Category Archives: Entrepreneurship

New addition to The Library in St. Pete

The latest addition to The Library in St. Pete is Unlocking Creativity – How to Solve Any Problem and Make the Best Decisions by Shifting Creative Mindsets, authored by Michael Roberto. As his interview in Forbes magazine explains, creativity doesn’t typically come from the lack of ideas, but from barriers in organizations that stifle creative thinking.

This is the 3rd of Professor Roberto’s books to join our library, and the first one for which you can find both a brief introduction and a trailer for the book at Youtube.

From among the many terrific insights in the book, we’d like to highlight two:

1 – Shaping team climate is more important than an “obsession” with reorganizations (p. 94-98).  

(H)e presumed that organizational structure drives performance, as many business leaders do. Unfortunately, that causal link is much more complex than many executives realize, as the studies of mountain climbers and sports teams illustrate. Leaders can adopt a variety of organizational structures, and each comes with its own costs and benefits. We cannot simply crank up an algorithm and select an optimal structure that promotes creativity, innovation, and growth. No such perfect structure exists, no matter the strategy, industry, or circumstances…

Leaders need to think about how teams perform their work, and how they can create the conditions that will enable those groups to flourish. The best leaders pay close attention to team climate, behavioral norms and ground rules, and the design of the work itself…

Julia Rozovsky’s People Analytics team collected data on 180 teams throughout Google.  She explains what they discovered:

“We thought that building a perfect team would be pretty algorithmic in nature, because at Google, we love our algorithms.  [However] What our research showed us was that it’s less about who is on the team and more about how people interact that really makes the difference.”

Google identified five attributes of their highest-performing teams, and “a climate of psychological safety proves to be the most important by far.”

We could not agree more. As we ourselves have written, systems and processes are important but what makes a team great are the ‘robust social systems’ in which the members’ informal modus operandi ensure that all those well-designed systems function properly.

2 – It can take time for creativity to pay dividends (p. 172).

Remember, though, that many creative breakthroughs occur when individuals make connections between seemingly disparate concepts. Those links and relationship s may not become apparent overnight. Sometimes, it seems as though these breakthroughs are simply the product of luck. On the contrary, Harvard scholar Ethan Zuckerman argues that, “Engineering serendipity is this idea that we can help people come across unexpected but helpful connections at a better than random rate.”

Here too, we are in agreement, having echoed this line of thought many times. The difference between luck and serendipity is that the latter involves seeing meaningful combinations where others do not and is a skill one can develop. 

Some organizations are “luckier” than others because they tolerate an optimal degree of wastefulness based on the assumption that serendipity relies on loafing and savoring the moment, of wandering and loitering and directionless activity of all sorts. Serendipity is a close relative of creativity and can be encouraged by a few organizational factors.

Lest anyone think we’ve given too much aid and comfort to sloth, inefficiency, and other bad habits, we’ll close with Gary Player’s thoughts on the subject:  “The harder I work, the luckier I get.”

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NB:  We’d like to thank the good professor for comparing venture capitalists to Soviet planners (p.80). We’ve actually known and admired Professor Roberto for a long time, and in fairness to him, he is merely quoting an entrepreneur.  (Ahem, while not objecting…)

Here are a few other instances where we’ve cited the professor’s thinking here at Navigating Venture:

• It’s unwise to rely on one’s instincts to decide when to rely on one’s instincts
• British Petroleum and Epic Failure
• Empirical evidence: power corrupts?
• Conquered but not tamed – team effectiveness at Mt. Everest

Startups Discover the Allure of the C Corporation

The individual income tax-rate cuts of the 1980s helped make LLCs the default business structure for startups – but the 2017 reduction in corporate tax rates, coupled with the capital gains tax rate increases in the 2010s, have changed the dynamic.  

As last week’s Wall Street Journal explains in “Startups Discover the Allure of the C Corporation,” in some circumstances the ‘C’ structure creates potential tax benefits for entrepreneurs and their investors:  

For years, Mr. Bisges started ventures using limited-liability companies, known for their flexibility and tax advantages. But when Mr. Bisges and his nephew, Aaron, started planning StillFire Brewing, their accountant suggested the C corporation.

