1,000 Routes with Nick Bennett

Nick Bennett
  • 5.0 (4)
  • 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. OCT 3

    #58 The Marc Thomas Route

    In this episode, Marc Thomas, founder of Positive Human, mentor at TinySeed, and former Sr. Growth Marketer at Podia, traces an unlikely path from freelance journalism to co-founding doopoll, surviving a COVID-era near-meltdown, and ultimately reinventing himself as a lifecycle/email operator for SaaS. Marc shares the chaotic “we priced it in the hallway” moment, the lesson of raising money before true validation, and the four-day surge that took doopoll from 1.6M to 16M votes—and nearly torched the company with usage-based bills. He and Nick dig into the solopreneur head-game: optionality vs. salary, why Marc would take less money for more freedom, and how “punk” DIY energy: charisma, coaching, and seeing work through end-to-end wins in growth. Marc shares candid reflections on confidence dips, building pipeline without becoming your own worst client, and a pragmatic cash-flow system that lets him sleep at night while he eyes a return to software on his own terms. (00:00) Intro (00:29) Starting as a freelance journalist (01:58) Creative gigs lead to a voting tool idea (03:48) Building doopoll in four days (04:19) Landing a 25k deal on the spot (07:01) Fundraising before validation (08:51) From 1.6M to 16M votes and server crashes (10:32) Choosing stability and leaving doopoll (17:22) The banker vs. taxi driver analogy (20:52) Taking less money for more freedom (26:18) Emotional whiplash of solopreneurship (27:00) Lifecycle email and intersecting skills (30:26) Punk marketing and DIY growth (33:29) Learning charisma and coaching clients (43:24) Cash-flow forecasting and personal runway (45:39) Pipeline focus and new software projects Follow Marc on LinkedIn: https://www.linkedin.com/in/iammarcthomas  Check out Positive Human: https://www.positivehuman.co/  Check out Tinyseed: https://tinyseed.com/  — Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    51 min

  2. AUG 8

    #57 The Asia Orangio Route

    In this episode, DemandMaven founder and growth strategist Asia Orangios shares her path from laid-off marketing lead to trusted advisor for PLG SaaS companies. What started as a solo consulting gig in 2018 evolved into a boutique growth consultancy—and along the way, Asia discovered that the real problem isn’t always marketing. It’s everything that comes after: product experience, activation, pricing, and turning demand into actual revenue. Asia reflects on the emotional rollercoaster of early entrepreneurship, the burnout cycles that pushed her to build a team, and the surprising role public speaking played in her pipeline. She opens up about managing ADHD as a founder, learning to delegate the work she once thought only she could do, and why her next act might just be as CEO of a SaaS company—not just a consultant to them. (00:00) Intro (00:47) How Asia became a solopreneur (03:19) Shifting to strategic growth consulting (06:27) Team building with ADHD in mind (11:02) Growth through delegation and feedback (25:53) Managing work and life demands (28:30) Using AI to grow smarter (29:22) Why speaking matters in business (29:48) Business impact of public speaking (36:34) Marketing opportunities beyond the usual (41:42) Overcoming doubts and embracing growth Follow Asia on LinkedIn: https://www.linkedin.com/in/asiaorangio/  Check out DemandMaven: https://demandmaven.io/  Check out Asia’s newsletter, The Work by DemandMaven: https://demandmaven.substack.com/  — Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    54 min

  3. AUG 1

    #56 The Mason Cosby Route

    In this episode, Scrappy ABM founder Mason Cosby talks about his unexpected journey from side hustle to multi-million-dollar business owner—all sparked by a desire to help his wife stay home with their newborn. Mason shares how an early $25K win in March 2023 snowballed—leading to $2.5M+ in revenue within just two and a half years—and how he’s scaling Scrappy ABM without debt, cold outreach, or compromising on his values. Mason reflects on the chaos of working 120-hour weeks with a postpartum partner, the painful lessons from firing seven contractors, and the shift from being the brand to building a team that can thrive without him. He also opens up about turning down a $6–7 million acquisition offer in pursuit of a bigger mission: equipping a million marketers with repeatable ABM playbooks by 2035. (00:00) Intro (00:29) Starting the solopreneur journey (00:53) Early successes and challenges (02:32) Transitioning to a real business (05:27) Scaling with contractors and employees (09:43) Lessons in hiring and growth (23:31) Scaling out for paternity leave (24:41) Hiring the right people (28:20) The role of a coach (31:11) Building a support network (35:23) Mason’s future goals and vision Follow Mason on LinkedIn: https://www.linkedin.com/in/masoncosby/  Check out Scrappy ABM: https://scrappyabm.com  — Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    44 min

