Hollis discusses the intricacies of raising capital, emphasizing the importance of multiple interactions with potential investors. He highlights the average of 32 touchpoints required to secure a significant investment and explores how AI can streamline this process without compromising the quality of engagement.

00:00 Beginnings with Technology and Career

06:20 When to use Tech and People

08:08 Implementing Tech into Real Estate (Raise AI)

12:45 Streamlining "32 Touch points" with AI

19:31 Building a Team and AI Adoption

24:06 AI Future-proofing and Relationships

28:36 Why Real Estate AI and Building Culture

33:02 The Future of Raise AI

William Hollis, known as “Hollis,” is the Founder & CEO of Raise AI, where he helps real estate capital raisers and fund managers use AI-powered automation to streamline investor communication, increase deal visibility, and raise capital faster. A self-taught software engineer turned real estate investor, Hollis specializes in bridging cutting-edge AI technology with the real-world challenges of capital raising.

Born and raised in Hollis, Queens, NY, he has built his career at the intersection of AI, automation, and real estate. Before founding Raise AI, Hollis developed AI solutions for global brands like Disney and Nike, then applied those same efficiencies to real estate by launching 24 Capital Group in 2022 and 24 Tech Systems in 2024. Today, through Raise AI, he empowers dealmakers with scalable, intelligent systems that replace manual follow-ups and outdated workflows—helping them move from hustling for capital to raising it effortlessly.

• RaiseAI: https://theraiseai.com/

• Website: https://williamhollis.com/

• LinkedIn: https://www.linkedin.com/in/rei-hollis/

Scott Morris, a veteran HR leader turned startup founder, discusses his transition from a successful corporate career to launching Propulsion AI, an innovative company focused on AI-powered HR solutions. He highlights the significant challenges in traditional HR practices, particularly the lack of clarity in role expectations and the misalignment of employee engagement. Scott introduces Athena, an AI teammate designed to enhance role design and improve hiring processes, ultimately aiming to create a more effective and engaged workforce. The discussion also touches on the future of hiring, performance management, and the importance of understanding the value of operational roles within organizations.

00:00 - Risks, Startups, and HR

07:35 - Solving The Problem with Hiring

14:39 - Athena and Propulsion

21:20 - Importance of Operational Roles

25:04 - Athena as a Teammate

29:41 - Collaborating with Tech

32:08 - Culture in the Hiring Process

34:32 - Are You Ready to Hire?

38:41 - Future of HR Tech

41:44 - Hiring and Managing Advice

With more than 25 years of HR leadership - including two decades at the C-suite level - Scott Morris has navigated talent management across five distinct industries and two continents. He's led HR strategy for nimble tech startups with 250 employees and orchestrated comprehensive workforce solutions for enterprises exceeding 15,000 employees. His experience spans the full spectrum of organizational complexity, guided by a core philosophy: if it feels comfortable, you're behind.

Scott is now Founder & CEO of PropulsionAI, building the first HR team made entirely of AI - digital teammates that coach managers through strategic talent decisions using proven frameworks. These AI coaches clarify how roles connect to business outcomes, transform hiring and performance management, automate labor-intensive documentation, and help organizations simultaneously raise employee engagement and productivity.

• Website: https://getpropulsion.ai/

• LinkedIn: https://www.linkedin.com/in/mscottm/

Mark and Margaret explore how leaders can operate effectively in unpredictable environments, emphasizing curiosity, reflection, and making decisions without perfect information. They discuss the limits of efficiency, the risks of relying too heavily on metrics, and how AI may weaken independent thinking. Margaret shares real examples of leaders who improved their organizations by listening more, empowering their teams, and building trust. They also examine extreme work cultures, the importance of maintaining personal autonomy, and how strong social connections in remote teams support better collaboration and problem-solving.

00:00 - The World of Uncertainty

03:57 - Curiosity in Business

10:15 - Measurements, Data, and KPIs

12:51 - Letting AI think for Us

16:29 - Growing Leadership Skills

26:31 - CEO Coaching Experience

33:29 - 9-9-6 Mentality

38:00 - Business Trends

40:00 - Social Capital with Global Teams

45:40 - Margaret's Essential Question

Dr. Margaret Heffernan began her career producing BBC radio and television programmes, including dramas, documentaries, and the first broadcasts featuring Simon Schama. After moving to the United States, she led multimedia initiatives for Intuit, The Learning Company, and Standard & Poor’s, later serving as CEO of InfoMation Corporation, ZineZone, and iCast. Recognized as one of Streaming Media’s “Top 25” and The Hollywood Reporter’s “Top 100 Media Executives,” she is also the author of seven influential books, including Willful Blindness, A Bigger Prize, and the best-selling Uncharted. Her TED talks have been viewed more than fifteen million times, and her next book, Embracing Uncertainty, will be published in 2025.

