#BeBetter Podcast with Michael Kurland

Empathy and Innovation Can Change the World with West Stringfellow

Iteration and a Can Do Attitude Drive Lasting Change

West Stringfellow leads product management and innovation at scale. Currently West is Founder and CEO of HowDo where he is providing free universal innovation training and an EHF Fellow. In today’s show, West shares his inspiring journey and why he believes that any problem can be solved through innovation, and a dedicated tribe of people who support your vision.

West Stringfellow portrait

“I truly believe that without innovation, without a whole range of new products, we’ll never be able to fight climate change, eliminate inequality, and we will steer humanity in the wrong direction.”

—West Stringfellow

36. Empathy and Innovation Can Change the World with West Stringfellow

Key Takeaways

  • Failure is the decision to stop iterating.
  • Showing up every day for your team is the most important thing.
  • Take what you know and share it with the world.

Social Links


West Stringfellow leads product management and innovation at scale. Currently West is Founder and CEO of HowDo where he provides free universal innovation training and an Edmund Hillary Fellow. Prior to HowDo, West was Target’s first Entrepreneur in Residence, Target’s VP of Innovation, and the Founder of the Techstars Retail Accelerator, in partnership with Target. He was also Chief Product Officer for Bigcommerce and Rosetta Stone, led product innovation at PayPal and Visa, and was a senior product manager at Amazon. As a result, West led teams that built and rebuilt products and services used globally and daily by tens of millions of satisfied customers.

Throughout his 20 year career, West honed his ability to quickly create a better strategic vision of a company’s future, motivate large groups of people to pursue that vision and then lead teams through the operational, financial, organizational, and technical processes that bring strategic visions to life. Now he’s giving away everything he learned on HowDo.com.

“If you take care of the capital and not the team, you’ll lose the team. If you take care of the team and not the capital, you’ll get more team.”

—West Stringfellow

Podcast Transcription

Hello. I’m Michael Kurland, CEO and Co-Founder of Branded Group. Welcome to the #BeBetter Podcast. To me, our company’s mantra to “Be Better” is more than a tagline; it’s a culture that permeates our organization, propelling our team to Be Better to each other, our customers and our communities as well as to ourselves. Each week on the #BeBetter podcast, I interview leaders who authentically exemplify how they are being better in their professional and personal lives.

Michael Kurland (00:01):

Welcome to another episode of the #BeBetter podcast. I’m your host, Michael Kurland. Joining me today is West Stringfellow, owner of How Do and Human. Welcome to the show, West.

West Stringfellow (00:16):

Thank you for having me, Michael.

Michael Kurland (00:18):

Looking forward to having you. Tell the audience, first and foremost, a little bit about yourself and your company.

West Stringfellow (00:25):

Before I built HowDo, I spent about 20 years in Silicon Valley companies, startups and big companies, including Amazon, PayPal, Target, Visa, Rosetta Stone. I focused mainly on innovation and product management.  I was always, generally, put in roles where big change needed to happen quickly. Build new products. Build new teams. I was really fortunate in my career to learn from a lot of extraordinary people and get to do some pretty fun things. I love building things. I love solving problems. Now, I am sharing everything I learned and everything I could afford to research on HowDo.com for free because I truly believe that without innovation, without a whole range of new products, we’ll never be able to fight climate change. We’ll never be able to eliminate inequality, and we will steer humanity in the wrong direction.

Michael Kurland (01:22):

That is all very impressive. I was really excited to get you on the show. We met a couple of days ago and went over all the pre-show meet and greet, and your story is fascinating to me. I’d really like if you could take the audience through where you were when you did all this innovative work with Target, Rosetta Stone, Amazon, and PayPal, who you were, and what you were doing. Let’s build that up first and then let’s get to the tipping point as we get there. Then we’ll kind of go through the change of where you’re at now. Let’s do the lead-up first. Let’s talk about who you were for those years and what you really did and what was important to you.

West Stringfellow (02:13):

Fuck. [Laughing] It’s so funny. I don’t know if I would recognize myself if I met myself today. My dad was a really successful entrepreneur. He and I didn’t get along, so I left home young and alone. I worked my way through college. Got through college. I barely graduated, but I was super hungry in both metaphorical and physical ways. My whole goal in life was to get more, just more. I wanted more money. I wanted more power. I wanted more responsibility. I wanted more everything.

Michael Kurland (02:56):

Can I ask you a question? Was that to prove your dad? I’m worthy. I’m right. I’m better. That sort of thing?

