1,000 Routes with Nick Bennett

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 childrenFollow 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/ 

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 brandFollow 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/ 

In this episode, Emily Court shares her unconventional journey from freelance writer to brand and web designer for solopreneurs. She opens up about the career-altering conversation that inspired her to pivot into design, what it was like to land her first high-stakes client project, and how she built a booked-out business without relying on inbound leads. Emily also talks about working through chronic illness, why she never thrived in traditional jobs, and how solopreneurship gave her freedom and purpose. She unpacks the emotional and strategic layers of building a business that actually fits—and sustains—her life, and why helping others break free from broken systems fuels her every day. Plus, she teases what’s next: a productized offer and a podcast of her own.(00:00) Intro(01:06) From freelance writer to designer(02:32) The pivotal conversation with James Martin(06:50) Emily’s first major design client(09:33) Building credibility through public work(12:59) Managing growth and booking out(14:13) Client fit and discovery call red flags(20:30) The balance between style and flexibility(23:46) Lessons from cancer, chronic illness, and healing(28:00) Designing for people like her(30:25) Choosing meaning over scale(32:34) Why working with solos feels different(35:26) What Emily wishes she did sooner(40:22) Outbound strategy that saved her business(43:04) The power of short, human messages(46:33) Don’t make it weird: authentic outreach wins(48:16) What’s next: a podcast and productized service(53:22) Emily’s last meal on EarthFollow Emily on LinkedIn: https://www.linkedin.com/in/emily-court-website-copy-and-design/Work with Emily: https://www.emilycourt.ca/--Create your next digital offer: https://harnessandhone.com/ Join How Solos Scale: ​​https://www.howsolosscale.com/ Download the free roadmap: https://fullstacksoloroadmap.com/ 

