“Why do I have to tell your chatbot to do something? Just do it.”

In this episode, Jeff Seibert – founder of Digits (AI-native accounting platform), former Twitter Head of Product, and the engineer behind Crashlytics (now on 6 billion devices) – reveals what it actually takes to build AI-native companies from scratch. We explore why most companies are getting AI wrong by bolting chatbots onto old products, how to structure teams for extreme velocity, and why the accounting industry is about to experience its HP-35 calculator moment. Jeff’s bold prediction: the entire month-end close process will be automated within 12 months.

What You’ll Discover:

[02:45] Why Accounting Data Quality is Decades Behind Product Analytics → The genesis story of Digits: when Twitter’s 100-person finance team couldn’t answer a simple budget question in under three weeks

[08:28] Building Companies for AI From Day One → How ML-native architecture differs from traditional databases and why this matters more than the AI hype suggests

[10:31] The 65-Person Company That Runs All-Hands Every 48 Hours → Jeff’s radical approach to velocity: weekly sprints, fractal team structures, and why they’ll never hire “lone eagle” engineers

[15:20] Keeping Teams Intentionally Small at Scale → How to eliminate the “empire building” problem by dissociating engineering coaches from project staffing

[19:59] What CEOs Actually Do That AI Can’t Replace (Yet) → The 10%/90% leadership philosophy and why Sundar Pichai’s “AI will replace CEOs” take misses the point

[23:30] Disrupting QuickBooks: Technology vs. Distribution → Why accounting is uniquely suited for AI disruption and how startups can outpace 800-pound gorillas

[26:14] Why AI Isn’t Just Another Ajax Moment → The fundamental shift from “talk to our chatbot” to “the AI should just do it” – and what that means for software architecture

[30:47] The Architectural Wall Ahead for Large Language Models → Why current LLM architecture won’t reach AGI: the context window problem, lack of memory, and inability to backtrack during inference

[32:05] The Great Work Displacement: Data Entry is Dead by 2026 → Jeff’s evolved prediction on AI’s economic impact and why the “lump of labor fallacy” applies to automation fears

Key Takeaways:

• AI-native means redesigning your data architecture from scratch, not adding a chatbot interface to legacy systems
• Run your company on the shortest planning horizon you can see – for Digits, that’s 4-5 week “horizons”
• Hire senior people who are “chill” with strong opinions, loosely held – and actively filter out solo operators
• The most powerful AI products won’t ask users what to do – they’ll understand the goal and just execute
• Accounting’s month-end close will be automated by end of 2025, marking one of AI’s first complete workflow eliminations

About Jeff Seibert:

Jeff is the founder and CEO of Digits, the AI-native accounting platform. Previously, he served as Twitter’s Head of Consumer Product (launching the algorithmic timeline), co-founded Crashlytics (acquired by Twitter, now runs on 6 billion smartphones), and was featured in Netflix’s Emmy-winning documentary “The Social Dilemma.” He’s backed 100+ startups as an angel investor and has been building software since releasing his first app at age 12.

Related Links:

• Digits

“We couldn’t start inkjet again if we had it in our hands because we’re not meeting the rules.” That stark admission from former HP Fellow Will Allen reveals why even the most innovative companies struggle to recreate their own breakthroughs—and what it takes to actually scale disruptive technology.

In this episode, Will Allen, holder of 102 US patents and the first HP Fellow promoted within HP’s Global Print Business, takes us inside three decades of Silicon Valley innovation from logic analyzers to consumer inkjet printing to his current role as CTO at Kaspix, where he’s pioneering ultra-low-power AI inference using analog circuits. We explore why research should be treated as investment portfolio management (not an expense to cut), how “showing beats telling” when getting buy-in for radical ideas, and why getting AI to the “true edge” – directly at sensors and actuators – will fundamentally change computing economics.

What You’ll Discover:

[00:00] Why Research and Development Are Two Different Things

→ The fatal mistake of treating R&D as a single expense line when research is actually an investment with portfolio-level returns

[06:03] Has Silicon Valley Run Out of Ideas?

