Good Misses and Bad Hits

basketball shot, swoosh

The espresso shot:

  • What are the essential elements of a “good” VC fund strategy vs. “lucky”?
  • What elements can you control and what can you not?
  • How long does it take to develop “skill” and can you speed it up w/ (intentional) practice?

Anyone can shoot a three-pointer every once in a while.

Steph Curry is undeniably one of the best shooters of our time. If not, of all time. Even if you don’t watch ball, one can’t help but appreciate what a marksman Steph is. In case you haven’t, just look at the clip below of his shots during the 2024 Olympics.

From the 2024 Olympics

As the Under Armour commercial with Michael Phelps once put it, “it’s what you do in the dark that puts you in the light.” For Steph, it’s the metaphoric 10,000 hours taking, making, and missing shots. For the uninitiated, what might be most fascinating is that not all shots are created equal, specifically… not all misses are created equal.

There was a piece back in 2021 by Mark Medina where he wrote, “If the ball failed to drop through the middle of the rim, Curry and Payne simply counted that attempt as a missed shot.” Even if he missed, the difference between missing by a wide margin versus hitting the rim mattered. The difference between hitting the front of the rim versus the backboard or the back rim mattered. The former meant you were more likely to make the shot after the a bounce than the other. Not all misses are created equal.

Anyone can shoot a 3-pointer. With enough tries. But not everyone can shoot them as consistently as Steph can.

The same holds for investing. Many people, by sheer luck, can find themselves invested in a unicorn. But not everyone can do it repeatedly across vintages. It’s the difference between a single outperforming fund and an enduring firm.

The former isn’t bad. Quite good actually. But it also takes awareness and discipline to know that it may be a once-in-a-lifetime thing. The latter takes work. Lots of it. And the ability to compound excellence.

When one is off, how much are you off? What are the variables that led you to miss? What variables are within your control? And what aren’t? Of those that are, how consistent can you maintain control over those variables?

As such, let me break down a few things that you can control as a GP.

Are you seeing enough deals? Are you seeing enough GREAT deals? Do you find yourself struggling in certain quarters to find great deals or do you find yourself struggling to choose among the surplus of amazing deals that are already in your inbox? Simply, are you struggling against starvation or indigestion? It’s important to be intellectually honest here, at least to yourself. I know there’s the game of smokes and mirrors that GPs play with LPs when fundraising, but as the Richard Feynman line goes, “The first principle is that you must not fool yourself—and you are the easiest person to fool.”

Whereas deal flow is about what companies you see, value add is more about how you win deals. Why and how do you attract the world’s best entrepreneurs to work with you? In a world where the job of a VC is to sell money – in other words, is my dollar greener or is another VC’s dollar greener – you need to answer a simple question: Why does another VC fund need to exist?

What can you provide a founder that no other, or at least, very few other, investors can

While there are many investors out there who say “founders just like me” or “founders share their most vulnerable moments with me”, it’s extremely hard for an LP to underwrite. And what an LP cannot grasp their head around means you’ll disappear into obscurity. The file that sits in the back of the cabinet. You’ll exist, and an LP may even like you, but never enough for them to get to conviction. And to a founder, especially when they’ve previously “made it”, already, you will fall into obsolescence because your value-add will be a commodity at scale. Note the term “at scale.” Yes, you’ll still be able to win deals on personality with your immediate network, and opportunistically with founders that you occasionally click with. But can you do it for the three best deals that come to your desk every quarter for at least the next four years? If you’re building an institutional firm, for the next 20+ years. Even harder to do, when you’re considering thousands of firms are coming out of the woodwork every year. Also, an institutional LP sees at least a few hundred per year.

For starters, I recommend checking out Dave’s piece on what it means to help a company and how it impacts your brand and perception.

Deal flow is all about is your aperture wide enough. Are you capturing enough light? Portfolio size is all about how grainy the footage is. With the resolution you opt for, are you capturing enough of the details that could produce a high definition portfolio? In venture, a portfolio of five is on the smaller side. And unless you’re a proven picker, and are able to help your companies meaningfully or you’re in private equity, as a Fund I, you might want to consider a larger portfolio. It’s not uncommon to see portfolios at 30-40 in Fund I that scale down in subsequent funds once the GPs are able to recognize good from great from amazing.

I will also note, with too big of a portfolio, you end up under optimizing returns. As Jay Rongjie Wang once said, ““The reason why we diversify is to improve return per unit of risk taken.” At the same time, “bear in mind, every fund that you add to your portfolio, you’re reducing your upside as well. And that is something a lot of people don’t keep in mind.”