Mr. Bisges is pinning this part of his business plan on Section 1202 of the Internal Revenue Code, an underused provision expanded under Mr. Obama, and one that is gaining new attention after the 2017 Tax Cuts and Jobs Act made it more attractive.

The strategy is particularly advantageous for business founders who expect to start small, keep earnings inside the company, make annual profits and then cash out. If a taxpayer holds C corporation stock for five years and follows the technical rules, capital-gains taxes on a subsequent sale get erased—on gains up to $10 million or 10 times the original investment, whichever is greater.

In a nutshell, the article argues that it may now be tax advantageous for entrepreneurs to realize their profits in the form of long-term capital gains instead of ordinary income because they can exclude from federal income tax 100% of the gain from the sale of qualified small business stock.

LLCs, S-Corps, and C-Corps each offer different advantages and restrictions, and choosing poorly can lead to expensive and difficult changes down the road. There are many complexities and issues to consider and no one right answer. Just as people shouldn’t decide to have children for the tax benefits, we advise founders to not view tax considerations in a vacuum when choosing the legal structure for their businesses.  They need to think hard about the long term goals for the business and seek expert advice on the optimal legal structure.

You can, however, reduce the number of future headaches (and possibly legal bills) if you choose the structure that is most appropriate for both your current situation and your long-term objectives.  Aside from avoiding personal exposure to business liabilities, the main considerations when choosing from among the three structures are tax consequences and corporate governance issues. 

We ourselves have invested in both C’s and LLC’s, and have found the defined governance structure of a C-corp is almost always preferable.  For a more expansive view of our thinking on the subject, we recommend you check out our 2010 white paper, To LLC or Not to LLC.

New addition to The Library in St. Pete

The latest addition to The Library in St. Pete is Thinking in Bets – Making Smarter Decisions When You Don’t Have All the Facts,  authored by Annie Duke, the professional poker player who began her career when, at age 26, she quit the cognitive-psychology doctoral program at the University of Pennsylvania.  The Wall Street Journal review of her book calls it “the dissertation she never got around to finishing.”

Ms. Duke writes that “our brains weren’t built for rationality” and “they aren’t changing anytime soon” so decision-makers have to “figure out how to work within the limitations of the brains we already have.”

As with many of our irrationalities, how we form beliefs was shaped by the evolutionary push toward efficiency rather than accuracy.  Abstract belief formation (that is, beliefs outside our direct experience, conveyed through language) is likely among the few things that are uniquely human, making it relatively new in the scope of evolutionary time. (p.51)

Duke maintains that the highest-level performers in any field have developed habits to compensate for cognitive biases and unconscious habits.

Among her recommendations are organized skepticism and truth-seeking accountability groups, as well as assorted forms of “mental time travel”:  backcasting, premortems, Ulysses contracts, and moving regret in front of a decision.

The WSJ review nicely summarizes Ms. Duke’s thesis:

Ms. Duke suggests recasting our judgment calls as bets. “We don’t win bets by being in love with our own ideas,” she writes. “We win bets by relentlessly striving to calibrate our beliefs and predictions about the future to more accurately represent the world.” Thinking about choices this way brings with it a profound attitudinal shift, from binary right-wrong thinking to a “probabilistic” approach, in which we choose “among all the shades of grey.” This reframing has a clarifying effect. “The more we recognize that we are betting on our beliefs (with our happiness, attention, health, money, time, or some other limited resource),” Ms. Duke writes, “the more we are likely to temper our statements, getting closer to the truth as we acknowledge the risk inherent in what we believe.”

Moreover, when we state our judgments circumspectly in the form of a bet, we are more inclined to revise them with the arrival of new information. “When confronted with new evidence, it is a very different narrative to say, ‘I was 58% [certain] but now I’m 46%,’ ” writes Ms. Duke. “That doesn’t feel nearly as bad as ‘I thought I was right but now I’m wrong.’ . . . This shifts us away from treating information that disagrees with us as a threat.”

She also argues that the role of skill and luck in sports and business makes it difficult to just “work backward” from outcomes to the decisions we made.

