Author Archives: SMS

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Playing Basket Ball In Outer Space

Reading Time: 7 minutes

“Investors and founders have adopted a seize-the-day mentality, believing the pandemic created a once-in-a-lifetime opportunity to shake things up.” – ‘It’s All Just Wild’: Tech Start-Ups Reach a New Peak of Froth

The concept of this article has been sitting on my list for over a year.  Mostly because there is a high likelihood that the article, in writing, turns out to not be as good as the article as it sits in my head.

“When you are a Bear of Very Little Brain, and you Think of Things, you find sometimes that a Thing which seemed very Thingish inside you is quite different when it gets out into the open and has other people looking at it.” — Winnie the Pooh

I am going to try my best to put some thoughts down, and it seems like the tide is shifting in the markets (see the Fifth SaaS Correction).  We might just be in the early days of reversing some “irrational exuberance” that has built up in the marketplace over quite a few years (see Private Equity’s Love Affair with Software Companies and Meet Private Equity’s King of SaaS).

It has been an interesting challenge to help guide a cloud-based, software as a service (SaaS) company, as its finance leader, as the normal bounds of financial rationality got blurry due to the growth-at-all-costs valuation mindset.  Sort of akin to trying to teach someone to play basketball in outer space, where gravity is basically zero, and normal actions, like jumping and dribbling, are unconstrained.  Why would you dribble or pass the ball, when you can float the entire length of the court?  The biggest challenge is not getting tangled up in the lights attached to the roof of gymnasium.

Here are some examples, where traditional decision-making is challenged, when attempting to analyze a growth-at-all-costs situation with a traditional financial framework:

  1. How should we think about pricing optimization?  Lost deals carry a huge opportunity cost vs. small price increases.
  2. How should we price software and services?  No one seems to care about services, except the auditors since services do not generate ARR, so that is going to drive some decision making and incentive plan design.
  3. What are the margins on services?  Why bother with this boring and antiquated view of things.
  4. Should we care about the efficiency of internal operations?  That seems like a distraction; we should focus on growing ARR.
  5. Which parts of the business should we invest in?  Clearly those that produce new ARR, at the expense of virtually everything else.
  6. How should we think about investments in infrastructure, security, compliance, etc.?  Has it cost us any ARR yet?  
  7. How should sales commissions be structured?  Theoretically, a sale is worth 10x+ ARR on the deal.  Are you really going to pay more than the first year of the deal is worth to the sales rep, etc.  Seems irrational, but the valuation math indicates maybe you should.
  8. What is an acceptable Customer Acquisition Cost?  This is basically the same question – but adding in other broader sales & marketing costs.  And if marketing spend is generating leads and leading to closed deals, the answer approaches an unbounded solution.
  9. How much should we invest in launching a new module or product?  Well, as long as the cost is below 10x+ the future ARR, I guess we should go for it.  Let’s ignore the fact that the cash flow from the new product won’t cover development costs for…[insert optimistic assumption]…years.  Hell, why even build a financial model anyway.
  10. How should you respond to customer issues?  Well, the math says protect ARR at all costs. 
  11. What if more growth makes your valuation on ARR go up?  Oh crap, the model went circular and unbounded.  Better break out Solver.

This is certainly not an exhaustive list, but should serve as some insight into the challenges of managing one of these businesses in this environment.  To be fair, this is not entirely a valuation driven problem.  The economics of software businesses play a role too.  When marginal costs are close to zero and the gross margins of a business are 80%+, there are few “bad” customers or “unprofitable” products.  

I am an engineer by training.  I believe that trade-offs exist in every decision.  And, that is healthy.  Under the current valuation regime, there has been a dearth of trade-offs.  

So, as the valuation pendulum swings from growth only metrics, back toward more dreary metrics (cash flow and return on invested capital), expect some issues to arise.  Just like an astronaut returning from a long stint at the International Space Station, getting used to gravity may take some time.

Over the last number of years, investors and managers of software businesses have been making decisions under this valuation framework revolving around ARR valuations and growth.  That has likely led to some choices that will look less robust in a different valuation paradigm. It will take some time to uncover and unwind those.  It might take even longer to change the mindset of those investors and managers, if that can even be done.  In the dotcom era, there were few pivots.  Many of those businesses could not or would not change their models, and you know how those ended.