  4. JUL 25

    #55 The Tiger Joseph Route

    In this episode, brand director and filmmaker Tiger Joseph shares his path from cold-pitching clients on Twitter at 17 to building a content strategy consultancy rooted in creative alignment. Tiger reflects on his early work in the manosphere and internet marketing circles, the pivot from video production to advisory, and the mental toll of running a client-heavy agency. Tiger recounts how filming a documentary during El Salvador’s national election reshaped his perspective on freedom, control, and purpose. Tiger also explores how meditation, solitude, and refining his services helped him break away from burnout and reconnect with the kind of work that energizes him. He emphasizes the value of listening to your resistance, trusting your inner direction, and designing a business that supports both creative expression and long-term sustainability. (00:00) Intro (01:23) Building brands with transitioning founders (05:25) The reality of solopreneurship (09:50) The move to LinkedIn (13:45) The El Salvador documentary (17:57) From production to consulting (21:04) The challenges of agency work (26:10) Principle-based thinking in content strategy (27:50) The reality of YouTube (28:16) Execution and sustainability in content creation (29:39) Leveraging teams for content creation (31:04) The role of consultants and mentors (33:13) Balancing art and client expectations (35:00) Reflecting on past mistakes (36:03) The importance of meditation (39:32) Finding your flow in business (45:08) Avoiding hustle culture Follow Tiger on LinkedIn: https://www.linkedin.com/in/tigerjoseph/ Check out Tiger’s official website: https://tigerjoseph.com/  -- Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    52 min
  5. #54 The Justin Blackman Route

    JUL 18

    #54 The Justin Blackman Route

    In this episode, brand voice expert Justin Blackman discusses his journey from working with major corporate brands to becoming a successful solopreneur. Justin reflects on his early freelancing attempts in 2014, the initial failures, and his return to stability with IHG. He recounts how a project writing 10,211 headlines in 100 days significantly impacted his career but also strained his personal life. Justin explores the importance of therapy and mindset work in overcoming self-doubt and establishing a successful business helping entrepreneurs define their personal brands. He also emphasizes the importance of balancing professional ambitions with personal well-being. (00:00) Intro (01:09) Early freelance struggles (03:48) The 100 headlines project (06:24) Personal sacrifices and lessons learned (11:11) The turning point of mindset and therapy (16:08) The freedom of solopreneurship (21:26) The essence of brand voice (22:56) The challenge of deep thinking (27:24) The journey of iterations (29:50) The burden of success (33:17) Separating personal from professional success Follow Justin on LinkedIn: https://www.linkedin.com/in/justinblackman/  Check out Justin’s official website: https://justinblackman.com/  -- Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    44 min
  6. #53 The Sarah Brooks Route

