Podcast
HabitStack Podcast
Hosted by Scott Ward · EN
Join us for honest, informal conversations with startup and agency founders who are deep in the trenches, actively growing their businesses.
Instead of glorified success stories, we share authentic experiences about the ongoing battles, everyday wins, and relatable struggles.
Perfect for entrepreneurs navigating the challenging middle stage of growth, this podcast offers real insights and genuine advice from peers who are right there with you.
24episodes
Episodes
Newest firstAll episodes
Bookkeeper, Controller, or CFO? How to Know Which One Your Business Needs
3w ago01:17:38Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward sits down with Josh Leyenhorst, fractional CFO and founder of BasePoint, to break down the financial frameworks that help founders run smarter businesses.Josh breaks down the difference between bookkeeping, controller work, and CFO-level thinking, framing them as hindsight, insight, and foresight, and explains why even founders who think their books are clean often have messy data driving bad decisions. He introduces a reverse-engineering framework that starts with a founder's personal life goals across five areas (faith, family, fitness, fun, and finance), converts them into a monthly cash requirement, and works backward to determine exactly what the business must generate in revenue and which specific levers to pull to get there.Josh also unpacks a vested profit sharing model as an alternative to equity, explaining how it creates long-term employee alignment without giving away ownership or control, and explains why overpaying good people is often cheaper than losing them. He addresses financial shame directly, noting that many outwardly successful companies are quietly struggling, and why naming that reality is often the first step to fixing it.Tools from Josh Leyenhorsthttps://www.basepoint.ca/toolshttps://www.youtube.com/watch?v=c9kOU_dHoUU
Transcribe →Get Out of the Weeds: Laura Pitsch on Building a Business that Runs Smoothly
Apr 2301:13:46Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Laura Pitsch, a fractional COO who works with founder-led businesses navigating the messy middle between startup chaos and scalable operations. Laura explains why the $3 to $4M revenue range is where businesses most commonly stall and why founders who avoid investing in operational leadership rarely make it to the next level. She breaks down the real difference between an executive assistant, a chief of staff, and a COO, and why misunderstanding these roles leads to expensive mismatches. Laura shares her framework for helping founders get out of the day-to-day: identifying key functional leaders, assigning two to three accountability metrics per area, and running leadership meetings where real conversations actually happen. They also dig into feedback culture, why founders avoid it, why that avoidance compounds over time, and a simple daily habit that starts shifting the dynamic immediately. Laura also makes a case for doing fewer things better, and why throwing headcount at a messy operation just makes the mess more expensive.
Transcribe →Stop Being the Bottleneck: Keegan Sard on Delegation and Decision-Making
Apr 900:41:41Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Keegan Sard, a fractional chief of staff based in Monaco who has been doing fractional work for 10 years. The conversation explores the critical difference between a chief of staff and a COO, and why chiefs of staff focus on the founder's priorities without P&L responsibility. They discuss why founders should hire fast and fire faster instead of endless interview rounds, and the distinction between executive assistants who manage calendars and chiefs of staff who make strategic decisions on the founder's behalf. Keegan explains decision playbooks for empowering teams without bottlenecking the founder, quick wins like eliminating payroll from the founder's plate and conducting calendar audits, and implementing the Ritz Carlton's $2,000 rule where every employee can spend money to fix problems without approval. They dive into why founders should include bad news in investor updates to get help before it's too late, the importance of listening tours in the first 90 days, and why anonymous feedback reveals customer insights that never make it up the chain.
Transcribe →B2B Storytelling and Team Empowerment: Alisa Manjarrez on Stories Bureau's Evolution
Mar 1000:39:44Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Alisa Manjarrez, managing director of Stories Bureau, a creative agency focused on B2B marketing and internal corporate storytelling through presentations, videos, and podcasts. Alisa shares what she's learning from Multipliers by Liz Wiseman about scaling herself as a leader. The conversation explores how Stories Bureau evolved from presentation design for market research professionals at companies like Mars Wrigley into narrative podcasts and video production. They discuss why small companies should ignore advice to be on every social platform and instead master one channel at a time, while leveraging the research behind Fortune 500 messaging strategies for their own audiences. Alisa explains why podcasting isn't going out of style despite the average podcast getting only 30 listens, how 1,000 listens puts you in the top 10%, and why podcasts are the new book as proof of expertise. Alisa shares how she's repositioning Stories Bureau to lead with relationship-driven partnership rather than just showcasing work like competitors.
Transcribe →Writing for Humans and Machines: Belinda DiGiambattista on Growing Good2bSocial
Feb 2400:39:07Tap to summarizeScott Ward interviews Belinda DiGiambattista, CEO of Good2bSocial and founder of Choose Your Metric. Belinda shares her entrepreneurial journey from Fortune 500 financial services to building Butter Beans, a school lunch company she grew from zero to 5,000 lunches a day before selling in 2017, and how those lessons shaped her consulting work and eventual acquisition of Good2bSocial, a digital marketing agency serving the legal industry. The conversation explores Belinda's philosophy that every business needs one primary North Star metric that drives decisions and eliminates distraction. Belinda explains how her non-digital marketing background gives her a beginner's mind advantage, helping her team focus on actionable insights rather than raw data. They dive into leadership development through training, delegating with trust, and using mission, vision, and core values as a decision-making framework that scales culture without requiring the founder to be involved in everything.
