I Have Some Questions...

Erik and Molly dive into the real skill behind “speaking up” and why organizations fail: they don’t have an accurate shared reality—essential to actually make the best decisions, execute, and deliver great outcomes. Molly shares a simple, flexible framework that all professionals can apply: “Me–You–We” and explains how leaders and teams can create mutual understanding, hear tough truths, and turn communication into trust and faster execution.

👤 About the Guest

Molly Tschang is a founder of Abella Ventures and Say It Skillfully. With 80+ M&A experiences at Cisco and US Filter, she...

Erik and Jason Lauritsen dig into what “connection” really means at work, what drives it, and how it translates into motivation, performance, and retention. Jason shares findings from the Human Connection Study, including why “resonance” with purpose can matter more than human-to-human rapport.

👤 About the Guest

Jason Lauritsen is CEO of Connected Performance Group and an advisor to leaders who refuse to choose between results and people. He developed Connected Performance Systems and helped publish the Human Connection Study, based on 286,000+ employee responses across 1,600+ organizations. He also authored Unlocking High Performance and speaks on cultivat...

🧠 Erik’s Take

Erik framed the episode as a leadership question, not a political one: how to lead people who genuinely disagree without losing the thread of what actually matters. He kept coming back to a quiet but demanding discipline, holding convictions while staying curious enough to notice what his own first instincts miss. He also noticed how often organizations confuse novelty for progress, especially in education, and how that pattern can steal attention from fundamentals like reading, math, and attendance.

🎯 Top Insights from the Interview

Michael’s school-improvement philosophy centers on...

🧠 Erik’s Take

Erik treats this episode as a strategy debrief, not a tech demo. The part that stayed with him is that AI adoption often fails when businesses chase automation before they diagnose the real bottleneck. He also reflects on how consulting handoffs, while efficient at scale, break down for founder-led companies. That framing leads to his bigger, more vulnerable point: leadership change is about redesigning work without accidentally taking away the experiences people need to grow, make judgment calls, and build trust.

🎯 Top Insights from the Interview

Smaller business...

Michael Summers shares how he went from professional musician and third-generation business owner to a politics-and-education leader, and why his north star is replacing fear with wisdom. From school board chairing during COVID to running for Oregon House District 53, he argues that bridge-building, disciplined priorities, and the “main thing” mindset can help communities disagree well and deliver better outcomes.

👤 About the Guest

Michael Summers is a Central Oregon business owner and community leader with deep ties to Redmond. Before politics, he played drums professionally and has led a third-generation flooring business. He chaired the Red...

Drew Mehta explains why so many “AI strategies” fail in practice, and why owner-operators need end-to-end workflow decomposition, not deck-first consulting. We dig into the difference between consultants and builders, the “garbage equation,” and why AI should be used to fix weeks-long process bottlenecks, not just minutes of work.

👤 About the Guest

Drew Mehta is an AI and product builder with 20+ years of experience creating data, analytics, and AI products for Major League Baseball, KKR, and PepsiCo. He founded ThinkFraction to help small owner-operated businesses ship AI-enabled improvements by decomposing workflows, measuring impact, and pairing...

Erik walked away from his conversation with Shawn Busse thinking less about technology itself and more about what it actually takes to create something new inside a business.

Shawn described business as “the hardest art project ever,” and the idea stuck. Artists create through experimentation: they make something, react to it, change it, throw pieces away, and keep going. Businesses call those same behaviors prototyping, testing, iteration, and product-market fit.

The tension is that businesses eventually become very good at doing something else: execution. They optimize processes, improve margins, create predictability, and protect what already work...

Shawn Busse argues that “growth marketing” hits an inherent ceiling when it becomes a commoditized, copyable process. He uses Hotelling’s law and the “Google beach” to explain why competitors converge, prices collapse, and differentiation fades. The antidote is creative, cross-functional marketing that also shapes product, pricing, and delivery.

