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Hustle as a Differentiator

hustle

One of my favorite Pat Grady lessons is the one he shares about his wife, Sarah Guo. The short of it is that while Pat was just enjoying his weekend down the wine country, Sarah had used that same car ride over to make several phone calls and several messages over the weekend. A time that most VCs take off for themselves, their family, or their hobbies. But Sarah took to get to know the founders, the team, key executives and everyone who was at the company.

For a deal that Sequoia, a16z, and Benchmark were also fighting over, the firm that won the deal was Greylock. And it was because of Sarah. She had spent so much time with said founders that they couldn’t imagine working with any other partner except for her.

Similarly, rumor has it that Mark Zuckerberg was able to buy Instagram also because of a flurry of conversations over Easter weekend in 2012, when no one else was expecting to be working. And while one can argue the ethics behind how the deal went down (i.e. the intensity of communication, threats or that Zuck was driven by paranoia), the fact stands that Facebook acquired that 13-person company with no revenue at a time when Twitter had offered supposedly $500M to acquire the photo-sharing company, and that Sequoia had also offered to mark the company at half a billion. But when literally anyone else could have won the deal, Facebook did.

I wrote about responsiveness being a telltale sign of excellence earlier this month. So this one is more or less an expansion of that.

I’ve always appreciated the ability in others who are able to make things happen. The hustle. Time doesn’t wait for you to wake up. From my buddy Andrew flying across the nation to close a candidate to Blake Robbins who cold emailed Nadeshot three times per week and bought him tickets to the Cavs NBA Finals game to win the chance to fund 100 Thieves. I hear about these stories every so often, from simple things, like flying to meet a founder and not expecting the founder to fly to the Bay, to more wilder stories to a lawyer cold emailing his way to Elon to get an exec position at SpaceX or sending fan mail to a music artist to put a song into outer space. And I can’t help but feel an immense amount of respect (also often inspired to take action myself).

The truth is most people don’t. Not because they physically can’t send an email on the weekend or jump on a phone call at 10PM. But because they won’t.

As an LP, one of the wavelengths I measure emerging GPs on is their ability to win deals. Too often these GPs brag about their networks and operating experiences. More often than not, not differentiated. I kid you not. Like 99% of the time. But in an age, where every GP has a podcast or a newsletter. Or a community. Hell, every GP knows someone who knows an Elon or a Bill Gates or a Jensen Huang (or they know them themselves).

Admittedly, they all start looking the same. But every so often, I meet a GP or a founder who can’t boast a crazy network or crazy set of prior exits. And the only thing they can boast is their hustle. And they are able to show for it. Those are the folks who I think will change the world.

I will admit, hustle is hard as hell to share in a pitch deck. In many ways, I advise GPs and founders to not include it because there is almost no way that a deck is the best platter to share one’s hustle. Then again, the people who are the greatest hustlers don’t need me to tell them that.

They know. And as the Nike slogan goes, they “just do it.”

Photo by Garrhet Sampson on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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When Trying Something New

new, apple, vision pro

The great Jim Collins has this line I really like where he says fire bullets then cannonballs. “The right big things are the things you’ve empirically validated. So, you fire bullets, you validate, then you go big — bullets, then cannonballs — it’s both.”

Too often — something I see in me as much as I see in founders — when trying something new, we bottle it up. We charge the entropy of our creativity. Waiting to release it all at one big moment. A cannonball. No one else should or needs to know know. Sometimes it’s a fear of someone else stealing your idea. Sometimes, well, speaking more for myself, I just like surprises. I love the mystique. And on the slim chance you’re right, albeit rare, then awesome. But 999 out of 1000 times, you’re likely not. At least not in the first try.

I’m forgetting and also can’t seem to find the attribution. But I read somewhere that the only difference between vision and a hallucination is that others can see it. You see… the greatest YouTubers test their ideas with test audiences several times. In fact, they even test their video titles with select audiences a number of times before launching. (Instagram even added the ability to do it at scale for creators too.) Reporters do too with their headlines. Legendary investor Mike Maples at Floodgate once said, “90% of our exit profits have come from pivots.” ONSET Ventures also found in its research1 that founded the institution back in 1984 (prescient, I know) that there is a 90% correlation between success and the company changing its original business model.

All to say, one’s first idea may not always be the best and final idea. So, test things. With small audiences. With trusted confidants.

