Enrollment Is the Missing Link in Strategic Planning
Your strategy failed because nobody was enrolled.
Why do strategies fail? It’s a popular business question with endless theories—frameworks, business models, competitive positioning, value creation.
I’ll leave that to HBR.
Here’s my thesis: companies minimize the need to enroll employees and stakeholders during the strategic process. So implementation falls short.
Enrollment isn’t a soft skill or HR buzzword. It’s the art of facilitating the behavioral, cultural, and human elements that need to be in place for people to make decisions and take action toward desired outcomes.
Without enrollment, you get a beautiful deck that sits on a shelf while everyone goes back to doing what they were doing before.
Strategy Isn't a Product
Most strategic planning processes optimize for speed and polish—consultants build the deck, executives present to the board, then announce the new strategy. Six months later, nobody can tell you what it is because they were never enrolled.
Your strategy failed because nobody was enrolled.
Why do strategies fail? It’s a popular business question with endless theories—frameworks, business models, competitive positioning, value creation.
I’ll leave that to HBR.
Here’s my thesis: companies minimize the need to enroll employees and stakeholders during the strategic process. So implementation falls short.
Enrollment isn’t a soft skill or HR buzzword. It’s the art of facilitating the behavioral, cultural, and human elements that need to be in place for people to make decisions and take action toward desired outcomes.
Without enrollment, you get a beautiful deck that sits on a shelf while everyone goes back to doing what they were doing before.
Work backward from success.
Let me visualize what success looks like and reverse-engineer it.
A successful strategy is executed by an accountable team with autonomy to experiment and make choices to achieve outcomes.
For a team to feel accountable, they need to be enrolled.
To be enrolled, they need to participate in strategic planning—or at minimum, the communication of the plan.
For teams to participate meaningfully, there needs to be executive commitment and a thoughtful strategic process design.
The chain looks like this:
Executive Commitment → Participation/Communication → Enrollment → Accountability
Break any link, and the strategy dies in PowerPoint.
The best strategies are narratives.
Great strategies are stories. They take stakeholders on a journey—historical perspective, present environment, future state—where humans execute choreographed tactics to achieve specific outcomes.
The operative word: human.
Management consultancies are incredibly competent at building strategic narratives. McKinsey can craft a story that makes your board weep with inspiration.
The challenge is turning that story into reality. And that requires enrollment from the people who actually have to execute it.
Embed internal teams early.
I advocate embedding an internal cross-functional, high-performance team with strategic leaders or third-party consultancies throughout the entire strategic process.
Short term, this adds complexity. It slows things down. It creates discomfort.
But that discomfort is where the magic happens. Suffering during the planning process is critical for enrollment.
Suffering forces cross-functional problem-solving among the practitioners within the organization—the people who will actually do the work. Without doers involved, strategy becomes academic. It becomes consultant theater that looks impressive but has no connection to operational reality.
Design the process intentionally.
Here’s my checklist for any strategic planning project:
1. Find and build a balanced internal team.
I identify this team during early stakeholder interviews. I probe: who are the high-potential employees? Who does everyone go to with questions?
Planning processes are excellent opportunities for people searching for stretch assignments. Find your A-players who want visibility and give them meaningful roles.
2. Keep everything visually in one place.
Ideally, a war room—an actual conference room where work lives on the walls. Or a virtual whiteboard like Miro.
Seeing the work develop enables strategic themes to emerge naturally. When everything is scattered across email threads and individual laptops, connections get missed.
3. Divide up the workstreams.
Create mini-teams to investigate and execute questions or issues derived from the planning group. Have them own and present their work.
Ownership creates accountability. If someone is responsible for customer segmentation analysis and has to present it to leadership, they’ll do better work than if they’re just “helping out.”
4. Facilitate and provide tools, knowledge, and coaching.
I embed myself on these teams as a player-coach. I help teams discover answers and provide guidance on executing workstreams.
For example, if a team has a customer segmentation workstream and struggles to get started, I offer methodologies and resources. But they do the work. They own the insights.
5. Over-communicate, especially with leadership.
Invite leaders into the war room—virtually or physically—and regularly walk through completed workstreams and learnings.
Be open to feedback. Make adjustments in real-time. This prevents the “big reveal” moment where leadership sees the strategy for the first time and hates it. By then, you’ve invested months and burned credibility.
6. Write the narrative before building the deck.
Before any PowerPoint, have the team write the narrative using only words. Walk through analyses, learnings, themes, initiatives, financials, and desired outcomes in prose.
Iterate. Get the entire team to sign off on the story.
Then—and only then—build the deck.
Most teams do this backward. They build slides and retrofit a narrative. The result is disjointed, jargon-heavy presentations that don’t tell a coherent story.
7. Let the team be your advocates.
I love when members of the planning team go back to their functional groups and present the strategy themselves.
If one of their own is enrolled and excited, it engenders commitment faster than any top-down mandate. Peer-to-peer communication is more credible than executive pronouncements.
8. Run a road show.
Review the strategy individually with the board, C-suite, senior leaders, and small intimate groups across the organization.
The goal: get maximum feedback and make adjustments as necessary.
Road shows grease the wheels for final plan approval and capital/resource requests. By the time you’re asking for formal approval, there should be no surprises. Everyone should have seen it, touched it, and influenced it.
Why this matters.
Adding these elements to your strategic planning process catalyzes participation, which enables enrollment, which drives accountability.
Execution succeeds when teams are enrolled and accountable.
Most strategic planning processes optimize for speed and polish. Get the consultants in. Build the deck. Present to the board. Announce the new strategy.
Then nothing changes.
That approach treats strategy like a product you deliver to the organization. “Here’s your new strategy. Now go execute it.”