→ Why scaling success creates the very constraints that prevent future innovation, and whether we’re less innovative than decades past

[10:12] The Scaling Trap That Kills Success

→ Real HP story: how field-fixing problems scaled so badly that engineers couldn’t design problems out, and what this means for any growing business

[16:23] Getting Past the “$100 Million Question”

→ How to navigate corporate demand for predictable returns when developing something the market has never seen before

[18:03] “A Functioning Proto Is Worth a Thousand Pictures”

→ The clownfish story: how a weekend demo got low-drop-volume printing approved after months of rejection, and the art of communicating on stakeholders’ terms

[21:16] Signal Spotting and Fundamental vs Killer Apps

→ Will’s framework for distinguishing noise from transformational trends—and why asking “what’s the killer app?” might be the wrong question

[24:47] Kaspix and the True Edge

→ Why analog circuits for AI inference could be as transformative as the mouse, enabling intelligence directly at transducers without memory-compute bottlenecks

[29:56] Where AI Is Actually Heading

→ Beyond the hype: specialized AIs, “AI middle management,” and why rapid societal change from deterministic technology creates uncomfortable transitions

[36:04] The Advice Will Would Give His Younger Self

→ Why leaders who invested years in education suddenly think quarterly, and how to reclaim the long-term thinking that got you there

About Will Allen:

Will Allen is CTO at Kaspix, pioneering ultra-low-power AI inference through analog circuit design. Previously, he spent 30 years at HP, becoming the first HP Fellow promoted within HP’s Global Print Business. He designed the color imaging pipeline used in HP’s first 4 million color consumer inkjet printers, led IP production in HP Labs’ AI and Emerging Compute Lab, and holds 102 issued US patents across printing, displays, robotics, and digital imaging.

Related Links:

• Will’s LinkedIn Profile

• Will’s Professional Homepage
• Will’s YouTube Channel
• Kaspix
• Kaspix Founder Pablo Zegers interviewed on The Innovators Podcast by John Biggs

What if the leadership frameworks we’ve relied on for decades are fundamentally broken for today’s world? In this thought-provoking conversation, Pascal sits down with Jeffrey Rogers—his collaborator of nearly a decade—to explore how leaders can navigate sustained uncertainty and systematic disruption.

Jeffrey, an expert in organizational learning and futures thinking, challenges the “Good to Great” era of one-size-fits-all leadership models. Instead, he advocates for meta-learning: the ability to learn how to learn, adapt frameworks contextually, and build organizations that can transform repeatedly. They dive deep into the tension between efficiency and experimentation, why the “middle horizon” (5-10 years) is so hard to envision, and how generative AI fits into organizational learning—spoiler: it’s not the efficiency tool you think it is.

Key Topics Covered:

• Why best practices are dead and what replaces them in high-uncertainty environments
• The efficiency vs. learning paradox: how to balance execution with experimentation
• Generative AI’s real value: rapid prototyping, not scaling (and why that matters)
• The futures cone and how to think about multiple possible futures
• Practical advice for middle managers when leadership won’t listen
• Building learning systems that connect across your organization

In this episode, we are joined by Gero Hesse, a distinguished “Top HR Influencer” and CEO of EMBRACE, a Bertelsmann Investments company at the forefront of HR technology. Drawing from his deep expertise, Gero offers a profound perspective on how the HR industry must evolve in an era defined by constant change. The conversation delves into the pressing dichotomy of the talent shortage driven by demographic shifts versus the narrative that AI will automate countless jobs. Gero argues that while technology will inevitably replace administrative roles, it will simultaneously create new ones, shifting the core challenge to workforce transformation and reskilling. He envisions a future where HR transitions from an administrative function to a strategic one, responsible for shaping the cultural and ethical rules for a new, blended workforce of humans and machines.

Gero also shares his personal leadership philosophy, which is anchored in radical authenticity and a commitment to building long-term, trust-based relationships. He believes in being the same person at work and in his private life, a principle visibly reflected in the edgy, unconventional branding of his company and its festival-style conferences. Ultimately, Gero provides clear guidance for leaders and HR professionals: as automation handles routine tasks, the enduring value of HR will lie in its ability to manage the human side of the business. He champions a future where the focus shifts to shaping culture, fostering employee identification, and guiding technology integration in a way that amplifies human potential rather than simply replacing it.

We’re joined by John Fallon, former CEO of Pearson PLC, who led its transformation from a 175-year-old publisher to a global digital learning company. Now an author and academic, John shares insights from his new book, “Resurgent,” on how established companies can thrive amidst disruption by leaning into their core strengths while learning to be agile. He argues that a strong, unifying sense of purpose is the most critical factor in navigating the immense challenges of change.

John asserts that the “transformation” aspect of digital change is far harder than the “digital” part itself. He describes the core leadership challenge as bridging the gap between exponential technological progress and the linear way humans adapt. Success requires making change tangible and near-term, and he reframes middle managers not as a “permafrost” layer blocking change, but as the organization’s essential “shock absorbers” who translate strategy and manage the associated anxiety.

Looking ahead, John provides practical advice, from using AI as a tool to create a powerful “first draft” that human creativity can then elevate, to having the patience required for a journey that often takes over a decade. He explains that leaders must protect small, innovative initiatives with non-financial KPIs and foster a culture of continuous change, recognizing that in the modern era, you are either busy being born or busy dying.