And while I may not do this all the time, with my bigger blogposts (like this, this, and this), I always run it by co-conspirators, subject-matter experts, lawyers, writers, bloggers, and people who love reading fine print. And sometimes the final product may not look like the one I initially intended, which will be true for an upcoming bigger blogpost. For events, like one I recently worked with the team at Alchemist on — redefining what in-person Demo Days look like at accelerators, we tested the idea with 20 other investors and iterated on their feedback before launching on January 30th this year. And still is not even close to its final evolution.

As Reid Hoffman once said, “If you are not embarrassed by the first version of your product, you’ve launched too late.”

Now that it’s out there…

One of the greatest Joker lines in The Dark Knight is: “Trust no one, salt and sugar look the same.”

It’s true. Whether people like something or not, they’ll always tell you things were good. It’s the equivalent of when one goes to a restaurant, orders something that’s a bit saltier than one’s liking, but when the server comes by to ask, “How is everything?”, most people respond with “Everything’s fine.” Or “good.”

You’re not going to get the real answer out of people oftentimes. Unless people really do love or hate something you did passionately. So… you must hunt for them. You must lure out the answers. You need to force people to take sides. There can be and shouldn’t be middle ground. If there are, that means they don’t like it.

Maybe it’s in the form of the NPS question. On a scale of 1-10, how likely would you recommend this product to a friend? And you cannot pick 7.

In the event space, I’ve come to like a new question. If I invited you to this event the week of, would you cancel plans to make this event? And to add more nuance, what kinds of events would you cancel to be here? What kinds of events would you not cancel?

Sometimes it helps to seed examples on a spectrum (although I try not to lead the witness here). Would you cancel a honeymoon? Or would you cancel going to another investor/founder happy hour? What about an AGM (annual general meeting, annual conference in VC talk)? What about a vacation?

As Joker said, salt and sugar look the same. So you have to taste it. Looking from afar won’t help. And if you want to iterate and improve, you need what people really think. I’d rather have people hate or dislike something I’ve created than have a lukewarm or worse, a “good” reaction.

In a way, if you’re not getting enough of an auto-immune response from the crowd, and the antibodies don’t start kicking in (aka the naysayers), you’re not really doing something new.

Photo by Roméo A. on Unsplash

1 FYI, the research link redirects to its HBS case study, not the original research. Couldn’t find the latter unfortunately. But the point stands.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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Lessons from Season 1 of Superclusters

microphone, podcast

I’m in my fourth year of writing this blog and never once have I called myself or identified as a content creator. As many of you know, I write to think. I do so out of joy and intellectual stimulation. In many ways, I write for myself. Or better put, as a form of self-expression. Other than posting in the morning, as is thematically helpful for my blog, I don’t really have much cadence to posting. Nor have I looked too deeply on analytics. Nor have I really optimized for SEO. In other words, finding the top searched topics in my industry and writing a blogpost for each of those highly trafficked keywords. I haven’t done that, nor do I want to. I haven’t chased people down to subscribe. In fact, there are times I try to convince people to not subscribe (due to the scattered nature of my content).

To that end, I had not been a content creator.

But with the launch of Superclusters, for the first time, and still a work-in-progress, I am designing the content for someone other than my immediate self. Although, do I take opportunities to scratch my own itches? Yes… yes I do.

But in doing so, I am starting to think about creating content for others. And to do that, I need to look at what people like and tune in to.

Now at the end of Season 1, some quick learnings…

Note: The below gets a bit nerdy on numbers. Mostly as an accountability metric to myself to be paying attention to the below. This may not be for everyone, but in case you’re curious, and/or working on creating your own content, hopefully the below might be helpful.

