Author: Paul Austin-Menear

In Conversation with Nate Littlewood
Scaling Profitably: Insights from Nate Littlewood, Founder of Future Ready CFO
In the latest episode of The Journey: In Conversation, Paul Austin-Menear sits down with Nate Littlewood, the visionary founder of Future Ready CFO. Nate shares his journey from engineering to finance and how he now empowers e-commerce and CPG founders to scale their businesses profitably.
Nate’s approach is rooted in strategic finance, focusing on high-impact projects through ROI analysis, bottleneck identification, and aligning skills with business needs. He emphasizes the importance of distilling a long list of potential projects into just two or three high-priority initiatives, using frameworks like OKRs (Objectives and Key Results) to drive accountability and progress.
One of the standout moments in the conversation is Nate’s reflection on his previous venture—an urban gardening startup aimed at influencing food choices and sustainability. He candidly discusses both the successes and challenges of that endeavor, offering valuable lessons for aspiring entrepreneurs.
For founders looking to grow their businesses, Nate’s insights are a goldmine. He highlights the difference between strategic finance and operational finance, stressing that a holistic view of the business can solve many seemingly isolated problems. Whether you’re a startup founder or a seasoned entrepreneur, this episode is packed with actionable advice to help you scale profitably.
Key Takeaways:
- The power of ROI analysis in prioritizing projects.
- How bottleneck identification can unlock growth.
- The role of strategic finance in solving siloed business challenges.
Read the full post or listen to the podcast edition here: https://6catalysts.substack.com/p/in-conversation-with-nate-littlewood
April 9, 2026
The Journey : In Conversation with Janna Landry
In this episode of The Journey: In Conversation, I sat down with Janna Landry — founder of Align, communications coach, and co-host of the Pull the Shoot podcast — to unpack what truly makes someone compelling when they speak.
Janna’s origin story starts in a world most business leaders never experience: performance. She grew up on stage and in recording studios, learning how professional performers create immediate emotional engagement. But the big idea she brought into her adult career is simple: those “showbiz secrets” aren’t exclusive to entertainment. They translate directly into business.
We get into the core of her coaching approach, starting with a question most people skip: what kind of communicator are you? Janna frames three broad styles — visual communicators, “feely”/kinesthetic communicators, and analytical communicators — and argues you shouldn’t fight your wiring. The goal isn’t to manufacture a persona. It’s to lean into what’s already true about how you naturally connect.
From there, the conversation moves into audience fit and credibility. Janna’s point is blunt: if you’re operating in a role you don’t actually want (or don’t believe in), people will feel it. Humans have a finely tuned detector for inauthenticity, and it shows up through pacing, tone, and tension — even when the words are “right.”
We also talk about why humour and imperfection build trust faster than polish. She argues that audiences don’t want perfection; they want a real human. Small, relatable stories — family dynamics, food mishaps, pets, everyday life — give listeners permission to relax, lower their guard, and actually absorb the message.
One of the most tactical segments is her “beginning, middle, end” structure: earn trust first, deliver the organized “guts and glory” in the middle, then land the “button” — the memorable closing that brings the audience back to the person behind the message. We even connect this to classic keynote moments like Steve Jobs’ “one more thing.”
Finally, Janna shares grounded advice for solopreneurs and coaches: keep learning, volunteer and build relationships through contribution, join professional communities, and remember that navigating change and failure starts with stepping back and reframing the situation from 30,000 feet.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-janna-landry
March 12, 2026
The Journey : In Conversation with Jeff Sesol
In this episode of The Journey: In Conversation, Paul Austin-Menear sits down with Jeff Cecil, Founder and CEO of Pull the Shoot, for a wide-ranging discussion on leadership, entrepreneurship, and what it really takes to build organizations that last.