But strategy isn’t a product. It’s a change in behavior across hundreds or thousands of people. And behavior change requires enrollment—not just communication.
The cost of skipping enrollment.
I’ve seen companies spend millions on strategic planning. Beautiful frameworks. Detailed financial models. Impressive decks with custom illustrations.
Then six months later, nobody can tell you what the strategy is. Teams are still operating under old priorities. Resources are allocated the same way they were before. Initiatives launch and die quietly.
Why? Because nobody was enrolled. The strategy was created in a conference room by executives and consultants, then announced to the organization as a fait accompli.
People don’t resist change. They resist being changed. When you involve teams early, let them suffer through the hard questions, give them ownership of workstreams—they become co-creators, not recipients.
Co-creators fight for the strategy. Recipients ignore it.
The takeaway.
Your strategy failed because it was built in isolation and delivered as a finished product.
Next time, slow down. Embed internal teams early. Let them struggle with the hard questions. Give them ownership. Over-communicate. Write the narrative before the deck. Turn them into advocates.
It’s messier. It’s slower. It’s harder to control.
But the strategy that emerges will be executable—because the people who have to execute it were enrolled from the beginning.
Enrollment isn’t optional. It’s the difference between strategy as theater and strategy as transformation.
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Why Revenue Operations Is Replacing Sales and Marketing
Sales and marketing are fighting because the org chart is broken.
I’ve watched friction between sales and marketing intensify over the last decade. Mistrust. Finger-pointing. Competing KPIs that don’t align with actual business goals.
The root cause isn’t people—it’s structure. Digital automation blurred the lines of who owns what in the customer journey. Marketing owns awareness but also nurtures leads. Sales closes deals but also educates prospects. Customer service retains accounts but also upsells.
Where does marketing end and sales begin? Nobody knows anymore. So teams protect turf, build separate tech stacks, and produce conflicting reports that make leadership decisions harder instead of easier.
There’s a better way.
Revenue Unifies Competing Functions
Sales and marketing titles carry decades of baggage—territorial behavior, separate tech stacks, and misaligned incentives. Activity-oriented roles force you to think about what actually needs to happen to acquire and retain customers in 2025.
Sales and marketing are fighting because the org chart is broken.
I’ve watched friction between sales and marketing intensify over the last decade. Mistrust. Finger-pointing. Competing KPIs that don’t align with actual business goals.
The root cause isn’t people—it’s structure. Digital automation blurred the lines of who owns what in the customer journey. Marketing owns awareness but also nurtures leads. Sales closes deals but also educates prospects. Customer service retains accounts but also upsells.
Where does marketing end and sales begin? Nobody knows anymore. So teams protect turf, build separate tech stacks, and produce conflicting reports that make leadership decisions harder instead of easier.
There’s a better way.
How we got here.
Modern sales and marketing emerged in the 1950s post-industrial boom. Think Mad Men. As competition increased and consumers gained choice, marketers developed techniques to generate interest and differentiation.
Sales practices go back further—early salesmen were known for aggressive door-to-door techniques during the Great Depression. Trading and bartering date back centuries. Sales is one of the oldest professions.
Marketing’s history is murkier. There’s debate about definitions, phases, and when “marketing” as a practice actually began.
But here’s what mattered: through the late 19th and 20th centuries, sales and marketing lived in harmony. Clear delineation. Simple KPIs. Early media channels that were easy to measure. Marketing generated interest. Sales closed deals. It worked.
Then Web 2.0 happened.
E-commerce. Digital sales and marketing. Social media. New customer data and segmentation capabilities. The marketing funnel—originally devised in 1898 by E. St. Elmo Lewis—got operationalized with technology.
The buyer journey fundamentally changed.
Both functions splintered into specializations. Brand marketing. Performance marketing. SEO/SEM. Product marketing. Content marketing. Marketing analytics. SDRs. BDRs. AEs. Inside sales. Outside sales. Digital everything.
Like engines, the more moving parts, the more things break.
Separate stacks, separate truths.
Over the last decade, some organizations started identifying the real problem: sales, marketing, and customer service were building independent operating stacks, producing separate KPIs, and creating conflicting narratives.
Each function rolled up its own reports. Leadership couldn’t get a single source of truth. Decision-making became political. Resource prioritization turned into turf wars.
The best organizations adapted. They collapsed these functions under unified revenue structures—Chief Revenue Officers (CROs), Chief Growth Officers (CGOs), supported by Revenue Operations teams that connect processes, people, technology, and systems.
This provided a unifying goal: revenue growth. It reduced mistrust. It made organizations leaner and faster.
Like biological systems, the best companies adapt to stressors and devise more efficient structures to survive.
A thought experiment.
Here’s an exercise: if I started a generic SaaS company tomorrow, how would I organize customer-facing teams without using “sales” or “marketing” titles?
What would the structure look like if I used activity-oriented roles instead of legacy function names?
Could I explain it to a six-year-old?
The framework: customer decision journey.
First, I need clarity on what drives revenue. A customer exchanges money for a product or service that generates value—real or perceived.
Assuming product-market fit, revenue increases by acquiring and retaining customers.
But how do you acquire and retain customers in a digital-first world?
The traditional marketing funnel has had a 100+ year run. But explaining “awareness, familiarity, consideration, intent, and loyalty” to a six-year-old is impossible.
McKinsey published research in 2009 proposing a new customer decision journey map. It’s more intuitive. Minimal sales and marketing jargon. Descriptive language that feels relatable today.
I tested it with my six-year-old. Much easier to explain. The loyalty loop was a hit.
The journey breaks into two stages:
- Acquisition (top half): attract and commit customers to purchase
- Retention (bottom half): support value after purchase, build loyalty
Building the team.