Moonfire Ventures did a study in 2023 and found that “the probability of returning less than 1x the fund decreases as the size of your portfolio grows, and gets close to zero when your portfolio exceeds 200 companies.” That said, “it’s almost impossible to 10x a fund with more than 110 companies in your portfolio.”

While there’s no one right answer in the never-ending diversified versus concentrated debate, nevertheless, it’s worth doing the work on how size and the number of winners in your portfolio impact returns.

First off, how are you measuring your marks? Marc Andreessen explains the concept of marks far better than I can. So not to do the point injustice, I’m just going to link his piece here.

Separately, the earliest proxies of portfolio success happens to revolve around valuations and markups, but to make it more granular, “valuation” really comes down to two things:

  1. Graduation rates
  2. Pro rata / follow-on investments

When your graduation rates between stages fall below 30%, do you know why? What kinds of founders in your portfolio fail to raise their following round? What kinds of founders graduate to the next stage but not the one after that? Are you deeply familiar with the top reasons founders in your portfolio close up shop or are unable to raise their next round? What are the greatest hesitations downstream investors have when they say no? Is it the same between the seed to Series A and the A to B?

Of your greatest winners, are you owning enough that an exit here will be deeply meaningful for your portfolio returns. As downstream investors come in, naturally dilution occurs. But owning 5% of a unicorn on exit is 5X better than owning 1% of a unicorn. For a $10M fund, it’s the difference for a single investment 1X-ing your fund and 5X-ing it.

When you lose out on your follow-on investment opportunities, what are the most common reasons you didn’t capitalize? Capital constraints? Conviction or said uglier, buyer’s remorse? Overemphasis on metrics? Lack of information rights?

Then when your winners become more obvious in the late stages and pre-IPO stages, it’s helpful to revisit some of these earlier decisions to help you course-correct in the future.

I will note with the current market, not only are the deal sizes larger (i.e. single round unicorns, in other words, a unicorn is minted after just one round of financing), there are also more opportunities to exit the portfolio than ever before. While M&A is restricted by antitrust laws, and IPOs are limited by overall investor sentiment, there have been a lot of secondary options for early stage investors as well. But that’s likely a blogpost for another day.

To sum it all up… when you miss, how far do you miss?

Obviously, it’s impossible to control all the variables. You cannot control market dynamics. As Lord Toranaga says in the show Shogun when asked “How does it feel to shape the wind to your will?”, he says “I don’t control the wind. I only study it.” You can’t control the wind, but you can choose which sails to raise, when you raise them, and which direction they point to. Similarly, you also can’t completely control which portfolio companies hit their milestones and raise follow-on capital. For that matter, you also can’t control cofounder splits, founders losing motivation, companies running out of runway, lawsuits from competitors, and so on.

But there are a select few things that you can control and that will change the destiny of your fund. To extend the basketball analogy from the beginning a bit further, you can’t change how tall you are. But you can improve your shooting. You can choose to be a shooter or a passer. You can choose the types of shots you take — 3-pointers, mid-range, and/or dunks. In the venture world, it’s the same.

The choice. Or, things you can change easily:

  1. Industry vertical
  2. Stage
  3. Valuation
  4. Portfolio size
  5. Check size
  6. Follow-on investments

The drills. Or, things you can improve with practice:

  1. Deal flow – both quantity and quality
  2. The kinds of deals you pick
  3. Value add – Does your value-add improve over time? As you grow your network? As you have more shots on goal?
  4. The deals you win – Can you convey your value-add efficiently?

And then, the game itself. The things that are much harder to influence:

  1. Graduation rates
  2. Downstream dilution
  3. Exit outcomes
  4. The market and black swan events themselves

Venture is a game where the feedback cycles are long. To get better at a game, you need reps. And you need fast feedback loops. It’s foolhardy to wait till fund term and DPI to then evaluate your skill. It’s for that reason many investors fail. They fail slowly. While not as fast of a feedback loop as basketball and sports, where success is measured in minutes, if not seconds – where the small details matter – you don’t have to wait a decade to realize if you’re good at the game or not in venture. You have years. Two to three  What kinds of companies resonate with the market? What kinds of founders and companies hit $10M ARR? In addition, what are the most common areas that founders need help with? And what kinds of companies are interesting to follow-on capital?

Do note there will always be outliers. StepStone recently came out with a report. Less than 50% of top quartile funds at Year 5 stay there by Year 10. And only 3.7% of bottom-quartile funds make it to the top over a decade. Early success is not always indicative of long-term success. But as a VC, even though we make bets on outliers, as a fund manager, do not bet that you will be the outlier. Stay consistent, especially if you’re looking to build an institutional firm.