West Stringfellow (03:06):

It’s funny.  At the time, I would have said absolutely not. Absolutely not. No, it is all about me being successful. Me. Me. Me. Me. Me. Me. Me. Me. Me. I have learned since then that, no, that’s completely false. Absolutely, I was very much wishing and wanting his approval. I didn’t know that until I got it. As soon as I got it, I felt a level of peace with myself that I didn’t know was possible, to be honest. It took me being very successful and developing the ability not to have to work from my success. My dad never believed it. Literally, he never believed some of the things that I accomplished. Some of these things I can’t talk about specifically in public. I had this one moment of incredible success where it was so good, in my opinion, that I thought I needed to share it with my dad. I had my dad written into the contract. He was part of the nondisclosure agreement so that he could actually see what I had done. When he saw that, he literally said, “I don’t fucking believe you.”

Michael Kurland (04:17):

West Stringfellow (04:20):

I’ll remember this forever. He said, “Way to go, man. Way to go.” My dad is not one to give compliments. Two years ago, on my last birthday when he was alive, my dad called. He always sings happy birthday with an Elvis voice. [Imitating Elvis, singing] Happy birthday, to you.

Michael Kurland (04:39):


West Stringfellow (04:41):

After that song, he said, “I got you a present. I’ve been thinking about this present for 6 months. It’s a compliment.” I said, “Man, this so you. You have to save a compliment for my fucking birthday. He goes, “You’re peaceful. You are in a maelstrom of shit, and you are peaceful. It is so inspiring to see that.” For me, that was the ultimate thing in life is to get my dad’s approval. Through years of therapy, I’ve learned that that’s a very important thing for me. Alot of that is built on trauma from my youth where we had some pretty traumatic experiences. As I grew older, that trauma wasn’t what drove me superficially. Superficially, I was driven by whatever story I was telling myself at the moment and whatever problem was in front of me and whatever opportunity was in front of me. Realistically, in reflection with years and years of intensive therapy [Laughing], I realized that a lot of it was driven by PTSD and me needing to really get the validation that I never got as a kid. Getting that stuff late in life really changed my perspective on the influences in my life. I started looking at why do I do things? Why do I feel things? What feelings do I have? Feelings were not a thing that I… No shit. I was married twice, and God bless the two people who agreed to marry me because I was a fucking asshole. Feelings were not a part of my thing. That was not part of me. If someone said, “How do you feel today?” I would be say, “What is this question? I feel like we need to move forward with whatever project we’re working. I feel like we need to hit the SLA. I feel like the KPI is not being hit and that’s fucked up. I feel like we’re crushing it. We’re crushing it. Let’s go party our asses off and have a shitload of fun because like we’re kicking ass.” Now, I would say, “I feel some apprehension about some of the health of the family members in my life. I feel happy about some aspects of my life. I feel like I could do better in other aspects of my life. I feel accomplished in many ways. I feel like I’ve not accomplished anything in more kind of meta and idealistic ways.”

Michael Kurland 07:10):

What I’m hearing you say is feelings, pre-tipping point of your life, got in the way, and you just didn’t have time for feelings.

West Stringfellow (07:19):

Correct. Again, this is one thing I learned through therapy. I had some pretty awesome- not awesome in the fun part of the word but awesome in the real part of the word- traumatic events when I was a kid. So much so that my therapist, when I was explaining one of them, he even exclaimed, “Holy shit, man. That is fucked up.” He literally called himself on it. He said, “Whoa. Sorry. Sorry. I didn’t mean to do that, but you should know that that is fucked up.” [Laughing] To me, that was my life. I didn’t know that that stuff was bad. I knew it sucked, but I didn’t know that it was- on a scale of events- I didn’t know it was out of bound or out of range. Feelings were not a thing because it’s just part of having my trauma. I suppressed any kind of emotion because if I started to feel happy, I started to feel sad. If I started to feel anything that was like a human emotion, it would call into question a lot of the numbness that I needed to stay in in order not to feel the pain that I was carrying. I just wanted to be numb. Eighty-hour, 100-hour, 120 hours weeks, those were fucking perfect. Blowing my brains out with whatever I could get my hands on the weekend; that was perfect. I realized, ultimately, that was just killing me, and I had to change completely.

Michael Kurland (08:57):

Wow. This is a good buildup. You were living this numb life, going from project to project and then partying hard all weekend because you didn’t want to deal with feeling anything, but you were so successful. I think this is very important to touch on. You were so successful in everything you did. Let’s talk about that real quick. What were you doing? Where did you make your mark that you were so successful that your dad finally told you that you were great, and you’ve made all your money? Let’s talk about that.