👤 About the Guest

Shawn Busse is the founder of Kinesis, a Portland growth studio helping businesses compete on creativity instead of conformity. A former sculptor and art professor, he later built businesses through making, teaching, and practicing creative problem-solving. His contrarian thesis: most companies over-rely on...

🧠 Erik’s Take

Erik frames this as a short, high-leverage review of his conversation with Wanda Herndon, using her career as a mirror for a recurring workplace pattern: people who are ready to grow run into organizations that only know how to say “no.” What stays with him is Wanda’s ability to treat rejection as information, not identity. He also leans into the nuance that her story is not a simple “leave when it’s hard” message. It asks harder questions about timelines, internal opportunity, and what companies owe when they actually see someone’s potential but fai...

Wanda J. Herndon shares how her commitment to telling the truth guided her through corporate PR, and how she navigated being stifled by “sure things” in old-guard companies before helping build Starbucks into a global brand. Her memoir, *Working Class to Breaking Glass*, connects leadership, belonging, and resilience.

👤 About the Guest

Wanda J. Herndon is an award-winning communications executive, author, and trailblazer. Best known as Starbucks’ first SVP of global communications, she rose through Dow Chemical, DuPont, and Starbucks, and authored the memoir Working Class to Breaking Glass. Raised in Flint, Michigan, she brings a...

Justin Coates, co-founder of LearnAir, demos ChatGPT’s new always-on, voice-driven AI agents (Dots) and the “Space” work hub, and explores what changes when work becomes something you can direct and supervise while you are actually living your life.

🧭 Conversation Highlights

Dots and related always-on agents connect to your digital work stack, so they can keep working using context from what you’ve linked.The episode centers on real demos: updating a podcast run-of-show doc, fixing broken integrations, and using voice to manage tasks without being chained to Slack.Justin shows how “Space” becomes a single collab...

Erik and Alli talk about why “retirement someday” is losing its grip. With a changed job market, uncertainty about longevity, and shifting priorities, professionals are choosing to live now while still building careers.

🧭 Conversation Highlights

The “traditional” retirement script is breaking as jobs feel less stable and outcomes feel less predictable.Alli frames urgency around real experiences and the fact that you may not get to retirement, even if you plan for it.People are balancing ambition and life by reshaping work, not quitting it outright: flexibility, boundaries, and roles with less trade-off.Alli and Erik po...

🧠 Erik’s Take

Erik’s takeaway is that the market for expertise is changing at the same time as the meaning of expertise itself is changing. He came away focused on a single tension: companies used to buy expertise by buying time and employment, but fractional models buy judgment and embedded execution. Then AI enters the picture and compresses the value of “competence as content,” forcing the human edge to shift toward judgment, context, and trust. He also flags something personal: he’s noticed that the things that work least in theory are often the ones he can s...

Fractional leadership is exploding for good reasons: shifting career expectations, cost optimization, and companies needing C-suite strategy without permanent headcount. Natalie Hoop breaks down how fractional differs from consulting and contracting, why ROI can be dramatic for clients, and how fractionals themselves must think and operate like business owners to price, position, and build a reliable pipeline.

👤 About the Guest

Natalie Hoop is a fractional COO and coach for fractional leaders. Based in Columbus, Ohio, she went fractional in 2023 after an unexpected layoff, quickly delivering major sales growth. After losing her mom and reb...

Erik and Justin dig into whether today’s AI risks are being overstated by headlines, and what a practical approach should look like for pacing, alignment, and cybersecurity hardening as AI agents grow more capable.

🧭 Conversation Highlights

Erik challenges the “frontier labs prove everything is catastrophic” framing, arguing that real-world harm requires unusual capability, access, and resources.Justin counters with a “toy rocket vs frontier rocket” analogy: risk is real, but the systems most people can use are typically nerfed, tested, and guarded.They unpack the Hugging Face incident, reframing it as an agent exploiting th...

