Bundling and Unbundling: The Only Two Tricks You Need (And You're Still Doing Both Wrong)

A friend bought a small calendar-and-invoicing tool built for personal trainers. Stable revenue, low churn, the kind of clean little business that looks sensible on a spreadsheet. He paid a fair price and went in expecting to optimise the product.

Two weeks later he realised he'd bought the wrong thing. Not a bad asset – the wrong understanding of it. His customers didn't care about the calendar. They didn't care about invoicing. They cared about getting paid on time without chasing clients who'd gone quiet. The software was just the nearest available handle on a problem that was really about cash flow and awkward conversations.

That gap – between what you think you bought and what the customer is actually paying you to solve – is where most acquisitions quietly stall. And it's the gap that the two oldest moves in business are supposed to close.

Jim Barksdale gave us the line. During Netscape's 1995 pre-IPO roadshow, asked how the company would survive if Microsoft bundled a browser into Windows, he reportedly shrugged and said there are only two ways to make money in business: bundling and unbundling (Harvard Business Review). It gets repeated like a spell you can mutter over a Stripe dashboard. It isn't one. Most people who hear it sprint toward the laziest reading of both moves and end up manufacturing work instead of revenue.

The two ways everyone gets it wrong

Unbundling, done badly, means building a smaller version of something big. You look at a sprawling platform, decide you'll take one slice of it, and launch a thinner copy with fewer features and no distribution. You've not unbundled anything. You've just started a worse business in a category the incumbent already owns.

Bundling, done badly, means gluing three unrelated things together and calling it a suite. You acquire a tool, bolt on two more because they were cheap, and present the result as "an all-in-one platform." Customers don't experience it as one thing. They experience it as three logins, three onboarding flows, and a vague sense that nobody is responsible for the outcome.

Both failures share a root cause. They treat bundling and unbundling as moves you make on products. They're moves you make on jobs.

What broad platforms can't do

The reason a small operator can win at all is that big platforms have a structural weakness hiding inside their main strength.

Platforms bundle everything. That's the pitch: infinite choice, every category, learn anything. It feels generous, and for the customer it often is – right up to the point where they need a result. Because when everything is included, no single part of the platform is accountable for getting you to the outcome you actually wanted.

Online learning is the clearest example. Udemy carries well over 250,000 courses. That breadth is genuinely useful if you know exactly what you're after. It's useless the moment you finish "Start Freelancing in 7 Days" and discover that day eight – find actual clients, charge real money, survive the first awkward invoice – isn't in the catalogue. The platform sold you the lesson. It was never going to deliver the job.

That space, between learning a thing and getting paid for the thing, is where a focused business lives. Not by competing with the platform on breadth. By owning the outcome the platform structurally cannot guarantee.

Unbundling is finishing the job, not shrinking the menu

Proper unbundling takes a broad promise and delivers it end to end for one specific person.

So the promise stops being "learn copywriting" and becomes "land your first three paying clients." It stops being "project management software" and becomes "ship client work without things falling through the cracks." Those are outcomes, with a beginning and an end, not topics you could study forever.

This is where acquisitions get interesting, because an asset that looks too small to bother with in isolation often becomes valuable the moment you plug it into a pathway that completes a job. A niche template library is a curiosity on its own. The same library, positioned as step two of a four-step route from "confused" to "paid," is suddenly load-bearing.

That's the grown-up version of portfolio thinking. You're not collecting assets because they're cheap and the dashboard looks impressive with more logos on it. You're assembling a system that moves a particular customer from where they are to where they want to be.

Bundling is the boring glue that makes the outcome inevitable

Once you've unbundled to a clear outcome, bundling becomes the tool that makes that outcome more likely to happen.

You bundle the things that close the gap between buying and succeeding. Templates so nobody starts from a blank page. A bit of accountability so people actually finish. Enough support that a real human appears when someone is stuck. Proof, in the form of examples, that the result is real. None of this is glamorous. All of it raises the odds that the customer gets what they paid for and stays.

The same logic applies to software, not just courses. A small analytics tool plus a weekly "here's what to do about these numbers" email is worth more than the tool alone, because the tool measures and the email acts. A niche CRM plus done-for-you onboarding outperforms the same CRM left on the shelf. You're not adding features. You're removing the reasons a customer would fail.

This is why Cal Newport's argument for doing fewer things, obsessing over quality, and working at a natural pace lands so hard for small operators (Cal Newport, Slow Productivity). Your edge over a platform was never speed or scale. It's care. You can finish the job for one kind of customer better than a company serving everyone ever could.

