Tech Strategy (Future): My top 5 ML and AI Predictions

The last few months have been quite a ride. I took off a few months to help my wife take care of our son back in October and what I assumed would be time spent mostly changing diapers turned out to be much more (I may write about this in a later post).

In addition to having lots of family and friends visit and a bit of traveling back to the east coast, I managed to cram in an Intro to Machine Learning class at Udacity. The only way I can describe it is INCREDIBLE! After spending the last few years leading large teams in digital strategy, project management, and consulting, it was refreshing to get back to coding and learning something new.

Spent the last couple of months doing machine learning with sklearn, python, and a bit of TensorFlow 🙂

I can hear someone out there asking: “Why would you spend your free time in python, learning how to analyze data with machine learning algorithms?”
The short answer is that this is where the world is headed and we all should learn at least one new skill every year.

So what exactly did I learn? Here are the top 5 things that stuck with me from the Udacity class and my own self learning:



Machine Learning (ML) and Artificial Intelligence (AI) are here now, so if the machines will be our overlords, why not jump teams and join them…All kidding aside, AI and ML are already in many products that we use each day and will continue to use in greater numbers and frequency (Amazon Alexa / Echo, Google Now, Google Home, Microsoft Cortana, Self-driving Cars, Parking Assistance, etc.). Many of our interactions online are with Chat Bots that learning from human interactions to get increasingly more conversational each day. I wanted to have a deep understanding of the underlying technology to not only have relevant discussions on the topic with clients and business partners, but also look for new opportunities in this space.



Machines will not make (all) humans irrelevant. This was something that I found interesting as I delved into the accuracy rates of the various algorithms and methods that make ML and AI possible. With most generalized ML algorithms, the best we can currently hope for is between 75% — 90% accuracy. Not bad, but not that great either. There aren’t many situations where 75% accuracy is celebrated. This is where a concept of Hybrid Intelligence fills in the missing pieces to help machines with particularly difficult decisions that humans have evolved to answer very effectively.



The next wave of AI will have us texting with our AI companions in much the same way that we text each other now. The first wave of mass-market AI will be products like Alexa and Google Now that require you to voice your commands out loud. This is a great start and novel at first, but eventually speaking out loud at home when you are alone will seem weird and unnatural (I am there already with Alexa and Google Now). I believe Mark Zuckerberg in the right path with potential integration with FB Messenger and his own custom smart home set up. The coming AI interfaces will leverage the gains made in natural language processing to give us the the ability either voice commands such as lights off or text a picture of a friend to our AI assistant to unlock the front door when they arrive (this involves natural language processing, home security, facial recognition, chatbot, etc…fun stuff).

Tech Future: AI Overlords


Many jobs and tasks that are thought to be safe will be disrupted.However, this only means that we need to acquire new skills to move up the ladder into positions or jobs that require human judgment and intuition. Jobs that are repetitive, sequential, etc. are ripe for AI and machine learning right now. However, tasks that require lots of input but have a predictable outcome are being taken on by machines now. Legal documents that are just templates to be filled in by paralegals, legal contracts that don’t/won’t change, technical documentation such as data schemas, network diagrams, devops processes; these are all jobs that machines are doing every day in increasing frequency.



The cost of prediction continues to fall as machine learning algorithms get more accurate and we accumulate more data. Many companies hire consulting firms to analyze multiple scenarios and lots of data to give their best options for a critical decision. These very highly paid consultants are not cheap, but do serve their clients well. However, I believe that AI and machine learning will not necessarily replace the need for consultants, but it will decrease the cost of consulting, data analysis and prediction across every single industry. As we see better use of the data that is accumulated each day and we all get better as asking the right questions of our AI companions, we will see its use in common use from preschool to nursing homes.

Just as millennials were the first generation to grow up with the Internet, we are about to see the first generation (my son included) that will grow up with AI as the norm. The next few years will be really exciting and I look forward to being a part of it.

