1,000 Routes with Nick Bennett

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 true validation, and the four-day surge that took doopoll from 1.6M to 16M votes—and nearly torched the company with usage-based bills.

He and Nick dig into the solopreneur head-game: optionality vs. salary, why Marc would take less money for more freedom, and how “punk” DIY energy: charisma, coaching, and seeing work through end-to-end wins in growth. Marc shares candid reflections on confidence dips, building pipeline without becoming your own worst client, and a pragmatic cash-flow system that lets him sleep at night while he eyes a return to software on his own terms.

(00:00) Intro

(00:29) Starting as a freelance journalist

(01:58) Creative gigs lead to a voting tool idea

(03:48) Building doopoll in four days

(04:19) Landing a 25k deal on the spot

(07:01) Fundraising before validation

(08:51) From 1.6M to 16M votes and server crashes

(10:32) Choosing stability and leaving doopoll

(17:22) The banker vs. taxi driver analogy

(20:52) Taking less money for more freedom

(26:18) Emotional whiplash of solopreneurship

(27:00) Lifecycle email and intersecting skills

(30:26) Punk marketing and DIY growth

(33:29) Learning charisma and coaching clients

(43:24) Cash-flow forecasting and personal runway

(45:39) Pipeline focus and new software projects

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 growth

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 vision

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 culture

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 success