West Stringfellow (09:34):

I was really opportunistic when I was young because I literally needed money to eat and pay for housing and shit at 17, like many people do. There’s nothing spectacular about that. It’s pretty normal. I started working outside. I really wanted to be outside. That’s all I wanted to do when I was a kid. My first job was as a Park Ranger. I was in the mountain parks division, building trails, and a rock fell on my thumb and chops the end of my thumb off. Then I went into construction, and a trestle fell on my head. I got a traumatic brain injury. I said, “Okay. I’m going to go inside. It’s safer there.” When you get hurt in those kinds of jobs, you get workman’s comp, but that’s a tiny fraction of what you make. I was suffering economically when those happened and physically. I got a job at Starbucks and Subway. I got fired from Subway for showing up late because I was trying to study. Starbucks was super hard because I was trying to study. Then I got an internship at a tech company over the summer. This was 1997. Sorry, 1997 was the law firm internship. I was a Legal Clerk. I thought I wanted to be a lawyer. I ended up building them an LMS, the library management system, because they were constantly losing their files. I went to the Norlin Library at University of Colorado, and I said, “How do you keep track of books?” “I have this shelving thing at the office. How do you keep track of books because everyone loses shit off the shelf? You’re a library and you don’t.” They said, “Oh, we have this LMS.”  I taught myself Access. I built the LMS. I went from being a free, unpaid intern at a law firm to being a paid intern at a law firm just because I could do this computer thing. I said, “Whoa.”

Michael Kurland (11:32):

You were valuable.

West Stringfellow (11:34):

Right. They found value in computers. They said, “Whoa. You can do this?!” I said, “Wow. If you’re impressed by that and give me money, then I’m going to do more of that. From 1997 to 2004, I was a database administrator when databases needed babysitters. You’d get paged and go in and need to plug more in or unplug them so they could cool off. A lot of data normalization and data reconciliation and just really boring shit. I did that for SFA and CRM databases. I ended up doing it for NetLibrary and Alibris. NetLibrary was digital books and then Alibris was the largest used bookseller. I really was this weird expert on book metadata and the movement and kind of reconciliation of book metadata. At Alibris, I was living above this Chinese restaurant in Emeryville. I was right by the vent for the stove, so all of my clothes, my bed, my pillows, me, everything smelled like fried Chinese food. It was so bad. [Both laughing]We had 16 people that we integrated with. A lot of these were booksellers, and a lot of those booksellers don’t exist anymore. One of the clients that we integrated with last was Amazon Marketplace, when Amazon launched marketplace. Of course, Jeff Bezos started Amazon with books. He really cares about books. When he launched the marketplace for books, we really wanted to get it right. When I integrated with Amazon, I had already done over a dozen integrations with some of the world’s best booksellers at the time. Amazon’s API sucked, and I told them that. I said, “Hey, you are moving data in an extremely inefficient way. It’s going to fail in this way and when it does, you’re going to call me and ask me to stop sending your data,” and blah, blah, blah.

Michael Kurland13:42):

I just want to pause for one second. You literally told the most powerful retailer in America that their API sucked. That’s awesome.

West Stringfellow (13:51):

This was 2003. Alibris, at the time, literally thought they could beat Amazon. I was working at Alibris, this tiny little startup, and they said, “Oh, we will win against Amazon. There was AbeBooks in Canada, and they said, “We will win against Amazon.” They were real clear on that. When I integrated, I was quite cocky. I said, “Yeah, I’ve integrated with Barnes and Noble, Borders, Waterstones, Half, and E-bay. You guys suck. This is stupid.” I was moving, via FTP, flat files of text with 40 million rows. Any system’s going to choke on that. I don’t care how efficient you were. We didn’t have distributed Cloud systems where you could just expand CPU’s. Everything just choked on that.

Michael Kurland (14:44):

I just want to pause for one second for the millennials out there. We’re talking about servers. Nothing was in the Cloud 15 years ago. There was this big room in the back that had these huge machines that everything had to process through.

