Social Media is a Highlight Reel

I’m not much of a professional sports fan, but I found this short post-game interview video this morning and thought it was on point and worth sharing. The interview goes on to focus around the importance of embracing failures but I wanted to focus on the first 20 seconds.

Your social media timelines and newsfeeds are “highlight reels” that don’t make you feel any better nor do they help you focus on the process vs. the goals. No one likes to post about their failures, so all you tend to see are “overnight successes” without any footage of the hard work and mistakes made behind the scenes. I’ve often found myself comparing my Stage 1 to someone else’s Stage 10 and assuming that I’m doing something wrong when I haven’t even put in any hard work.

I don’t regret my decision 6 months+ ago to install a Chrome Extension that blocked my Facebook Timeline on desktop. I’m not perfect, and I occasionally check the timeline on my mobile phone when I’m in a morning commute. As an extrovert, it’s a tough feeling to feel a bit disconnected to what’s going on in your friend’s lives.

The flip side is that it’s a great feeling to catch up with individuals and genuinely chat about life updates vs. secretly already knowing everything about their lives from social media posts.

Drastically cutting down social media usage has also helped me focus for longer periods of time without distraction and achieve deeper states of workflow. Try cutting down on your usage and see how it affects your productivity and your mental health.

Continuous vs. Achievement Driven Success

In the last two weeks of every year, I enjoy sitting down to do a yearly audit and planning for the upcoming year.

In previous years, my audit + planning doc used to look something more like this:

  • Purpose
  • Lifetime Goals
    • Metrics of Success
  • 1 Year Goals
  • 90 Day Goals

As you can see, it was a bit more “goal” and “success” oriented, which is how most people tend to structure their own life planning.

The problem with this format is that periodically throughout the year, I always found myself staring at this long checklist of goals that I hadn’t achieved.

These goals started to feel like those items you put on your task list and leave for months at a time. If that’s ever happened to you, you’ve probably felt de-sensitized to a point where you don’t even want to look at your task list anymore.

Needless to say, I wasn’t feeling great. No amount of “accomplishment” ever felt like enough and I felt lacking.

This year, I altered my doc to include these sections:

  • A summary recap of how I felt about the entire year
  • Bullet points around things that went well and things that didn’t go so well.
  • A retrospective around the 1 year goals I had set for myself for that year and whether or not I accomplished them
  • An upcoming year planning section containing:
    • Purpose (usually a 1-liner vision statement)
    • Habits to Start / Continue
    • Habits to Stop
    • 1 Year Goals

I left in the 1 Year Goals section because it’s tough to quit all goals cold-turkey and I want to ease into this goal-less transition.

I also added a section around feedback (I was inspired by a really good friend of mine Tam) from friends and other people in my community (this deserves another post so I won’t elaborate too much here).

At first, I felt a little guilty.

In previous operating roles at startups, we always set impossible OKRs for ourselves so that we could always be reaching higher and accomplishing more.

Was I not thinking big enough? Was I missing out by removing all these goals?

Last week, I stumbled upon this picture while reading this amazing blog post from Patrick O’Shaughnessy and it helped to put into perspective everything that I had been feeling.


Patrick laid it out so succinctly with three words: “Growth without Goals.”

The legacy education system and social media drives us towards a necessity for achievement driven success but two things happen when we follow that method:

  1. We feel like we’re lacking all the way until we hit those success “milestones”
  2. Once we “achieve those milestones,” we realize that we’ve just lost the thing that gave us a sense of purpose

Continuous success is about growth without goals. Developing habits into a way of life.


Strive for Five


One of my favorite images that I never get tired of looking at is this pyramid of ownership. This image laid the foundation for how I think about taking ownership in my work and I often send it to others looking for career advice.

It’s fairly self-explanatory and 80% of the people I show it to experience their own lightbulb moments.

No matter what level you are in your organization, you should always be aiming for stages 4 or 5.

Depending on the organization, you may need to build trust through consistent and accurate decision-making in stage 4 before you are entrusted to follow through on the execution of your recommended solution.

Founders perpetually live in stage 5 because they have no choice – ruthlessly identify, diagnose, and solve problems or the company dies.


How to Get a Job in Venture Capital

Over the past 1.5 years, I’ve gotten a lot of requests from people looking to break into venture capital. In all of these 30 minute coffee chats or phone calls, I find myself giving the same recommendations and tips over and over again.

To scale my time this year, I’m going to jot down the top three pieces of advice I give to those looking to land their first job in the venture capital industry.


