My senior thesis was on Stevie Smith, an English poet of the early 20th century who illustrated her poems with odd, wry line drawings. Her best-known poem, “Not Waving but Drowning,” describes a man whose desperate signals the people around him mistake for cheerfulness. Reading Smith taught me to look for the gap between what people present and what they’re actually experiencing. I didn’t expect that to be a business skill.

I arrived at the Stanford University’s Graduate School of Business in 1994 as that poetry student, not knowing how to do a discounted cash flow or really read a balance sheet. I left two years later with a toolkit, a network, and options I could never have built alone. That education led to a career I love, advising companies like Netflix and Microsoft on how to build lasting relationships with their customers. I’m grateful.

So when Cambridge professor Christopher Marquis argued in The New York Times last week that it’s time to shut business schools down, I expected to disagree. Instead, I found myself nodding to much of his argument.

Marquis describes students who arrive with inspiring goals and abandon them within about 14 weeks, swept up by recruiting events, peer pressure, and six-figure tuition debt. I watched that happen to classmates who came to fix health care or education and left for banks and consulting firms. Many are thriving. Few are doing what they came to do. A few are just coming around to that original goal, many years after graduation.

That outcome is what the system is built to produce. Stanford’s motto is “Change lives. Change organizations. Change the world.” But the numbers that drive rankings and applications are starting salaries and placement rates. In Stanford’s most recent employment report, 33 percent of job-seeking graduates went into finance and 11 percent into consulting.

In my work, I help organizations distinguish between a transaction, which ends at the sale, and a relationship, which rests on what I call a Forever Promise of ongoing value. Business schools market a Forever Promise to change the world. Then they measure themselves like transactional businesses, by what happens at graduation.

The Wall Street Journal’s Callum Borchers recently showed where that leads. Chief executives are flocking back to business schools for executive education, a market one research firm projects will grow from $55.1 billion this year to $115.7 billion by 2033. They come for help with AI, but also for ethics, reflection, and something harder to name. Former Harvard Business School dean Nitin Nohria told Borchers that new CEOs in his workshop confess they don’t feel like masters of the universe. Their first assignment is to write their retirement speeches. Many come mostly for camaraderie, because it’s lonely at the top.

As a Stevie Smith reader, I recognize that picture: leaders at the peak of their careers, not waving but drowning.

What those executives are seeking at 55 — ethics, purpose, reflection on legacy, and peers who understand them — is precisely what the MBA crowded out at 27. Business schools now sell back, at a premium, the reflection they didn’t make room for the first time.

The stakes go beyond the C-suite. According to an analysis reported by Poets&Quants this spring, 10 current presidents and prime ministers outside the United States studied business at American institutions. [The president of the United States is a Wharton graduate.] When students learn that every relationship is a negotiation, we shouldn’t be surprised when leaders treat alliances and public institutions as deals to win rather than relationships to sustain.

To be sure, business isn’t a zero-sum game, and defenders of business schools, including London Business School’s Alex Edmans, have rightly pushed back on that caricature. Sixteen percent of Stanford’s most recent class launched their own ventures. Finance and consulting aren’t villainous careers. And executive education is a business school keeping its relationship with graduates alive over decades, which is exactly what I recommend. Abolition is the wrong answer.

The right answer is to move the reflection to the front. Assign the retirement speech in week one, before recruiting season starts the 14-week clock. Track what graduates do at 10 and 20 years, not just their starting salaries. Treat alumni as lifelong members, with support for career changes back toward the goals they arrived with. And make room for the poets. History, ethics, and literature teach that people aren’t counterparties.

Stevie Smith drew her doodles alongside her poems because the words alone didn’t tell the whole story. Starting salaries don’t either. I’m calling on my alma mater and its peers to measure whether their graduates change the world — and to start asking the question while there’s still time to answer it differently.

Business School Should Assign the Retirement Speech in Week One was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

I spend my days helping companies build lasting relationships with customers. In that work, I have learned that community is one of the strongest forces for retention. People stay with products that connect them to other people.

So when a team shows me a connected appliance, I ask one question: does this product bring people together, or does it stop at the router? The answer determines whether the app becomes a reason to stay or a reason to leave.

Connected products and social products

A connected product talks to its owner. It starts the brew from bed, tracks how many cups you made this week, and updates its own firmware. The value flows to one person, and the data flows to the company.

A social product goes further. It lets owners talk to each other, under the brand umbrella, and it produces something worth passing along. Its value grows with each new owner, because each owner adds to what the others can use.

Many connected appliances reach the first stage and then add a feed with likes and comments. A feed gives people a place to post. The reason to post has to come from the product itself.

The artifact test

The simplest test I know is the artifact test. Ask what an owner makes with the product that another owner would want.