At the top: a Chief Revenue Officer (CRO). I want revenue in the title for clarity. The CRO needs fluency in acquisition and retention, strong leadership, cohesive storytelling, financial discipline, and technical understanding.
Reporting to the CRO: Acquisition Lead (AL) and Retention Lead (RL).
The AL is a hunter—clear vision for attracting and closing prospects across the acquisition journey.
The RL is a farmer—adept at creating lasting relationships, educating customers, solving problems, and generating loyalty.
Acquisition roles.
To land on a customer’s initial consideration set, you must capture positive attention wherever that attention lives—passive browsing or active searching.
Prospect Librarian — Segments prospects to maximize attention. Understands who’s searching, where they’re looking, and what content resonates.
Search Attention Wizards — Optimize for active search behavior.
Attention Content Creators — Build content that grabs eyeballs.
Attention Campaign Planners — Orchestrate multi-channel campaigns.
Non-Digital Attention Gurus — Handle offline channels (yes, they still matter).
Once you have attention and positive first impressions, prospects enter research mode. They’ll research online, talk to current customers, ask professional communities, meet with reps, watch videos, attend events, compare competitors, and test the product.
You need people excellent at creating narratives, building relationships, participating in communities, developing media, planning events, and providing informative content across digital and analog channels that drive positive perceptions and trust.
Moment of purchase.
The customer has passed attention, consideration, and research. They’re on the cusp of a decision—McKinsey’s “moment of purchase.”
An agreement happens between customer and company to exchange product for compensation. This may happen with or without human interaction.
Agreement Experience Team — Makes the buying experience effortless, whether self-serve or human-assisted.
Empathetic Closers — For prospects needing additional convincing, these are relationship-focused negotiators who close agreements without pressure tactics.
Retention roles.
The retention game begins immediately after purchase.
Onboarding Wizards — Create unforgettable first impressions. Get customers to value fast.
Relationship Shamans — Maintain ongoing customer relationships. Check-ins. QBRs. Expansion conversations.
Self-Help Facilitators — Build content for customers who prefer to solve problems independently. Knowledge bases. Video tutorials. Community forums.
Customer SWAT Team — For customers needing human support, these problem-solvers move fast with empathy.
Retention Magicians — Identify at-risk customers and create solutions to convince them to stay (within reason). Early warning systems. Intervention strategies.
Retention is underfunded in most organizations. But I’d argue it’s equally—if not more—important than acquisition. Keeping customers is cheaper than finding new ones. And loyal customers expand.
In this organization, retention gets equal priority and budget to acquisition.
The connective tissue.
Two critical threads span the entire customer journey:
Storyteller Lead — Weaves together product names, brand identity, visual appearance, meaning, and humanizes the company. This isn’t “branding fluff”—it’s the connective tissue that makes everything else work.
Measurement Lead — Owns data, analytics, and reporting across the full customer journey. Single source of truth. One KPI rules them all: revenue growth.
Both report directly to the CRO.
The takeaway.
This exercise isn’t a rigid org chart. It’s a way to trigger first-principles thinking about organizational design.
Sales and marketing titles carry baggage—decades of functional separation, territorial behavior, and misaligned incentives. Activity-oriented roles force you to think about what actually needs to happen to acquire and retain customers.
You can run this exercise with your team. Debate it. Get creative. Have fun with the titles. The goal isn’t perfect structure—it’s identifying blind spots, root causes of friction, and whether your org chart matches how customers actually buy today.
Even if you’re not ready for organizational change, this exercise will surface problems you didn’t know you had.
The real question.
Does your organizational structure reflect 2025 buyer behavior? Or is it optimized for 1995?
If sales and marketing are fighting, the answer is probably the latter.
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Two New MVPs: Minimum Viable Process and Planning
Innovation doesn’t scale. Stop trying to make it.
You’ve heard of Minimum Viable Product—Eric Ries coined the term to describe a version of a product that offers maximum learning at minimal effort.
Here are two more MVPs: Minimum Viable Process and Minimum Viable Planning.
Most companies get MVP culture right at the beginning. Then they grow, add systems, and accidentally kill the thing that made them successful in the first place.
Innovation Doesn't Scale Well
Most companies get MVP culture right at the beginning. Then they grow, add systems, and accidentally kill the thing that made them successful in the first place.
The rule of 3 and 10.
I’ve worked with companies at every stage—early startups to Fortune 50 enterprises. There’s a framework that helps explain what happens as companies scale: the rule of 3 and 10.
Hiroshi Mikitani, CEO of Rakuten, observed that as companies grow in multiples of 3 and powers of 10, systems and processes start breaking down. What works with 3 people doesn’t work at 30. What works at 30 doesn’t work at 90, 270, and so on.
I generally agree with this for most functions—finance, operations, sales, marketing. These areas need systems to scale.
But there’s one exception: innovation.
The startup phase: chaos works.
Startups have one job: find product-market fit with minimal distraction. That means failing fast, shipping MVPs, absorbing customer feedback, and iterating without overthinking it.
There’s no time for elaborate planning. Expensive tech stacks, formal processes, hierarchies—all of that can wait. You’re moving too fast to build scaffolding.
The scale trap: growing up too fast.
Once companies find product-market fit, sign initial customers, and start growing, basic systems get implemented. This is necessary—without some structure, profitability becomes unreachable.
But here’s where it goes wrong: there’s a gravitational pull to add process, planning, and technology too soon. Companies start building for future scale before they’ve proven current traction.
Scaling infrastructure prematurely overheats resources, burns capital, and distracts from revenue growth. Worse, innovation suffers because added processes create friction. The speed that got you here slows to a crawl.
The enterprise phase: the giant hairball.
Years of growth mean layers of products, businesses, technology, systems, rules, traditions, and processes. Gordon Mackenzie called this “orbiting the giant hairball”—an ecosystem that consciously or subconsciously wrings risk out of the organization.
