Sometimes orthodoxy needs to be challenged, and Rand Fishkin, co-founder and CEO of SparkToro, believes that by doing so, we can build something better than what came before. Today, he and Matt are diving deep. Tune in to hear about the unique funding and scaling philosophies behind SparkToro, and how Rand hopes to blaze an alternate trail for small and medium sized businesses. They also discuss the lessons Rand learned as founder and CEO of Moz—where, incidentally, Matt was on the board—including what it was like to go into business with his mother, getting into SEO when the industry still had major doubts, and the importance of understanding yourself, especially as a founder. Trust us, you don’t want to miss this episode!

Joining Matt on today’s Ask Bolster episode is Ning Zhang, CEO of Flatfee, a managed marketplace to connect global entrepreneurs with professional freelancers. Her question: how can a CEO know if they’re being realistic, or overly optimistic? She and Matt discuss finding the balance between listening to customers and leading them to their solution, along with a few other key indicators of a successful idea.

What would you want to change when you look back on your career? Scott Dorsey is a CEO turned investor and board member, and now that he’s on the other side, he’s sharing three things he wishes he had done differently as a CEO. Tune in to learn from his experience and hear what he loves about being on the other side of the table.

What does it mean to interview for culture fit? How should CEOs and leaders go about doing it—and is there a better way?Rory Verrett is the founder and managing partner of Protégé Search, the leading retained search and leadership advisory firm focused on diverse talent. In today’s episode, he and Matt discuss why CEOs are not always the best arbiters of company culture, then dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.

Today’s podcast is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers. Today, she and Matt dive into the reasons why podcasts are such a great way to get your voice—literally—out into the world. Tune in to hear Lindsay’s tips for starting a podcast as a CEO, setting expectations, asking meaningful questions, and creating human connection.

Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur. In this episode, he and Matt take a deep dive into how startups and venture capital have changed over the past 25 years—and what has stayed the same. They also discuss the dynamics of startup boards, along with common characteristics that make founders or companies successful at scale.

Joining Matt on today’s Ask Bolster episode is Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines. Jailany and Matt discuss the best ways to get company buy-in as you build and maintain a strong and welcoming culture—especially in an early stage or remote environment.

It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says pre-seed investor Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either. On today’s episode, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.

If you know anything about Bolster, you know we’re a champion for fractional executives. As an Interim Chief People Officer, HR Executive Consultant, and trusted mentor to executive teams, Courtney Graeber provides feedback and recommendations that enhance organizational culture and attract, develop, and retain top talent. Many of her clients are navigating transitional periods—and that’s where Courtney’s expertise comes in. Listen in to learn what it’s like to be (or work with) a fractional head of people.

As the Founder and Chairman at Techstars, David Cohen has watched over 10,000 founders pass through their startup programs. He’s developed an eye for those who will achieve success. Today, he’s sharing the top three signs he looks for that differentiate successful founders—things that are nearly impossible to fake. Either you have them, or you don’t.