Musings And Dialogue On Entrepreneurs And Decision Making (Part 6)

The following backdrop and questions apply to this part of the series of musings and open discussion on entrepreneurs and decision-making (See Part 1, Part 2, Part 3, Part 4, Part 5):

Are entrepreneurs more willing to fail than other people? Does this relate to the exploration versus exploitation differences in the sense that entrepreneurs may simply continue exploring new opportunities until they find one that works? How should they trade off a willingness to walk away from a faltering opportunity against the need for persistence, on the chance that the opportunity can still be saved? Do you think this behavior explains serial entrepreneurs?

Here are my off-the-cuff thoughts on these exploratory research questions. Subconsciously and by choice of profession, entrepreneurs are generally more willing to fail than others, particularly when their entire livlihood and financial security are not at stake. This has been one of the most common perspectives that I had been ingrained with, particularly as it relates to debates on founder liquidity (and restricting it). That said, entrepreneurs (and particularly serial entrepreneurs) do not consciously believe that they will fail. They seem to generally have an attitude of "I will win".

To the decision-making question of "walking away" versus "persistence" for a faltering opportunity, I believe that entrepreneurs should consider leveraging mechanisms, such as:

  • having a good principal/partner as a founder that can complement the skillset of the CEO
  • seeking Board of Directors input
  • having an informal "godfather" (established in advance) that the principals or the CEO can turn to for important decision points and/or when disagreements arise in the management ranks.

As to what drives serial entrepreneurs, my thinking is that appetite for creation, personality type, need for independence, promise of financial gain, and ego tend to drive the serial-types more than decision-making tendencies of "walk away" versus "persistence". That said, often serial entrepreneurs have a personal investment philosophy that in the long-run, by starting and running ventures, eventually one of them will pan out very nicely, and they will have learned from their failures and flops. Failing is an important part of the process, and I even remember an executive recruiter for Sequoia Capital commenting to me during an interview for a position in the late 90s that the major downside to my resume at the time for being venture capital associate was that I had not "founded and flopped" a business.

What are your thoughts and experiences?

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Musings And Dialogue On Entrepreneurs And Decision Making (Part 5)

The following backdrop and questions apply to this part of the series of musings and open discussion on entrepreneurs and decision-making (See Part 1, Part 2, Part 3, Part 4. Note that there will likely be a total of six parts for this series with a recap summary of feedback at the end):

One difference between time and money is that money can be stored (inventoried) for future use, but time cannot – it’s use it or lose it. This allows money to be fungible; you can move it around as you need it. For large companies, time can become fungible by hiring or firing workers; entrepreneurs don’t usually have this luxury. How does the inability to store time affect entrepreneurs, especially in comparison to larger companies? What does this imply for time management?

Here are my off-the-cuff thoughts on these exploratory research questions. For permanent changes in capacity (e.g., related to building new capabilities or downsizing), my experience is that hiring and firing of workers is a more painful process in a large company. This has to due with all of the process, legal, HR, budget, management alignment, etc. that cuts across many groups. The larger company, however, has more resources and a greater margin for error. Larger companies may also benefit from having some supply-side agreements in place to readily outsource to consultants or contractors, although the complexity of these contracts sometimes makes it more difficult to source specific, single resources. The upshot, off-the-cuff, is I would hypothesize that larger companies would be somewhat slower in terms of making changes to capacity, that changes can be more efficient in batches, and that margin for error might be a bit larger (on average).

Entrepreneurial firms may be more cash constrained and have less margin for error. That said, they may be quicker in terms of hiring and firing if only because there may be fewer formal processes. What may be working against entrepreneurial firms are that since resources are constrained, they may not always use HR support (e.g., recruiters) in terms of sourcing candidates. To compensate for this fact, I have often found in entrepreneurial situations that one may rely on informal networks more for the hiring process. This may provide an improved screening process for entrepreneurs. The informal networking may also have auxiliary benefits for the entrepreneur (beyond the hiring process itself, such as getting sales leads or industry info) so entrepreneurs may be able to get multiple benefits more easily through the hiring process. All-in-all from a capacity model perspective, my experience is that large capacity changes are harder in entrepreneurial firms, and margins for error are smaller. Yet changes can be quicker, more customized, and dovetail with other efforts.

What are your thoughts and experiences?

