West Stringfellow of HowDo: “Customer Obsession”

“A lot of good ideas simply fade away.” — Andy Warhol. As an innovator I’m full of ideas I think are good. However as an entrepreneur I know that I have to fall in love with solving customer problems for profit, not my ideas. Therefore I look for the intersection of my “good ideas” and real customer […]

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“A lot of good ideas simply fade away.” — Andy Warhol. As an innovator I’m full of ideas I think are good. However as an entrepreneur I know that I have to fall in love with solving customer problems for profit, not my ideas. Therefore I look for the intersection of my “good ideas” and real customer problems. These intersections have given me the greatest satisfaction in my career. Also, they have proven to be among the most lucrative ideas I have.


As part of my series about the “How Businesses Pivot and Stay Relevant In The Face of Disruptive Technologies”, I had the pleasure of interviewing West Stringfellow, Founder and CEO of HowDo.

West Stringfellow is the Innovation Expert & Founder of HowDo, a free self-guided innovation training that combines 20 years experience innovating at Amazon, PayPal, Rosetta Stone, Target, Visa and a bunch of startups with 40,000 hours research into innovation best practice.


Thank you so much for joining us in this interview series. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I grew up in Boulder, Colorado and loved being outdoors. We lived on a ranch with cows, goats, dogs and cats. I used to set up a tent and sleep in the field with the cows in the dead of winter just to be outside. When I started working full-time in highschool, all I wanted to do was be outside.

My first job was as a Junior Ranger in the Mountain Parks Division of Boulder County. My fellow trail crew members and I installed many of the rock steps on the Third Flatiron trail. I lost the end of my thumb installing one of those rocks. I then went into construction, framing houses deep in the mountains. There I received a traumatic brain injury when a truss broke loose from a housing frame and hit me in the head. After my second major injury, I decided to find work indoors. And that’s what led me to discover my love for computers and problem solving.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

During my first year of college I really wanted to be a lawyer. Accordingly, I pursued a law firm in Denver (JCFKK, LLC) for a summer internship. They ended up giving me — a college freshman — the legal internship that was normally reserved for students in law school. I knew by the end of my first day that I didn’t want to be a lawyer. Unfortunately I had a three-month unpaid internship ahead of me.

I showed up every morning around 8AM and left right at 5PM, spending all day filing files and searching for files that were misfiled. Everyday I spent three hours on a bus from Boulder to Denver and back. On the bus ride I thought about how much I hated my job. It was so upsetting to me that I was spending my summer indoors looking for documents which were simply misplaced.

Perhaps a Partner left them in his or her car. Maybe a Paralegal was holding them at their desk. Maybe the documents were still on the shelf — just not where they should have been. After a few weeks of bus rides I couldn’t take it anymore.

I went to the library and asked the librarian how they kept their books organized. The librarian showed me their Library Management Systems (LMS) on the computer. After a ton of research, I figured out how to build an LMS using Microsoft Access.

I took this solution to the Partners and they loved the idea. They gave me a little office space where I could organize everything. I even got my own computer — a big deal for unpaid legal interns in 1997. I started driving myself so I could show up early and work late to build the system while still managing their files. At the end of the summer, they surprised me with a 3,000 dollars check. At the time, three thousand dollars was MASSIVE.

Through that experience I learned that

1) It is OK to speak up about problems if you also present a solution.

2) I enjoy learning new things and solving problems more than I enjoy mundane or repetitive tasks.

I carry those lessons with me to this day. Consequently I have proposed and built new solutions at every company that I have worked for including Amazon, PayPal, Rosetta Stone, Target and Visa. As a consequence I have received several patents. I love solving problems. It is truly what I love to do.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My dad had the largest impact on my career. He was a strict and tough disciplinarian who saw more potential in me than I saw in myself. He was also a successful entrepreneur who was deeply respected in his industry. If it wasn’t for his toughness when I was young, I don’t think I would have had the motivation and resilience to work as hard as I did to climb the corporate ladder.