A Professor of Practice at the University of Bath, Heffernan mentors global CEOs through Merryck & Co., speaks at major international conferences, and chairs the board of DACS. She has advised high-profile public inquiries, was inducted into the Thinkers50 Hall of Fame in 2023, and is a frequent BBC Radio 4 broadcaster. She also writes for the Financial Times and serves as a parish councillor.

• Website: https://mheffernan.com/

• X: https://x.com/M_Heffernan

• Ted: https://www.ted.com/speakers/margaret_heffernan

• Substack: https://heffernanm.substack.com/

David Soileau discusses the potential of AI and automation in optimizing customer service and order processing. He emphasizes the importance of accurate order entry to reduce the need for customer service interactions and highlights the benefits of automating documentation processes. The discussion also touches on the shift towards self-service options, reducing manual data entry, and streamlining operations to enhance efficiency.

00:00 – Gopher’s Origin & Pivot

04:18 – Why Logistics Needs Tech

07:40 – Going Digital in Old Industries

10:16 – AI Features: Pic-to-Ship & GoPilot

12:12 – Tech Challenges & Early Mistakes

16:21 – Team, CTO, and Automation

20:07 – Fixing Legacy Logistics

24:23 – Techstars, Expansion & Future of AI

David is an entrepreneur and founder passionate about building companies that transform industries and create lasting impact. As a Co-founder of Gophr, he's part of a team redefining logistics and procurement. By combining pricing intelligence, technology, and service, they’re delivering a faster, smarter, and more cost-effective way for industrial and construction businesses to move materials and products. Their vision is to save teams time, reduce costs, and reshape the future of logistics. He's also a founder of Embark, a business incubator designed to launch and scale ventures that matter. At Embark, they provide entrepreneurs with the tools, network, and mentorship needed to transform ideas into thriving businesses. Alongside these ventures, David owns Integrity Homes, a residential construction company built on trust, craftsmanship, and long-term relationships. Whether it’s homes, logistics systems, or startups, his passion is taking ideas from the ground up and scaling them into businesses that create real impact. David thrives on solving big problems, building strong teams, and driving sustainable growth. Always open to connecting with leaders, innovators, and partners who share a vision for building what’s next.

• Website: https://gophrapp.com/

• LinkedIn: https://www.linkedin.com/in/davidtheguy

• Youtube: https://youtube.com/@gophrapp

How do you lead when AI is changing everything about how we work?

Mike Todasco, former Senior Director of Innovation at PayPal and Visiting Fellow at the SDSU AI Lab, talks about what it really takes to build an AI-first organization. Mike shares hard-won lessons from running innovation inside Paypal, why most teams get stuck in “pilot hell,” and how leaders can build a culture that embraces experimentation instead of fearing it.

Mark and Mike also explore the human side of tech leadership: creativity, curiosity, adaptability, and how to stay grounded as AI accelerates. From PayPal’s innovation tournaments to the future of work and the rise of solopreneurs augmented by AI, this episode gives CTOs and tech leaders a clear, practical view of what’s coming, and how to prepare.

00:00 Who Is Mike Todasco?

02:42 What AI-First Really Means for Companies

04:32 How Leaders Can Drive AI Adoption

07:56 Inside PayPal’s Innovation Culture

15:31 Getting Executive Buy-In for Innovation

21:06 The Leadership Skills That Matter in the AI Era

32:42 The Future of Work: Humans + AI

39:43 When AI Feels Overwhelming (Mike’s Advice)

Michael Todasco is the former Senior Director of Innovation at PayPal, where he spent over a decade leading initiatives to design, test, and scale disruptive ideas across the company. He is currently a Visiting Fellow at San Diego State University’s Artificial Intelligence Lab, where he explores the intersection of AI, creativity, and the future of work. In addition, he is pursuing his MFA in Creative Writing at Johns Hopkins University, blending his passion for storytelling with his expertise in technology. A frequent speaker and writer on AI, innovation, and creativity, Michael helps audiences rethink how to stay relevant and human in a rapidly changing world.

