Category Archives: Venture Capital

The Red Badge of Courage: Helping Overachievers to Manage and Process Failure

When I lived in France for five years I was often asked to compare it to Silicon Valley in an attempt to explain why — in the land of Descartes, Fourier, and Laplace, in a country where the nation’s top university (École Polytechnique) is a military engineering school that wraps together MIT and West Point, in a place that naturally reveres engineers and scientists, why was there not a stronger tech startup ecosystem?

My decade-plus-old answer is here: Is Silicon Valley Reproducible? [1]

My answer to the question was “no” and the very first reason I listed was “cultural attitudes towards failure.” In France (at least at that time) failure was a death sentence. In Silicon Valley, I wrote, failure was a red badge of courage, a medal of valor on one’s resume for service in the startup wars, and a reference to the eponymous classic written by Stephen Crane.

In this post, I want to explore two different aspects of the red badge of courage. First, from a career development perspective, how one should manage the presence of such badges on your resume. And second, from an emotional perspective, how thinking of startup failure as a red badge of courage can help startup founders and employers process what was happened.

Managing Failure: Avoiding Too Many Consecutive Red Badges

In Silicon Valley you’ll often hear adages like “failure is a better teacher than success,” but don’t be too quick to believe everything you hear. While failure is certainly not a scarlet letter in Silicon Valley, companies nevertheless hire for a track record of success. In the scores of C-level position specifications that I’ve read and collected over the years, I cannot recall a single one that ever listed any sort of failure as required experience.

We talk as if we love all-weather sailors, but when it comes to actually hiring people — which often requires building consensus around one candidate in a pool [2] — we seem to prefer the fair-weather ones. Back in the day, we’d all love a candidate who went from Stanford to Oracle to Siebel to Salesforce [3].

But, switching metaphors, I sometimes think Silicon Valley is like a diving competition that forgot the degree of difficulty rating. Hand a CEO $100M, 70% growth company — and the right to burn $10M to $15M per quarter — and it will likely go public in a few years, scoring the company a perfect 10 — for executing a swan dive, degree of difficulty 1.2.

Now, as an investor, I’ll put money into such swan dives whenever I can. But, as an operator, remember that the charmed life of riding in (or even driving) such a bus doesn’t necessarily prepare you for the shocks of the regular world.

Consider ServiceMax who, roughly speaking, was left at the altar by Salesforce with a product built on the Salesforce platform and business plan most thought predicated on an acquisition by Salesforce. That team survived that devastating shock and later sold the company for $900M. That’s a reverse 4½ somersault in pike position, degree of difficulty 4.8. Those folks are my heroes.

So, in my estimation, if Silicon Valley believes that failure is a better teacher than success, I’d say that it wants you to have been educated long ago — and certainly not in your most recent job. That means we need to look at startup failure as a branding issue and the simple rule is don’t get too many red badges in a row on your LinkedIn or CV.

Using Grateful Dead concert notation, if your CV looks like Berkeley –> Salesforce –> failure –> Looker, then you’re fine. You’ve got one red badge of courage that you can successful argue was a character-building experience. However, if it looks like Berkeley –> Salesforce –> failure –> failure –> failure, then you’ve got a major positioning problem. You’ve accidentally re-positioned yourself from being the “Berkeley, Salesforce” person to the “failed startup person.” [4]

How many consecutive red badges is too many? I’d say three for sure, maybe even two. A lot of it depends on timing [5].

Practically, it means that after one failed startup, you should reduce your risk tolerance by upping the quality bar on your next gig. After two failed startups, you should probably go cleanse and re-brand yourself via duty at a large successful vendor. After a year or two, you’ll be re-positioned as a Brand-X person and in a much better position to again take some career risk in the startup world [6].

Processing Failure: Internalizing the Red Badge Metaphor

This second part of this post deals with the emotional side of startup failure, which I’m going to define quite broadly as materially failing to obtain your goals in creating or working at a startup. Failure can range from laying off the entire staff and selling the furniture to getting an exit that doesn’t clear the preference stack [7] to simply getting a highly disappointing result after putting 10 years into building your company [8]. Failure, like success, takes many forms.

But failures also have several common elements:

  • Shock and disappointment. Despite knowing that 90% of startups fail, people are invariably shocked when it happens to them. Remember, startup founders and employees are often overachievers who’ve never experienced a material setback before [9].
  • Anger and conflict. In failed startups there are often core conflicts about which products to build, markets to target, when to take financing, and whether to accept buy-out offers.
  • Economic loss. Sometimes personal savings are lost along with the seed and early-round investors’ money. With companies that fail-slow (as opposed to failing-fast), opportunity cost becomes a significant woe [10].

For the people involved in one — particular the founders and C-level executives — a failed startup feels Janis Joplin singing:

Come on. Come on. Come on. Come on. And take it! Take another little piece of my heart now, baby! Oh, oh, break it! Break another little bit of my heart now Darling yeah, yeah, yeah, yeah.

I was reminded of this the other day when I had a coffee with a founder who, after more than four years, had just laid of his entire team and sold the furniture the week before.

During the meeting I realized that there are three things people fresh from failed startups should focus on when pursuing their next opportunity:

  • You need to convince yourself that it was positive learning experience that earned you a red badge of courage. If you don’t believe it, no one else will — and that’s going to make pursuing a new opportunity more difficult. People will try to figure out if you’re “broken” from the experience. Convincing them you’re not broken starts out with convincing you. (Don’t be, by the way. Startups are hard. Cut yourself some slack.)

  • You need to suppress your natural desire to tell the story. I’m sure it’s a great story, full of drama and conflict, but does telling it help you one iota in pursuing a new opportunity? No. After leaving MarkLogic — which was a strong operational success but without an investor exit — I was so bad at this that one time a VC stopped me during a CEO interview and said, “wow, this is an amazing story, let me get two of my partners to hear it and can you start over?” While I’m sure they enjoyed the colorful tale, I can assure you that the process didn’t result in a dynamite CEO offer. Tell your story this way: “I [founded | worked at] a startup for [X] years and [shut it | sold it] when [thing happened] and we realized it wasn’t going to work. It was a great experience and I learned a lot.” And then you move on. The longer you talk about it, the worse it’s going to go.

  • You need to convince prospective employers that, despite the experience, you can still fit in a round hole. If you were VP of product management (PM) before starting your company, was a founder/CEO for two years, and are now pursuing a VP of PM role, the company is going to wonder about two things: (1) as per the above, are you broken as a result of the experience and (2) can you successfully go back into a VP of PM role. You’ll need to convince them that PM has always been your passion, that you can easily go back and do it again, and in fact, that you’re quite looking forward to it. Only once that’s been accomplished, you can try to convince them that you can do PM even better than before as a result of the experience. While your natural tendency will probably be to make this argument, remember that it is wholly irrelevant if the company doesn’t believe you can return to the role. So make sure you’ve won the first argument before even entertaining the second.