Transcribe →VR Training and Wildly Important Goals: Rami Kalla on Building Point In Time Studios
Feb 300:40:00Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Rami Kalla, president and founder of Point In Time Studios, an VR/AR production company. Rami shares how Point In Time creates VR training experiences for first responders and TSA agents in life-or-death situations where officers can practice handling bomb threats and other dangerous scenarios. They discuss Rami's transition from artist to business leader after meeting Tony Robbins, realizing he was the constraint as the company tried to scale, and implementing a hybrid of EOS and Scaling Up frameworks with daily huddles, weekly L10 meetings, and annual summits. Rami explains why he added the Four Disciplines of Execution's concept of Wildly Important Goals to rally his team around single objectives like increasing gross profit or landing a Super Bowl commercial, and how this laser focus helped them achieve national spots on MSNBC and CNN.
Transcribe →Betting on Human Writers: Brent Peterson’s Contrarian Move
Jan 2100:37:45Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Brent Peterson, CEO of Content Cucumber, president of Content Basis, and host of the Talk Commerce podcast. Brent shares his contrarian bet that human writing will make a comeback after AI decimated the content industry, explaining how he bought Content Cucumber because professionals increasingly value human-created content over AI-generated material. They discuss the advantages of productized services with flat monthly pricing that makes it easy for clients to start without scoping complexity. Brent reveals his new tool that helps writers match client brand voice by analyzing content and scoring how well it aligns. On the leadership side, they discuss business operating systems, quarterly goal setting, and strategy execution rhythms.
Transcribe →From Event Coordinator to Agency CEO: Wendy Covey's Journey Building TREW Marketing
Jan 1400:37:59Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Wendy Covey, CEO and co-founder of TREW Marketing, author of Content Marketing Engineered, and podcast host. Wendy shares how TREW Marketing pivoted during the 2008 financial crisis from serving diverse clients to specializing exclusively in marketing to engineers, leveraging her 15 years at National Instruments to create an advantage in a crowded market. The conversation explores how AI is transforming their technical content development through research augmentation and persona testing rather than replacing writers. They discuss Wendy's philosophy of controlled growth at 15-30% annually to maintain work-life balance and team retention, her mistake of creating a separate brand for educational content that caused confusion and inefficiency, and the lessons from over-hiring based on optimistic revenue projections. Wendy explains how their annual State of Marketing to Engineers research report became a credibility-building engine that informs strategy and generates endless repurposed content. They dive into implementing EOS-light with L10 meetings and rocks, the importance of assigning accountability to avoid unforced errors.
Transcribe →Event Optimization, Learning Styles, and a Big Pivot with Bernadette Burke of Brella
Dec 1700:43:26Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Bernadette Burke, President of Brella Productions, an event optimization agency that helps organizations maximize return on event (ROE) through strategic audience experiences. Bernadette shares what she's learning from rereading Brain Rules by John Medina about neuroscience and communication, and why the research on learning styles isn't holding up the way people think. The conversation explores Brella's transformation three years ago from a generalist communication company doing video, graphics, and app development to specializing exclusively in live event experiences. They discuss why most organizations fail to think through return on event beyond just wanting people to have a good time, how Bernadette asks strategic questions about downstream effects that often catch clients off guard, and the importance of finding quantifiable indicators even for squishy goals. Bernadette explains her philosophy on event design covering every stage from pre-event gamification to post-event memory triggers that keep energy going for months. They dive into Brella's efforts to bring focus after decades of entrepreneurial chaos, how they navigated inflection points at 10, 25, 50, and nearly 100 employees, and the importance of responding to team discomfort with curiosity instead of defensiveness.
Transcribe →Scaling Marknology Through Tough Times: Andrew Morgans on E-Commerce, AI, and Goal Setting
Dec 1600:44:26Tap to summarizeIn this episode of the HabitStack Podcast, host Scott Ward interviews Andrew Morgans, CEO of Marknology and founder of EcomPulse.Ai, who also hosts the Business Therapy podcast. Andrew opens up about navigating a difficult 2025 for his 11-year-old agency, dealing with rising costs, client churn, and macro challenges like tariffs and inflation. The conversation explores why Andrew brought in a fractional CFO and the difference between that role vs. a bookkeeper vs. an accountant. Andrew shares his journey from growing up in Africa to accidentally becoming an entrepreneur, how his sisters joined him in year three and remain with the 28-person team today, and why the transition to 10 employees was monumental because it required developing communication skills that didn't come naturally. They dive into Andrew's philosophy of running on habit, and setting attainable goals that build momentum. The episode covers the challenge of attribution in modern e-commerce where customers see ads on TikTok but buy on Amazon, why blended returns across channels matter more than isolated metrics, and how Andrew lost the Startup Hustle podcast when his mentor's company sold but is now launching the Business Therapy podcast on his own terms.
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