Category Archives: Startups

CEO is Not a Part-Time Job

While I’m not that close to the whole Twitter situation and although I’m a moderately heavy user (@Kellblog), I don’t study their financials or other statistics.  That said, as a user, I feel a certain malaise around the service and I think it’s definitely in need of some new energy.

What I don’t get it is apparently soon-to-be-made permanent appointment of Jack Dorsey to CEO while simultaneously serving as CEO of Square.  Dorsey is undoubtedly an amazing guy, that’s not the question.

The question is simple:  is CEO a part-time job?  And the answer is equally simple:  no.

I can say this having worked for many CEOs over my 30 year career (e.g., at Business Objects for nearly a decade) and having been a CEO for about a decade as well between MarkLogic and Host Analytics.  No way, no how, no matter how amazing the person, CEO is not a part-time job.

Now the great part about Silicon Valley is that there are, indeed, a lot of amazing people out there.  There is no logical reason why Twitter cannot find someone amazing — who doesn’t already have a full-time job — to run the company.  So please add me to the “I don’t get it” list.

What I’m making is a general statement.  My logic is only compounded by the situation:

  • Square is working toward an IPO in the fairly short-term.  This is an extremely demanding phase for a company and its CEO.
  • Twitter has become a turnaround.  This is an even more demanding phase for company, and they don’t always end well.

So if I’m going to argue that if it’s impossible in general, then it’s kind of impossible-squared when one company is IPO mode and the other is in turnaround mode.

Is it totally unprecedented? No, per this story, but I nevertheless think it’s a bad idea, as two folks who’ve done it seem to agree.

Though rare, it’s not unheard of for a person to run two large companies. That’s what Steve Jobs did with Apple and Pixar, though he described it as “the worst time in [his] life.” Elon Musk, CEO of Tesla and SpaceX, put it more mildly: “It is quite difficult to be CEO at two companies.”

Curse of the Megaround: Expectations and Power

I’ve written before about the curse of the megaround which can happen, for example, when a startup raises $100M at a unicorn valuation and I’ve described before what typically happens next:

  • The company is under great pressure to invest the money to drive strong growth.  Late-stage investors don’t give you money to put in the bank at 0.2% interest.  They want you to invest it, typically over the next 2-3 years, implying something like an insane $15 to $20M/quarter burn rate.
  • As a result of this spending pressure the company gets inverted — instead of making a plan and finding money to finance it, the company gets a pile of money and then needs to figure out how to spend it.  This is backwards.
  • The company over-expands and over-invests.  You end up in 10 countries not 3.  You double your employee base in 9 months.  You sign up not just for projects 1-3, but for 4-9 as well.  It sounds great until you realize that half your countries are executing the wrong strategy, half the new employees can’t articulate the company message, and that projects 4-9 were down-the-list for a reason:  they were dubious ideas that shouldn’t have been funded in the first place.
  • The soon-to-be-former CEO develops a sudden interest in spending more time with his/her family.  A new CEO is hired to “bring focus” to the situation.  He/she ceases operations in 5 of the countries, lays off 35% of the employees, and shuts down projects 4-9.

If you were paying attention, you probably just noticed that $50M went up in smoke in the process.  Fortunately, in Woodsideno one can hear a venture capitalist scream.

The Math Behind the Problem:  Expectations and Power
In this post on the Silicon Valley hype machine, I argued that unicorns were the product of three trends:

  • The cost and hassle of being a public company.  Why go public if you don’t have to?
  • The ability to raise formerly IPO-sized rounds in the private markets.
  • A generally frothy environment in late-stage financing .

This got me thinking about what really differentiates a $100M IPO from a $100M late-stage private financing.  Benchmark Capital’s Bill Gurley recently did a great post on this precise subject where he points out several major differences:

  • The private round has far less scrutiny due to lack of an IPO process.  The numbers in a financing deck may not be the same numbers that would have been in the S-1.
  • In the private financing, the money is much more likely to have  perverse effects on operating discipline (as I detailed above).
  • In an IPO the company usually ends up with a single class of (common) stock, putting everyone on an equal footing.  The $100M private round will be preferred stock, with strings attached in the form of liquidation preferences.   This creates a difference between a common stockholder’s nominal and effective ownership positions and — if the business subsequently gets in any trouble — can literally wipe out the value of the common stock in an M&A exit scenario.  This can be devastating for employees who typically are unaware of the terms (e.g., multiple and/or participating preferences) that create the gap between nominal and effective ownership.

While I think Bill’s post his excellent, I think he missed two factors that are particularly important from the CEO’s perspective:  expectations and power.  Specifically, what are the go-forward expectations for the stock and what is the power of the people who have them?