West Stringfellow (15:03):

I was at a rave in Soma [both laughing] in San Francisco. I was three sheets to the wind, for sure. My phone started blowing up, and it was my boss. He said, “I don’t know where the fuck you are, but you need to go to work,” so I did. I went to work, and the thing that I predicted would happen happened. On our end, we had to stop doing some stuff and change some stuff. Ultimately, I sent them an email saying, “You are not enabling us. We are the problem because you have made it a problem. Also, we have the most inventory, so we should be your best solution.” That sparked a conversation with Amazon where they asked me to come up to Seattle. I ended up meeting with Greg Greeley, most recently the President of Airbnb. I remember meeting Greg and just explaining, “This is how I think things should work.” He said, “Cool!” I flew back to Alibris that Monday, which was on a Thursday or Friday. On Monday, the CEO of Alibris came over and said, “Hey, I think Amazon’s going to hire you. I think you need to go.” I said, “Why would I go to Seattle? Why would I go to Amazon? We’re going to beat Amazon. What the fuck?” He said, “No. No. No. No. No. [Laughing] You need to understand that Amazon is pretty badass. At the time, I thought they were just kind of an annoying partner. I didn’t understand what they were doing. I got up there and I loved every second of that experience. They were so young at what they were doing, and they were doing so many new things every, literally, day. Jeff Barr was their AWS evangelist. When I joined Amazon, I couldn’t believe how much data Amazon had. One of the first things you did, at the time, was you had to kind of prove yourself on DSS and ETL so that you could run queries and understand what was going on. Those were internal systems to find data. Long story short, I said this data is fucking valuable. I went to Jeff Barr who, at the time, who was just a guy trying to figure out what Amazon could do in terms of exposing Amazon’s technical capabilities. I said, “Hey, I think we can sell data. I think there’s a lot of data that we can sell. In fact, it’d be really valuable to our marketplace sellers.” We ended up building the historical pricing API, which was Amazon’s first billable web service. I, ultimately, built Amazon’s digital video operations process. If you’ve ever watched anything on digital video, the initial build of that came from the team that I managed on the backend. There was a brilliant team. That was one of the first times I actually saw a major product build. They had this incredible team that was running what was called MIT, media and instructional technology. I’d never seen a team so powerful in terms of engineering. It was the first time that I really understood what real engineers were. I was a software engineer, database administrator kind of guy. They were actually software engineers who were just like unreal in terms of moving data and moving files in ways that I’d never seen.  I realized, “Okay. This is next level stuff. I’m completely out of my league. There’s no way I can compete with these people.” At the time, in 2005, there was this concept of a product manager, which was not a normal word at that time. It was not a job at that time. At Amazon, it was very much the CEO of the product. I wanted to do that. I wanted to be the CEO of a product. Ultimately, I was. I worked in fraud for Europe and affiliate marketing for Europe and then joined Visa. I joined as a consultant and, three weeks later, I was the Vice President of Innovation. I built their PayPal competitor. I went to Australia where I joined a group that was trying to turn from an auction model to a fixed price model and buyout a lot of the partners and sell the private equity. I helped them do that for a year. I joined PayPal as the head of Australian product and then became the head of innovation for products and then the head of platform for the company. I went to Rosetta Stone as Chief Product Officer. I went to Big Commerce and was Chief Product Officer.

About 15 years into my career, I was fucking burnt. I just needed space. I was completely out of my element at that point. You have these huge titles, huge roles. The way that I managed myself at that time, I would call a failure. I didn’t know it at the time, but I needed a lot of help. I was taking so many pharmaceuticals: anti-anxiety, SSRI’s, and beta blockers, and antidepressants. I was on an incredible cocktail of drugs just to try and get to work and get through the day. I stopped everything. I said, “I can’t fucking do this anymore.”

In that period, I came up with the concept for a business. I patented it and then joined Target as their first Entrepreneur-in- Residence. When I joined Target as their Entrepreneur-in-Residence, they then owned my idea. As owning my idea, I felt they may own it, but I’m still the custodian of it. I looked at their strategy, rebuilt their corporate strategy, and as a result of rebuilding their corporate strategy, I was made Vice-President of Innovation. There, I built their internal innovation program and built a Techstars accelerator. Ultimately, they decided to close my company but keep everything else I built open. I had built a beautiful team of 38 people who I love to death, who had chosen to give their careers to this mission. They had succeeded, and Target closed it because of internal stuff that I can’t talk about- NDAs- but they closed it for things completely unrelated to my company. I went crazy. I just lost it.

Michael Kurland (21:26):

I think this is a good point to stop. You learned from the best of the best. You were at the top of your career for 15 years. You burnt yourself out and then you made a ton of money. You were “successful” and then you started your own company. All the meanwhile, you were on this pharmaceutical cocktail of drugs just to get yourself through the day because you felt empty inside. Is that what I’m hearing you say?

