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.