One of my favorite Steph Curry clips is when he finds a dead spot on the court. He has such ball control mastery that he knows exactly when his technique fails and when there are forces beyond his control that fail him.

Source: ESPN

Cover photo by Martí Sierra on Unsplash


Huge thanks to Dave McClure for inspiring the topic of this post and also for the revisions.


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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.

#unfiltered #70 Conviction Comes From The Stories We Tell Ourselves

focus, conviction, motivation

On the second half of a late summer Friday, as I was overlooking the singed blades of the parched grass in our front yard, I found my good friend, Andrew, in my inbox. An inbox that was about to be empty from filing an eclectic collection of investor updates, food science analyses, tech articles, and my weekly subscription of Substack extraordinaires into my Read Later folder.

An email headline in boldface. All it would take would be two clicks. Two clicks to add to my party of internet writers I would be conversing with over a Saturday morning of roasted hojicha tea. Instead, I clicked once. Just once. And I’m glad I did.

Andrew started writing again. Pen to paper. Or rather, finger to keyboard. And that, that was worth celebrating. I, like many of his other friends, had been starved, deprived, relieved of his prose given his busy schedule. In it, he postulated the relationship between commitment and conviction.

“Commitment helps you stay on the path. Conviction is what calls you to the path in the first place.”

In sum, the pre-requisite for commitment is conviction. And so, it got me thinking about the source of conviction…

From inspiration

For decades, athletes have tried to break the 4-minute mile. According to British author John Bryant, since 1886. “It had become as much a psychological barrier as a physical one. And like an unconquerable mountain, the closer it was approached, the more daunting it seemed.”

But it wasn’t till May 6, 1954, did Roger Bannister break it with a time six-tenths under the mark. As soon as Bannister did it, 46 days later, another did. One year later, three runners broke the once elusive 4-minute barrier in one race.

The thing is, nothing technological had changed in the world when all these runners post-Bannister broke the four minutes. Nutrition hadn’t drastically improved. Neither was there drastic evolution in the technology of shoes. Yoram Wind and Colin Crook argues it was a mindset shift. The impossible was possible.

We see the same notion today in the world of emerging markets. In these markets, the first wave of unicorn founders is usually spearheaded by Harvard and Stanford grads building X for Latam or Y for Africa. For instance, both of Grab’s founders are HBS graduates. Gojek’s Nadiem is no exception. Nubank’s David Velez holds a similar Stanford GSB degree. So does Cabify’s Juan de Antonio. Rappi’s founders are also Stanford alumni. And the list goes on. They come with the Silicon Valley mindset in a market underestimated by not only the broader world but by the homegrown talent themselves. I like the way a Midwest founder-turned-investor once put it, “My mind is in Silicon Valley, but my feet are in the Midwest.” The same is true for this first wave.

And once they’ve proven it’s possible to reach unicorn status, the second wave follows quickly after.

Most people follow in the footsteps of our predecessors. Older siblings are the same for their younger siblings. Parents are that for their children. While I’m not a parent yet myself, I do aspire to be that for my children. Equally so, that’s why we need diverse representation in media, in positions of power, and in stories.

For many, conviction comes from examples to disprove the limitations of our own imagination.

From emotion

For a handful of others, conviction comes from a deep desire to prove or disprove.

There’s a superpower that comes with being underestimated. Reddit’s founders famously hung on the office walls the words of a Yahoo! exec who told them,  they were nothing but a “rounding error.”

When Michael Phelps’ eight gold medals in Beijing were on the line, their coach Bob used what the French team was boasting on the papers as motivation in the locker rooms. “The Americans? We’re going to smash them. That’s what we came here for.” And soon after, the world was blessed with one of the greatest races to date. A race of which the Americans — the underdogs — pulled a miraculous spectacle of conviction and resolve.

For founders, you need obsession, not just passion. Many of the best ones have a personal vendetta — a deep, unquenchable desire borne out of time spent in the idea maze. Every successful founder needs to perform 10-15 miracles in the startup to household name journey. Trials by fire that are meant to deter the fainthearted.

After chatting with a number of limited partners (LPs, folks who invest in venture funds) over the past two months, I’ve realized the thread of founder obsession continues here. That investor-market fit is not just a function of professional experience but also of life experience. Once again, a deep desire to change the world from personal frustrations and the hope that no one will ever have to go through what they went through.