In the IPO scenario, there is a short-term expectation of an immediate pop in the stock price, which is conveniently handled by the endemic under-pricing of IPOs.  So, assuming that takes care of itself through the usual process, what are the general expectations of an IPO stock after that, say during the next three years?

I spent some time researching this, looking at several studies and reviewing the capital asset pricing model.  Since I didn’t find any authoritative source (and since many IPOs actually under-perform), I will somewhat arbitrarily suggest that an public-market investor would be happy with a 20 to 25% annual return on an IPO stock purchased a few days after the offering.  I would be.

What does our late-stage private investor want?  Everybody knows that:  the rule of threes.  They want a 3x return over 3 years.  That’s a 44% annual return.   And, in today’s markets, that will often be atop a considerably higher initial valuation.

So the first big difference is about expectations.  Our private buyer expects roughly double the return of our public buyers.

The second big difference is about power:  who, exactly, wants that return?

  • In the IPO scenario, it’s a series of portfolio managers at institutions like Fidelity who each own positions worth single-digit millions.  If they get mad at you, they can sell their shares or their sell-side analysts can downgrade the stock.
  • In the private scenario, it’s a board member from a VC/PE firm that owns maybe $75M worth of stock.  If they get mad at you, they can try to fire the CEO at the next board meeting.

So other than getting an investor with infinitely more power seeking double the return, in an environment with far less scrutiny over the numbers, in a situation more likely to cause a loss of operational discipline, and the use of structure / preferences that create potentially large gaps between nominal and effective ownership, there’s no real difference between doing a $100M private round and an IPO.

Well, at least the CEO can sometimes sell into the late-stage round.  He or she may well need to.

The Venture Capital Inversion

There used to a be time in Silicon Valley when a startup created a strategy, made a business plan to go execute it, and then raised the amount of money required to execute the business plan.

That seems pretty  quaint these days.  Because today, many companies have this upside-down.  Instead of making a plan and raising funds to execute it, they raise a pile of money and then go figure out how to spend it.

This is happening largely because of the frothy, particularly mid- to late-stage financing environment that exists today.  More and more money is going into later-stage VC and PE growth funds, funds get bigger, minimum check sizes get bigger, and all of sudden you have a bunch of investors who each need to write checks of $50M to $100m to make their funds work and those check sizes start dominating round sizes in Silicon Valley.

But it’s all upside down.  Companies shouldn’t raise more money because investors want to write bigger checks.  Companies should only raise more money if they need it to fund their plan.

A key part of building a startup is focus.  Flooding companies with money works against focus.  Remember the startup epitaph:


When startups “just do both” they fail to choose — in so doing, often choose to fail.  When you flood a startup with money, it tends not just to do both, but perhaps all 4 or 5, of the ideas that were in discussion.

When a company gets caught in the VC inversion bad things happen.  For details, see this post I wrote entitled Curse of the Megaround, but the short summary is that startups with too much cash make too many questionable investments that defocus the company and don’t provide returns, ultimately resulting in the termination of the CEO and usually a chunk of the executive team along with him/her.  In short, turmoil.

Remember this tweet from Marc Andreessen:


So the next time you hear a company celebrating a $100M round ask yourself these questions:

  • Can they actually put the money to productive use?
  • What distractions will they start or continue to invest in?
  • How much longer will the CEO and executive team last given the new, heavy pressure put on the valuation?

Startups should be about entrepreneurs driving a vision for customers that benefits the founders and employees, with the VCs along for the ride.  Let’s not get that inverted and end up with startups being run for the late-stage investors with the customers, employees, and founders along for the ride.

Are Your Managers Good Enough? A Simple Test

When I listen to senior executives talk about their first- and second-line managers, I sometimes get pretty concerned.  That happens when I hear what I call “good enough” thinking.

“Yeah, he’s not great, but he’s good enough.”

“She’s doing a solid job, but nothing too inspirational.”

“He’s not a great manager, but he can stay on top of the business.”

The purpose of this post is a to provide a brief inspirational reminder:  good enough isn’t.

I know why executives and managers fall victim to “good enough” thinking:

  • Hiring is hard
  • Management is hard
  • Hiring managers is therefore hard^2

So while most executives demand excellence from their front-line employees, they seem to dial back their expectations when it comes to management.  The only thing scarier than hiring new salesreps or product managers is hiring sales managers or product management directors.  Scary though it may be, it’s their job to do so.

In mulling this, I have come up with a simple test to determine if you managers are good enough:


If your managers don’t pass that test, then maybe they shouldn’t be managing.

