The Digital Diaries Hosted by Peter Woods

Overvoew

What does it take to build a category when customers do not yet know they need what you are selling?

In this episode of The Digital Diaries, Peter Woods speaks with Amit Sharan, SVP of Marketing at Tatari, about building brands, marketing teams and entirely new markets.

Amit shares lessons from helping build LiveRail into a leading video advertising platform before its acquisition by Facebook. He also reflects on his time at Meta, where he worked across advertising and products including Facebook Watch, Facebook Live and video monetisation.

The conversation explores why Amit prefers building over maintaining. He explains why clarity of positioning was so important at LiveRail and why marketing needs to do more than generate demand. It also needs to build the value and reputation of the company.

Amit explains what category creation really means. Sometimes customers are not actively searching for your solution. You first need to show them why the category matters before explaining why your company does it better.

Peter and Amit also explore the evolution of TV advertising. TV is becoming more measurable, targeted and accessible. Connected TV, retargeting and new advertising formats are bringing it closer to the performance marketing world.

They also discuss the growing role of AI in marketing. This includes how brands appear in LLMs, AI-powered media planning and AI-generated advertising. Amit shares why AI can reduce production costs, but also raises questions around consumer trust, synthetic talent and regulation.

Finally, Amit explains why he believes TV remains one of the most powerful brand-building channels available. Social media might amplify cultural moments, but many of those moments still begin on television.

• Why Amit prefers building businesses from zero to one

• Lessons from scaling LiveRail and working at Meta

• Why clear positioning can create a competitive advantage

• The difference between demand generation and category creation

• Why digital-first brands eventually need new channels to grow

• How connected TV is changing television advertising

• The opportunity for TV retargeting in B2B marketing

• How AI is changing search, media planning and advertising creative

• Consumer trust and regulation around AI-generated talent

• Why TV and social media can be stronger together

• Why leaders should give people problems to solve, not just tasks to complete

Great marketing is not only about capturing existing demand. Sometimes you need to create the market first.

That means educating customers, establishing the category and building trust before someone is ready to buy.

For Amit, the same thinking applies to leadership. Give talented people a meaningful problem to solve and the space to work out how to solve it.

In this episode of The Digital Diaries, host Peter Woods speaks with Dr Rebecca Hinds, author of Your Best Meeting Ever, founder of the Work AI Institute at Glean, and former head of the Work Innovation Lab at Asana. They discuss why workplace meetings have become so dysfunctional and how applying product design principles can transform collaboration. Dr Hinds reveals actionable frameworks like the 4D CEO test, methods for managing calendar overload, and how artificial intelligence is reshaping modern work practices.

• Treat Meetings like Products: Organisations should view meetings as critical internal products, using intentional design principles to optimise alignment and decision-making.

• Meeting Doomsday: Conducting a calendar cleanse at the team level can reclaim substantial time, including up to 11 hours per person each month.

• Combating Parkinson's Law: Work expands to fill allotted time; setting shorter meeting durations (such as 50 minutes) or wrapping up once goals are achieved prevents wasted effort.

• Verb-Driven Agendas: Structuring agendas around actionable verbs ensures attendees understand the exact objective of each item.

• Measuring True Costs: Beyond direct salary calculations, unoptimised schedules inflict heavy cognitive costs and fatigue across organisations

• Navigating AI and "Bot Sitting": AI can streamline operations, but poor setup forces workers to spend up to 6.5 hours weekly supervising automated too

Key Takeaways

• Treat Meetings like Products: Organisations should view meetings as critical internal products, using intentional design principles to optimise alignment and decision-making.

• Meeting Doomsday: Conducting a calendar cleanse at the team level can reclaim substantial time, including up to 11 hours per person each month.

• Combating Parkinson's Law: Work expands to fill allotted time; setting shorter meeting durations (such as 50 minutes) or wrapping up once goals are achieved prevents wasted effort.

• Verb-Driven Agendas: Structuring agendas around actionable verbs ensures attendees understand the exact objective of each item.

• Measuring True Costs: Beyond direct salary calculations, unoptimised schedules inflict heavy cognitive costs and fatigue across organisations.

• Navigating AI and "Bot Sitting": AI can streamline operations, but poor setup forces workers to spend up to 6.5 hours weekly supervising automated tools.

