Category Archives: Entrepreneurship

The Odd Little Book All Founders Should Read On Selling Their Company

I recently read The Magic Box Paradigm by Ezra Roizen. It’s self-published, was first released in 2016 [1] , and you won’t find it on most startup reading lists. The writing is uneven and inconsistent. The metaphors are weird. There are too many TLAs (three-letter acronyms). Nevertheless, I think all founders should read it — early and often. Early, meaning years before you contemplate selling your company; often, because if you read it early, you’ll need a periodic refresh.

Everyone in M&A has heard the expression “great companies are bought, not sold.” It gets knowing nods in board meetings, but is then promptly ignored in practice. The reason it’s hard to internalize isn’t that the idea is obscure — it’s that acting on it requires you to behave in ways that feel completely wrong. It requires you to slow down, stay deliberately vague, and resist the urge to pitch. For a founder who has spent years getting good at pitching, that turns out to be genuinely difficult to do. Knowing something and behaving consistently with it are two different things. [2]

The Magic Box

Roizen’s central metaphor is the “magic box.” Some things are popsicles — they have known, comparable value, and you can auction them with reasonable confidence in the outcome. Startups are not popsicles. They’re magic boxes. A startup’s value isn’t fixed or objectively discoverable; it depends almost entirely on who’s opening the box and what they plan to build once they have it. The same company can be worth $50M to one acquirer and $500M to another — not because of negotiating leverage, but because of genuine strategic fit. Which means the job isn’t to run a wide process and let the market discover your price. It’s to find the buyer for whom your value is highest and help them see it — ideally before you ever hire a banker.

The Trail of Tears

The best part of the book is the start of Chapter 6, describing what Roizen calls the sad path. I call it the Trail of Tears, because founders walk it constantly — and the thing that makes it a tragicomedy is that every single step feels reasonable at the time.

These two pages are worth the price of the book alone (highlighting mine).

Tragicomedy.

For those who can’t read the images, it goes like this. One of startup Alpha’s investors happens to meet GiantCo’s head of corporate development at a conference. Corpdev thinks Alpha might be worth a look. The investor, delighted to add value, makes an introduction. Value added! [3]

The next day Alpha’s CEO gets an email from Corpdev asking for a deck he can socialize with the relevant product teams. The CEO panics slightly — what do I send? — and settles on his most recent investor presentation. It worked great for raising a big round. It’s got product detail, market sizing, competitive positioning, go-to-market strategy. Should do just fine.

Corpdev reviews the deck. He sees some potential but no clarity on where Alpha’s products might fit into GiantCo’s portfolio. He forwards it to a few product leads and a general manager. The deck is salesy. It was designed to solicit investment in Alpha as a standalone company. The deck’s salesy quality is read by GiantCo as a sign that Alpha is trying to sell itself.

A presentation is scheduled. The relevant GM — probably the best potential internal champion — can’t make it. The demo goes well. GiantCo’s attendees are engaged. The meeting ends with enthusiasm and a commitment to follow up.

Corpdev follows up by sending Alpha’s CEO a list of boilerplate diligence questions: financials, cap table, customer concentration, licensing. The kind of get-to-know-ya questions that corporate development types like. Roizen’s line here is worth remembering: Corpdev is using an X-ray when a telescope is what’s needed. Alpha’s CEO, under pressure from his investor for updates, has his finance team pull together a packet in response. Everything is proceeding mechnically at this point.

Corpdev now takes a critical look. Revenue is concentrated. Burn is high. Valuation expectations are probably rich given the cap table. Alpha is too early and GiantCo is too busy. The eventual reply: we really like what you’re doing, but it doesn’t map to any current priorities. Let’s stay in touch and try to connect again at next year’s conference. In short, you’re a nice guy/gal, but let’s be friends.

The investor wants an update. The CEO has to explain that nothing happened.

The wrong deck. The wrong follow-up. The right GM missing from the meeting. An X-ray instead of a telescope. No chance for the idea to form inside GiantCo. And now the bad news needs to be broken to an investor who was just trying to help.

It’s a sad path indeed. And the reason it works so well as a teaching device is that the CEO didn’t do anything stupid. They made reasonable calls at every step. That’s the point.