West Stringfellow (21:56):

Yeah. I would say I felt an inability to understand why I should wake up. When they closed my company, the reason to wake up was gone. Even though I had a job at Target, it wasn’t the thing that I had built. Even though I built a team, there’s a difference between when you build an idea and you patent it. You take it to market. It’s totally different from having someone else’s money and building a team for them. I became suicidal when they closed my company. I was going to kill myself, and I had a really solid plan.  I was going to execute on that plan. Right before, literally the day, I had it all planned out so it wouldn’t be messy. Everyone would be okay.

Michael Kurland (22:43):

This is the tipping point.

West Stringfellow (22:49):

I decided, “I don’t know why I’m alive. I failed my team. I failed myself. I failed everything that I possibly thought was valuable in this world.” Even though I had a shitload of money, it just didn’t mean a fucking thing. I was going to blow my head off. I literally set up everything in my room so that I could do that. I was aligning the shotgun with my medulla oblongata so I could blow the back of my head off my neck and sever my head from my spinal cord and feel no pain. I noticed that I was wearing a $36,000 gold Rolex. I thought to myself, “What kind of a fucking prick am I?” I actually had this weird little thought, “If you sold that watch, I bet it would be worth something. [Laughing] You could spend that money on doing things that help people. You build solutions. You can do that for the world’s biggest companies. Why do you not do that for the world’s biggest problems? What the fuck is wrong with you?” It was this really clear voice in my head, when I didn’t have a lot of clear voices. That voice gave me this tiny filament of happiness. Not happiness, but the potential to think that maybe if I did something different, I could be happy. At that point I said, “I haven’t tried everything in this life. I actually could just try using every dollar I have to teach the world how to solve its own problems, just like I solve problems for businesses. Why doesn’t everyone know how to do that and why can’t I do that?” I was Chief Product Officer at Rosetta Stone. I learned from incredible people, incredible geniuses that teach people digitally. I said, “What the fuck? Why don’t I just teach people digitally how to innovate?” I put the shotgun down. I called my girlfriend at the time and said, “Hey, I just tried to kill myself. I think I need real help.” I went into therapy in a big way. When I went from being an Entrepreneur-in-Residence, which was kind of an arm’s length relationship with Target, to being Vice-President of Innovation, one of Target’s executive perks is you can go to the Mayo Clinic and be assessed for executive physical kind of stuff. I went to the Mayo Clinic. I went through three days there. On the third day, the head of clinical psychology wanted to meet with me. They said, “You tested in a unique way, and he wants to talk to you. I said, “Well, I always tested well, so I probably crushed this fucking test.” I went in there, and he said, “Here’s the thing. We think you’re bipolar. Normally, when we meet people like you, they’re homeless, in jail, or dead. You are kind of weird in that you are not one of those things.” That was not very helpful to my narrative, so I ignored that. When I had to deal with myself for the first time, I said, “Okay. I need help.” I learned that a lot of people who have extreme PTSD become bipolar and that a lot of the bipolar stuff that I was expressing was actually an expression of severe trauma that I hadn’t dealt with and that I hadn’t confronted. A lot of things in my life started to make a lot of sense. Why hadn’t I taken care of the people in my life more? Why hadn’t I taken care of myself more? Why was I constantly looking for more outside of myself instead of really spending time with an emotion on the things that had, which were just as precious as my own life, if not more. Ever since I had that break point, which was a real fucking break point… For me to admit that I needed help was like the most insane thing.

Michael Kurland (27:05):

The hardest thing?

West Stringfellow (27:07):

I used to look in the mirror and say, “Man, what the fuck are you doing? Don’t be a pussy. Keep moving.” That kind of language was the shit that was yelled at me as a kid. I learned no; that’s extremely unproductive, and it’s really unhealthy and that I need to actually take time and blah, blah, blah. Four years later, at that moment, I decided, “Okay. I’m going to dedicate everything.”

Michael Kurland (27:41):

Let me pause you here. You were at the pinnacle of your career. You left there. You started a company that was bought by Target. They shut it down. You lost your reason to live and then you found your reason to live at the very moment. I just want to say, thank you for finding that reason because I’m happy you’re here, and I think the rest of the world is, too. I think you’ve still got a lot of work to do.

West Stringfellow (28:08):

I appreciate that.

Michael Kurland (28:09):

I can relate to a lot of things that you’re saying. I had trauma as a child, too, with my father being an alcoholic. I was definitely yelled at “Don’t be a pussy” numerous times as a child. I think you probably built these walls up because I know I did. You probably were starting, for the first time, to bring these walls down and these barriers down and let other people in. I think what I heard you say was you thought you were weak if went to or you thought therapy was an option for you.