  • Between all the platforms, YouTube seems to be the most popular channel. Followed by Apple Podcasts then Spotify. Where Apple Podcasts only has half or so the number of plays than YouTube does. And Spotify has three-quarters the listens compared to Apple.
    • May be helpful to note that YouTube and Apple Podcast count plays as just someone viewing the video for a split second (“greater than 0 seconds”), whereas Spotify counts a play as someone who’s played the episode for at least 60 seconds.
  • YouTube seems to be better for discovery than the other podcasting platforms, with over 4.5X the impressions compared to the next best, Spotify. 28K versus 6K. Tracked by last 30 days, not all time.
  • For short-form vertical content, TikTok continues to perform better than both YouTube and Instagram, especially for new audiences. Still perplexes me since I imagine the demographic on YouTube has more of my intended audience. Nevertheless, even on YouTube shorts, the shorts are consumed by a younger audience than the long-form videos on average.
  • Instagram, in general, performs poorly in terms of discovery among new audiences. But that might simply be, I haven’t learned the IG algorithms well enough yet. Moreover the new algorithm seems to prioritize completion percentage. And given that it’s hard to shorten even my short-form content to less five seconds or less, unless I just make people read while playing some kind of looped video in the background, Superclusters will likely continue to perform poorly on IG.
  • On YouTube, 90%+ of Shorts viewership comes from non-subscribers than subscribers. where 75-80% come from non-subscribers, the average for the full podcast episodes.
  • On YouTube, 41% of my audience comes from the US. TO break it down further, 50% comes from the US for long-form. 27% for short-form. Spotify, 67% comes from the US. Apple Podcasts, 87%.
  • Interestingly, by city, according to Apple Podcasts, New York City takes the cake on where my audience reside.
  • Across all platforms, most of my listeners/viewers are in the 35-44 age range. Accounting for almost 50% across all platforms. Followed by the 28-34 age group, then 45-59 age group. In general, Superclusters has a larger younger audience fan base on YouTube, compared to Spotify and Apple Podcasts. The latter two with similar distributions.
  • Superclusters audience is also about 75% male, 25% female.
  • While less than 0.05%, fun fact, the only other subtitles used on YouTube to tune into my podcast was French (outside of English).

Popularity versus watch time

The most popular episode on YouTube is Chris Douvos’, followed by Ben Choi’s. Episode 1 and Episode 6 respectively. My suspicion was that while both were super fun to record, Chris’ episode came first but may by the end of Season 2 be surpassed in viewership by Ben’s.

On Apple Podcasts, it’s Samir Kaji’s. And on Spotify, it’s the post season episode with Jeff Rinvelt and Martin Tobias.

But what’s most fascinating to me is that among the nine episodes released for Season 1, on YouTube, the top four most popular episodes have shorter average watch times than the most bottom five. On average a two- to three-minute difference, where the least watched episodes happen to have 7-8 minutes of average watch time.

In closing

All in all, there’s a lot of work to do ahead. And as I’m recording Season 2 and my team is hard at work in editing those episodes, all of the above insights are helpful to keep my finger on the pulse. Do let me know if I’m missing any areas I should be paying attention to or measuring.

Otherwise, for Superclusters, I’ll see y’all again in early March for the launch of Season 2.

Keep staying awesome!

Cover photo by israel palacio on Unsplash

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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#unfiltered #75 Why I Write Long Form Blogposts

typewriter, blog, write

This past Wednesday, I was having lunch with an artist-turned-VC. And as you might imagine, we had to cover every topic at the intersection of art and startup investing. But of all the ground we covered, one stood out — content creation.

She’s on the Gram, LinkedIn, and everything in between. (Although surprisingly not on Twitter.) But to help her focus, she uninstalls those apps on her phone. Otherwise, she says she’ll end up “doomscrolling.” I get it. In fact, many of my friends and colleagues have shared similar things as well. But…

I’m weird. At least among my friend group, I’m really weird. I’m terrible at social media. I’m an 80-year old stuck in a 27-year old body. At least on the social media front. I find it so hard to keep my attention on social. In fact, I schedule ten minutes three times a week to hold myself accountable to be on LinkedIn and Twitter.

So, when it came to sharing my thoughts and learnings publicly, it was a pretty easy decision. Of course, I eventually came to self-rationalize it as the ability to own my own piece of virtual real estate, but there are three more reasons I chose blogging rather than tweeting or social posting.

1. I write to think

I’ve written about this before so I won’t elaborate in length on my own rationale here, but share a few examples of others also holding it in high regard.

There’s only so much you can flush out in just 280 characters, or over any short post. And while some of my thoughts fully flushed out may only be that long or less, not having that restriction gives me peace of mind to not hold back.

One of my favorite George Orwell lines happens to be: “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”

On that same wavelength on writing, Jeff Bezos makes Amazon execs write six-page memos. In most companies, team members often resort to PowerPoint presentations. Take anywhere between five and ten slides. Maybe less, maybe more. It’s much less thought out than a six-page dissertation. As Bezos says, “The reason writing a ‘good’ four page memo is harder than ‘writing’ a 20-page PowerPoint is because the narrative structure of a good memo forces better thought and better understanding of what’s more important than what.”

