Most B2B founders want to scale revenue, but they still run sales like the company cannot close a deal unless the founder is involved in every conversation.

In this episode of Life's a Pitch, Jared Gibson sits down with Alex Newmann, founder and CEO of Newmann Consulting Group. Alex helps B2B founders transition out of founder-led sales and build scalable, repeatable sales systems that drive predictable revenue.

They unpack why founder-led sales becomes a bottleneck, what it actually costs a growing company, and why the first sales hire often fails. Even talented reps struggle when onboarding is unclear, expectations are undefined, and there is no repeatable sales process in place.

Alex explains how to successfully transition out of founder-led selling without removing the founder from revenue entirely. The goal is not to eliminate founder involvement, but to build a sales team and go-to-market strategy that can operate without the founder touching every deal.

The conversation also dives into:

• Why hiring big-company reps into early-stage startups often fails

• How to build a repeatable B2B sales process

• What proper sales onboarding should actually look like

• How to scale a sales team without creating chaos

• Why video and audio outreach outperform cold email in today's outbound environment

Alex shares why LinkedIn video outreach and short audio messages are generating faster replies than traditional cold email, and how founders and sales teams can implement this immediately.

The episode wraps with rapid fire moments including Krav Maga discipline, skiing as a founder reset, and why reflection and journaling are underrated performance tools for entrepreneurs.

Key Takeaways:

✅ How to move out of founder-led sales the right way ✅ Why most first sales hires fail at startups ✅ How to build a scalable B2B sales system ✅ What a real sales onboarding process looks like ✅ Why video outreach works better than cold email ✅ How to remove the founder bottleneck without hurting revenue

Connect with Alex Newmann Guest LinkedIn: https://www.linkedin.com/in/alexnewmann/ Website: https://www.alexnewmann.com/

This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

A lot of companies struggle to explain what they actually do, even when they're good at it.

This episode of Life's a Pitch with Aimee Schuster digs into that exact problem.

Aimee is a founder and marketing leader who works with B2B companies, often in professional services and SaaS, helping them clarify their message, rebuild their marketing systems, and scale growth in a way that actually matches how buyers make decisions. We talk about why marketing isn't a single fix, why tools don't magically solve positioning problems, and why consistency, quality, and authenticity matter more than shortcuts.

The conversation also touches on how marketing has changed in the last year, especially around SEO and AI. Aimee breaks down why fundamentals still matter, why good content has to work for both humans and machines, and why increasing frequency without sacrificing substance is where most teams get stuck.

Layered into that work is Aimee's role as an angel investor and member of the Josephine Collective. We talk about how access, not capital, is often the biggest barrier for women in investing, why writing a first check matters, and how being closer to founders has shaped how she evaluates companies and advises clients.

It's a practical conversation about growth, risk, and building systems that actually hold up.

Connect with Aimee Schuster Guest LinkedIn: https://www.linkedin.com/in/aimeeschuster Website: https://www.bandwidthstrategies.com

This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Most agency owners say they want predictable growth, but they still run their business like it's powered by luck, referrals, and a few warm intros that may or may not show up.

In this episode of Life's a Pitch, Jared Gibson sits down with Chris DuBois, founder of the Dynamic Agency Operating System. Chris helps agency owners break referral dependence, stop duct taping their business together, and build a business that can grow intentionally without the founder doing everything.

They unpack why most agencies avoid the real constraint in their business, which is demand. Instead of building pipeline, many founders procrastinate by optimizing SOPs, cleaning up delivery, or tightening internal systems while leads stay inconsistent. Chris breaks down his "problem marketing" approach, why buyers act on symptoms before they recognize the true problem, and how agencies can position around the problem so clearly that prospects assume you have the solution.

Chris also shares an Army-derived planning framework, the green pen, red pen, blue pen strategy, as a simple way to map the market, understand competitors, and build a plan with contingencies. The conversation hits on cohort-based coaching, why community accelerates progress, and why context matters when taking business advice instead of copying a guru playbook.

The episode wraps with rapid fire moments, including kettlebell obsession, scary life stories, ChatGPT as the solopreneur advantage, and why Teddy Roosevelt might be the most intense beer conversation of all time.