Alli explains why leaders feel terrified about “getting their life back,” and how to work the problem underneath the tactics. Her framework is the four Rs: reveal the rules and beliefs under the behavior, reset through small experiments that teach the nervous system it is safe, rebuild your operating system, and reclaim capacity at work and outside of work.

🧭 Conversation Highlights

The fears leaders have are rarely just logistical. They are usually “rules and beliefs” that predict consequences like being seen as a poor teammate, missing goals, or facing a PIP.Alli frames reset as a nervou...

🧠 Erik’s Take

Erik treated the episode like a credibility audit disguised as a payments breakdown. On the surface, it was about how card transactions get approved. Underneath, it was about earning the right to sit in the middle of something high-stakes, then compounding that trust into real business leverage over years.

🎯 Top Insights from the Interview

“Buy Now” looks instant to the customer, but it is really a rapid negotiation between merchant, processors, banks, card networks, and multiple risk systems to prevent fraud and errors.Infrastructure businesses can be meaningfully...

🧠 Erik’s Take

Erik frames the episode as a short, reflective review, but the real throughline is how self-trust shows up when the stakes are real. He notices that the conversation with Colby did not stay confined to business, content, clients, or relationships. Instead, it circled a deeper question: what changes in a person’s life or work when they decide their own judgment has to matter.

🎯 Top Insights from the Interview

Colby’s courage standard is not “Did every decision work?” but “Did I act on what I honestly believed at the ti...

Danny Chazonoff, an OG of online payments, breaks down why “Pay Now” is really a high-stakes, multi-handshake system. From early online gambling and wallet innovations to issuer-acquirer conversations, fraud controls, and chargeback risk, he explains how payment processors built infrastructure for speed, trust, and reliability. He also shares the mindset that helped his teams scale and diversify into a multibillion-dollar outcome.

👤 About the Guest

Danny Chazonoff is President/COO and co-founder of KORT Payments. He has decades of experience building and scaling specialized payment infrastructure, including founding roles in early online wallet solutions, and a t...

Colby Wegter shares how he grew audience and trust without “performing,” why he thinks the customer must lead marketing, and how he rebuilt his life around gut-driven decisions. From agency ethics and “winning the first 48 hours” to parenting as repair work, he ties everything back to self-trust, discernment, and never outsourcing belief.

👤 About the Guest

Colby Wegter is a former agency operator and newsletter writer who helps people who “look good on paper” but feel hollow. After serving 1,200+ clients, he stepped back to rebuild a life aligned with his values, centering self-trust, candid reflection, and...

Justin Coats joins Erik for another take of their weekly issue of the AI Questions section. This time, joined as well by Rebecca Maloney, Director of IT at Hayden Homes. She shares how they drove real AI adoption by starting with process and culture, building governance and training before expanding tools, and using human conversations to unlock faster handoffs across the home-building chain.

🧭 Conversation Highlights

AI adoption at Hayden started with where work is getting duplicated across handoffs, not with chasing an AI feature.Clean data and clean process matter equally, otherwise dashboards and aut...

Erik and Alli Murphy reunite after a month-long hiatus and dig into why high-performing women (and increasingly everyone) are moving toward “analog” habits. They connect the trend to burnout fatigue, attention capture from devices, and a desire for creativity and real presence, then unpack what boundaries look like in practice without harming career momentum.

🧭 Conversation Highlights

Alli describes the push toward paper books, printed recipes, and even flip phones as a reaction to constant connectivity and the “infinite workday.”They compare two approaches to boundaries: external forcing functions (brick phones, screen blockers) versus internal experiments...

🧠 Erik’s Take

Erik treated this as a short, high-signal recap of his deeper conversation with Logan Yonavjak, but the “takeaway” that kept reappearing was about measurement itself. He realized the real question was not only how to measure leadership readiness, but how easily businesses confuse what they can measure with what they actually need. He also connected Logan’s product challenge to a broader selling problem: you cannot move past the analytics until the customer agrees the underlying concept is measurable and meaningful.