In coffee, the answer is the recipe. A great cup comes from dose, grind, water temperature and, on an espresso machine, a curve of pressure and flow over about thirty seconds. Enthusiasts trade these recipes on forums and YouTube today. Most of them copy settings by hand from a screenshot.

Decent Espresso shows what happens when the product makes that trade effortless. Its machines record each shot as data. Owners upload shots to a site called Visualizer, compare them with shots from other owners, and download another owner’s profile to brew on their own machine. One owner’s discovery becomes every owner’s starting point.

Traeger, the pellet-grill maker, shows a second model. Its app offers more than 1,000 recipes from chefs, pitmasters and the company’s culinary team, and owners can send a recipe to a connected grill. The brand calls its owners the Traegerhood. In this model, sharing flows from a cast of experts to the owners. A broadcast model is easier to control and faster to launch. A peer network is slower to start and harder for a competitor to copy.

A launch team should decide which model it is building and design the artifact to fit. If there is no artifact worth sharing, people aren’t going to share it. So this is both a “marketing” issue and a “product feature” issue.

Build for the Super Users

Decent did not build Visualizer. According to the site’s own history, an owner created the first version within hours of unboxing a new machine in November 2020 and shared it with other owners. The platform later moved to a freemium subscription and now serves coffee enthusiasts beyond Decent.

I call these people Super Users. They are the small share of customers who tinker, teach and recruit. In my experience, they create most of the value that everyone else consumes. Coffee has a large population of them. It’s actually a good category for community.

A product earns Super Users by giving them room to work: open profiles, data they can export, and credit when others use what they made. A product loses them by locking its data inside an app they cannot extend.

Launch teams should also respect where coffee people gather today. They already meet on Reddit, YouTube, Discord and long-running enthusiast forums. A brand that builds a walled community inside its app asks people to leave those places. A brand that makes its artifacts easy to share in those places joins a conversation that is underway.

Keep the Forever Promise

A social product carries a risk that a toaster never does. When people build a habit and a set of shared recipes around a device, they expect the device and its app to keep working. I call this the Forever Promise: the commitment a company makes to deliver value for as long as the customer stays.

Anova, the sous vide brand, tested that promise in public. In August 2024, the company announced a fee of $2 a month or $10 a year for new users of an app it had offered free since 2014. It also said that its original Bluetooth and Wi-Fi cookers would lose app connectivity in September 2025. The backlash was loud, and the company later reversed course on the older devices. Some owners in its own community forum said the reversal came too late to restore their trust.

The lesson is about sequence. A company can charge for an app, and many should. The price has to arrive with new value, and it has to be part of the promise from the first day. A fee added after people have bought the hardware feels like a toll on something they already paid for. TBT the BMW heated seats debacle of 2022.

Four questions before launch

I ask every team building a connected product to answer four questions before it ships.

1. What is the forever promise that justifies the app? What are customers trying to achieve, and how completely are you able to ensure success with the app?
2. How important is the app — is it required, as with Peloton, or a nice-to-have, like many printers?
3. Is this app relationship between the consumer and the brand, or does it include connection across consumers in a community? What is most important?
4. What will you promise owners about price and support for the life of the device? Write it down and publish it before the first unit ships.

Community can be an excellent sticky retention and expansion tool, but for community to gather around a product, that product has to be really important, and sharing of content needs to provide measurable value that members care about.

Your Coffee Maker Has Wi-Fi. Does It Have Friends? was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

With The Odyssey and Spider-Man helping pull people back into theaters this summer, I have been thinking again about what went wrong at MoviePass.

I love movies: the popcorn, the trailers, the dark room, the shared laugh or gasp. So I understand the appeal of MoviePass.

Its Forever Promise was strong:

Pay one monthly fee and go to the movies without worrying about the ticket price.

That is a real customer insight. MoviePass was not just selling cheaper tickets. It was removing friction.

Instead of asking, “Is this movie worth $18?” the customer could ask, “What should I see this week?”

That is what good subscriptions do.

Netflix changed home entertainment from “Should I rent this?” to “What should I watch?”

Spotify changed music from “Should I buy this album?” to “What do I want to hear?”

Disney+ turned a family content library into a recurring household utility. Blue Apron tried to turn dinner planning into a repeatable habit.

The problem was the model underneath it.

MoviePass collected fixed monthly revenue. But every time a subscriber went to a movie, MoviePass had to pay the theater for the ticket. That meant each act of engagement created a real variable cost.

So the most enthusiastic customers were also the most expensive customers.

At MoviePass, more usage created more losses.

Compare that with Netflix. Netflix has huge content costs, but it does not pay a full retail fee every time a subscriber watches another episode.

Or Disney+. A child watching Frozen for the 43rd time may help retention, reinforce brand affinity, and support the broader Disney ecosystem.

