1,000 Routes with Nick Bennett

In this episode, consultant, speaker, and creator,  Heike Young , shares her journey from leading content teams at Salesforce and Microsoft to building her own business helping B2B brands create content through employees, customers, and creators. She reflects on leaving a successful corporate career, the desire for greater flexibility and ownership of her time, and how building an audience on Link...

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 transitione...

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...

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 explain...

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 t...

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...

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 dem...

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....

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...

In this episode, Evan Kubitschek, founder of The Ops Gap and Grow Rogue, shares how an unexpected layoff from Pendo pushed him into independent consulting. He talks through the moment he realized he had been laid off, why the severance gave him the runway to go all in, and how he quickly turned that opportunity into a real business. Evan also reflects on why the traditional path in operations was...

In this episode, Jessica Lackey, a business strategist and educator, shares her remarkable career journey from high-level roles at McKinsey and Nike to building her own thriving business. Jessica reflects on the turning point when she realized corporate life wasn’t for her, leading her to become an entrepreneur. She discusses the challenges of transitioning from corporate roles to consulting and h...

In this episode, Seth Waite, partner at Schaefer and former head of growth at a high-growth technology firm, shares his journey from law school dropout to building a thriving business. Seth discusses how his shift from corporate life to entrepreneurship was driven by a desire for freedom and solving customer problems. He reflects on the importance of staying hyper-specialized in business to maximi...

In this episode, Lee Densmer, author and content marketing strategist at Globia Content Marketing, shares her journey from 25 years in corporate to launching her own consulting business. After two layoffs, Lee turned a forced decision into her best move yet, leveraging her extensive network to build a solid client base. She discusses the challenges of transitioning from corporate life, the importa...

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...

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, pri...

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 co...

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...

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...

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...

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 husba...

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 balanci...

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 chr...

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...

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 episo...

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...