More Turmoil at Adaptive Insights

I always have mixed feelings about competitive blog posts and to keep my life simple and the blog pure, I generally try to avoid doing them.  However, for a bevy of reasons related primarily to how Adaptive Insights chooses to compete with Host Analytics, I have made and will continue to make a few exceptions.

From the day I joined Host Analytics, Adaptive made a deliberate FUD campaign against Host Analytics and aimed very much at the company.

  • They’d point out I was a new CEO and that new was scary.  They’d forget to say experienced CEO who already grew a company to $80M, knew the BI/EPM category, and was running a $500M division at Salesforce.
  • They’d say we had scary management turnover.  They’d forget to say that I was building a new team to take the company to the next level and rather than examining the simple fact of change, you should evaluate whether the change was good or bad.  The real question was whether the team I was building was well suited to moving the company forward.  Did the people have the right experience?  Had they built startups before?  Did they know the category?
  • They’d talk about their funding and tell customers (crossing the defamation line in my humble opinion) that we were risky to buy from due to financing issues.  Anaplan shut that down pretty fast after raising a $100M round and to date Crunchbase reports that Host Analytics has raised $86M and Adaptive $101M — no big difference there.
  • They’d boast that they hired our former people.  They’d forget the part about “that we didn’t want.”  In my tenure we’ve never hired someone in the reverse direction, and I don’t expect we will.  Our aim is to be “the Hyperion of the cloud” and you don’t get there with low-end people pumping low-end product.

Adaptive’s argument was simple:  customers should (1) buy from the company who’s raised the most money in the space and (2) not buy from a company if they have had senior management changes.  Thus, I am pleased to report by Adaptive’s own “insights” (i.e., reasoning), that customers should not buy from them.


If you want the company whose raised the most capital, it’s not Adaptive, it’s Anaplan at $144M.

Note that I never made the argument that most money is best.  Business Objects was grown to $1B+ in revenues on something like $4M in VC.  Tableau is worth $8B today and was built on $15M in (as I hear it, unneeded) VC.  In my opinion, when it comes to startups and VC, the Goldilocks rule applies:  neither too much nor too little — but just right.

If you want to avoid companies with management turmoil, consider the following:

  • By my count, Adaptive Insights is on its fourth CEO since 2011.  Count:  (1) the interim guy whose name I can’t remember, (2) Rob Hull who I believe acted as interim at some point, (3) John Herr who was exited in July 2014, and now (4) retired East Coast venture capitalist Tom Bogan.
  • Long-time SVP of Sales Neil Thomas left the company this past November after 8 years.

Quick: what’s the #1 reason people with quotas suddenly leave companies?

I will try to avoid the tendency to editorialize about the subjective question of whether the new team is the right one, with the right experience, in the right categories, et cetera and simply observe this fact:  if you believe Adaptive’s argument that you should not buy from companies with management changes, then you shouldn’t buy from Adaptive.



Bottom-Fishing Acquisitions and Catching Falling Knives

As mentioned in my recent Curse of the Megaround post, some companies that find themselves flush with cash and under heavy pressure to grow, decide to embark on dubious acquisitions to help shore up the growth story.

As one reader it put it, you can summarize your megaround post with the simple phrase “much money makes you stupid.”  And it can.  Thus, as the old saw goes, fools and their money are soon parted.

What separates good from bad acquisitions in this context?  As a general rule, I’d say that when high-growth venture-backed companies acquire firms that would otherwise best be acquired by private equity, it’s a bad thing.  Why?

Firms destined to be acquired by private equity follow a typical pattern.

  • They are old, typically 10+ years
  • They have tried multiple iterations on a strategy and none has worked
  • They have a deep stack of technology built over the years but most of which could be quickly replaced with modern, often open source, standard components
  • They tend to get strategically inverted — starting out with “what we have” as opposed to “what the market wants”
  • They have gone through several generations of management teams
  • Basically, they’re turnarounds

So private equity funds bottom-fish these opportunities, buy companies for a fraction of the total invested venture capital, scrap most of the original dream and either [1] double down on one core piece that’s working or [2] roll the company up with N adjacent companies all selling to the same buyer.

This is hard work.  This is dirty work.  This is “wet work” involving lots of headcount changes.  And private equity is good at it.   In one sense (and excluding private equity growth funds), it’s what they do.

High-flying VC backed startups are simply the wrong types of buyers to contemplate these acquisitions.  In the core business, it’s all about grow, grow, and grow.  In the acquired business, it’s all about cut, cut, cut and focus, focus, focus.  These are two very different mentalities to hold in your head at one time and the typical fail pattern is apply the grow-grow-grow mentality to the broken startup that repeatedly hasn’t-hasn’t-hasn’t.

