A Guy With A Scarf
§ Course syllabus

Becoming a Better B2B Tech Vendor in Sports and Media

How vendor companies build judgment, deliver under constraint, and earn long-term credibility.

Free intro6 reading chapters · 0a–0f
Lessons12 · numbered 0 → 11
Modules5 movements
Runtime≈ 3 hours of video
MaterialsSlides + audio per lesson
Book10 Things to Consider · 200 pp. PDF
AccessIncluded in the A Guy With A Scarf premium annual subscription on Substack (€399)
LanguageEnglish
§ What this is

Designed for people working on the vendor side of sports and media technology. The course focuses on how deals are really bought, sold, delivered, and judged once systems are live and pressure is real.

It does not teach sales tricks or product tactics. It builds structural understanding and judgment, helping vendors operate credibly across clients, cycles, and long time horizons.

Start here — free introduction

6 chapters · no account needed

Six long-form chapters that orient you to the course — what it is, why it exists, who it is for, who I am, and what the twelve paid lessons actually cover. Read them in order, or jump around. The companion book's full table of contents lives in chapter six.

Intro · 0A
0A
Introduction to Becoming a Better B2B Tech Vendor in Sports and Media
An orientation to the course: what it is, what it is not, and why the material is organised the way it is.
¶ Reading · 10 min read · ~1150 words
Free
Intro · 0B
0B
Why this course
The recurring gap in vendor education — and what this course is built to address.
¶ Reading · 8 min read · ~920 words
Free
Intro · 0C
0C
Who is this course for
The people this course is designed to support — and those who may still find it useful.
¶ Reading · 8 min read · ~880 words
Free
Intro · 0D
0D
Who am I
Two decades on the vendor side. Long enough to have seen several cycles repeat themselves, often with different labels and similar outcomes.
¶ Reading · 7 min read · ~820 words
Free
Intro · 0E
0E
Course content
A walk through the twelve lessons, grouped into five movements from Foundations to Judgment.
¶ Reading · 7 min read · ~700 words
Free
Intro · 0F
0F
The 10 Things to Consider book
The companion book included with enrollment — 51 working lists across 10 categories. Full table of contents inside.
¶ Reading · 6 min read · ~620 words
Free
— end of free introduction —
Paid course · begins below

Twelve lessons. Included with A Guy With A Scarf premium.

Video, slides, and audio for each lesson, plus the full annotated companion book — all bundled into the A Guy With A Scarf premium membership on Substack.

Annual399
Enroll →
Once your membership is confirmed on Substack, we'll email your access link to the course.

