Consumer to Creator

SumoCon 2016 with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), Justin Jackson (MegaMaker)

In September 2016, I attended SumoCon, the first conference that SumoMe ever hosted in Austin, Texas. The photo above with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), and Justin Jackson (MegaMaker), represents one of the happiest and most symbolic moments of my life.

This was my first time meeting all of these guys in person, but I had already been using their products for several years. Without their products and companies, I most likely never would have become a “creator”.

Justin Jackson was one of the first “digital entrepreneurs” who I started following online. He had successfully launched a number of digital products including his popular ‘Marketing for Developers’ book and a lot of his writing taught and inspired me to think about how to create and sell digital products.

When I started Product Manager HQ, I used Noah Kagan’s SumoMe product to significantly improve subscriber opt-in conversions on my website. These subscribers became the foundation of my weekly newsletter list (a list that I’ve been sending weekly newsletters to for the past 3 years).

All of these subscribers are managed through my e-mail provider, ConvertKit, a company founded by Nathan Barry. ConvertKit helps me manage my website’s drip sequences, subscriber lists, automations, and newsletter broadcasts to make sure that I’m always engaging with my loyal readers.

Lastly, my entire online course, One Week PM, is hosted and managed by Teachable, founded by Ankur Nagpal. Teachable allows my entire course to be self-serve, where students can enroll and login to view lectures anytime they want.

Without these guys, Product Manager HQ most likely would not have existed or reached the scale that it is today. Their products enabled me to become a “creator” and for that, I am eternally grateful.

We’re trained from a young age to consume. Part of this is a result of our legacy educational system borne from the Industrial Revolution:

Mass education was the ingenious machine constructed by industrialism to produce the kind of adults it needed. The problem was inordinately complex. How to pre-adapt children for a new world – a world of repetitive indoor toil, smoke, noise, machines, crowded living conditions, collective discipline, a world in which time was to be regulated not by the cycle of sun and moon, but by the factory whistle and the clock.

The solution was an educational system that, in its very structure, simulated this new world. This system did not emerge instantly. Even today it retains throw-back elements from pre-industrial society. Yet the whole idea of assembling masses of students (raw material) to be processed by teachers (workers) in a centrally located school (factory) was a stroke of industrial genius. The whole administrative hierarchy of education, as it grew up, followed the model of industrial bureaucracy. The very organization of knowledge into permanent disciplines was grounded on industrial assumptions. Children marched from place to place and sat in assigned stations. Bells rang to announce changes of time.

The inner life of the school thus became an anticipatory mirror, a perfect introduction to industrial society. The most criticized features of education today – the regimentation, lack of individualization, the rigid systems of seating, grouping, grading and marking, the authoritarian role of the teacher – are precisely those that made mass public education so effective an instrument of adaptation for its place and time.

Source: ‘Future Shock’ by Alvin Toffler

Despite this fact, we should all aspire to break this consumption mindset.

99% of the world will be perfectly satisfied spending the rest of their life consuming, but only the bold will dare make that leap towards becoming a creator.

Any chance I get, I’ll always stand with a hand outstretched at that border, ready to catch the hand of any individual who’s willing to make the jump.

The Glorious Walks

Below is one of my favorite passages from Roald Dahl’s “Boy” about his father:

He harboured a curious theory about how to develop a sense of beauty in the minds of his children. Every time my mother became pregnant, he would wait until the last three months of her pregnancy and then he would announce to her that ‘the glorious walks’ must begin. These glorious walks consisted of him taking her to places of great beauty in the countryside and walking with her for about an hour each day so that she could absorb the splendour of the surroundings.

His theory was that if the eye of a pregnant woman was constantly observing the beauty of nature, this beauty would somehow become transmitted to the mind of the unborn baby within her womb and that baby would grow up to be a lover of beautiful things.

Call me an optimist, but I’ve always believed that these ‘glorious walks’ were a perfect parallel to undergoing any kind of experience in this world (good or bad) as they provide the necessary empathy and inspiration for bringing your ideas to life.

Great designers often started their journeys by viewing and recreating as many existing designs as possible. A common thread amongst honest designers states that “All creative work builds on what came before. Nothing is completely original.”

One of the first things I was taught as a young budding product manager was to take apps or products that I admired and deconstruct them: breaking down each business model, user flow, visual design, and piece of the technology stack.

Understanding how these great products were built from the ground up gave me even more context and reference material to draw upon when it came time to build my own products.