This literally happens every day. It wastes time. It’s demotivates founders, raising and then dashing expectations. Worse yet, its leaves the company with a residual “those guys are for sale” taint — a mark that’s hard to see and even harder to erase. [4]

The Partner Big Idea

What should have happened instead? Roizen’s answer is what he calls the Partner Big Idea (PBI). The mechanics of building a PBI are more involved than I’ll go into here — read the book — but the core principle is this: the deal has to become their idea, not yours.

The investor presentation was the original sin. It accidentally signaled that Alpha was for sale, which put GiantCo in evaluation mode rather than strategy-building mode. What Alpha needed wasn’t a buyer to evaluate it. It needed a champion within GiantCo — ideally that GM who missed the meeting — to develop a strategic vision that Alpha was necessary to execute. Not “Alpha is an interesting acquisition target” but “here’s a thing that we need that we can’t build without Alpha.”

Building that requires a totally different set of behaviors. It means getting to the right person quickly — the GM or product leader whose roadmap would actually change — and not spending lots of time with Corpdev. It means asking more questions than you answer. It means leaving the story incomplete enough that the other side has room to build it with you. Incompleteness, in this context, is a feature. It gives the champion something to build and own. [5]

Corpdev is not that person. Corpdev manages process and filters opportunities. They can help once a deal is real, but they rarely create the reason for the deal to happen. If your primary relationships are with Corpdev, you’re operating inside a system designed to evaluate, not to originate. And it’s a system that, left to its own devices, will evaluate your company on a financial, not a strategic, basis.

An Investment Banker Weighs In

I asked an investment banker friend, who works regularly with top strategic buyers, about the book and its relevance today. He had three key observations.

First, the importance of partnerships as a precursor to M&A has only grown since the book was written. Companies partner, integrate products, share customers. Over time, the relationship gets embedded in each side’s roadmap. At that point the “big idea” isn’t hypothetical — the buyer doesn’t just believe in the opportunity, they depend on it. The magic box becomes a dependency.

Second, geography matters to some more than the book acknowledges. Snowflake, for example, drew a reasonably hard line for a long time: a deal couldn’t happen unless the technical team relocated to one of their engineering hubs. With return-to-office (RTO) continuing to gain momementum, I think this will continue to increase in importance.

Third, don’t underestimate the importance of team buy-in. Strategic acquirers aren’t just buying code, they’re buying the team that builds it and they can tell the difference between teams are cashing out (and who will work until exactly the day their handcuffs disappear) and teams who are genuinely excited about a combined future. As a reflection of this, buyers are increasingly splitting the payment, sending more money to the retention pool and less money to the cap table. This creates a tension between investors and employees, but it all gets negotiated in the process.

But What About Banker-led Processes?

At this point, you might reasonably ask: how does all this square with the standard advice to hire a banker and run a process? Aren’t these two ideas in tension?

Not really. They operate on different timelines.

The work Roizen is describing is long-term and strategic. It’s about shaping how a potential acquirer sees your company years before any process begins — helping the right person inside the right company build a strategy that depends on you. You’re not selling the company. You’re teaching someone else why they might need to buy it. The Magic Box Paradigm is about getting bought.

A banker-led process is something else entirely. It’s about getting sold. It’s a short-term mechanism to create urgency, surface alternatives, and establish price. It can accelerate a deal. It can’t create the underlying reason for one to exist.

If the strategic groundwork has been laid — if there are multiple potential acquirers who already “get it” — then a process can work extremely well. It forces those buyers to act, on a timeline, in competition with both PE sponsors and one another.

If the ground hasn’t been laid, then the process tends to default to financial evaluation. You get Corpdev questions, lukewarm interest, and a lot of “not a priority right now.” In other words, a scaled-up and more formal version of the sad path.

One nuance here, having lived it: the hardest part is aligning timelines.

A PE-led auction runs on a clock. You set dates, people prepare bids, and the banker’s job is to keep everyone moving in a tight, predictable cadence. That’s how you create urgency and price tension.

Strategics don’t work that way. They need time — to line up a champion, to socialize the idea internally, to get product, finance, and executive buy-in. Occasionally they can turn on a dime, but that’s the exception, not the rule.

The tension is obvious. Run the process too fast and you lose the strategics. Run it too slow and you lose the auction dynamics. This is why you need to have relationships in place with strategics well before your banker process begins. Otherwise they simply cannot keep up.