MoviePass sat in the middle. It owned the subscription relationship but not enough of the economics.

The 2017 $9.95 unlimited plan made the problem sharper. It was simple. It drove growth. It created buzz. All good elements for a healthy subscription.

But it also required too many assumptions that weren’t proven:

1. Light users had to subsidize heavy users.
2. Usage had to decline over time.
3. Ticket costs had to stay manageable.
4. Theaters or studios had to share economics.
5. Advertising, data, or other revenue had to subsidize the model, eventually. And most importantly…
6. Growth had to improve the model rather than expose it.

Those assumptions can be tested. They cannot be wished into existence.

This is where MoviePass moves from a subscription case study into a fraud and governance case study.

A bad model is not fraud. An aggressive price cut is not fraud. A growth strategy is not fraud.

But when management knows the economics are not working and tells investors or customers a better story than the facts support, the issue changes.

That is why I also think about Amazon Prime’s “Project Iliad.”

Amazon Prime is a far stronger subscription business than MoviePass. The value proposition is broad: shipping, video, music, deals, storage, and habit. But the FTC alleged Amazon used dark patterns to enroll customers into Prime and made cancellation harder through a process internally known as “Iliad.” Amazon later settled the FTC case.

That is a different problem from MoviePass, but it’s relevant.

MoviePass shows what happens when the economics of the promise don’t work.

Project Iliad made it too hard for customers to leave when consumers felt the economics no longer worked.

Both violate the spirit of a Forever Transaction.

A subscription should not depend on subscribers failing to use the product or failing to cancel.

For subscription practitioners, the MoviePass lesson is not “be less bold.”

They neglected first to ensure the promise, pricing architecture, customer behavior, and cost to serve fit together. And then they hid the problems and inserted friction into the product to make it harder for subscribers to get the value they’d already paid for.

MoviePass had a promise people wanted. But they failed to deliver on it in a way that was fair to subscribers and investors alike.

MoviePass: What Happens When the Forever Promise Breaks was originally published in The Startup on Medium, where people are continuing the conversation by highlighting and responding to this story.

On July 29, the Federal Trade Commission, joined by Utah and California, sued the telehealth company, hims & hers. The complaint alleges the company did the following:

1. Charged consumers almost immediately after they submitted an online intake form, often without the medical consultation it advertised,
2. Made canceling a subscription deliberately difficult, and
3. Shared consumers’ sensitive health information, including specific medical conditions, with Meta, Snap, and other advertising platforms.

Hims and Hers disputes the claims and says it will fight them vigorously. Whatever the case’s outcome, the complaint describes something familiar to anyone who studies subscription business models: fast sign-up, hard exit, data monetized on the way out. It’s the standard “bad actors” playbook. It’s just never before been run on people’s health information at this scale.

Hims & Hers isn’t an outlier. Amazon bought One Medical in 2023 for roughly $3.9 billion — not a hospital system or an insurer, but a membership, an app, and same-day access. CVS Health has spent more than $18 billion on Oak Street Health, part of CVS Health and Signify Health to build its own primary-care and in-home-care networks. Concierge and direct-primary-care practices, charging patients $100 to $200 a month for a doctor who isn’t rationing 15-minute slots, are among the fastest-growing models in American medicine.

I’ve spent my career helping companies build what I call the Forever Transaction: A relationship where the customer keeps renewing because the company keeps delivering on a Forever Promise, not because fine print or friction locks them in. Netflix and Amazon Prime won that way.

Healthcare is now running the same playbook. Done well, it works: a member who can text her doctor and get a same-day video visit is more likely to catch a problem early and stay engaged. Direct primary care in particular has real promise as a lower-cost alternative, and continuity of care is a genuine clinical good. The problem the FTC noted is when healthcare adopts the habits of the Membership Economy’s worst actors, rather than the best. And the stakes here are way higher than a forgotten gym membership or streaming service.

To be sure, one lawsuit against one company doesn’t indict a category. Teladoc, the largest player in the category, trimmed its 2026 revenue forecast the same week, citing pressure on its BetterHelp mental-health subscription business — a sign the strain isn’t confined to one company’s legal troubles. But this summer, HCA Healthcare disclosed that the expiration of enhanced Affordable Care Act subsidies cost it roughly $400 million in the second quarter alone, as patients who lost their exchange coverage went uninsured instead of finding new plans. Roughly 2.6 million people have dropped off ACA plans since last year, and hospital executives say almost none of them landed anywhere else. Subscription medicine isn’t an alternative for those patients; it requires disposable income most of them no longer have. But as public coverage keeps fraying, subscription and concierge care will increasingly be the only reliable access to a doctor that anyone has, insured or not, just at the moment its own leading players are being accused of the industry’s worst subscription habits.