This week Peter is joined by Bryan Adams — CEO and founder of Happy Dance, best-selling author, TEDx speaker (1.4M+ views), and one of the leading voices in employer branding and candidate experience. Over two decades, Bryan has helped nearly 200 global organisations — including Apple, Canva, Salesforce and Johnson & Johnson — rethink how they attract talent.

In this conversation, Bryan and Peter dig into why the best employer brands are built on honesty, not hype — and why "selling the truth" beats selling the perfect story every time.

• The origin story — how a workshop moment that "gave Bryan goosebumps" set him on the path from marketing to employer branding, before the term even existed
• Sell the truth, not the perfect story — why leading with the real challenges of a role (not just the perks) attracts the right candidates and repels the wrong ones
• The imposter syndrome fix — how radical clarity about what a job actually demands removes the guesswork for new hires
• Why career sites still fall short — page speed, legacy tech, and the risk-aversion of large organisations
• AI and conversational candidate experience — how career sites are moving from static job boards to systems that "listen before they speak," cutting a 1,200-job firehose down to the 3 roles that actually fit
• Good friction vs. bad friction — why re-typing your CV into an ATS is needless friction, and what good candidate experience removes
• The three layers of story every organisation needs — reputation (what you're known for), expectation (the deal you're offering), and experience (the stories only your employees can tell)
• Leadership advocacy — why employer brand only works when it's championed from the C-suite down, not run as an HR side project
• Bryan's own story — nearly going out of business from a fear of public speaking, and the standup comedy course that changed everything
• Five years out — Bryan's prediction that transparency, not perfection, will become the ultimate measure of emplyer brand

About Bryan Adams

Bryan is CEO and founder of Happy Dance, and author of Give and Get Employer Branding. His new book, Sell the Truth — a storytelling playbook for leaders who want to build cultures that win — is out 17 September in all good bookstores and on Amazon.

• Learn more about Bryan's work at Happy Dance
• Pre-order Sell the Truth, out 17 September

Overivew

What does it take to reinvent a product that hasn't meaningfully changed in decades?

In this episode of The Digital Diaries, Peter Woods is joined by entrepreneur and product innovator Oscar Hedaya, founder of Space and creator of the Space Safe, a connected smart safe that combines modern technology with traditional physical security.

Oscar shares his journey from growing up with limited means to building multiple consumer product businesses, revealing how necessity sparked an entrepreneurial mindset that continues to shape his approach to innovation. Together, they explore what it really takes to bring hardware products to market, why customer feedback is the foundation of great product development, and how solving genuine problems is far more important than chasing the next big idea.

The conversation also dives into the unique challenges of hardware versus software, the future of connected security, and the realities of entrepreneurship that rarely make it into the headlines.

• How adversity can become an entrepreneurial advantage

• Why successful founders solve real problems—not imagined ones

• The hidden complexity of building hardware products

• What differentiates physical product innovation from software development

• Why customer feedback should shape your roadmap

• How connected technology is changing the future of home and hotel security

• The financial realities every founder should understand before launching a business

• Why AI is becoming an invaluable tool for aspiring entrepreneurs

• Oscar's entrepreneurial journey and early businesses

• Building companies with limited resources

• Spotting opportunities through everyday frustrations

• Designing and launching the Space Safe

• Hardware development challenges and manufacturing lessons

• Cybersecurity versus physical security

• Smart home technology and connected devices

• Customer-led product innovation

• Startup funding, runway and financial planning

• Using AI to validate business ideas

• What success looks like after building multiple companies

Innovation starts with observation. Many of the best products don't invent something entirely new—they improve products people already use every day.

Hardware is unforgiving. Unlike software, physical products can't simply be patched after launch. Small design decisions can have expensive long-term consequences.

Build for genuine customer pain points. The strongest businesses solve problems customers are already experiencing and are willing to pay to eliminate.

Think lean from day one. Managing cash flow, understanding runway and validating demand are often more important than perfecting the product.

Listen to your customers. Some of Space's most valuable product features, including its innovative Panic PIN functionality, came directly from customer suggestions.

"The entrepreneur isn't the person who spots the problem, it's the person who builds the solution."

"Hardware is a nightmare. Software can be updated. Hardware has to be built right."

"Never ask your family and friends if your idea is good, they'll tell you what you want to hear."

"The day you open your business is the day you're open to selling your business."

"Innovation doesn't have to be complicated. Sometimes it's simply upgrading something people already use."

Oscar Hedaya is a serial entrepreneur and product developer with more than 15 years of experience bringing innovative consumer products to market. Having worked across manufacturing, retail and global distribution, he has launched products into major retailers including Walmart, Target, Costco and Best Buy.