Jeff’s story begins in the early days of enterprise technology. After leaving college early and teaching himself to program, he helped automate banking operations in Chicago before launching one of the internet’s earliest large-scale cloud storage platforms—years before the term “cloud” existed. That venture, FreeDrive, reached tens of millions of users worldwide in the late 1990s, pushing the limits of bandwidth, storage costs, and infrastructure long before hyperscalers or autoscaling were even concepts.
But the heart of this conversation isn’t nostalgia—it’s reflection. Jeff shares what it means to be early, sometimes too early, and why first-mover advantage often comes with hidden costs. He and Paul explore the realities of scaling technology in uncharted territory, the brutal economics of infrastructure in the dot-com era, and the humility that comes from realizing timing matters just as much as vision.
From there, the conversation shifts into Jeff’s second act: leadership development. After decades of consulting, Jeff recognized that operational efficiency alone doesn’t grow companies—people do. Pull the Shoot was born from that realization, inspired by Jeff’s experience skydiving: when everything is moving too fast, leaders need to “pull the chute,” slow down, regain perspective, and work on the business instead of being trapped in it.
Together, Paul and Jeff dig into modern leadership challenges: managing across four generations, the myth that great individual contributors automatically make great managers, and why so many new leaders fail due to lack of training and support. They discuss why appreciation matters more than compensation for retention, how over-control suffocates teams, and why real leadership is about helping others surpass you.
The episode closes with practical stories from Jeff’s coaching work—real examples of emotional reactions derailing leaders, and how clarity, calm communication, and self-awareness can unlock growth. It’s a grounded, experience-driven look at leadership as a human discipline, not a title.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-jeff-sesol
February 5, 2026
The Journey : In Conversation with Anita Bruinsma

How Anita Bruinsma Built Clarity Personal Finance
And Why Advice-Only Planning Matters More Than Ever
This episode of The Journey: In Conversation digs into money, motivation, and the real human stories behind personal finance. Paul sits down with Anita Bruinsma, founder of Clarity Personal Finance, to explore how a 25-year banking career evolved into a fee-only financial planning practice designed to empower people—not sell products.
Anita’s path is anything but accidental. She talks through her early days at TD Bank, where sitting across from everyday clients helped her recognize a gap: people weren’t getting the financial literacy they needed to make confident decisions. Even basic ideas—cash flow management, mortgage decisions, saving structures, or the difference between an RRSP and TFSA—weren’t well understood. And the consequences weren’t abstract: lack of clarity trapped people in unhappy situations, stalled life decisions, and created emotional stress that compounded financial stress.
That insight eventually pushed her toward entrepreneurship. But the shift wasn’t glamorous. Anita shares candidly how leaving the stability of a corporate salary, benefits, and structure challenged her sense of identity and security. The motivation? A desire for autonomy, the example of her self-employed partner, and the realization that flexibility mattered—for her life, for her kids, and for the kind of work she wanted to do.
A major theme in the conversation is the unique value of advice-only financial planning. Unlike traditional advisory models tied to product sales or assets under management, advice-only planning removes the built-in biases that skew recommendations. Anita lays out the advantages clearly: transparent pricing, conflict-free guidance, and the ability to support DIY investors—a growing demographic of people who want control, low fees, and credible education.
She also highlights a rapidly emerging niche: younger clients in their 20s who skip banks entirely and go straight to online brokerages. Many arrive after dabbling in meme stocks or high-risk investments and realizing they need structure, not hype. Anita’s investment coaching helps them build solid portfolios using simple ETF-based strategies, focus on asset allocation, and avoid the pitfalls of overconfidence or misinformation circulating online.
The conversation goes deeper than tactics. Anita opens up about impostor syndrome, the emotional weight of difficult client conversations, and the discipline required to build structure when you work from home. Her honesty makes the episode valuable not just for anyone curious about personal finance, but for anyone building a business grounded in service, authenticity, and continuous learning.
If you want insight into how real people navigate major career transitions, how financial literacy can fundamentally change lives, and how a niche practice can grow organically through trust and referrals, this episode delivers.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-anita-bruinsma
January 8, 2026
[Medium] Does LinkedIn Hate Substack?