In closing

Earlier this year, Reed Hastings shared a profound line with the graduating class, “[stories are] about harnessing the human spirit.” Conviction starts from the story we tell ourselves. The story itself is bound by the limitations of our own imagination. And conviction happens to be the belief that we can will our imagination into existence.

Michelangelo once said, “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.” Commitment is the dedication to your conviction. A devotion to say no to distractions and yes to the person you want to be.

We live in a world filled with shiny objects. So, ask yourself, do you want what others want? Or what you truly want? Is your conviction inherited or innate?

I was listening to the latest episode of the All-In podcast, and David Friedberg echoed a similar notion for the greater human race, “What differentiates humans from all other species on Earth is our ability to tell stories. A story is a narrative about something that doesn’t exist. And by telling that narrative, you can create collective belief in something. And then that collective belief drives behavioral change and action in the world.”

Photo by Devin Avery 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!


Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

#unfiltered #55 Short Spurts of Motivation

motivation, walk

Over the past two weeks, I’ve been working on a new blogpost about self-doubt, which I expect will come out soon. Or rather, soonTM. At the same time, after watching a week’s worth of incredible aquatic talent, I saw as the era of the swimming greats I grew up with came to a close. Michael Phelps. Natalie Coughlin. Nathan Adrian. Allison Schmitt. Anthony Ervin. Jason Lezak. Cullen Jones. Kosuke Kitajima. Dara Torres. And much more.

They were part of the defining score of years that brought the sport into the limelight. To most, most of the above names carry little gravity, outside of Phelps. But to me, they were the names that had me huddled around the TV. Watching the prelims. The semis. And of course the finals. They were the names that inspired me to be better.

As Ervin said, “We are the oldest of the fastest and the fastest of the oldest. We are men between worlds.”

But as they came back for one last curtain call this Olympic Trials, I couldn’t help but recall their influence on me in some of my most formative years. Whether I need that extra push for the most challenging project in my life to date or that shoulder to lean on when I am at my worst, there’s one race I cannot help but think about.

Just like when a Yahoo! exec told the Reddit co-founders that they were a “rounding error” and the team subsequently decided to frame it on their office wall as motivation, in 2008, the US Olympic 4×100 freestyle relay team faced a similar dilemma. Despite having Phelps on the relay team, they weren’t the crowd favorites. The French were. They – the American team – were the underdogs.

In fact, that 2008, French team boasted some of the fastest sprinters in the history of the sport. Alain Bernard who had just won his gold in the 100 meter freestyle. And Amaury Leveaux who had taken the silver in the 50 meter freestyle. And besides Lezak who tied for bronze in the 100 meter freestyle, none of the others on the US team had medaled for a short-distance freestyle event that Olympics.

Pound for pound, the US relay team had to deliver not only their best, but beat their best. To have a chance at beating the French team. So for motivation, they read Bernard’s comment in the papers over and over. “The Americans? We’re going to smash them. That’s what we came here for.”

Phelps leads the race, giving his team a slight lead over France. Weber-Gale holds that lead for the Americans. Jones, the slowest and the third leg of the team, yet still punching every inch of his worth, gives the lead back to France. And Bernard, the world champion in the 100 free, against Lezak for the US, gets a strong lead for a race and a length he is already the best in the world at. Lezak trails behind by over half a body length at the flip. 50% done of the last leg of the race.

I remember sitting in front of the television screen, screaming and hoping my voice would reach the Water Cube in Beijing. “C’mon… c’mon! C’mon!!” Lezak, at 32, one of the oldest competitors in the pool that year, pulled together what could only be described as sheer willpower. Those last 50 meters… seemed to have been the longest 23 seconds of my life. A breath for every second that passed. A breath for every second Lezak pulled closer to Bernard. And in the last ten seconds, minus the sound of the TV, the room was silent. As some people might say, you could hear the sound of a pin drop. It did. With a margin of eight hundredths of a second.

One of the tightest and most inspiring races in all of history. If you ask me, the greatest. And the race I watch time and time again when I am at my worst.

You have to see it for yourself to really believe the excitement.

Top photo by Tegan Mierle 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!

Being the Only > Being the Best

crown, being the only, startup, marketing

This week I revisited David Sacks’ essay Your Startup Is a Movement. It was first brought to my attention during my conversation with Yin Wu, founder of Pulley. And again, with a friend who recently jumped into venture after an operating career, particularly around the topic of our investment theses. Our conversation underscored his fourth point in his Movement Marketing playbook.

david sacks, craft ventures, your startup is a movement, category leader
* Excerpt from David Sacks’ Your Startup Is a Movement

It’s much easier to compete in the market of one – the only one – than in a market to be the best one. As some VCs call it, companies that are “allergic to competition.”