Today, he's the founder of Space, creator of the Space Safe—a next-generation smart safe featuring touchscreen controls, built-in cameras, mobile notifications and advanced security features designed for both homes and hospitality environments.

• Space Smart Safe

• Amazon Web Services (AWS)

• Tesla's touchscreen-first design philosophy

• AI tools for market research and business planning

🌐 Space: https://thespacesafe.com

Overview

In this episode of The Digital Diaries, Peter Woods sits down with data scientist, consultant and author Sebastian Wernicke to explore why the biggest obstacle to digital transformation isn't technology—it's organisational courage.

Drawing on two decades of experience leading data science teams, advising Fortune 500 companies and working on national-scale innovation projects, Sebastian challenges the idea that becoming "data-driven" is enough. Instead, he argues that organisations should aspire to become data inspired—using data not just to optimise existing processes, but to unlock entirely new ways of thinking.

From luxury car manufacturers predicting bespoke customer demand before an order is placed, to the hidden politics behind boardroom decisions, this conversation dives into why successful transformation is fundamentally about people, trust and decision-making—not algorithms.

If you're leading digital transformation, building AI capabilities, or trying to create a culture where better decisions happen, this episode offers practical insights that go far beyond dashboards and analytics.

• Why being data-driven isn't the same as being data inspired

• The surprising luxury car case study that generated millions through predictive manufacturing

• Why stakeholder alignment matters more than building the perfect algorithm

• The biggest mistake data professionals make when presenting to executives

• Why decisions are rarely made in the boardroom

• How organisational politics shape successful transformation

• Why culture cannot be "fixed" in a 12-week engagement

• The hidden role of psychological safety in better decision-making

• How companies like Amazon and Netflix intentionally design decision-making processes

• Why many failed technology projects are actually failures of culture

• The inspiration behind Sebastian's new book, Data Inspired

Technology is rarely the hardest part. The real challenge is aligning people across functions and building trust before implementation begins.

The best data projects create new possibilities. Rather than simply optimising existing processes, truly data-inspired organisations use data to rethink how business is done.

Boardroom meetings don't change minds. Successful decisions are usually made through conversations and stakeholder alignment long before executives gather around the table.

Culture cannot be mandated. Sustainable transformation requires leadership commitment, psychological safety and deliberate behavioural change over time.

Decision-making deserves intentional design. High-performing organisations don't leave important decisions to chance—they build repeatable processes that encourage challenge, curiosity and evidence-based thinking.

"The thing holding organisations back isn't their tooling—it's their nerve."

"The hard part wasn't building the algorithm. It was getting everybody into the same boat."

"The decision is never made in the decision meeting."

"Culture is not a project."

"Technology often becomes the lightning rod for cultural problems."

This episode is for:

• Business and technology leaders

• Data and AI professionals

• Digital transformation teams

• Strategy and innovation leaders

• Consultants and change managers

• Anyone interested in how organisations make better decisions

Sebastian Wernicke is a data scientist, consultant and author of Data Inspired. With over twenty years of experience helping organisations use data more effectively, he has worked across Fortune 500 companies, public sector initiatives and large-scale transformation programmes. His work focuses on helping organisations move beyond optimisation to create genuinely data-inspired cultures and decision-making.

• Data Inspired by Sebastian Wernicke

• Amy Edmondson's work on Psychological Safety

• Amazon's six-page memo decision-making process

• Netflix's approach to empowered decision-making

• Adam Grant's endorsement of Data Inspired

Don't forget to subscribe, leave a review and share it with someone.

What does it take to transition from commanding 350 people in military aviation to flying commercial aircraft while simultaneously building technology companies?

In this episode of The Digital Diaries, Peter Woods sits down with Rob Wright, a former U.S. Army Special Operations Aviation commander, commercial airline pilot, and entrepreneur. Together they explore leadership under pressure, making difficult decisions, the realities of entrepreneurship, and how AI is changing the way businesses operate.

Rob shares lessons from military leadership, explains why execution beats ideas every time, and discusses how his company, Waffl, helps organisations build AI-powered software that solves real business problems—not just shiny technology.

Whether you're leading teams, building a startup, or trying to understand where AI creates genuine business value, this conversation is packed with practical insights.