# # #

Notes

[1] A lot has presumably changed since then and while I sit on the board of a French startup (Nuxeo), I no longer feel qualified, nor is the purpose of this essay, to explore the state of tech entrepreneurship in France.

[2] And ergo presumably reduces risk-taking in the process.

[3] And not without good reason. They’ve probably learned a lot of best practices, a lot about scaling, and have built out a strong network of talented coworkers.

[4] Think of how people at a prospective employer might describe you in discussing the candidates. (“Did you prefer the Stanford/Tableau woman; the CMU/Salesforce man; or the poor dude who did all those failed startups?”)

[5] Ten years of impressive growth at Salesforce followed by two one-year failures looks quite different than three years at Salesforce followed by two three-year failures. One common question about failures is: why did you stay so long?

[6] And see higher quality opportunities as a result.

[7] Meaning investors get back all or part of what they are entitled to, but there is nothing leftover for founders and employees.

[8] And, by extrapolation, expected that they never world.

[9] For example, selling the company for $30M, and getting a small payout via an executive staff carve-out.

[10] Think: “with my PhD in AI/ML, I could have worked at Facebook for $1M per year for the past six years, so in addition to the money I’ve lost this thing has cost me $6M in foregone opportunity.”

Whose Company Is It Anyway? Differences between Founders and Hired CEOs.

Over the years I’ve noticed how different CEOs take different degrees of ownership and accountability when it comes to the board of directors.  For example, once, after a long debate where the board unanimously approved a budget contingent on reducing proposed R&D spending from $12M to $10M, I overhead the founder/CEO telling the head of R&D to “spend $12M anyway” literally as we walked out of the meeting [1].  That would be one extreme.

On the other, I’ve seen too-many CEOs treat the board as their boss, seemingly unwilling to truly lead the company, or perhaps hoping to earn a get out of jail free card if good execution of a chosen plan nevertheless fails.

This all relates to a core Kellblog theme of ownership — who owns what — that I’ve explored in some of my most popular posts:

Let’s now apply the same kind of thinking to the job of the CEO.  Startup CEOs generally fall into one of two categories and the category is likely to predict how they will approach the ownership issue.

Founder CEOs:  It’s My Company

Founders think it’s their company, well, because it is.  Whether they currently own more than 80% or less than 5% of the stock, whether they currently even work there anymore or not, it’s their company and always will be.  CEOs will come and go along a startup’s journey, but there is only one founder [2].  The founder started the company and made a big cultural imprint on it.  Nothing can take that away.

However, as soon as a founder/CEO raises venture capital (VC) they have decided to take investing partners along on the journey.  The best VC investors view their relationship with the founder as a partnership:  it’s the founder’s company, we are investing to partner with the founder, and our primary job is to advise and support the founder so as to help maximize the outcome.

However, VC investors are material shareholders, typically negotiate the contractual right to sit on the board of directors, and have certain governance and fiduciary duties as a part of sitting on the board.  (Those fiduciary duties, by the way, get complicated fast as VC board members also have fiduciary duties to their funds as well [3].)

Most of the time, in my experience, VCs run in advice/support mode, but if a company starts to have continual performance problems, is considering a new financing, or evaluating potential exit opportunities (e.g., M&A), founders can get a quick (and sometimes stark) reminder of the “second hat” that their VCs wear.

While it’s always spiritually the founder’s company, it’s only really and totally the founder’s company if they’ve never raised money [4].  Thankfully, most founder/CEOs don’t need to be reminded of that.  However, some do [5].

Hired CEOs:  It’s the Board’s Company vs. It’s My Company to Run

You become a hired CEO primarily through one path — climbing the corporate ladder at a large tech company [5a], reaching the GM or CXO level, and then deciding to branch out.  While virtually all hired CEOs have been large-tech CXOs or GMs, not all large-tech CXOs or GMs are wired to be successful as CEOs in the more frenetic world of startups.

Regardless of whether they should take the plunge, the problem that CEOs sometimes face is fighting against decades of training in climbing the corporate ladder.  Ladder-climbing wires you with three key priorities [6]:

  • Always make the boss look good
  • Never surprise the boss
  • Build strong relationships with influential peers

The problem?  When you’re CEO of a startup there is no boss and there are no peers.  Yes, there is a board of directors but the board/CEO relationship is not the same as the manager/employee relationship with which corporate execs are so familiar.

Yes, boards provide strategic and financial input, support, guidance, help with recruiting, and occasionally help with sales, but boards don’t run companies.  CEOs do.  And to repeat one of my favorite CEO quotes from Sequoia founder Don Valentine:  “I am 100% behind my CEOs up until the day I fire them” [7].

The challenge for hired CEOs is for them to understand:  it’s not my company in the sense that I founded it, but it is my company to run.  It’s not the board’s company to run and the board is not my manager.  The board is my board, and it’s not at all the same relationship as manager/employee.
Because this is somewhat conceptual, let’s provide an example to make this concrete.

“It’s My Company” Thinking “It’s the Board’s Company” Thinking
Based on what is happening in the market and our models we think it’s best to shoot for growth of X% and EBITDA margin of Y% How much do you want us to grow next year and at what EBITDA margin?
We believe we need to focus on a vertical and we think Pharma is the best choice. We were thinking that maybe we could focus more on a vertical, what do you folks think?
We think we should hold off doing channels until we’ve debugged the sales model. You told us to do channels so we signed up 17 partners but no one is actually selling anything.  Maybe it wasn’t a great idea.
Pattern:  we think we should do X and here’s why.  Please challenge it. Pattern:  we are here to do what you want, so what do you want us to do?  

CEOs need to remember that:

  • The management team spends 50-60 hours/week working at the company.  The board might spend that same amount of time in a year [8].  The team is much, much closer to the business and in the best position to evaluate options.
  • Even if they don’t always sound that way, the board wants the CEO to lead.  The scariest thing a new CEO can say is “it looks like you guys had a bad quarter” [9]. The second scariest thing is “looks like we had a bad quarter, what do you want us to do about it?”  Instead, they want to hear, “we had a bad quarter and here’s our plan to get things back on track.  Please give us frank feedback on that plan because we want the best plan possible and we want it to work [10].”
  • The CEO’s job is not to execute the board’s plan.  The CEO’s job is to work with the team to create the plan, get board approval of it, and then execute.  If the plan doesn’t work, the CEO doesn’t get to say “but you approved it, so you can’t fire me.” The job was to both make and execute the plan.

Finally, there are certain risk factors that can increase the chance a hired CEO will adopt the wrong type of thinking:

  • PE-backed firms.  In most venture-backed firms, a hired CEO will find a board consisting of several different venture capital partners, each with their own opinion.  Even though most venture boards do end up with an Alpha member [11], it’s still hard for the CEO to get confused and think of the Alpha member as the boss.  In a PE-backed firm, however, the board may consist of a single investing partner from the one firm who owns the company, perhaps accompanied by a few more junior staff.  In this case, it’s fairly easy for the CEO to revert to CXO-mode and treat that board member as “the boss” as opposed to “the board.”  While PE firms are more active managers who often come with playbooks and best practices consultants, they still want the CEO to be the CEO and not the EVP of Company.
  • First-time CEOs.  Veteran CEOs have more time to learn and understand the board/CEO relationship.  First-timers, fresh from climbing the corporate ladder, sometimes have trouble with the adjustment.