Think about this like we are an outfielder catching a fly ball with runners on base.  Fielders have to make in-the-moment game decisions about where to throw the ball:  hit the cutoff man, throw behind a base runner, throw out an advancing base runner.  Where the outfielder throws after fielding the ball is a bet.

We make similar bets about where to “throw” an outcome:  into the “skill bucket” (in our control) or the “luck bucket” (outside our control).  This initial fielding of outcomes, if done well, allows us to focus on experiences that have something to teach us (skill) and ignore those that don’t (luck).  Get this right and, with experience, we get closer to whatever “-ER” we are striving for:  better, smarter, healthier, happier, wealthier, etc.

It is hard to get this right.  Absent omniscience, it is difficult to tell why anything happened the way it did.  The bet on whether to field outcomes in the luck or skill bucket is difficult to execute because of ambiguity.  …

Outcomes don’t tell us what’s our fault and what isn’t, what we should take credit for and what we shouldn’t.  Unlike in chess, we can’t simply work backward from the quality of the outcome to determine the quality of our beliefs or decisions.  This makes learning from outcomes a pretty haphazard process. (p.86)

Interested, dedicated, fascinated by the job

Today marks the 48th anniversary of the Apollo 11 landing and the first steps by humanity on another world.  In honor of the man who took those first steps, we’d like to reprint the 8/28/12 piece we wrote on the occasion of his passing. 

~~~

Astronaut Neil Armstrong passed away Saturday, and The Wall Street Journal reported something the pioneer once said about the success of the 1969 Apollo 11 mission – the odds of which he had placed at 50/50.

Mr. Armstrong described the required reliability of each component used in an Apollo mission – statistically speaking 0.99996, a mere 4 failures per 100,000 operations – and pointed out that such reliability would still yield roughly 1000 separate identifiable failures per flight.   In reality, though, they experienced only 150 per flight.  What explained the dramatic difference?

I can only attribute that to the fact that every guy in the project, every guy at the bench building something, every assembler, every inspector, every guy that’s setting up the tests, cranking the torque wrench, and so on, is saying, man or woman, “If anything goes wrong here, it’s not going to be my fault, because my part is going to be better than I have to make it.” And when you have hundreds of thousands of people all doing their job a little better than they have to, you get an improvement in performance. And that’s the only reason we could have pulled this whole thing off. . . .

When I was working here at the Johnson Space Center, then the Manned Spacecraft Center, you could stand across the street and you could not tell when quitting time was, because people didn’t leave at quitting time in those days. People just worked, and they worked until whatever their job was done, and if they had to be there until five o’clock or seven o’clock or nine-thirty or whatever it was, they were just there. They did it, and then they went home. So four o’clock or four-thirty, whenever the bell rings, you didn’t see anybody leaving. Everybody was still working.

The way that happens and the way that made it different from other sectors of the government to which some people are sometimes properly critical is that this was a project in which everybody involved was, one, interested, two, dedicated, and, three, fascinated by the job they were doing. And whenever you have those ingredients, whether it be government or private industry or a retail store, you’re going to win.

Exhausted unshaven and lovin’ it

Interested, dedicated, fascinated by the job – Armstrong’s explanation could serve as an excellent description of the esprit de corps we find in good private growth companies.  Not too long ago we quoted Ben Dyer, president of Techdrawl, about how entrepreneurs need to inspire all the members of their team to share the founder’s drive in the early stages of a company:

All those textbook methods of performance reviews, pay incentives, etc. will come in handy when you get to the 50th or 100th employee, but right now you’ve got to be the one out front – with inexhaustible energy, enthusiasm, creativity, and a clearly articulated vision.

In a bit of serendipity we stumbled on this related post, from Richard Martin, which makes an interesting distinction between esprit de corps and teamwork:

Cohesion and esprit de corps are even more intangible. Where teamwork is built on the willingness of individual team members to subsume their own interests in favor of group interests, esprit de corps is built upon the willingness to sacrifice oneself, if needed, for the interests of the group. This is a level of commitment that few organizations in business achieve.

Mr. Armstrong described himself (with characteristic humility) as:  “I am, and ever will be, a white-socks, pocket-protector, nerdy engineer.”  Perhaps that, and a bit more, Sir.  Godspeed.