That combination is why healthcare subscriptions can’t be regulated like a lifestyle app anymore.

Four changes are overdue:

1. Apply the billing, cancellation, and data-privacy standards the FTC just used against Hims & Hers across the whole subscription-health category as a baseline, not case by case after each lawsuit.
2. Require plain-language disclosure, so patients know exactly what a membership fee buys versus what insurance already covers before they sign up.
3. Enforce consistent licensure and scope-of-practice as telehealth crosses state lines at scale.
4. Tie the growth of concierge and membership networks to investment in the safety-net capacity they draw from — residency funding, Medicaid-facing primary care, loan forgiveness — given that the Association of American Medical Colleges projects a shortage of up to 124,000 physicians by 2034, including as many as 48,000 in primary care, the exact specialty concierge medicine pulls hardest from, and the exact specialty a growing uninsured population will need most.

A subscription only earns the right to renew if it keeps its promise to the member every single day. Healthcare is now testing whether that promise can survive contact with a system where the member’s well-being and the public’s access to care are diverging fast.

The membership economy is coming for your doctor’s office. Whether it becomes the best thing to happen to American primary care in a generation, or a nicer waiting room for the people who can still afford one, depends on the guardrails we build now. Let’s not wait for the next lawsuit or the next earnings call.

The Membership Economy’s Next Frontier Is Your Doctor’s Office was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

I have been talking to a lot of young adults looking for internships and first jobs. The only way to get a job is by networking. Sorry, but that’s the truth for 99% of new-to-work folks.

It’s just too easy to push a button on LinkedIn and submit 100 applications in an hour. Unless your resume is a perfect match, you won’t get a second look.

Your Network Is a “Forever Transaction”

Here’s the thing. Networking is best done when you don’t need something. Build a strong, vibrant network in advance, and it’s there when you do need it — to move to a new city, start a company, or land your next job. Think of your network as a “forever transaction”. It’s a commitment between you and your people you respect to support each other when you can.

The data backs this up. Researchers studying entrepreneurs found that 78% of entrepreneurs say networking is vital to their startup’s success. People who relocate and rebuild a social network show measurably lower cardiovascular stress than those who stay isolated. And employees hired through a personal connection stay roughly 70% longer than those hired off a job board. Networking isn’t a soft skill. It’s infrastructure.

There’s a difference between building a network and using it, though the two often happen at once. (“I need a job, so I guess I better start building my network!”) That’s backwards. The network should already be there when the need shows up.

Start With the Network You Already Have

To build and strengthen your network (something all of us should do continuously) start by mapping who’s in it today, one slice of your life at a time. Hometown friends and their parents. The people at the coffee shop where you worked in high school. College friends, faculty, staff. People from internships and past jobs. People from extracurriculars. Most of us have more network than we think. We’ve just never taken inventory.

Start with your friendlies — the people you’re most comfortable with. “Hey, do you know anyone in Austin in the startup world who’d talk with me? I’m thinking of moving there to start a company.” Friendlies aren’t always best-positioned to help. They’re just the most likely to try.

As you get clearer on what you need, move to looser ties: people you know less well, friends of friends, the edges of your network. You can be more buttoned-up with them, more focused on what you’re trying to learn or accomplish.

Mark Granovetter’s landmark study on job changers found that most people landed their new role through a contact they saw only occasionally or rarely — not their closest ties. A 2022 MIT study of 20 million LinkedIn users confirmed it at scale: the strongest connections were the least useful for finding a new job. Your best source for something new is likely someone with maybe ten mutual connections, close enough to trust you, distant enough to hand you information your inner circle doesn’t have.

Then Expand to Weaker Connections

If your circle of friends, colleagues, and classmates is small, expand it by targeting people who share something with you — anything that makes them likely to take your call.

I recently advised a young man who’d been a firefighter and was now in law school part-time while working. Good grades, not great. Big firms saw a second-tier school and passed. So I pointed him toward lawyers at his target firms who’d come up through public service, the military, or union work — people wired to recognize what his path actually said about him. That’s how you build relationships with strangers: find the point of resonance first.

My own son was a D1 athlete. When he was job hunting, he sought out people at target companies in his target city who’d also played college sports and asked for informational interviews. They understood exactly what that level of commitment costs. They talked to him. They helped.

Especially early in your career, don’t hold back because you’re not sure what you bring to the table.

First: helping a hardworking, talented person is its own reward. That’s implicitly what you’re offering. Just don’t forget to circle back to everyone who’s helped you — keep them posted, not just when you need something again.

Second: you’ll often find ways to help that have nothing to do with careers. Setting up an AI agent. Introducing someone to a pet sitter. Reciprocity rarely runs through the same channel it came in on.

If the balance ever feels off, find someone to mentor. There’s always someone a step behind you who needs a leg up. You can be that person.