The question sounds dramatic, but creators who publish consistently on LinkedIn eventually run into the same friction point : posts with links seem to perform worse. It’s become almost folk wisdom. Experienced users have internalized the rule. Newer users are taught it. And creators who rely on LinkedIn for distribution quietly accept the reality that every outbound link feels like a tax.
But folk wisdom isn’t data. And platform behaviour doesn’t always match the tidy hypotheses we come up with to explain it. So when a Substack Note from writer JHong pointed out that “link in comments” has become basically invisible — and that including the link in the main post was the only real way to get clicks — it raised a more interesting question. If link placement matters, does link destination matter too?
For someone publishing simultaneously on Substack and a LinkedIn Newsletter, that question isn’t academic. It affects distribution, visibility, strategy, and growth. And it’s a question worth testing instead of speculating.
Why LinkedIn Might Penalize Links in the First Place
To understand any modern feed algorithm, you need to understand how the business behind it makes money. LinkedIn is, above everything else, an advertising platform. Yes, it sells subscriptions. Yes, it offers hiring tools and premium features. But the bulk of its revenue still comes from selling targeted ad impressions. That means one metric matters more than anything else: time spent on-site.
Any link that takes someone away from the feed interrupts the behaviour LinkedIn is optimized to monetize. So if the platform deprioritizes posts with links — especially links to other publishing platforms like Substack — it’s acting rationally within its incentives. A link is a potential leak in the revenue model.
But not all links are equal, which is where the real question emerges. Does LinkedIn treat a link to its own ecosystem (a LinkedIn Newsletter article) differently than a link that directs a user to a completely external platform like Substack?
I designed a two-week experiment to find out.
How the Experiment Worked
For fourteen days, three posts were published each day :
1. A control post with no link at all.
2. A post linking to the LinkedIn-hosted version of an article.
3. A post linking to the Substack-hosted version of the same article.
The posts were kept as similar as possible : same topics, same visual structure, similar tone, and the same posting window each day. The idea wasn’t to measure clicks or conversions, that wasn’t the concern. The only question was : Which posts does LinkedIn show to people?
The metric of interest was impressions — the number of times each post appeared in a user’s feed.
The Results, and Why They’re Interesting
If the intuition behind link penalties is correct, the control posts should perform best. And they did, but the scale of the difference was surprising.
Across the test period :
- Control posts generated 140% more impressions than posts linking to LinkedIn Newsletter articles.
- LinkedIn-linked posts only slightly outperformed Substack-linked posts (493 vs. 436 impressions).
- The gap between the two link types was small enough that it’s hard to claim any real advantage for on-site links.
What surprised me most wasn’t that links depress reach, but that LinkedIn’s own Newsletter feature didn’t receive preferential treatment. If anything, the platform treated both link types similarly, suggesting that the act of clicking itself — on-site or off-site — interrupts the feed enough to trigger lower distribution.
From the platform’s perspective, it makes sense. Even an on-site click disrupts scrolling behaviour, which weakens the core ad-driven engine. The feed is the product. Anything that pulls a user out of that rhythm becomes a liability.
Behavioural Trends Worth Noting
Beyond link performance, the dataset surfaced a few patterns that matter for creators :
- Wednesdays performed best, generating 24% more impressions than any other day.
- Morning posts outperformed afternoon posts by about 17%.
- Posts with two or more reactions tended to accelerate, confirming the widely observed snowball effect of engagement.
None of these patterns should be generalized too aggressively… audiences differ, routines differ, and LinkedIn’s algorithm is dynamic. But the trends are directionally useful and reinforce an important reality : most distribution problems are behavioural, not algorithmic.
What Builders Should Take Away From This
If your primary goal is reach, removing links is the simplest way to improve post visibility. If your goal is traffic, then links are necessary, but you should rely on them strategically rather than by default.
