1,000 Routes with Nick Bennett

Nick Bennett
  • 5.0 (5)
  • Entrepreneurship
  • Updated Weekly

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.

  1. May 29

    #70 The Josh Lowman Route

    In this episode, Josh Lowman, founder of Gold Front, shares his unconventional path from aspiring filmmaker to building a category design studio working with companies like Uber, Stripe, and Qualtrics. He opens up about early career struggles, getting fired and starting his first agency, and the fear that held him back from launching his second agency for years. He breaks down how he transitioned from a generalist creative studio to a focused category strategy firm, and why productizing his work became the foundation for growth. He also dives into the realities of running an agency—from revenue rollercoasters to redefining success—and how his vision for the business evolved over time. The conversation explores how AI reshaped his thinking, leading him to build a personal brand on LinkedIn and diversify into training products, cohorts, and workshops. Josh shares why personal brand is becoming a defensible moat, how he balances high-ticket client work with scalable education, and why teaching has become a core part of his mission. Throughout the episode, Josh reflects on entrepreneurship, fear, identity, and finding meaning beyond money—offering a raw look at what it actually takes to build, evolve, and sustain a creative business. Timestamps: (00:00) Intro (01:00) From film dreams to first agency (04:00) Getting fired → starting a business (07:00) Fear of failure delaying Gold Front (10:00) Landing early clients like Stripe & Uber (14:00) From creative studio → category strategy (20:00) The agency rollercoaster (wins vs dry spells) (24:00) Why business goals constantly evolve (28:00) AI, personal brand, and LinkedIn growth (32:00) Diversifying revenue beyond services (36:00) Balancing high-ticket work with education (39:00) Teaching, purpose, and what’s next Follow Josh on LinkedIn: https://www.linkedin.com/in/joshlowman/ Check out Gold Front: https://www.linkedin.com/company/gold-front/   – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    44 min
  2. #69 The Morgan Ingram Route

    May 22

    #69 The Morgan Ingram Route

    In this episode, Morgan Ingram, Founder & CEO of AMP Social shares his journey from being the worst-performing SDR on his team to becoming one of the most recognized voices in modern B2B sales. He opens up about the mindset shift that changed everything early in his career, the lessons he learned working with John Barrows, and why going all in on self-development became the foundation of his success. The conversation dives deep into personal branding, content strategy, and the future of sales in the AI era. Morgan explains why he believes the market has over-indexed on AI, why human development matters more than ever, and how he’s building a new framework centered around three pillars: human growth, sales skills, and AI proficiency. He also reflects on entrepreneurship, fulfillment, consistency, and redefining success beyond revenue and vanity metrics. Throughout the episode, Morgan shares an honest look at ambition, identity, burnout, and growth. If you are trying to build something meaningful in a rapidly changing world, this is for you. Timestamps: (00:00) Intro (00:47) From worst SDR to sales leader (04:30) The emotional rollercoaster of entrepreneurship (06:00) Losing $450K in pipeline overnight (15:00) Why the production model failed (21:00) Narrative-led growth & content strategy (25:00) Scaling too fast and chasing the wrong vision (32:00) Rediscovering coaching & rebuilding the business (34:00) Redefining success beyond money (41:00) The 3 layers of future sales leaders Follow Morgan on LinkedIn: https://www.linkedin.com/in/morganjingramamp/ Check out AMP Social: https://www.linkedin.com/company/theampsocial/   – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    48 min

  3. May 15

    #68 The Katelyn Bourgoin Route

    In this episode, Katelyn Bourgoin, founder of UNIGNORABLE, discusses her journey from the restaurant industry to entrepreneurship, focusing on customer research, brand consulting, and building a personal brand. She shares her experience with a failed tech startup and a short-lived barbecue business before transitioning to a content-driven model through her newsletter, Why We Buy. Katelyn explains how the newsletter gained sponsorships and became profitable during a challenging time in her life, including her husband’s injury. She talks about shifting from consultancy to productized services, using AI to create valuable content, and evolving her business model to help entrepreneurs find their unique brand message. Katelyn also reflects on UNIGNORABLE’s growth, a program designed to help entrepreneurs define their “ownable idea,” and how it evolved after several iterations. Katelyn reveals the challenges of balancing multiple ventures and raising a family, including burnout, and her goal of creating a scalable, high-impact service business with a partner. She is now focused on building a sustainable business that operates independently of her. (00:00) Intro (00:50) Agency roots and scaling frustration (01:43) VC startup lessons and failures (02:39) The importance of customer research (04:16) Why We Buy's rapid growth (06:21) Family challenges while going all in (10:46) Transition from sponsors to products (14:40) Contemplating a business pivot (16:58) Selling Why We Buy business model (20:18) UNIGNORABLE's origins with Demand Curve (22:53) Cancer scare and finding a partner (25:43) AI commoditizes expertise for entrepreneurs (30:23) The importance of making it their idea (37:56) Productizing ownable ideas for entrepreneurs Follow Katelyn on LinkedIn: https://www.linkedin.com/in/katebour/Check out UNIGNORABLE: https://www.beunignorable.com/ – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    48 min