    JUL 11

    #53 The Sarah Brooks Route

    In this episode, Sarah Brooks, founder of Website Mirror, shares her journey from freelance generalist to focusing on her signature website writing process. Sarah talks about how her "Website Mirror" offer came into focus, reflecting her unique process and how it helps clients stand out in a saturated market. She also discusses her early days of freelancing, navigating the pressures to take on any work, and the mental blocks she overcame to niche down and charge more for what she truly enjoys. Sarah emphasizes the power of authenticity and how being clear about the problem she solves has led to better connections with clients. She offers insight into building a business that balances creativity, authenticity, and growth. (00:00) Intro (00:29) Meet Sarah Brooks: Founder of Website Mirror (00:44) The challenges of freelancing (01:29) Breaking free from unwanted work (03:25) The power of networking and referrals (04:54) Overcoming mental blocks (07:20) The importance of authenticity online (09:13) Launching and evolving the Website Mirror offer (10:18) Balancing work and personal life (18:57) Adapting and customizing services (23:30) Navigating market pressures (25:30) Acquiring first customers (26:01) Building in public strategy (26:10) Client success stories (27:39) The power of specificity (29:08) Affinity and trust in business (31:08) Reframing the offer (33:23) The credibility trap (38:40) Identifying the core problem (41:52) The importance of a good website Follow Sarah on LinkedIn: https://www.linkedin.com/in/sarah-brooks-12b04b21/ Check out the Website Mirror: http://www.sarahbrookswrites.com -- Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    50 min
  7. #52 The Lashay Lewis Route

    JUL 4

    #52 The Lashay Lewis Route

    In this episode, Lashay Lewis, founder of BOFU.ai, shares her powerful story of building a life and business from the ground up. From launching Amazon affiliate sites as a teenager to earning passive income off YouTube videos, Lashay reveals how small wins and painful rejections rewired her thinking and shaped her entrepreneurial journey. She talks about growing up in Baltimore, the role her husband played in supporting her early efforts, and the inner fire that drove her to master bottom-of-funnel content after being rejected from a dream job. Lashay also discusses balancing business with raising four kids, how trauma can fuel transformation, and why becoming the “poster child” student helped her stand out and build a category-defining consultancy.  (00:00) Intro (03:19) The blessing of not knowing how hard it would be (06:14) Making her first online income (07:58) Affiliate marketing on YouTube (10:17) Building while raising two kids (12:04) Escaping “just good enough” as a solopreneur (15:00) Learning to sell through local SEO work (16:51) Selling websites too cheap (and learning from it) (18:16) Transitioning into B2B and failing a big opportunity (19:11) Creating the Content Dashboard (22:37) The mentorship that changed her life (26:57) Becoming known for BOFU.ai (30:03) What really motivates her (35:11) Always investing in herself (44:18) Entrepreneurship as a lesson for her children Follow Lashay on LinkedIn: https://www.linkedin.com/in/lashaylewis/ Check out BOFU.ai: https://bofu.ai/ -- Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    53 min
  8. #51 The Kendall Cherry Route

    JUN 27

    #51 The Kendall Cherry Route

    In this episode, Kendall Cherry, founder and executive ghostwriter at The Candid Collective, discusses her unconventional journey from a high-flying corporate role to a thriving solopreneur. Kendall recounts her decision to leave HP, her initial attempts at career coaching, and the fast pivot to ghostwriting that resulted in a 10K month almost immediately. She talks about the challenges of balancing creativity with business management and the impact of hiring an operations strategist to streamline her workflow. Kendall also shares her thoughts on the "starving artist" narrative and the importance of creating a sustainable and meaningful business. Reflecting on her branding success with the sunflower motif, Kendall underscores the value of authenticity and aligned action in attracting and retaining clients. (00:00) Intro (00:46) Kendall’s shift from corporate to entrepreneurship (01:57) Lessons from Kendall’s first business attempt (04:04) Writing as a transformative tool (07:33) Debunking the starving artist myth (09:24) Challenges of running a service-based business (12:22) The importance of client retention (18:32) Navigating business pivots (23:50) Operational strategy for scaling (37:01) Balancing client work and workload (39:14) Effective marketing for service providers (39:48) The power of asking for help (41:31) Using a gated services guide for growth (43:02) Client success stories and their impact (49:48) Investing in learning and growth (58:06) Writing that resonates with readers (01:02:41) Building a personal brand Follow Kendall on LinkedIn: https://www.linkedin.com/in/kendall-cherry/  Check out The Candid Collective: https://candidcollective.co  -- Create your next digital offer: https://harnessandhone.com/  Join How Solos Scale: ​​https://www.howsolosscale.com/  Download the free roadmap: https://fullstacksoloroadmap.com/

    1h 12m
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Ratings & Reviews

5
out of 5
4 Ratings

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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