89 years worth of “the greatest thing since sliced bread”

On this day in 1928, the Chillicothe Baking Company of Chillicothe, MO, sold mechanically sliced bread for the first time in the history of the universe.  This gives us a great opportunity, on a Friday, to re-post a Greatest Hit from our Vintage Future Series – originally published on November 13, 2014:

Our Vintage Future series takes a tongue-in-cheek look back at the failed predictions of past generations of investors and futurists, and the sometimes tortuous routes to success of unlikely ideas.

In our line of work it’s good to guard against the hubris inherent in projecting conventional wisdom too far out into the future, and to remind ourselves that today’s trend can be tomorrow’s punchline – and vice versa.

Our VIIth installment takes a look at “the greatest thing” ever invented and a simple innovation that dramatically altered how we see the world.

Grok this:  Betty White is older than sliced bread!

Even sliced bread took 18 years to succeed.  Otto Frederick Rohwedder, a jeweler from Missouri, built his prototype “Machine for slicing an entire loaf of bread at a single location” in 1912 but saw it destroyed in a fire.  15 years later he filed his patent, but the end product languished due to its untidy appearance and concerns about freshness.  One year later a St. Louis baker named Gustav Papendick put it in cardboard trays and wrapped it in wax paper, yet even then it didn’t take off until it helped a little company called Wonder Bread go national in 1930.

Except for a brief ban during WWII (the steel used to build the slicers had more pressing uses), sliced bread grew quickly and became a platform on which others could dream and build – in this case new types of spreads and jams.

Sometimes a simple idea – like digging ditches – can change the world.  Before most cables ran underground, all electrical, telephone and telegraph wires were suspended from high poles, creating strange and crowded streetscapes.

A tower with 5000 phone lines in Stockholm, cused 1887-1913

The only thing he ever made fly was government money

On this day in 1906, the Wright Brothers were granted a patent for their “flying machine.” In honor of the anniversary, we reprint this – one of our most popular, most-read pieces.  

(Original publish date: April 17, 2013)

The process of productive capital allocation is a critical ingredient of innovation and job growth.   Entrepreneurs spending their own (and their partners’) money will create more jobs, more innovation, and a more vibrant economy than politicians picking winners and losers based on cronyism, campaign contributions, and constituent pork.

When government strays out from funding basic research into either applied research or the means of production, the results range from poor to scandalous.  Ideas are infinite, and in the absence of competent execution, they are worth nothing.  Even if the idea has merit, the true expertise is crowded out.  There are better ways policymakers can help encourage innovation.

The invention of the airplane provides an excellent example.  While we’re all aware it was the Wright Brothers, many interesting details about funding the innovation don’t make it into school textbooks.  In A Tale of ‘Government Investment’  Lee Habeeb & Mike Leven recount the race between the bicycle shop owner/operators and the government-backed head of the Smithsonian.

Who better to win the race [to powered flight] for us, thought our leaders, than the best and brightest minds the government could buy? They chose Samuel Langley. [The War Department gave Langley $50,000, an enormous sum at the time, which The Smithsonian augmented with taxpayer funds of its own.]  You don’t know him, but in his day, Langley was a big deal. He had a big brain and lots of credentials. A renowned scientist and a professor of astronomy, he wrote books about aviation and was the head of the Smithsonian.  It was the kind of decision that well-intentioned bureaucrats would make throughout the century — and still make today. Give taxpayer money to the smartest guys in the room, the ones with lots of degrees. They’ll innovate and do good for us.

For that Solyndra-type investment the country got the “Great Aerodrome,” which “fell like a ton of mortar’ into the Potomac River – twice.  Representative Gilbert Hitchcock of Nebraska remarked, “You tell Langley for me that the only thing he ever made fly was government money.”

Samuel Pierpont Langley’s Aerodrome  and launching apparatus.

Nine days after that second failed test flight, a “sturdy, well-designed craft, costing about $1000, struggled into the air in Kitty Hawk.”

How did two Ohio brothers accomplish what the combined efforts of the War Department, The Smithsonian, and other people’s money could not?  The authors cite James Tobin’s To Conquer the Air: The Wright Brothers and The Great Race for Flight (2004) to provide a few answers:

• Langley saw the problem as one of power:  how to go from zero to 60 in 70 feet, the stress of which was too great for the materials used.  The Wright Brothers, inspired by the practical skills and insights gained from tinkering in their bike shop, understood the problem was one of balance (on a bike, balance+practice = control).  They invented the three-axis control (pitch, yaw, roll) still standard on fixed-wing aircraft today.  Their entrepreneurial technical expertise was an advantage neither the government nor other private competitors (Alexander Graham Bell) could match.

• Since they couldn’t afford repeated test flights the Wright Brothers were forced to develop a wind tunnel to test their aerodynamics.  This saved money and time, since they weren’t bogged down repairing the wrecks of a flawed design.

• No government money also meant no government strings.  They were freer to experiment and innovate without worrying about non-essential requests and hidden agendas.  They also managed to do more with less since they couldn’t afford subsidy-induced waste.

Habeeb & Levin also offer this fascinating, if not unexpected, coda:

Though the Wrights beat Langley and the Smithsonian, the race didn’t end there. Powerful interests vied for the patent to this revolutionary invention and, more important, for the credit for it. With Smithsonian approval, a well-known aviation expert modified Langley’s Aerodrome and in 1914 made some short flights designed to bypass the Wright brothers’ patent application and to vindicate the Smithsonian and its fearless leader, Samuel Langley.

That’s right. The Smithsonian’s brain trust couldn’t beat the bicycle-shop owners fair and square, so they used their power to steal the credit. And then they used their bully pulpit to rewrite history. In 1914, America’s most esteemed historical museum cooked the books and displayed the Smithsonian-funded Langley Aerodrome in its museum as the first manned aircraft heavier than air and capable of flight.

Orville Wright, who outlived his brother Wilbur, accused the Smithsonian of falsifying the historical record. So upset was he that he sent the 1903 Kitty Hawk Flyer, the plane that made aviation history, to a science museum in . . . London.

But truth is a stubborn thing. And in 1942, after much embarrassment, the Smithsonian recanted its false claims about the Aerodrome. The British museum returned the Wright brothers’ historic Flyer to America, and the Smithsonian put it on display in their Arts and Industries Building on December 17, 1948, 45 years to the day after the aircraft’s only flights. A grand government deception was at last foiled by facts and fate.

As for Samuel Langley, he died in obscurity a broken and disappointed man. Friends often noted that he could have beaten the Wright brothers if only he’d had more time — and more government funding.

Some things never change.

The Wright brothers’ airplane business never took off (groan) due to a combination of poor business decisions and sloppy patent work.  Wilbur sadly died young (in 1912 at age 45, of illness that some suspect was contracted due to exhaustion from the patent battles) and Orville sold the company in 1915.  So the industry grew under the leadership of other companies and other men.  (Although the Curtiss-Wright Corporation remains in business today producing high-tech components for the aerospace industry.)   One can’t help but wonder what the original inventors might have done had they been the beneficiary of a strong partnership with a VC fund…

Successful people invest in relationships

Good article in Entrepreneur about how true success is not possible unless you build great relationships.  The piece hits several themes that we believe are critical to a successful vc-entrepreneur marriage: maintaining long term relationships, communicating good news and bad, promoting honesty in business, how useful failures can prevent epic ones, and maximizing board effectiveness.

The chemistry between entrepreneur and venture partner in private companies is more cooperative, longer-term, and (mercifully) not subject to the quarterly reporting pressures of public companies.  Both will have real “skin in the game” and the same incentive to understand the nuances of the business and focus on long term value creation.

You will spend a great deal of time, effort, and money together with a new partner, so the chemistry ought to be productive and enjoyable. It should add conviviality in the good times and take the edge off the bad times.

Here are a few highlights from the article “How Successful People Build Exceptional Professional Relationships.”

They help without having to be asked.

People who build great relationships pay close attention so they can tell when others are struggling. Then they offer to help… but not in a general, “Is there something I can do to help you?” way. Instead they come up with specific ways they can help.

That way they can push past the reflexive, “No, I’m okay…” objections and then roll up their sleeves to make a difference in another person’s life.