• Why military leadership is built on trusting the people around you

• The biggest adjustment from Army command to commercial aviation

• Why time—not money—is your most valuable resource

• How Rob balances multiple businesses alongside a flying career

• The story behind Waffl and building custom AI solutions for businesses

• Why AI alone isn't a competitive advantage

• The difference between automation and creating real business value

• How businesses can identify hidden inefficiencies in their operations

• Why execution consistently beats great ideas

• The importance of validating customer demand before building a product

• Great leaders don't make decisions in isolation—they rely on experienced teams and proven processes.

• AI should create new value or remove unnecessary costs, not simply make existing tasks slightly faster.

• Every business has operational bottlenecks that become opportunities when they're properly measured.

• Owning your own software and intellectual property can become a long-term competitive advantage.

• Entrepreneurs often overestimate ideas and underestimate execution.

• Positive feedback doesn't equal paying customers—market validation is everything.

"The best ideas don't win. The best execution does."

"Time is the most valuable resource."

"You're not really using the power of AI unless you're creating new value for your company or eliminating unnecessary spend."

"There's a big difference between someone saying your idea sounds great and someone writing you a cheque."

• Military leadership

• Decision making under pressure

• Commercial aviation

• Entrepreneurship

• Startup growth

• AI implementation

• Digital transformation

• Business automation

• SaaS development

• Product-market fit

• Operational efficiency

• Leadership lessons

Rob Wright is a former U.S. Army aviation commander, commercial airline pilot, and entrepreneur. Alongside his aviation career, he helps organisations build custom software and AI solutions through Waffl, focusing on practical technology that delivers measurable business outcomes.

• LinkedIn: Robert Wright

• Website: GoWaffl.com

If you enjoyed this episode, subscribe to The Digital Diaries, leave a review, and share the episode with someone interested in leadership, entrepreneurship, or the future of AI in business.

New episodes released every week.

Episode SummaryWhat You'll LearnKey TakeawaysMemorable QuotesTopics CoveredAbout the GuestConnect with Rob WrightConnect with The Digital Diaries

🧭 Episode Overview

In this episode of The Digital Diaries, Peter Woods sits down with Sean Collins. A rare operator who has lived on both sides of the technology buying journey. From 20+ years in IT leadership to commercial director and UK General Manager at Tech Enable, Sean brings a grounded, real-world perspective on how enterprise decisions actually get made.

Together, they unpack the evolution from technical delivery to commercial strategy, the psychology of trust in B2B sales, and why most AI initiatives fail long before the technology becomes the problem.

💡 Key Themes

1. The power of “both sides of the table” experience
Sean shares how moving from IT leadership into consultancy and commercial leadership gave him a rare ability to understand both operational pain and commercial pressure — especially when signing off major systems.

2. Trust is the real currency in enterprise salesTechnology matters, but decisions are ultimately made on trust. Sean explains why credibility, honesty, and sometimes even walking away from deals is what builds long-term relationships.

3. Why most AI projects fail (it’s not AI)A recurring theme: AI doesn’t fail — data does. Sean breaks down why poor CRM hygiene, broken processes, and inconsistent adoption undermine even the most advanced AI tools.

4. CRM, ERP, and the myth of “one system to rule them all”
From Salesforce to ERP systems like Microsoft Business Central, Sean explains why successful transformation depends on integration, not replacement.

5. The real starting point for AI adoptionInstead of chasing AI use cases, organisations should start by identifying operational friction:

• Where are teams overloaded?
• Where are processes breaking?
• What would genuinely save time?

Episode Overview

What happens to your brand's reputation when AI agents, not your marketing team, are the ones answering questions about your company?

This week Peter is joined by Gal Borenstein, founder and CEO of The Borenstein Group and author of Don't Believe the Hype: When Trust Is on the Line. Gal has spent close to 30 years building and protecting brands for clients including Airbus North America and Forrester Research, and his book argues that generative AI has fundamentally broken the old model of brand control.

Gal explains why narrative ownership has shifted away from companies and towards AI search engines and anonymous online voices, why deploying AI agents without institutional knowledge is like handing your brand to a junior employee with no real-world experience, and why the businesses most at risk are the ones rushing to "keep up" without first getting their internal house in order.

The conversation covers his GUARDIAN Digital Trust Framework, the Boeing case study on what happens when problems don't travel up the chain of command, why "vanity metrics" won't save a damaged reputation, and a candid challenge to Gal himself: is there a conflict of interest in a branding agency owner writing a book that says companies need outside help?

