Venture Capital and Product Management

Ever since entering the venture capital industry 8 months ago, I’ve been thinking about how best to cross-pollinate venture work with my previous product experience (Even going as far as to guest-speak on the #1 most listened product podcast about how Venture Capital is Product Management).

In my first post, I discussed how I first attempted to codify the qualities of a good VC. This step was important so that I could begin mapping PM skills / workflows to VC skills / workflows and look for overlapping opportunities.

At a sky-high level (reiterating: sky-high level), you can imagine product management to break down into 3 core buckets of:

Product Planning

All the user research / needs gathering / synthesis of qualitative & quantitative data that helps inform what product / features should be built.


All of the roadmap planning / sprint planning / spec writing / launch planning / cross-functional collaboration that gets the product launched.

Post-launch Iteration

The ongoing planning & execution necessary to keep successfully improving and growing the product post-launch.

If I map this to venture capital, I imagine it to look something like:

Product Planning = Sourcing

Creating deal flow through outbound sourcing (researching industries and doing cold outreach, attending events / demo days, hosting office hours at accelerators, etc…) or inbound sourcing (referrals, inbound e-mails, people pitching you at a party, etc…).

Execution = Diligence / Executing the investment

Filtering through sourced companies by undergoing deeper diligence (getting to know the founding team, deconstructing the product, digging into metrics, looking through historical financials if there are any, competitive analysis, determining customer love, etc…), negotiating terms, proving value-add to win competitive rounds, executing the investment.

Post-launch Iteration = Supporting your founders

Working with the founders to support them and help them succeed in any way possible (board meetings, strategic advice, helping them hire, finding them customers, guiding them on product strategy, thinking through growth strategies, etc…)

Tactically, here are a few random examples (these examples aren’t too structured so bear with me) of cross-pollination that I’ve thought about or tried so far:

Roadmap: I started by creating a personal roadmap outlining the VC skill-sets I wanted to improve throughout the year. I’ll need to regularly re-visit this roadmap in order to re-prioritize where I want to be focusing my time.

Venture Backlog: I’ve created a backlog of venture projects (for myself and a few members of the venture team) that I cost and prioritize so that I can actively work on top-priority projects during any rare down-time I have.

Sprints: I need to do a bit more thinking about this one. It’s easy to fantasize breaking down my workflow into sprints / sprint tasks but my weeks can be spontaneously unpredictable, especially if we’re considering an investment where the funding round is moving quickly. This leads me to believe that the traditional product sprint cycle would break far too often to be accurate or even necessary.

Specs: It’s not an exact parallel but I’ve tried to structure writing my investment memos as if I were writing product specs. There’s not as much team collaboration around memos (we’re generally expected to have filled out the majority of our memos with our own points of view) but we’re expected to be just as thorough and think through all “edge cases.”

UX: I’m always looking to improve the “user experience” for founders. I never want a founder to leave a meeting feeling like they’ve wasted time with me. I’ve been experimenting with various methods of feedback – one passive strategy was creating a Typeform that I link in my e-mail signature. Lot of clicks but no responses yet (I may shift to simply linking to this Typeform in my rejection e-mails to founders)

My e-mail signature

TBD: I’m going to keep this a living post and update accordingly as I experiment with more cross-pollination in the upcoming months

If you want some more inspiration around the importance of cross-pollinating, check out Scott Adams’ book “How to Fail at Almost Everything and Still Win Big.” For those who don’t know, Scott is the original creator of the Dilbert comics and this book is a peek into his life journey from his humble origins into the comic superstar that he is today.

It’s a great feel-good story: a seemingly average underdog overcomes potentially career-ending voice & hand health issues, works consistently on nights/weekends at his craft, and finally gets the break he needs.

More importantly, there are a few pieces of “career advice” that he sprinkles throughout the book. One particular non-traditional recommendation he gives is to forget about becoming the best at one specific thing and instead become very good (top 25%) at two or more things.

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.


How the Economic Machine Works

After finishing my previous post referencing Ray Dalio’s Principles, I ended up digging around the web and came across this 30-minute gem where Ray Dalio uses extremely simple principles to explain how the economic machine works.

The video is nicely narrated & visualized – definitely worth the 30-minute watch.