🎯 Top Insights from the Interview

Businesses lean on proxie...

Logan Yonavjak and Erik unpack why leadership “readiness” has been so hard to assess, and how Readiness Engine connects leadership traits like capacity, strategy, and adaptive intelligence to outcomes teams can act on. They discuss why traditional assessments fail (static, self-reported snapshots), the role of shared language, coaching interventions, and how product and category differentiation matters in crowded markets.

👤 About the Guest

Logan Yonavjak is co-founder and CEO of The Readiness Engine. She previously worked in institutional investing across climate and natural capital strategies, and now focuses on leadership intelligence that links measurable readine...

Shawn Busse, founder of Kinesis, explains how his studio arts background shaped his approach to innovation, marketing, and business resilience. We connect art and entrepreneurship through ideation, prototyping, and iteration. Then we dig into why “creativity” gets crushed by measurement and attribution, how to lead with kindness and still tell hard truths, and why the next era requires “innovate it out” instead of waiting out disruption.

👤 About the Guest

Shawn Busse is the founder of Kinesis, a Portland-based growth studio that helps businesses compete on creativity instead of conformity. He brings a contrarian perspective...

Erik and Justin unpack why the “AI wrote it” controversy hit so hard, and what “human-in-the-loop” should realistically mean going forward. They land on traceability, disclosure, and an explicit “human floor” rather than moral panic or blind purism.

🧭 Conversation Highlights

They separate the question of content quality from the authorship and disclosure expectations behind high-trust publishing.Justin argues responsible AI use is fine when the human guides, edits, and owns the intent, but he dislikes copy-paste AI delegation.Erik pushes toward a falsifiable standard: traceability and audit logs that prove what human direction happened and when.They c...

🧠 Erik’s Take

This short review episode stayed with Erik because Vincent holds two truths that usually get treated as opposites. Vincent is relentlessly optimistic about what people can do, while also being blunt about reality. Erik hears that as a philosophy of ambition that refuses entitlement. The episode is not really a victory lap about hustle. It is a conversation about what happens when someone wants big things and then does the unglamorous work of making “possible” less abstract. Erik’s own takeaway is that optimism only becomes durable when it gets tethered to specifics a...

Vincent Van den Broeck, founder of the UID Club and author of Everything Feels Impossible Until It’s Done, shares how hospitality sparked his creative drive, and how a life-threatening accident became a mirror for building resilience, non-negotiables, and daily “doing” instead of waiting for motivation. We explore grit, reframing failure, alignment in health and finances, and why believing “why not me” starts with accountability to yourself.

👤 About the Guest

Vincent Van den Broeck is an entrepreneur and hospitality veteran who built his life around creating and serving. After a near-fatal accident and a prolonged r...

Erik and Justin reset the conversation from AI tactics back to the “grand dream,” sharing optimistic, near-term business use cases, especially in healthcare and logistics/robotics.

🧭 Conversation Highlights

Erik and Justin contrast doom narratives about AI with what they see in adoption and day-to-day workflow changes.Justin argues healthcare will feel AI gains as improved care and reduced administrative friction, not mass job loss.They dig into the “separate human from digital” idea: let AI handle the repeatable work so humans can focus on human-to-human moments.They look beyond software to physical-world impacts, from robots that...

Asher Albertini, an 18-year-old high school senior and former LearnAir intern, shares what AI has changed for him in school, friendships, and career thinking, and how his generation should prepare for a future where entry-level work gets redefined.

🧭 Conversation Highlights

AI detectors and grading: detectors are often inaccurate and only really target essay-style work, while better approaches include timed writing and drafts/version history.Entry-level roles are changing: Asher sees AI taking “mundane” tasks and raising the bar for critical thinking, strategy, and communication.AI literacy training is a missed step: companies often buy tools a...