West Stringfellow (28:44):

That was not an option. It wasn’t even weak. It was disgrace. It was an embarrassment. It was a failure. Weakness is something on the way to failure. Therapy was failure.

Michael Kurland (28:59):

I was the same way. I had got 34 years into my life, and I mentally bootstrapped it through my life. I don’t need anything. I’ve just got a strong will because I have always landed on my feet, and I’ve been good. Kind of similar to what you were saying, just get through it and build up the walls. Then I hit 34, and I just started like melting down crying for so many different reasons. I called my best friend one day, and I said, “I think my wife is having an affair. I think I need to go to therapy. He said, “You definitely need to go to therapy.” I said, “Does that make me weak?” He said, “No. It makes you weak if you don’t go,” and that’s when light switch went on.

West Stringfellow (29:45):

Thank you for sharing that. I really appreciate that you shared that because it’s hard. One of the things that I love about talking to my niece and nephew and the kids in my family are that I think they have an incredible emotional connection with themselves and with their friends. They are way more aware of the fluidity of identity and life and how complicated and emotional things are. I think of our generation and generations before us, it was stuff it aside and focus on this narrative that you’re supposed to achieve in this life, which is not where I ultimately think we should be as a species. I very much appreciate you sharing that because it’s important, I think, for us to empathize with one another and recognize that there’s a lot of people out there who need the same help and are driving themselves off a cliff. Many of my friends have killed themselves. Many of my friends have died from overdoses, have died from just weird circumstances where they wouldn’t have been in had they not kind of been pushing themselves. Many in my family in the last couple of years have died from similar circumstances or very sick and on the way to dying. It’s tragic to not see that. Before it would happen, I would say, “Well, that fucking sucks.” Now, I say, “Oh, my God. I understand why they’re there.” I am so sad, and I wish that I could help them not be there. I think part of that help comes from finding community and finding your tribe and feeling empathy with someone else and recognizing that we all have some pretty significant stuff that we carry with us. Everyone’s story is different. Everyone’s pain and trauma are different but, without that acknowledgement, none of us make progress.

Michael Kurland (31:40):

You brought up two good points. One of them is the tribe. I’ve mentioned Sebastian Youngers book Tribe many times.

West Stringfellow (31:50):

Great book. Unbelievable.

Michael Kurland (31:52):

It’s a must read for anyone that’s a human. If you’re a human, read the book.  I think is something that everyone needs to hear is if you need help, whatever it is, and there’s nothing too big or small. It’s whatever your trauma is, it’s your trauma. It’s your life. Seek that help. Most of us exercise to physically be in shape. You’ve got to exercise your mind, too. You have to deal with some of that stuff in there. If you have a knot, you’re going to go to physical therapy. If you hurt your back, you’re going to do physical therapy. You’re not a wuss if you go to physical therapy, so why would you be a wuss if you go to mental therapy? I think that’s important.

West Stringfellow (32:37):

I agree with that very much. I think it’s a wonderful analogy in that we take care of our bodies. We take care of our wallets. We take care of the things that are external to us, but our mind is our central processing unit. If that has some logic in it that is irrational or unproductive or self-destructive, that logic will win. The goal is to overcome that logic.

Michael Kurland (33:04):

You will create your own narrative that makes you feel comfortable, even if it’s irrational, but you don’t think it’s irrational because you live in that head space. There’s no one talking you out of it. There’s no one telling you, “That irrational.” You say, “No. This is totally me. This makes sense.” No, it doesn’t. Most of us – probably all of us- have something like that. This is all good information, West.

I want to move now to where you’re at after. Now we’re at HowDo. This is where you’ve taken your life’s work, and you are being better by putting it all into HowDo. Talk to me about HowDo and what you’re doing there and what you’re doing for people out there. Let’s hear about that.