If you’re in either of the above categories or both, it’s important to ask yourself, and most probably your board, about what kind of relationship is desired.  Most of the time, in my estimation, they hired a CEO because they wanted a CEO and the more leadership you take, the more you think “my company” and not “board’s company,” the better off everyone will be.

Finally, you may also want to read this post about the board/CEO relationship which includes another of my favorite passages, on what I call the Direction Paradox.

The Direction Paradox
While discussions, challenges, advice, and questioning are always good, when boards give operational direction (i.e., “you should do X”) they risk creating a paradox for the CEO.  It’s easy when the CEO agrees with the direction and in that case the direction could have been offered as advice and still would have been heeded.
It gets hard when the CEO disagrees with the direction:

Case 1:  If the CEO follows the direction (and is correct that it was wrong), he or she will be fired for poor results.
Case 2:  If the CEO fails to follow the direction, his or her political capital account will be instantly debited (regardless of whether eventually proven right) and he or she will eventually be fired for non-alignment as the process repeats itself over time.

In case 1, the CEO will be surprised at his termination hearing.  “But, but, but … I did what you told me to do!”  “But no,” the board will reply.  “You are the CEO.  Your job is to deliver results and do what you think is right.”  And they’ll be correct in saying that.

Once caught in the paradox, weak CEOs die confused on the first hill and strong ones die frustrated on the second.

See the post for advice on how to prevent the Direction Paradox from starting.

# # # 

Notes
[1] And clearly within earshot of the directors

[2] To simplify the writing, I’ll say “one founder” meaning “one founder or equivalent” (i.e., a set of co-founders).  To the extent that this post is really about the CEO role, then it does flip back to one person, again — i.e., that co-founder (if any) who decided to take the CEO role.  This post isn’t about non-CEO co-founders, but instead about [co-]founder CEOs.

[3] See this 27-page classic (PDF) by Wilson Soncini, The Venture Capital Board Member’s Survival Guide:  Handling Conflicts While Wearing Two Hats.  It’s a must-read if you want to understand these issues.

[4] Increasingly, experienced founders (and/or those sitting on a hot enough hand) are able to raise venture capital and maintain near-total control.  Mechanisms include: a separate class of founder stock with 10x+ voting rights; control of a majority of the board seats; or protective provisions on the founder stock, such as the right to block a financing or sale of the company.  Even in such cases, however, a high-control founder still has fiduciary duties to the other shareholders.

[5] I believe incubators (and the like), by removing a lot of hard work and risk in starting a company, can inadvertently produce what I call “faux founders” who — when it comes to the business side of the company — act more like first-time hired CEOs than typical founders.  Don’t get me wrong, plenty of fine founder/CEOs come out of incubators, but I nevertheless believe that incubators increase the odds of creating a founder/CEO who can feel more like a CTO or CPO than a CEO.  That’s not to say the company won’t be successful either with that original founder or a replacement; it is to say, in my experience, that incubator founders can be different from their non-incubated counterparts.

[5a] And even better, helping to make it large while so doing.

[6] Like it or not, it’s not a bad three-part formula for climbing the corporate ladder.  And the “don’t surprise” rule still applies to boards as it does to managers.

[7] Note that any idea that the CEO might quit doesn’t seem to exist in his (or most VC’s) mind.  That’s because it’s incomprehensible because it’s a career mistake that may well make the person unemployable as CEO in a future VC-backed startup.  Who, after all, wants to hire the Captain of the Costa Concordia?  See this post, Startups CEOs and the Three Doors, for more.

[8] 6 board meetings at 4 hours = 24 hours, one hour prep per board meeting = 6 hours, 2 hours x 4 committee meetings = 8 hours, 2 hours/month on keeping up with news, updates, monthly reports = 24 hours.  Total of 62 hours/year for a committee member, less if not.  Time can vary widely and may be much higher if the board member is providing ad hoc support and/or ad hoc projects.

[9] Oh no!  The new CEO doesn’t even yet consider himself one of us!

[10] Because it’s not about ego or authorship, it’s about the best results.

[11] Often, but not always, the person who led the Series A investment.

My Appearance on the Private Equity Funcast

Who else but my old friend Jim Milbery, a founding partner at ParkerGale, could come up with a podcast called the Private Equity Funcast, complete with its own jingle and with a Thunderbirds-inspired opening?

Jim and I worked together at Ingres back in the — well “pre-Chernobyl” as Jim likes to put it.   When we met, he was a pre-sales engineer and I was a technical support rep.  We’ve each spent over 25 years in enterprise software, in mixed roles that involve both technology and sales & marketing (S&M).  Jim went on to write a great book, Making the Technical Sale.  I went on to create Kellblog.  He’s spent most of his recent career in private equity (PE) land; I’ve spent most of mine in venture capital (VC) land.

With a little more time on my hands these days, I had the chance to re-connect with Jim so when I was in Chicago recently we sat down at ParkerGale’s “intergalactic headquarters” for a pretty broad-ranging conversation about a recent blog post I wrote (Things to Avoid in Selecting an Executive Job at a Startup) along with a lot of banter about the differences between PE-land and VC-land.

Unlike most podcasts, which tend to be either lectures or interviews, this was a real conversation and a fun one. While I’m not sure I like the misparsing potential of their chosen title, Things To Avoid in Selecting an Executive Job with Dave Kellogg, I’ll assume the best.  Topics we covered during the fifty-minute conversation:

  • The pros and cons of CEOs who want to get the band back together.
  • Pros and cons of hiring people who have only worked at big, successful companies and/or who have only sailed in fair weather.
  • The downsides of joining a company that immediately needs to raise money.
  • How CMOs should avoid the tendency to measure their importance by the size of their budget.
  • Should companies hire those who “stretch down” or those who “punch above their weight”?
  • The importance of key internal customer relationships (e.g., the number-one cause of death for the CMO is the CRO) and how that should affect the order of your hires when building a team.
  • Feature-addicted founders and product managers (PMs), technical debt, and the importance of “Trust Releases.”
  • Pivoting vs. “traveling” when it comes to startup strategy.
  • The concept of Bowling Alleys within Bowling Alleys, which we both seem to have invented in parallel.  (Freaky.)
  • The difference between knocking down adjacent markets (i.e., “bowling pins”) and pivots.
  • Corporate amnesia as companies grow and surprisingly fail at things they used to know how to do (e.g., they forget how to launch new products).
  • My concept of reps opening new markets with only a telephone, a machete, and a low quota.
  • My pet peeve #7: salespeople who say it’s impossible to sell into an industry where the founders managed already to land 3-5 customers.
  • The difference between, in Geoffrey Moore terms, gorillas and chimps.
  • How there are riches in the niches when it comes market focus.
  • How feature differentiation can end up a painful axe battle between vendors.
  • Thoughts on working for first-time, non-founder CEOs in both the PE and VC context.
  • The difference between approval and accountability, both in formulating and executing the plan.