Every situation is unique, but here is a real life case study – from Freshworks – a member of the IPO class of 2021.  I think you will look back on this and see they timed this one pretty well.

“We believe that we are early in addressing our large market opportunity and we intend to continue to make investments to support the growth and expansion of our business. We have a track record of bringing new products to market and scaling these new products over time. As of December 31, 2021, we have two primary products with over $100 million in ARR, Freshdesk and Freshservice.” – 10K

Highlighting is mine.  Revenue up year over year ~$121 million; costs up ~$270 million.  Sales & Marketing costs up ~$127 million alone.  So, yes, I would hope that you believe there is a large market opportunity to capture.  The real question is does this business model work, if you care about something other than top line growth?  

The cash flow picture is not good.

Large market opportunity, high growth, but not currently monetizing any of that well.

And, that is the question I wrestle with the most. When is the operating leverage and cash flow going to show up in these businesses, if ever?  How is the switch going to get flipped? 

There’s a large market opportunity.  Ok, good.  The business is growing at a high rate.  That’s great.  But operating leverage is nowhere to be seen, since you are plowing most of the cash flow back into the business – mostly into commercial operations to generate that growth (separate topic: be careful around the assumptions about steady-state cash flow in a growing subscription business – it may not be what you think it is – as it can be distorted by customers paying invoices upfront).  When sales & marketing spend essentially equals gross profit, what is the point?

What is the catalyst that causes the managers of the business to turn off all that sales & marketing spend to increase profitability?  Why would they ever do when slower growth would likely crush the valuation (of their stock options)?   But at these valuations, the cash flow of the business would take decades to cover the acquisition cost of the business.  You Cannot Eat Growth.  This feels like a never ending cycle; until the cycle is ended by exogenous forces. In the dotcom days, the cycle was ended by running out of cash one day.

I found this funny commentary on the situation:

“If you’re curious about where all the billions of dollars of venture and IPO capital are being spent by all these Software as a Service startups, I have figured it out. The answer is in my inbox. Every day five spam emails about signing up for this enterprise software or that – control your employees’ spending, track your employees’ benefits, a million different versions of PEO, etc. They’re basically taking all this money, divvying it up into $85,000 starting salaries and paying saleskids one year out of college to hit small business owners on LinkedIn or try to guess at the email addresses of people like me. It’s cold calling but lazier.” – Reformed Broker

A common way to think about these businesses is the “Rule of 40”.  In the Rule of 40 (https://www.thesaascfo.com/rule-of-40-saas/), managers are supposed to try to keep the sum of year over year ARR growth + EBITDA margin at or above 40.  The result is that faster growing businesses can be less profitable, while businesses that see slowing growing should prioritize profitability. Although even that is getting bastardized (i.e., see Weighted Rule of 40).  A concern I have here is with these recurring revenue business, the income statement benefits / suffers from a huge accounting effects vs. cash flow (see EBITDA Is Not A Good Proxy For Cash Flow ).  Many items, like revenue and contract expenses, are recognized over years, making the income statement less responsive (i.e., misleading) to current events.

The winner takes all?  Yes, I guess this is a fair point to raise.  Cloud-based software is disrupting the landscape. 

“It’s also interesting just how long this can take. If you live in Silicon Valley, it would be natural to think that cloud and SaaS are old and done and boring, but this chart from Goldman Sachs, showing a survey of big company CIOs, suggests that less than a quarter of their workflows are in the cloud so far, and they’re moving slower than they expected.” – Benedict Evans

 And we could be in the early days of cloud disruption – if it really is a disruption.

However, winner takes all means that only a handful of companies will grow into these valuations.  Some companies will be worth it.  But, the average cloud-based software company likely will not be the winner taking all, according to the definition of average.  So, the situation becomes similar to the investment profile for venture capital – one of your portfolio of ten might be a blockbuster; the remaining nine will likely lead to mediocre returns or even losses.  These companies become moonshots.

That might produce acceptable returns if you have a portfolio of these companies.  Which is a much different proposition than if you are managing a single business – a portfolio of one as I call it (this most definitely violates the Kelly Criterion).