Employees execute defined routines with little upside to innovate. Risk-taking gets punished. Mavericks get treated like viruses—corporate antibodies attack until the innovators leave or conform.
Innovation becomes incremental product improvements instead of disruptive new business models. Stage-gate processes with five layers of approval. Five-year plans that are outdated before they’re finished. Six Sigma rigor applied to exploring the unknown.
It’s all designed to reduce risk. And it works—by also eliminating the conditions that create breakthroughs.
The permanent MVP state.
Here’s my thesis: organizations should resist scaling processes and planning specific to innovation functions at all growth stages.
Minimum Viable Product, Minimum Viable Process, and Minimum Viable Planning should be the permanent state for new technology, product, and business model innovation.
Innovation culture should not grow up. It should maintain MVP vitality forever—regardless of whether the company has 30 employees or 30,000.
Why Elon gets away with it.
Love him or hate him, Elon Musk routinely wills a general concept into a billion-dollar business across industries. Ideas that would die immediately in most organizations.
Why? He thinks in first principles. He asks questions the way a child would—without baggage, without “that’s not how we do things here.” But he combines that childlike curiosity with advanced intellect and experience.
His other differentiator: bias for action. He ships. He tests. He breaks things and learns fast.
Most enterprises have the intellect and resources. What they lack is the willingness to stay in permanent startup mode for their innovation functions.
How to keep innovation wild.
Here’s how to maintain an MVP innovation culture as you scale:
1. Keep teams small.
Product development teams should stay under 10 people. Independent. Autonomous. Free to chase seemingly crazy ideas.
In my experience, five teams of five working on the same problem outperform one team of 25. Small teams move faster, communicate better, and don’t need three layers of approval to make decisions.
2. Go agile, actually.
Agile methodology is standard in startups, especially for developers. It’s less common in enterprises still clinging to waterfall processes.
Invest in real agile training across functions—not the bastardized “agile” that just means more meetings.
3. Use simple frameworks.
Business Model Canvas is visual and straightforward. It forces you to think through key assumptions on one page.
If your planning document is longer than one page in the early stages, it’s probably too much. You’re planning instead of learning.
4. Build internal VC funding mechanisms.
Many large enterprises have corporate VC arms to invest externally. Let internal innovation teams tap the same funding mechanisms.
Keep the process simple—no 47-slide decks to get $50K for an MVP.
5. Kill stage-gate processes for innovation.
This is hard for me to say—I’ve advocated for stage-gate processes most of my career. But they don’t work for early-stage innovation.
Develop a simple prioritization framework. Start working on the best ideas. Iterate based on what you learn, not what the stage-gate calendar says.
6. Stay horizontal.
Layers of hierarchy kill decision-making speed. Stick with horizontal org designs as much as possible for innovation teams.
If someone needs three approvals to run a $5K experiment, you’ve already lost.
7. Protect the mavericks.
I’ve heard the talk in large corporations about embracing risk-taking and entrepreneurial culture. I have not experienced it being real.
Risk-taking and failure lead to corporate exits—voluntary or involuntary. Mavericks get treated like threats. For every maverick pushing boundaries, there are ten employees rooting for them to fail so things can go back to normal.
In startups, everyone is a maverick—or they’d find less risky jobs that pay more. Enterprises need to create protected spaces where mavericks can operate without corporate antibodies attacking them.
8. Simple financial modeling.
I’m guilty of building complex financial models in early-stage product development. My learning: a simple model works just as well to determine if you’re on the right track.
You don’t need 20-year forecasts with sensitivity analyses when you’re testing whether anyone wants the product.
The takeaway.
Companies scale. They add systems, processes, technology, people, and planning. That’s fine—most functions need structure to operate efficiently.
But innovation is different. It’s an animal that needs to stay a little wild.
As companies grow, they try to cage the innovation function. Bring it under control. Make it predictable. Reduce the risk.
Resist.
Keep your innovation engine in permanent MVP mode. Small teams. Simple frameworks. Bias for action. Protection for mavericks.
Scale the parts of your business that benefit from systems. Keep innovation chaotic, fast, and a little bit dangerous.
That’s where breakthroughs come from.
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Survive the Capital Crunch: A Guide to Positive Free Cash Flow
The cheap money era is over. Most companies haven’t noticed.
I fell down a rabbit hole recently. Debt financing. Interest rate charts spanning fifty years. Treasuries, mortgages, yield spreads, SBA loans, debt across every credit profile.
One conclusion kept surfacing: debt was absurdly cheap from 2016 through 2021. Not since the 1950s has the US—or most developed nations—had access to capital this inexpensive.
So I asked myself: why did so many early-stage companies chase equity financing when debt was practically free?
Free Cash Flow Matters
From 2016 through 2021, both debt and equity were historically cheap—a perfect storm that may never repeat. Companies optimized for growth because that’s what got rewarded. That playbook is dead.
Because equity was even cheaper.
The last five years created a perfect storm. Valuations exploded. P/E ratios hit levels we hadn’t seen since the dot-com bubble. Funding supply was abundant—SPACs, innovative convertible instruments, the crypto explosion. Competition for deals drove valuations higher, which meant venture-backed companies could raise more capital with less dilution.
Equity financing became cheaper than debt. That almost never happens.
I started digging into historical data, looking for other periods where both equity and debt financing were simultaneously cheap. I couldn’t find one. The cost of capital across most risk categories from 2016 through 2021 appears to be a historical anomaly—the bottom.
WACC (weighted average cost of capital) time series data from Seeking Alpha confirms this. The chart is stark. We just lived through the cheapest capital environment in modern history.
The ship has sailed.