A complete network has three legs: mentors and referral sources above you, peers beside you who compare notes, and people below you whom you mentor.

You need all of them. So start building today, before you need it.

Build Your Network Before You Need It was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

“What retention rate proves that we have product-market fit?”

It is one of the most common questions I hear from subscription leaders-and one of the hardest to answer responsibly.

The honest answer is: it depends.

A subscription with a unique business-related ROI could reasonably retain customers in the 90% range. Customers are likely to stay

Netflix, as a discretionary entertainment source, has more competition. Switching costs are low, substitutes are plentiful and retention may be considerably lower-even when customers genuinely like the product.

But that does not mean benchmarks are useless.

Just be thoughtful.

Two Kinds of Benchmarks

The first kind helps you run the business.

These are often internal benchmarks:

For example, people who sign up for budgeting software as a New Year’s resolution might cancel more quickly than people who sign up randomly.

These metrics often provide early warning signals that something isn’t going well or deeper reasons why some features or messages work better than others. They are more granular, too.

Other metrics, often lagging ones, explain the business to outsiders.

Leadership teams, boards, and investors need a manageable set of indicators they can use to evaluate progress. The strategic question becomes:

What metrics do we want important stakeholders to use when judging whether this subscription is getting stronger?

You need internal and external metrics.

Product-Market Fit Is a System, Not a Metric

For a subscription business, I look for evidence across four categories.

1. Engagement and value

Are customers experiencing the value they expected?

Important measures include:

• Activation at a meaningful milestone
• Time to meaningful value
• Recency and frequency of use
• Depth and breadth of engagement

The activation milestone should represent customer value-not simply completion of an onboarding step.

Opening an app is an activity. Completing the first workout, publishing the first project, or using a feature that solves the customer’s problem may be activation.

2. Retention

Do customers continue choosing the product?

Track:

• Customer retention
• Revenue retention
• Renewal by plan
• Cohort retention curves

Retention by acquisition channel and customer segment

Averages can conceal more than they reveal. A business can show acceptable overall retention while newer cohorts deteriorate-or while one acquisition channel brings in customers who leave almost immediately.

3. Commitment

Are customers demonstrating that the subscription deserves an ongoing place in their lives?

Signals include:

• Organic and referral-driven acquisition
• Annual plan selection
• Expansion into higher tiers or additional users
• Willingness to accept a price increase
• Advocacy and recommendations

These behaviors matter because they demonstrate more than satisfaction. They show trust in the Forever Promise: the customer believes the company will continue delivering value into the future.

4. Unit economics

Can the company acquire and serve subscribers economically?

Track:

• Customer acquisition cost
• Customer lifetime value
• CAC payback
• Gross margin
• Contribution margin by cohort

An LTV-to-CAC ratio of approximately 3:1 is often treated as a healthy benchmark. But it is not a goal in isolation.

A company that becomes overly protective of the ratio may underinvest in growth. Sometimes a lower short-term ratio is rational if the company has a credible opportunity to acquire valuable customers at scale.

Unit economics should create decision-making discipline-not become an excuse for timidity.

The Numbers That Would Get My Attention

Thanks for reading this far. Here are some benchmarks that would indicate the directional health of a new subscription. They would make me look more closely at a consumer or creator subscription. But a lot would depend on the business and industry-not just these numbers in a vacuum. Please don’t quote me on these without a caveat!

Some of these targets are ambitious.

Substack says paid publications commonly convert approximately 5–10% of free subscribers, with 10% as a goal. RevenueCat’s app-subscription research shows that trial conversion varies substantially by trial length and category, with longer trials producing median conversion rates above 40% in its 2026 data.

Annual commitment is also particularly revealing. Patreon reports that annual members retain at approximately twice the rate of monthly members. RevenueCat similarly finds that annual subscribers are considerably more likely than monthly subscribers to remain active over a full year.

But context still matters.

A 25% annual-plan adoption rate might be highly impressive for a new creator asking an audience to trust an unproven promise. It might be disappointing for a tax-compliance tool that customers expect to use continuously.

A 40% trial conversion rate might signal excellent value realization. It might also result from offering trials only to a small, highly qualified population.

The number is the beginning of the analysis-not the end.

A Note About Involuntary Churn

Not every lost subscriber actively decided to leave.

Payments fail because cards expire, accounts change, banks decline transactions or billing systems fail to recover the payment. Recurly’s benchmark research attributes roughly 1.4% in monthly churn to involuntary causes across its dataset.

That may appear small, but its cumulative impact is material-and unlike dissatisfaction-driven churn, much of it may be recoverable.

Subscription leaders should separately track:

• Voluntary cancellation
• Payment failure
• Recovery rate
• Retry effectiveness
• Card-update success
• Subscriber reactivation

A company that combines voluntary and involuntary churn into a single number loses the ability to diagnose the underlying problem.