A worked example, with the messy bits left in

Take the personal trainer tool from the start. Say it was doing around $2,400 in monthly recurring revenue, roughly 300 trainers paying about $8 a month for calendar and invoicing. A tidy buy in the low five figures.

The lazy plan: raise the price, add a feature or two, hope for the best. The buy-and-grow plan starts somewhere else – with the actual job, which was getting paid without chasing clients.

So the first change wasn't to the product at all. It was the addition of automated payment reminders and a simple "your client owes you" chase sequence – the unglamorous bundle that the trainers were doing by hand, badly, when they remembered. The second change was repositioning the whole thing away from "scheduling software" and towards "get paid on time," which is what trainers would actually search for at 9pm after a no-show.

What moved: churn eased, because the product now did the thing people stayed for, and the price went from $8 to $14 a month without revolt, because "get paid reliably" justifies more than "store appointments." Across a year that's the difference between a $29k business and a $50k one on the same customer base, before a single new sign-up. What didn't move on schedule: a planned upsell into nutrition-plan templates flopped, because that was a different job for a different mood, and bolting it on was just bundling-done-badly creeping back in. The lesson held – additions only earn their place if they close the same gap.

Numbers like these are illustrative, not a case study from Indiemaker's own data. The point is the sequence: understand the job, unbundle to the outcome, bundle the parts that make the outcome stick, and leave price until last.

A filter to run before you buy

When you're looking at a micro business to acquire, four questions sort the assets worth owning from the ones that just look cheap.

First, what job is the customer hiring this to do? If you can't say it in one plain sentence, you're buying vibes, not a business.

Second, is that job only half-done today? If users still need three other tools, a community, and a fair amount of luck to get the result, that's not a flaw – that's your unbundling opportunity sitting in the open.

Third, can you improve the pathway rather than just the product? The leverage is usually in onboarding, packaging, pricing, and distribution, not in the feature list. A product change is hard and slow. A pathway change is often a weekend and a repositioning.

Fourth, does this become more valuable beside something else you own? Some assets are unremarkable alone and strategic together, especially when they serve the same customer and the same outcome. That's not empire fantasy. It's just refusing to evaluate an asset in isolation when it'll never live in isolation.

Clear these four and the asset has earned the deeper proportionate due diligence a real purchase needs.

The contrarian bit: stop bundling features, start bundling guarantees

Here's the move almost nobody makes. The strongest thing you can bundle isn't a feature. It's a promise about the result.

"Get your invoices paid within 30 days or we'll chase them for you" is worth more than any number of dashboard tweaks, because it shifts the risk off the customer and onto the operator who actually understands the job. It changes your pricing, because you can charge for an outcome rather than access. It changes your marketing, because you're now making a claim a platform would never dare make across a quarter of a million products. And it changes who you attract – people who want the result, not people collecting tools.

A guarantee forces you to genuinely own the outcome. That's uncomfortable, which is exactly why it works. The discomfort is the moat.

Why this matters more after the consolidation

The platforms are merging. In December 2025 Coursera agreed to combine with Udemy in an all-stock deal valuing the pair at around $2.5 billion; the combination completed in May 2026 (Coursera investor relations). The bundle is getting bigger.

The instinct is to read that as bad news for small operators. It's the opposite. Every time a platform widens its catalogue, the distance between "I have access to everything" and "I got the specific result I needed" gets longer. Bigger bundles create more orphaned outcomes – more jobs that the platform technically covers and structurally can't finish. That's more ground for a focused operator to own, not less.

This is also where the buy-and-grow stance earns its keep. If your plan is to acquire something and flip it in six months, none of this helps you, because closing a job properly takes longer than a flip horizon allows. Cosmetic changes and aggressive price hikes can juice a metric for a quarter. They can't build the thing a buyer-and-grower is after: retention, trust, and a product that quietly does what it promised. Oliver Burkeman's point about productivity applies to acquisitions too – you don't hack your way to a durable business, you choose what matters and accept the trade-offs (Financial Times interview).

Indiemaker exists for the people running the slower play – buyers who acquire a real asset and grow it, rather than treating ownership as a six-month gamble with better spreadsheets. Bundling and unbundling are the two levers that reward exactly that play. They pay out for operators who understand a customer well enough to finish a job, and they punish everyone hoping to glue features together and run.

Barksdale was right that there are only two moves. He just left out the part that matters: both of them are about the customer's outcome, and neither of them is about your product. Once you see that, the question stops being "what should I buy?" and becomes "whose job can I finish that nobody else will?"