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Musings And Dialogue On Entrepreneurs And Decision Making (Part 4)

The following backdrop and questions apply to this part of the series of musings and open discussion on entrepreneurs and decision-making (See Part 1, Part 2, Part 3. Note that there will likely be a total of six parts for this series with a recap summary of feedback at the end):

New research is uncovering differences in types of decisiveness – for example, someone who can’t decide which dessert they want after dinner may not be the same as someone who puts lots of research into buying a car. When does a lack of decisiveness come from the need to get more information, and when is it simply putting off a decision (procrastination)?

It is very hard to generalize. As context, my immediate gut thoughts are that, in general, there are both emotional (e.g., "in the moment") and rational factors (e.g., looking at data) that entrepreneurs need to balance in order to make good decisions. Successful entrepreneurs will tend to be those that either have good business instinct from prior experience in the industry or comparable market and have an ability to look at facts. Alternatively, successful entrepreneurs may be those that have exceptional, innate, outlier-type business instincts and abilities to judge and facilitate people which compensates for weaker abilities to in analyzing factual information systematically (alternatively they may partner with someone who has these skills). I think it would be the rarer exception for a successful entrepreneur to be someone who can only look at rational factors, but this could work in areas like the hard sciences where intellectual property and ability to appropriate profits is high.

With that as my frame, to the question "When does a lack of decisiveness come from the need to get more information, and when is it simply putting off a decision (procrastination)?" my thinking is:

  • If the entrepreneurial team has a balance of experienced emotional- and rational-based decision makers, then putting off a decision is procrastination when the team cannot articulate what additional information or context would be needed to make a decision.
  • Alternatively, if the entrepreneurial team is made up of primarily experienced, emotional-based decision makers, then putting off a decision is procrastination either when they have made similar judgment calls in the past with substantially less information and risk or when they do not identify what complementary resource they need to help with the decision (e.g., legal counsel).
  • Alternatively, if the entrepreneurial team is made up of primarily rational-based decision makers, then putting off a decision is procrastination (presuming context such as market timing is right) either when past experience and knowledge is needed (e.g., prior entrepreneur consultation or complementary resource such as sales VP) and not sought or when excessive analysis is performed.

The basic gist is that I feel that entrepreneurs procrastinate (presuming the market timing is right) to make a decision when neither can they articulate what additional information is needed to make a decision nor are they actively seeking the complementary resource (in terms of balancing functional and emotional/rational decision-making traits) that they need to make an informed decision.

What are your thoughts and experiences?

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Musings And Dialogue On Entrepreneurs And Decision Making (Part 3)

The following backdrop and questions apply to this part of the series of musings and open discussion on entrepreneurs and decision-making (Part 1 here and Part 2 here. Note that there will likely be a total of six parts for this series with a recap summary at the end.):

Some researchers talk about humans trading off exploration (testing the environment) against exploitation (using resources once they’re identified). For example, see link about small children’s learning behavior here. Do you think entrepreneurs are more focused on exploration or on exploitation? How does this compare to other jobs?

My off-the-cuff thinking on these questions are that entrepreneurs tend to be stronger than other workers in terms of exploration mainly because exploratory skills align with the creativity skills that entrepreneurs often have. Whether entrepreneurs focus on exploration versus exploitation, however, has to do more with what type of business is being pursued than something specific to the entrepreneur's disposition or decision-making style relative to non-entrepreneurs. For example, if the entrepreneurial business is something relatively unexplored (e.g., introducing a household device that can interface with your computer for printing paper that can be folded into edible food), then the entrepreneur needs to tap into exploration skills. On the other, an entrepreneurial business that is a copycat business (e.g., introducing a lowest-cost mobile phone provider in a new geography like Canada), well then the entrepreneur needs to focus more on exploitation (with potentially small customizations or market studies in the local market).

What are your thoughts and experiences?

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Dream Interpretation As It Applies To Business

An increased amount of attention has been brought back to
the decision-making field of research with the release of Malcolm Gladwell’s book,
“Blink”
. Gladwell’s book focuses on the power of the subconscious and tacit
knowledge in decision-making processes (while conscious). The book is available here at the bookstore at the business school at INSEAD, and his other book, "The Tipping Point" is part of the reading material for one of the courses on organizations (similar to how positioned at the University of Chicago business school to my understanding).

Completing the "Blink" book made me remember a book I read many
years ago on dream interpretation (note Gladwell’s book did not cover deep sleep dreaming, daydreaming, nor spontaneous thoughts that appear during the day). A key motivator for the book was this … wouldn’t it be powerful if one could gain additional benefits
from the activity that we spend one-third of our lives doing, i.e., sleeping?