Key Takeaways:

✅ Why referral reliance creates feast or famine growth ✅ How to market to symptoms so buyers recognize the real problem ✅ Why demand is the constraint most agencies avoid ✅ The green pen, red pen, blue pen framework for strategy and positioning ✅ Why context matters more than tactics when taking advice ✅ How cohorts create faster growth than solo execution

Connect with Chris DuBois Guest LinkedIn: https://www.linkedin.com/in/christopherrdubois/ Dynamic Agency OS Website: https://dynamicagencyos.com/ Agency Forward (Newsletter): https://agencyforward.co/

This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

Most founders know they need a go-to-market strategy, but very few understand when founder-led selling should evolve into a real revenue engine, or how personal brand fits into that transition.

In this episode of Life's a Pitch, Jared Gibson sits down with Jess Schultz, founder of Amplify Group, fractional CRO and CMO, former venture capitalist, and active angel investor. Jess works with B2B startups navigating founder-led sales, early revenue growth, and the shift from scrappy execution to scalable systems. The conversation also touches on building a business while navigating new motherhood and why patience becomes a strategic advantage for long-term founders.

Together, they unpack when founders should and should not hire their first salesperson, why most teams make that hire too early, and what founders can do from day one to prepare for a future sales engine. Jess breaks down the importance of call recordings, CRM discipline, and founder-led learning loops that turn real sales conversations into training, content, and leverage.

The episode also explores why founder-led content and personal brand accelerate trust in high-consideration B2B sales, especially for services and early-stage companies. Jess reframes visibility as service, not self-promotion, and explains how content becomes a scalable alternative to one-to-one relationship building. They also discuss the trade-offs between scalability and mission, why some businesses are inherently harder to scale, and how founders can create leverage without defaulting to headcount.

Key Takeaways ✅ When founders should transition from founder-led sales to hiring reps ✅ Why recording sales calls early creates long-term leverage ✅ How personal brand builds trust at scale in B2B services ✅ Why visibility feels uncomfortable but drives pipeline ✅The trade-off between scalability and staying true to your mission ✅ Why no business model is actually "easy"

Connect with Jess Schultz Guest LinkedIn: https://www.linkedin.com/in/jess-schultz (Amplify Group Founder & CEO) Instagram & Newsletter Links: https://linktr.ee/jessicatschultz Amplify Group Website: https://www.amplifyscales.com/

This episode is powered by Outworks. Outworks helps B2B companies build real, repeatable executive content engines through founder-led strategy, tight systems, and AI-powered content infrastructure designed to scale without losing authenticity.

Learn more at https://www.outworks.io

Most professionals talk about reinvention, but very few actually do it without burning bridges, blowing up their identity, or chasing the next shiny thing.

In this episode of Life's a Pitch, Jared Gibson sits down with James Hornick, former Chief Growth Officer at Hirewell and now an independent options trader specializing in systematic zero DTE strategies. James shares what it really looks like to evolve a career over 20 years, moving through recruiting, marketing, content, sales, and growth before making a deliberate exit from corporate life.

Together, they unpack why reinvention is a skill, not a crisis response, how James helped turn an entire company into content creators, and why leadership visibility is a prerequisite for any content strategy to work. James breaks down his philosophy on building systems, whether in business, content, or trading, and explains why writing is one of the most underrated tools for thinking clearly and leading effectively.

The episode also explores James's transition into systematic options trading, what zero DTE actually means, and why automation, data, and risk management matter more than prediction or gut feel. Throughout the conversation, they challenge common myths around passion, confidence, and success, and dig into what it takes to build something sustainable instead of performative.

