The Creative Stack

About Neil Schaffer:

Prior to founding Carlton Advisors in 2024, Neil Schaffer was a senior executive or co-founder of innovative, high-growth companies in manufacturing, distribution, financial services, media, and software. Neil has led 10+ M&A transactions, including several successful exits, and 20+ financing transactions, including IPO, secondary public offerings, and private equity and debt offerings. Neil also served as CFO of two technology joint ventures, sponsored by global advertising holding companies and by broadcasting & cable TV giants, that developed and licensed technologies which today are core components powering connected and streaming TV advertising. Carlton Advisors is a strategy-led CEO advisory focused on driving faster growth, improved performance, and bigger exits for B2B companies. Carlton works in concert with business leaders who may not have the time or capacity to focus on growth strategy or the corporate development experience to confidently conduct acquisition or exit transactions.

What you'll learn about in this episode:

• The difference between strategy and planning, and why confusing the two causes companies to stall out.

• Why doing nothing is still a decision, and why inertia is every business's biggest competitor.

• The Strategy Choice Cascade: five questions that fit on a single page and clarify why, where, and how a company competes.

• Why being transparent about strategy internally builds more value than it risks.

• Why cash flow matters more than earnings, and Neil's rule of thumb for raising capital.

• What makes mergers and acquisitions go more smoothly, including the value of approaching a target before it goes to market.

• The story of a startup that engineered its own exit from day one, and how preparation turned a shrinking window into a successful sale.

• Why "wandering around and asking" is one of the most underused habits in business today.

About Stephen Kaupp:

As Valiant's COO, Stephen applies his passion for business and all of the operational aspects that produce positive outcomes for our clients and ourselves. Stephen joined Valiant in the fall of 2016, previously working for Lufthansa Airlines, and founding financial services and operational consulting firms. When not working, Stephen enjoys playing and watching soccer, exploring new places and foods, and riding his motorcycles. Stephen attended Farmingdale State College and New York University.

What you'll learn about in this episode:

• Why "all I need is a laptop" is the most common, and most costly, assumption new business owners make.

• The story of Valiant's own near miss: how an overwhelmed back office nearly derailed the company, and what fixed it.

• How back-office operations have quietly transformed, from paper checks and petty cash boxes to platforms like Bill.com and per-employee expense cards.

• Why a payroll company offering IT support, or an IT company offering payroll, should raise a red flag.

• What should stay in-house even when everything else is outsourced.

• Three things worth paying for: redundant internet service, a rolodex of trusted professionals, and not cutting corners on the small stuff.

About Alyssa Burns:

Alyssa Burns is a communications expert, strategic advisor, and respected leader. As CEO of Alyssa Burns Communications, she brings extensive experience in strategic communications, helping leaders navigate complex issues with clarity and confidence. Alyssa works closely with executive teams to develop communication strategies that build trust, strengthen relationships, and communicate effectively during times of change and uncertainty. She has held senior communications roles at organizations including Edelman Worldwide and Kraft Foods, earning a reputation as a trusted advisor and effective connector. Alyssa's work is grounded in clarity, integrity, and a commitment to helping organizations communicate with purpose and impact.

What you'll learn about in this episode:

• Why the best communications work is invisible, and what's actually happening behind the scenes before a message ever reaches an audience.

• Why staying silent during a crisis does more damage than admitting you don't have all the answers yet.

• The three fundamentals Alyssa relies on with every client: communication as a business strategy, internal communication before external, and credibility earned over time.

• What "red binder syndrome" is, and why most crisis communications plans are written once and never tested again.

• Where cybersecurity fits into a modern crisis plan, and the gap many companies don't realize they have until it's too late.

• How the speed of communication has changed dramatically, even as the fundamentals of trust have stayed the same.

• Why AI can help with research and monitoring, but can't replace judgment, originality, or reading a room.

About Georg Dauterman: Georg believes in the fusion of technology and creativity. With a background in both fields, he started his career in IT departments of publishing and advertising agencies, realizing the critical need for tech aligned with business goals. Joining Valiant in 2004, Georg's expertise and passion for efficiency brought industry recognition. He holds a history degree from Queens College and serves on Datto's Global Partner Advisory Board. Beyond his leadership role, Georg enjoys exploring culinary skills, fitness, and outdoor adventures with his family.