As soon as I became an entrepreneur and sold my company things changed between us. He stopped being the disciplinarian and started being my friend. We started having lunches and dinners together several times a week. Ultimately he asked me to be the officiant at his wedding. Unfortunately he was killed in a car accident while driving to the wedding a week before Christmas in 2019.

After his death at least 30 of his industry peers proactively reached out to me to share how much he changed their careers and lives. I learned that he was their surrogate father, their mentor or just a person who really helped them. He was widely regarded as the most trusted person in his industry and was always known to do the right thing. It was overwhelming learning how much he was respected. I remember thinking to myself: “Damn, dad had some next-level game at work that I never knew about.” This awareness set a new bar for what I want to achieve in my career. Game on, dad.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

I started HowDo with the simple vision to teach the world to innovate. Innovation is the discipline of solving problems. The world is filled with problems. On the other side of every problem is a solution. Innovation will be used to find these solutions. I will teach every aspiring entrepreneur and innovator how to succeed in finding these solutions. It’s my life’s mission.

I started on this mission during the 2016 US Presidential race. It was then that I awoke to the division in America. To better understand what was causing the division, I hired a team of researchers who created an unbiased compilation of facts around each Presidential candidate’s platform. I shared our findings on LinkedIn if you’re interested.

The facts demonstrated that the division in America is built on an expensive education system, unaffordable housing, a lack of quality jobs, inadequate healthcare and a systemic lack of equal access to opportunity, justice, progress and wealth.

I love America. It broke my heart to see so much pain stemming from structural barriers that prevent people from achieving the American dream. My life has been filled with privilege and it was jarring to measure the disparity between my experience and others who did not have access to the opportunities I did simply because of the circumstances they were born into.

America was built for the people, by the people. I’m one of those people and felt like it was my patriotic duty to help as many people as I could with the skills and resources I had at my disposal.

My career and travels took me to 38 countries and allowed me to live and work overseas for over eight years; so I expanded the scope of our research to include other countries. Like America, many other countries around the globe are experiencing rising internal division, increasing isolationism and xenophobia, extreme wealth inequality, government corruption, corporations that are too powerful and a climate crisis that is already impacting everyday life. And that was before the pandemic.

As an American patriot, a citizen of Earth and a fellow human being, learning all this meant I could not go back to “business as usual”. The stark reality of our world changed my mindset about what I want to achieve in this life. Therefore I set out to change the fundamentals of business.

So on the eve of 2017 I publicly committed to sharing everything I know. Four years, 500K dollars+ of my own money, 40,000 hours of research and 1,000 pages of writing later, HowDo was born to teach the world how to innovate.

Thank you for all that. Let’s now turn to the main focus of our discussion. Can you tell our readers a bit about what your business does? How do you help people?

HowDo is free, self-guided innovation training that teaches anyone to identify, build and grow tomorrow’s solutions while driving empowerment and equitable employment for all.

HowDo prepares innovators and entrepreneurs to work through the boredom, frustration, fear and resilience that is required to be great at problem solving. We then teach people how to build a robust strategy based on facts. Once they have a strategy, we teach them how to use innovation’s primary tools: product management, accelerators, incubators, mergers and acquisitions and corporate venture capital. None of this can be achieved without an awesome team, so we share how to build, manage and scale a team that is capable of successfully innovating.

Which technological innovation has encroached or disrupted your industry? Can you explain why this has been disruptive?

The biggest technical innovation I have seen disrupt business is the rise of social media and the ability for anyone to amplify their voice. While there are hundreds of millions of aspirational influencers, there are very few successful knowledge influencers.

I define knowledge influencers as those who are disrupting knowledge industries by leveling the playing field and empowering everyone with their insights and best practices. I believe knowledge influencers will be the next major category of influencers. They will disrupt the 160 billion dollars worldwide management consulting market and most of the advertising / agency market that’s responsible for 138 billion dollars in revenue in the US alone.

I’m learning all the hard lessons associated with being a category pioneer on social media. Accordingly, I will share everything I learn about how to become a knowledge influencer. My goal is to tear down the structures that prevent access to essential knowledge so that everyone has the information required to ideate, build, scale and sell businesses.