And they do it not because they want to build a better relationship — although that is certainly the result — but simply because they care.

They take the undeserved hit.

She’s willing to accept the criticism or abuse because she knows she can handle it — and she knows that maybe, just maybe, the person who is really responsible cannot.

Few acts are more selfless than taking the undeserved hit. And few acts better cement a relationship.

They answer the question that was not asked.

Where relationships are concerned, face value is usually without value. Often people will ask a different question than the one they really want answered… Behind many simple questions is often a larger question that goes unasked. People who build great relationships listen carefully to discover what lies underneath so they can answer that question, too.

They step up when they have acted poorly.

Responsibility is a key building block of a great relationship. People who take the blame, who say they are sorry and explain why they are sorry, who don’t try to push any of the blame back on the other person… those are people everyone wants in their lives, because they instantly turn a mistake into a bump in the road rather than a permanent roadblock.

They know when to dial it back.

People who build great relationships know when to have fun and when to be serious, when to be over the top and when to be invisible, and when to take charge and when to follow.

Great relationships are multifaceted and therefore require multifaceted people willing to adapt to the situation — and to the people in that situation.

They value the message by always valuing the messenger.

Smart people strip away the framing that comes with the source — whether positive or negative — and consider the information, advice, or idea based solely on its merits.

People who build great relationships never automatically discount the message simply because they discount the messenger. They know good advice is good advice, regardless of where it comes from.

And they know good people are good people, regardless of their perceived “status.”

The migration of talent and capital to the high-tech corridors of the Southeast

Good article from Technet about how the startup economy has spread across the country:

This is the most recent item in a long run of stories describing a geographic analog to the process of creative destruction.  Those states who spray “startupicide” on the economy –  suffocating regulations, inflated business taxes and fees, lawsuit-friendly legal environments, and political classes uninterested in business concerns, if not downright hostile to them – lose economic clout as people and capital migrate to other states with more favorable environments in which to work and live.

Local evidence of this trend can be found in this story, in which the U.S. Census Bureau reports

Three metro areas in Florida were among the nation’s 10 biggest gainers in the number of people moving there last year, and another three Florida metro areas were in the top 10 for overall growth rates.

Our hometown Tampa was #5 in the nation in 2016 population growth.

This migration of economic clout within the US has been more subtle than the California Gold Rush or Irish Potato Famine but is just as significant.  Some states are chasing away their earners, workers, and entrepreneurs; this is their tax base.

The growth corridors of the high-tech South would have a mercantile-like advantage but for the fact that employers can (and do!) simply move in order to thrive under our growth-oriented tax policies, lower public sector debt burdens, stronger job creation, excellent climate for entrepreneurs, and a superior overall business climate.  (The actual climate happens to be conducive to a great quality of life as well.)

Which is better for an entrepreneur: an LLC or a C corp?

We have written from time to time on the question of which legal structure is best suited to private growth companies looking to raise outside growth capital.  Not surprisingly, there is no one right answer to the question, but recent tax legislation should compel entrepreneurs to give serious consideration to the C-corporation structure.

This article in last week’s Business Observer contains important news about the potential tax benefits of a C-corporation for entrepreneurs and their investors.

However… just as people shouldn’t decide to have children for the tax benefits, we advise founders to not view tax considerations in a vacuum when choosing the legal structure for their businesses.  They need to think hard about the long term goals for the business and seek expert advice on the optimal legal structure.

The author of the article (Pamela Schuneman,  C.P.A.) first argues that the prospects of federal tax reform may tip the scales towards choosing a C-corp:

Now, with tax reform on the horizon and a push to lower the corporate tax rate, current tax savings on C Corporation earnings could be substantial if the corporate rate drops to 15% and the top individual rate only drops to 33%. That’s an 18% difference — $18,000 more on $100,000 of income.