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…

Treat Yourself

For most of my life, I’ve tried to live a somewhat frugal and minimalist lifestyle, spending only on essential items.

Every now and then, I’ll re-evaluate what “essential” means to me and I’ll make a purchase outside of my normal spending habits, usually as a productivity experiment to see if the purchase will push my lifestyle to new heights. #treatyoself

Some of these purchases are used a few times and quickly discarded, while other purchases add such tremendous value to my life that I wonder why I hadn’t forked over the cash and bought that item much earlier.

As I grow older, I find that the category of value-add purchases tend to skew towards one of these 4 buckets: preserving health, making me smarter, saving time, or helping me get work done.

Even if these purchases are a bit pricier, the benefits they bring to my life over a long period of time tend to far outweigh the upfront costs.

Purchases that preserve my health:

  • Iron Gym Total Upper Body Workout Bar: This pull-up bar has an easy one-time assembly and having it available to insert over my door motivates me to get a couple pull-up reps in whenever I walk through my door. I’ve also started a mental tally of max pull-ups that I can accomplish and it’s a nice mini-goal to beat every day.
  • Yoga Mat: Every one has different yoga mat preferences but the important thing is just to get one. I use my mat all the time, whether for meditating or stretching.
  • TriggerPoint GRID Foam Roller: I used to be sore after every workout and I constantly had to get massages in order to get knots out of my back. Spending a few minutes with this foam roller alleviates most of my back pain.
  • Duro-Med Relax-A-Bac Lower Back Support Pillow: Speaking of back pain, this is a one-time purchase that your lower back will thank you for your entire life, given how much we tend to sit at our desks (both at home and at work) with bad posture these days.
  • Coccyx Orthopedic Memory Foam Seat Cushion: This is the complementary purchase to above – this cushion helps prevent your butt from getting sore after extended periods of sitting. Grab both the above and this one if you can.
  • Casper Sleep Mattress: You spend half your life sleeping so you better make damn well sure that you’re getting great sleep. Casper is a company dedicated solely towards developing the best in class mattress. I’ve never slept better.
  • Superfeet Black Premium Insoles: If you walk or stand for a large portion of your day, grab these insoles to slip inside your shoes and your feet will feel tons better.
  • Zicam Cold Remedy Rapid Melts: This cold remedy is a godsend. One of my biggest life regrets is not discovering Zicam earlier – oh how many sick days I could have prevented. Whenever I’ve felt early signs of a cold or I already had a cold, taking Zicam was 100% guaranteed to kill that cold within the same or next day.
  • The Life-Changing Magic of Tidying Up: This book has helped preserve so much of my mental health over this past year. The book teaches you how to declutter, re-organize, and simplify your life. I guarantee you will feel both physically and mentally refreshed after you follow this book’s advice.
  • Jumpsport Fitness Mini Trampoline: I picked up this bad boy after learning about Tony Robbins’ routines. He jumps on his mini trampoline before he gets on stage in order to boost his energy. Every time I’m feeling down or antsy, I do a few rebounds on my trampoline and it gives me the exact endorphin boost I need.

Purchases that make me smarter:

  • Endless amounts of Kindle books: If I want to buy a Kindle book, I buy it with Amazon’s 1-click ordering and have it sent to my iPad, no questions asked. I love reading and I’ll never think that books are a waste of money (unless you hoard books and never finish them).
  • Apple iPad Mini 4: I talked about this in my last post but one of the best things I did in 2017 was get an iPad mini to carry around with me wherever I went so that any idle time such as commutes could be spent reading on the Kindle app vs. wasting time browsing social media on my phone.
  • Moleskine Classic Notebook: I used to be so cheap when it came to buying notebooks (old me: “why buy notebooks when I can use the back side of old printed papers!”) but now I carry a notebook and pen to every meeting so I can write down notes to reference later.