West Stringfellow (33:48):

When I had my break point, I said, “How do I get out of this?” Literally, “How the fuck I get out of this? How did you get anything done before?” There’s this massive element of fear of confronting the things that I had never confronted and didn’t want to. I also recognized that the way that I got through everything before was by doing it, literally just doing it. Not to steal Nike’s thing, but doing it teaches you how it needs to be done because you will fail along the way. Failure, in my opinion, is the decision to stop iterating. That’s it. I knew that if I kept iterating, I would find a way to relate what I know to the world. I started with a very simple concept. I wrote down everything I knew, literally. I posted on Medium. I read about a hundred books. Summarized about 70. I posted that on Medium. In 30 days, we had 36,000 people read for 90 days. Ninety days of continuous reading in 30 days, which was incredible. I thought, “Okay. Maybe the stuff that I know is not completely worthless and so I should figure out a way to structure this so it’s more consumable for the mass market.” Over the last 4 years, I’ve just been iterating to find more and more consumable ways of teaching people how to build a plan. I think so many startups that I talk to, literally daily, don’t have a plan and they go to market without understanding the customer, consumer, the marketplace, how capital’s gotten and why capital is this distributed, and then how to build actual product. So many people follow lean startup, which is just like throwing your money at a solution and if it sucks, iterate. The reality is most people don’t have the money for iteration, and they don’t factor that in. They throw their money at a solution and then they run out of money or they try to raise money, and they don’t have enough of a solution. That is why north of 90% of startups fail within three years. It’s build a plan, build a product, and then you got to build team. You can’t do anything in his life without a team, without a tribe. Then you have to understand the tools. Unfortunately, it is really simple. There is only build-buy-partner. Under build, there is product and platform. Under buy, there is M&A and corporate venture capital. Under partner, there is accelerators and incubators. That’s it. Those are your tools. Each one of those tools is available to different categories of company. The ultimate conversation is how do you manage yourself through all of that? Because showing up every day for your team is the most important thing. Showing up every day to execute everything that needs to be done to respect the capital that you have is the second most important thing. If you take care of the capital and not the team, you’ll lose the team. If you take care of the team and not the capital, you’ll get more team. You’ll get more out of it. You’ll actually do better in business. I think that relationship is not correlated very well right now. Most people think capital is the primary. No. Team is the primary. I’ve structured curriculum around that. I have tested the curriculum at Carnegie Mellon at the G100. I have put it online and tested it with, at this point, 300,000 people from 205 countries and territories, which is every one of them on Earth, literally. The next step is to take everything and turn it into video. We’re going to give that away on every social media platform for free so that we meet the customer where they are.

Michael Kurland (37:51):

I want to pause you here for one second. You’re doing this all for free?

West Stringfellow (37:55):


Michael Kurland (37:55):

Anyone that has a startup plan, can come to you. Go to HowDo and they can get this information. Do they have to qualify?

West Stringfellow (38:06):

Nope. It’s totally free. I don’t ask for any of their data. You can access it. This is a really important thing. When I first got out of college, I wanted to be a philanthropist. I didn’t understand that that required billions of dollars. [Both laughing] I clearly didn’t study business. I met this woman named [inaudible], who is fascinating, just as a superlative human. Quick story. She taught kids how to learn by hiring teachers and taking the chalkboards to train stations in India, as opposed to the government run schools that were eight to 10 miles away from train stations that no homeless child could get to. She took the teachers to the children, and it changed, literally, hundreds of thousands of lives. When I started thinking about how can I give what I know? I’m not saying I am right. There’s no piety here. McKinsey reports that 70% of corporate change fail. Harvard reports 95% of products fail. If the world’s best minds are between 70 and 95% failure rate, nothing’s really working right now. I’m trying to give away the thing that I know and then iterate with the audience. I’ve created this Corpus. It’s centralized on HowDo, so if you want to navigate it in a really kind of easy way, you can there. We’re getting ready to launch a new website in a week that is testing, literally, orders of magnitude more navigable. The ultimate destination for the content is people’s hearts and minds. The ultimate utility of the content is people applying it in their own career, in their own life or their own company for their own purposes, and ultimately for the benefit of their own family and their own community. If everyone did that, self-interested act and used best practice, the world would be better. I am putting it on Facebook and LinkedIn and Twitch and Twitter. Pick a social media network, and my content will be on it for free. If you need a navigation path, go to HowDo.com. It’s free.