About Megan Quick: Megan is a member of the Valiant Marketing & Sales team, assisting in demonstrating the value of our services and ensuring positive experiences for prospective clients. When not working with technology, she is a theater production manager and performer, producing her own comedy shows, and is an avid writer. Megan has a B.A. in Theater from Sewanee: The University of The South.

What you'll learn about in this episode:

• Why IT is one of the only professional fields with no licensing bar, and how certifications step in to fill that gap.

• The three-legged stool of certification: how it builds trust with clients, opens doors for staff, and signals seriousness to vendors and partners.

• Why Valiant went through a stretch in the 2010s where certification wasn't tied to advancement, and what changed about four years ago.

• The story behind "split-half search," a troubleshooting method from a 1999 Apple certification that still holds up today.

• What to ask an IT provider beyond their certifications, including case studies, references, and whether their approach actually fits your business.

• Why AI governance is likely the next major area of certification and expertise for MSPs.

• A simple rule of thumb for what should never go into an AI tool you don't control.

About Brian Klein:

Brian is an unconventional lawyer who leaves a memorable impression. Known for balancing personality with effective legal counsel, he founded Weinstein + Klein on the belief that practicing law doesn't have to be dull or impersonal. He sees his role as making sure clients are informed, engaged, and maybe even a little entertained along the way.

Brian has earned the respect of clients and peers alike. A testament to his unique approach is the fact that several former adversaries have later become clients (don't worry, he won't share… unless you're sued). He has been recognized throughout his career by legal industry organizations and publications for his work in labor and employment law, including honors from New York Super Lawyers and the New Jersey Legal Awards.

Beyond his practice, Brian has shared his expertise as an Adjunct Professor at Hofstra Law School and contributed commentary and analysis to publications including Eater and the International Business Times. An active member of several bar associations and professional committees, he regularly contributes his insight on labor and employment law issues within the legal community.

About Damien Weinstein:

Co-founder and managing partner of Weinstein and Klein, a law firm representing small and mid-sized businesses in corporate transactional and labor and employment matters. Founded in 2019, Weinstein and Klein has grown from two employees to approximately 25. During this time the firm has appeared twice on the Inc. 5000 list of fastest-growing privately held companies in the U.S. and most recently in 2026 was awarded the Inc. Best Workplaces award.

What you'll learn about in this episode:

• Why the best law firms for small businesses aren't the biggest ones, and how Weinstein & Klein identified a gap between large overpriced firms and under-resourced solos to build something better.
• What "outside general counsel" actually means in practice, and the efficiencies of having a trusted legal partner across employment, corporate, and transactional work.
• A common operational mistake small business owners make, including bottlenecks, and why learning to delegate and hire good people into the right seat is the hardest and most important thing a founder can do.
• Why culture is a main driver of growth at Weinstein & Klein, and how regular touchpoints build a strong team.
• The difference between being kind and being nice, plus why honest feedback is a gift, why "Radical Candor" is worth reading, and why the goal of feedback is to help people succeed.
• How Damien and Brian are using AI to stress-test contracts and run multiple iterations before human review, and why firms that resist this shift are making the same mistake as lawyers who refused to adopt email.
• Why AI-generated contracts are a coming litigation boom.
• Three things to do if you're starting a business today, like partnership agreements, vision and goals, and surrounding yourself with a good network.

In just a few years, Mike and the Chai Travel team have built Chai into one of the fastest-growing travel companies in America and the premiere home for independent travel advisors.

He grew up in the travel industry and knows there's no business as exciting or as rewarding. He feels tremendously privileged to build Chai alongside his family and colleagues.

Mike co-founded Chai Travel after a decade of public service representing victims of domestic violence at the Brooklyn District Attorney's Office.

Beyond Chai, Mike dedicates himself to various political and charitable causes—and to his beloved New York Giants. He lives in Brooklyn, NY with his wife Lindsay and their three children.