What did you do to pivot as a result of this disruption?

As a result of the inevitable disruption in the knowledge economy, I stopped caring about the value of my knowledge and started giving away everything I know and can afford to research.

Was there a specific “Aha moment” that gave you the idea to start this new path? If yes, we’d love to hear the story.

My “Aha moment” came while I was building “Goldfish,” the codename for the company I was building at Target as an Entrepreneur in Residence (patent here). My team and I spent a lot of time researching and building products for social media influencers. At the same time, I was Target’s VP, Innovation and leading the Techstars Startup Accelerator I proposed and built at Target. It was an incredible opportunity to build my own startup, lead innovation for 300K+ employees and 70 billion dollars in revenue and coach an incredible cohort of startups from around the world. I loved nearly every second of it. I started thinking: “How can I do this forever?”

Then Target shutdown Goldfish for reasons entirely unrelated to my company. The way that decision was handled and the impact to the people who trusted me with their livelihoods shifted my whole world view. Seeing the faces and feeling the emotions of my Goldfish team was too much for me. I lost faith in corporate America and vowed to never again allow anyone to impact my team that way.

The timing was tremendously auspicious as I had just publicly committed to sharing everything I know for free in an attempt to heal the division in America. Between dealing with more corporate bullshit or risking going broke trying to save the world, I chose the world.

So, how are things going with this new direction?

Things are going really well. I just launched our new website and curriculum. Without any advertising dollars, HowDo has had over 400K readers from every country and territory on Earth. There was a 30-day period where readers read HowDo’s content for 90 days worth of time. That’s 2.1K hours of reading HowDo’s content in 30 days. I’m excited to see what happens when I launch the V1 website, the video training series and start openly discussing what I’ve created over the last four years.

Can you share the most interesting story that happened to you since you started this pivot?

The most interesting thing that has happened to me is that every week people I’ve never met and who live all around the world are reaching out to me to tell me that HowDo is helping them. I love meeting HowDo’s customers, hearing how HowDo helps them and learning what I can do to improve HowDo for them. Hearing that my work and mission legitimately helps others makes me feel better than making millions of dollars ever did. It’s the best form of payment I’ve received in my career.

What would you say is the most critical role of a leader during a disruptive period?

Disruptive periods are time when the power dynamic should invert: the C-suite should become very responsive to the employee and customer. But so often in disruptive periods, investor portfolios get squeezed and they start to put pressure on the C-suite who passes that right onto the employee and customer.

Therefore the critical role of a leader during a disruptive period is listening to the customer and the employee while protecting both from the bullshit that is bound to roll down from the C-suite who’s just passing on the pressure they are getting from investors.

When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

When the future is uncertain and a leader’s team needs inspiration, motivation and engagement; the best way for a leader to boost morale is to help their team find balance and lead by example.

This is an extremely traumatic time for everyone. Social isolation is causing a legitimate mental health crisis for individuals, families and teams. At the same time, there’s an economic depression in the service industry and a protracted recession in the real economy which creates a financial pressure cooker for most people. It is also creating the greatest inequality ever recorded. In addition, we’re obviously experiencing a deadly global pandemic that is killing or maiming our loved ones on a daily basis. These extraordinary circumstances are paired with the most social and political division in America since the Civil War.

Everyone needs more time and space than is normally required for self-care and family-care. Leaders must help those they lead find this space. That means creating greater work-life balance. It means giving employees freedom and flexibility to adjust their work schedules to accommodate life’s new demands. Likewise it means providing employees with access to and support for mental health services so that they can heal from this collective trauma.

Leaders must lead by example and take this time for themselves. Otherwise, leaders are implying to their employees that taking time is not needed. It’s hard for leaders to be vulnerable. But now is the time to lead with vulnerability and empathy. Leaders who set the example in their own lives and lead their teams with empathy will scale. Leaders who pretend that “business as usual” is a thing right now will leave a lasting legacy as the assholes they are.

Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

The number one principle that can help guide a company through the ups and downs of turbulent times is “obsess over your customer”.

