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 how relationship-driven outreach, a simple LinkedIn launch post, and a creative research report helped him secure his first clients quickly and validate his business model.

Logan dives deep into his unique approach to webinar-led growth, explaining how he turned webinars into both a lead generation engine and a scalable media asset. He shares how he built a flywheel by combining content, audience building, and client delivery into one system allowing him to generate results for clients while simultaneously growing his own audience and pipeline. Throughout the conversation, Logan unpacks lessons on positioning, leveraging existing skills, building in public, and creating a service that doubles as a “permissionless demo” of your expertise.

(00:00) Intro

(01:00) Getting laid off → becoming an entrepreneur

(03:00) Landing first clients through network

(06:00) Using survey to to generate content and pipeline

(10:00) Why his outbound didn’t feel like outbound

(14:00) Content as a networking tool (events & outreach

(20:00) Choosing webinars as his core offer

(23:00) The 2-step signup that 5x’d conversions

(30:00) Building a media + service flywheel

(36:00) Differentiation through audience ownership

(40:00) What he’d do differently + scaling challenges

Follow Logan on LinkedIn: https://www.linkedin.com/in/loganlyles/ Check out DemandShift Summit: https://www.linkedin.com/company/demandshift-summit/

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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, 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 demand. Mike breaks down his core philosophy that category comes first, explaining why most founders struggle with positioning, how labels like “fractional” commoditize your value, and why defining your own category is key to standing out.

He also shares how he bootstrapped a podcasting business during COVID and used it to build relationships before transitioning into strategy. The conversation dives into his “movement to contact” approach to sales, focused on volume, consistency, and reps, and why learning sales early is critical. Mike emphasizes the importance of strong point of view, clear language, and consistent content, and shares his vision for adversarial go-to-market, built on one truth: the market owes you nothing and you have to earn every customer.

(00:00) Intro

(02:00) Starting a nonprofit boxing gym

(05:42) Why businesses fail

(07:04) Discovering category design

(10:15) Why “fractional” is a trap

(11:41) Spotting emerging markets

(16:34) Getting first clients

(20:04) Bootstrapping a business

(24:07) Red team and positioning process

(30:51) Lead generation and sales system

(38:18) Developing a strong point of view

(46:38) What’s next: adversarial go-to-market

Follow Mike on LinkedIn: https://www.linkedin.com/in/iron-mike-steadman/Check out OP4: https://op4.co

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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, 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. He also talks about the lessons learned from burning out in his first agency and how he found his true passion in marketing, which ultimately shaped his business philosophy.

Louis explores his Everyone Hates Marketers podcast experience, where he emphasizes the importance of standing out in a crowded market by being unapologetically authentic. He shares his unique approach to positioning, go-to-market strategies, and creative differentiation in a noisy world. Throughout the conversation, Louis opens up about his entrepreneurial highs and lows, his time at Hotjar, and how his personal health challenges influenced his career, providing invaluable insights on growing a business based on values and the power of embracing failure.

(00:00) Intro

(01:49) Tech boom and serendipity shaped career

(04:10) Why he chose to stay in Dublin

(05:24) First real marketing role and lessons learned

(06:30) Launching agency and early mistakes made

(08:02) Cancun burnout after failed client experiment

(10:06) Hotjar role and podcast beginnings

(16:34) First sales and early business anxiety

(20:46) Current revenue streams and business model

(22:06) Cutting business branches to refocus growth

(25:07) Doubling down on B2B GTM consulting

(28:35) Generosity over metrics drives real growth

(30:46) Beta readers improved book quality massively

(31:54) Book became powerful sales engine

(36:19) Cancer diagnosis brought clarity, not change

(40:38) Regrets about past relationships and growth

(41:25) Pruning business to focus on one thing

Follow Louis on LinkedIn: https://www.linkedin.com/in/louisgrenierCheck out Everyone Hates Marketers: https://www.everyonehatesmarketers.comCheck out Stand The F*ck Out: https://www.stfo.io

—

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/⁠