What you'll learn about in this episode:

• Why the travel industry's shift from "travel agent" to "travel advisor" isn't just a rebrand, but a move from selling airline seats to becoming a trusted partner for your clients.
• How Mike's father built the largest travel agency in New York starting with a two-person office selling tickets to Tel Aviv, and what that story reveals about what never changes in a service business.
• Steps to take before working with a travel advisor including questions to ask, why you shouldn't try to extract a full itinerary on the first call, and why the best advisors are upfront about fees.
• How Chai Travel used longstanding relationships with in-country contacts to get a stranded traveler home safely during a crisis.
• Why AI won't replace the relationship side of service businesses, but will replace the three or four most annoying, repetitive tasks in your day, and the opportunity that comes follows.
• What volume and relationships mean in the travel industry, and why travel advisors can quickly solve a problem with an airline or hotel.
• Underrated destinations worth putting on your radar, including why Myanmar and South America should be up higher on your list.

About Georg Dauterman:

Georg believes in the fusion of technology and creativity. With a background in both fields, he started his career in IT departments of publishing and advertising agencies, realizing the critical need for tech aligned with business goals. Joining Valiant in 2004, Georg's expertise and passion for efficiency brought industry recognition. He holds a history degree from Queens College and serves on Datto's Global Partner Advisory Board. Beyond his leadership role, Georg enjoys exploring culinary skills, fitness, and outdoor adventures with his family.

About Megan Quick:

Megan is a member of the Valiant Marketing & Sales team, assisting in demonstrating the value of our services and ensuring positive experiences for prospective clients. When not working with technology, she is a theater production manager and performer, producing her own comedy shows, and is an avid writer. Megan has a B.A. in Theater from Sewanee: The University of The South.

• What an IT assessment is, including a snapshot of your infrastructure, security, and applications that tells you exactly where you stand today and what needs to be changed.
• Why the IT assessment is the foundation of every successful MSP relationship, and why skipping it could lead to a rocky start.
• The key difference between an IT assessment and an IT onboarding, and why they may look similar on the surface but serve different purposes and outcomes.
• What the NIST Cybersecurity Framework is, why it's the gold standard for small and mid-market companies, and how to access it for free as a taxpayer-funded public resource.
• How IT assessments vary across remote, hybrid, and in-office environments, and why physical infrastructure introduces complexity that governance based reviews often miss.
• Why Wi-Fi is far more complex than it appears and why a proper Wi-Fi survey is one of the most critical and overlooked parts of an in office assessment.
• The key questions you should ask any IT provider before agreeing to an assessment, including requesting sample deliverables, understand their methodology, and learning how many assessments they perform each year.
• Why your relationship with an IT provider is one of the most important vendor partnerships in your business and why the assessment is an important first step in getting it right.

About Georg Dauterman:

Georg believes in the fusion of technology and creativity. With a background in both fields, he started his career in IT departments of publishing and advertising agencies, realizing the critical need for tech aligned with business goals. Joining Valiant in 2004, Georg's expertise and passion for efficiency brought industry recognition. He holds a history degree from Queens College and serves on Datto's Global Partner Advisory Board. Beyond his leadership role, Georg enjoys exploring culinary skills, fitness, and outdoor adventures with his family.

About Megan Quick:

Megan is a member of the Valiant Marketing & Sales team, assisting in demonstrating the value of our services and ensuring positive experiences for prospective clients. When not working with technology, she is a theater production manager and performer, producing her own comedy shows, and is an avid writer. Megan has a B.A. in Theater from Sewanee: The University of The South.