The twelve lessons

Lesson 0 → Lesson 11
Mov. I
Foundations
The structural reality
1 lesson
LESSON
00
The structural reality of selling B2B tech in sports and media
This lesson sets the foundation for the entire course. Before talking about products, innovation, delivery, or partnership, it clarifies the structural environment in which B2B tech vendors operate in sports and media. Many frustrations vendors experience do not come from weak execution or poor intent. They come from misreading the system they are selling into. Lesson 0 explains why sports and media organisations behave differently from typical enterprise clients, how power and accountability are distributed, and why live operations, visibility, pace, and accumulated complexity shape outcomes in ways vendors often underestimate. The goal of this lesson is to help vendors recognise what is structural, what is within their control, and where judgment matters most. Everything that follows in the course builds on this shared understanding.
▸ Video · 13 min◆ Slides · 13 pp.▢ Preview
Preview
Mov. II
The Transaction
Buying, selling, and the design of the deal
3 lessons
LESSON
01
What clients are actually buying
This lesson focuses on the gap between what vendors think they are selling and what clients believe they are buying. It breaks down how sports and media organisations frame value when they engage a technology vendor, including expectations around outcomes, risk transfer, credibility, and support. The lesson looks at how technology is often purchased as a means to reduce uncertainty, accelerate delivery, or protect internal teams, rather than for features alone. You will explore how these buying motivations shape decisions, influence success criteria, and create hidden tensions once projects move from contract to delivery. This lesson helps vendors better understand client intent, align proposals with real priorities, and avoid early misunderstandings that later turn into friction.
▸ Video · 17 min◆ Slides · 17 pp.▢ Preview
Preview
LESSON
02
What vendors are actually selling
This lesson examines the reality of what a technology vendor brings into a sports and media organisation, beyond the product itself. It looks at how vendors are evaluated through their ability to reduce complexity, absorb risk, operate under pressure, and make decisions when conditions change. The lesson unpacks the mix of technology, service, judgment, and availability that clients implicitly expect once a vendor is engaged. You will explore how vendor positioning, team structure, and delivery behaviour shape trust over time, often more than features or roadmaps. The lesson also highlights common mismatches between how vendors describe their offering and how clients experience it in practice. This lesson helps vendors understand their real role inside a client organisation and take clearer responsibility for how they are perceived once work begins.
▸ Video · 11 min◆ Slides · 13 pp.+ Extra PDF▢ Preview
Preview
LESSON
03
Designing the deal to match the purchase
This lesson focuses on how deal design shapes delivery reality long before work begins. It explains why contracts in sports and media are operational designs, not just legal documents, and how pricing models, staffing commitments, timelines, and scope definitions embed assumptions about risk, pace, visibility, and accountability. The lesson examines different deal entry points, including RFPs, RFIs, and direct sales, and how each constrains what vendors can realistically deliver. It explores power imbalances, pre-contract work, and how optimism and ambiguity create problems that only surface later under pressure. You will learn how misaligned deals lead to scope creep, permanent service, and burnout, and why clarity is the vendor's primary protection. The lesson closes with the core disciplines vendors must apply to design deals that survive real operating conditions and enable calmer, more sustainable delivery.
▸ Video · 17 min◆ Slides · 13 pp.+ Extra PDF▢ Preview
Preview
Mov. III
Delivery
Complexity, live sport, data, accountability
3 lessons
LESSON
04
Complexity, pace, and why strong technology still struggles
This lesson examines a familiar pattern in sports and media projects: the technology works, yet outcomes disappoint. It explains how failure often emerges from accumulated complexity and delivery pace rather than from poor engineering. The lesson reframes complexity as the interaction of technology, organisations, governance, contracts, and operations over time, and shows why these factors are structural in sports and media environments. You will explore how complexity grows quietly, how pace becomes an unspoken design choice, and why both slow delivery and excessive speed create similar risks. The lesson also looks at how vendors unintentionally add load, how service and heroics hide structural problems, and why effort is often mistaken for stability. The focus is on designing for absorption rather than momentum, helping vendors make progress that can be sustained without burnout, fragility, or loss of trust.
▸ Video · 12 min◆ Slides · 14 pp.▢ Preview
Preview
LESSON
05
Designing, building, and operating for live sport