The banker’s real job, in this context, is to try to align those timelines. Because the worst outcome is hearing what I once heard: “We’re very interested, but we can’t possibly execute on that timeline, so we’re going to drop out.”

And once that happens, you’ve lost exactly the buyer who might have valued you the most. Utter process failure. Think: You had one job!

So the two ideas aren’t in conflict. They’re parallel. Do the strategic work early — years before you’d contemplate selling. Then, if and when the time comes, use a banker to run a disciplined process on top of it.

Read it Early

This is not a book about how to run an M&A process. It’s a book about how deals actually form — which is a different and more important topic. The sad path exists because most founders don’t think about this until they’re already in it, at which point it’s very hard to correct.

Read it at least four years before you think you need it. Let it shape how you build relationships with potential acquirers. Help the right person inside the right company build a strategy they can’t execute without you — and make sure they realize it before you ever hire a banker.

If you do that, you may not need a process at all. And if you don’t, you can’t count on a process to save you.

# # #

Notes

[1] With a second edition published in 2023

[2] This is actually a broader problem in business. The list of things people nod at in board meetings and then promptly ignore would fill several books.

[3] Roizen’s deadpan “Value added!” is one of the funnier lines in the book.

[4] To be clear, the taint is that they’re always for sale and nobody wants to buy them. Imagine the house on a street with a perennial for-sale sign in front of it.

[5] This is counterintuitive enough that it’s worth sitting with. The instinct is to show up with a complete, polished narrative — that’s what pitching trains you to do. But a complete narrative leaves nothing for the other side to build. Their investment in the idea comes from the act of building it.

The Silicon Valley Canon, Circa 1998: A Stroll Down Software Memory Lane

Something fun happened today. A reader reached out who had been digging through my early-2000s and 2010s posts trying to understand the history of the software industry. That immediately got my attention because I love people who study history. It’s the best way to understand the present. And a great way to avoid repeating the mistakes of those who preceded you.

So I’m always happy when someone wants to talk about software history.

His specific request was interesting: he was looking for case studies or books that were popular at the time — something that would help him understand how people in the industry were thinking back then.

I decided to do him one better. In my view, the real canon of books that shaped enterprise software thinking was largely written before 2000. So I assembled the following reading list: a set of 1990s-era books on software, strategy, marketing, and the industry itself that many of us were reading while the enterprise software industry was taking shape.

Think of it as a reading-list stroll down software, and Silicon Valley, memory lane.

1990s Era Tech Marketing and Strategy Books

High-Tech Marketing

Positioning / Marketing Foundations

Technology Strategy / Innovation

Product Marketing Culture

Enterprise Sales / Go-to-Market

Economics of Software / Networks

Enterprise Technology Industry Case Studies

Software Engineering

Classical Strategy

Your ICP Starts as an Aspiration and Becomes a Regression

The concept of an ideal customer profile (ICP) has been around for a long time, but like its cousin, the minimum viable product (MVP), it is often misunderstood. In this post, I’ll offer some background commentary on the ICP concept and then build into one of my favorite sayings: your ICP starts out as an aspiration and becomes a regression.

There are four common questions around ICPs. Here they are, along with my answers:

  • Is the ICP about a person or a firm? Both. It should include firmographic as well as role (or persona) information. Example: VPs of sales at technology companies between $500M and $2B in revenues. Here, we included the size and industry of the company along with the target buyer’s title.
  • Should an ICP include a problem to be solved? Yes. VPs of sales have lots of different problems from recruiting to training to pipeline management to forecasting, just to name a few. Thus, your ICP should include the ideal person at the ideal company and the problem you’re looking to solve for them.
  • Should the ICP include adjacent systems? Yes. Deciding at the outset if you want to focus on customers using specific, adjacent systems is often critical (e.g., NetSuite vs. Oracle vs. Xero for core financials, Salesforce vs. HubSpot for CRM). The alternative is drowning in integration work while never having the time to support the idiosyncrasies of a given package which, when you do it, is usually adored by customers.
  • Should an ICP include sales qualification criteria? No. The ICP is about the buyer: this is the person we’re looking for. They have this job at this kind of company. Whether they’re out shopping right now, whether they have budget, whether they have a buying timeframe and purchasing authority are all important qualification questions, but they are not part of the ICP itself. People differ on this, I know [1].

