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PODCAST

The Daily Bolster

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

business entrepreneurship

All Episodes

5:54

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

The Daily Bolster ·

2023/06/12

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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31:06

Deep Dive with Max Yoder

The Daily Bolster ·

2023/06/09

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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8:11

Lessons Learned from Selling a Business with Mindy Lauck

The Daily Bolster ·

2023/06/08

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

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5:26

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

The Daily Bolster ·

2023/06/07

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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3:48

Deciding if Entrepreneurship is Right for You with...

The Daily Bolster ·

2023/06/06

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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6:15

Strategies for Nurturing Alignment with Clare Hart

The Daily Bolster ·

2023/06/05

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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35:13

Deep Dive with Greg Sands

The Daily Bolster ·

2023/06/02

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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5:20

Learning About Yourself While Growing a Business with...

The Daily Bolster ·

2023/06/01

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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5:23

How to Improve Your Board Meetings with Robert Wolfe

The Daily Bolster ·

2023/05/31

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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7:01

Interacting with the Board as a CXO with Cristina Miller

The Daily Bolster ·

2023/05/30

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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36:22

Deep Dive with Sarah E. Brown

The Daily Bolster ·

2023/05/26

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

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5:39

Transparency in Action with George Bilbrey

The Daily Bolster ·

2023/05/25

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.

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6:28

Early vs. Late Stage Boards with Joe Hurd

The Daily Bolster ·

2023/05/24

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.

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5:21

What Makes a Great Fractional Product Leader with...

The Daily Bolster ·

2023/05/23

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.

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7:33

Staying Scrappy as You Scale with Rand Fishkin

The Daily Bolster ·

2023/05/22

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.

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29:04

Deep Dive with Dawn Zier

The Daily Bolster ·

2023/05/19

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.

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5:28

What to Expect After Fundraising with Yami Payano

The Daily Bolster ·

2023/05/18

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.

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6:48

How to Effectively Onboard New Board Members with...

The Daily Bolster ·

2023/05/17

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.

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5:40

Navigating an Economic Downturn with Tim Porthouse

The Daily Bolster ·

2023/05/16

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.

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5:38

Maintaining Culture Through Hyper Growth with Chad...

The Daily Bolster ·

2023/05/15

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.

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216 results

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