In venture capital, I spend most of my days observing the beauty of new companies by speaking with 8-15 startup founders per week.

Increasing my reps of meeting with each of these companies is imperative towards building my mental repertoire towards understanding what makes great teams and companies tick.

This mode of thinking has provided a specific mindset that allows me to never regret or be intimidated by any kind of human experience. And that makes life so much more enjoyable.

What’s the First Thing You Do When You Come Home?

A few days ago, I was enjoying coffee with a new friend I had met over the Internet when she proceeded to ask me what my hobbies were.

This question has always been tough for me to answer. I enjoy casual activities (I occasionally play guitar, sing, work out, play sports, delve into nature, etc…) and I have nothing against “hobbies,” but if I were 100% honest about it, I spend the majority of my time doing things other people might label “work.”

If I’m not focusing on venture (studying new industries, talking to founders, helping my existing portfolio companies), I’m probably looking for ways to improve Product Manager HQ or using my remaining time to learn new skills / educate myself on new topics.

I’ve often contemplated taking Jason Lemkin’s (SaaStr founder) approach of outright answering these types of questions with “I have no known hobbies.” #noshame.

One question I like to ask people instead is, “What’s the first thing you do when you get home?”

People tend to follow very standard routines / habits and the first thing they do when they get home (assuming they are working some sort of day job) oftentimes dictate how the rest of their night will go – whether that’s sitting at their desk and typing Netflix into a browser, opening a book, heading to the gym, etc…

I don’t believe that people can change their behaviors easily (there’s a reason most health / fitness apps don’t end up dramatically influencing any kind of diet or exercise behaviors) and understanding their routine actions when they come home provide a much better glimpse into what kind of person they are or aspire to be.


Pain + Reflection = Progress

One item that’s long been on my reading bucket list is Ray Dalio’s Principles, a 3-part 100+ page living document that outlines: the importance of principles, Dalio’s most fundamental life principles, and his management principles.

Ray is probably most well known for founding Bridgewater Associates, one of the world’s largest and best-performing hedge funds, known for it’s cult-like culture.

Empathy and kindness aren’t a top priority there, says a former Bridgewater employee. The firm’s culture of absolute candor is designed to strip out emotional considerations and emphasize cold, Vulcan logic in all decision-making—the thin-skinned need not apply.

-Quoted from an NYMag piece

If you’re curious, you can read more about Ray and Bridgewater in this Fortune piece here.

A few weeks ago, I finally started digging into Principles and a few pages in, one particular section stood out almost immediately. I’ll paste it in its entirety here:

It is a fundamental law of nature that to evolve one has to push one’s limits, which is painful, in order to gain strength—whether it’s in the form of lifting weights, facing problems head-on, or in any other way. Nature gave us pain as a messaging device to tell us that we are approaching, or that we have exceeded, our limits in some way. At the same time, nature made the process of getting stronger require us to push our limits. Gaining strength is the adaptation process of the body and the mind to encountering one’s limits, which is painful. In other words, both pain and strength typically result from encountering one’s barriers. When we encounter pain, we are at an important juncture in our decision-making process.

Most people react to pain badly. They have “fight or flight” reactions to it: they either strike out at whatever brought them the pain or they try run away from it. As a result, they don’t learn to find ways around their barriers, so they encounter them over and over again and make little or no progress toward what they want.

Those who react well to pain that stands in the way of getting to their goals—those who understand what is causing it and how to deal with it so that it can be disposed of as a barrier—gain strength and satisfaction. This is because most learning comes from making mistakes, reflecting on the causes of the mistakes, and learning what to do differently in the future. Believe it or not, you are lucky to feel the pain if you approach it correctly, because it will signal that you need to find solutions and to progress. Since the only way you are going to find solutions to painful problems is by thinking deeply about them – i.e., reflecting – if you can develop a knee-jerk reaction to pain that is to reflect rather than to fight or flee, it will lead to your rapid learning/evolving.

So, please remember that:

Pain + Reflection = Progress

When I first glanced over that 3 word formula, my mind immediately raced through all of the recent painful junctures in my life. While I hope to never revisit any of those specific situations again, I can’t help but agree that those times of pain spurred some of the most pivotal changes that positively influenced my well-being.

Ironically enough, now that life has re-stabilized towards a healthier baseline, I sometimes find myself worrying that I’m not creating enough pain in my life to push through existing boundaries.