I have joked in the past that I like to follow bubbles.  I worked in software and moved to San Francisco in 1999.  After graduating business school in 2005, I bought my first house and joined Wachovia’s investment banking platform eventually ending up on the Leveraged Finance team just in time to get a front row seat to the Great Financial Crisis.  So, I have a few scars.  

And like most humans, I seek to find patterns, whether they exist or not.  So take it with a grain of salt that I see a pattern here, which reminds me a lot of the business models in the dotcom days.  Where valuations were predicated on growth metrics, without much regard to the long term sustainability of the underlying business model.

This appears to be a developing situation and I will continue to watch the developments unfold with a lot of curiosity.  But the pendulum has swung pretty far in one direction over a number of years, and lots of capital has been allocated and is being managed under that paradigm, and it is likely to take some time (not a quarter) for adjustments to roll through.  In fact, my sense is that a lot of folks are still in the denial stage.

Email: How To Use Folders To Fight Bad Behaviors

Reading Time: 2 minutes

Here’s one more note on email.  See the others here:

  1. Email: Don’t Get Fired
  2. Email: Don’t Fire & Forget

There has been a lot written about strategies for dealing with email.  Admittedly, I am not that “good” at following them.  Microsoft Analytics tells me I respond too quickly.

My excuse is that at an earlier point in my career, I was tethered to my blackberry (i.e., an investment banker).  As an aside, I loved my blackberry and would seriously consider getting another one for work related mobile needs.  

I tend to check email a bit too frequently, according to the experts.  It is hard for me to ignore that little bolded Inbox icon.  Other notifications have been disabled – the pop ups, sounds, tray icons, etc.  And email rules sort out a lot of the noise – deal notifications and other system generated stuff.  But, I tend to use emails as a bit of To Do list and lean toward being action oriented, so emails still present a challenge.

The downside of not being able to ignore a new email, is I tend to respond to emails too quickly.  Too quickly meaning two things.  Too quickly as in I should think about my reply a bit more.  And too quickly as in when you send an email, you tend to get more emails.

So my solution to instill a little discipline into my bad email habits is something I stole from somewhere (maybe a modified GTD approach).  I file new emails into a few folders:

  1. Today – Items that I need to deal with today.
  2. This Week – Items that need a response in a reasonable amount of time.
  3. Next Week – Items that have a longer time horizon.
  4. Follow up – Items with no immediate action but need to be monitored.

Filing new emails let’s me accommodate my zero inbox compulsions, while avoiding firing off responses to quickly.

Reviewing these folders is part of my weekly planning process.  

Generally, I will review the Today folder toward the end of the day.  And check the This Week folder at various points throughout the week.  The Next Week folder gets reviewed on Fridays and Mondays and shuffled into either Today or This Week.

There you go.  Hopefully, that helps someone.

Influential Reads – April 2022

Reading Time: 2 minutes

“Humility is the voice inside your head that says, ‘anyone can do it once, that’s luck. Can you do it consistently?’” – Farnam Street

Apologies for being a bit quiet.  In addition to a busy work period and decamping Utah and driving cross country to Florida, we seem to be in a period of time with particularly wide error bars.  So, wait and see looks like a pretty good approach to me.  I am extremely curious as to where the world is in six months.

On the reading front, I finally finished Titan: The Life of John D. Rockefeller, Sr.  And have been attempting to clear out the always present backlog of saved articles.  More on how that works here.

Here are my most influential reads – in no particular order:

  1. No News Is Good News – ” Personally, I vote for going cold turkey and simply walking away from the whole idea of news and the illusion of staying informed.”
  2. Take that two and a half percent and run – ” I would buy the hell out of the two-year at 2.5% but not the ten-year at the equivalent yield. “
  3. Paradoxes of Life – “The most persuasive people don’t argue—they observe, listen, and ask questions.”
  4. Bonds to Buy After an ‘Epic Rout.’ – “The iShares 20+ Year Bond exchange-traded fund (ticker: TLT), which holds long-term Treasuries, is down 14% this year, against a 5% drop in the S&P 500  index. Municipal bond closed-end funds are off 15%.”
  5. The Importance of Slugging Percentage in Investing – “But what matters more is how much money those winners make compared to how much the losers lose.”
  6. A Q&A With Mary Meeker: How Tech-Trend Guru Sees the World Now – “What macro issues worry you? It’s a long list.”
  7. Is U.S. Booming or Busting? It Depends on the Data You Examine. – “Trucking activity has plunged 50% in the past 10 weeks on flat unit retail sales and already excessive inventories, according to a research note. “
  8. There Will Be No Soft Landing. Why a Recession Is Inevitable. – “The debate over where the economy is going should be recast. A soft landing at this point is wishful thinking. “
  9. What Does the Bond Market Rout Mean for the Stock Market? – “The speed and magnitude of the bond market correction is something investors simply haven’t had to deal especially at the same time stocks are in correction territory.”
  10. Back to the Future of Twitter – “First, Twitter’s current fully integrated model is a financial failure.”