Because the world is imperfect and it’s difficult to find “Mr. or Ms. Right” every time, it’s useful to think of the ICP as a bullseye. The absolute perfect customer is in ring 0, the next level off in ring 1, after that ring 2, et cetera. Note that I have no religion about the things you vary across the rings, but the usual candidates are: job title, industry, size, adjacent systems, and problem (aka use-case). And you might do them in unusual combinations. For example, if you think a director of finance with a budgeting problem is about as good as a manager of finance at a bigger company with an operational reporting problem, then you can put them both in ring 2.

The idea is to give you a simple and flexible model to agree on who to target and who to prioritize across sales, marketing, and product.

For a zero-to-one startup, you might focus exclusively on ring 0. As you grow you will typically get more use-cases, more industries, more adjacent systems, and thus more rings. That’s fine as long as you’re defining the rings clearly and triaging them into: hot pursue, pursue, and slow-roll or some similar encoding system.

With a few clearly established tiers you are now ready to report on ARR and pipeline by ICP tier to see if “you’re walking the talk” when it comes to your ICP. At many companies, you will find the majority of the ARR and pipeline [2] outside ring 2 or 3. In these cases, you simply aren’t living your ICP and instead suffering from a faux focus. The usual cause is an inability to control the sales force and prevent their default “chase anything” behavior [3].

The ICP is typically born in the founder’s head as an hypothesis. Think: I bet if we can build something like this, it will solve a problem like that. By the time a company has been founded and a product built, it becomes an aspiration. Think: I want to sell to people like this to solve a problem like that. So you sharpen your definitions of this and that, and add some additional targeting criteria like company size, industry, or adjacent systems. And then you go off and sell.

Let’s say it works. One day you look up and you’re now $50M or $100M in ARR. Congratulations. Should your ICP still be an intuition-driven aspiration? No. It should be a regression. Reality happened. Let’s find out what reality is telling us.

Are the people in our ICP ring 0 really our best customers?

Well, what do we mean by best? Do they have higher ASPs? Do they have shorter sales cycles? Do they renew at higher rates? Do they expand at higher rates (e.g., NRR)? Do we win new deals at higher rates? Do they give us higher CSAT scores?

At the first order, these are all just simple segmented metrics calculations that you can and should do. Your QBR and board decks should show these key metrics segmented by ICP tier [4]. And — since not all these metrics can be important — your e-team also needs to have the conversation about “what do we mean by best” so you can have a common, precise definition of the “best” customers that you are trying to target [5].

But the best answers to these questions are not performed using segment analysis [6]. Segment analysis is great for finding anomalies — e.g., why do we have a higher win rate in ICP tier 3 than tier 1? But it’s not a great technique for actually finding the impact of different variables on the success criteria.

For that, we need regression analysis. Regression analysis will tell us which variables most strongly correlate with the outcomes we want (e.g., that the strongest predictor of renewal is company size, not CSAT) [7]. A good regression analysis will tell you not only which factors most correlate with the outcome, but it can also be the best way to bucket those variables (e.g., the real breakpoint is at 250 employees, but your initial segment went from 0 to 500).

Odds are, when we do this kind of analysis we’ll find lots of surprises. Some of your intuition will be proven correct, but some won’t. And you’ll likely find entirely new variables (e.g., number of data scientists) that you didn’t even consider in your initial ICP exercises.

So this is why I like to say that your ICP starts as an aspiration — about who you want to sell to — and over time becomes a regression. Because one day you will have lots of data to analyze to determine who your best customers are — subject to your definition of best, of course — as opposed to who you thought they would be.

# # #

Notes

[1] Regardless of where you land at least be aware there are two types of criteria: those that change slowly or not at all (e.g., company size, adjacent systems, industry) and those that can change overnight (e.g., out shopping, budget, authority). My analogy here is dating: you can meet the right person at the wrong time. It doesn’t change the fact that they’re the right person. (And that’s why God made nurture tracks.)

[2] Think of pipeline as a potential leading indicator of ARR. Well, it should be, at least.

[3] Using the ICP in territory and compensation plan definitions can help with that. Think: you only earn commissions on customers in ICP rings 1 through 3 within your geographic territory. That will get your sellers’ attention.