This lesson explores what changes when technology is exposed to live sport conditions, where time is fixed, failure is public, and recovery options are limited. It explains why live sport is a fundamentally different operating environment and how asymmetric risk, emotional pressure, and public visibility reshape how systems must be designed and operated. The lesson focuses on live-first design choices, preparation over optimisation, and the organisational discipline required to deliver reliably under pressure. You will examine how vendors are judged during live moments, why overpromising creates long-term risk, and why great troubleshooters matter as much as architecture. The lesson also covers shared responsibility during live delivery, escalation clarity, and the behaviours vendors must protect to build lasting credibility across seasons. This lesson helps vendors design systems and operating models that survive real-world live conditions and earn trust over time.
▸ Video · 19 min◆ Slides · 14 pp.+ Extra PDF▢ Preview
Preview
LESSON
06
Data, risk, and accountability
This lesson examines how data reshapes responsibility once systems move from project phase into live operation. It explores who owns data, who carries risk when data is wrong, delayed, incomplete, or misunderstood, and how accountability is distributed across vendors, clients, and partners in sports and media environments. The lesson looks at data not just as an asset, but as a source of operational pressure, decision exposure, and trust. You will examine how live data amplifies consequences, why unclear data ownership creates hidden risk, and how reporting, monitoring, and dashboards can either protect or expose vendors during incidents. The lesson also covers how data obligations evolve over time, and why vendors are often judged on interpretation and response, not just accuracy. This lesson helps vendors design clearer data responsibilities, reduce ambiguity, and operate with credibility when decisions depend on real-time information.
▸ Video · 16 min◆ Slides · 11 pp.▢ Preview
Preview
Mov. IV
The Long Run
Service, scale, and client cycles
3 lessons
LESSON
07
Service, success, and the limits of partnership
This lesson examines what happens once a project moves beyond go-live and into sustained operation. At this stage, plans, contracts, and roadmaps fade into the background, while day-to-day interaction becomes central. Service turns into the main interface between vendor and client, and the quality of that interface increasingly defines how the relationship is perceived. The lesson explores how definitions of success change over time. Early success is often associated with launch milestones, feature delivery, or initial performance indicators. As systems remain live, success becomes tied to stability, predictability, and how issues are handled when pressure is high. Vendors often continue to deliver what was agreed, yet still feel that expectations have shifted. This lesson helps explain why. It also looks closely at the idea of partnership. Partnership language is common in sports and media projects, but its meaning is rarely clear or stable. Over time, service interactions expose where responsibility is shared, where it is not, and how accountability gradually settles. Vendors who do not recognise these limits often overextend themselves, while those who disengage too early risk losing trust. By the end of the lesson, vendors should have a clearer understanding of how service shapes long-term perception, how success is actually evaluated after go-live, and how to operate credibly within the practical limits of partnership in complex, live environments.
▸ Video · 15 min◆ Slides · 10 pp.▢ Preview
Preview
LESSON
08
Mega clients, scale, and asymmetric risk
This lesson examines what changes when vendors begin working with mega clients in sports and media. These relationships often represent a step change in scale, visibility, and strategic importance. They can be company-defining, accelerating investment, operational maturity, and market positioning. At the same time, they introduce structural imbalances and long-term risks that are easy to underestimate at the outset. The lesson explores why vendors pursue mega clients and what distinguishes these organisations beyond size alone. It looks at how complexity, public visibility, and institutional memory shape every interaction, and how success and failure propagate differently when recognised brands are involved. The lesson shows how scale amplifies both strengths and weaknesses inside the vendor organisation, influencing product strategy, delivery priorities, and internal alignment. A central focus is asymmetric risk. Mega clients can absorb delays, pivots, and failure in ways vendors cannot. This imbalance affects timing, urgency, accountability, and decision-making. The lesson examines how product gravity develops over time, how custom work becomes embedded, and how reputation becomes tightly coupled to outcomes that are only partially under the vendor's control. By the end of the lesson, vendors should have a clearer understanding of why mega clients can accelerate growth and credibility, where structural risk actually sits, and what disciplines are required to protect long-term resilience while engaging at scale.
▸ Video · 15 min◆ Slides · 13 pp.▢ Preview
Preview
LESSON
09
Client cycles and operating model shifts