Here are some other episodes of the Private Equity Funcast that I found interesting:

So my two favorite podcasts are now The Twenty Minute VC on the venture side and The Private Equity Funcast on the PE side.  Check them both out!

Thanks for having me on the show, Jim, and it was a pleasure speaking with you.

Avoiding the Ten-Year Stock Option Trap (and Other Stock-Option Considerations)

I’ve increasingly spoken to startup employees who find themselves in a difficult trap.  Let’s demonstrate it via an example:

Say you joined a startup in September 2009 as an early employee and immediately received a stock-option grant of 400,000 shares with a strike price of $0.10 when you joined.  The company, while having experienced some ups and downs over the years, has done very well.  At its last 409a valuation, the common stock was valued at $10/share [1].  You feel great; after all, you’re a paper millionaire, with an option worth about $4M [2].

What could possibly be the problem in this seemingly great situation?  Well, sometime in the next 45 days that stock-option is going to vaporize and become worthless.  

More scarily, what needs to happen for that option to become worthless?  Absolutely nothing.  Nobody has to say or do anything.  No notices need to be sent.  Sometime in the next 45 days that option will silently cease to exist [3].  If the company gets acquired two years later at $20/share and you’re expecting an $8M payout you’re going to be rudely surprised to find you get nothing.

The Silent Killer
What happened?  What is this silent killer of stock option value?  Expiration.  The option expired ten years after its grant date.

The vast majority of Silicon Valley stock option plans feature options that expire after ten years.   In this example, your option was granted in September 2009 which means that by October 1, 2019 that option will be expired.  And the really scary part is that nobody needs to tell you it’s about to happen.

While some companies are undoubtedly more proactive than others in both helping employees avoid getting into this situation and warning them as it approaches, in the end, it’s up to you to make sure you don’t get caught in this trap.  Technically, the company doesn’t need to say or do anything.  And – to be clear — because it’s a relatively new phenomenon in Silicon Valley the company may not even have noticed it’s happening and, even if it does, it may remain silent because it doesn’t really have any good remediation options.  It’s a tough situation on both sides because there are no easy wands that anyone can wave to fix this.

If you think you should stop reading here because you’re only at year two of your vesting, don’t.  If you resign (and/or get fired) from your job your stock options will typically expire in just 90 days, so you’ll be facing these same issues — just on a greatly shortened timeframe.

Who Is The Evil Genius Who Set This Up?
None.  There is no evil genius.  It’s simply an unwelcome artifact of Silicon Valley history.  In olden days it took about 4 years for a startup to hit a liquidity event [4] [5].  That’s why stock options vest over 4 years.  It’s also why they expire after 10 years.  All options need to have an expiration date and back in the day, 10 years approximated infinity [6].

As employees, we benefit from the artifact of 4-year-vesting.  However, if we’re not paying attention, we can get crushed by the artifact of 10-year expiration.

What Can I Do About It?
First, this is a tough situation and you may have few or no good options.

Second, I’m not a financial advisor [7]; you’ll need to see your financial and/or tax advisors to figure this out.  In this post, I’ll walk through what I see as some of your options – which will itself demonstrate the problem.

Third, short timeframes are not your friend.  If you see this problem coming I recommend you start thinking hard about it at least 12 months in advance; when you’re down to 30 days left your available choices may be extremely limited.

Here are some of your available options for handling this situation.

1. Exercise the stock-option before it expires. You’ll need to find $40K to pay the company for the exercise, but that’s not the hard part.  Because the fair market value (FMV) of the stock is $10/share you’re going to face a tax bill of somewhere between $1.1M and $1.9M on the exercise, even if you hold the stock (i.e., you don’t sell it) [8].  This is, in fact, the problem statement.

2. Exercise the option before it expires and sell enough to a third-party to pay the tax bill. This means, if you’re selling in the private market (e.g., EquityZen, Sharespost) at the FMV of $10, that you exercise 400K shares and then sell about 150K of them to cover your tax bill [9] [10A].  That leaves you holding 250K shares of stock.  This, however, requires (a) the existence of such a market and/or your ability to independently find a buyer, (b) the stock to be not restricted from you selling it without company approval (or the company granting such approval), and (c) you paying I’d guess $10K or more in legal and/or other transaction fees to make it happen [10].

3. Exercise the option with the support of a specialist fund (e.g,. ESOfund) that cuts rather exotic deals to solve this and related problems [10A]. For example, one of these (typically very boutique) funds might say:  “I’ll give you the cash both for the exercise and to pay your tax bill, if you give me the shares.  When we eventually sell them, I’ll keep 100% of proceeds until I get my money back, 50% until I get 3x my money back, and 25% after that [11].”  These funds are hard to find and the deals can be very hard to understand.  Legal bills can rack up quickly.  And you’ll need to be a major shareholder; no one wants to do a lot of complex work for 2K shares. 

4. Use a company liquidity program, if offered, to avoid getting into the situation.  Some companies periodically offer employees the right to sell shares in order to demonstrate to everyone that liquidity is possible.  Don’t be so busy doing your job that you forget to consider these programs.  While you may think the valuations offered are too low, if there is no secondary market for the stock and/or the company restricts selling the stock after its purchase, you may have no choice but to use such a program.  It’s a far better deal than letting the options expire worthless.

5. Live in Belgium. I believe Belgium has a great law whereby you pay a modest tax at the time you receive a stock option grant and then no tax on either exercise or sale [12].  I’m telling you this not to encourage you to start learning to enjoy moules frites and making immediate plans to move to Brussels (it’s probably too late) — but to remind my international readers that I’m writing from a US point of view and that stock option taxation, in particular, varies a lot from country to country.  If you happen to live in Belgium and the law hasn’t changed, it’s a particularly good place to get stock-options in early-stage startups.   But the main point is to be sure you understand the law of your country before making any plans or decisions when it comes to stock options (or any other tax matter).

6. Avoid the problem in the first place via an early-exercise with section 83b election. Some companies will allow you to exercise your options before they vest by effectively reversing the stock option – you pay the exercise price, the company gives you the shares, and the company retains a right to buy back the shares from you (at the exercise price) which declines by 1/48th per month over four years.  In addition, if you file a section 83b election within 30 days (and the grant was not in-the-money) then you pay no tax at exercise time and incur tax liability only when you eventually sell the shares, which if it’s more than a year away, results in long-term capital gains tax treatment [13].  Wow, this sounds awesome – and it is.

