1,000 Routes with Nick Bennett

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 starting to feel less appealing, especially as senior roles pulled him further away from the systems work he enjoyed most.Evan also breaks down how he found his first clients, how he used experimentation to shape his business model, and what helped him avoid building a consulting practice that took over his life. He shares practical lessons on pricing, scope, pipeline, LinkedIn, and the value of protecting his time. Throughout the conversation, Evan makes the case that a successful service business is built less on follower count and more on clarity, consistency, and designing the business around the life you actually want.(00:00) Intro(00:30) Evan shares how he learned he was laid off(02:47) How severance gave him runway to try consulting(04:47) Why he chose going solo over in-house roles(07:03) How he landed his first clients and niche(13:02) Treating the business as a series of experiments(25:36) His daily pipeline-building routine(25:51) Using LinkedIn comments to start conversations(29:26) Cleaning up his LinkedIn network intentionally(33:20) Why follower count doesn’t equal revenue(35:50) Stop overthinking and test more ideas(39:08) Growing the business while protecting time(43:20) Reflections on growth and long-term prioritiesFollow Evan on LinkedIn: https://www.linkedin.com/in/evankubitschek/ Check out Grow Rogue: https://www.growrogue.com/ Check out The Ops Gap on Substack: https://theopsgap.substack.com/ —Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

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 how she leveraged her personal networks to build a successful business.Jessica also talks about her unique approach to business growth, emphasizing the importance of focusing on revenue first, rather than simply growing an audience. She explains how she deliberately optimized for profit and has continued to scale her business without relying heavily on social media or viral content. Jessica shares her thoughts on building authority over time, discussing how it takes years to establish a reputation that truly drives long-term success.(00:00) Intro(00:52) Two career-changing breaking points(01:07) Nike burnout story and realization(02:50) Rebuilding identity after corporate life(03:17) COVID wake-up call for Jessica(04:45) Side hustle reality: lessons learned(06:01) First clients acquired through networks(07:18) Juggling three part-time consulting gigs(11:01) Building authority through strong relationships(12:33) Developing an ecosystem of offers(16:25) Serving the mid-market for success(22:42) Prioritizing foundational business frameworks(26:15) Building a five-year business flywheel(43:13) Building authority takes time and consistency(46:44) Small audience driving big revenueFollow Jessica on LinkedIn: https://www.linkedin.com/in/jessica-lackey/Check out Deeper Foundations: https://deeperfoundations.com/—Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠ 

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 maximize value without falling into the trap of the "bloated agency" model, which often dilutes expertise and margins. Seth also talks about scaling his business, the challenges of rapid headcount growth, and how he built systems that allowed his small team to operate at the efficiency of a much larger agency.Seth recounts the acquisition of his previous company, the impact of COVID on his moving and storage startup, and how he pivoted quickly when faced with unexpected obstacles. As he looks ahead, Seth shares his plans for Schaefer’s future, focusing on the food and beverage sector to create more specialized, high-value services. He emphasizes the importance of surrounding yourself with entrepreneurial people and maintaining freedom in business. Seth's vision is to help the world feel "at home" by solving consumer problems with innovative solutions and building businesses that prioritize customer value over sheer scale.(00:00) Intro(01:14) Seth Waite leaves law school(02:11) Walmart agency strategy lessons(06:25) Going solo and first exit(08:34) Scaling with the acquirer’s help(15:24) Productizing services and nailing positioning(17:38) Jump to moving tech industry(21:05) AI-driven quoting and hypergrowth(28:01) Next AI venture and new pivot(32:05) Partnering with Sydney for Schaefer(34:21) Pivot to food and beverage brands(36:23) Lean team advantage in business(40:52) Scaling with systems and efficiency(45:25) Business valuation and exit strategies(53:56) Lessons learned on staying focused(59:13) Last meal on earthFollow Seth on LinkedIn: https://www.linkedin.com/in/sethwaite/Check out Schaefer: https://schaefer.co—Build a repeatable inbound motion and stabilize your revenue: ⁠https://duoconsulting.co/⁠Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​⁠https://www.howsolosscale.com/⁠

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 importance of strategic networking, and the highs and lows of consulting. Lee reflects on her first three years, exploring how she adapted her offerings to better align with what she truly loves.She reveals the evolution of her business model, moving from long-term retainers to shorter, more agile sprints, and the growing pains that come with a successful but shifting business. As Lee navigates the transition from being a sole consultant to running a content-driven business, she delves into her latest venture: launching a course alongside her book and consulting. Lee talks about how an accidental audience on LinkedIn became one of her greatest assets, providing a solid foundation for her next steps. She also shares her lessons learned on scaling, trusting the process, and finding fulfillment in the work.(00:00) Intro(03:02) No plan, just freedom(04:56) Landing first clients(06:06) When the network dries up(07:50) Evolving offers and retainers(10:34) Strategy vs. execution debate(14:20) Building a partner bench(20:56) Never stop biz dev(24:31) Productizing the offer(26:32) Firing bad fit clients(31:20) Mexico sparks book idea(36:50) Book costs and payoff(43:43) Business regrets and outsourcingFollow Lee on LinkedIn: https://www.linkedin.com/in/leedensmer/Check out Globia Content Marketing: https://globiacontent.com/—Build a repeatable inbound motion and stabilize your revenue: https://duoconsulting.co/Each week, we share a new framework, concept, or example of how solopreneurs are scaling from $25,000 to $60,000+ per month: ​​https://www.howsolosscale.com/ 

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 projectsFollow Marc on LinkedIn: https://www.linkedin.com/in/iammarcthomas Check out Positive Human: https://www.positivehuman.co/ Check out Tinyseed: https://tinyseed.com/ —Create your next digital offer: https://harnessandhone.com/ Join How Solos Scale: ​​https://www.howsolosscale.com/ Download the free roadmap: https://fullstacksoloroadmap.com/

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 growthFollow Asia on LinkedIn: https://www.linkedin.com/in/asiaorangio/ Check out DemandMaven: https://demandmaven.io/ Check out Asia’s newsletter, The Work by DemandMaven: https://demandmaven.substack.com/ —Create your next digital offer: https://harnessandhone.com/ Join How Solos Scale: ​​https://www.howsolosscale.com/ Download the free roadmap: https://fullstacksoloroadmap.com/

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 visionFollow Mason on LinkedIn: https://www.linkedin.com/in/masoncosby/ Check out Scrappy ABM: https://scrappyabm.com —Create your next digital offer: https://harnessandhone.com/ Join How Solos Scale: ​​https://www.howsolosscale.com/ Download the free roadmap: https://fullstacksoloroadmap.com/

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/

In this engaging discussion, brand voice expert Justin Blackman reflects on his evolution from working with corporate giants to thriving as a solopreneur. He shares the pivotal moment of writing over 10,000 headlines and the personal sacrifices that accompanied this intense project. Justin emphasizes the importance of mindset, therapy, and balancing ambition with well-being. With insights into personal branding, he explains how vulnerability can enhance authenticity in communication, all while adding a fun twist with a light-hearted pizza debate.

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/