→ John’s new book "Resurgent: How Established Organizations Can Fight Back and Thrive in an Age of Digital Transformation"

In this episode, we welcome Stefanie Klein, who leads the international initiative Women4Metals at Aurubis AG. With years of experience in the male-dominated metals industry, Stefanie is dedicated to making women in heavy industry more visible and empowered. Her work demonstrates that diversity is a business imperative, essential for driving cultural transformation across an entire sector.

Stefanie explains that the push for diversity at her company is not just a social good but a strategic necessity. It addresses the critical “war for talent” by widening the talent pool and brings diverse perspectives to the table, leading to more sustainable and robust business decisions. The core philosophy of her initiative is to “fix the system, not the women,” focusing on changing the corporate framework to be more inclusive rather than trying to change the women within it. This involves making female role models more visible to attract others and fostering genuine male allyship.

For individuals navigating their careers, especially in traditional industries, Stefanie offers clear, actionable advice. She stresses the importance of building a diverse professional network and seeking out sponsorship, noting that women are often “over-mentored but under-sponsored.” Her final guidance for young people is to remain curious, be proactive in connecting with companies, and stay open to all opportunities, particularly in STEM fields where there is immense potential for growth and impact.

In this episode, Pascal sits down with Brian Brault, a leadership development expert who runs programs at MIT with the Entrepreneurs Organization, to explore how leadership has fundamentally evolved in our rapidly changing world. Brian shares insights on the shift from traditional “smartest person in the room” leadership to emotionally intelligent, authentic leadership that prioritizes building teams and genuinely caring for people. The conversation delves into the fascinating duality modern leaders face: being vulnerable and empathetic with human teams while maintaining strict control and boundaries when managing AI agents and systems. Brian emphasizes the critical difference between “being vulnerable” and “leading with vulnerability,” explaining how authentic leaders can acknowledge uncertainty while still providing direction and commitment. The discussion covers the future of organizational structures, the continuing importance of middle management despite Silicon Valley trends, and practical advice for leaders navigating the “messy middle” of technological disruption. Brian concludes with actionable guidance for emerging and established leaders looking to adapt their leadership style, including the power of mentorship and leveraging personal strengths rather than focusing on weaknesses.

Timestamps:

00:00 Introduction and Leadership Evolution

01:10 The Shift from IQ to EQ in Leadership

04:00 Trust, Authenticity, and Stakeholder Balance

05:50 The AI Leadership Paradox: Humans vs Machines

09:17 Data Accuracy and Decision-Making in the AI Era

11:35 Outdated vs Essential Leadership Skills

12:22 Brian's Story: Learning to Lead Without All the Answers

16:17 Creating Organizations of Leaders, Not Followers

17:44 Leading Into the Unknown and Career Transitions

21:48 Building Empowered Teams and Strategic Clarity

22:15 The Future of Organizational Structure and Middle Management

26:24 Defining Vulnerable vs Leading with Vulnerability

28:57 Practical Advice for Adapting Leadership Style

33:40 Where to Find Brian and Legacy of Significance

↗ Brian's company: Legacy of Significance

↗ Connect with Brian on LinkedIn

In this episode, Pascal is joined by Scott Wingo, a pioneer in the e-commerce space, to discuss the concept of 'liminal space' and the rapid changes brought by AI and geopolitics. Scott shares his journey from growing up with a mainframe in his home to navigating the fast-paced shifts from desktop to mobile and now AI. The conversation delves into the complexities organizations face in adapting to technological advancements, highlighting Martex’s Law and the need for a non-binary approach to change. Scott explains his 70-20-10 framework developed at ChannelAdvisor to balance core business activities with innovation. The discussion also covers the future of AI-native organizations, the rise of agents in e-commerce, and how leaders can manage these agents effectively. Scott emphasizes the importance of staying updated through podcasts and other high-signal sources while also sharing insights on potential disruptions in traditional search models by AI-driven platforms.

00:00 Introduction and Liminal Space

00:59 Technological Evolution and AI

03:15 Organizational Change and Martex Law

04:15 Framework for Managing Change

07:34 AI Native Organizations

11:31 Staying Updated in a Rapidly Changing World

17:36 Diving into Agent AI in E-commerce

18:56 The Potential of Agent AI in Everyday Life

20:52 Managing a Company with AI Agents

22:06 Building an AI-Driven Organizational Structure

28:42 The Future of AI in Business Efficiency

31:26 The Shift from Google Search to AI-Powered Tools

33:58 Conclusion and Final Thoughts

↗ Scot’s new venture: ReFiBuy.ai