Equally so, it’s the same reason the best investors write memos for their investment decisions. My favorite public ones are Bessemer’s, which encapsulates much of their thinking at the time in amber. Turner Novak also turned his ability to write great memos to eventually raising his fund, Banana Capital. And the great Brian Rumao writes memos not just pre-investment, but also in his post-mortems where he gathers his learnings.

While I won’t go as far as to comparing myself to the afore-mentioned, I do find great pleasure and great learning from putting words on paper.

2. Longer feedback loop

My writing is more often a form of self-expression, self-curiosity, and self-discovery. So, unlike a product manager or founder who’s relentlessly testing and iterating on feedback, I enjoy longer feedback loops. I may start another content engine at some point that is for a particular audience, focused on feedback and iteration. But this humble piece of virtual estate will stay me. With no algorithm conditioning my attention span and yearn for external validation. That’s not to say I won’t ever (or have not ever) written things that you my awesome readers want, but it is only at the intersection of what you want and the what I enjoy writing about and asking others about that mint content here.

I also spend a lot of time thinking about audience capture, a term Gurwinder brought to my attention in an essay he wrote about Nikocado Avocado, which I also touched on in an essay I wrote near the end of last year.

I’m reminded by something Gurwinder wrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:

“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”

3. The impermanence of social media

Most things on social media are ephemeral in nature. It’s designed to capture the moment, but not chronicle the moments. On Twitter, you can only pin one tweet. On Instagram, you can pin three. And on LinkedIn, only three are visible on the featured carousel, and include, five max before it takes you down another layer of friction to discover more.

There’s a level of impermanence which makes thoughts feel whimsical rather than evergreen. To use a phrase I recently heard Tim Ferriss use, the “durability of the signal seems to wane so quickly.” And that made my thoughts feel cheap.

That’s not to say every post I write has their weight in gold, but the searchability and the evergreen nature of my favorite blogposts (saved in my “About” tab) are the reasons I keep most of my thoughts here.

Photo by Fiona Murray on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

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How to Win at Net Dollar Retention

coffee shop, retaining customers

I was reading Sammy Abdullah of Blossom Street Ventures‘ Medium post not too long ago about the value of auto-price increases in a context I’ve never really thought about. Quoting one of his portfolio companies’ founders:

“We started including auto-price increases in our renewals at the start of this year and it’s been surprisingly effective. Our starting point is 10% and we get it more often than not; some customers negotiate us down to the 3–5% range.

“The automatic price increases are a beautiful thing because they give us leverage:

  1. we can trade an automatic price increase for an earlier renewal, longer contract period, or upselling to more features; and
  2. when we do waive price increases, the customer walks away satisfied. They feel like they’re winning.”

It’s a great way to win on net retention. But as I’ve written about before, the net retention equation is comprised of the upgrades, downgrades, and churn variables.

NDR = (starting MRR + upgrades – downgrades – churn)/(starting MRR)

So to maximize retention, you can:

  1. Level up your customers into higher tiers
    • Or convert more users into customers, if you’re running a freemium model
  2. Reduce the number of customers downgrading to lower tiers
  3. Reduce churn – customers leaving your platform
  4. Some permutation of the above variables

Leveling up upgrades

Shivani Berry, founder of Ascend’s Leadership Program, once wrote: “Buy-in is the result of showing your team why your idea achieves their goals.” In a similar sense, buy-in is the result of showing your customers why your product achieves their goals. The best thing is that their goals will change over time. As so, your product must contain increasingly more value to your customers as they level up in their lifecycle. As they grow, you have product offerings that grow with their needs.

Take, for example, one of my favorite startups these days, Pulley, a cap table management tool for startups. Don’t worry, this isn’t a sponsored blogpost. Although it’d be nice if it was. I have no chips in the bag; I just like them. They have three tiers of pricing. The lowest for startups with 25 stakeholders. The middle for startups with 40. And the highest is for larger businesses.

Why 25? The average seed-stage startup has about 25 stakeholders. Subsequently, top of mind for them is what SAFEs and convertible notes look like on their cap table and how to structure early equity pools.

As a startup levels up to 40 stakeholders, they’re probably jumping into their first priced round. As such, they’ll need a 409A valuation to appraise their fair market value, as well as finally putting together their first official board.

Every time founders raise another round of funding, the more complicated their cap table becomes. The more they need Pulley’s software. And it so happens, the less price sensitive they become. For Pulley, that means they can charge more as their customers have greater purchasing power.