The other failure pattern is what I call the worst-of-breed suite.  This happens when a player in space X acquires a two-bit player in space Y, hoping to “get a deal” on a cheap technology they can then sell to their customers.   The vendor is thinking “I can sell more stuff through my existing channel.”  However, the customer is thinking “I don’t want to use a worst-of-breed product just because you decided to acquire one on the cheap.”  Moreover, with easy of integration of cloud services, there is typically no real integration advantage between the cheaply acquired product and a third-party best-of-breed one.

On Wall Street, they say that bottom-fishing falling stocks is like catching falling knives.  For high-growth startups, trying to bottom-fish failed startups is pretty much the same thing.

The Curse of the Megaround

With what everyone seems reluctant to call a bubble in late-stage, private financing in full swing, I thought I’d do a quick post to drill into a concept I presented in my 2015 predictions post, something I call the curse of the megaround.

We will do that by examining the forces, and the winners and losers, surrounding a megaround.  Let’s start with a hypothetical example. Company X raises $200M at $1B pre-money, giving them a $1.2B post-money valuation.

Champagne is popped, the financing is celebrated, the tech press bows, and the company is added to many unicorn trackers.

Now what happens?

  • The CEO is under immediate pressure to invest the additional capital.  If you take the rule of thumb that most venture rounds are designed to last 18-24 months, then a $200M raise implies a cash burn rate of $8 to $10M/month or $25 to $30M/quarter.  That is an enormous burn rate and in many cases it is difficult or impossible to spend that much money wisely.
  • The CEO is under heavy pressure to triple the value of the company in 2-3 years.  The investors who do these rounds are typically looking for a 3x return in 2-3 years.  So the CEO is under huge pressure to make the company worth $3.6B in 2-3 years.
  • This, in turn, means the CEO will start investing the money not only in promising growth initiatives, but also dubious ones.   Product lines are over-extended.  Geographic over-expansion occurs.  Hiring quality drops — in an attempt to not fall behind the hiring plan and lose all hope of achieving the numbers.
  • In cases, money is waste en masse in the form of dubious acquisitions, in the hope of accelerating product, employee, and customer growth.  However, the worst time to take on tricky acquisitions is when a company is already falling behind its own hypergrowth plans.
  • All of this actions were done in the name of “well, we had no hope of making the plan if we didn’t open in 12 countries, hire 200 people, add 3 product lines, and buy those 2 companies.”  So we may as well have tried as we would have been fired anyway.  At least we gave it our best shot, right?
  • This often comes to a head in a Lone Ranger moment when the board turns on the CEO.  “Didn’t we agree to that hiring plan?  Didn’t we agree to those product line extensions?  Didn’t we agree to that acquisition?” the CEO thinks.  But the board thinks differently.  “Yes, we agreed to them, but you were accountable for their success.”

Yes, being CEO can be a lonely job.  This is why I call it the curse of the megaround — because it’s certainly a curse for the CEO.  But the situation isn’t necessarily a curse for everyone.  Let’s examine the winners and losers in these situations.


  • The founders.  They get the benefit of a large investment in their company at low dilution without the downside of increased expectations and the accountability for delivering against them.
  • The private equity fund managers.  Provided the turmoil itself doesn’t kill the company and new, more realistic plans are achieved, the PE fund managers still get their 2+20 type fee structure, earning 2% a year baseline and 20% of the eventual upside as carry.  In a “more normal” world where companies went public at $300M in market cap, there would be no way to earn such heavy fees in these investments.


  • The CEO who is typically taken out back and shot along with any of the operating managers also blamed for the situation.
  • The company’s customers who are typically ignored and under-served during the years of turmoil where the company’s focus is on chasing an unreachable growth plan and not on customer service.
  • In the event the company is sold at a flat or down valuation, the common stock holders (including founders and employees) who can see their effective ownership either slashed or wiped-out by the multiple liquidation preferences often attached to the megaround.  (People love to talk about the megaround valuation, but they never seem to talk about the terms that go with it!)
  • The private equity limited partners whose returns are diminished by the very turmoil their investment created and who are stuck paying a high 2+20 fee structure with decade-ly liquidity as opposed to the 1% fee structure and daily liquidity they’d have with mutual funds if the companies were all public (as they would have been pre-Sarbox.)
  • The private equity limited partners who ultimately might well end up with a down-round as IPO.

In some situations — e.g., huge greenfield markets which can adopt a new solution quickly and easily — a megaround may well be the right answer.  But for most companies these days, I believe they are more curse than blessing.