1. Brace yourself for the fact that you will be operating differently.

When you “operate” in venture, you are moving at a very different pace.

Note that you aren’t going to stop operating or building – at it’s core, a venture firm is still a company that needs to continually be building, iterating, and adapting to survive and win.

The key difference is that venture firms raise their capital from limited partners and thus aren’t exposed to the market forces in the same way that a startup is.

If a startup cannot build a product or service that satisfies a need in the market, no one will pay them, and they will run out of cash and die. In a startup, there is a real sense of urgency to move each and every single day.

VCs make money from management fees (usually 1-3% of the total funds raised that is allocated towards a firm’s operating expenses i.e. salaries) and carry (usually 20-30% of profits made from successful investment payouts). Since the cash flow from both of these sources has been budgeted into each fund, VCs naturally don’t have the same sense of urgency.

Obviously, a VC can’t hang out for years doing nothing with their LP capital and collecting management fees or else there would be consequences, including serious reputational risk and the inability to raise another fund.

Additionally, the VCs who rest on their laurels, don’t think of themselves as a startup, and expect the best teams to come to them for an investment, will slowly die out.

However, for all reasons listed above, VCs can afford to be patient and wait to make the right investments.

Bringing this back to the initial point, VCs operate in relative silos for most of the working week. You’re often spending most of your time in 1-on-1 meetings & calls with founders getting to know them and their businesses.

One or two times a week, you may have partner meetings where you collectively get together and discuss the most promising companies that you want to dig further into.

For time-sensitive investments, the team will rally together to do dilligence and “win” an investment. Post-investment, the full team will do everything in their power to support the company but usually there is one point of contact for the company who may or may not join the board.

The reason I bring up this point first is that I want people to know that this job is very different than a traditional operating role.

You won’t be surrounded by a team every day and there won’t be any war rooms where you gather to prepare for product launches.

The feedback loop is very long and you often won’t know how you are doing until years later when your companies are performing very well or very badly / cease to exist.


2. Stop networking with VCs. Get to know founders and provide value to them in any way you can.

This is the BIGGEST mistake I see people making when they are trying to find a job in venture.

It’s natural to think that you should spend all of your time meeting with every single VC in hopes that one of them will magically think about you when a position opens up in their firm.

Just like with any other job in any other industry, people want to know that you can do the job effectively.

Specific to venture, you need to be able to prove that you are well connected and have a network of founders who will come to you when they are looking to raise money.

More importantly, VCs want to know if the founders in your network respect you for the value you bring to the table to the degree that they would let you invest in their company.

When I first interviewed for my last venture firm, FundersClub, the investment team there did a reference check with a founder in my network who I had previously done some work for (on nights and weekends). Because I had worked hard for this founder, he spoke very highly of me which helped to build a positive first impression with the team.

If you are speaking with VCs, it should be because you are already meeting with founders, doing the diligence, and are sending promising founders to these VCs.

If you send a founder to a VC who ends up doing an investment in that founder, I guarantee you will be top of the list when that VC is looking to hire.

If you don’t think you’ve built up this network or rapport with founders, see my next point below.


3. Build a unique and proprietary source of deal flow.

Regardless of what position you are in a venture firm, from Associate to Partner, you will always be sourcing. Sourcing never stops, so accept that now.

When you are recruiting for a venture firm, the firm has to believe that you are going to bring:

  1. Unique perspective that will help with developing investment theses & investment decisions
  2. Value-add capabilities i.e. significant operating or founding experience that builds credibility with founders and supports founders in the company-building process
  3. Unique deal flow to bring in founders and companies that the investment team doesn’t already see

Given that experienced founders and operators don’t really need to recruit for venture firms (they usually get courted by VCs), I’m going to assume that the audience reading this post has less to offer on the table for points #1 and #2 and will need to rely more heavily on #3.

Figure out what networks you have access to that the firm’s current investment team isn’t able to tap into (either out of lack of effort or affinity) and get to intimately know those networks. These could be anything from college campuses, founder support networks, online communities, to a blockchain meetup that you organize.

As a small example, I never built the Product Manager HQ community with the intent of finding founders but it naturally became a great source to tap into when I went through venture recruiting.

During the interview process at my last firm, one of my tasks after my first round interview was to find two seed-stage companies that I’d be interested in investing in personally and get in touch with their founders. I was given two weeks to complete the task.

I went home, pinged my PM community, and asked if anyone worked at a seed stage startup.

Since I had founded, provided value, and built trust with this community for a long time, the PMs trusted me enough to tell me more about their companies, what they were building, and even offered to make introductions to their CEO / co-founders for me.