Daniel is a digital consultant specializing in IT advisory on technology strategy, investment, and implementation. He helps companies solve complex and strategic problems across multiple industries and domains. His drive to find solutions for clients and attain personal growth for himself are what keeps him at the forefront of innovation and helps him guide teams and organizations to cultivate amazing products and services. He can be found on Twitter at @dewilliams.

Life Strategy: Financial Advisor Filter in 25 Questions

Over the last year, I have worked on a side project to straighten out my family’s finances and investments into a more streamlined strategy. A part of this was to determine whether I would take the DIY approach to financial management or hire a professional advisor to help make things a bit easier. After interviewing multiple advisors and wealth managers, and not hearing any compelling reason to give complete stranger access to my finances (not to mention the fees ranging from 1% — 5.25%), I came to the decision to take the DIY approach.

personal finance fintech dilbert
Fees on Fees on Fees on Fees…

If the months that followed, I received phone calls, emails, and invites to hear the latest sales pitch from the financial advisors that I spoke with previously. Each time, I would politely decline only to receive a follow up a few months later. Then I happened to read a post by Financial Samurai on questions to ask before hiring a financial advisor. After reading this excellent post, I decided to modify the list of questions and use it as a filter for any financial communications that I would have going forward.

As a software developer, IT consultant, and current student of machine learning, I see the most problems through the lens of classification or regression. The issues I was having the constant emails and phone calls was in my view a simple classification problem: where these financial advisor a) upstanding and noble advisors who had my best interest at heart, or were they b) untrustworthy at best and should not be within 1,000 ft of my money. How they responded to my questions would give the answer.

Note: Needless to say, not a single advisor has provided an answer to these questions nor have I had any follow calls or emails since sending the questions below.

  1. Are you a registered investment advisor (RIA)? An RIA has a fiduciary duty to do what’s best for their clients. RIA is different from a broker-dealer.
  2. How long have you been a financial advisor?
  3. What are your credentials? (undergrad, graduate school, certifications, online presence)
  4. Do you believe credentials matter if one has proven they can properly manage their finances over time?
  5. How long have you been in your current job?
  6. What were you doing before your current job and how long were you there?
  7. How are you incentivized?
  8. Give me an example of where you helped turn around a client’s financial situation for the better.
  9. What is your fundamental belief on asset allocation? How often? Why should we do it? What signals do you use?
  10. How would you go about building the right investment portfolio for someone 5 years, 10 years, 15 years, 20 years, and 30 years from retirement?
  11. If history has shown time and time again that the majority of active fund managers underperform their benchmarks, why do actively managed mutual funds still exist?
  12. What is your current outlook for the housing market and why?
  13. Where do you see the 10-year risk free rate going over the next several years and why?
  14. What do you think is the proper withdrawal rate during retirement?
  15. Do you think annuities a good idea for someone my age with my income stream and assets?
  16. Why do so many people bash whole life insurance policies?
  17. What is the S&P 500 currently trading at in terms of forward P/E and why do you believe the earnings estimates are achievable?
  18. Where do you see the S&P 500 or Dow Jones over the next 12 months, 24 months, and 36 months and why?
  19. If there’s a mile-long track and you completed the first lap at 30 mph, how fast do you have to go on the second lap to average 60 mph?
  20. Please explain why you are different from other financial advisors?
  21. What is an area of weakness you need to work on, and how do you plan to get there?
  22. What was your biggest financial mistake and how did you recover?
  23. Why do you think people spend more than they earn?
  24. If you were not a financial advisor, what would you be?
  25. What is the best means of communication?

Tech Advisor: Meeting the Challenges of the Modern CIO

In many Chief Information Officer (CIO) organizations, there is a perception by customers that CIO capabilities can be very limited. In these types of environments, information technology (IT) is viewed more as a cost than a strategic investment. In these cases, customers may only work with the CIO organization for network issues of email problems. To the customer, the CIO may meet their expectations in dealer with an issue, but falls short in providing continuous strategic value. However, the modern CIO can take a lead role in changing that limited perception, moving the organization toward fully leveraging IT to provide real strategic value to the enterprise.