We will be releasing an analysis in July that looks at two things: empirical data, meaning absolute measure facts, and forecasts based on empirical data built by the world’s best scientists and statisticians, meaning we take reliable data that is actually happening and then we include variables- positive or negative- and give some sort of range on a forecast, which is very standard stuff. If you look at the forecast for water, air, land, poverty, inequality, imprisonment. Pick a variable. We are moving in a direction that is very uncomfortable and ultimately will make generations beyond us suffer. That doesn’t make sense to me, so we need to radically disrupt what’s going on. If we look at the timelines for this kind of disruption, the iPhone took 10 years to get to 50% micro penetration. The most successful product on Earth took 10 years to get to 50% of the smartphone segment of the cell phone market. That’s insane. If we want to actually change Earth, we have about 15 years. We have to put things in place that are more successful than the most successful product on Earth. The things that need to be in place need to address the most systemically foundational problems that we have as a society, economy, as humans as a species. COVID has demonstrated that if there is one thing that bonds us, we are a species. Whatever I identify as is a story I tell myself. The scientific reality of that story is that I am a member of a species on a planet that is hurdling around the sun at hypersonic speeds, and everyone who looks and acts like a human on this planet is my brother, sister, mother, father, son, daughter. We are a family, and we have this tiny little biosphere, which is literally several miles high around the entire planet and that’s it. Either we turn that into a very thin layer of survival, or as Jeff Bezos has publicly said… Jeff Bezos, the world’s richest man, who has more data than anyone and more money than anyone, has said that he is going to allocate Earth to a light industrial while billionaires move to space. I’m sorry. I’m not a billionaire, so fuck that vision.

Michael Kurland (43:11):

Everything you just said totally encompasses being better. The fact that you’re doing this for free and you have this like drive and mission, again, you still have a lot of work to do here.

West Stringfellow (43:27):

Very much so. I would say to anyone listening, if you would all empathize, literally empathize with this work, then your voice is important. I am just an opinion. Just an opinion. Yes, my opinion has been built from experience. That doesn’t matter in the real grand scheme of things. What matters is solutions. If you think you have a solution and you think that I’m wrong, then challenge me. If you want to be right, then I’ll amplify you. I am trying to solve a problem, and the problem is not directly correlated with me. The problem is directly correlated with we, and we can do this. How? By doing it! How do you save the Earth? You save the earth.

Michael Kurland (44:19):

Start doing it. Stop letting politics and money get in the way because all that stuff doesn’t matter if there’s nowhere to spend that money or breathe that air.

West Stringfellow (44:29):

It will never make you happy.

Michael Kurland (44:32):


West Stringfellow (44:32):

It will never make you happy. I had a terminal amount of money, meaning I didn’t need to worry about it, but that didn’t matter. I’d rather sever my head from my neck then relish the opportunity to buy another RA.

Michael Kurland (44:48):

I totally agree with you. We are one species. We are human above all else. COVID proved, like you said, it didn’t discriminate. It just took out humans.

West Stringfellow (45:05):

Correct. Several people that I love. I know that everyone out there has like that similar story where it scared someone or, unfortunately, they lost someone due to this common problem. If we don’t recognize that common humanity, then…

Michael Kurland (45:20):

We got to put all of our small, short-term wants and needs…

West Stringfellow (45:28):

All differences. The narcissism is such that my differences are so different than yours that I’m willing to let you suffer. No.

Michael Kurland (45:35):

The religious, these genocides that are happening. All that stuff. I agree. Until we can all get on the same page and start realizing we’re a species and we got to make this one place that we live habitable for the future. Like you said, we’re not moving to space. Not in our life.

West Stringfellow (45:59):

I don’t have the billion dollars to afford the ticket.

Michael Kurland (46:01):

West, this has been great. This has been a really eye-opening back and forth, mostly listening to your wonderful story.

West Stringfellow (46:12):

I’m sorry.

Michael Kurland (46:13):

No, that’s what I wanted. I wanted you to talk. Your story is very impactful. Thank you for sharing.

West Stringfellow (46:24):

Michael, thank you so much for curating this conversation. This is a very necessary conversation. I really appreciate that you and your mission with your business incorporates this kind of conversation because this is how this conversation will scale. It will not scale with governments. It will not scale without businesses really leaning in and making it happen. Thank you for allowing me to even share my wacky opinion.

Michael Kurland (46:51):

Thank you, West. If the audience wants to get ahold of you, how can they do so?

West Stringfellow (46:56):

Two ways. My name’s West, and my website is we.st. You can contact me directly if you’re interested in contributing to HowDo. I’d honestly love to hear from you. Please email me at west@howdo.

Michael Kurland (47:20):

Great. Thank you, West, again. This has been a very great conversation. Audience, until next time.

I’d like to take a minute to thank you, our valued listeners. My intention is for this podcast to inspire you, in some way, to be better. Change starts from within and radiates outward. Therefore, start with being better to yourself and only then will you recognize how to be better others and your community. Thank you for joining us today! If you want to learn more about Branded Group, then visit us at www.branded-group.com. From our website you can follow us on social media. Also, always feel free to reach out to me on LinkedIn. Until next time, Be Better.

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