This lesson focuses on how client operating models evolve over time, and why these shifts are a normal structural feature of sports and media organisations rather than an exception. Clients regularly change how work is organised, funded, governed, and delivered in response to scale, scrutiny, leadership transitions, and market pressure. For vendors, the most difficult moments often occur when these shifts happen quietly while assumptions remain unchanged. The lesson explores the main operating model patterns vendors encounter. It looks at phases of externalisation, where clients push responsibility outward to gain speed and flexibility, and phases of internalisation, where capability is pulled back inside to regain control, predictability, and accountability. It also examines hybrid models that emerge through value-in-kind arrangements, technology sponsorships, and platform outsourcing, all of which introduce additional complexity around ownership and responsibility. A central theme of the lesson is judgment over time. Vendors who treat a client's current model as permanent tend to optimise too narrowly and are caught off guard when structures change. Strong vendors expect movement as a baseline condition. They learn to read early signals embedded in service interactions, governance language, and escalation patterns, and adjust their posture before pressure peaks. By the end of the lesson, vendors should have a clearer understanding of why operating model shifts are inevitable, how risk and opportunity vary across each phase, and how to remain credible by adapting without overreacting or misreading client intent.
▸ Video · 19 min◆ Slides · 13 pp.▢ Preview
Preview
Mov. V
Judgment
Initiative, credibility, survival
2 lessons
LESSON
10
Innovation, initiative, and knowing when to stay in your lane
This lesson focuses on a tension most vendors recognise immediately. Clients expect proactive ideas, strategic input, and thought leadership from their partners. At the same time, those same ideas are often resisted when timing, context, or organisational readiness are misaligned. The result is confusion on the vendor side about when initiative is valued and when it creates friction. The lesson explores how innovation is interpreted in real client environments. It looks at the difference between initiative that lands and intrusion that backfires, showing how context, timing, and internal structure matter more than idea quality alone. Vendors are encouraged to see innovation as situational, shaped by delivery pressure, governance constraints, and the client's current focus. A central theme is restraint as a form of judgment. The lesson explains why holding back can protect credibility during certain phases, and why constant proposing often dilutes impact rather than increasing value. It also broadens the definition of innovation beyond product features, highlighting operational, delivery, risk, and governance initiatives that often create more immediate trust. By the end of the lesson, vendors should have a clearer sense of how to read signals, choose moments deliberately, and understand innovation as something earned over time through reliable delivery and predictable behaviour.
▸ Video · 11 min◆ Slides · 12 pp.▢ Preview
Preview
LESSON
11
Judgment, credibility, and long-term vendor survival and growth
This final lesson steps back from individual deals, delivery challenges, and client situations to look at what allows vendors to last over time. It focuses on durability rather than performance in any single moment, and on how credibility is built, tested, and sometimes lost across years of operating under pressure in sports and media environments. The lesson explores why strong vendors often disappear quietly. Not through sudden failure, but through gradual erosion caused by accumulated complexity, concentrated revenue, and a series of small decisions that felt reasonable when they were made. It shows how adaptability can narrow over time, and how organisations lose flexibility without realising it. A central theme is judgment. The lesson examines where judgment actually becomes visible, particularly in moments of constraint, when short-term incentives conflict with long-term sustainability. It looks at decisions around scope, revenue, responsibility, and accountability, and how these choices shape reputation more than technical success. The lesson also addresses growth, not as expansion at any cost, but as a process that reinforces discipline rather than distorting it. It highlights the importance of reliability, recoverability, and internal memory, and explains why how relationships end matters as much as how they begin. By the end of the lesson, vendors should have a clearer understanding of how credibility accumulates over time, why it is fragile under pressure, and how long-term survival and growth depend on judgment exercised consistently across many small decisions.
▸ Video · 11 min◆ Slides · 12 pp.▢ Preview
Preview
§ What you get
01 · Video lessons
12 × ≈15 min
Streamed in HD. Downloadable for offline viewing. Chapter markers and transcripts throughout.
02 · Companion book
200 pp. · 51 lists
The full annotated 10 Things to Consider book, included with enrollment. One reference for the whole course.
03 · Slides + audio
Per lesson
The slide deck from each video, plus an audio-only track. Occasional extra reference PDFs for specific lessons.
A Guy With A Scarf premium · open

One annual subscription.
Course included.

Annual399
IncludesCourse · book · newsletter
Enroll →
Once your membership is confirmed on Substack, we'll email your access link to the course.