Look at What Strong Subscription Companies Choose to Reveal

No public company shares its complete product-market-fit dashboard. But the metrics companies choose to disclose tell you how they want the market to understand their model.

Costco keeps the story remarkably simple: membership growth, renewal, and willingness to pay. The company’s periodic fee increases provide a powerful test of whether members believe the value significantly exceeds the price.

Duolingo reports monthly active users, daily active users, paid subscribers, and revenue. It also increasingly connects specific product experiences to engagement and learning outcomes. The message is clear: habit drives value, and value drives conversion.

Netflix helped establish engagement and retention as core subscription concepts, although it now reveals less subscriber detail than it once did.

For B2B and multiperson subscriptions, HubSpot, Atlassian, and Zoom provide useful examples of tracking revenue retention and expansion across an organization.

These companies are not necessarily giving outsiders every metric that matters. They are selecting a few metrics that reinforce the strategic story they want investors to believe.

Every subscription business should do the same.

Build a Dashboard But Look Past It Too

A high-level dashboard might include the following:

1. Activation and time to value
2. Engagement with the core behavior
3. Cohort retention
4. Annual plan adoption
5. Organic and referral-driven acquisition
6. Unit economics

But you can’t improve every metric simultaneously.

There may be a season of focus on usage, when the priority is helping customers establish habits.

There may be a season of focus on organic growth, when the priority is creating advocacy and referrals.

There may be a season of focus on involuntary churn, when the fastest path to growth is simply recovering customers who never intended to leave.

The goal is not to collect the greatest possible number of metrics. It’s to identify the behaviors that demonstrate customers are receiving ongoing value-and then build the organization around strengthening those behaviors.

Stop Asking for the “Right” Subscription Retention Rate was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

In the subscription economy, we love the idea of “forever”-recurring revenue, loyal customers, and predictable growth. But here’s the truth most businesses learn the hard way: not every customer is meant for forever. And that’s not a failure. It’s strategy.

In The Forever Transaction, the goal isn’t to keep every customer indefinitely. The goal is to build a forever transaction with the right customers-the ones who truly value what you offer, engage consistently, and trust you enough to stop considering alternatives.

A forever transaction is built on an ongoing promise: you continue to deliver value, and in return, your customers continue to stay.

But that kind of relationship only works when there’s real alignment from the start.

Why Some Customers Should Leave

Many organizations struggle because they try to hold onto customers who were never a good fit.

Some come in with expectations that do not match what the business actually provides. They ask for features or experiences that fall outside your core value, and in trying to accommodate them, companies risk diluting what made them valuable in the first place.

Customers are great at expressing their pain points, but it is your role to design the right solution, not endlessly customizing around every request.

Other customers behave transactionally in what is supposed to be a long-term relationship. They join for a single benefit, consume quickly, and leave just as fast. T his kind of churn is not always a retention issue. It is often a targeting issue. These customers were never meant for a forever relationship, and trying to force one can lead to frustration on both sides.

Perhaps most importantly, the wrong customers can pull your focus away from the right ones.

Your best customers, the ones who stay, engage, refer others, and derive real value, are the foundation of a successful subscription business. They are the ones you want to replicate and prioritize. When too much attention is given to edge cases or misaligned users, you risk neglecting the very people who would have stayed with you for the long term

The Power of “Pruning”

One of the most important and often overlooked strategies in subscription businesses is the willingness to “ prune.” This means letting go of customers who do not align, saying no to segments that are not a fit, and designing your offering with a clear understanding of who you serve best.

Pruning is not about shrinking your business. It is about strengthening it. When you try to be everything to everyone, you end up weakening your value for the people who matter most.

Because if you try to serve everyone… You end up serving no one well.

Forever Starts with the Right “Who”

The strongest subscription businesses do not start with pricing or features. They start with clarity about their ideal customer.

They understand who benefits most from their offering and build every part of the experience around that person. This is the essence of the Membership Economy, shifting from transactions to relationships, from short-term acquisition to long-term retention, and from volume to customer lifetime value.

What This Means for Your Business

If you are building or scaling a subscription model, it is worth taking a step back and asking some hard questions.

Are you trying to hold onto customers who were never a good fit?

Are you designing for your best customers, or simply reacting to the loudest ones?

Are you optimizing for sign-ups, or for long-term success?

The answers to these questions will shape not just your growth, but the sustainability of your business.

Final Thought

“Forever” is not about holding on tighter. It is about aligning better. When you attract the right customers, deliver meaningful and ongoing value, and stay focused on their success, that is when forever becomes possible. Everything else is just noise.

Your Business — On AutoPilot with DDImedia AI Assistant
(Join Our Waitlist)

Visit us at DataDrivenInvestor.com

Join our creator ecosystem here.