What’s the downside?  (a) Ideally, you need to do this up-front so it’s not necessarily a good solution if you’re in year three, (b) you need enough money to pay the exercise price which typically works well at early-stage startups (400K shares at $0.01/share = $4K) and a lot less well at later stage ones (100K shares at $5/share = $500K), (c) if the company gets in trouble [14] your common stock could well end up worthless and you won’t get your money back – you are effectively destroying the option-value of your option by exercising it, (d) if you don’t file your section 83b in a timely manner and/or lose your records of having filed it you could end up in a very bad position tax-wise [15].

7. Mitigate the problem via regular exercises along the way (laddered). While I don’t think this is a great strategy, it’s simple to understand, and mixes preserving option value while periodically exercising (and incurring taxes) along the way – so it’s going to be expensive to execute; but nevertheless way less expensive than a forced exercise in year 10.  The two nice things about this strategy are (a) you shouldn’t need company approval to execute it and (b) you can stop along the way and still own some of your options — it only gets very expensive in years 3 and 4.  Here’s a spreadsheet to show it (including some comments not in the image below) which you can download here.

ladder vs. panic

Of course, you may find other strategies, proactive companies may offer programs with other strategies, you might be able to execute a derivative of one of these strategies (e.g., number 3 with a rich uncle), and you can combine the above strategies (e.g., laddering plus early-exercise) as you see and your financial and tax advisors see fit.

I should note that later-stage startups may offer restricted stock units (RSUs) instead of options.  Though some of the same principles can apply (e.g., section 83b elections also relate to RSUs), RSUs work differently than stock options and bring different complexity which is beyond our current scope.

In this post, I’ve alerted you to the ten-year stock option expiration trap and given you a few ideas on how to avoid it.  Moreover, remember that if you resign (or get terminated) that this distant ten-year expiration problem becomes a 90-day problem.  Finally, I’ll point you to my favorite book on this subject (which covers both stock-options and RSUs), Consider Your Options 2019, and which has a nice website as well.

Remember to always talk to your financial and tax advisors before making key decisions about equity-based compensation.

# # #

Notes

[1]  Most private startups get an annual 409a valuation once a year to establish the fair market value (FMV) of their common stock so they can appropriately set the strike price on newly granted stock options, without being accused of granting in-the-money options (as some companies were accused of doing during the dot-com bubble).  409a valuations are always lower than “headline valuations” that companies often announce as part of financing rounds, because headline valuations take the price of a newly issued preferred share and multiply it by the entire share pool (common and preferred).  409a valuations first value the business overall, then subtract any debt, and then subtract the value of “preference stack” in arriving at a value for common stock in aggregate, and then per-share.  Because (a) of how they are calculated, (b) various valuation methodologies produce ranges, and (c) there is a general desire to preserve a low common stock price for as long as possible, 409a valuations not only differ from headline valuations (which are arguably calculated incorrectly) but they tend to produce a low-side estimate for the value of the common.

[2] And maybe a lot more than that because many private, hot-company stocks sometimes trade well above the 409a value in secondary markets.  In fact, in many cases it trades a little or no discount to the price of the last preferred round, and in some cases above it which, unless a lot of time has passed since the last round, strikes me as kind of crazy.

[3] That is, in the 45 days after August 15, 2019 – the day I wrote the post.

[4] For example, Business Objects was founded in 1990 and went public in 1994.

[5] If Silicon Valley were reinvented today, options would probably vest over 12 years, because that’s about how long it takes to get to an IPO.  However, that’s unlikely to happen as the ten years is the maximum duration under law for an ISO option.  This isn’t a VC-change kind of thing; it’s a write your Congressional Representative sort of thing.

[6] The definition of a (call) stock option is the right to buy N shares at price P by date D.  Expiration dates are inherent to options.

[7] See disclaimers in my FAQ and terms of use.

[8] Math is approximate.  On the low side, I’m assuming it’s an ISO option and the tax is all AMT at 28% and you’re in a tax-free state.  On the high side, I’m assuming it’s an NQ option, and a combined marginal rate of 49%.  See your tax professional for your situation.  The main point here:  it can be a huge number.

[9] Bear in mind, per earlier comments, the FMV tends to run on the low side and particularly for red-hot companies, prices in the secondary market can be well above the FMV, e.g., in this case, let’s say $20.  While this will help you on the sale side (you’ll need to sell half as many shares), it could bite you on the tax calculation because you’ll simultaneously be arguing that the stock is worth $10 for tax calculation purposes while actually selling it for $20.  See your tax professional.  Good luck.

[10] I’ve seen and/or heard of cases where companies charge a $5K administrative fee for people selling shares in this manner.  Some companies like it and make it easy.  Some don’t and make it anywhere from hard to impossible.

[10A] There is zero endorsement of any vendor or fund mentioned here.  I provide examples simply to make things concrete in terms of classification.

[11] This is a somewhat flawed representation of such deals, but you get the idea.  The fund effectively becomes your partner in owning the stock.  These can be expensive deals, but for the stock-optionee some value is better than none, which is what they will have once the option expires.

[12] This works particularly well for early-stage startups because I believe you pay a tax of either 9% or 18% of the aggregate value (shares x strike price) of the option at grant time, and the shares are worth next to nothing.  (It works less well if you get a grant of 100K shares valued at $100/share.)

[13] You must, must, must see your tax advisor on this.  You have only 30 days to file an election and if you don’t, you lose the benefits of this approach and can put yourself in a very bad situation.

[14] And trouble doesn’t have to mean bankruptcy.  It simply means any situation where the sale price of the company is less than the sum of debt to be repaid plus the preference stack.  In these situations, the common stock becomes worthless.  Note to the wise:  while it’s often the case, you cannot assume the preference stack is simply the amount VCs have invested in preferred stock.  In some cases, you have multiple liquidation preferences where VCs (or PEs) get 1.5x to 2.0x their investment back before the common gets anything.

[15] See [13].   I won’t go into the details of what happens because it’s complicated, but if you are going to go the section 83b route, you need to file within 30 days and keep very good records that you did.  You remember when people went bankrupt on AMT taxes due to buying-and-holding ISO options in Bubble 1.0?  You could end up rekt in a similar way if you get this wrong.

Good CEO Habits: Proactively Update Your Board at the End of Every Quarter

I am surprised by how many startup CEOs leave the board hanging at the end of the quarter.  As a CEO my rule of thumb was that if a board member ever asked me about the quarter then I’d failed in being sufficiently proactive in communications.  In tight quarters I’d send a revised forecast about a week before the end of the quarter — hoping to pre-empt a lot of “how’s it going” pings.

And every quarter I would send an update within 24 hours of the quarter-end.  In fact, if we’d effectively closed-out all material opportunities before quarter-end, I’d send it out before the quarter was technically even over.

Why should you do this?