What you'll learn:

Why AI search engines and generative answers have removed companies' control over their own brand narrative

The "junior employee" problem: why agentic AI without institutional knowledge creates real reputational risk

The three ways companies typically respond to AI disruption, and why the seemingly safest option is often the most dangerous

How the GUARDIAN Digital Trust Framework helps leaders build resilience before a crisis hits

What the Boeing case reveals about reporting culture and reputational collapse

Why "private company" is no longer a real strategy, and what a proper digital footprint actually involves

How to tell genuine trust signals apart from vanity metrics like follower counts

Gal's own answer to the "Start With Why" challenge, and what he changed his mind about in the last 12 months

About the guest:

Gal Borenstein is the founder and CEO of The Borenstein Group, a branding and PR agency, and the author of Don't Believe the Hype: When Trust Is on the Line, Activate!, and What Really Counts for CEOs. He has spent close to three decades advising C-suite executives on brand resilience.

Connect with Gal on LinkedIn or find his books on Amazon. Mention this episode when you message him for a complimentary copy of his latest ebook, Beating Goliath with AI.

The Digital Diaries is where we explore what it actually takes to lead, build, and transform in a world that won't slow down.

Follow Peter Woods and The Digital Diaries for new episodes every week.

Episode OverviewAfter 25 years inside enterprise transformation projects, Barbara Wittmann, Founder of the Digital Wisdom Collective, reached an uncomfortable conclusion: most technology projects don't fail because of the technology. They fail because organisations never built the human infrastructure to support it.

In this episode, Barbara and Pete unpack why she treats people as infrastructure in exactly the same way IT treats servers, including test environments, upgrade cycles and ongoingmaintenance. They get into alignment debt, the hidden cost that builds up when leadership assumes consensus that was never actually verified, and why 70 per cent of project time is spent solving the wrong problem entirely. Barbara also shares her four-pillar framework for collective problem-solving,why she believes organisations need “chiefs” rather than managers, and why AI's biggest gift might be forcing us to finally get honest about our own hallucinations.

This conversation is forleaders under pressure to show AI results fast, anyone running (or living through) a transformation project, and anyone curious about what “wisdom” actually means in a digital-first world.

Almost every executive will tell you they are committed to AI. Very few organisations are actually being transformed by it. So what is really happening in the gap between what leaders say about AI and what they do?

This week, Pete sits down with Dr Victoria Mensch, Founder and CEO of the Silicon Valley Executive Academy. With a PhD in Psychology, an MBA from UC Berkeley and over 25 years in Silicon Valley technology including 14 years at SAP, Victoria spends her working life helping senior leaders lead AI transformation. As a psychologist, she has a sharp diagnosis of what is actually holding them back, and it is not strategy. It is identity.

This is a conversation about the human side of AI adoption: the identity crisis it triggers in senior leaders, the quiet sabotage that follows, and what genuine transformation looks like once you stop treating AI as just another efficiency play.

In this episode:

- Why AI adoption stalls long after the strategy is signed off

- The difference between using AI to do existing work faster and using it to transform the work itself

- The identity crisis hitting senior leaders: if AI can do intellectual work better, what is left for me?

- Why fear of replacement quietly shows up as sabotage at every level of an organisation

- The unbundling of job roles, and how to take ownership of your career inside it

- What the Silicon Valley Innovation Playbook offers leaders in more traditional industries

- Why genuine transformation requires the courage to push back on pure efficiency pressure

- How AI amplifies burnout by setting false expectations of human output volume

- A practical, science-backed approach to replenishing energy in a high-pressure environment

- Why we overestimate AI's short-term impact and underestimate how it reshapes work over time

- The mindset that will separate leaders who genuinely transform from those who only perform it

Standout moment: Victoria reframes AI resistance as an identity crisis rather than a strategy debate. The private question every executive is asking, she argues, is "if AI can do it better, what am I?", and it often shows up as sabotage rather than honest pushback.

About Victoria:

Dr Victoria Mensch is Founder and CEO of the Silicon Valley Executive Academy (SVEA), a boutique executive education and innovation consulting firm. She designs immersion programmes that equip global leadership teams to lead AI transformation, drawing on her V.I.T.A.L. method and the Silicon Valley Innovation Playbook. Her work sits at the intersection of psychology, executive performance and technological change.

Connect with Victoria:

- Sign up for SVEA's weekly newsletter at svexecutive.academy

- LinkedIn: linkedin.com/in/victoriamensch

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