Purchases that save time:

  • Amazon Echo: Another one of my best purchases that I’ll never regret spending $200 for. This thing has paid off over and over again – buy 20 less cocktails in a month and use that money to buy this instead. Think of ALL the times you need to manually turn on / off your lights over your lifetime. Think of the times when you’re reading in bed and you’re falling asleep but you have to get up to turn off your bed light which causes you to feel awake again. Think of the times when you want to listen to the radio / music and you have to get up to play something from your laptop / phone. ALL of these tiny moments (yes I realize these all feel like #firstworldproblems) add up and take tons of mindshare. If you can automate all of these with simple phrases like “Alexa, lights off,” or “Alexa, play jazz” you’ll save hundreds of hours over your lifetime.
  • Extra iPhone chargers: Tired of constantly switching chargers between rooms whenever you need to charge your iPhone? Just fork over a bit of cash and buy a few extra iPhone chargers to leave around key rooms in your home. Similar to the Echo, this is one of those purchases that will save you a ton of time over a lifetime.

Purchases that help me get work done:

  • Lapgear Jumbo Lap Desk: How often have you brought your laptop to work in bed only to overheat your computer and burn your thighs after a prolonged period of time? I use this lap desk every time I want to finish up some work in bed or watch a movie.

There’s Never Enough Time

“Wow that’s really cool. I wish I could do _____ too but I just don’t have enough time.”

“How do you have time to work during the day and yet be so involved with _____? I’m so busy, I don’t know how you find the time”

“Oh yeah I definitely plan on doing more of _____ this year. I just need to clear up my schedule and make some time.”

I’ve made so many of these excuses over the past few years. Starting a new hobby? Not enough time. Working on a side project? Not enough time. Learning a new skill? Not enough time. Reading more books? Not enough time.

Speaking from first-hand experience and guilt, it’s so much easier to tell people you don’t have time vs. re-prioritizing your time and getting started towards building a habit.

In order to read more books this year, I’ve taken some great advice from a friend who mentioned that he carries around a Kindle everywhere he goes, so that any idle time (including commutes) can be spent reading books on his Kindle vs. browsing his smartphone.

Shoutout to Nikunj Kothari

Per his advice, I’ve been carrying around an iPad mini with the Kindle app installed (didn’t want to spend money buying a separate Kindle device) and I’ve started to re-prioritize all idle commute time towards reading.

In one week, I’ve managed to get through half of a book that normally might have taken me a month. The trade-off? Less time browsing e-mail, Facebook, Twitter, Instagram on my phone – things that don’t matter anyways in the long run.

If blocking off time during the day is too difficult for you, take some baby steps  like I did by thinking through time in your day that you’d normally spend on time-wasting / shallow activities and fill those moments with whatever you want to work on instead.


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”

Writing an Amazon Best Selling Book With a Stranger On the Internet

One fun fact about me is that in late 2015, I met a stranger from Toronto, Canada online who became one of my close friends, and co-wrote / published a book with him called Quora Domination that ended up becoming a brief Amazon bestseller (reached Top 10 in Advertising & Business Skills categories) and #1 in Product Hunt books – all of this happening without ever meeting him in person.

A lot of people are always curious about how this all happened so I thought I’d elaborate on the context behind that experience as well as how we wrote the book.

I’ve decided to leave out most of the details around the publishing + marketing behind the book as that deserves a separate post of its own and this one will be long enough as is.

Why Write a Book About Quora?

In the first year of starting Product Manager HQ, I was eager to look for channels to drive traffic to the website. While browsing the web one day, I discovered Quora, a Q&A website where you could ask any question you wanted and people would write high quality answers in response.

Over a few months, I slowly became obsessed with Quora, both consuming endless loads of content as well as chiming in with a few answers here and there in order to build credibility as a product manager.

Additionally, I’d take every opportunity I had to leave value-add answers for individuals seeking advice on how to break into product management and I’d take any opportunity possible to link back to Product Manager HQ in my answers.

Quora ended up becoming my #1 source of traffic and helped build up the early subscriber base as well as seed some of the initial set of community members (Unfortunately, Quora isn’t quite the arbitrage opportunity it used to be due to more competition and better content moderation bots which are stricter about backlinks).

Quora was also a great opportunity to meet strangers over the internet as they previously allowed users to message others (they have since removed the ability to cold-message another user unless they are following you).

Meeting My Co-Author

In late 2015, I kept reading answers by an individual named Imran, who ran a website called Escape Your Desk Job, which taught others how to write their own e-books (he had already written and sold 50+ Kindle books on Amazon).