  4. May 8

    #67 The Vince Pierri Route

    In this episode, Vince Pierri of VAP Coaching shares his journey from being a full-time pastor to becoming a public speaking coach, and how a shift into creating high-traction infographics skyrocketed his business. He talks about the challenges and lessons learned from transitioning to LinkedIn content creation, including why certain formats like infographics have worked so well for him, and how they solve a major gap in the public speaking industry. Vince dives into the process behind his infographics, how they became a selling point, and how his unique approach of education-first content stands out in a crowded LinkedIn space. He reflects on the ups and downs of cohort-based offers, working with other creators, and balancing high-impact work with the demands of entrepreneurship. As Vince continues to refine his offers, he also opens up about his partnership with Heike and how they are scaling a new enterprise-focused offer that combines his infographic expertise with her viral video knowledge. He shares insights into how they are both optimizing for less time and higher impact in their new venture. (00:00) Intro (01:00) Vince’s transition from pastor to public speaking coach (03:00) The financial motivation behind leaving ministry (06:00) Building an audience on LinkedIn (09:00) The shift to creating infographics (11:00) The gap in public speaking content and how infographics filled it (15:00) The challenge of scaling content creation (18:00) Starting the infographic cohort and pricing strategies (22:00) Balancing low-ticket and high-ticket offers (25:00) The evolution of Vince’s enterprise offer with Heike (30:00) Partnering for a more sustainable business model (34:00) Key learnings from running a cohort-based business (39:00) Vince’s plans to scale and return to pastoring Follow Vince on LinkedIn: https://www.linkedin.com/in/vincent-angelo-coach/ Check out VAP Coaching: https://www.linkedin.com/company/vap-coaching/  – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    47 min

  5. May 1

    #66 The Logan Lyles Route

    In this episode, Logan Lyles, founder of DemandShift Summit, shares how he transitioned into entrepreneurship after being unexpectedly laid off and why that moment became the catalyst for building a differentiated B2B marketing business. Logan walks through his early days of landing clients, leveraging his network, and thinking strategically about his offer before going to market. He breaks down how relationship-driven outreach, a simple LinkedIn launch post, and a creative research report helped him secure his first clients quickly and validate his business model. Logan dives deep into his unique approach to webinar-led growth, explaining how he turned webinars into both a lead generation engine and a scalable media asset. He shares how he built a flywheel by combining content, audience building, and client delivery into one system allowing him to generate results for clients while simultaneously growing his own audience and pipeline. Throughout the conversation, Logan unpacks lessons on positioning, leveraging existing skills, building in public, and creating a service that doubles as a “permissionless demo” of your expertise. (00:00) Intro (01:00) Getting laid off → becoming an entrepreneur (03:00) Landing first clients through network (06:00) Using survey to to generate content and pipeline (10:00) Why his outbound didn’t feel like outbound (14:00) Content as a networking tool (events & outreach (20:00) Choosing webinars as his core offer (23:00) The 2-step signup that 5x’d conversions (30:00) Building a media + service flywheel (36:00) Differentiation through audience ownership (40:00) What he’d do differently + scaling challenges Follow Logan on LinkedIn: https://www.linkedin.com/in/loganlyles/ Check out DemandShift Summit: https://www.linkedin.com/company/demandshift-summit/  – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    45 min