• Why office moves are one of the most underestimated operational projects a company can take on, and how complexity escalates fast once you start uncovering dependencies.
• A real world example of a client who needed a security guard for a week and a half because an electronic lock wasn't compatible with the building's fire safety system, showing how often unexpected issues arise.
• Why a dedicated move project manager, not your office manager or an early-career employee, is the highest leverage investment you can make, and what a well run move looks like in practice.
• The cost of nebulous responsibility, where every task needs a clear owner with authority to decide, spend, and escalate without leadership bottlenecks.
• Why poor timing around holidays or busy periods is a common and expensive mistake, and why six months lead time should be the baseline.
• Why you shouldn't wait until a move to fix IT issues, since weak Wi-Fi or infrastructure problems will carry over and get worse during the transition.
• How to define a successful move before starting, where employees can walk in on day one, and work without friction.
• The five steps to prepare for a move, including engaging trusted partners early, assigning a move lead, mapping vendors, walking the full project as a team, and integrating the move into regular leadership cadence.

Justin has been with Valiant Technology since 2008 and is a member of our Leadership team. His extensive hands-on experience with technology, particularly Microsoft solutions, can be seen in every solution we implement for clients. An early interest in technology, spanning back as far as high school, has allowed Justin to accumulate a wealth of knowledge on many topics. His first technology-related role was at his Mother's web design company in the 1990's and he's worked with businesses of all sizes since, including web hosting companies and a military contractor.

Justin studied Cinema Studies and Political Science in college, but technology has always been a part of his life. His professional certifications include ones from Microsoft, SonicWall, and Meraki. Justin is also a certified Microsoft Customer Immersion Experience instructor and a certified Google Power Searcher.

When Justin isn't in front of an array of computer screens, he's typically behind his camera capturing photos of birds around the New York Tri-State area, enjoying German beers, and watching cartoons.

What you'll learn about in this episode:

• Why AI should be used as a tool, not a replacement, and where the line falls between work that should remain in the hands of humans, and where AI could be implemented.
• How the AI adoption curve mirrors the cloud revolution and why disruption isn't the technology itself, but the speed it's reaching users.
• The definition of agentic AI, including examples of building an AI agent that reviews your inbox every day so nothing slips through the cracks.
• How Valiant is currently using AI to reduce QBR prep time from 2 hours to 20 minutes, and why this type of automation is where real ROI lives.
• Why businesses should start with Copilot or Gemini before adopting third-party AI platforms.
• The MCP security risk most companies aren't talking about, and how AI tools through open-source Model Context Protocol servers can unintentionally create vulnerable, unprotected data layers.
• Why AI generated output should always be treated as a draft, and how stronger prompting comes from providing context, audience, format, and constraints upfront.
• Why the "AI will replace all jobs" narrative misses the bigger picture, and how AI frees people to focus on creative, strategic, and judgement-heavy work.

About Georg Dauterman: Georg believes in the fusion of technology and creativity. With a background in both fields, he started his career in IT departments of publishing and advertising agencies, realizing the critical need for tech aligned with business goals. Joining Valiant in 2004, Georg's expertise and passion for efficiency brought industry recognition. He holds a history degree from Queens College and serves on Datto's Global Partner Advisory Board. Beyond his leadership role, Georg enjoys exploring culinary skills, fitness, and outdoor adventures with his family.

About Megan Quick: Megan is a member of the Valiant Marketing & Sales team, assisting in demonstrating the value of our services and ensuring positive experiences for prospective clients. When not working with technology, she is a theater production manager and performer, producing her own comedy shows, and is an avid writer. Megan has a B.A. in Theater from Sewanee: The University of The South.

What you'll learn about in this episode:

• Why being the "family IT person" is more common and more consequential than most people realize, and what that responsibility looks like.

• Why both older generations and digital natives were thrown into technology without ever really learning the fundamentals, and how that creates security blind spots at home.

• Cybersecurity habits that you should start today: enable multi-factor authentication, set up a password manager, and audit your bank statements for unauthorized charges.

• How AI-powered deepfakes and voice cloning are making phishing scams far more convincing, and why your family needs a secret code word before transferring money or sharing information.

• The hidden risk in most homes today like smart devices, cameras, garage openers, speakers, and connected appliances that pose a potential security risk and should have its own unique password and regular updates.

• Why scammers rely on urgency, panic or fear, and the easiest mindset shift that can stop most social engineering attacks before they happen.

• How to do a practical home tech audit including changing default passwords and securing your router.

• Practical ways to help less tech-savvy family members become more self-sufficient.