The cleverest answer I’ve heard to the question “When would you sell your startup?” is, “When somebody offers me more than I think it’s worth.”
It’s clever alright, but it’s not that helpful. It’s a meta-answer that sidesteps the question of value. In this post, I’m going to offer a simple rule for when you should consider selling your company if someone comes along and makes a serious offer.
Selling a company is a hugely difficult decision that involves both personal considerations and big, strategic questions like:
- If I say no, what might that strategic suitor do instead? Will my top partner become my top competitor, potentially overnight?
- What is happening to the space at large? Are my competitors being gobbled up? Might I be the one left without a chair when the category consolidation music stops?
- Does the market require a Switzerland, an independent vendor who’s not owned by any of the megavendors? (For example, as data integration has historically.)
- If I “keep on keeping on” — given my size, growth rate, and financing ability — where I am likely to end up? As a clear market leader? As an undifferentiated, fifth-place also-ran? (And those don’t trade for median multiples.)
- Or, will I “pull a VMware” and sell a business for $625M that will one day be worth $60B? (And conversely, if I own 30% of it, how much difference will that 100x uplift actually make in my life?)
In this post, we’re going to keep it simple by focusing not on whether you should sell your company, but on whether you should consider selling it.
And, as is often the case, I have a simple rule. You should consider selling your company when an offer takes three years of risk off the table.
What does that mean?
- Go look at your three-year model (and this is one of many reasons why you should have one)
- Find your ARR is twelve quarters out
- Multiply that ARR by what you think will be a reasonable ARR multiple given your future growth rate
- If the offer on the table is greater than or equal to the number you just calculated, you should consider selling.
Why do I think this formula works? Because:
- Most three-year models are optimistic. For most companies, you’re looking at a best-case estimate of what ARR will be in three years.
- You’ll probably overestimate the “reasonable” multiple. If the market data suggests 4-6x, you might round up to 6-8x. Human nature.
- You’ll therefore generally arrive at a generous future valuation that will take no small amount of work to realize.
- And a lot of shit can go wrong along the way.
Why consider taking that valuation? Simple. Because building companies is hard. As one founder often said, “not just harder than you think, but harder than you can possibly imagine.” I’ve played a leading part in building four enterprise software companies and I’d say it’s just plain hard. But maybe that’s because I have a better imagination. Or an imagination fueled by more experience.
So, if you want to pay me now what I think the company will objectively be worth in three years — if everything goes smashingly — then I’m going to need to seriously consider that offer.
Note that I am not suggesting you should automatically take any offer that’s N times your 3-year forward ARR (for whatever value of N). You need to answer all those personal and strategic questions first. But I am also saying that — unless conversely you see storm clouds on the horizon — that you shouldn’t invest too much time considering offers that take 1-2 years of operating risk off the table.
Why?
- Your one-year-forward ARR is basically your operating plan. And, if you’ve followed my planning advice (“make a plan that you can beat“), then you should have pretty high confidence in that plan. So an offer that takes one year of risk off the table shouldn’t be that compelling.
- Your two-year-forward ARR is not the layup that your one-year plan should be, but if you think your model is realistic — and I admit this is completely subjective — selling off two-year-forward ARR just doesn’t seem worth it. You’re trading away future upside for a number that you’re still pretty confident you can hit. Two years is a long time, yes, but not that long.
For me, at three years, the tone changes. A lot can happen in three years. New competitors. Category consolidation. New vendors entering the space. Bad C-level hires. Product development disasters. Failed acquisitions. Geographic restarts. Channel programs that don’t take. And other scary things that go bump in the corporate night.
Yes, everything may go right over your coming three years. Maybe you’ll even beat that optimistic three-year model.
But at three years, I start to do some hard thinking about both strategic and operational risks. I’ll need to feel very good about the future to say, “no thanks, we’ll roll the dice.” Particularly if that suitor is a megavendor with intent to enter the market anyway. Or, if multiples are currently high relative to historic averages — meaning that I might get offered 10x $50M today, but by the time I’m actually at $50M, the market may be trading at 6x. That’s three more years of work for 40% less money assuming everything goes great. All because multiples moved down on me.