Every minute of the work day should be focused purely on solving clearly defined customer problems. If you are not working on a defined customer problem — stop working and start learning about your customers. Define the metrics that matter to the customer, understand and distribute relevant customer data and make all decisions based on customer data. Use this data to identify and capture the greatest customer opportunities and identity and solve the largest customer problems.

Can you share 3 or 4 of the most common mistakes you have seen other businesses make when faced with a disruptive technology? What should one keep in mind to avoid that?

The most common mistakes I have seen businesses make when faced with disruptive technology are:

  1. repeating other businesses’ mistakes,
  2. ignoring massive opportunities despite there being irrefutable market evidence of the presence of an opportunity, and
  3. not giving their team time and permission to engage in self-directed learning; which is the cause of mistakes 1 & 2.

The education system teaches students to parrot information, not learn for themselves or teach themselves. Therefore, the basic instinct of high school and college graduates — aka: today’s employees — is to ask a question because a teacher will provide an answer. Businesses reinforce this behavior. The basic lesson a vast majority of employees are taught is to “ask for help.” These lessons must be untaught if we hope to create successful businesses and businesspeople.

Successful businesses and businesspeople have a relentless sense of urgency to acquire knowledge. They know that this knowledge will become their edge — their primary competitive advantage — against incumbent and nascent competitors. Successful businesses encourage employees to think and learn for themselves. They dedicate themselves to just one thing: solving customer problems for profit. To be successful at this, they must encourage every employee to work through the boredom, frustration, fear and resilience that is required to be great at problem solving. Problem solving is the process through which knowledge is gained. If you’re not solving problems, you’re not really learning.

Those in business who become great at solving customer problems for profit consistently outperform their peers. Those who focus on the status quo fail.

Businesses that succeed create continuous learning paradigms where they relentlessly study the customer and their business. There is a treasure trove of publicly available and easily accessible data from which we all can learn about the efficacy of past decisions, existing companies and emerging technologies.

I encourage everyone to block time in your day — at least 30 minutes a day — to learn from these sources. It’s amazing what you’ll find with just a little bit of effort. At first this may slow you down — but over time you will move with greater efficiency, more efficacy and the confidence that you are aligned with customer needs and market realities.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to pivot and stay relevant in the face of disruptive technologies? Please share a story or an example for each.

1. Customer Obsession — Amazon

It’s a short story: in 1997 Jeff Bezos wrote a letter to shareholders saying that he was going to focus on the long term and obsess over the customer, not quarterly earnings or Wall Street’s profits. Bezos also made “Customer Obsession” Amazon’s #1 corporate value. He’s now the richest business person on Earth. Likewise Amazon is consistently among the most valuable companies on the planet with one of the highest P/E multiples of all time. Customer obsession is how disruptive technology is created. If a company wants to survive disruptive technologies, they must be the disruptor.

2. Customer Obsession — Bonobos

Bonobos was founded by Andy Dunn and Brian Spaly when they noticed how hard it was for men to find a pair of pants that fit. The brand began as an online retailer that was later bought by Walmart in 2017 for 310 million dollars.

According to Casey Drake, writer for Endear:

“From day 1, Bonobos vowed to take a different approach to their business model. Instead of investing money in traditional marketing methods, they instead invested in their customer experience and success teams. What resulted was a cult following willing to buy in to whatever new interesting concepts the brand would try.”

Dunn described their approach as “maniacally focused on the customer experience and interacting, transacting, and story-telling to consumers.” The company’s popularity grew through word of mouth driven by brand loyalists.

3. Customer Obsession — Warby Parker

Another brand that focused on customer centricity is Warby Parker, the online retailer of prescription glasses and sunglasses founded in 2010 by Neil Blumenthal, Andrew Hunt, David Gilboa, and Jeffrey Raider, four students from Wharton. Described as “the most innovative startup of America” by Yashica Vashishtha, writer for YourTechStory, the four entrepreneurs introduced stylish customized eyewear to the online consumer.