DDI Official Telegram Channel: https://t.me/+tafUp6ecEys4YjQ1

Follow us on LinkedIn, Twitter, YouTube, and Facebook.

Not Every Customer Is Meant for Forever was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

I love networking.

For me, it’s about building meaningful relationships with people I trust and admire. I know not everyone feels the same. For some, it’s more transactional and about getting something as quickly as possible from someone else. That’s why I developed my course on Strategic B2B Networking for Driving Sales.

My goal with this course is to help people develop networking habits that build real relationships, that are useful without being ick. If you are working on establishing new relationships yourself, make sure you reach out to people that you don’t necessarily see every day.

Ideally, you’ll want to have 7 kinds of people in your professional network.

I am always looking for practical tips for both “overzealous” and “reluctant” networkers. If you have any suggestions, please let me know!

The 7 Kinds of People You Want in Your Network

1/ (Current and former) Customers

These are people that have already bought from you. You should be strengthening these relationships, even when they’re inactive, because they may soon be in a situation to buy from you again, or serve as a source of referrals, or as a reference.

2/ Prospects

There are likely many people who “could” someday be a customer, but aren’t today. Get to know them, so when they’re ready to buy, you’ll be top of the list and front of mind.

3/ Mentors

Mentors are people you can learn from. Seek out people who are ahead of you in their career, or who have expertise you seek to develop, and build a connection.

4/ Peers

Remember how important it was in high school to have study buddies in every class — someone who shared notes, helped you out when things got tough and kept you laughing? You still need people like that — these are people at about your level, in similar roles to yours, both inside and outside your organization. You can bounce ideas off them, ask them questions too mundane for mentors and compare notes.

5/ Referral sources (upstream)

Some people will never be in a position to hire you, but know lots of prospective clients and have good relationships with them. Often they are upstream — meaning a customer buys from them before they would buy from you. For example, if you’re a decorator, it might be helpful to have architects and realtors as referral sources.

6/ Support sources (downstream)

You will look better if you can anticipate future needs of your client and have the connections to help them. Decorators need to be able to recommend painters, carpet installers and handymen.

7/ Mentees

It’s more than good karma that justifies finding people coming up in their careers behind you. Mentees force you to explain your logic and how you do things, which often helps you clarify your own strategy. You might be surprised by what you learn from them, since they are establishing their approach in a different time. And finally, people you mentor might be good hires one day.

And remember: Loose-ties are the key to a strong network.

Go beyond your close colleagues and invest in maintaining relationships with more casual contacts. If you focus your relationships too narrowly, you’ll end up with a group of people who all have the same connections.

By building ties across a broader community, you increase your reach, your sources for information, and ultimately, your personal brand.

Building Relationships That Last was originally published in The Startup on Medium, where people are continuing the conversation by highlighting and responding to this story.

The answer is, of course, it depends.

1. Start with the Business Model: Why Offer “Free” at All?

Before deciding what’s free or paid, ask yourself: What role do free subscribers play?

If your business depends on viral marketing: Your free tier is a marketing engine. It attracts, delights, and expands your reach. That means your free experience should be good enough to make users want to share it.

Think of Canva or Notion. Both offer generous free features that help users create and collaborate. Every shared design or document becomes an organic ad for the product.

If your business depends on network effects: Your free subscribers add value for your paying users simply by participating. In this case, investing in a strong free experience is part of your product development strategy.

LinkedIn is a classic example. The platform only works because free users make it valuable for recruiters, job seekers, and advertisers.

2. Have You Already Given It Away for Free?

Many companies launch with generous free offerings, intending to “monetize later.” That can work especially in early growth or “land grab” phases, but it also sets a powerful precedent.

Before moving anything to paid, ask:

• Did we set user expectations early on?

If the answer is yes, think very carefully.

Charging for something previously free can feel like betrayal. When you change the deal, you risk not only churn but reputational damage.

3. Are You Already Making Money from Free Users?

If you’re already earning revenue from free users through ads, data, or aggregated insights, consider whether it’s ethical to also charge them.

If you monetize free users indirectly such as ads, data, insights, and marketplace fees, then charging them again can feel like double taxation.

Today’s consumers are more aware than ever. They know when they’re the product. If they realize that, they may expect more value for free or even compensation for their participation.

This isn’t just a pricing issue. It’s a trust issue. Transparency about how you use data and participation builds credibility and loyalty.

4. What is Your “Forever Promise”?

Your forever promise defines what users can count on from you as your product evolves.

You might have:

• One promise for free users (for example, “You’ll always have access to your notes even if you stop paying”)
• Another for paid users (for example, “You’ll get collaboration, analytics, and premium support”)

You can have different promises for different tiers, but each must be clear, consistent, and predictable.

