Ep. 022: Starting 8+ Companies and Becoming a Published Author w/ Ben McDougal

Building a Diversified Career Portfolio: Lessons from Serial Entrepreneur Ben McDougal

In the heart of the Midwest, the Des Moines, Iowa business scene is undergoing a radical transformation. Gone are the days when entrepreneurship was a "fringe" activity or a lonely grind in a basement. Today, it is a vibrant, community-driven lifestyle.

In a recent episode of the Rhymes with Odd podcast, host Ryan Snaadt sat down with Ben McDougal—a serial entrepreneur, community builder, and author—to discuss what it takes to manage a diversified career portfolio and how Des Moines has become a focal point for this global movement.

Whether you are a marketing professional at a Des Moines agency or a local founder looking to scale, Ben’s insights on "side-hustle culture" and community-led growth provide a roadmap for the modern professional.

https://www.youtube.com/watch?v=tGdAmeeD0xk

The Art of the Diversified Career Portfolio

One of the biggest hurdles for ambitious professionals in Iowa is the fear of "diluting" their brand. Many worry that if they have too many projects, they will be perceived as mediocre in all of them.

Ben McDougal offers a different perspective. He views his career as a pie chart rather than a single lane. By aligning various projects—from technology in the craft beer space (Flight Bright) to book publishing (Pour Over Publishing)—he creates a "shared energy" that fuels each initiative.

Focusing Your Energy: The 100-Swing Rule

Ben uses a powerful analogy for local business owners: “You might have time to swing 100 times. Do you want to swing that axe at 100 trees, or maybe a couple of selected trees 100 times?”

For Des Moines marketers, this is a lesson in intentionality. Instead of trying to be everything to everyone, identify the 3-4 "slices" of your professional pie that offer the most synergy.

1 Million Cups: The "Front Porch" of Des Moines Entrepreneurship

If you’ve spent any time in the Des Moines business community, you’ve likely heard of 1 Million Cups. Ben McDougal has been a cornerstone of this program for over a decade, helping transition the local chapter from a small coffee shop gathering to a weekly "spectacle" at the Science Center of Iowa.

Connection vs. Transaction

As Ryan Snaadt noted during the episode, many people associate the 1 Million Cups brand directly with Ben. Why? Because of his commitment to long-term connectivity over transactional networking.

For Iowa business owners, the lesson is clear:

• Present, don’t pitch: While Shark Tank is about impressing investors, 1 Million Cups is about sharing ideas and seeking learning.

• Consistency is Key: Ben has had coffee every Wednesday for 10 years. That level of persistence builds a "tribe" that supports you through the highs and lows of business ownership.

Why Des Moines Students Have a "Head Start"

The conversation shifted toward the evolution of entrepreneurship in education. Ryan Snaadt and Ben discussed how "startup" wasn't even a common word in the 90s. Today, students at local institutions like Simpson College are entering the marketplace with a "no permission required" mindset.

Ben’s advice for the next generation of Des Moines talent is to use the "sandbox" of college to build something sustainable. By flexing entrepreneurial muscles early, students are better prepared for the "Future of Work."

The SERV Equation for the Modern Workforce

Ben introduced a framework that every Des Moines HR manager and CEO should pay attention to. He calls it the SERV Equation:

1. Self-awareness/Curiosity

2. Enthusiasm/Initiative

3. Real Skills

4. Vocational Knowledge

In a world where "care is scarce," showing initiative is the fastest way to stand out. Ryan Snaadt recalled a story of a student who was hired on the spot at a pitch competition simply because she was bold enough to ask for a job.

From Side Hustle to Published Author: "You Don't Need This Book"

A major portion of the podcast focused on Ben’s journey to becoming a published author. His book, You Don’t Need This Book, was born out of a desire to synthesize the lessons he learned from thousands of "collisions" within the entrepreneurial community.

Why You Should Consider Writing a Book

For Des Moines marketers and thought leaders, a book is more than just a product; it’s a relic and a marketing piece. Ryan Snaadt and Ben discussed how a book acts as a "business shield" and a platform for future projects.

Ben’s tips for aspiring Iowa authors:

• Start with a Table of Contents: Don't just write A to Z. Bucket your ideas into sections to ensure the book is enjoyable to read.

• Focus on Word Count, Not Page Count: Aim for at least 25,000 words to ensure the project feels like a substantial book rather than a brochure.

• The "Human" Element: Ben intentionally removed the word "I" from his manuscript to ensure the content resonated with any reader, regardless of their industry.

The Launch of Pour Over Publishing

Rather than taking the traditional publishing route or purely self-publishing on Amazon (which can sometimes carry a stigma of lower quality), Ben founded Pour Over Publishing.

This "hybrid" approach allowed him to create a "pro-grade" experience while maintaining 100% creative control and higher royalties. For local entrepreneurs, this serves as a reminder that if the current market options don't fit your vision, you have the power to build the infrastructure yourself.

Final Thoughts: It’s a Dance, Not a Race

Entrepreneurship in Iowa is no longer just about the "grind" in a dungeon. It’s about community, curiosity, and the willingness to "ship your art" even when it isn't perfect.

As Ryan Snaadt highlighted throughout the episode, the key characteristic of successful founders like Ben McDougal isn't just "shiny object syndrome"—it’s the ability to dance with an idea long enough to see it gain traction.

Key Takeaways for Des Moines Business Leaders:

• Show Up and Follow Up: In a world of digital noise, physical presence and consistent follow-up are your greatest competitive advantages.

• Build Your Tribe: Don't build in isolation. Find communities like 1 Million Cups to balance the "loneliness factor" of leadership.

• Leverage Technology: Whether it’s voice-to-text for writing or electronic flight paddles for beer, use technology to add "leveraging efficiency" to your work.

Want to hear the full conversation? Check out the full episode of the Rhymes with Odd podcast with Ryan Snaadt on YouTube or your favorite podcast platform..