It took me about an hour to finish the task and send back a detailed e-mail with two startups that I selected along with my investment rationale and proof that I could get in touch with their CEOs at anytime.

The investment team scheduled a follow-up interview round with me that same day.

If you don’t believe any of your current networks to be that unique or proprietary, then put in the work and create one. If you aren’t already acting like you are a VC who is constantly thinking about building unique networks, then you won’t succeed on the job anyways.

Good luck!

Solving the Right Problem

Mathematicians undergo years of education and training and oftentimes spend most of their entire lives dedicated toward solving one mathematical problem of their choosing.

These mathematical problems range widely and solutions to some of them would create mind-blowing implications to multiple fields including math, science, and technology.

An example of some of these important problems are the seven Millenium Prize problems, stated by the Clay Mathematics Institute in 2000.

Anyone who can complete a solution to these problems will be awarded a $1mm USD cash prize, and likely become a strong contender for the esteemed Fields Medal.

Only one of the problems (Poincaré conjecture) has been solved thus far. The Russian mathematician, Grigori Perelman, who solved it ironically turned down both the cash prize and the Fields Medal.

Whenever I read about these mathematicians, I think of two questions:

  1. How much time does a mathematician spend before settling upon the problem they want to dedicate their lives to working on?
  2. Once they decide, do these mathematicians feel a great sense of clarity and peace knowing that they can focus all their efforts onto one thing?

As the year comes to a close, it’s a good opportunity to ponder the relevance of these questions to your own life.

Have you spent your time this year ensuring that you’re focused on the right problem? Does working on this problem give you mental clarity and peace? If not, why not?

Happy holidays everyone.

Family Time

Earlier this year, I went to do a regular catch up with a good friend at his company office in San Francisco. We headed up to the rooftop to give each other our quarterly life updates. After awhile, our conversation slowly shifted towards how old we were growing and what life goals we were hoping to achieve.

He mentioned that he wasn’t that close with his parents and barely saw them in person anymore, but he worked hard every day so that he could eventually buy his mom a home.

As another first generation American who grew up with many cultural + communication differences from my immigrant parents (since I was born and raised in American culture + society), I sympathized with his statement.

We chatted about this some more, and discussed how it would take several years before he’d be able to purchase something like that for his mom.

After some thought, I asked him an intentionally leading question:

“In 5-10 years, when your parents are even older, do you think they’d be happy if you spent your youth working endlessly without seeing them and one day surprised them with a new house?”

He went quiet immediately and looked away from me – I could notice the discomfort in his face and we sat there in silence for a few seconds.

Too often, we assume that money and material goods can substitute for our lack of communication with family and friends.

When your parents are in their final decades of life, the last thing they need is a bigger home or a more luxurious car. Every day they grow older, material possessions mean so much less and their relationships mean so much more.

All they want is more time with you.

Intellectual Capital

With the meteoric rise of cryptocurrencies and a new generation of crypto-millionaires, I keep thinking back to this epic tweetstorm by Sizhao Yang and how relevant it is for the rest of my life.

Financial capital comes and goes but intellectual capital retains forever.

The wrong mindset is to get caught up in the hype and dream about get-rich-quick scenarios. The right mindset is to remember to continue accumulating knowledge along the way.

Accumulating knowledge and the right mental models allow you to make the smartest decisions and invest in the right areas at the right time.

Even if you missed the crypto boat this time around (unlikely as all ships continue rising in this rising tide), investing in your mind and learning from this experience will pay off dividends in the future.


Learning Days

Most of my workweek tends to quickly fill up with sporadic founder meetings, company diligence, and portfolio company support. Rarely can I find the luxury of uninterrupted work blocks to sit for hours on end and properly study anything I want to learn.

In light of this year’s theme around deep work, I’ve been experimenting with the concept of “Learning Days” where I pick any topic I’m interested in and spend a full day (Saturdays or Sundays) deep-diving into that topic.

My first two learning days (Artificial Intelligence/Machine Learning & Blockchain) were relatively unstructured as I’m still figuring out the best approach to these going forward.