You also always want an enterprise pricing tier, where pricing is custom. Don’t be afraid to charge more. As I mentioned in a previous essay, when Intercom was only charging IBM $49, an IBM exec once told the Intercom team, “You know, I go on a coffee run for the team that costs a lot more than your product. That’s why we’re wary of investing too much more in you. We just don’t see how you’re going to survive.” If it helps as a reference point, the median ACV (annual contract value) for public SaaS companies is $27,000.

Do note that the more you charge, the longer the sales cycle will be. For ACVs over $20K, expect 4-6 months of a sales cycle. For contracts over $100K, expect 6-9 months. Of course, the contrapositive would be that the lower the price point, the easier and faster it takes to make a decision.

Reducing downgrades and churn

I’ve been in love with Clayton Christensen’s “jobs-to-be-done” (JTBD) framework ever since I learned of it a few years ago. At the end of the day, you’re delivering value. Value in the form of doing a job. As Christensen says, “when we buy a product, we essentially ‘hire’ it to help us do a job. If it does the job well, the next time we’re confronted with the same job, we tend to hire that product again. And if it does a crummy job, we ‘fire’ it and look for an alternative.”

The better it can do the job your customer needs to get done, the more you can optimize for the variables in the net retention equation. Sunita Mohanty, Product Lead at Facebook, shared an amazing JTBD framework they use back at Facebook and Instagram:

When I… (context)
But… (barrier)
Help me… (goal)
So I… (outcome)

Here’s another way to look at it:

  1. What features should we have that would make our product great?
  2. What features should this product have that would make it a no-brainer purchase for our customers?

The “no-brainer” part especially matters. And to be a “no-brainer”, you have to deliver the best-in-class. Your features have to solve a fundamental job that your customer is trying to solve. The difference between a “great product” and a “no-brainer” is the difference between a 5 out of 5-star rating and a 6-star out of a 5-star rating. Effectively, the outcome in Facebook’s JTBD framework exceeds the goal, which makes the barrier irrelevant. As David Rubin, CMO of The New York Times and former Head of Global Brand at Pinterest once said: “Your service shouldn’t lead with ‘saving money’. You must create an offering that is so compelling, it stands by itself in the consumer’s mind.”

In closing

At the end of the day, in the words of Alex Rampell, building a startup is “a race where the startup is trying to get distribution before the incumbent gets innovation.”

You’re in a race against time. You’re trying to reach critical mass and growth before your incumbents realize your space is a money-making machine. And growth comes in two parts: acquisition and retention. While many founders seemed to have over-indexed on acquisition over the last couple of years, the pandemic has reawakened many that retention is often times much more difficult to attain than acquisition. While it may not be true for every type of business, hopefully, the above is another tool in your toolkit.

Photo by Joshua Rodriguez on Unsplash

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The Puzzle Pieces

In the first decade of my life, my parents used to buy me different kinds of puzzles – from the Rubik’s cube to beautifully intricate LEGO sets to Luban locks. One of my favorites has always been these thousand-piece puzzles. Every time I poured those pieces out of the box, they scattered across our carpet like tiny ants scrambling to find meaning. I loved putting the puzzle together having only seen the completed image once – when I opened the box. That probably, at most, left a three-second impression in my mind. How awesome would photographic memory be. But alas, it wasn’t something I’d been blessed with. I only found out years later from friends that it wasn’t normal. That said, I imagine I took much longer than most people to piece together the whole puzzle.

Fresh out of the box, I start off knolling the various incongruous shapes. Like most others, I’m looking for similar designs, colors, lines, images – anything. Trying to make sense of disparate pieces. Frankly, I was drawing parallels wherever and whenever I found them. A more mature me would call it – pattern recognition.

As I progress, I spy colonies of color form in different areas on the living room floor. And therefore, try to see if any colonies, together, would tell a more robust, vibrant story. Sometimes I was right. Sometimes I was wrong.

As I near the end of the puzzle, I see everything come together. I’m not gonna lie. It’s extremely gratifying to see the rough picture in my head come to life. Often times, the final image has minor deviations from the loosely-defined vision I had when I started.