In 2022, financing costs started climbing fast. Debt got expensive. Equity valuations corrected. The era of cheap, unlimited capital ended abruptly.
If your company is less than ten years old, you’ve never operated in an expensive capital environment. Congrats if you took advantage and built a cash cushion. But most didn’t. They optimized for revenue growth because that’s what got rewarded with unicorn valuations and easy follow-on rounds.
That playbook is dead.
Free cash flow is the new religion.
Companies must pivot—hard—toward positive free cash flow (FCF) or risk running out of runway in an environment where the next capital raise comes with massive dilution or doesn’t come at all.
FCF isn’t the same as net income. It adds back non-cash expenses like depreciation and amortization. It adjusts for capital expenditures, working capital changes, and actual cash in/out. It tells you whether your business generates cash or consumes it.
Companies with positive FCF can survive prolonged recessions, stagflation, and stricter financing conditions. They have options. They control their destiny.
Companies with negative FCF are on a timer. Once the current cash position evaporates, they’re at the mercy of investors who now have leverage and will extract painful terms.
How to get to positive FCF.
Reaching positive free cash flow requires looking at the entire financial picture—P&L, balance sheet, and cash flow statement. Here are tactical levers to pull:
1. Renegotiate payment terms.
Work with vendors and customers to adjust accounts payable and receivable terms. Extend terms with vendors. Reduce terms with customers—even if it means offering discounts or paying slightly more for faster payment.
With high inflation, minimizing net working capital needs is critical. Working capital is current liabilities minus current assets. If that balance tilts wrong, generous customer terms eat cash fast.
2. Build a money map.
Document every cash expenditure from the last twelve months. Rank by total expense. Categorize each as critical or non-critical to operating the business.
Pause or stop non-critical costs immediately. Renegotiate with your largest vendors—even small percentage reductions compound. Most vendors would rather keep you as a customer at a lower rate than lose you entirely.
3. Delay or reduce capital expenditures.
Pause all CapEx except investments that reduce operating costs within twelve months. Prioritize short-term break-even projects. Everything else can wait.
4. Shift from fixed to variable costs.
Variable cost structures let you flex based on business performance. It feels counterintuitive, but contractors can fill resource gaps as variable costs instead of fixed headcount. You pay for what you use, not what you forecasted six months ago.
5. Automate with performance-based deals.
Look for RPA (robotic process automation) opportunities, but negotiate performance-based payment models. If the RPA saves you $100K, pay a percentage of the savings instead of upfront service fees. Align vendor incentives with actual results.
6. Do less.
Everything has a cost—including strategic initiatives that sound important but don’t move the needle. If you have eight priorities, cut to four. Eliminate waste. Kill projects that don’t directly contribute to cash generation.
7. Cut the lavish stuff.
Company events, conventions, travel, office leases, furniture, team dinners—reduce or eliminate. This isn’t forever. But right now, survival matters more than culture perks.
8. Pull the hard levers.
Cost reduction, workforce right-sizing, price increases. These are pragmatic, painful levers. But they generate cash fast when you’re against the clock.
9. Secure a revolving line of credit.
Even if it’s expensive, a revolver acts as insurance during rough patches. Access to emergency cash can bridge working capital gaps and buy you time to execute a turnaround.
The companies that survive see downside clearly.
I watched the aftermath of the 2000 crash. The companies that survived—and even prospered—attacked worst-case scenarios with clear-eyed plans. They acknowledged downside risk and built strategies around it.
Today, many organizations are operating with a “this will pass” mentality. And sure, it will pass. Eventually. But does your company have the cash reserves to wait it out?
If the answer is no, shifting focus to free cash flow isn’t optional. It’s existential.
The takeaway.
The era of cheap, unlimited capital is over. Revenue growth at any cost doesn’t get rewarded anymore. Profitability matters. Cash generation matters. Survival matters.
If you’re still operating like it’s 2020, you’re burning runway faster than you realize. The next capital raise—if it comes—will be brutal.
Get to positive FCF. Or get comfortable with massive dilution and loss of control.
The choice is yours, but the clock is ticking.
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Why Mastery Is Expensive But Competency Scales
Easy to do, hard to master.
I saw this phrase describing a SaaS platform. Simple. Layered. It stuck with me.
So I started applying it elsewhere—skills, workflows, career planning. It turned into a framework for thinking about where to invest time and what mastery actually costs.
Mastery isn’t the only path.
Social media makes it feel like deep expertise is the only winning formula. 10,000 hours. Become world-class. Own your niche.
And sure—mastery can lead to outsized returns. But there are plenty of paths to success that don’t require becoming the best in the world at something. You just need to be strategic about where you go deep and where you stay broad.
That requires thinking about commitment, risk, natural ability, value, and time. Not every skill is worth mastering. Some are worth knowing well enough to be dangerous. Others are worth automating entirely.
Mastery Is Expensive, Competency Scales
Mastery takes time, focus, and obsessive depth most people don’t have. Competency across a dozen high-value skills lets you diagnose fast, connect dots others miss, and know when to bring in experts.
Depth vs. range.
Genetic disposition plays a role here. Some people have the wiring for mastery—the obsessive focus, the tolerance for repetition, the ability to grind on one thing for years.
Others don’t. They consume breadth. They connect dots across domains. They’re competent in twelve things instead of world-class in two.
Neither is better. But you need to know which you are, because the strategy changes.
The framework.
Here’s how I think about skill development across four quadrants:
1. Easy to Do, Hard to Master
This is where I spend most of my time. CRM systems. Coaching. Consulting frameworks. SaaS platforms. Strategy development. Writing. Project management.
My approach: build a broad base of moderate skills with the ability to go deeper when a specific situation demands it. I’m not trying to be the world’s best Salesforce admin. But I can configure it, troubleshoot it, and know when to call in an expert.