  • It’s a good habit.  Nobody wants to wait 3 weeks until the post-quarter board meeting to know what happened.
  • It shows discipline.  I think boards like disciplined CEOs (and CFOs) who run companies where the trains run on time.
  • It pre-empts one-of emails and phone calls.  It’s probably less work, not more, to send a quick standard end-of-quarter update that includes what you do know (e.g., bookings) but not what you don’t (e.g., expenses because accounting hasn’t closed the quarter yet).

What form should this update take?  I’d start with the board sales forecast template that I’ve already written about here.  (And I’d change Forecast to Actual and drop the Best Case and Pipeline Analysis.)

how-to-present-forecast-2.jpg

Since cash is oxygen at a start-up, I’d add a line about forecast cash flows, making sure they know the numbers are preliminary, with final numbers to follow at the upcoming board meeting.  I might add a little color on the quarter as well.

Here’s an example of a good end-of-quarter board update.

Dear Board,

Just a quick note to give you an update on the quarter at GreatCo.  We beat new ARR plan by $200K (landing at $1,700K vs. plan of $1,500K) and grew new ARR YoY by 42%.  We came in slightly under on churn ARR, landing at $175K vs. a plan of $200K.  The result is we ended the quarter $225K ahead of plan on ending ARR at $11,546K, with YoY growth of 58%.

Cash burn from operations is preliminarily forecast to be $240K ahead of plan at $2,250K and ending cash is just about at-plan of $10,125K (we were a little behind in 1Q and 2Q has caught us back up).

We had some great competitive wins against BadCo and WorseCo — I’m particularly happy to report that we won the Alpha Systems deal (that we discussed in detail at the last meeting) against BadCo for $275K.  Sarah will tell us how we turned that one around at the upcoming board meeting.

Finally, I did want to point out — given the concerns about sales hiring — that we ended the quarter with 12 quota-carrying reps (QCRs), only 1 behind plan. Sarah and Marty did a great job helping us catch almost all the way back up to plan.  That said, we’re still having trouble hiring machine-learning engineers and are nearly 5 heads behind plan to-date.  Ron and Marty will update the board on our plans to fix that at the meeting.

Overall, we feel great about the quarter and I look forward to seeing everyone in a few weeks.  Thanks, as always, for your support.

[Table with Numbers]

Cheers/Dave

# # #

Stopping Inception Churn: The Prospective Customer Success Review

I think for many sales-aggressive enterprise SaaS startups, a fair amount of churn actually happens at inception.  For example, back in 2013, shortly after I joined Host Analytics, I discovered that there were a number of deals that sales had signed with customers that our professional services (PS) team had flat out refused to implement.  (Huh?)  Sales being sales, they found partners willing to do the implementations and simply rode over the objections of our quite qualified PS team.

When I asked our generally sales-supportive PS team why they refused to do these implementations, they said, “because there was a 0% chance that the customer could be successful.”  And they, of course, were right.  100% of those customers failed in implementation and 100% of them churned.

I call this “inception churn,” because it’s churn that’s effectively built-in from inception — the customer is sent, along with a partner, on a doomed journey to solve a problem that the system was never designed to solve.  Sales may be in optimistic denial.  Pre-sales consulting knows deep down that there’s a problem, but doesn’t want to admit it — after all, they usually work in the Sales team. Professional services can see the upcoming trainwreck but doesn’t know how to stop it so they are either forced to try and catch the falling anvil or, better yet, duck out and a let partner — particularly a new one who doesn’t know any better — try to do so themselves.

In startups that are largely driven by short-term, sales-oriented metrics, there will always be the temptation to take a high-risk deal today, live to fight another day, and hope that someone can make it work before it renews.  This problem is compounded when customers sign two- or three-year deals [1] because the eventual day of reckoning is pushed into the distant future, perhaps beyond the mean survival expectation of the chief revenue officer (CRO) [2].

Quality startups simply cannot allow these deals to happen:

  • They burn money because you don’t earn back your CAC.  If your customer acquisition cost ratio is 1.5 and your gross margins are 75%, it takes you two years simply to breakeven on the cost of sale.  When a 100-unit customer fails to renew after one year, you spent 175 units [3], receive 100 units, and thus have lost 75 units on the transaction — not even looking at G&A costs.
  • They burn money in professional services.  Let’s say your PS can’t refuse to the implementation.  You take a 100-unit customer, sell them 75 units of PS to do the implementation, probably spend 150 units of PS trying to get the doomed project to succeed, eventually fail, and lose another 75 units in PS.  (And that’s only if they actually pay you for the first 75.)  So on a 100-unit sale, you are now down 150 to 225 units.
  • They destroy your reputation in the market. SaaS startup markets are small.  Even if the eventual TAM is large, the early market is small in the sense that you are probably selling to a close-knit group of professionals, all in the same geography, all doing the same job.  They read the same blogs.  They talk to the same analysts and consultants.  They meet each other at periodic conferences and cocktail parties.  You burn one of these people and they’re going to tell their friends — either via these old-school methods over drinks or via more modern methods such as social media platforms (e.g., Twitter) or software review sites (e.g., G2).
  • They burn out your professional services and customer success teams. Your PS consultants get burned out trying to make the system do something they know it wasn’t designed to do.  Your customer success managers (CSMs) get tired of being handed customers who are DOA (dead on arrival) where there’s virtually zero chance of avoiding churn.
  • They wreck your SaaS metrics and put future financings in danger. These deals drive up your churn rate, reduce your expansion rate, and reduce your customer lifetime value.  If you mix enough of them into an otherwise-healthy SaaS business, it starts looking sick real fast.

So what can we do about all this?  Clearly, some sort of check-and-balance is needed, but what?

  • Pay salespeople on the renewal, so they care if the customer is successful?  Maybe this could work, but most companies want to keep salespeople focused on new sales.
  • Pay the CRO on renewal, so he/she keeps an honest eye on sales and sales management?  This might help, but again, if a CRO is missing new sales targets, he/she is probably in a lot more trouble than missing renewals — especially if he/she can pin the renewal failures on the product, professional services, or partners.
  • Separate the CRO and CCO (Chief Customer Officer) jobs as two independent direct reports to the CEO.  I am a big believer in this because now you have a powerful, independent voice representing customer success and renewals outside of the sales team.  This is a great structure, but it only tells you about the problems after, sometimes quarters or years after, they occur.  You need a process that tells you about them before they occur.

The Prospective Customer Success Review Committee
Detecting and stopping inception churn is hard, because there is so much pressure on new sales in startups and I’m proposing to literally create the normally fictitious “sales prevention team” — which is how sales sometimes refers to corporate in general, making corporate the butt of many jokes.  More precisely, however, I’m saying to create the bad sales prevention team.

To do so, I’m taking an idea from Japanese manufacturing, the Andon Cord, and attaching a committee to it [4].  The Andon Cord is a cord that runs the length of an assembly line that gives the power to anyone working along the line to stop it in order to address problems.  If you see a car where the dashboard is not properly installed, rather than letting it just move down the line, you can pull the cord, stop the line, and get the problem fixed upstream, rather than hoping QA finds it later or shipping a defective product to a customer.

