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The Daily Bolster: Week One Recap

April 3, 2023

We’re still buzzing from the release of The Daily Bolster podcast last week!

Week One was packed with some exceptional guests and even more exceptional advice. In case you’ve not subscribed yet or still have episodes sitting in your queue, we’re recapping the highlights from this week, plus giving a little sneak peek into what we have in store for next week.

Episode 1: 3 Tips to Scale Your Culture with Nick Mehta

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 Matt discussed what happens to company culture when you achieve your scaling and growth goals.

Episode 2: Managing Up with Cristina Miller

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 director with a strong track record—shared what it looks like to set expectations and build a strong relationship with your CEO.

Episode 3: Common Mistakes Founders Make with Fred Wilson

Fred Wilson has been a venture capitalist since 1987—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.

Episode 4: Cultivating Talent to Promote Internally with Nick Francis

In this episode, Nick Francis—co-founder and CEO of Help Scout—joins Matt to discuss what it takes to cultivate in-house talent and embody organizational values. Matt also shared his playbook for building effective teams and developing leaders with a growth mentality.

Episode 5: Deep Dive with Jeff Epstein

Career shifts are more common now than ever, even for senior executives. Experienced CFO and operator Jeff Epstein joined Matt 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.”

Here’s a sneak peak of the conversation:

 💵 Making the move to CFO

 🔀 Transitioning between industries and sizes of business

 🪑 Why you should take an outside board seat

 🪫 Serving on the board of a company that failed

Curious about what’s coming in Week Two?

Today, David Cohen, Founder and Chairman at Techstars, is 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.

A few highlights:

 𐄷 The difference between obsession and passion

 🌐 What it looks like to be people focused

 🔑 The importance of values and dedication

Stay tuned for the rest of this week’s episodes:

  • Success as a Fractional Exec with Courtney Graeber
  • 3 Ways VCs Say "No" Without Saying "No" with Jenny Fielding
  • Building a Strong Culture with Jailany Thiaw
  • Deep Dive with Brad Feld

The Daily Bolster for folks in the startup world who—like us—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.

Listen to all episodes here (or on your favorite podcast platform), and never miss an episode when you sign up for daily email notifications.

Have a question for Matt or one of our guests? Email us at