1,000 Routes with Nick Bennett

Nick Bennett
undefined
Jul 25, 2025 • 52min

#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 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/
undefined
Jul 18, 2025 • 44min

#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 successFollow 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/ 
undefined
Jul 11, 2025 • 50min

#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 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/ 
undefined
Jul 4, 2025 • 53min

#52 The Lashay Lewis Route

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.
undefined
Jun 27, 2025 • 1h 12min

#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 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/ 
undefined
Jun 20, 2025 • 54min

#50 The Emily Court Route

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/ 
undefined
May 30, 2025 • 45min

Rerelease: #11 The Jed Mahrle Route

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/ 
undefined
May 23, 2025 • 56min

#49 The Sam Browne Route

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/ 
undefined
May 16, 2025 • 1h 5min

#48 The Andrew Capland Route (Part 2)

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/ 
undefined
May 9, 2025 • 52min

#47 The Jen Allen-Knuth Route

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/ 

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app