In this episode, Jed Mahrle, founder of Practical Prospecting, unpacks the journey from sales manager to solopreneur: how he validated his business while still in a W-2 role, why he initially worked for free, and what gave him the confidence to charge. He shares how content became the engine for inbound opportunities, why he said yes to everything early on, and how he built multiple income streams—from consulting to affiliate deals to brand partnerships. Jed also reflects on what makes the work meaningful today, why freedom from “OPM” (other people’s meetings) matters, and what he hopes to build next beyond B2B sales.(00:00) Intro(02:09) From PandaDoc to Mailshake(02:38) The leap to solopreneurship(04:15) Building Practical Prospecting(05:17) The power of consistency and writing(13:24) Diversifying revenue streams(19:29) The role of content and sponsorships(24:34) Joining Sell Better(28:03) Challenges of starting a business(28:22) The stigma of going solo(31:58) Building in public and learning out loud(37:24) The fulfillment of helping others(42:44) Building a media companyFollow Jed on LinkedIn: https://www.linkedin.com/in/outboundsales/Subscribe to Practical Prospecting: https://www.practicalprospecting.io/--Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Sam Browne is a longtime entrepreneur, writer, and creator known for his unique voice and practical approach to personal branding. With nearly two decades of experience building creative businesses—from a chart-topping music career to a seven-figure wedding services agency—Sam now helps others grow their audiences and businesses through intentional content strategy and brand clarity.In this episode, Sam shares how he transitioned from the New Zealand music and events industry into a successful content-driven business on LinkedIn. He walks through the highs and lows of entrepreneurship, the systems behind his prolific content output, and the real reason he’s pivoting toward personal storytelling over algorithm chasing. Sam also dives into the evolution of his consulting and digital product business models, and how he’s building a new SaaS product from scratch—all while staying grounded in craft and integrity.(00:00) Intro(00:46) The shift to content creation(01:53) Balancing content and life(03:12) Content creation strategies(04:27) The Forever 50 system(11:29) Challenges of video content(16:20) Authenticity in content(18:24) Navigating LinkedIn success(23:35) The entrepreneurial journey(26:32) Transition to LinkedIn strategy(27:46) Starting a business from scratch(28:37) Building Findaband and Auckland Weddings(30:36) Challenges and lessons learned(32:06) Music career and entrepreneurship(35:17) LinkedIn journey and content creation(43:15) Private coaching and consulting(43:56) Evolving business models(48:10) Importance of building an email list(50:38) Upcoming projects and goalsFollow Sam on LinkedIn: https://www.linkedin.com/in/sam-browneBuilt a Profitable Personal Brand on LinkedIn with Sam: https://sam-browne.notion.site/Build-A-Profitable-Personal-Brand-on-LinkedIn-1aacfae6146d804fb435c79d1018ff48 --Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Andrew Capland is a growth strategist and founder of his own business, where he helps growth teams and entrepreneurs build scalable, efficient strategies. With years of experience in the growth space, Andrew now focuses on creating content and resources to empower others to navigate their professional challenges with actionable, repeatable frameworks.In this episode, Andrew shares his journey of transitioning from full-time employment to building his own business. He walks through his struggles and successes, from figuring out how to create content that resonates with his audience, to experimenting with pricing models for his new digital offerings. Andrew also reveals how he’s working to scale his income through sponsorships, while balancing the demands of fatherhood and entrepreneurship. Plus, he dives into the nuances of creating a digital product that can operate without him—designed to help others make decisions, take action, and achieve results.(00:00) Intro(01:00) Transition from full-time to solo business(05:15) Navigating self-employment challenges(09:40) Evolving content strategy and creating value(14:00) Exploring new income streams: sponsorships & digital products(18:25) Pricing dilemmas and thought process(22:05) Developing self-guided course & digital products(27:00) Balancing family life & entrepreneurship(31:20) Lessons learned and moving forward with clarity(36:10) Creating scalable business model that works without you(40:45) Thoughts on the changing role of digital products & content creation(46:00) How sponsorships align with passive income goals(50:05) Importance of experimenting with new business models(54:30) Challenges in building long-term business(59:00) Building business that works for your lifeFollow Andrew on LinkedIn: https://www.linkedin.com/in/andrewcapland/Check out Delivering Value: https://deliveringvalue.co/--Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Jen Allen-Knuth is a sales strategist, keynote speaker, and founder of DemandJen, where she helps teams simplify selling and rediscover the joy of driving meaningful conversations.In this episode, Jen opens up about the mindset shifts that finally pushed her to go solo after years at Challenger and Lavender. She shares the insecurities she had to overcome, the messy behind-the-scenes of setting up her business, and the surprising joys (and pains) of self-employment. From being called out by Josh Braun to forging a playful feud with Will Aitken on LinkedIn, Jen walks through the very real, very human story of building a solo business with staying power.(00:00) Intro(00:32) From Lavender to solopreneurship(03:05) Overcoming insecurities and taking the leap(06:05) Navigating LinkedIn and building a personal brand(09:07) Choosing a business model and early challenges(12:27) The turning point(15:47) Support from industry leaders(21:09) Balancing work and personal life(25:04) The reality of sales and entrepreneurship(26:25) Humor and content creation(28:24) LinkedIn dynamics and fake feuds(30:32) Transitioning from Lavender and finding new balance(31:40) Challenges of working independently(35:35) Navigating business logistics(46:50) Pricing and value realization(47:38) Lessons in business pricingFollow Jen on LinkedIn: https://www.linkedin.com/in/demandjen1/ Check out DemandJen: https://www.demandjen.com --Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Justin Simon is a content strategist, course creator, and founder of the Distribution First Academy, helping solopreneurs and marketers build smarter content engines without burning out.In this episode, Justin shares how a layoff became the unexpected push he needed to bet on himself—and why he’s focused on building a business he never wants to retire from. He opens up about navigating the messy early days of consulting, finding his niche in content repurposing, and the mindset shifts that helped him build a more sustainable, intentional career. From launching a course while still working full-time to taking a leap into coaching and community building, Justin traces the real, unfiltered path that brought him to today—and where he’s aiming next.(00:00) Intro(01:28) Creating the Content Repurposing Roadmap(02:52) Transition to solopreneurship(11:54) Early struggles and learning curves(19:22) Lessons from fractional roles(22:49) Balancing revenue streams(23:16) Building a membership community(26:25) The challenges of creating a membership(32:33) The impact of one-on-one coaching(37:58) Balancing personal and professional life(47:23) What Justin would’ve done differentlyFollow Justin on LinkedIn: https://www.linkedin.com/in/justincsimon/ Check out Distribution First Academy: https://distributionfirst.club/ --Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Renee Lynn Frojo is a writer, strategist, and former journalist who’s built multiple creative ventures—from food blogs to online magazines to a thriving content consulting business.In this episode, Renee shares why she’s walking away from one-to-one client work and betting big on herself (again). She opens up about evolving as a solopreneur, finding clarity through experimentation, and what it really takes to stay motivated when the initial spark fades. From a press badge in D.C. to building a food blog from scratch, Renee traces how every chapter of her career has uniquely prepared her to help others tell their stories—and now, to launch A Good Reputation, a new newsletter about building businesses with intention and integrity.(00:00) Intro(01:03) Getting traction on LinkedIn by breaking the mold(02:21) Why she stopped trying to be an “expert”(03:35) How Renee approaches honest writing(05:12) Writers she admires and what she’s learned from them(07:26) Going back to journalism roots(11:00) The turning point to go solo(14:06) Her first blog, Make It Like A Chef(15:42) Why 10K followers wasn’t enough(17:46) Selling Woman Born and entering consulting(19:44) Building a content business and evolving again(22:06) When discomfort means it’s time to pivot(24:05) The compounding value of all her projects(27:03) Launching A Good Reputation(29:31) Turning down clients to make space(32:28) Escaping the one-to-one “freelance trap”(34:08) Moving toward cohorts and courses(35:56) Making the leap (with a safety net)(43:00) Lessons she’d do differently(44:33) What she’s building nextFollow Renee on LinkedIn: https://www.linkedin.com/in/renee-lynn-frojo/Check out A Good Reputation: https://www.reneelynnfrojo.com/--Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/ 