Note: This is based on when I read the article, not necessarily when it was first published.  Unfortunately, my backlog of things I would like to read always seems to dwarf the amount of time I can devote to reading.

Top clicks across the site last month:

  1. Financial Model vs. Operating Model
  2. Email: Don’t Get Fired
  3. EBITDA Is Not A Good Proxy For Cash Flow
  4. Excel Tips: Football Field Chart
  5. Operating Model Tips

Updated stats:

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January891
February1100
March1023
April1032
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Total4046

Email: Don’t Get Fired!

Reading Time: < 1 minute

Have you ever received an email that was sent to you unintentionally?  Or seen one where you know someone was copied, but most definitely should have been.  Or better yet, received an email followed quickly by a recall notice?  I am most definitely not letting you recall the first message.  I will be reading every word of it.

So, here’s another quick email tip.

You can read about the last one here: Don’t Fire & Forget.

I refer to this as my “Don’t Get Fired Rule.”  I’ve only met one other person who does something like this, but everyone should.

I put a two minute delay on all outbound emails.

That’s it. Super simple.

It gives you an extra two minutes to think about what you wrote.

It gives you a chance to correct that recipient you fat fingered. (I purposely don’t autofill addresses – maybe another post).

It slows you down just enough, to slow you down just enough.

For bonus points, you can set the rule so emails sent with “high importance” bypass the delay.  So if you are in a meeting and need to send something quickly and folks are waiting on you, just send it high importance. An enhancement idea that I borrowed liberally (i.e., stole) from the other person I referenced above.

Hope that helps.

That’s A Bunch Of…

Reading Time: < 1 minute

Ok, what am I missing?

The seller wants to sell me house that will cost almost $10,000 per month, and wants to rent it back for $5,000 per month.

I presume that if I do enough of these, I will make it up in volume?

Influential Reads – March 2022

Reading Time: 2 minutes

“Investing a little time where others don’t doubles your impact..” – Farnam Street

I am still working my way through Titan, the John D. Rockefeller, Sr. biography.  But I did tick through a couple works of fiction, Dog Stars and The Guide, both by Peter Heller as well as Into the Wild by Jon Krakauer.  They were interesting enough, but not anything I would highly recommend.  However, it did put some books on the board and helped with some consistency in my daily reading.

Here are my most influential reads – in no particular order:

  1. Russia in Ukraine: Let Loose the Dogs of War! – “Put simply, assuming that crises will always end well, and that markets will inevitably bounce back, just because that is what you have observed in your lifetime, can be dangerous.”
  2. What Bond Investors Should Do as Interest Rates March Higher – “So, he argues, the yield curve’s recession signal is distorted.”
  3. Has The Demise Of The Growthsters Been Greatly Exaggerated? – “Anyone who thinks that either 18% or 25% per year returns in a 2% inflation environment (ahhh, those were the days!) is normal or sustainable, simply hasn’t studied market history.”
  4. Spam as a Service – “As for the valuations being assigned to all these companies, and the expectations of their investors – I would be terrified.”
  5. Signs of stress deepen in the office real estate market – “hose numbers likely overstate how much of that office space is actually being used. Recent data from Kastle Systems, which measure occupancy by looking at foot traffic into offices, showed vacancies of about 60% in major markets.”
  6. Inside the bubble – “And people outside the bubble are supposed to feel left behind, because that’s part of the fuel of life inside the bubble.”
  7. 5 Ways to Simplify Your Life – “My favorite way of going through my day is to do every activity in fullscreen mode.”
  8. Dr. Andrew Huberman: The Science of Small Changes – “Forget trying to get people to change, it does not work. It works with children, it does not work with adults unless it’s self-directed plasticity.”
  9. Is Renting Better Than Buying? We Think So. – “You’re actually better off renting and investing the savings. It’s just too expensive to buy a house.”
  10. Tough Guys – “Play stupid games, win stupid prizes.”