Being the curious learner that I am, I decided to reach out and see if he’d be open for a chat to learn about how he wrote and launched these e-books.

Learning moment: When sending any cold message / e-mail, try to bring immediate value-add to the recipient. In this case, I went through his website and made sure to point out a pretty major bug which prevented a user from going through his desired subscription flow.

Secondly, I made a point to call out my own project at the time (Product Manager HQ) to show that I was a do-er, not a talker (if you don’t have a specific project to talk about, try to point to some previous experience or work you’ve done in the past – coming to the table with any sort of credibility can’t hurt).

Imran and I ended up scheduling a 1.5 hour long Skype call where we chatted about the projects we were working on, his Kindle book writing process, and how we were both using Quora to drive traffic to our respective websites. Most importantly, we spent a good amount of time talking through some of our personal values and got to know + trust each other.

Every now and then, I’d check in and send him an update to let him know what I was working on. Sending these quick updates on my progress not only helped me stay accountable but also continued to build rapport / trust despite the fact that we had still never met each other in person.

A few days after my update, he sent me the message which kicked this whole thing off:

A few things to note here, Imran had already written 50+ books at this point and he could have chosen anyone he wanted to co-write this book with him.

However, by this point, we had already chatted a few times, knew that each other were hard workers who could get sh*t done (we each respected the other’s projects), and again, most importantly, trusted each other.

Secondly, in our chats, both of us had been avidly using Quora for awhile at that point and we both loved the website, which would make writing a book about Quora much easier to complete.

We were also aware that popular writers were using Quora as an avenue to drive millions of views to their writing and get published in major media outlets such as Fortune, Inc., Forbes, etc… so we were eager to decode these strategies and share them with others.

The Writing Process

The next day, we chatted again and confirmed a few necessary items around work / revenue split. Everything would be 50/50 split, including work effort and potential revenue.

Learning moment: It seems fairly obvious in hindsight, but anytime you decide to kick-off any project / business with a potential co-founder, you MUST have the necessary conversations that no one likes to have around equity, revenue, and work effort.

Imran and I trusted each other but we still had this conversation and solidified everything in writing before kicking off the rest of the process.

We then threw up a shared Google Drive and begin outlining our plan of attack: specifically, hammering out a table of contents for the book and divvying up chapters that we would be responsible for writing.

Apart from high quality content, we started with 2 specific goals:

  • Finishing the book content within 2 weeks
  • Writing 1,000 words each (for a total of 2,000 words between the both of us) every single day

This wasn’t our first rodeo working with other people on projects, so we knew how easy it was to let a project fall through the cracks, especially when one person’s calendar got busy.

Setting these target goals were crucial for time-boxing our work as well as providing an exact daily word target. An added benefit of the word number goal was the accountability it provided as neither of us wanted to disappoint the other if we didn’t hit our word goal for the day. #guilttripftw

After splitting up the chapters in our table of contents, it was pretty straightforward for us to execute individually without wasting any time with meetings (I’m a big fan of Jason Fried’s efforts to spread the message around eliminating unnecessary meetings) and we hammered out 14,000 words into a shared Google Doc by the end of the week.

After finishing our individual chapters, we spent the remaining week:

  • Conducting + transcribing interviews with Top Writers on Quora as bonus book content, which added another 6,000 words
  • Hiring a copywriter off UpWork to review and fine-tune some of the writing
  • Doing a bunch of other work to prep for launch (this piece involves a lot of the actual execution behind getting the book published on Amazon / print + marketing / launching – as mentioned in the beginning of the post, I’ll leave this for another post)

In case you’re wondering how any of this might be relevant to you, below are a few of the more memorable skills I took away from this experience (and motivation for you to do your own project):

  • How to work remotely on a project with someone else without ever having to meet in person
  • How to publish both Kindle + print versions of a book
  • How to hire and manage freelancers on UpWork to help streamline / automate manual work
  • How to create a marketing strategy around a book launch to drive continuous book sales over an extended period of time

Co-authoring Quora Domination was one of my favorite experiences so far (I’m sure there will still be countless more) and a great chance to exercise my hustle muscle with Imran, a stranger on the internet who became one of my close friends.

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.”