It’s a little more accurate to say the corporate rate drops “closer” to 15%, which compares favorably to an LLC structure where investors are taxed at their individual income tax rates on income that is “passed through” to investors.

Next she explains that a 1993-era tax provision governing a type of capital gains, originally scheduled to expire at the end of 2010, has been made permanent.  And this change, in our view, is a potential game changer.

The gain exclusion for Sec. 1202 was originally set [now made permanent – ed] at 50% for stock acquired [in private C corps – ed] on or after Aug. 11, 1993, increased to 75% for acquisitions after Feb. 17, 2009, and expanded to a full 100% exclusion for acquisitions after Sept. 27, 2010.

The 2010 law also removed of one of the main drawbacks of this tax provision – the alternative minimum tax preference.

In a nutshell, Sec. 1202 allows taxpayers (other than corporations) to exclude from federal income tax 100% of the gain from the sale of qualified small business stock (“QSBS”). The amount of gain excluded is limited to the greater of $10 million or 10 times the adjusted basis of the investment.

There are requirements to qualify for the tax break, which we outline below.  But first we’d like to share one more excerpt from the article to emphasize the importance of this legislation to founders and their investors:

For example, Tom and Jane decide to start a software development business. They purchase stock for $10,000 each and have a 50-50 ownership interest in the C Corporation. The stock is eligible for Sec. 1202 treatment if held for five years. In six years, they sell the stock of the company to Google for $10 million. They each have a $4,990,000 gain on the sale of the stock and their tax on the transaction is zero.

Of course we see this as a positive development for the high-growth companies responsible for all net job growth in our economy.  Reasonable people will disagree on what tax rates should be.  But can we at least agree that there are some forms of investment activity which promote economic growth, and that those forms ought to be encouraged, perhaps with favorable tax treatment?

RELATED STORY:  Warren Buffett and after tax returns

If a company’s stock is qualified small business stock (QSBS) then the Internal Revenue Code (§1202) provides a tax break on the equity investments.  To qualify as QSBS and for the 0%  federal tax rate on gains from the sale of QSBS, the following requirements must be met:

1.)  Original issue.  The taxpayer recognizing the gain must be an individual, partnership, S corporation or estate and must have acquired the stock at original issue from a US domestic C corporation.

2.)  Five-year holding period.  The taxpayer must have held the stock for more than five years prior to selling the stock.

3.)  After September 27, 2010. The taxpayer must have acquired the stock at original issue after September 27, 2010, in exchange for cash, property other than cash or stock, or services.

4.)  $50 million Gross Assets Test.  The aggregate gross assets of the corporation that issued the stock cannot have exceeded $50 million at the time of (including immediately before and after) the issuance of the stock to the investor.

5.)  Active Business Test.  During substantially all of the taxpayer’s holding period of the stock, at least 80% of the issuing corporation’s assets must be used by the corporation in the active conduct of one or more qualified trades or businesses.  (Certain types of businesses, including some pure service businesses like consulting firms or doctor practices, don’t qualify, but many businesses do.)

6.)  No significant redemptions.  The issuer of the stock must not have engaged in specific levels of buybacks (redemptions) of its own stock during specified periods (typically one year) before or after the date of issuance of the stock to the taxpayer.

The amount of gain eligible for this 0% rate is subject to a cap, however. Section 1202(b)(1) states that the aggregate amount of gain for any taxpayer regarding an investment in any single issuer that may qualify for these benefits is generally limited to the greater of  (a) $10 million, or (b) 10 times the taxpayer’s adjusted tax basis in the stock. For a taxpayer who invests cash in the QSBS, basis would generally be equal to the cash purchase price.

Like all issues tax-related, entrepreneurs need to consult with their tax counsel and accounting firm to determine if their businesses qualify for QSBS status.  If a business does qualify, an entrepreneur must decide whether these potentially significant tax savings outweigh other considerations.  In our view, Congress has now put its thumb on the scale firmly on the side of choosing the C-corporation structure.

Risk-taking in the NFL

The WSJ recently analyzed NFL play calling this season and concluded that the coaching profession could use more risk-takers.  Despite “a legion of mathematicians, economists and win probability models urging them to take more chances“ most NFL coaches “reach for the conventional choice by habit.”

