1,000 Routes with Nick Bennett

Becoming an entrepreneur takes grit. Deciding to do it solo takes courage. This is 1,000 Routes, the podcast where we explore the stories of solopreneurs who have made the bet on themselves to build a business that serves their life. Every episode you'll hear about the lessons they've learned and the uncommon routes they've taken to stand out in a world that is purposefully trying to commoditize them.

Last refreshed: August 16th, 2025 at 7:45 AM ⓘ

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Episodes

#4 The John Rougeux Route

John Rougeux is a narrative designer and the founder of Flag & Frontier . John shares the route he carved from mechanical engineer, to marketer, to category designer, to solopreneur. (00:00) - Embracing the Entrepreneurial Journey: A Personal Reflection (00:55) - Discovering The Route (01:10) - Networking and Learning in Business (03:00) - The Solopreneur's Mindset (07:48) - Finding Your Motivation and Defining Success (11:48) - The Process of Becoming a Full-Time Consultant (14:04) - The Tu...

Apr 12, 2024•52 min

#3 The Mike O'Neill Route

Mike O'Neill is an elite-level executive coach, leadership trainer, and podcaster. We explore Mike's transition from a corporate HR leader supporting thousands of employees to becoming a solopreneur. He shares the challenges and rewards of Solopreneurship, the lessons learned from mentors, and how building meaningful, long-term relationships has been key to success. (00:00) - Success Through Problem Solving and Trus (01:24) - Reconnecting and Reflecting (04:28) - Uncertainty and Opportunity (09:...

Apr 05, 2024•50 min

#2 The Max Traylor Route [Part 1]

Max Traylor’s journey is a testament to prioritizing what matters most. By turning setbacks into opportunities, he’s found a way to help solopreneurs create businesses that align with the lives they aspire to lead. Drawing from his experience as a consultant and former agency leader, Max explains how he revamped his pricing strategy to create more personal time, the value of nurturing high-level relationships, and the importance of failing on your own terms. He also talks about the ROI of focusi...

Mar 29, 2024•1 hr 14 min

#1 The Andrew Capland Route

Andrew Capland is a coach and mentor of growth leaders, an advisor for product-led SaaS companies, and the host of the Delivering Value podcast. Andrew is on a mission to revolutionize his business and build a media empire. In this episode, Andrew shares his transition from a corporate role at companies like HubSpot, Wistia, and Postscript to becoming a solopreneur driven by passion and purpose. He also touches on the highs and lows of entrepreneurship, dealing with not-so-great clients, and the...

Mar 22, 2024•1 hr 13 min

Welcome to 1,000 Routes

If you call yourself a solopreneur, this is for you. Whether you became one on purpose, or because it seemed easier than getting another job after a layoff, like a lot of people, you're trying to build something meaningful, and you want to do it on your terms. But it’s been harder and it's taking longer than you thought it would to get out of survival mode. And for most people who do make it out and start earning good money, they end up working 60-70-even 80-hour weeks to manage their “success.”...

Feb 19, 2024•2 min

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