The real value of this experiment isn’t the specific numbers. It’s the reminder that attention platforms optimize for themselves, not for creators. And if you want to build an audience that compounds, you’re better off understanding the underlying incentives than guessing at the shadows cast by the algorithm.
This article is a part of my series on topics for entrepreneurs, intrapreneurs, and people who just love building things. I podcast and post weekly with tools and guides on The Journey. Check out the companion piece here : https://6catalysts.substack.com/p/does-linkedin-hate-substack
December 12, 2025
Rethinking Hiring : A Deep Dive into Human-Centric Job Design
The Journey : In Conversation with Jennifer Houle
The latest episode of The Journey : In Conversation brings a sharp, honest examination of the hiring experience from both sides of the table. Paul sits down with Jennifer Houle (VP of People Operations and author of Uncompliant) to unpack why so many hiring systems continue to fail real humans, and what a better, more human-centred approach could look like in companies of all sizes.
Their conversation opens with a reflection on a two-part Substack collaboration where both explored how hiring workflows are structurally misaligned with the lived experiences of candidates, leaders, and teams. That collaboration sparked this follow-up episode, where Jennifer expands on why she advocates for systems thinking and human-centred design inside HR, a stance she notes wasn’t always safe to vocalize earlier in her career.
The episode explores the emerging shift within the HR profession : away from compliance-driven gatekeeping and toward designing environments where people can learn, grow, and contribute meaningfully. Jennifer points to widespread layoffs, restructures, and a rise in lived experience among HR practitioners as catalysts for a more compassionate, honest approach to both hiring and offboarding.
A major theme in the conversation is siloing inside organizations. As companies scale, teams drift apart, communication erodes, and the resulting inefficiencies ripple through recruiting, onboarding, and performance. Jennifer argues that HR should act as a connector… not a walled-off function. Cross-functional integration, transparent communication loops, and permeable boundaries are critical for preventing teams from accidentally working against each other.
From there, the two dissect a real job posting. They examine mismatched reporting structures, unrealistic expectations, gender-coded language, and the hidden story a job posting tells about a company’s culture. Jennifer highlights how language like “high-performance culture” or “poise under pressure” often signals deeper systemic issues… long hours, unclear expectations, or poorly scoped responsibilities. They explore why accountability should be tied to authority, why analysts shouldn’t be expected to police leadership, and why clarity and honesty matter far more than word count.
The episode closes with actionable advice for candidates : in a hyper-competitive market, you cannot rely on applying through an ATS alone. Stand out by going beyond the default… building personal connections, demonstrating insight into the business, and signalling genuine interest.
This conversation is a thoughtful, grounded critique of hiring norms and a call for organizations to rethink how they design roles, support their people, and communicate expectations. Whether you’re a founder, hiring manager, HR leader, or job seeker, the insights here will help you better understand the ecosystem you’re operating within. And how to navigate it more intentionally.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-jennifer-houle
December 9, 2025
Does LinkedIn Hate Substack?
A Data-Informed Look at Organic Reach and Link Penalties
LinkedIn’s “algorithm penalty” has been a source of debate for years. The idea is simple: platforms built on advertising revenue want users to stay on-site. If a post includes a link that takes people off-site—say, to Substack—the platform has strong incentives to suppress that content’s reach. But does this actually happen? And if so, does link destination matter?
This analysis began with a simple question triggered by another Substack writer’s observation: the old trick of “link in comments” is basically invisible, so if you want clicks, put your link in the main post and accept the penalty. That sparked a deeper question worth testing: do posts linking to my LinkedIn Newsletter perform better than posts linking to my Substack? And how do both compare to posts with no links at all?
Before diving into results, it’s worth revisiting the fundamental mechanics. LinkedIn is powered primarily by advertising revenue. This model depends on one thing above all else: attention. More attention means more impressions they can sell to advertisers. Posts containing external links—by definition—direct attention away from LinkedIn’s domain, reducing their potential ad inventory. Even on-site links, like those pointing to LinkedIn Newsletter posts, may interrupt the infinite scroll pattern advertisers rely on. The logic behind an algorithmic penalty is straightforward.