[4] Note that I’m kind of using ICP tier and ring synonomously here and that’s generally OK. However, in cases where you have lots of rings, I would then sort those rings into tiers, so ring is the more specific and tier the more general term. For me, because I like simplicity, I want to see ICP segmentation in at most 3-4 buckets, so if there are N rings underlying those, I’d prefer to hide those by using 3-4 tiers.

[5] You probably don’t want marketing targeting high LTV prospects when sales wants to target high win rate ones. We should all be on the same targeting page.

[6] One of the key problems being that the segments themselves were somewhat arbitrarily chosen. Sure, we did our best to guess who’d be our best customers. But who are they actually? We may have used not only the wrong bucket boundaries (e.g., 100 emps vs. 500 emps) but even the wrong dimensions (e.g., maybe company size is a poor predictor and industry or use-case a powerful one).

[7] I cheated here on purpose to see if you were paying attention. Thus far, we’ve largely said the ICP is about a company (firmographics) and a role/persona. But here I’ve said that company size is a better predictor or renewal than CSAT — and CSAT isn’t a ICP-style criteria. The reality is these tools can do precisely that, looking across a wide range of input variables to see which most influence the output. Obviously, for marketing targeting purposes we don’t want CSAT to be an input variable to the model, but for renewals analysis we sure would.

Five Success Principles For Startup Founders

Back in October, I did a live workshop with my second cohort in the Balderton Launched program in London. I sat down intending to use the slides from my first session, but — always one to go with the flow — ended up improvising most of the session in response to the many great questions from participants.

I was so happy with the conversation that I jotted down a bunch of notes to make slides so I could post them. But alas, work got busy (including joining three boards) so I’ve not had time — until today.

So here, finally, are the slides that I wished I’d made before my October Balderton Launched workshop. Thanks for everyone who came along to the session and to Greta Anderson for setting it up. The PDF is here. I’ve embedded the slides below.

I can’t wait to use these with the next cohort!

Design Your Organization for the Conflicts You Want to Hear About

Organization design seems a popular topic these days. Maybe it’s the downturn. Maybe it’s just planning season. But either way, many people are asking me questions about how to design their organizations for 2025 and beyond. Questions like:

  • Should marketing report into sales?
  • Should engineering and product management (PM) report into a combined product org?
  • Should we unite customer success and sales?
  • Should North American and Europe report into a single head of sales?

The argument for combining teams is always about reducing span of control. This is a goal that many CEOs (and some boards) share, but one that somehow escaped one of the world’s most successful entrepreneurs, Jensen Huang, who has about 60 direct reports.

While 60 seems a bit much, I’ve frankly never understood span-of-control reduction as a top organization design goal. As CEO, you should be managing senior people so they shouldn’t take that much time. So, why not have 8 or 10 direct reports? If you can’t handle that, maybe the problem isn’t that you have too many reports, but that you’re managing them too closely. Maybe the solution isn’t to reduce their number, but to loosen the reins.

I have two rules for organization design:

  • Design for conflict. Specifically, design your organization for the conflicts you want to hear about.
  • Ensure value-add. Don’t put thing B under thing A unless the executive in charge can add value to both.

Design for Conflict

When you put, for example, engineering under product, what don’t you hear about anymore? Conflicts between PM and ENG about the time and resources required to build things. Those conflicts get silenced because the SVP of Product will suppress them, resolving them in the family.

When you put marketing under sales, what don’t you hear about anymore? Conflicts about whether sales strategy is too unfocused to enable marketing targeting. Or whether sales follows-up on new oppties in a timely manner. Those get silenced because the CRO wants to manage their own house. “Let’s resolve that at the sales QBR, not the e-staff meeting.”

When you put customer success under sales, what don’t you hear about anymore? Conflicts about whether sales is overselling to the point that customers won’t be successful and ergo won’t renew. If churn looks high, well, it must be the product. It’s not delivering, but against what expectations, set by whom? All silenced.

The rule is simple. By combining two departments, you are asking one person to resolve the conflicts between them. They’re not evil to do so; it’s the job you asked them to do. They will keep these conflicts in the family. And, as the organization grows, you will hire increasingly senior people to do just that. But with each layer and with each combination, you get more insulated from the ground truth.

So the question is simple: which conflicts do you want to hear about? Which do you want to pay someone else to resolve and which do you want brought to your office? Which are strategic to the company and potentially involve Crux-level issues?

