1,000 Routes with Nick Bennett

Devin Bramhall is a growth advisor for startups and marketing agencies. In this episode, Devin shares her insights on making bold pivots, how a bout with cancer reshaped her perspective on work and life, and how her experiences as a woman in tech strengthened her commitment to supporting others in the industry. She also discusses building a business life aligned with personal goals, advocating for...

Tim Davidson is the founder of B2B Rizz, a LinkedIn ads and ABM consulting firm for B2B SaaS companies. In this episode, Tim shares his journey from working in an agency to going solo as a consultant, revealing the surprising benefits and challenges of being a solopreneur. He talks about the freedom and flexibility he gained, as well as the pressures of managing everything independently. Tim also...

Kory Kirby is a publishing strategist who helps experts write and publish books people actually read.  In this episode, Kory shares his journey from biking down the US West Coast to becoming a successful publishing strategist, showing solopreneurs how to build a business that aligns with their lifestyle. After self-publishing a book inspired by his travels, he learned by doing until he got an unex...

The “Consultant’s Consultant,” Max Traylor, gives us another round of unfiltered (maybe slightly unhinged) advice on solopreneurship, pricing, referrals, and inbound marketing. In this episode, Max discusses his transition from conventional agency methods to a more relationship-driven approach, offering insights into how solopreneurs can grow client accounts, tackle mental blocks, and communicate...

Brendan Hufford is the Founder of Growth Sprints and he helps SaaS companies scale from 10 to 100 million in revenue through content.  In this episode, Brendan shares his candid journey from a $50K salaried teacher to building a successful business in content marketing and software. Along the way, he reveals the brutal effects undue stress had on him and the reasons why his work is so meaningful t...

Two of Christopher G. Fox’s biggest wins looked like giving up from the outside. Christopher is the managing partner at Ideas Led Growth, but he started out in academia before shifting to consulting. In this episode, he uncovers his transition strategies, overcoming academic burnout and leveraging thought leadership to cultivate long-term client relationships. This conversation explores how Christ...

Shannon Curran, founder of SSC Consulting and a Fractional CMO, has a dream of what her life will look like and is building her work around that. In this episode, Shannon opens up about her transition from full-time roles to a fractional CMO determined to balance life and work on her terms. From navigating organizational changes post-maternity leave to defining her niche in the crowded fractional...

Garrett Jestice, founder of Prelude Marketing, hit a wall of burnout that spurred a dramatic career shift. In this episode, Garrett talks about his journey from a marketing leader in early-stage B2B software companies to thriving as a solopreneur, navigating the difficult path of client acquisition and scaling a business without scaling time. Garrett shared his insights for solopreneurs on honing...

Ryan Baum is a growth consultant and content strategist who's redefined his path in the solitude of solopreneurship. In this episode, Ryan shares his unconventional journey, battling the fast-paced tech industry's "build the plane as you fly it" mentality, and finding clarity through authentic connections and an ADHD realization. From LinkedIn ghostwriting to the intricacies of content operations,...

Tommy Walker is the founder of The Content Studio and he develops content programs for high growth startups and Fortune 1000 enterprises. In this episode, Tommy shares the struggles he faced, from living in a boarding house with a cracked laptop to scoring a life-changing business opportunity with LinkedIn. He reflects on the highs and lows of transitioning from freelancing to roles at CXL and Sho...

Devin Pickell is a solo content and SEO strategist who took the leap into entrepreneurship after being laid off during the 2023 tech layoffs. In this episode, Devin reflects on his journey from working with big names like G2 and Nextiva to building his own business. He shares the challenges of going solo, the importance of building a reputation versus a personal brand, and how he navigated the ups...

Bobby Gillespie is the founder of Propr, an advisory and creative services agency he’s run for nine years - he’s currently transitioning to being 100% solo. In this episode, Bobby reflects on his journey from running an agency to becoming a solo entrepreneur. He shares his emotional challenges, the pressures of market demands, and the transition to advisory and consulting work. Discover Bobby's ra...

Dylan Ciaccio is the Marketing Director of Black Camel Agency and the host of the B2B Strategy Podcast. In this episode, Dylan talks about transitioning from running the experiment of running something on his own to going back in-house. Dylan shares his insights on aligning incentives, the importance of marketing the problem, and establishing "problemotional advertising." He also opens up about ov...

