We have a little more than two weeks of The Daily Bolster podcast under our belts now, and we’re off to a great start! I announced it here, and I thought I’d post links to the first bunch of episodes…I don’t think I’ll do this regularly, though. You can listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.
Our very first guest on The Daily Bolster was Nick Mehta, CEO of Gainsight. As an early-stage startup or a small business, you have significant influence over the culture—but what happens when you’re one of many? Nick and I discussed what happens to company culture when you achieve your scaling and growth goals.
Executives are often caught in the middle of the leadership dynamic, managing both up and down the organization. Cristina Miller—a seasoned, results-driven executive and board member (including on Bolster’s board!) with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.
Fred Wilson has been a venture capitalist since 1987 and has worked with me for over 20 years now—so it’s fair to say he’s witnessed a few founders and become familiar with their most common mistakes. Listen to this episode to learn how to recognize and avoid those mistakes for yourself.
In this episode, Nick Francis—co-founder and CEO of Help Scout—joins me to discuss what it takes to cultivate in-house talent and embody organizational values. I talk about my playbook for building effective teams and developing leaders with a growth mentality as part of this.
Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator (and one of my former board members) Jeff Epstein joined me for an extended episode about the ins and outs of career transitions and the surprises that come with them, from role changes to new industries to vastly different organizational structures. Tune in to follow the shifts in Jeff’s career journey, hear about the lessons he learned firsthand, and get his advice for founders looking to scale. “I always wanted to develop a circle of competence and then over time expand the circle,” Jeff says. “You just learn more.”
David Cohen, Founder and Chairman at Techstars, shares 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. This one is awesome.
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.
It’s important for founders to be able to hear what’s left unsaid in conversations with VCs. Sometimes, says one of NYC’s top pre-seed investors Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either. Here, Jenny shares three signs a VC may be saying “no” without saying the words—and what founders should do next.
Jailany Thiaw, founder and CEO of UPskill, a future-of-work startup automating feedback in entry-level hiring pipelines, joins me to 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.
Brad Feld is partner and co-founder of Foundry, and a long time early stage investor and entrepreneur who I’ve also worked with for more than two decades. In this episode, he and I 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.
This episode is all about podcasting. Meta, right? Lindsay Tjepkema is the CEO and co-founder of Casted, the podcasting solution for B2B marketers. She and I 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. We’ve loved partnering with Lindsay and her team so far on The Daily Bolster!
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, and is also on Bolster’s Board of Directors. He and I discuss why CEOs are not always the best arbiters of company culture, then we dive into what it means to look for specific values throughout the interview process, rather than the vague concept of a culture fit.
The Daily Bolster is for people in the startup world want to hear from industry experts of all backgrounds, but don’t always have the time to listen to full length interviews, even at 2x speed. Instead, we’re getting straight to the point with mostly 5-minute episodes. Any and all feedback welcome!