  6. Apr 24

    #65 The “IRON” Mike Steadman Route

    In this episode, Mike Steadman, also known as “Iron Mike”, is a Marine Corps veteran and founder, and he shares his journey from leading troops in Afghanistan to building a business rooted in category design and go-to-market strategy. He reflects on leaving the military, launching a nonprofit boxing gym, and eventually pivoting into higher-leverage work after realizing the importance of market demand. Mike breaks down his core philosophy that category comes first, explaining why most founders struggle with positioning, how labels like “fractional” commoditize your value, and why defining your own category is key to standing out. He also shares how he bootstrapped a podcasting business during COVID and used it to build relationships before transitioning into strategy. The conversation dives into his “movement to contact” approach to sales, focused on volume, consistency, and reps, and why learning sales early is critical. Mike emphasizes the importance of strong point of view, clear language, and consistent content, and shares his vision for adversarial go-to-market, built on one truth: the market owes you nothing and you have to earn every customer. (00:00) Intro (02:00) Starting a nonprofit boxing gym (05:42) Why businesses fail (07:04) Discovering category design (10:15) Why “fractional” is a trap (11:41) Spotting emerging markets (16:34) Getting first clients (20:04) Bootstrapping a business (24:07) Red team and positioning process (30:51) Lead generation and sales system (38:18) Developing a strong point of view (46:38) What’s next: adversarial go-to-market Follow Mike on LinkedIn: https://www.linkedin.com/in/iron-mike-steadman/Check out OP4: https://op4.co — Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    49 min

  7. Apr 17

    #64 The Louis Grenier Route

    In this episode, Louis Grenier, positioning + GTM consultant for B2B at Stand The F*ck Out and founder of Everyone Hates Marketers, shares his unconventional journey from a mechanical engineering background to building a successful marketing consultancy. Louis reflects on his early days in Dublin, how serendipity led him to stay, and his shift from agency work to becoming a marketing professional. He also talks about the lessons learned from burning out in his first agency and how he found his true passion in marketing, which ultimately shaped his business philosophy. Louis explores his Everyone Hates Marketers podcast experience, where he emphasizes the importance of standing out in a crowded market by being unapologetically authentic. He shares his unique approach to positioning, go-to-market strategies, and creative differentiation in a noisy world. Throughout the conversation, Louis opens up about his entrepreneurial highs and lows, his time at Hotjar, and how his personal health challenges influenced his career, providing invaluable insights on growing a business based on values and the power of embracing failure. (00:00) Intro (01:49) Tech boom and serendipity shaped career (04:10) Why he chose to stay in Dublin (05:24) First real marketing role and lessons learned (06:30) Launching agency and early mistakes made (08:02) Cancun burnout after failed client experiment (10:06) Hotjar role and podcast beginnings (16:34) First sales and early business anxiety (20:46) Current revenue streams and business model (22:06) Cutting business branches to refocus growth (25:07) Doubling down on B2B GTM consulting (28:35) Generosity over metrics drives real growth (30:46) Beta readers improved book quality massively (31:54) Book became powerful sales engine (36:19) Cancer diagnosis brought clarity, not change (40:38) Regrets about past relationships and growth (41:25) Pruning business to focus on one thing Follow Louis on LinkedIn: https://www.linkedin.com/in/louisgrenierCheck out Everyone Hates Marketers: https://www.everyonehatesmarketers.comCheck out Stand The F*ck Out: https://www.stfo.io — Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    46 min

  8. Apr 10

    #63 The Michelle Warner Route

    In this episode, Michelle Warner, a business strategist and designer, shares her transition from building venture-backed startups to creating a smaller, more sustainable business. After ıexperiencing intense burnout, she stepped away from the traditional growth-at-all-costs model and began designing a business that aligned with her life. She reflects on how working with single mothers in a social impact startup revealed a growing wave of online entrepreneurship and inspired her consulting work. Michelle also breaks down her core philosophy of relationship marketing vs traffic marketing, explaining why most service-based businesses struggle when they rely on audience growth alone. She shares how building intentional relationships, instead of chasing scale, leads to better clients, more aligned growth, and a more sustainable business model. (00:00) Intro (00:39) Leaving startups after burnout (02:46) Shift to a smaller business (02:56) Discovering online entrepreneurs (06:59) Offers evolve over time (12:32) Relationship vs traffic marketing (28:00) Real vs transactional networking (29:37) Connection avatars strategy (32:59) Using a podcast to network (35:23) Small, specific asks (46:12) Defining what’s enough Follow Michelle on LinkedIn: https://www.linkedin.com/in/warnermichelle/ Check out Networking that Pays: https://www.themichellewarner.com/  – Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠ Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

    50 min
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5
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About

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.

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