You probably caught on

You’re smart, and you probably guessed what I was trying to get at before you even finished reading my anecdote. And you’re right. In many ways, this puzzle journey is very similar to building a company. You start off with an idea, constructed upon anecdotal patterns you’ve seen in the world you know. And as you build the idea and talk to customers – other nearby pattern aggregations – you start to piece together a larger and more concrete goal. By the time you reach scale, you’re filling in the little details – the extra puzzle pieces – you missed when focusing on the more holistic vision. The little details of debugging, solving edge cases, and improving the user experience.

Listen to the silence

The initial idea comes from recognizing the patterns around you. Both what is being said, and what isn’t. Both what is there and what could be there.

One of my favorite stories on pattern recognition is about Abraham Wald, a Hungarian-Jewish mathematician and statistician, who’s credited with saving the lives of numerous pilots and airmen during WWII. Tasked with aircraft armor repair, Wald, then a faculty at Columbia University, was given a number of data points on bullet holes in the fighter planes that returned to base. Most were around the fuselage and a few around the motors.

As one would expect, the military anticipated to double down armor around areas with the most damage – the fuselage. But Wald took a different angle. Reinforce the plate metal around the motors, rather than the fuselage. Because the planes that didn’t make it back most likely had bullet holes where the planes that did make it back didn’t.

Listen to the sound

Sometimes you’re right. Sometimes you’re wrong. And if you’re wrong, follow the breadcrumbs of your market. Notice what their use cases are and how they’re spending their time. Even better if they’re developing hacks to circumvent the early inefficiencies of your product. What features or problems are getting a lot of attention?

For instance, Stewart Butterfield didn’t start off with the idea for Slack. After selling Flickr to Yahoo! and working at Yahoo! for three years after, he started with Tiny Speck, a gaming startup that raised $17M in venture funding to build Glitch. Unfortunately, it didn’t take off, outside of its cult following. But what did stick was the tool Stewart and his team had been using to chat in real-time with each other. Less than a year after it officially launched, it hit a $1B in valuation. Six years later, it became Salesforce’s biggest acquisitions at over $27B. And history is still being written.

Similarly, Kevin Systrom didn’t start off with Instagram. But rather Burbn – a location-based check-in app. Users would check-in, plan future meetups with friends, share pictures of their meetups, and earn points in the process. Unfortunately, the app was too complicated for the average user to use. After bringing on Mike Kreiger and analyzing how their users were using the app, they realized most of their traffic happened around posting and sharing photos. Scrapping everything else, they focused on their biggest use case – photo-sharing. And well, they were right on the pivot. In 2012, right before Facebook’s IPO, Facebook acquired Instagram for $1B. It was big then, but as we all know now, it’s even bigger now.

Back in 2012, Kevin once said, “It’s about going through false starts… Brbn was a false start. The best companies in the world have all had predecessors. YouTube was a dating site. You always have to evolve into something else.”

In closing

I love people who binge. It’s a sign that they capable of going all in and more on something they’re passionate about. I, myself, have binged time and time again on puzzles, shows, books, passion projects, and more. For Stewart, it was games. For Kevin, it was whiskey and bourbon. On the other hand, for Abraham, I can’t quite say. I have no idea if he was into plate armor or planes, but whether he liked it or not, he probably spent sleepless nights on it.

And in the process of binging, if you keep my mind and my senses open to inspiration, you may uncover some patterns in the mix. ‘Cause if you’re going to notice what’s being said and not said between the lines, you’re going to have to be in deep. Deep enough to take your breath away, but not deep enough to take your sight away.

Photo by Ross Sneddon on Unsplash

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v24.0

Photo by Ian Schneider on Unsplash

My parents have always conditioned me to plan each of my ages out. When I was younger, every year I ranked up they would ask me what I want to get done. At the same time, I never felt a strong commitment to New Year’s resolutions. Maybe it was ’cause of the gingerbread cookies. Or the Christmas presents. Or the fireworks and the ball drop. But that lull between the holidays wasn’t conducive to me setting meaningful goals. The “promises” I made carried no weight behind them.

Three years back, after reading Brad Feld’s birthday resolution, I decided to start setting my own birthday resolutions. Outside of a mere date shift, there were 3 reasons I chose to do so:

  1. I had time to recover from the holidays – to get my head straight.
  2. I was motivated watching my friends, family, and coworkers tackle their New Year’s resolutions in the month prior. (Admittedly, more often than not, they lose their initial trajectory, but I only saw the beginning of many of their inverse parabolas.) Motivation is one side of the coin; FOMO is another.
  3. In that motivating January, assuming I haven’t yet completed my previous year’s resolution(s), it motivates me to finish strong – the “last mile” sprint.