To prevent inception churn, we need two things:

  • A group of people who can look holistically at a high-risk deal and decide if it’s worth taking.  I call that group the Prospective Customer Success Review Committee (the PCSRC).  It should have high-level members from sales, presales, professional services, customer success, and finance.
  • And a means of flagging a deal for review by that committee — that’s the Andon Cord idea.  You need to let everyone who works on deals know that there is a mechanism (e.g., an email list, a field in SFDC) by which they can flag a deal for PCSRC review.  Your typical flaggers will be in either pre-sales or post-sales consulting.

I know there are lots of potential problems with this.  The committee might fail to do its job and yield to pressure to always say yes.  Worse, sales can start to punish those who flag deals such that suspect deals are never flagged and/or that people feel they need an anonymous way to flag them [5].  But these are manageable problems in a healthy culture.

Moreover, simply calling the group together to talk about high-risk deals has two, potentially non-obvious, benefits:

  • In some cases, lower risk alternatives can be proposed and presented back to the customer, to get the deal more into the known success envelope.
  • In other cases, sales will simply stop working on bad deals early, knowing that they’ll likely end up in the PCSRC.  In many ways, I think this the actual success metric — the number of deals that we not only didn’t sign, but where we stopped work early, because we knew the customer had little to no chance of success.

I don’t claim to have either fully deployed or been 100% successful with this concept.  I do know we made great strides in reducing inception churn at Host and I think this was part of it.  But I’m also happy to hear your ideas on either approaching the problem from scratch and/or improving on the basic framework I’ve started here.

# # #

Notes

[1] Especially if they are prepaid.

[2] If CROs last on average only 19 to 26 months, then how much does a potentially struggling CRO actually care about a high-risk deal that’s going to renew in 24 months?

[3] 150 units in S&M to acquire them and 25 units in cost of goods sold to support their operations.

[4] I can’t claim to have gotten this idea working at more than 30-40% at Host.  For example, I’m pretty sure you could find people at the company who didn’t know about the PCSR committee or the Andon Cord idea; i.e., we never got it fully ingrained.  However, we did have success in reducing inception churn and I’m a believer that success in such matters is subtle.  We shouldn’t measure success by how many deals we reject at the meeting, but instead by how much we reduce inception churn by not signing deals that we never should have been signed.

[5] Anonymous can work if it needs to.  But I hope in your company it wouldn’t be required.

Career Decisions: What To Look For In a Software Startup

So, you’re thinking of taking a job at a startup, but are nervous about the risk, perhaps having trouble telling one from another, and unsure about knowing what’s really important in startup success.  In this post, I’ll share what I consider to be a great checklist for CXO and VP-level positions, which we’ll try to adapt a bit to be useful for all positions.

1. Great core/founding team.  Startups are about people.  We live in a founder-friendly VC era.  Thus, there is a good chance one or all of the founding team will be around, and in influential positions, for a long time.  If you’re CXO/VP-level, make sure you spend time with this team during your interviews [1] and make sure you think they are “good people” who you trust and who you’d want to work with for a long time [2].  You might well be doing so.

2. Strong investors.  In venture capital (VC) land, you should view investors as long-term partners in value creation.  Their investments give them contractual rights (e.g., board seats) and you can assume they will be around for a long time [3].  Companies need two things from their investors:  advice (e.g., the wisdom acquired from having built a dozen companies before) and money.  While good advice is always important, money is absolutely critical in today’s startup environment where a hot category can quickly evolve into a financial arms race to see which company can “buy” the most customers the fastest [4].

While I won’t do a tiering of Silicon Valley VCs here, you want to see investors with both deep pockets who can fund the company through thick (e.g., an arms race) and thin (e.g., inside rounds) and strong reputations such that other VCs are willing and eager to invest behind them in future rounds [5].

3. Newer company/technology.  I’ll give you the hint now that this is basically a list of key factors ranked by difficulty-to-change in decreasing order.  So the third hardest-to-change key factor is technology.  If you’re considering going to work at a twelve-year-old startup [6], understand that it’s very likely built on twelve-year-old technology premised on a twelve-plus-year-old architecture.  While the sales-and-marketing types will emphasize “its proven-ness” you will want to know how much technical debt there is associated with this old architecture.

Great startups are lead by strong technologists who ensure that technical debt is continuously addressed and retired via, e.g., trust releases.  Bad startups are feature addicts who pile feature upon feature atop a deteriorating architecture, creating an Augean Stables of technical debt. But even in good startups, routine debt-retirement doesn’t prevent the need for periodic re-architecture.  The best way to avoid an architectural mess of either type is to go to a newer startup, led by strong technologists, where the product is most probably built atop a modern architecture and where they definitionally cannot have accumulated a mass of technical debt [7].  

4. Clean cap table.  I once took a job at a company where a VC friend of mine said, “they have a good business, but a bad cap table.”  Since I didn’t entirely understand what he meant at the time, I took the job anyway — but, wow, do I wish I’d spent more time trying to understand the phrase “bad cap table.”

A capitalization table (aka “cap table”) is simply a list of investors, the type and amount of shares they hold, shares held by founders, shares allocated to the stock option pool, warrants held by suppliers and/or debtholders, and along with information about any debt the company has acquired.  So, strictly speaking, how could this table be inherently good or bad?   It just “is.”  Nope.  There are good cap tables and bad cap tables and here’s a partial list of things that can make a cap table bad in the eyes of a future investor.

  • Upstream investors who they don’t know and/or don’t want to work with.  That is, who holds the shares matters.
  • Ownership division that gives either the founders or employees too few shares.  Most VCs have the right to retain their percentage ownership going forward so if the company is already 60% owned by VC1 after the Series A and 20% owned by VC2 after the Series B, the new investor may believe that there simply isn’t enough to go around.  Strong VCs truly believe in founder and employee ownership and if there isn’t enough of it, they may walk from a deal.
  • ARR not commensurate with total funding.  Say a company has consumed $50M in capital but has only $5M in ARR to show for it.  Barring cases with exceptional product development entry barriers, that’s not a great ratio and most likely the result of a pivot, where the company started out on hypothesis A and then moved to hypothesis B.  From the new investor’s perspective, the company spent (and wasted) $30M on hypothesis A before switching to hypothesis B and thus has invested only $20M in its current business.  While some new investors might invest anyway, others would want some sort of recapitalization to reflect the business reality before investing.
  • Parasites, such as departed founders or incubators.  Founders A and B, aren’t going to be that excited over the long term for making money for founder C while she is off doing a new startup.  And why would a future VC want to make money for founder C, when she has already left the company [8]?  These are problems that need to be addressed from the viewpoint of a new investor.
  • Network effects among investors.  If VC1 owns 40% and VC2 owns 20% and VC2 works almost exclusively with VC1, then you can assume VC1 has control of the company.   This may not be a deal killer, but it may make a new investor wary.
  • Undesirable structure.  While VCs almost always buy preferred shares (as opposed to the common shares typically held by founders and employees), the specific preferences can vary.  New VC investors typically don’t like structure that gives preferred shares unusual preferences over the common because they worry it can demotivate employees and founders.  Such structure includes participating preferencesmultiple liquidation preferences, and redemption rights.