Go-to resource: YouTube tutorials, vendor documentation, pattern recognition from repetition.
2. Easy to Do, Easy to Master
I minimize time here. Most manual, stepwise processes fall into this bucket—data entry, basic formatting, repetitive admin tasks.
My goal: automate or outsource anything in this category. If a process can be scripted, documented, or handed off, it should be. These skills don’t differentiate you. They just consume time.
Go-to resources: Scribe for documentation, Zapier for automation, RPA tools, virtual assistants.
3. Hard to Do, Hard to Master
I don’t claim mastery in anything here. Few can. But I maintain competency in several hard skills I’ve developed over my career—programming, sales, lead generation, financial modeling, design thinking, product development.
These require real commitment. If you start down one of these paths without a solid reason, you’ll burn significant energy for minimal gain. But if you choose wisely, competency in hard skills opens doors and commands higher compensation.
Masters in these areas are rare and expensive. Knowing enough to evaluate their work, brief them effectively, and integrate their output is often more valuable than trying to become one yourself.
Go-to resources: Networking, online communities, mentorship, paid courses with real feedback loops.
4. Hard to Do, Easy to Master
I struggled to populate this quadrant. Accounting, maybe? Skills with high barriers to entry but clear paths to competency once you’re in?
Honestly, I don’t invest here. If something is hard to access but easy to master once you do, it’s probably not a leverage point for me.
My personal thesis.
I aim for competency across the value stack of business transformation—enough depth in hard skills to diagnose opportunities, enough breadth to see connections others miss, and enough humility to know when to bring in masters.
The goal isn’t to be the best at any one thing. It’s to be dangerous enough in the right combination of things that I can rapidly assess what’s broken, what’s possible, and who needs to be in the room to execute.
I need to know what mastery looks like so I can help clients stitch together the right resources for ambitious projects. But I don’t need to be the one delivering that mastery in every domain.
The exercise.
Take fifteen minutes and map your own skills across these quadrants:
- Easy to do, hard to master — Where are you building broad competency?
- Easy to do, easy to master — What are you automating or outsourcing?
- Hard to do, hard to master — Where are you committing real energy? Is it worth it?
- Hard to do, easy to master — Does this quadrant even exist for you?
Then ask yourself:
- What’s your commitment level to each category?
- What’s your natural wiring—depth or range?
- What does your skill development thesis look like over the next three years?
This should be unique to you. Don’t copy someone else’s path because it worked for them. Figure out where you have leverage, where you have interest, and where the intersection of those two things creates value.
The takeaway.
Mastery is expensive. It takes time, focus, and often a specific genetic disposition for obsessive depth.
But competency is scalable. You can be competent in a dozen high-value skills and still have time to build a business, stay curious, and avoid burnout.
The trick is knowing which skills are worth going deep on, which are worth staying broad on, and which are worth ignoring entirely.
Most people never ask the question. They just accumulate skills randomly and wonder why nothing compounds.
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Why Brand Power is the Ultimate Cheat Code
The one skill corporate refugees never develop.
Persistence. Not grit. Not hustle. Not “never give up” motivational poster nonsense.
Real persistence—the ability to hear “no” 47 times, reset your brain, and send message 48 without spiraling into existential doubt about whether you’re annoying people or if your entire business model is broken.
I spent fifteen years inside corporate behemoths before going solo. I thought I knew how business development worked. I was humbled fast.
Brand Power Is a Multiplier
Inside corporate, the logo does half the work before you say a word. Strip away the brand, and you’re left grinding on pitch, process, and the ability to keep moving after rejection 47.
Brand power is a cheat code.
Large enterprises have multiplicative advantages you don’t see until they’re gone. The biggest: brand power.
Here’s the test. If Linkology Labs cold messages you on LinkedIn, what’s your response rate? For most people, the bar is high. The content has to resonate. The problem needs to be urgent. The hook better be sharp. The positioning flawless. The timing perfect. And even if you nail all of that, the probability of a response is still low.
Now imagine someone from Apple reaches out. Same message. Same offer. Maybe worse writing.
You respond. Of course you respond. You’re flattered. The brand carries weight. The logo does half the work before you read a single word.
That’s the gap. And when you leave the corporate world, you fall into it hard.
The math changes when you’re nobody.
Here’s how I think about business development success:
BD Success = (Brand Power × Relationships) × (Pitch + Process + Persistence)
Let me break down the variables:
Pitch — Do you solve an urgent problem? Is your offer credible? Does it land in one sentence, or does it require three paragraphs of setup?
Process — Your messaging, hooks, lead math, tech stack, prospect lists, target personas, channels, personalization. The mechanics of outreach done at scale without feeling like spam.
Persistence — The ability to keep moving after rejection. To send follow-up number six without catastrophizing. To treat “no response” as neutral data instead of personal failure. To have a bias toward action over rumination.
Brand Power — Do people recognize you? How does your name make them feel? Do they trust you before you’ve said a word?
Relationships — Do you have history with the recipient? Warm intros beat cold outreach every time. Relationships counterbalance weak brand power.
What the equation reveals.
When I was corporate, I could engage prospects without perfect pitch, process, or persistence. The brand did the heavy lifting. My follow-up could be lazy. My messaging didn’t need to be razor-sharp. People responded because the logo mattered.
Strip away the brand, and the math flips. Now pitch, process, and persistence carry the entire load. You can’t coast. Every message needs to work harder. Every follow-up needs to add value. And you have to keep going when your inbox is silent and your brain is screaming that you’re bothering people.
Persistence isn’t a personality trait.