The book was not Freud-style dream interpretation, where
Freud advocates (to my understanding) literal
interpretation of dreams. Instead, the book I read offers up the notion to the
effect of that each person has their own
data dictionary
– dreams are a way of the subconscious communicating with
the conscious mind using images. The meaning of images in a dream (which are frequently
severely exaggerated) can best be understood by reflecting upon the dream as a
whole and the feelings the dream imparts and then determining what feels right
and comfortable as an explanation.

As an example, a woman described a dream where she was
murdering her husband by bludgeoning him over the head with a vacuum cleaner.
Also noteworthy was the fact that the husband appeared as an animal in the
dream – specifically a pig.

Freud might argue the dream literally – that the woman was
at risk of murdering her husband. Reminds me of the Tom Cruise movie, “Minority
Report”.

The book I read offered a different explanation. The
exaggerated nature of the dream was simply an artifact of dreams trying to
communicate with us. Here, the woman had some hard feelings toward her husband
because she felt he was restricting her in the home. The vacuum cleaner
represented “domesticity,” and the pig reflected feelings towards the husband
as a “chauvinist pig”. Murdering only meant that there were strong feelings
that the woman and husband should try to resolve (before things got out of hand).

When working with the executive team at my prior employer to
bring in a corporate venture capital round, I recall many tense discussions
surrounding negotiating terms for the new investor class with respect to angel
investors. I would dream about some of the issues during my sleep, and I would
wake up with the tenuous items popping into my head. Sometimes these cues would
trigger me to go back and talk with an angel investor or founder on specific
points. At other times, dreams simply reflected anxiety or feelings of
happiness as to how a client project for me was going. Much like a subconscious
reminder that pops into one’s head during the day that you should call someone
you haven’t talked to in awhile, pursue someone for a job opportunity or
project, etc., I would sometimes find subconscious cues important to
prioritizing personal action items, raising my sensitivity to other parties, and
recognizing my own feelings better.

Managerial Decision Making and Spiderman

I completed Malcolm Gladwell’s books, "Blink" and "The Tipping Point", and I plan to read three of Seth Godin’s marketing-oriented books next in order to keep my MBA fresh. My impression and initial investigations to date have me thinking that these books have not penetrated business schools very heavily yet. Perhaps some of these books should be recommended in business schools or parts included in packets. I gave very high-marks to "The Tipping Point". Malcolm Gladwell indicated to me via email that it’s probably too early yet to know if "The Tipping Point" will penetrate the business schools, but he is hoping so.

Having just finished "Blink", I wanted to share some thoughts related to subconscious decision-making and making decisions based on "gut feeling". This is an interesting topic in the management consulting field, which bases its core on fact-based decision making (as I’ve hinted here). Making decisions based on gut feel is generally frowned upon. I suppose this is also true for managers (non-consultants) within operating companies, but I would venture to say that since management consultants are independent third-parties to solving business problems, there is more polarization and social pressure for consultants to rely on facts (just like patients rely on medical doctors to rely on facts).

I’m not aware of any grand unification theory for balancing fact-based decision making with subconscious decision-making, but I’ll offer my working model for handling the balance (it may be more liberal than traditional consultants). I basically use what I call my "spider sense" to balance fact-based decision making.

Spider-sense is based on Stan Lee’s superhero, Spiderman, who gets a tingling sensation when something bad is about to happen to him.

So my general "algorithm" for decision-making (work in progress) is to:

  1. rely on facts
  2. check your gut feel or "spider-sense"
  3. if #1 and #2 are in alignment, great (i.e., the facts and spider-sense agree)
  4. if #1 and #2 are wildly out of alignment (contradict one another), better re-check the facts or re-factor what is going on around you
  5. on the margin (i.e., if #1 and #2 contradict, but they are not wildly out of alignment), if you have above moderate expertise in the subject matter, then weigh "spider-sense" more than the facts. Otherwise, try to seek out an expert (or godfather or mentor) to fill-out the tacit knowledge gap.

The other caveat to this is that one must constantly try to sharpen one’s spider senses. In business, some of this has to be done by focusing on vertical experiences within an industry sector. However, sharpening managerial decision making in a more general way is also important. In some business schools, this is covered in classes on organizational behavior (OB), and schools may have required OB courses to earn the MBA degree. OB training helps one to become more cognizant of biases that people have when processing information and making decisions. Whether biases are good or bad in a particular situation depends. Nevertheless, there are a ton of biases out there and OB classes help to give people a structure for thinking about these kinds of things.