Meeting the Challenges of the Modern CIO (PDF 1.37 MB)

Tech Strategy: What’s Holding Back Your Digital Transformation


For the last 15 years, I have focused on identifying and building new solutions that solve unique problems for public and private sector organizations. In that time, I have come across many obstacles causes gaps and finger-pointing between business and IT teams. Many of these gaps have delayed or impeded progress, thus causing quite a bit of pain for team members, stakeholders, executives and even customers as progress isn’t being made on the tasks at hand. Below I outline the six reasons I believe are the top contributors to the ever growing gap between business operations and IT that are possibly holding back you and your company’s digital transformation goals.

digital transformation
The Land of Digital Transformation Utopia

1. Conflicting Objectives and Strategies

In most large organizations, IT and other company business groups evolve in separate but necessary directions in order to accomplish what that division is tasked to. The IT group focuses more on the basic IT hierarchy as it relates to the needs on the overall business (network, security, email, hardware, software, back and front office, etc.). Business groups evolve to solve the needs the customers (marketing, products, services ¬– e.g. consumer value). Based on this simple description, it would seem that both groups work together in a sort of layered or tiered model, with IT supporting the business and business supporting the customers. In reality, this is usually not the case. What you often find are silos where everyone is working on their own projects with little collaboration with other groups.

Business teams normally look for an opportunity in the market to increase revenue, decrease costs, or improve performance. This can take the form of a new or improved product or service. It can take the form of automating previously manual processes, or it could simply be to phase out redundant or legacy solutions.

IT teams normally look to balance IT stability with incremental improvements to their tech stack. This is where the divergence rears its ugly head and we begin to hear rumblings about IT holding the business back from its digital dreams. This stability is necessary in a functioning organization and without it there would be chaos and constant executive escalations.

2. Different Priorities

Business and IT inherently have different priorities given their perspective with the organization. IT’s basic function is tech stability whereas the business is focused on bringing new revenue and even disrupting current tech to make way for innovative ways to serve customers. This is where we typically see conflicts with the organization with finger-pointing on failed or delayed initiatives (“IT is holding us back” or “the business needs to understand this IT program is a critical initiative”). So how do we bridge the divide with not only different, but also conflicting priorities?

This is where strong digital project managers (PMs) can provide the most value as they have the deep technical experience and strong understanding of the needs of the business come in handy. Digital PMs are able to accomplish this through hands-on working sessions using the “post-it note” process to digital portfolio reviews that include stakeholders from both the business and IT to ensure priorities are aligned. There are many are tools that are available to digital transformation teams to bridge the gap which I plan to discuss in future posts.

3. Different Definitions of Measurement

Having spent a number of years in IT before moving on to management consulting and digital marketing of enterprise retail, I understand that different groups across an organization will define and measure success based on their own objectives within the organization. The IT team normally measure success in terms of the technology (uptime, page speed, bps) or project implementation (time, budget, scope). The business teams attempt to measure success in terms of business drivers cost reduction, revenue, leads, and profit. However, when IT and business groups come together to achieve a common goal such as digital transformation, their needs to be common criteria to define and measure success. From cloud migration to API implementation, success lies in the initial rounds of communication can ensure that end goals and KPIs are met.

In order to achieve communication success, the best approach is to properly onboard all necessary teams to the project so that they understand the business drivers of the project and can define IT metrics that can be tracked and support the overall initiative. For example, if the business driver is to increase customer account registrations by 50 percent over the next six months, IT would be expected to deliver a solution that removes a friction to the sign-up process (showing an increase in sign-up completions) and has been deployed to production (well before six months). Too often we see IT teams come to the table with a solution that takes six to nine months for implementation and is not focused on the business value (increased sign-ups in this example). By using an onboarding approach, both business and IT can have alignment on what is important (KPIs related to what should be tracked and measured).

