The Daily Bolster
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The Daily Bolster is a quick-hitting podcast for startup leaders scaling their businesses.
Every day, Matt Blumberg, Co-founder and CEO of Bolster, is joined by experienced operators and industry experts who share their real-world experiences and practical advice. Together, we discuss professional development, venture capital, startup strategy, and tips and tricks for executive growth. It’s the actionable insight you need to scale—in under 10 minutes.
The Daily Bolster is produced by Bolster, the new way to find the right executives. We supercharge startup growth by matching CEOs with transformational executives, mentors, and board members—without the hassle of traditional talent sourcing. Built by entrepreneurs for entrepreneurs, Bolster’s on-demand marketplace is packed with diverse, highly qualified leaders ready for full-time, interim, fractional, project-based, advisory, or board roles.
Have a question for Matt or one of our guests? Email us at thedailybolster@bolster.com. Interested in learning more about Bolster? Sign up or start searching for free at bolster.com.
46 Episodes
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Today’s episode is a deep dive with tech marketing expert Sarah Brown. Sarah is a startup mentor, ecosystem builder, and the author of Lead Upwards.She and Matt discuss creative career paths—Sarah considered “The Non-Linear Path” as an alternate title for her book—and the unique opportunities startups present. They also share their thoughts on the contrast between startups and large companies, from office politics to overall function. Tune in to hear about mentorship, team hierarchy, and Sarah’s take on quitting as an executive.
How transparent is too transparent? On today’s Ask Bolster episode, Signpost CEO George Bilberry joins Matt to discuss how open CEOs should be with their teams, especially in an uncertain environment. While there’s not a one-size-fits-all answer, Matt advises founders to err on the side of transparency. Tune in to hear his full answer, the reasoning behind it, and the exceptions.
Our guest today was one of Bolster’s first 100 members! Joe Hurd is an operating partner at SOSV—an early-stage venture fund—and an experienced board member. He joins Matt to unpack the differences between early and late-stage boards. They also talk about the distinction between a player and a coach (and what that means as a board member), and how to avoid groupthink.
Drew Dillon—Principal at ProductBridge, Bolster Member, product and technology expert—joins the podcast today to discuss what makes a great fractional product leader. Having alternated between full-time and fractional work himself, he brings a unique perspective to the conversation. Listen to the episode to hear Drew and Matt discuss what a fractional head of product can get done—and what they can’t.
Rand Fishkin—co-founder and CEO of Sparktoro—joins the podcast again! This time, he’s sharing tips for staying scrappy as you scale your business. Tune in to hear Rand and Matt discuss the impact of small market segments, the importance of ruthlessly interrogating your goals, and more.
We’re diving deep with CEO, board chair, and advisor Dawn Zier. On today’s episode, she talks about how learning to step out of her comfort zone was a pivotal moment in her career, and how one of the best things that ever happened to her came from a moment of extreme disappointment. Tune in to listen to Dawn and Matt discuss the hardest part about being a board member, the variety of CEOs’ career arcs, and more.
It’s another Ask Bolster episode! Today, we’re joined by Yami Payano, CEO of Sign-Speak. She and Matt discuss what founders can expect after their first round of financing, what challenges to look out for, how to forecast, and more. There are great tips for everyone here, but new founders especially won’t want to miss this episode.
So much effort goes into selecting new board directors. Once the new director is picked, the vast majority of CEOs think the job is over. That’s not the case. Today, we’re welcoming Heidi Roizen, Partner at Threshold Ventures and recovering entrepreneur. She and Matt discuss how to successfully onboard new board members in order to maximize their contribution to your team.
Today’s guest is CEO coach and former startup CEO Tim Porthouse. Having been through three challenging downturns himself, he’s eager to share his knowledge and experience with others. Tune in to listen in as Tim and Matt discuss how CEOs can find balance and navigate an economic downturn.
Chad Dickerson was at Etsy as it scaled from 40 employees to 1000. Today, he’s sharing three strategies CEOs can use to stay connected to employees, especially through substantial growth.
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.
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