The good news: persistence is learnable. It’s not some innate quality you either have or don’t. It’s a muscle you build by ignoring the unhelpful voices in your head—the ones worried about being annoying, the ones catastrophizing silence, the ones convinced everyone thinks you’re a pest.
It requires effort. It requires emotional regulation. But it’s not unattainable.
The bad news: it’s uncomfortable. You will send messages that get ignored. You will follow up with people who ghost you. You will feel like you’re bothering strangers. That discomfort is the price of building without a brand.
Lean on relationships while building your brand.
One mistake I made early: I didn’t leverage my relationships. I thought cold outreach was “real” business development. That asking for intros was somehow cheating or imposing.
It’s not. Cold lead generation is a grind. Warm intros close faster, convert better, and feel less soul-crushing. If you have relationships, use them. Let people vouch for you while your brand is still being built.
Your network is the closest thing you have to brand power when you’re starting out. Don’t waste it trying to prove you can do it the hard way.
The inverse is also true.
If you’re backed by a strong brand AND you develop the 3Ps (pitch, process, persistence), you’ll crush your numbers. That’s the multiplier effect in action.
Most corporate reps don’t realize how much the brand is carrying them until they leave. The ones who figure it out—who learn persistence, refine their process, and sharpen their pitch while still inside—become revenue machines when they go independent.
A note to executives.
If you’re a leader who dismisses upper-funnel brand investment as “fluffy” or “hard to measure,” get over it.
Your revenue team is grinding against the math every day. Brand power makes their job exponentially easier. It reduces friction. It opens doors. It turns cold outreach into warm conversations.
Your BDRs will thank you. Your close rates will improve. And maybe, just maybe, your best people won’t burn out and leave because they’re tired of being ignored.
The takeaway.
Persistence is the skill nobody teaches you in corporate. You don’t need it there—the brand does the work.
But when you leave, it’s the difference between building a business and burning out in six months wondering why nobody responds to your emails.
Learn to keep going. Ignore the voices. Send message 48.
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How Legacy Infrastructure Kills New Ventures
Why your growth initiatives keep dying.
Most enterprises carve out capital for new ventures. They target high-growth markets that complement the core business. They staff up with smart people. They launch with fanfare.
Then the initiative dies quietly eighteen months later.
You can blame culture. You can blame execution. You can blame market fit. But there’s a deeper pattern: business model coupling. Companies try to run new business models on legacy infrastructure. Round peg, square hole. It doesn’t work.
Legacy Becomes the Liability
Most enterprises believe their infrastructure is an asset for new ventures. In reality, legacy systems create friction, bloated costs, and customer experiences that tank NPS before you hit year two.
The Widget CO problem.
Here’s the pattern. You’re a global construction widget company. Fifty years building market dominance. World-class at manufacturing, distribution, channel partnerships, and service. Strong margins. But growth has flatlined, and the CEO wants “innovation.”
A sharp team builds a cloud-based software stack. Game-changing product. The MVP crushes in early trials. So leadership launches it through the existing channel—leveraging fifty years of distribution muscle.
A year later, software revenue is 10% of plan. Leadership wants to kill it.
What happened?
You tried to sell SaaS like you sell widgets.
Widget CO is phenomenal at moving hard goods. They’ve optimized heavy tech stacks like SAP. Trained partners to maximize widget market share. Built supply chains that work at scale.
But SaaS is a different business model. Different economics. Different playbook. Different customer expectations.
Widget CO doesn’t know this playbook, so they customize a hybrid Frankenstein solution. The result: terrible customer experience, bloated costs, and unit economics that make no sense compared to benchmarked SaaS businesses.
The legacy becomes the liability.
Widget CO believes they’ll win because they have infrastructure, brand equity, and distribution. And sure—some of those assets help. But most create friction.
The legacy infrastructure was built to support channel partners, not sell directly to end users. Channel partners don’t know how to sell SaaS—they’re widget people. There are no implementation partners. Minimal tech support for customers. The service org can’t answer basic software questions.
NPS craters. The new product threatens the brand. Finger-pointing starts. Before long, the initiative gets shelved.
Fast forward three years: an external startup with an inferior product becomes a unicorn solving the same problem.
How to actually win at this.
Companies that approach new business models with humility can avoid this outcome. Here’s how Widget CO should’ve played it:
1. Use the actual playbook.
SaaS has well-defined business models. Don’t reinvent the wheel. Build from the ground up using proven SaaS economics—CAC, LTV, churn benchmarks, pricing models that work. Use frameworks like the Business Model Canvas to map it out before you build anything.
Don’t retrofit your legacy model and call it innovation.
2. Extract to survive.
New ventures need protection from the mothership. They can’t operate under the same KPIs, approval chains, and quarterly pressures as mature business units.
Create an internal or external venture structure with autonomy. Let them iterate and fail like a startup. Compensate for risk-taking, not for playing it safe. The good news: this can all be virtual. You don’t need a Silicon Valley office.
3. Build a modern tech stack.
Cloud platforms let you stitch together best-in-class capabilities with fewer resources. But don’t force new ventures to use legacy tech stacks designed for mature business models.
Your SAP instance is not the answer. Give new teams autonomy to build lean, proven stacks that match their business model.
4. Cherry-pick the good stuff.
Some legacy assets actually help. Brand recognition. Existing relationships. Distribution muscle—if used correctly.
Figure out which assets create value for the new model. Then structure internal systems to create win-win behaviors. Sales and channel partners can be useful if they’re designed into the business model with the right expectations and training.
Don’t assume everything transfers. Most of it doesn’t.
5. Study what actually worked.
Dig into the ventures that succeeded. What forces enabled those outcomes? What did leadership do differently? What constraints were lifted?
Repeat the elements that worked. Kill the rest.
