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The Daily Bolster: On Being an Entrepreneur

June 22, 2023

As we close the door on Season 1 of The Daily Bolster, we’re reflecting on some of our favorite episodes—and there are a lot of them.

Every single guest brought an insightful perspective on entrepreneurship, leadership, or the startup ecosystem. Our hope is that The Daily Bolster provides you with actionable tips and practical encouragement for your own growth.

In case you missed them, we’re sharing a selection of episodes specifically curated to help you succeed as an entrepreneur.

Is entrepreneurship right for you?

Quick Tip: 🧐 Consider whether you would care about what you're doing even if you weren't the CEO.

Some people aren’t founders, but they should be—and some people are founders, but shouldn’t be. Allie Egan shared three questions you can ask yourself to determine whether entrepreneurship is the right path for you.

Why—and how—do you want to scale your business?

Quick Tip: 💭 Think critically about what scale means to you

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. Tune in to hear about Rand’s unique funding and scaling philosophies and how he hopes to blaze an alternate trail for small and medium sized businesses.

What do you do when you feel overwhelmed?

Quick Tip: ❌ Have a "to don't" list

Bestselling author, keynote speaker, startup investor, and former c-suite executive Fran Hauser shares her tips on staying aligned with your priorities, using boundaries to create space in your day, and our new favorite tool: the to-don’t list.

What do you learn about yourself as an entrepreneur?

Quick Tip: 💥 Remember, conflict isn't dysfunction, it's information

Former Lessonly CEO Max Yoder shares what he learned about himself through the scaling process.

Do you have the bug to start something new?

Quick Tip: ⚖️ Know what needs to be true for you to take a risk

An engineer and technologist by degree, Sherisse Hawkins got her start as a Disney Imagineer, designing theme parks around the world. Now, though, she considers herself a “corporate escapee,” driven by a love of starting new things and solving new problems.

Want to keep listening? These episodes are a great place to start:

We'll be back with Season 2 after Labor Day! Don't want to miss an episode? Subscribe to get notified when we return.