Espresso to Success: Jarie Bolander’s Story-Driven Journey

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Welcome back to another issue of BizStack’s Entrepreneur Spotlight. Today, we are thrilled to have Jarie Bolander, a maestro of storytelling and the brain behind Story-Driven, share his journey with us.

Meet Jarie Bolander

Jarie is not your typical entrepreneur. Driven by a firm belief in making complex things understandable, he has dedicated his career to helping businesses tell their stories. Jarie believes in crafting a more ethical, inclusive, and resilient world by educating and inspiring entrepreneurs across the age spectrum, from 18 to 80. He does this powered by his love for locally crafted espresso, which keeps him energetic and ready to tackle the B2B Sales & Marketing Strategy world.

What is Get Story-Driven?

The concept behind Story-Driven is simple yet profoundly impactful. Jarie and his team focus on “systemizing storytelling” to accelerate brand awareness, generate quality leads, and grow revenue. They apply proven storytelling techniques to help businesses articulate unique and compelling narratives. Their primary industry is B2B Sales and Marketing Strategy, though the power of storytelling transcends various fields.

A Day in the Life of Jarie

Jarie says there’s no “typical” week in his entrepreneurial life. However, he sheds light on the recurring themes that dictate his weekly schedule:

  • Talking to Prospects: Understanding the unique needs and challenges of potential clients.
  • Getting Work Done: Implementing strategies and creating content that narrates compelling stories for clients.
  • Building Thought Leadership: Engaging in activities that position himself and Story-Driven as authorities in storytelling and marketing.

What keeps this intricate machinery running smoothly? A blend of essential tools and technologies, such as Email, conference calling software, and Google Suite Apps, which streamline day-to-day operations.

Growth Strategies and Productivity Tips

Jarie credits much of his business growth to two core strategies:

  • Personal Brand Building: Developing a personal brand that resonates with trust, reliability, and expertise.
  • Thought Leadership: Sharing knowledge and insights that reinforce his authority in storytelling and marketing.

On the productivity front, Jarie offers two invaluable tips:

  • Waking up early to work out and plan the day.
  • Quitting early to reflect and strategize.

Overcoming Challenges and Celebrating Achievements

Every entrepreneur faces their share of hurdles, and Jarie is no exception. He isolates finding a desirable product or service as his greatest obstacle — a challenge he approaches by creating offerings that compellingly address real-world needs.

A man with a beard and short hair, resembling Jarie Bolander, is wearing a blue blazer and checkered shirt while sitting in an outdoor urban area with plants and buildings in the background.

Jarie Bolander: Entrepreneur, Author, Podcaster

Among Jarie’s notable achievements is his company’s acceptance into renowned accelerators such as 500 Startups and Launch Pad Digital Health. These milestones validated his business model and expanded his network extensively.

Advice for Aspiring Entrepreneurs

For those contemplating the entrepreneurial path, Jarie has some sage advice:

“Be prepared to be comfortable being uncomfortable.”

Jarie Bolander

This mantra encapsulates the essence of entrepreneurship: navigating the unknown with courage, intuition, and adaptability.

Jarie Bolander’s Lightning Round

In this lightning round, I asked Jarie Bolander to answer 13 rapid-fire questions:

What’s something that’s in your pocket right now, besides your phone?


Artificial intelligence: hope or dread?


Your favorite place to think big?

Walking through Golden Gate Park

If you were out of business tomorrow, what job would you pursue?

Probably something in the trades.

One object from your childhood you could never throw away?

My Commodore 64 computer

One feature you wish your phone had?

Selective mute for different times of the day.

Your favorite mobile app?


The book that most influenced you?

The War of Art

Messy desk or clean desk?


One thing you always have in your fridge?


The most creative measure of success you’ve set for a team?

How many experiments did we run this week?

Your favorite time-saving hack?

Do less

Best movie ever?

Die Hard

Discover More

Intrigued by Jarie’s story and want to delve deeper into the art of storytelling? He invites you to explore his Story-Driven books, which are essential reading for anyone looking to enhance their narrative skills.

Three book covers by Jarie Bolander, titled "Story-Driven Outreach," "Story-Driven Decks," and "Story-Driven Marketing," each featuring thematic illustrations.

Story-Driven Foundation (3 book series)

Furthermore, for those eager to learn more about Jarie and Get Story-Driven:

Stories like Jarie’s inspire us at BizStack and remind us of the power of innovation, resilience, and human connection. We thank Jarie for sharing his journey and insights with our community.

Stay tuned for more Entrepreneur Spotlight stories, where we uncover the stories behind the individuals reshaping our world, one idea at a time.

A special thanks to Shaun Gold for introducing us to Jarie Bolander.

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