With Erik out, Justin Coats steps into the host chair for a conversation with veteran creative Carl Loeb about what happens when generative AI enters the creative process—and why the answer isn’t to resist it or surrender to it.

Carl draws on nearly 40 years in advertising, branding, and technology to make the case that AI is an extraordinary thinking partner, but humans still bring something essential to the work: taste, discernment, emotion, ownership, accountability, and lived experience.

The challenge isn’t simply learning how to use AI. It’s learning where AI belongs in the p...

🧠 Erik’s Take

Erik treated the episode like a “numbers as a compass” field guide. What stayed with him wasn’t finance trivia, it was the discipline of turning ratios and variances into sharper questions. He also realized he keeps circling the same leadership test: when the diagnosis is uncomfortable, will the organization change its behavior, or will it protect the old pattern?

🎯 Top Insights from the Interview

Personnel is not just a cost line. It is a signal of whether the company is investing in human capital well, especially when benchmark...

🧠 Erik’s Take

Erik frames this as more than a communications discussion. The real question, for him, is timing: how fast a company can learn what it is, how it should describe itself, and whether the rest of the business is ready to absorb the attention that message creates. He admits he initially pushed back on starting comms on day one, because in his own founder journey the language was never “clean” immediately. But he lands on a sharper principle: comms is not decoration. It is an iteration engine that accelerates the clarity loop between what the...

Scott Lauray shares how ProVia Partners helps middle-market owners make confident financial decisions, from business valuation to M&A advisory and fractional CFO work. He connects enterprise value with real owner goals, and frames business success as an engine for opportunity across employees, families, and communities.

👤 About the Guest

Scott Lauray is founder and principal of ProVia Partners, delivering business valuation, M&A advisory, and fractional CFO support for privately held companies. After leadership roles in large international organizations, he shifted in 2010 to focus on the entrepreneurial middle market and build guidance tailored to...

Erik talks with Joshua Altman about why communication gets “random acts” treatment, and how fractional chief communications officers bring strategy and consistency without full-time cost. Joshua shares two core frameworks, Story-Narrative-Brand and the Four Languages (read, see, hear, experience), plus why trust, authenticity, and even lighting and audio matter for message delivery.

👤 About the Guest

Joshua Altman is an experienced storyteller and strategist who leads Beltway Media, a DC-based communications firm. With over two decades of experience, including multimedia journalism at The Hill covering high-stakes federal policy and elections, he now helps startups and age...

Justin Coats breaks down the idea of “super apps” for AI and what that really means for corporate adoption, change management, security, and tokenomics.

🧭 Conversation Highlights

Justin defines super apps as AI workspaces that combine model access, agents, and computer or browser use in one interface.Erik pushes on the human side of adoption and asks whether waiting for the tech to mature actually reduces the real cost.They discuss how change management needs education, executive buy-in, and AI champion teams that represent more than just IT.Justin explains context windows (AI attention span) and the...

🧠 Erik’s Take

Erik treated this as a compact leadership debrief, not just a recap. The uncomfortable through-line for him was the idea that forward movement can come from releasing control, even when his natural instinct is to define the result, set the plan, and solve the problem. He keeps circling back to three tensions Jaclyn named: letting go is a skill, specificity can become a ceiling, and early goals can manufacture clarity without actually creating it. He also noticed something personal while reviewing the episode: high-performing patterns are often strategies to avoid feeling first, and t...

🧠 Erik’s Take

Erik treats this “short review” as a real question, not a tech demo. The core shift for him is moving from AI personalization as memory, to AI personalization as understanding: a predictive model of how a specific person learns, gets stuck, adapts, and responds. He also feels the conversation complicate the regulation instinct. It is not just “should we regulate,” but “who gets to decide what these tools can do” and what values get embedded. Finally, he leaves with a more intellectual spark: if AI can model people well enough, it could turn theories of...