  • If you separate PM and ENG, you’ll hear a lot about specs, resources, and timelines.
  • If you separate sales and marketing, you’ll hear a lot about awareness, leads, and follow-up.
  • If you separate customer success and sales, you’ll hear a lot about over-selling.

There’s no magical answer here. Just a framework for thinking about it. Determine the conflicts you want to hear about — presumably because you can add the most value in resolving them — and then design the organization to make sure you do.

Ensure Value-Add

The other principle is to always ensure value-add, beyond the (sometimes merely assumed) alignment that comes from having a common boss. So, sales wants the SDRs to report to them? Why? Has the sales VP managed an SDR team before? Are they good at it? Are they even interested in it? Can they add value? Are they sufficiently metrics and process-oriented, particularly if the VP comes from an enterprise background?

This principle drives a number of positive effects:

  • It defeats empire building. Sometimes the VP wants the SDR team not because they care about them, but because they want a bigger organization. Or they think it will look good on their resume for their next job search. They’re not actually interested in the job. They’re interested only in being able to say that they did it. That’s not good enough.
  • It encourages learning and development. When the VP of sales first asks about managing the SDRs, you can tell them to go make themselves a valid candidate. Get close to the SDRs now. Understand their challenges and offer to help out. Network with friends and colleagues on SDR team management. Read up on best practices. Convince me that you’d make the short list of candidates and then we can have a conversation.
  • You attract stronger department heads. Everyone should work for someone they can learn from. Saying the boss is the boss because, “well, we had to plug the team in somewhere,” is a terrible reason for an organizational structure. If you apply the value-add rule, functions will tend to report higher in the chain, creating a flatter org, and be placed only under those who can add value to them. This, in turn, attracts stronger candidates to run them. Who wants to be the CMO when it reports to a CRO who understands nothing about marketing? Nobody.

One great example is whether the VP of European Sales should report to the existing VP of Sales when you expand into Europe. If your VP of Sales is clever, they’ve already given themselves the title “VP of Worldwide Sales,” and you let them do it because it was moot at the time. But now they’ll argue it’s a demotion if Europe doesn’t report to them. And they’ll argue that they know how to sell the software in North America (really, the USA) and that knowledge should translate anywhere. And that everybody does it this way. You can almost hear them screaming: pick me, pick me!

But what they should be screaming is: I can add value, I can add value! And if they can, you should listen. But my questions would be:

  • Do you have a passport? (This wipes out about half of Americans.)
  • Have you ever lived in Europe?
  • Do you speak any European languages?
  • Have you ever sold and/or managed people in Europe?
  • Do you you have a network of people we can hire in Europe?
  • Do you have relationships with contacts at target customers in Europe?
  • Do you know any strategic partners we can work with in Europe?

So, other than not having a passport, never having been there, knowing no one, and not being able to communicate, you strike me as an outstanding candidate for the job.

We do this all the time nevertheless, and Europeans have grown accustomed to reporting into people who can’t add value. But for my nickel, I’d rather hire a VP of EMEA who had great answers to my questions and reported directly to me.

Mitigation Strategies

As your organization grows, you will invariably combine teams and lose your line of communication into certain conflicts. I know three ways to mitigate this:

  • Build a culture of transparency where direct reports into e-staffers are encouraged to and rewarded for speaking frankly about in-the-family problems.
  • Run an extended QBR. Don’t just invite the e-staff to the quarterly business review, but also invite people among their direct reports. For example, the head of customer success if it reports into the CRO, or the head of engineering if it reports into product. Ask them to deliver the same, standard presentation that the e-staffers do. This effectively flattens the organization by creating an extended leadership team that goes beyond the CEO’s direct reports.
  • Use reporting. Good reporting can reach through organizational layers and keep you in touch with what’s happening. For example, even if customer support doesn’t report to you and isn’t represented on the extended leadership team, you can still keep an eye on metrics and KPIs as well as simply on OKRs.

In this post, I’ve argued that the primary goal in organization design should not be reducing of span-of-control, but in surfacing conflicts most important to the company. I’ve also introduced a value-add rule that says no department should report into an executive who can’t add value to it. And finally, knowing that consolidation is inevitable over time as a successful company scales, I’ve offered three strategies to mitigate some of the signal loss that comes with such expansion.