To test this, a two-week experiment was designed using three types of posts each day:
1. A control post with no link.
2. A promotional post linking to the LinkedIn version of an article.
3. A promotional post linking to the Substack version of the same article.
All posts covered similar topics and followed a standardized formatting and publishing protocol to reduce bias. The experiment focused specifically on impressions—how often each post appeared in users’ feeds.
The results were surprising.
The control group dramatically outperformed both link groups, generating 140% more impressions than posts linking to LinkedIn’s own Newsletter articles. This alone supports the theory that any link—regardless of destination—reduces reach. Meanwhile, posts linking to LinkedIn Newsletter content only marginally outperformed posts linking to Substack (493 vs. 436 impressions). The difference wasn’t large enough to draw strong conclusions in favour of the on-site destination.
This data suggests that LinkedIn’s algorithm penalizes most link-based posts, even when the link keeps the user on LinkedIn’s own ecosystem. The platform appears to prioritize continuous feed scrolling over any click-out behaviour, even if the destination is technically “on-site.”
A few behavioural trends emerged from the dataset as well. Wednesday was the strongest day for impressions, followed by Tuesday, with a 24% gap between first and second place. Morning posts (before noon) generated roughly 17% more impressions than afternoon posts. And posts that managed to gather more than two reactions enjoyed significantly stronger reach, likely because LinkedIn promotes content that sparks visible engagement among mutual connections.
The broader takeaway mirrors long-standing social media patterns :
- Posts without links have an inherent advantage for reach.
- Time of day and day of week matter, but the patterns will depend on your own audience’s habits.
- Engagement begets more impressions; LinkedIn amplifies content when people in your network interact with it.
If you rely on LinkedIn for distribution, the practical implication is clear: links should be used sparingly and strategically. The tradeoff between reach and click-through is unavoidable, but data-informed publishing can help you find the balance that works for your goals.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/does-linkedin-hate-substack
December 2, 2025
The Journey : In Conversation with Reed Hansen

From Niching Down to Building Lead Machines : A Conversation with MarketSurge’s Reed Hansen
If you’ve ever wondered how a boutique marketing agency can punch above its weight, today’s episode of The Journey : In Conversation delivers a practical, field-tested blueprint. I sit down with Reed Hansen, founder and CEO of Market Surge, to unpack lessons from early niching, the messy middle of 2021’s lockdowns, and the evolving reality of SEO in an AI-first world.
Reed’s entrepreneurial spark started early, hauling rocks and pulling weeds on his father’s landscape sites—absorbing the durable truths of small-business grit. After time in tech sales and an MBA, he pivoted into digital agencies, where strategy, planning, and systems thinking fit better than the extroverted cadence of quota life. That mix of experience—plus co-building his wife Liz’s photo studio—laid the groundwork for Market Surge.
Why integrated services matter. Reed makes the case for unifying CRM, ads, SEO, websites, and automation under one strategic roof. When a partner can see the whole system, they can pursue revenue, not just tasks. That’s also how you create real accountability: fewer vendors, clearer goals, deeper impact.
2021: constraints and opportunity. Launching amidst lockdowns wasn’t simple, but Market Surge spotted an underserved niche—boudoir photography studios. By pairing empathetic messaging with simple operational wins (notably SMS workflows for confirmations, contracts, and follow-ups), they helped high-touch studios thrive when customers craved a premium, out-of-home experience. The lesson: in a crisis, clarity plus fast execution can compound.
From volume to value. Early on, the team led with a white-label CRM (built on GoHighLevel) and attracted quick sign-ups—and quick churn. The shift? Fewer clients, larger engagements, and broader ownership of the growth machine. Recurring revenue, strategic advisory, and long-horizon work (like SEO) build stickiness and trust.