And that’s only a partial list.  At the CXO level, I think you have the right to ask about the cap table, but it’s much harder for job titles below that.  So I understand that you won’t always be able to access this information, but here’s what you can do:  (1) look at Crunchbase for financial history to try and identify some of these problems yourself, and (2) try to find a VC friend and get his/her opinion on the company.  VCs, particularly those at the bigger firms, are remarkably well informed and look at lots of deals, so they can usually give you an inkling about potential problems.

5. Strong market opportunity.  I’ve always done best when the need for the product was obvious.  Best example:  Business Objects in the 1990s — data warehouses were being built and it was obvious that there were no good tools to access them.  Business Objects eventually sold for nearly $7B.  Best counter-example:  MarkLogic in the 2000s — several years after Gartner wrote a note called XML DBMS:  The Market That Never Was.  That nearly twenty-year-old company is still not liquid, though through exceptional execution it has built a nice business despite strong headwinds; but there was nothing either obvious or easy about it.  In my other direct experience, the markets for Ingres (RDBMS), Salesforce.com, and Host Analytics (cloud EPM) were obvious.  The market for Versant (ODBMS) was not.

Another test you can apply to the market is the Market Attractiveness Matrix, which positions the type of buyer vs. the need for the product.  Selling SFA to sales, e.g., would be in the most attractive category while selling soft productivity improvement tools to HR would be in the least.

mam

Finally, I also like markets where the pricing is tied to something that inherently goes up each year (e.g., number of salespeople, size of stored documents, potentially usage) as opposed to things that don’t (e.g., number of HR or FP&A people, which increases — but in a more logarithmic fashion).

6. Strongest competitor in the market.  The problem with obvious market opportunities, of course, is that they attract multiple competitors.  Thus, if you are going to enter a competitive market you want to ensure the company you’re joining is the leader in either the overall market or a specific segment of it.  Given the increasing returns of market leadership, it is quite difficult to take away first place from a leader without they themselves faltering.  Given that hope is not a strategy [9], unless a runner-up has a credible and clear plan to be first in something [10], you should avoid working at runner-up vendors.  See the note below for thoughts on how this relates to Blue Ocean Strategy [11].

7.  Known problems that you know how to fix.  I’ve worked at epic companies (e.g., Business Objects, Salesforce) and I’ve worked at strugglers that nearly clipped the tree-tops on cash (e.g., Versant) and I can assure you that all companies have problems.  That’s not the question.  The questions are (1) do they get what really matters right (see previous criteria) and (2) are the things that they get wrong both relatively easy to fix and do you know how to fix them?

Any CXO- or VP-level executive has a set of strengths that they bring to their domain and the question is less “how good are you” than “does the company need what you bring?”  For example, you wouldn’t want a sales-and-marketing CEO — no matter how good — running a company that needs a product turnaround.  The key here is to realistically match what the company (or functional department) needs relative to what you can bring.  If you’re not a CXO- or VP-level executive, you can still apply the same test — does the company’s overall and functional leadership bring what the company needs for its next level of evolution?

8. Cultural compatibility.  Sometimes you will find a great organization that meets all these criteria but, for some reason, you feel that you don’t fit in.  If that happens, I’d not pursue the opportunity because you are likely to both be miserable on a daily basis and not succeed.  Culture runs deep in both people and in companies and when it’s a not a fit, it’s very hard to fake it.  My favorite, well-documented example of this was Dan Lyons at HubSpot, detailed in his book Disrupted.  HubSpot is a great company and I’m pretty sure Dan is a great guy, but wow there was a poor fit [12].  My advice here is to go with your gut and if something feels off even when everything else is on, you should listen to it.

I know it’s very hard to find companies that meet all of these criteria, but if and when you find one, I’d jump in with both feet.  In other cases, you may need to make trade-offs, but make sure you understand them so you can go in eyes wide open.

# # #

Notes

[1] A lack of desire to spend time with you during the recruiting process should be seen as a yellow/red flag — either about you as a candidate or their perceived importance of the position.

[2] In this context, “a long time” means 5-10 years.  The mean age of high-growth SaaS IPO companies in last year’s IPO class was 14 years.

[3] While “shareholder rotations” are possible (e.g., where firm B buys out firms A’s position) they are pretty rare and typically only happen in older companies (e.g., 10 years+).

[4] In my opinion, VC a few decades back looked more like, “let’s each back 5 companies with $20M and let the best operators win” whereas today it looks more like, “let’s capitalize early and heavily on the increasing-returns effects of market leadership and stuff (i.e., foie-gras) our startups with money, knowing that the market winners will likely be those who have raised the most cash.”  Note that while there is debate about whether this strategy yields the best returns (see foie gras link), there is less debate about whether this generates large companies in the market-leader pack.

[5] As one later stage investor told me:  “we prefer to work with syndicates with whom we’ve worked before” suggesting larger firms with more deals are preferable upstream and “if it ends up not working out, we’d much rather be in the deal with a highly respected firm like Sequoia, Accel, Lightspeed, or A16Z than a firm no one has ever heard of.”  Your upstream investors have a big impact on who is willing to invest downstream.

[6] Quip:  what do you call a twelve-year-old startup?  Answer:  a small business.  (Unless, of course, it’s high-growth and within striking distance of an IPO.)

[7] I would argue, generally, that newer startups tend to be built with newer business model assumptions as well.  So picking a newer company tends to ensure both modern architecture and contemporary thought on the business model.  For example, it’s hard to find a five-year-old enterprise software company built on an on-premises, perpetual license business model.

[8] Or, if an incubator makes itself a virtual cofounder in terms of common stock holdings in return for its incubation services.

[9] i.e., hoping the other company screws up.

[10] Either a segment or a segment that they believe will grow larger than today’s overall market.

[11] I feel obliged to mention that not all non-obvious market opportunities are bad.  As a big fan of Blue Ocean Strategy, I’d argue that the best market opportunities are semi-obvious — i.e., obvious enough that once you dig deeper and understand the story that they are attractive, but not so obvious that they attract a dozen ocean-reddening competitors.  Of recent enterprise software companies, I’d say Anaplan is the best example of Blue Ocean Strategy via its (emergent) strategy to take classic financial planning technology (hypercubes) and focus on sales planning in its early years.

[12] Note that I am not saying HubSpot is a perfect company and we can argue at great length (or more likely, quite briefly) about the strengths and weaknesses in typical Silicon Valley cultures.  And that’s all interesting academic debate about how things should be.  What I am saying is that when it comes to you, personally, for a job, why make yourself miserable by joining an organization where you know up-front that you don’t fit in?