As my friend Ray and I often jokingly say to each other, “You can’t get out of bed if you’re sleeping in silk sheets.”

Tim Ferriss, one of the world’s leading self-development gurus, has previously recommended that everyone should intentionally re-create painful situations every once in awhile, whether that be intermittent fasting, or sleeping on the sidewalk outside your home for the night.

The thought process of creating these mini-scenarios is is 2-fold:

1) You’re forced to leave your comfort zones which drive you to be more resourceful and think creatively.

2) You break the cycle of hedonic adaption (the observed tendency of humans to quickly return to a relatively stable level of happiness despite major positive or negative events or life changes) and become more appreciative of your present situation. Additionally, you are less likely to feel as negatively impacted when something “bad” happens in your life.

It sounds masochistic but one thing I’d like to explore more of this year is how I can methodically create more pain in my life.

Smells like a potential side project idea…

Comfort Is Mere Steps Away

A few weeks ago, I left San Francisco for a relaxing 2 week vacation in the “mother-land,” Taiwan (I was born in California but my parents immigrated to the U.S. from Taiwan).

One of my best childhood friends moved out to Taiwan 6 months ago to live with his older brother and pursue a career in music production so a couple old friends and I went out to visit him over Christmas / New Years.

The entrepreneurs I happened to meet out there were hustling in completely different domains other than tech and most of the population seemed to be working in the hospitality / service industry.

Meanwhile, I had no international plan on my phone so I didn’t have service (apart from the occasional Wi-fi access) nor a fully planned calendar like I normally do in SF.

Needless to say, it was a different pace of life – call it a digital de-tox if you will.

After coming home to SF in the second week of the new year, I found myself jet-lagged, sitting up at my computer at 3:00am, aimlessly scrolling through my Facebook Newsfeed. Worst idea ever.

Everyone had just posted their new years resolutions / life-planning so I couldn’t help but feel an overwhelming sense of fomo (fear of missing out) and anxiety. Everyone else seemed to have planned their life out for 2017 and I was 2 weeks behind.

It was a terrible feeling and I couldn’t shake off this feeling of aimlessness. My gut reaction was to run away and return to the comforts and relaxed pace of Taiwan.

After that night, I went into full panic mode and did my own personal planning, which led to the output seen in my very first post about a Personal Roadmap. I thought that the planning would help me maintain control over my life again but after a few hours of finishing that planning, I still felt aimless.

A week later, I met up with a friend and mentor of mine for one of our monthly coffees. I dumped my thoughts and told him everything I was thinking: from missing the freedom and comfort that I had felt in Taiwan to being unsure about 2017.

And as sad as it sounds, I was honest with him because I was secretly hoping that he’d be able to give me some sort of answer that would re-kindle a sense of purpose in me again.

After listening to me rant for awhile and taking time to look over my personal roadmap spreadsheet, he took some time to gather his thoughts.

“First of all,” he said, “Comfort is always just mere steps away.”

It was a very simple sentence, but the words rang true.

Deep down, I know that comfort is always available. At any point, I can always pick up and go settle somewhere where I don’t have as many responsibilities – somewhere where I can hang out, relax, and live an easy life.

“Secondly,” he continued, “from what I know of you and seeing this spreadsheet you’ve created to codify what it means to be a great VC (see the Personal Roadmap post), I see a recurring pattern in who you are.”

“Whenever you learn something new, no matter what it is, you’re able to quickly grasp and codify all of the moving pieces, prioritize the important pieces to learn, and break it down into simple concepts for others to easily understand. You have an ability to bring others into these realms of things that you’re learning. More than that, you have an innate desire to share your knowledge with the world.”

After he said that, I sat there in silence and tried to process his “objective view” of who I was. I had never really heard this from anyone else but it resonated so deeply with me that I couldn’t help but wonder why I hadn’t come to this same conclusion myself.

In high school, I couldn’t afford guitar lessons so I practiced 4 hours a day by watching YouTube videos (pausing videos to see which strings and frets a guitarist was pressing). After learning enough to become decent, I never wanted anyone else to go through the same struggles of learning, so I started a guitar club and spent every week teaching beginners how to play.

In college, I grew tired of figuring out how to pay for rent so I taught myself how to trade on the public markets and ended up teaching an accredited class on Stocks & Investments to Berkeley students for the last 2 years of my undergraduate degree. Many former students have e-mailed me over the past few years telling me about their successful portfolios and the steps towards financial freedom they’ve attained from better investments – a few took their learnings a step further and now work at hedge funds.

