Last week, we reached a massive milestone—100 episodes of The Daily Bolster!
To celebrate, we’re looking back on some of our listeners’ favorite moments. These clips cover so much of what The Daily Bolster is all about: sharing insights, motivation, and great advice in short, easy-to-listen segments.
Don’t see your favorite clip? Let us know which episode impacted you the most by tagging us on LinkedIn, X, or Threads!
Mistakes and the founder growth journey
No founder should feel bad about making mistakes. If you aren’t making mistakes, you probably aren’t taking enough risks. Maëlle Gavet, CEO of Techstars, shared about the biggest mistakes founders make on their growth journey—how to avoid them when possible, how to navigate them, and how to learn from them.
What makes a founder pitch great
As a Partner at The Venture Collective, Cat Middleton sees hundreds of pitches a year. In this episode, she shared three things founders can do to stand out and earn an investment. One standout piece of advice? Be sure to have a clear vision of the future you're building.
Making and delegating decisions
Our first guest of Season Two was none other than Bob Blumberg, who—in addition to being Matt’s dad—is a retired tech founder and seasoned CEO. In this episode, Bob shared management wisdom in the form of his matrix for decision-making and delegation. This unique approach nurtures growth and empowers managers to make the right calls (and to know when collaboration is key).
Find talent that's ready to step up
In this Ask Bolster episode, Matt and Nick Francis, the co-founder and CEO of Help Scout, talked about building effective teams. Matt shared his playbook for developing leaders with a growth mentality.
The best boards are the ones where the CEO views it as a team
Brad Feld is partner and co-founder of Foundry, and a long-time early-stage investor and entrepreneur. In this episode, he and Matt dove into the dynamics of successful startup boards. They also discussed how startups and venture capital have changed over the past 25 years—and what has stayed the same.
How VCs say "no" without saying "no"
Founders need to be able to hear what’s left unsaid in conversations with investors. Sometimes, according to pre-seed investor Jenny Fielding, VCs aren’t ready to invest in a startup, but they’re not ready to say no, either. In this episode, she shared three signs a VC may be saying “no” without saying the words—and what founders should do next.
Non-linear career paths
Sarah E. Brown is a tech marketing expert, startup mentor, ecosystem builder, and the author of Lead Upwards. She and Matt discussed creative career paths—Sarah considered “The Non-Linear Path” as an alternate title for her book—and the unique opportunities startups present.
Common mistakes founders make
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, like having too many co-founders. In this episode, he talked about the challenges facing founder teams, avoiding valuation misalignment, and finding the right deal.
Hiring a team that's ready to prove themselves
Curious about the stages of building a leadership team? Check out this episode, where Nick Mehta, CEO of Gainsight, shared about his journey of launching and scaling Gainsight to 1200 employees over 10 years.
Advice for founders and CEOs
Matt and Adam Slutsky, Managing Partner at Gather Ventures, discussed the arc of Adam’s career and what he’s learned along the way. Adam also shared about his time at Tough Mudder, the power of community, and the story behind Gather Ventures.
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