From Why NFL Coaches Take No Chances:

The Journal analysis examines how coaches played their hand this season across three broad categories of game management: fourth downs; play calling (blitzing on defense; passing on early downs or with the lead on offense) and special teams (going for a 2-point conversion and onside kicks when ahead)…

University of Pennsylvania professor Cade Massey, who researches behavior and judgment, said many NFL coaches habitually choose to postpone the certainty of losing in football for as long as possible—even if doing so actually lowers the likelihood of winning in the end, such as opting to punt on fourth-and-short in overtime…

There is some evidence that coaches are seeing the benefits of riskier decisions. They are just becoming more aggressive at a very conservative pace.

In a 2002 paper, University of California Berkeley economist David Romer expressed hope that coaches would begin acting rationally in maximizing odds of victory when the related data became more widely available. And this year, coaches have gone for it on fourth down needing two yards or less 29.7% of the time—converting nearly two-thirds of attempt).

That’s up from 23% just before Romer published a paper entitled, “It’s Fourth Down and What Does the Bellman Equation Say?” Alas, at the present rate, going for it nearly all the time as the models advise would take over 100 years.

We think this is an excellent illustration of two ideas relevant to starting and running a high-growth company, over and above the obvious exhortation to take intelligent risks:  (1) the opportunity for a contrarian advantage and (2) the combination of data and gut instincts required to make the right call.

First, an excerpt from our  12/8/14 post, We challenged the dogma, and it was incorrect:

[The story about EOG Resources, a discarded division of Enron ] is an absorbing look at the “shale revolution” and touches on several of our favorite themes:  iterative collaboration, how to fail the right way, the incremental, adaptive ways by which success is achieved, and even the role of luck – although we’d describe it a bit more favorably as “serendipity.”

EOG is a great example of a contrarian definition of entrepreneurship:   see economic value where others see heaps of nothing, combine the self-confidence to defy conventional wisdom with the determination to overcome obstacles, and distinguish yourself more by the ability to achieve the impossible than the originality of your thinking.

Next, an excerpt from our 4/13/16 post, The Hidden Power of Trusting Your Gut Instincts:

(S)tudies show that those who rely on intuition alone tend to overestimate its effectiveness.  They recall the times it served them well and forget the times it didn’t.  Keeping a list of every time intuition is your only guide might be eye-opening.

“Common sense” justifications can be found for almost any conclusion, and as a result it can be shockingly unreliable and something that we over-rely on to the exclusion of other methods of reasoning.  Here’s how we put it in Everything is obvious once you know the answer:

It is “rarely practical to run the perfect experiment” before making a decision but we can be “more deliberative and reflective as we gather and analyze facts to inform our decisions.”  When we over-rely on common sense alone, we risk “rejecting a more thorough effort to solve a problem and settling for an easy one.”

… In our experience the best results often come from a combination of deliberation and intuition.

Finally, in the spirit of the (NFL playoff) season, we’d like to recommend two other pieces about NFL coaches that speak more to leadership challenges than data-driven decision making.

From 1/29/13, The imperfect perfectionist.  On the extent and limits of Bill Walsh’s innovative genius:

Coach Walsh’s West Coast Offense won the 49ers four (or five) Super Bowls, spawned copycats around the league and forced defenses to innovate in response.  Not a bad day’s work.  But obsession with perfection left him badly burnt out and his organization unable to implement his vision without him.

From 2/8/15, The NFL’s Best Coach*.  On the extent and limits of Bill Belichick’s…  innovative genius:

We suspect his efforts to gain those “edges off the field” will also be a permanent part of his legacy.  His team hasn’t been in 6 Super Bowls over 15 years because of deflated balls, or illicitly videotaped signals, or (pre-Belichick) a snowplow driven by a convict on work release.  But you earn the reputation and invite the asterisks when you proudly display that same snowplow in an exhibit at your stadium.

To paraphrase the old adage: reputations are built over the long-term, and can be forfeited in just a moment.  In our business failure can be counted on to make (at least) a cameo, so it’s critical to learn how to fail the right way and make a distinction between business failure and personal failure.  An entrepreneur (or coach?) can try too hard to avoid an enterprise failure and pressure himself into a career-damning ethical lapse.