Alice Lemée is a writer, strategist, and creator of Internetly, a newsletter exploring identity, creativity, and online business. In this episode, Alice opens up about the moment she realized freelancing wasn’t her long-term path, how she coined the concept of “Creator Gravity,” and why building something meaningful requires messy, unglamorous work behind the scenes. From a failed music internship during COVID to going viral on Twitter, Alice shares how she turned rejection into a full-time writing career—eventually building newsletters for top creators like Miss Excel and growing an audience of her own. (00:00) Intro(03:36) Discovering Medium and writing about scams(08:01) How a viral Twitter thread launched her freelance career(12:57) Landing early clients and building momentum(15:18) Creating value through curation, not expertise(20:06) The highs and lows of freelancing(23:54) Building Miss Excel’s newsletter from 50 to 392K(26:30) The power of relationships and personal brand(29:34) Launching Internetly as a creative outlet(31:58) Why Alice walked away from the digital nomad lifestyle(38:55) Coining “Creator Gravity” and building a new lens(46:03) The importance of commitment to the craft(48:30) Detaching from metrics and trusting the process(49:56) Letting go of a past identity to make room for what’s next(51:19) Building the Creator Gravity cohortFollow Alice on LinkedIn: https://www.linkedin.com/in/alicelemee/Work with Alice Lemée: https://www.alicelemee.com/Subscribe to Internetly: https://internetly.substack.com/--Create your next digital offer: https://harnessandhone.com/ Join Full Stack Solopreneur: https://fullstacksolo.com/Download the free roadmap: https://fullstacksoloroadmap.com/