Note: This is based on when I read the article, not necessarily when it was first published.  Unfortunately, my backlog of things I would like to read always seems to dwarf the amount of time I can devote to reading.

Top clicks across the site last month:

  1. Financial Model vs. Operating Model
  2. Influential Reads – February 2022
  3. EBITDA Is Not A Good Proxy For Cash Flow
  4. Ski Gear Thought Experiment
  5. Operating Model Tips

Updated stats:

Read ArticlesBooks
January891
February1100
March1023
April
May
June
July
August
September
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Total3014

Email: Don’t Fire & Forget

Reading Time: < 1 minute

I don’t like to be heavily managed.  And therefore, I try not to heavily manage others.

However, I realized that I had a bit of blind spot in trusting folks to follow through on their commitments.  I would send an email requesting an update or a response to a question.  But never receive a response.  And, I wouldn’t realize that for some time.  And, I didn’t have a good process to track these.

So, here’s what I found works for me.

  1. Create a folder called Follow-up.
  1. Create an Outlook rule that moves any message from me to the Follow-up folder.
  1. BCC myself on emails that I want to make sure I get a response on.
  2. Check the Follow-up folder as part of my weekly planning routine.

Three Take-Aways: Range: Why Generalists Triumph in a Specialized World

Reading Time: 2 minutes

“Compare yourself to yourself yesterday, not to younger people who aren’t you.  Everyone progresses at a different rate, so don’t let anyone else make you feel behind.”  – Range (pp. 290)

This book was talking my book, and since I agreed with most of what was being said, I liked it. There were some interesting sections on teaching and learning, sports and athletics, and career trajectory.  

The sports one hits pretty close to home right now since our daughter is nine.  It seems like kids are being required to pick a sport very early these days.  I was glad to see some research suggesting that’s really not a good idea to specialize early.  By the way, I sat next to a three time Olympian on the chairlift the other day, and she told me the same thing.

The book also had a lot of overlap with a couple of my other recent reads – Superforecasting and Principles.  It even referenced Young Men and Fire (pp. 245) – a book by Norman Maclean (of A River Runs Through It fame) which has stuck with me since I read it a few years ago.

Three take-aways from the book:

  1. Learning Should Be Hard

“Desirable difficulties like making connections and interleaving make knowledge flexible, useful for problems that never appeared in training.” (pp. 96)

“All forces align to incentivize a head start and early, narrow specialization, even if that is a poor long-term strategy.” (pp. 119)

If learning is easy, then you are probably doing it wrong.  Or learning in a way that will help you utilize that knowledge in the future.  Learning should be somewhat difficult.  Early wins might be a bad sign.  

  1. It’s Not People vs. Computers, It is People + Computers

“But the centaur lesson remains:  the more a task shifts to an open world of big picture strategy, the more humans have to add.” (pp. 29)

“Our greatest strength is the exact opposite of narrow specialization.  It is the ability to integrate broadly.”

As the world becomes more digital, you should think about where people spend their time and where computers spend their time.  Each is a tool.  And like every tool, it has its strengths and weaknesses.  This felt extremely applicable to both individual careers choices as well as managing people, processes, and companies.

  1.  Identify & Solve Problems

“Like Kranz, Von Braun went looking for problems, hunches, and bad news.  He even rewarded those who exposed problems.” (pp. 259)

“…successful problem solvers are more able to determine the deep structure of a problem before they proceed to match a strategy to it.” (pp. 115)

This one had a lot of overlap to Principles.  Solving problems is one of my best strengths or at least that is what I tell people in interviews.  And it seems like a good area to focus on going forward, as it is a place where people add a lot of value vs. automation.  In order to creatively solve problems, you need broad perspective.  

A few other recent book reviews:

  1. Principles
  2. That Wild Country
  3. Superforecasting: The Art and Science of Prediction
  4. Essentialism: The Disciplined Pursuit of Less
  5. Fortune’s Formula