• "How to Win Friends and Influence People" by Dale Carnegie

• LinkedIn: https://www.linkedin.com/in/todasco/

• Website: https://todasco.lovable.app/

Coby Skonord founded IdeaWake, an innovation crowdsourcing platform. He addresses common misconceptions about innovation in organizations, the role of technology leaders, and the importance of integrating innovation into company culture. Koby also shares insights on overcoming budget constraints, navigating security challenges, and the impact of AI on innovation processes. He emphasizes the need for a sustainable innovation culture that is measured and integrated into the organization's goals.

00:00 – Leaving EY to Build Ideawake

02:35 - Why Innovation Fails Inside Big Organizations

03:47 - Building a Culture That Enables Innovation

05:26 - Turning Ideas into Impact

09::38 - Innovation in Healthcare and Regulated Industries

10:37 - The CTO’s Role in Driving Innovation

13:50 - Escaping the Budget Trap

19:35 - Breaking Through Enterprise Barriers

26:36 - The Future of Innovation and the Role of AI

Coby Skonord helps corporate innovation, improvement, and HR teams more effectively tap into the wisdom of employee ideas.

Over the last decade he's led the team at Ideawake, an innovation management platform used by thousands of companies like KraftHeinz, SiriusXM, and Jason's Deli power their employee ideas program focused on growing revenue, reducing costs, and improving efficiency.

• Website: https://ideawake.com/

• LinkedIn: https://www.linkedin.com/in/coby-skonord/

Bart Spangenberg, co-founder and CTO of New-U, shares his personal health journey and how it led him to create a health tech company focused on employee well-being. He discusses the challenges of transitioning from a health background to tech, the importance of data privacy in health apps, and how behavioral science informs the design of their application. Bart also highlights the significance of building a strong remote team, hiring for culture, and the future goals of New You, including market expansion and integrating their services into organizations.

00:00 From Personal Struggles to a Mission in Health

02:49 Learning to Code & Building New-U

06:39 Lessons from Working with an Agency

08:49 What New-U does

10:59 Privacy by Design and Trust in Health Data

14:19 Digitizing the Dutch PMO: Compliance Meets Health

15:50 Leading a Remote International Development Team

20:04 Hiring for Mindset, Growth, and Culture Fit

26:29 Applying Behavioral Science to Product Design

32:36 The One Thing: Focus and Decision-Making in Leadership

Health, you wish the best for your friends and family. However, sometimes we forget to take care of ourselves. That was me. Ignited by being not so healthy, I decided to turn things around. Health has fascinated me for many years now. This wonderful obsession has greatly improved my life, and I hope it will make yours phenomenal as well!

My mission is to help as many people as possible to take control of their health.

I found that this is achieved best through digital solutions. So NewU was born. Our enterprise builds digital health solutions for exercise, nutrition, sleep, connectedness, smoking, mental wellness and much more. Every day I am grateful that I can work with passionate professionals that share this mission.

You can wake me up to talk about technology, behaviour, UI/UX, high performance, design, habits or health.

• Designing for Behavior Change by Stephen Wendel

• The Phoenix Project by Gene Kim, Kevin Behr & George Spafford

• Clean Code by Robert C. Martin

• Clean Architecture by Robert C. Martin

• The Pragmatic Programmer by Andrew Hunt & David Thomas

• The One Thing by Gary Keller & Jay Papasan

• Website: https://www.newu-app.io

• LinkedIn: https://www.linkedin.com/in/bartspangenberg/

Peter Coyle, CTO and co-founder of AudioStack, shares insights on building an AI-driven audio production company before the AI hype. He discusses the importance of understanding customer needs, the impact of AI on workflows, and the significance of team dynamics in a distributed environment. Coyle also emphasizes the value of open source contributions and offers advice for startup founders navigating the competitive landscape of AI technology.

00:00 Building AI Before the Hype

03:41 Surviving the GPT wave

05:57 Defensibility without mega-rounds

07:30 What AudioStack actually does

08:11 One-to-many: turning unscalable into scalable

12:06 Thin wrappers vs thick platforms

14:58 Model churn & provider neutrality

19:34 Ship faster: the metric that matters

24:17 Open Source Communities vs. Business Customers

26:40 Scaling across locations

30:25 Government advice

36:05 CTO and Startup Lessons

Peadar Coyle is CTO and co-founder of AudioStack.

