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 ...
Aug 08, 2025•54 min
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 pa...
Aug 01, 2025•44 min
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, ...
Jul 25, 2025•52 min•Ep. 55
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 establ...
Jul 18, 2025•44 min
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. S...
Jul 11, 2025•50 min
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-fun...
Jul 04, 2025•53 min
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 streamli...
Jun 27, 2025•1 hr 12 min
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 an...
Jun 20, 2025•54 min
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 ...
May 30, 2025•45 min
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 ...
May 23, 2025•56 min
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...
May 16, 2025•1 hr 5 min
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 Jos...
May 09, 2025•52 min
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 help...
May 02, 2025•51 min
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 ...
Apr 25, 2025•49 min
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 writ...
Apr 18, 2025•54 min
Devin Reed is a content strategist, solopreneur, and creator of The Reeder—a content consultancy and newsletter helping B2B brands stand out by owning a single word in their market. In this episode, Devin opens up about his journey from head of content at Gong and Clari to running his own business full-time. He shares the mindset shift that helped him overcome self-doubt, the moment he realized VP life wasn’t for him, and how he designed an intentional business with built-in client graduation. D...
Apr 11, 2025•50 min
Jay Acunzo is a keynote speaker and storytelling coach to business storytellers & experts, helping them compete on the impact of their ideas, not the volume of their marketing. In this episode, Jay unpacks the reality behind his transition from working at brands like Google, HubSpot, and NextView to going solo. He explains why he didn’t “make the leap,” how he replaced hustle with systems, and how an offhand compliment from a stranger helped him realize the value of his voice. Jay also share...
Apr 04, 2025•59 min
Chris Marr is the founder of The Authoritative Coach, a practice dedicated to helping coaches and consultants become trusted experts in the eyes of their clients. In this episode, Chris shares his journey from entrepreneur to employee and back again. He talks about how The Authoritative Coach started as an experiment, how he knew it was time to leave his job, and how he signed his first clients without even having a website. Chris also discusses the value of iteration, the importance of asking f...
Mar 28, 2025•57 min
Sean Blanda is the owner of Gate Check Studios, providing fractional brand, content, and marketing leadership for startups. In this episode, Sean shares his journey from journalism to entrepreneurship, his experience as a founding marketer at Crossbeam, and why he ultimately chose to go solo. Sean discusses the creative exhaustion that led him to take the leap, the importance of adapting to shifts in marketing, and how his sabbatical-inspired newsletter helped him reconnect with his creative ins...
Mar 21, 2025•41 min
Ramli “RJ” John is the founder of Delight Path, helping B2B companies optimize product onboarding to drive growth. In this episode, Ramli shares his journey from working in-house to launching his own consulting business, how writing a book changed his career path, and the lessons he’s learned in solopreneurship. He breaks down the mental shifts required to go from employee to business owner, the challenges of pricing and selling high-ticket services, and why structured processes make all the dif...
Mar 14, 2025•50 min
Andrew Capland is a coach and mentor of growth leaders, an advisor for product-led SaaS companies, and the host of the Delivering Value podcast. Andrew is on a mission to revolutionize his business and build a media empire. In this episode, Andrew shares his transition from a corporate role at companies like HubSpot, Wistia, and Postscript to becoming a solopreneur driven by passion and purpose. He also touches on the highs and lows of entrepreneurship, dealing with not-so-great clients, and the...
Mar 07, 2025•1 hr 8 min
Connor Lewis is the owner and creative director of Studio Lewis, specializing in B2B video ads for Series A and B SaaS companies. In this episode, Connor shares his journey from tax accounting to video production, the leap from in-house to solopreneurship, and how he scaled from $130K to $400K in a year. Connor breaks down the mindset shift from freelancer to business owner, the power of niching down, and the importance of building a community. He also reveals how strategic collaborations led to...
Feb 28, 2025•46 min
Aaron Reeves is the founder of Outbound OS, a solopreneur business that helps SaaS sellers book more meetings by providing them with proven frameworks and systems. In this episode, Aaron shares how he transitioned from working in-house to going fully solo, why he chose a membership-based business model, and the strategies he’s used to scale his community and revenue. He breaks down the challenges of pricing, the role of content in driving traffic, and how he’s built a sustainable business that g...
Feb 21, 2025•48 min
Hiba Amin is a fractional marketer and content consultant who helps startups craft impactful, scalable content strategies. In this episode, Hiba shares her path to solopreneurship, including the burnout that led her to rethink her career and the serendipitous events that helped her land her first clients. She dives into her approach to building strong content foundations (her “Shrek” analogy for using AI in marketing is unforgettable), navigating the emotional challenges of remote consulting, an...
Feb 14, 2025•46 min
Chris Dubois is the creator of the Dynamic Agency Operating System and a consultant who helps agencies go to market with clarity and focus. In this episode, Chris shares his journey from the military to marketing, leading an agency as CEO, and eventually building his own solopreneur consulting business. Chris opens up about the pivotal moments that shaped his career, including a health crisis that forced him to rethink his priorities and inspired his mission to help others design businesses that...
Feb 07, 2025•51 min
Erica Schneider is a content strategist, editor, and entrepreneur who has built a thriving solopreneur career by embracing vulnerability and authenticity in her writing. In this episode, Erica discusses her journey from ghostwriting to building her own voice and audience. She shares insights on creating engaging content, leveraging social platforms, and navigating the highs and lows of solopreneurship. Erica delves into the importance of building trust through transparency, the challenges of bal...
Jan 31, 2025•1 hr 1 min
Anna Furmanov is the founder of Furmanov Marketing Consulting, a strategy firm focused on helping startups and growth companies leverage deep customer insights to drive their positioning and messaging. In this episode, Anna shares her unconventional path from B2C to B2B marketing and her eventual leap into solopreneurship. She talks about how her background in consumer insights shaped her unique approach, the challenges of transitioning into tech startups, and the pivotal moment that led her to ...
Jan 24, 2025•45 min
Chris Bogue is a video coach and entrepreneur who transformed his skills in comedy and storytelling into a successful business. In this episode, Chris shares his journey from corporate sales to teaching solopreneurs and teams how to leverage the power of video. He discusses the process of finding a niche, creating an impactful course, and using humor to make his content accessible and memorable. Chris dives into why video remains a critical tool for B2B sales, how to craft content that truly con...
Jan 17, 2025•54 min
Joe Daniels is the founder of LEFTFIELD, a consultancy that helps businesses in crowded markets stand out through strategic positioning, branding, and messaging. In this episode, Joe shares his journey from agency work to running his own consultancy. He shares lessons on niching down, productizing services, and navigating the early challenges of building a personal brand. Joe opens up about his decision to rebrand his business, the concept of “Problem Access Fit,” and how embracing the path of l...
Jan 10, 2025•44 min
Tas Bober is the founder of Delphinium, a niche digital marketing consultancy specializing in paid ads landing pages for growth-stage B2B SaaS. In this episode, Tas shares her journey from being an in-house marketer to carving out her niche in landing page optimization. She talks about the challenges of niching down, the power of leveraging a unique personal brand, and how her “Scroll Lab” business evolved to serve high-performing SaaS teams. Tas reveals insights into creating scalable processes...
Jan 03, 2025•58 min