Thom Van Dycke is a certified StoryBrand Guide and business consultant who went through a rocky transition from ministry to entrepreneurship in the midst of the pandemic. In this episode, Thom opens up about overcoming imposter syndrome and the initial struggles of securing contracts, to eventually becoming a successful coach for solopreneurs. (00:00) The importance of sales in business (02:00) Tr...

Melanie Deziel is the co-founder of the Creator Kitchen, an author, and a self-described forever student who’s learned a lot in nearly a decade of building a business around herself. In this episode, Melanie reveals her journey from New York Times big wig to solopreneurship, opening up about the fear of quantifying her worth and navigating business propositions. Melanie discusses her pivot towards...

Erin Balsa is the founder of Haus of Bold, a content marketing strategist, solopreneur, and mother of three.  In this episode, Erin shares her journey from SEO-focused writer to thought leadership advocate, the struggles of battling increased competition and dropping lead volume, and the ingenuity behind creating her on-demand course library.  Nick and Erin talk about the mental toll of solopreneu...

Bridget Poetker is Founder of Bridget Poetker LLC as well as Founder of Outside, a marketing consultant collective. In this episode, Bridget shares her journey from ad agency life to falling into tech marketing, the turbulence of layoffs, pay cuts, and finally taking a chance on herself to become a full-time solopreneur. Nick and Bridget discuss the frustrations of finding the right clients, the i...

Jed is a writer, creator, and founder of Practical Prospecting, a consulting firm that helps startups create outbound systems that consistently generate qualified meetings. In this episode, Jed shares his journey from SDR to entrepreneur and what he's doing to overcome the anxiety and limiting beliefs that come with it all. -- Follow Jed on LinkedIn Subscribe to the Practical Prospecting Newslette...

Justin Simon is a content distribution and repurposing consultant and the founder of Distribution First, a membership and community dedicated to helping burned-out marketers escape the content production trap. In this episode, Justin shares his journey from content marketer to entrepreneur and the challenges he faces while on his path to building a business he loves. (00:00 From Content Marketer t...

Chris Marr has devoted thousands of hours to coaching individuals and companies from startups to 7 and 8-figure enterprises and recently started a coaching firm of his own to help others become truly indispensable. In this episode, Chris shares how his journey from entrepreneur, to employee, back to entrepreneur has shaped the way he approaches his work and his life. (00:00) - Discovering the Joy...

Renee Frojo is a creator and independent content marketing strategist who helps founder-led businesses build brands that connect with people through content. In this episode, Renee talks through the route she’s carved from journalist to creator and shares the challenges, risks, and rewards she's experienced as a long time solopreneur. (00:00) - Finding Confidence in Past Successes (01:20) - From J...

Dan Sanchez is a marketing and audience growth consultant and the host of the AI driven marketer podcast. In this episode, Dan shares he used early buyer feedback to iterate on his offer and establish his footing as a solopreneur. (00:00) - The Leap (01:35) - From Sweetfish to Solo (04:19) - The Challenges of Remote Management and Cultural Fit (06:41) - A Vision for Content Marketing (08:51) - Hig...

Kaylee Edmondson has spent years as an in-house marketer and leading some of the most legendary demand teams in tech. Now, she is a marketing solopreneur and the founder of Demand Loops. In this episode, Kaylee shares how a cold DM changed her life and allowed her to carve her own route as a solopreneur. (00:00) - The Cold DM That Changed Everything (01:15) - Kaylee's Uncommon Journey in Tech and...

Erica Schneider is the founder of Cut the Fluff, a writing and editing coaching and consulting firm and seltzer fanatic. In this episode, Erica shares how a challenge to start writing online changed her life and allowed her to carve a route from content marketer to full-time Solopreneur. (00:00) - Intro (01:09) - Meet Erica (02:25) - The Power of Words (03:30) - The Art and Science of Content Mark...

John Rougeux is a narrative designer and the founder of Flag & Frontier . John shares the route he carved from mechanical engineer, to marketer, to category designer, to solopreneur. (00:00) - Embracing the Entrepreneurial Journey: A Personal Reflection (00:55) - Discovering The Route (01:10) - Networking and Learning in Business (03:00) - The Solopreneur's Mindset (07:48) - Finding Your Motiv...