Together with the Head of Engineering, he is dedicated to making AudioStack’s audio production infrastructure flexible, reliable, secure and scalable to meet the diverse ambitions of agencies, brands, publishers and AdTech.

He is an authority on software engineering, data science and AI, and has been invited on multiple occasions as a contributor to steering groups on AI innovation by industry groups and the UK Government.

He has long been an involved member of the Open Source community, and his core role in developing PyMC3, a Bayesian Computing Library, has supported the development of numerous scaleups around the world.

With an AI-native, technical founder’s perspective, he is passionately involved in conversations about the culture of engineering and has published a series of interviews of the teams behind data science innovations at some of the world’s best-known tech disruptors (Amazon, Spotify, Etsy).

• Audiostack Website: http://www.audiostack.ai/
• Peader's LinkedIn: https://www.linkedin.com/in/peadarcoyle/
• and on Youtube: https://www.youtube.com/c/Aflorithmic

In this conversation, Tony Kyriakidis, founder of Nevron, shares his journey from Cyprus to the Netherlands, detailing his experiences in software development and the establishment of Mission Control, a platform for incident management. He discusses the importance of learning the local language for business success, navigating government contracts, and transitioning from an agency model to a product-focused company. The conversation also explores the role of AI in incident management, proactive project management strategies, and the freedom and challenges of entrepreneurship.

00:00 Introduction

02:19 Learning Dutch & Fitting in

10:16 Landing the First Government Client

15:27 Transitioning from Agency to Product

19:45 What Mission Control actually does

24:36 Leadership & Operations at Scale

33:36 AI in Incident Management

38:51 Risk Planning & Entrepreneurial Mindset

42:16 Freedom and Entrepreneurship

Tony is the founder of Nevron B.V., a software company specialized in mission-critical systems for governments, law enforcement, organisations, and major events. Since starting his entrepreneurial journey with Smashing Parties in 2014 and Venuepark in 2016, he has built a track record of delivering high-impact solutions. Under his leadership, Nevron’s software has been used during the Formula 1 Dutch Grand Prix, by the Dutch National Police, Rijkswaterstaat, and at leading festivals in the Netherlands. With a clear mission to become the world’s leading incident and operations management software company within the next 30 years, Tony continues to drive Nevron forward.

• Website: https://nevron.io
• LinkedIn: https://www.linkedin.com/in/tony-kyriakidis
• Instagram: https://instagram.com/iam.tony

Nola Simon is a strategic futurist, and we discuss the evolving landscape of remote work, the importance of trust and connection in the workplace, and the integration of AI with her. Nola shares her insights on building engaged remote teams, the significance of asynchronous work, and the necessity of measuring trust within organizations. She emphasizes the need for strategic foresight in navigating rapid changes in technology and society, and discusses the role of narrative intelligence in leadership. The conversation concludes with practical advice for CTOs on fostering a culture of trust and engagement in distributed teams.

00:00 Intro to Remote Work & Flexibility

05:34 Creating Connection in Remote Teams

10:55 Async workflows, documentation, and AI

13:31 Earning trust for knowledge sharing

15:16 Measuring trust via outcomes & psychological safety

29:04 Strategic foresight: scenarios and adaptability in AI turbulence

44:35 Playbook for first-time distributed CTOs

Nola Simon is a strategic futurist and a steady voice for leaders navigating the messy, human moments at work. Her keynotes are part mirror, part map—reflective, insightful, and grounded in the lived experience of leading when the future isn’t clear.

What sets Nola apart? She blends sharp systems thinking with a warm sense of humour and a love of pop culture. Whether it’s a tongue-in-cheek reference to a classic sitcom, a playful callback to a viral meme, or a story about the unexpected lessons of a Zoom mishap, Nola uses levity to spark connection and make big ideas stick. Her sessions are as likely to include a laugh-out-loud anecdote as a breakthrough leadership insight.

As host of Hope & Possibilities: A Love Letter to the Future of Work, Nola brings lived experience, quiet power, and a knack for making people smile to every stage. She adapts to the moment—remote, hybrid, or in person—always with clarity, presence, and deep respect for the space she’s in.

Nola invites audiences to question assumptions, explore new perspectives, and leave with a renewed sense of agency, possibility, and optimism about the future of work.

• LinkedIn: https://www.linkedin.com/in/nolasimon

• Youtube: https://youtube.com/@nolasimonsayings

• Website: https://www.nolasimon.com