1,000 Routes with Nick Bennett

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 growthFollow 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/

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 visionFollow 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/

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 cultureFollow 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/

In this engaging discussion, brand voice expert Justin Blackman reflects on his evolution from working with corporate giants to thriving as a solopreneur. He shares the pivotal moment of writing over 10,000 headlines and the personal sacrifices that accompanied this intense project. Justin emphasizes the importance of mindset, therapy, and balancing ambition with well-being. With insights into personal branding, he explains how vulnerability can enhance authenticity in communication, all while adding a fun twist with a light-hearted pizza debate.

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 websiteFollow 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/ 

Lashay Lewis, founder of BOFU.ai, shares her inspiring journey from a challenging upbringing in Baltimore to becoming a B2B SaaS entrepreneur. She reveals how early experiences with affiliate marketing and YouTube fueled her resilience. Lashay discusses balancing her career and raising four kids, the impact of her husband's support, and how rejection drove her entrepreneurial spirit. She also highlights the mentorship that transformed her perspective and her passion for mastering bottom-of-funnel content to help others succeed.

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/