Warby Parker’s competitors were Luxottica and LensCrafters. Luxottica sold stylish eyewear, but the prices were high end, and Lenscrafters lacked any sense of style in its branding. Warby Parker’s eyewear were appealing, affordable, and customers enjoyed the convenience of trying on up to five pairs in the comfort of their own homes. According to Gilboa, one of the cofounders, “The idea was really based on two simple premises. One is that a pair of glasses should not cost more than an iPhone, and two, that eyeglasses could effectively be sold online.”

The niche product gained immediate traction and further gained popularity after Vogure covered the Warby Parker’s story within the first year of its launch. The brand exuded trendiness, style, and a dash of exclusivity while also being universal. Warby Parker’s branding and customer-focus built a defensive wall that protected them from competitors and other eyeglass manufacturers.

Warby Parker has now gone onto launching physical stores and built its own manufacturing capabilities in an optical lab located in Rockland County, New York. In 2018, the company was valued at around 1.75 billion dollars making it one of the most successful direct to consumer brands in the world.

4. Customer Obsession — Casper

Another brand that used customer experience to disrupt a traditional retail industry is Casper, an online retailer of mattresses and sleep products. Casper achieved the extraordinary feat of persuading customers to buy a mattress online without first touching/feeling the product. It seems rather counterintuitive that buying a mattress without first trying it would be in the customer’s interests because who wants a mattress that is too hard, too soft, and not just right?

But that was the whole point. Casper, through smart marketing, gained the trust of the customer to such an extent that they were willing to entrust Casper with the responsibility of choosing the right mattress for their needs, saving them a whole lot of time and trouble. Using data on actual experiences and customer reviews, 75 dollars gift-card referrals, plus a 100-day guarantee, Casper found the customer’s pain point and fixed it. Ultimately, Casper built a relationship with the customer and made sure they were educated on their potential purchases, giving them peace of mind — a huge factor for big-ticket items.

5. Customer Obsession — The New York Times

In the case of The New York Times, Wei Yiyang, Wang Duan, and Ren Qiuyu of Caizin news wrote that the Times “worries that a third-party mediator will alter the relationship with users.” Apple News+ is a closed system that protects user privacy because Apple can see how many clicks an article received but not who reads it. Apple prevents advertisers from tracking user information, and content providers are also blocked from learning about their readers. This all means that it is harder for media like The New York Times to gain subscribers through Apple News+.

“We want to be able to email our users and develop a relationship with them. And we don’t really want anyone between us and that,” said Mark Thompson, CEO of The New York Times.

The message here is that if you don’t want to be disintermediated, you need to think about maintaining a relationship with the customer in the face of all these platforms and commodity brands. You must build and strengthen the relationships you have with the customer. Some of it is building loyalty, some of it is building new channels and incentives to connect directly with your customers, some of it is changing the brand and the product, and some of it is changing the price point. But all of it involves customer obsession.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“A lot of good ideas simply fade away.” — Andy Warhol. As an innovator I’m full of ideas I think are good. However as an entrepreneur I know that I have to fall in love with solving customer problems for profit, not my ideas. Therefore I look for the intersection of my “good ideas” and real customer problems. These intersections have given me the greatest satisfaction in my career. Also, they have proven to be among the most lucrative ideas I have.

How can our readers further follow your work?

Thanks for asking! It’s a great time to follow HowDo. I’m currently preparing to launch an entirely new and significantly upgraded website, updated and more comprehensive training and a video series that translates the entire 1,000 pages of writing into video. HowDo will teach you how to be an entrepreneurial innovator for free!

Please follow HowDo on your preferred social media platform: Facebook, LinkedIn, YouTube, Instagram and/or Twitter. Please note that these channels are quiet for now as our official launch is a few weeks out. If you prefer to receive emails, please visit https://howdo.com and submit your email address in the footer. We will not spam you. HowDo will only send you emails as the curriculum, corpus and product evolve.

Thank you so much for sharing these important insights. We wish you continued success and good health!

Thank you so much for the opportunity! Best wishes and good health to your team and readers!!! Wishing you all peace and love in these unique and challenging times. ✌️♥️ — West


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