6. Organize by business model, not business unit.
Some enterprises benefit from organizing around business models instead of traditional structures. Industrial products, retail, ecommerce, SaaS, services—each operates with different economics and different playbooks.
Forcing them under one P&L with shared KPIs creates misalignment and politics.
The takeaway.
Corporate ventures fail for many reasons. But business model incompatibility is the root cause nobody talks about.
Taking time upfront to research the business model and its requirements will save you eighteen months of expensive theater. You’ll either build something that works, or you’ll kill it early before burning capital and credibility.
Stop trying to force new business models into old infrastructure. It’s expensive, demoralizing, and predictable.
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Stop Incrementalizing Yourself to Death
Most people run from chaos. That’s a problem.
There’s a soft skill nobody talks about in transformation work: the ability to sit in disorder without panicking. It’s terrifying. It feels reckless. But it’s one of the fastest ways to cut through years of incremental bullshit.
Take the Twitter saga—whatever you think of Elon, there’s a method worth examining. He laid off half the workforce in one swing. Brutal? Absolutely. Chaotic? By design.
But here’s what happened: the system broke in specific places. Fast. He learned in weeks what would’ve taken consultants eighteen months and millions in discovery fees to figure out. Which 100 roles actually mattered. Which systems were load-bearing. Which processes were theater.
You can hate the approach. But you can’t ignore the speed.
Disorder Uncovers What Matters
Most organizations study problems until the market moves. Controlled chaos cuts through years of planning by spiking the system and watching what actually breaks.
Chaos as a diagnostic tool.
Most organizations incrementalize themselves to death. They pilot programs. They form committees. They study the problem until the market moves and the problem changes.
Controlled chaos does something different—it creates variance fast. You spike the system, watch what breaks, and identify the vital few variables that actually move outcomes. The critical Xs that drive your most important Ys.
In transformation work, we do this deliberately. We dump everything into one space—a war room, a virtual whiteboard, whatever. All the diagnostics, all the analyses, all the conflicting data. It looks like a disaster. Clients panic.
That’s the point.
Ambiguity is a feature, not a bug.
We coach teams to work the chaos. Test hypotheses. Find connections nobody saw when everything was siloed. Build consensus around what success actually looks like—not what the strategic plan from 2019 says it should look like.
Slowly, patterns emerge. The puzzle assembles itself. A strategic path becomes visible that nobody could’ve planned from a conference room.
This is a form of productive suffering. Grinding through disorder hardens the outcomes. The strategy that survives chaos is antifragile—it gets stronger under pressure because it was forged under pressure.
When chaos doesn’t work.
If your business runs well and has solid foundations, don’t inject chaos. Incremental planning works fine when systems are healthy.
But if you’re dysfunctional? If you’re in rapid change and legacy processes are anchors? If every meeting ends with “let’s form a working group to explore this further”?
You don’t need more structure. You need controlled demolition.
The takeaway.
Get comfortable being uncomfortable. Chaos reveals truth faster than consensus ever will. The answers are already in your organization—they’re just buried under process, politics, and the fear of breaking things.
Sometimes you have to break things to find out what matters.
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From 20 Years Experience, 10 Lessons on Financial Forecasting
What twenty years of financial modeling taught me.
Early on, I built credibility through complexity. Multi-tab spreadsheets with hundreds of inputs, sensitivity analyses following statistical distributions, thousands of outputs, and forecasts stretching twenty years out.
I could command a boardroom with the stories these models told. I believed the numbers.
Then I checked the receipts. Short-term? Decent. Long-term? Garbage. Accuracy varied wildly by industry maturity, but the pattern held: complexity didn’t equal precision.
80/20 Rule
Also known as pareto’s principle: roughly 80% of effects come from 20% of causes. Find the vital few, ignore the trivial many.
A decade later, I stripped it all down.
Fewer inputs. Fewer assumptions. Leaned hard into the 80/20 rule—find the variables that actually move the business, ignore the rest.
The 80/20 principle comes from Vilfredo Pareto, an Italian economist who noticed that 80% of Italy’s land belonged to 20% of the population. The pattern showed up everywhere he looked. Today we call it the Pareto Principle: roughly 80% of effects come from 20% of causes. In financial modeling, that means most of your forecast accuracy comes from a handful of key drivers. Nail those, and the rest is noise.
The simpler models weren’t perfect. But they performed better. And teams could actually use them without a decoder ring.
The lesson: less is more. Here are ten things I wish I’d known earlier.
- Understand the goals of the model. Whether revenue, cash flow, market share, P&L, headcount, or volume, design a simple model focused on the core output. And resist the tendency to build the all-in-one model.
- Think modularly, for example, inputs, calculation engine, and outputs.
- Resist complex embedded formulas at first. Further, make it easy for others to edit and understand the logic.
- Use writing as an analogy to modeling. Work quickly to write a first draft, or MVM, a minimal viable model. And then begin an editing process until you create a structured and logical result.
- Subtractive is better than additive. Sculptors start with a block and chisel away until they execute their vision. I attempt to do the same. Start with knowns and chisel away based on confident subtractions. The additive approach, or bottoms-up, can provide a nice check and balance but tends to overshoot reality.
- Start with a shorter duration with realistic assumptions, then expand. Working backward from a target is valuable, but it often leads to disconnected results — so do both. Working the model from the goal also helps to assess input sensitivity.
- Show your results as scenarios; base case, moderate, and aggressive. Don’t fall in love with a single number or scenario.
- Focus on the inputs rather than argue about the outcomes — make it easy for reviewers to challenge inputs and see the results in real time.
- As confidence builds around the model, add new modules or consolidate formulas to reduce the size. Redo the editing step.
- Start from scratch with your models, or at the very least, start with other’s models that you trust and wholly understand.
Modeling anything takes a bit of art and science and most importantly – reps.
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