The key is clarity. When expectations are clear, trust grows. When they aren’t, churn follows.

Here’s a quick framework:

Be clear on your “forever promise”. You might have a different promise for your free subscribers than your paying ones, or the same one but to different degrees. In either case, you need to be clear to your members about what they can expect from you. Forever.

4 Questions to Help You Decide What Should Be Free vs Paid in Your Freemium Model was originally published in DataDrivenInvestor on Medium, where people are continuing the conversation by highlighting and responding to this story.

But once you’re there, how do you make sure your product stays on those shelves and that customers can actually find it and keep coming back to it?

Building relationships through an intermediary is hard. And when a retailer sits between you and your customer, you’re sharing your margins and losing the direct connection that helps you grow.

That’s why many food makers look for ways to sell direct through a tasting room, their website, or a direct-to-consumer subscription.

And when you go direct, everything changes.

You keep the whole margin, keep prices down, and most importantly, you learn about your customers.

Where they are.

What they like.

How often they return.

And you can use that information to develop subscriptions that deepen the relationship over time.

Meanwhile, customers love these models too — because with a subscription, they never run out, they get access to new and hard-to-find flavors, and they feel closer to the vendors they discovered on vacation or through research.

And this is important because this ongoing access is the heart of the “forever promise” in food subscriptions: a steady, reliable, curated connection to the specialty flavors people love most.

Food and beverage is simply one of the clearest examples of this dynamic.

Food and beverage brands like Bokksu , Wildgrain , Universal Yums , and Tinned Fish Club have leaned into this advantage.

There are many nostalgia-oriented food subscriptions that have failed. The difference with successful models is that they go beyond sentiment.

They’re not meal kits. They’re not solving dinner. They’re offering access to products that aren’t easily available in supermarkets, curated selections by experts, and the convenience of having specialty items delivered directly to your door.

People want curated, hard-to-find selections that they would never discover on their own. They want time savings, trustworthy curation, and a little bit of delight delivered to their doorstep.

But it’s not enough to simply ship a box.

1. Surprise-and-Delight Boxes

In this model, the food or beverage provider chooses the items, and discovery is the goal. But this model is risky because most consumers tire of it after a few shipments. They join to discover something new, then find the flavors they love, and eventually want to purchase those flavors directly — not more surprises. If someone finds the perfect energy bar with the right macros and flavors, why would they want random ones delivered?

2. Memberships (Costco, Amazon Prime style)

Memberships involve customers paying for access or benefits: discounts, free shipping, exclusive gifts, and invitations to special events. This model is good because it basically asks the customer to “raise their hand” and indicate their intention to be frequent shoppers. Unlike points programs where everyone joins but only a few earn benefits, with a premium loyalty membership, the customer pays up front.

3. Subscribe-and-Save

The benefits here are simple: never run out, never run to the store, and save money. This is the model I recommend starting with — possibly with samples added then layering in a true membership over time. The surprise-and-delight model? Maybe never. It’s too hard to manage fairly and tends to drive cancellations faster.

I recommend starting with subscribe and save (potentially throwing in samples with the shipment), then experimenting with a true membership, and potentially never do the “surprise and delight” because that model is so hard to manage (if you join in March and get the best-selling strawberry jam and I join in September, do I get the less popular apple butter as my first shipment?) and because people cancel quicker.

With regard to other features, I’d pay attention to the benefit they came for, and focus on that. And across every model, one factor is consistently overlooked: onboarding to build engagement and retention — in the moments after someone signs up, when their enthusiasm is high, how do you reinforce the wisdom of their decision and build good habits?

Innovative Food Subscription Model to Look Out For

Organic farm subscriptions like ButcherBox, Matilda’s Flowers, and Produce Box — they tap into an ongoing need (not sure flowers qualify, but for me, they are always on my front hall table).

They support local farmers. They build community. They deliver on a forever promise that leads to a forever transaction — tie of the month clubs just aren’t “forever”!

Examples

Matilda’s Flowers

Local, grower-supportive, educational, and community-centered. You don’t just receive flowers; you learn about the growers and how to arrange them.

Produce Box

North Carolina-based, women-run, neighborhood moms doing the deliveries. It’s a brilliant model that taps into the power of community-one of the strongest forces in the Membership Economy.

Final Thought

The most resilient food subscriptions aren’t built on novelty or nostalgia. They’re built on habit, trust, and ongoing value.

If you’re designing a subscription for specialty food, start by asking a simple question: What ongoing need am I helping my customer get done that is better, easier, or more meaningful than any alternative?

Answer that well, and you’re no longer selling a box. You’re building a forever promise.

Specialty Foods and Subscriptions — a Perfect Match was originally published in The Startup on Medium, where people are continuing the conversation by highlighting and responding to this story.