That said, this is my first year posting my resolutions publicly. Why? One, it’s to keep me accountable. Two, as Jeff Wald once said, “practice true vulnerability by opening up about the potholes ahead, not just the ones in the rearview mirror.” And one of my resolutions from v23.0 was to become more comfortable being vulnerable. So, what will the new update look like?

Here are the patch notes:

Build ideas from 0 to 1.

This year, I plan to actively help 2 startups go from idea to product-market fit. After 3 years on the venture side of the cap table, the one thing I’ve noticed more and more is that I miss getting my hands dirty, especially in the early stages. I miss the ups and downs. I miss the freaky moments (and the big wins). It may sound a bit weird. But I may have emotionally removed myself from being entrepreneurial and trapped myself in a bird’s-eye perspective only. And I hate it.

More artistically creative outputs.

Two years ago, I started idea-journaling by inspiration from my former college professor. After going through 9.5 idea journals, I realized I’ve spent less than 10% of my ideation space on artistic pursuits. 40% on VC and startups. 40% on personal projects and experiments. 10% everything else. There’s clearly a lack of diversity in my creative space. So, this year, I’m committing to producing one new art piece every week – be it a new drawing, music composition, culinary permutation, or something that’ll surprise myself. My deepest gratitude to my friends who gave me new canvases to explore my creative white space. You can track my progress on my Instagram.

Balancing Social Media.

In the year when many of my peers are unplugging, I’m going to be more active on social media, fine print included. I’m going to explore more by contributing content on this blog, my Instagram (for artistic pursuits), LinkedIn, Medium, Quora, Reddit, and Discord.

I’ve always shied away from social media – not because of some grandiose sense of self-discipline, but rather since I’ve never been able to fully conquer my shell of introversion. After all, my Facebook profile picture and lack of presence is my form of psychological armor.

That said, I still won’t be scrolling through my news feed on social media. But I will aim to respond to every comment and DM that comes my way. I’m a firm believer in responding to the commitment and time people take to write a thoughtful message. Luckily, I’m also at a stage in my life and career when I don’t have more messages/emails than I can manage.

Reconnecting.

Over the past half decade, I’ve grown a lot from reaching out to, learning from, and helping new folks in my network. And, I’m grateful for each and every experience. I wouldn’t be here today if it weren’t for them. But as a result of constant pursuits of new experiences and expanding my network, I haven’t been able to reconnect with friends, mentors, teachers, and acquaintances I’ve had in the past, outside of my annual holiday greetings and thanks. In this new update, I’m committing 10 minutes every day to meaningfully rekindle old flames that I haven’t caught up with in the past 6 months.

Read more.

By virtue of reconnecting with friends from my past, it’s useful to have content and inspiration when reconnecting, but also as a means to widen my own knowledge horizon. Outside of work and my one-book-a-month of reading, I’ll be indulging in a minimum of an hour of diverse reading every day via the ‘Discover’ tab on Pocket.

Sleep and wake earlier.

Ever since college, I’ve been a night owl. It’s weird ’cause in college, students apparently have this ego contest of how many ‘all-nighters’ one can pull and still be ‘alive’. Being young and naive, I joined in the chorus, but I never won. In fact, in my entire college career, I pulled only 2 all-nighters, not even back-to-back, and I was already dead. But it ended up ruining my sleep schedule. I would go to sleep between 12 and 3AM. Sometimes for no reason at all.

After I came back from my holiday Europe trip, mostly due to jet lag, I started sleeping at 9PM every night for the first week. I felt so much more refreshed in the morning and through most of the day than when I didn’t. But also, there’s so much less noise in the morning between 4:30 and 6:30AM – both on social media and in the neighborhood. And I could much of my creative work done. This year, I’m going to sleep at 10PM latest and wake at 4:30AM.

Goal-oriented exercise.

I haven’t necessarily been unfit, but my daily routines seem to drone by without any personal achievement or goal in mind. I have no plans to reach my past physical prowess where I spent 30-40 hours a week spent on exercise. But this year, I’ll stick to 2 goals for health and exercise: sub-5:30 mile and 20 pull-ups. (I’m at a 7:15 and 7 pull-ups at the time of writing this post.)

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It’s going to be an exciting year, and I plan to have plenty of hotfixes before I reach v25.0, hopefully daily. Thank you to my friends for all the birthday wishes, support, and feedback.

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