matt shares his rule of 1s, the importance of independent directors, and how to engage and compensate your directors.

Before starting Red Bike Capital, Rachel ten Brick spent 15 years building billion-dollar brands. She co-founded a Y Combinator backed startup called Scentbird, and made the transition to the investor side more recently. Rachel is sharing three learnings from her transition from operator to investor. This episode is a great listen for operators looking for a window into the world and perspective of VCs.

Marc Maltz has coached hundreds of CEOs over his career. Today, he and Matt discuss strong leadership and the importance of empathy. They also cover the role of purpose within organizations, how it can lead to resilience, and how the lack of it can—in some cases—lead to chaos.

Co-founding a company is a major commitment—not only to a company, but to another person (or people). Bolster has eight co-founders, so we know all too well the challenge of bringing multiple individuals together to accomplish one goal. Today on the podcast, Sherisse Hawkins, founder and CEO of Pagedip, talks about co-founding a company with a virtual stranger and how they began their unique method of exchanging regular feedback—both positive and negative. This feedback loop, she says, is what made her and her co-founder unstoppable.