So far, I’ve kicked off each learning day in the following manner:

  1. Wake up and head to the gym for a run (a healthy body is a healthy mind)
  2. Shower and make tea
  3. Create a new Google Doc and throw it up on my second external monitor to document the day’s notes / learnings
  4. Look for a Medium article where someone has already aggregated the best links / resources for learning the topic of choice. For example, my buddy Sam DeBrule compiled a massive list of curated AI / ML links which drastically helped to cut down the time I needed to spend digging around the web.(obviously you’ll want to do your own research but these types of aggregated resources provide a launching point for mapping out what you know / don’t know)
  5. Go through each article I find: read and reflect. Each article should provide foundational knowledge for the next but I try to question / probe everything I’m reading. I want to develop a sense of which authors know what they’re talking about vs. those that are regurgitating information / filling my head with incorrect information.
  6. In my first hour, I try to first understand the history behind the topic (i.e. when and why did AI / ML first come into existence, what worked and what failed, what catalysts are leading to breakthroughs now)
  7. Now that I have better context around how we got to this point, I’m better able to understand the current state of AI / ML as well as map out a hierarchy of subtopics (i.e. AI -> Machine Learning -> Deep Learning -> Neural Networks) that I’ll need to prioritize my learning around for the next few hours
  8. For each subtopic, I try to understand: what it is (literally, what is deep learning), how it works (deep learning uses neural networks? ok, how do neural networks work?), and how it’s used in practical business / life (Google Photos uses deep learning for face recognition? much wow). I was never a great academic and this last part helps me tie concepts I’m learning to the “real world” so I don’t forget them.
  9. I’m also careful to include my source links next to all of my Google Doc notes so I can easily reference them at a later time.
  10. At the end of the day, I’ll revisit all of the raw notes I’ve taken and take some time to organize / structure them in a readable format – the hope is that someone completely foreign to the topic could pick up my notes and easily understand what I’ve learned that day
  11. As an additional forcing function, I’ve tried to “Feynman Technique” the whole process by teaching my significant other everything I’ve learned. Teaching the subject matter helps me quickly figure out which concepts or subtopics I need to spend more time on. It also helps that she likes to play the “why why why” question game which really forces me to simplify each complex concept. After teaching the topic, I have a list of follow-up questions for myself that I need to dig into since I couldn’t easily explain them.

I’ve got a long ways to go with these Learning Days but I’m loving them and they’ve spurred a new love of learning that makes me even more excited to wake up every morning.


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.

Define Your Strike Zone

In one of my early middle school English classes, I had a seat next to the teacher’s desk where he had taped a poster of hockey athlete Wayne Gretzky and the quote “You miss 100% of the shots you never take.”

If I managed to submit a quiz early, I would lay my head down sideways on my desk and stare at that poster’s quote while waiting for the recess bell to chime.

At such a young age, my brain was especially malleable and I grew to embody that quote into everything that I did. There was no such thing as a fearful moment or a lost opportunity. Everything was a shot that I needed to take and there were no regrets.

Volunteer to present our projects in front of class? My hand was up first. Everyone scared to take the first leap while cliff-diving in Hawaii? My feet took control and I’d be the first over the cliff into the water.

That quote built an insatiable and intrinsic desire to always be pushing forward. Unfortunately, this desire also meant that I often had too many toes dipped in too many projects.

As a result, a finite amount of time and focus meant that I often lacked the ability to follow-through with each new opportunity.

In hindsight, it’s easy to see how I misinterpreted that Wayne Gretzky quote. Wayne didn’t line up a thousand crappy shots and take them all because he could. He had years of practice and instinct that allowed him to optimally line up his hockey stick, rack up the courage, and take the right shots.

When it comes to investments, Warren Buffett often speaks of a taking a “Ted Williams kind of discipline.”

Ted Williams was a baseball player on the Boston Red Sox who analyzed and carved the baseball strike zone into 77 individual cells. He then created probabilistic results of successful bats for each cell based on his history of hitting in each of these strike zones.

By using his rigid method and waiting for the perfect pitches in his optimal strike zones, Ted Williams maintained a .344 batting average and was responsible for more than a fifth of his team’s runs over two decades. For context, a season batting average higher than .300 is considered to be excellent and an average higher than .400 is a nearly unachievable goal. Ted Williams even managed to hit .406 in 1941 (source).

Now that I’m a bit more self-aware of my flaws, I take more time to focus and think before proceeding to jump headfirst into each new opportunity.

Venture capital has been the perfect industry to maintain this level of discipline. While each new founder I meet is unequivocally infectious, passionate, and convincing (as they rightfully should be), I only have a limited number of shots. Now, more than ever, I need to be defining my strike zone.

The trick in investing is just to sit there and watch pitch after pitch go by and wait for the one right in your sweet spot. And if people are yelling, ‘Swing, you bum!,’ ignore them. Defining what your game is — where you’re going to have an edge — is enormously important.

-Warren Buffett