The most hilarious fact in all of this is that I’ve even kept these two hand-written quotes on the wall in front of me for many months and in all of my anxiety about aimlessness, I never once bothered to look up and read what I had written down months prior.

A week after all of this, a friend of mine who I had met with many months ago coincidentally posted this on Facebook, which left a huge smile on my face:

Comfort will always be mere steps away, but I’m not ready for it yet.

There’s too much left to learn and too many people in this world that I want to share these learnings with.

I’ve always believed that talent is universal but opportunity is not, and one way to create these opportunities is by teaching everything I know.

So here’s to a great 2017.

Talking Growth, Story-Telling, and Entrepreneurship with GrowthX Academy

Late last year, I was invited by GrowthX Academy in San Francisco to give a talk. I covered a full range of topics including:

  • How I first broke into tech
  • Growth tactics with Quora & story-telling
  • How to properly build relationships with your mentors
  • Scaling Product Manager HQ
  • Venture Capital

Wanted to share the recorded video of the talk below as well as the raw transcript (for those who don’t like watching video). Enjoy!



Video Transcript (click ‘Continue reading’)
Continue reading “Talking Growth, Story-Telling, and Entrepreneurship with GrowthX Academy”

Trust That the Dots Will Connect

A personal friend who recently read my post on ‘Exercising Your Hustle Muscle‘ asked how to know when you are exercising the right muscles. So I thought I’d expand a bit more today on that previous post.

“Reed College at that time offered perhaps the best calligraphy instruction in the country,” Jobs said when he gave Stanford’s 2005 graduation speech. “Throughout the campus every poster, every label on every drawer, was beautifully hand calligraphed…I learned about serif and sans serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great. It was beautiful, historical, artistically subtle in a way that science can’t capture.”

“About two years later Steve came back to Reed to tell me he was working on computers out of his parents’ garage,” says Palladino, now a retired priest doing masses in English and Latin in Oregon. “He wanted to consult with me about my Greek letters.” As Jobs told Stanford’s graduates, “When we were designing the first Macintosh computer, it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful typography. If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts. And since Windows just copied the Mac, it’s likely that no personal computer would have them.”

Many years ago, I was entering college and decided to join one of my school’s largest business associations. The organization was split amongst multiple committees and new members needed to undergo an application / interview process in order to be placed in a committee.

As a naive student aiming to major in Business Administration (ended up being a mostly useless degree), I aimed straight to join the coolest sounding committee: the Professional committee – a committee responsible for organizing events like resume review workshops and professional networking dinners with large corporations.

When committee decisions were announced, I was initially disappointed to learn that I had been placed in the Community committee, which focused on maximizing member happiness and you guessed it – building community. It ended up becoming one of my favorite semesters in college. My social, extroverted personality meshed extremely well with the team, role, and mission of that committee.

In the following semester, I applied for a cabinet role, which involved leading one of these committees. When decisions were released, I rushed to check the decision list and saw my name neatly printed next to a committee called Media Technology.

Media Technology? Wtf?! I was livid. Media Technology was a team that filmed and edited videos for the organization and it had nothing to do with any of my professional interests. I had 0 prior experience in filming or video editing and I irrationally believed that I was being put in a position to fail. After a week of grumbling, I set my ego aside, followed through with the semester, learned how to use a camera, fiddled around with video editing software, and did what was necessary to execute on my responsibilities. 

After I left that organization, I shelved those experiences and never gave them a passing thought.

8+ years have passed since then.

Over the past 2 years as I initially struggled to grow the Product Manager HQ community, I found myself mentally referencing many of the strategies and tactics I had picked up during my Community committee semester. The community has since grown into the largest Product Slack community in the world.

Last year, I remember staring at the hundreds of e-mails in my inbox from subscribers who were requesting a way to learn product management skills. I purchased a nice webcam, microphone, and video editing software from the nearest Fry’s Electronics (how the hell are they still around?!). Within 2 weeks, I had filmed, edited, and launched my own online course to teach the fundamentals of product management: One Week PM. I didn’t have to reference a single tutorial or ask anyone for help – I already knew how to film and edit videos from my time in Media Technology. The course has since been taken by hundreds of students from all over the world and many students have gone on to land product manager roles.

“You can’t connect the dots looking forward,” Jobs told the Stanford grads. “You can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”