4. Lack of Customer Understanding

Have you ever filled out an online survey or given feedback on the user experience on a website? If so, there is a very high probability that your feedback was presented to a few stakeholders in marketing, but never made it past that single presentation. When the planning for the next redesign or product iteration begins, all of that valuable customer feedback is either forgotten or deprioritized in favor of other stakeholder requests (executives, senior managers, and more). What is needed to solve this problem is a simple process to ensure that customer feedback flows into the release planning for the future enhancements. If these are paying customers, then their feedback should get pushed to the top of the list at least for a proper review.

5. Too Many Silos and “Fiefdoms”

Maybe it is my background of working with the military and law enforcement throughout my career, but I found myself accustomed to always have a senior officer, commander, or even civilian manager that could resolve disputes between two different but equal groups. In the private sector, this is a luxury that I sometimes miss dearly. The many siloed organizations; the fiefdoms that spring up to protect a manager or executive’s personal priorities are the very obstacles that block true digital transformation as these fiefdoms fight progress for the whole in favor of the status quo for the few. Until these silos are knocked down, true progress cannot be made to bring an organization into a digital 21st century. In many cases, the only option is to spin out a “tiger team” that is completely separate from the larger organization to is then capable of delivering the true promise of digital transformation.

6. Access to Data and Services via Simple/Easy-to-Use APIs

In looking at the success digital and tech projects that I have led and been at part of throughout my career, I can see a common thread across all of them: access to data via easy, simple APIs. This allowed our teams to quickly prototype ideas throwing out the bad and keeping what works for continual improvement. The APIs were available with simple web-based documentation, there was no need to set up a project to access the API, and there were no “gatekeepers” exercising an API tax (this is more common in larger organizations and one of the main causes of failed integration projects).

There are quite a few API solutions that are available that make this digital transition APIs to easier. But first there needs to be a top-down directive that all data within the organization will be accessible via API and there will be no “walled gardens” or project “taxes” to access these APIs. Amazon took this approach in the early 2000’s and we see the results. I am ended this post on this topic and the outline of the Jeff Bezos’ directive because I believe this is most critical point to digital success:

All teams will henceforth expose their data and functionality through service interfaces.

Teams must communicate with each other through these interfaces.

There will be no other form of inter-process communication allowed: no direct linking, no direct reads of another team’s data store, no shared-memory model, no back-doors whatsoever. The only communication allowed is via service interface calls over the network.

It doesn’t matter what technology they use.

All service interfaces, without exception, must be designed from the ground up to be externalizable. That is to say, the team must plan and design to be able to expose the interface to developers in the outside world. No exceptions.

Anyone who doesn’t do this will be fired.

I will borrow one final bullet to this list from Steve Yegge’s Google Platform Rant that I believe is critical for anyone that reads this post, works in an organization that has not begun it’s digital transformation (or in the midst of transformation), and does not feel a sense of urgency:

I’m not saying it’s too late for us, but the longer we wait, the
closer we get to being Too Late.

Public Strategy: 2nd Amendment Will Never be Abolished in the US

Let me start by stating that I am a gun-owner and I believe in the right to bear arms. As a management consultant and digital technologist, I have developed a reputation for solving complex problems for public and private organizations. One of first things I look to do before diving into problem-solving mode is to identify and remove any obstacles that may block progress to finding a solution. I see this topic as an obstacle to solving real problems in this country and why I felt the need to write on this subject.

Every election cycle, we frequently hear conservative politicians, interest groups, and the media repeat the same line in every election cycle, liberal politicians will abolish the 2nd Amendment and only conservative politicians will protect the 2nd Amendment. This simplistic line is the one of the most predatory and insidious disinformation campaigns to ever be used on the public and is never combated effectively or explained to the uninformed citizen and voter. My goal with this post is twofold: 1) to explain how the U.S. Constitution is amended; and 2) to discuss why the 2nd Amendment will never be abolished in the U.S. As you will see, the U.S. President CANNOT:

  1. Abolish amendments via executive order
  2. Propose an amendment
  3. Vote on amendments.

The U.S. Constitution was created by the Founders to be extremely difficult to amend and change by future generations. Article 5 outlines the 2-step process to amend the Constitution: proposal and ratification.