SEO in the age of AI. Is AI the SEO killer? Reed argues it’s an evolution. With LLM summaries crowding above-the-fold space and “no-click” answers rising, brands must re-optimise for authority, helpfulness, and answer-ready content (think richer FAQs, expert citations, and technically accessible sites). The durable principles of credibility and usefulness still win—only now they must be legible to humans and machines.
Content as a moat. Market Surge is leaning into a newsletter and podcast to educate, build authority, and reduce dependence on fragile referral loops. The meta-lesson for founders: become the teacher your market needs. Consistency compounds; credibility sticks.
On failure and resilience. Reed shares a tough layoff story that ultimately catalysed his growth. Sales is a “no-heavy” craft; the courage to iterate faster—armed with real feedback—can be the difference between drifting and compounding.
Advice for aspiring agency owners. Start specialised. Find a “one-to-many” partner (coach, community leader, or adjacent influencer) who accelerates trust and shortens sales cycles. You can broaden later—after you’ve earned your beachhead.
We wrap with Market Surge’s positioning: they “build lead machines that work while you sleep.” It’s a crisp promise—and a reminder that marketing tech and content only matter if they move revenue while you’re on a job site or in the studio.
Key themes: integrated services, automation and SMS, AI-era SEO, authority building via content, and the strategic pivot from tool-selling to transformation-owning partnerships.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/in-conversation-with-reed-hansen
November 27, 2025
Hiring for Humans : Building the Team to Take on the World
When founders talk about team-building, the conversation often drifts toward speed… speed to hire, speed to scale, speed to meet the aggressive expectations placed on young companies. But speed is not a strategy. And nowhere is this more evident than in the culture born out of Silicon Valley’s “hire fast, fire fast” doctrine. It’s a mindset optimized for short-term gains, investor appeasement, and breakneck scale… not for building a stable, resilient business that can weather uncertainty.
This article challenges the reflexive adoption of that philosophy and argues for something better : a way of hiring designed for humans, rooted in long-term thinking, focused on creating durable organizations—not precarious ones.
The popularization of “hire fast, fire fast” coincides with the model and incentives of venture capital. Venture money is designed to move quickly and to return capital quickly. When investors expect 5x returns in five years, leaders inevitably feel pressured to staff rapidly, chase momentum, and treat people as expendable components of a larger financial machine. It’s an environment where speed outranks judgment, and founders are encouraged to use headcount like ammunition.
But business-building outside Silicon Valley does not have to be, and often should not be, driven by those same incentives. Most builders are not chasing decacorn status. They are building camels : organizations resilient enough to survive droughts, adaptable enough to face uncertainty, and steady enough to avoid the fragility that comes with hyperspeed growth.
Camel companies recruit differently. They prioritize people who fit the mission, the culture, and the evolving nature of the work. They invest in communication, critical thinking, and adaptability… skills that matter far more over the long run than any single technical competency. They also treat hiring as a systematic, team-driven process rather than a rushed scramble to fill chairs.
Hiring slow demands clarity about the role, transparency with candidates, and a willingness to evaluate soft skills as seriously as hard ones. It also requires leaders to be deeply involved, working in close coordination with HR or advisors, and treating the hiring decision as a strategic one instead of a box-ticking exercise. A rigorous process centred around clear expectations, skill-relevant testing (fairly compensated), and multi-stakeholder evaluation dramatically increases the odds of a good fit.
On the other end of the equation, firing should be a last resort. Not because accountability doesn’t matter, but because people are assets in every way except on the balance sheet. Institutional knowledge, accumulated experience, and the relational fabric employees build over time all contribute to an organization’s real value. Even if accounting standards don’t capture it.
For founders who want to build long-lasting businesses, employee investment is not charity (it’s strategy). And giving workers real skin in the game through mechanisms like employee ownership trusts further aligns incentives and strengthens commitment.