Let’s insert a little model to make this concrete:
Using my rule, if someone offered me $675M for this company, I’d have to seriously consider it. Note that’s 45x this year’s ending ARR and 22x next year’s. But since it’s November, I’m already worth $233M, the 15x multiple coming courtesy of my 107% growth rate. (Feel free to quibble with me on the numbers; I think they’re representative, but the approach is the point.)
- If someone offered me $354M, then I’d say no and roll the dice on achieving my operating plan. Because once I do, I’ll be objectively worth that in 12 months.
- At $535M, I start to get queasy because that’s 2.3x what the company is objectively worth today. This is why I made the model — to make things concrete — because I might well consider that offer, particularly because my decelerating growth drops my 2027 multiple to 8x, meaning only $141M of incremental value is created in 2027. I wouldn’t definitely consider it, but I probably would and I’d be arguing the whole time that we can make it worth more given “only” three years’ work. (My change in tune here is a negotiation posture.)
- At $676M, I’d definitely consider the offer for the reason stated above: that’s what the company should be objectively worth in three years if everything goes well. And a lot can go not-so-well over a three-year period.
Note that I did one sneaky thing in the model. I included the number of AEs I’d need to make those numbers using that as a rough proxy for work. To make the plan work, I’m going to have to hire 35 reps — net of attrition — over the next three years. And all the support resources they need and/or generate, e.g., SDRs, SCs, managers, post-sales consultants, CSMs. For me, it helps to make the anticipated work visceral.
Let me address some anticipated objections to this approach:
- It doesn’t consider long-term strategic value. You’re right. It doesn’t. That’s why you need to consider that under the big strategic questions. Don’t pull a VMware. Or, arguably, a YouTube.
- If I did this three years ago, I’d have sold for pennies. To be concrete, let’s say the company’s annual ARR ramp was (0, 1.0, 2.5, 7.5, 15.5), which dovetails into the table above. That means you’d have seriously considered an offer of $46.5M three years ago when you were $1.0M in ARR. If you’re VC backed, there’s no way you’d sell, so you can consider it as much as you want. And if you looked at personal and strategic considerations, you probably would have said no anyway. But yes, the rule doesn’t scale particularly well back to $0.
- This will backfire going into a valuation bubble. And it will. Say multiples now are 6-8x for your growth rate and you model off 6-8x in your three-year calculation. If the market gets frothy, those multiples could double to 12-16x. Ergo, this formula will underestimate your future value by half. I have two responses: (1) the opposite is true as well; you win when you apply bubble multiples to future non-bubble ones, and (2) the ARR figure is probably over-estimated which should mitigate but not eliminate that effect.
- It doesn’t include a hockey stick when we hit some market inflection point. That’s Silicon Valley speak for the model might underestimate three-year ARR because of [insert miracle here]. And it might. But for every 100 companies I see waiting for those miracles, maybe 2-4 get them. It’s rare. And if you really think that inflection point is going to happen, put it in the three-year model.
- All the great founders are all-in, YOLO. I have two words for you: survivor bias. I know lots of great founders who were all-in, got sunk on the river, and wish they’d taken some money off the table. Ultimately, this will come down to your personal goals. (And it’s one reason why I think VCs love second-time founders. Dave Duffield was never going to sell Workday too early because he had all the money he ever needed from PeopleSoft. And since VCs would generally rather sell too late than too early — because it’s a “hits business” — that creates a deep, natural alignment.)
My purpose here was to give you a rational framework for thinking about this decision, and here it is: think about how many years of risk gets taken off the table. That’s what you get in exchange for trading away whatever potentially bright future awaits.
The rest is up to you — and your board. Good luck with it.
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(Revised 3:59pm. Sorry, this was accidentally published before final spellchecking and copy editing was complete.)