Proposing an Amendment to the U.S. Constitution

The first option to amend the Constitution is that U.S. Congress (House of Representatives and Senate) can propose an amendment with a two-thirds majority vote. This is how all existing amendments have been proposed. Given the current politics in 2016, there isn’t a snowball’s chance in hell that this would happen. The GOP has a majority in the House and Senate, so it is extremely unlikely that the Republican-run Congress will propose and amendment to abolish the 2nd Amendment.

public strategy congress

The second option to amend the Constitution is that two-thirds of the states can call on Congress to hold a Constitutional Convention. With 44% of U.S. states having gun ownership rates of between 43% and 63%, this route to propose the abolishment of the 2nd Amendment is also extremely unlikely.

Throw in the fact that the NRA has given close to $22.5 million to politicians since 1990 and you can only come to the conclusion that abolishing the 2nd Amendment will never happen (at least in our life times). However, let’s play devil’s advocate and assume that by some stroke of chance, either Congress or the States manage to propose the amendment, the next step is Ratification.

Ratifying an Amendment to the U.S. Constitution

Once an amendment is ready to be ratified, how it was proposed (Congress or the States) doesn’t really matter; ratification can only be done through the States via one of two options: 1) three-fourths of states must approve the amendment via their state legislatures; OR 2) three-fourths of states must approve the amendment via ratifying convention.

Again, we are back to the reality mentioned above that 44% of U.S. states have gun ownership rates of between 43% and 63%, so there an almost zero chance that any amendment that comes close to abolishing the 2nd Amendment would ever be ratified by three-fourths of U.S. States. Not to mention that the 18th Amendment puts a time limit of seven years for states to ratify an amendment.

As you can see, the processes put in place by the Founders ensure the Constitution cannot be changed by the whims of a simple majority or current events. Not even a President has the power to take away your right to bear arms or any other rights guaranteed under the Constitution.

So the next time you hear a politician or talking head making claims about an opponent taking away your guns, just know that:

  1. They are LYING to you;
  2. They have NO CLUE what they are talking about;
  3. They want your VOTE; or
  4. They want your MONEY.

In closing just remember, no matter who is elected President, YOUR RIGHT TO BEAR ARMS WILL ALWAYS BE SAFE IN THE U.S.A.!


Daniel is a digital consultant specializing in IT advisory on technology strategy, investment, and implementation. He helps companies solve complex and strategic problems across multiple industries and domains. His drive to find solutions for clients and attain personal growth for himself are what keeps him at the forefront of innovation and helps him guide teams and organizations to cultivate amazing products and services. Given his thought leadership, engineering experience, innate ability to build relationships, and cultural interests, it’s not surprising that Daniel has been described as having “the mind of an engineer and the soul of an artist.”

Currently, Daniel oversees the Toyota Motors North America account for Beyondsoft Consulting. As Account Director, he identifies opportunities for new products, investments, and acquisitions in cloud, digital marketing, big data, and analytics. As a thought leader, he provides executives with strategy recommendations and effective solutions to core technology problems.

Tech Strategy: People Process Technology Strategy for Enterprise 2.0

Most people think of Enterprise 2.0 of Enterprise Collaboration as a particular set of technologies, such as blogs, wikis, and profiles. Others describe it as simply the ability to share information or knowledge within the enterprise. However, these definitions are inadequate–Enterprise 2.0 is the ability to leverage business and IT strategy together to increase the effectiveness and efficiency of technology initiatives. Therefore, to establish Enterprise 2.0 means organizations must choose and measure IT projects on the basis of three criteria: 1) does it increase revenue, 2) does it cut costs, and/or 3) does it increase performance. Enterprise 2.0 is not simply a series of technology tools, but a transformation of the enterprise mindset to build strategy to address business requirements that realize cost savings, performance improvement and if possible, new innovative sources of revenue.

People, Process, Technology Strategy for Enterprise 2.0 (PDF 1.04 MB)