If half of businesses fail within two years, resilience matters more than ever. And resilience comes from people: the right people, chosen with intention, supported with care, and trusted to grow alongside the company.
This is what it means to hire for humans, not headcount. To build for the long game, not the fast exit. To choose the camel over the unicorn.
Read the full post or listen to the podcast edition here : https://6catalysts.substack.com/p/hiring-for-humans-building-the-team
November 25, 2025
[Medium] How to Know When to Open Your Chequebook
Bootstrapping is a badge of honour. It’s the mark of resilience, grit, and a refusal to rely on outside capital to bring your vision to life. But there’s a hidden trap in that mindset : the temptation to hoard resources so tightly that progress slows to a crawl.
Every founder eventually faces the same question : When should I spend money, and when should I just do it myself? It sounds simple, but behind that decision lies a complex web of emotions, economics, and opportunity costs that can define whether your business thrives or just survives.
The Fear Behind the Frugality
When you’re building something from nothing, every dollar feels sacred. Your instinct is to stretch every resource to its breaking point. But fear-based frugality often creates blind spots — it stops you from seeing how much you’re losing by refusing to spend. You may save $1,000 in cash but burn twenty hours of focus that could’ve earned five times as much elsewhere.
This invisible cost… opportunity cost… is the real metric to watch. Money is renewable. Time isn’t.
Thinking Like an Investor
The best way to make smarter spending decisions is to think of your business like an investment portfolio. How you spend your time, money, and attention represents an allocation of decision-making capital. Some investments compound; others deplete. Your goal is to maximize long-term return, not just minimize short-term cost.
The framework outlined here helps you do exactly that. Evaluate each task through seven lenses :
1. Hours (Time) : How long will it take you or your team?
2. Cost (Cash) : What’s the direct expense?
3. Opportunity Cost : What’s the hourly value of your time multiplied by the hours invested?
4. Learning Value : Will this teach you something valuable for the future?
5. Error Risk : How badly could things go wrong if you mess up?
6. Repeat Value : Will this continue delivering value after it’s done?
7. Strategic Leverage : Does this effort compound in future cycles?
With this framework, you can build a habit of making decisions based on outcomes, not emotions.
Buy or DIY?
The rule of thumb :
Buy expertise when the problem is non-core but high leverage, the skill gap is wide, or the risk of failure is costly.
DIY when the problem strengthens your differentiation, offers repeated learning opportunities, or involves low risk and high compounding value.
In practice :
- An insurance agent shouldn’t code their own website.
- A snack food maker shouldn’t design packaging without regulatory expertise.
- A boutique retailer might fulfil orders themselves — until scale makes outsourcing more efficient.
Systems Thinking and Control
Complexity multiplies with growth. As the numbers get bigger, add a systems lens. Ask yourself :
- Is this decision reversible?
- Is the problem recurring?
- Does solving it create an asset (knowledge, process, or IP)?
- Will outsourcing free time for higher-value work?
If the first two answers are “no” and the last two “yes,” buying the solution is probably the wiser move.
But perhaps the biggest challenge isn’t financial, it’s psychological. Many founders mistake control for competence. They equate doing everything with being capable of everything. The truth? Control scales inversely with impact. The more you insist on doing, the less your business can grow.
Learning to Deploy, Not Hoard
Entrepreneurship is a game of energy allocation. Your job isn’t to protect every dollar; it’s to amplify every unit of momentum. Maturing as a builder means knowing when to release control and deploy capital strategically, trusting that the returns will exceed the costs.
So before you reach for your metaphorical chequebook, or clutch it tightly, ask yourself : will this decision create more leverage tomorrow than it costs today?
This article is a part of my series on topics for entrepreneurs, intrapreneurs, and people who just love building things. I podcast and post weekly with tools and guides on The Journey. Check out the companion piece here : https://6catalysts.substack.com/p/how-to-know-when-to-open-your-chequebook
November 14, 2025