Today, we’re going in depth with bestselling author, keynote speaker, startup investor, and former c-suite executive Fran Hauser. She and Matt dive into her career journey, from keeping the books for her dad’s business in crayon all the way to venture capital. In this episode, Fran shares her passion for helping leaders reflect on their careers and make space for more of what brings them joy. She also talks about the journey to loving her own career, leveling the playing field for women, and the advice she’d give her younger self.

Dan Shapiro joins Matt Blumberg on this Ask Bolster episode to discuss the inflection points along a long term startup journey. After leading Return Path for two decades, Matt has a unique perspective on startups and how they develop in the long term. He discusses how the job of a CEO changes as the business scales, the issue of changing product market fit, and the importance of maintaining company values and culture over time. Tune in to this episode to hear what it’s like to be in it for the long haul. 

After sitting on 25 boards and participating in hundreds of board meetings, Jeff Epstein has a deep understanding of how independent directors can contribute. Today on The Daily Bolster, he’s sharing three of the strategies he uses to add value in the board meeting. Jeff Epstein is an Operating Partner at Bessemer Venture Partners and a Lecturer at Stanford University. He’s a former CFO, and currently specializes in B2B Software, Marketplaces and Vertical AI.

Your startup is scaling, but your CEO isn’t. It’s awkward to talk about—but it may be vital for the business. Today on the podcast, we’re joined by Cristina Miller to discuss the warning signs of a CEO who isn’t keeping pace with the growth of the business. She also shares her own experience with leaders who weren’t scaling, advice for solving the problem, and whether you should consider going to the board. Cristina is a seasoned, results-driven C-level executive and board director with a strong track record in digital marketplaces, startups & scale-ups and new business innovation. She’s currently the Chief Operating Officer at Goldbelly.

Which career background provides the best foundation for a future CEO?Today, Dawn Zier—CEO, board chair, and advisor—shares three reasons why an engineering background was vital to her success as a CEO.

Today’s guest is Charlie O'Donnell, founder of Brooklyn Bridge Ventures. He and Matt are diving deep into the journey between entrepreneurship and venture capital. Charlie’s career has given him insight into a myriad of perspectives that influence his work with founders now, from his focus on team dynamics to his direct but empathetic approach to difficult conversations.Later in the episode, Charlie and Matt talk through the current state of the market, the types of deals that are seeing success, and what’s next for Brooklyn Bridge Ventures.

Joining Matt on today’s Ask Bolster episode is Christina Perla, co-founder and CEO of Makelab. Christina’s question: how can founders find the right balance between day-to-day operations and strategic thinking?Matt offers two frameworks to help with delegation and decision-making: the Big Rocks Framework and the Decision-Making Two-by-Two Matrix. Interested in what sustainable and effective time management for leaders looks like? Tune in to the 7 minute episode!

Brad Feld and Matt Blumberg literally wrote the book on Startup Boards. Today, Brad is joining the podcast to share his expertise as the co-founder of Foundry and an experienced early-stage investor and entrepreneur. Tune in to hear Brad and Matt discuss the value of having diverse boards with independent directors who provide different perspectives, experiences, and frames of reference. They share examples, benefits, and potential resources for your board to tap into.

Sarah Personette is a longtime tech executive, independent board member, and—most recently—the Chief Customer Officer at Twitter. Today on The Daily Bolster, she’s sharing her tips for dealing with organizational change in a hyper-growth environment. Tune in to learn why rethinking communication, software, and responsibilities as your company scales is essential to operational excellence. Sarah and Matt also emphasize the importance of building diversity, equity, and inclusion into the fabric of a company’s culture and ensuring all disciplines have an equal voice.

How do you define success? Especially for founders, it’s critical to know which metrics are telling you to stay the course and which ones signal a need for change. In this episode of The Daily Bolster, Andrea Rice—Managing Director of MLT, Bolster board member, and previous founder and CEO of CareerCore—shares three of the most important lessons she’s learned from building and running businesses.