You'll learn: ✅ How to reinvent your career without losing momentum ✅ Why employee-led content works when it's built on real questions ✅ The leadership requirement behind consistent company content ✅ What 0DTE options are and how systematic trading actually works ✅ Why writing makes you better at sales, marketing, and leadership ✅ How to use AI tools without outsourcing your thinking

Connect with James Hornick Guest LinkedIn: https://www.linkedin.com/in/james-hornick/ Substack: Zero Days to Give https://jameshornick.substack.com/

In this episode of Life's a Pitch, I sit down with Jen Guzman, founder of Bestola Consulting and one of the most no-BS operators in Chicago's small and mid-market business scene. Jen and I go back to our days working together in HR/marketing during the early COVID chaos, so we start with real stories about urgency, leadership under pressure, and what it looks like to serve clients when everything is on fire.

From there, we get into what Jen is seeing in Chicago civic leadership—not as a partisan argument, but as an "operating system" problem: underqualified leaders running massive budgets, voter apathy, and why "activism" isn't the same as "execution." Jen breaks down how organizations like Rise Chicago approached civic engagement like a business: listening tours, clear priorities, and building a "what matters" playbook that reflects what people actually care about.

We also go deeper into Jen's personal story—health battles, burnout, and a powerful realization that she's been trying to run an old playbook on a new operating system. She shares what it's like to build a company while re-prioritizing life outside of work, and why achievement can't be the only scoreboard.

On the business side, Jen explains how Bestola Consulting was born after her health wake-up call—clients started reaching out, asking for help with client experience, employee experience, retention, and hard conversations. That leads into one of the most practical parts of the episode: Jen teaches the 5-step framework for tough conversations (the exact tool we used in leadership training) and why avoiding conflict is how businesses quietly walk toward disaster.

You'll learn: ✅ Why leadership fails when people skip the "earned experience" phase ✅ How to build trust with a "what matters" playbook (in business and civic leadership) ✅ The 5-step framework for hard conversations that prevents blowups and drama ✅ The ugly truth about entrepreneurship (and why people should stop sugarcoating it) ✅ How to separate self-worth from achievement before life makes the decision for you

If you're building a business, leading a team, navigating tough conversations, or trying to grow without burning your life down in the process—this episode is a straight, honest conversation with a founder who's lived it.

Connect with Jen Guzman Guest LinkedIn: https://www.linkedin.com/in/jen-guzman/ Guest Website: https://www.bestolaconsulting.com/ Guest Email: [email protected]

Instagram: Bestola Collective

This has all been powered by Outworks. If you're a B2B company that wants to build a real, repeatable executive content engine (instead of outsourcing your voice to generic content), Outworks may be a fit. Everything you see in our podcast and content is built through founder-led strategy, tight systems, and an AI-powered content infrastructure designed to scale without losing what makes you you.

Learn more about services here: https://www.outworks.io

In this episode of Life's a Pitch, I sit down with John Tsourakis, co-owner of digital agency OYOVA and a multi-time founder who has built, scaled, and exited businesses across agencies, healthcare, and tech. We get into what it really looks like to run an agency today, why the model is tough, where founders get it wrong, and how acquisitions and focus can create leverage instead of more chaos.

John shares unfiltered stories about bad clients, setting hard boundaries to protect your team, and the leadership moments that cost money but save culture. We also talk sales the honest way, including cold calling, rejection, why doing the opposite of what gurus recommend often works, and how to stay sharp without burning yourself out.

We also dig into founder mindset, letting go of failures, knowing when to sprint versus recharge, and why resilience matters more than raw hustle over the long run.

You'll learn: ✅ Why the traditional agency model is under pressure ✅ How to spot and walk away from nightmare clients early ✅ What still works in sales when everyone is chasing digital tactics ✅ How strong boundaries create better teams and better businesses ✅ Why letting go is a real competitive advantage

If you're building or running an agency, leading a sales-driven business, or navigating growth with real people and real pressure, this episode offers an honest look at the realities most founders don't talk about.

Connect with Jon Tsourakis Guest LinkedIn: https://www.linkedin.com/in/jontsourakis/ Guest Website: https://www.oyova.com/

If you are a B2B company that wants to build a real, repeatable executive content engine instead of chasing random posts or outsourcing your voice to a generic agency, Outworks may be a fit for you. Everything you see in our podcast and content is built through founder-led strategy, tight systems, and an AI-powered content infrastructure designed to scale without losing your voice.

Learn more about services here: https://www.outworks.io