Why?

The goal for any startup is to achieve product-market fit before your competitors, especially your incumbents, notice the market opportunity. Frankly, the incumbents have more cash, more talent, more resources, more in every regard except one… problem obsession. Insatiable desire to fundamentally change the way we live. And with that desire comes speed.

It reminds me of a time over a decade ago, right after the spectacular Olympics which put the greatest Olympian of all time on center stage. Our swim coach asked the team, “How do you beat Michael Phelps?”

A few of my teammates suggested we work longer and harder. Another suggested that we should’ve started younger. And another suggested we wait till he retired. But my coach responded, “Just don’t race against him in butterfly. Race him in breaststroke.” While Michael Phelps is by no means slow in breaststroke, still faster than 95% of swimmers out there in it, the theory holds. It’s the stroke one would have the best chance to beat him in. But what stood out to me most was what the wisecrack on the swim team shouted out as an answer.

“He can swim while I run.”

And he was right.

Another fascinating aspect I realized in hindsight was that no one suggested the question was impossible.

Photo by Ashton Mullins on Unsplash


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The Third Leg of the Race

swimming, the third leg

I dedicated three-quarters of my life before I turned 18 to swimming. More than half of which I spent competitively. Although I never amounted to a Michael Phelps or Katie Ledecky, the years I spent swimming were some of the happiest, yet character-building times of my life.

I was a mid-to-long-distance swimmer – anything between 200 yards (or meters) to miles-long open-water swims in the SF Bay. By golly, the waters in the latter ‘pool’ were dirty. I couldn’t see my own hand when I reached out underwater. But I digress. As a distance swimmer, the biggest lesson I learned was how to fight the mental battlefield.

The Legs of a Race

Coach taught me to break every race down into 4 quarters. The first leg, the second leg, the third leg, and the last leg.

The first leg is comparatively the easiest. You’re brimming with energy, motivation and (potentially nervous) excitement. As long as you don’t exhaust yourself in this leg, but put in enough effort to break away from the pack, you’re golden. And in doing so, you’re going at 80% of your top speed.

The second leg is when you start engaging in a psychological battle with your competitors. Understand where they are in the race, as well as their racing personas.

  • Are they a front-half or back-half swimmer?
  • Are they a sprinter from the blocks?
  • Do they typically negative split in a race?
  • In an individual medley (IM) race, what’s their best stroke? Their worst stroke?

I typically dial back to 70% speed.

The last leg is probably the second easiest. You burn everything and anything you have in the tank. The goal is in sight – within reach. It comes down to how well you’ve raced the first three legs, and how much you trained. Effectively, it is a battle of strength – a Hail Mary. 110% speed.

Now let’s rewind back to the crucial leg I skipped. The whole reason I started writing this post.

The Third Leg of the Race

Whereas the second leg is based on ‘external warfare’ and the last leg is based on ‘physical warfare’, the third leg, and arguably the most important, is one based on ‘internal warfare’. By this point in the race, you’ve exhausted more than half of your energy, yet you’re expected to output more than when you started. You’re worn and tired. And, you can’t see the goal yet, so you know you have to save some strength for the last leg.

Yet, if you can hold this leg, it can mean the difference between a win and a loss. If you lose this leg and succumb to your thoughts, your chances of winning are slim. Quite frankly, it sucks.

So I made bets with myself.

“If I can finish this lap in 14 strokes, where I’m reaching out and scooping that ice cream just out of my arm’s reach, I’m going to treat myself to some Haagen Dazs after. One scoop for every lap I succeed in.”

“I’m going to flip turn faster than my opponents. And if I can do this thrice in a row, I’m going to get rock-solid abs when I finish this race.”

“I’m going to hold my breath till the other side of the pool, so I can smell and taste the teriyaki chicken.” *At swim meets, they’re always selling teriyaki chicken and rice for lunch. It’s greasy, super salty. But if you add some sriracha, it is a hungry swimmer’s heaven.

As you might notice, some of my bets were outright ludicrous. But it was because they were crazy that I was motivated to keep going. When there were no tangible goals, I made my own.

Why am I sharing this?

Life, seeking employment, running a business, and so much more run in the same way. After your academic career, no one really tells you what your goals are or can be. You have to make your own. When you’re job-seeking and no interviews are coming your way, you have to muster the strength to continue applying – either spraying and praying or finding creative ways to obtain certain opportunities.

In startup land, day 1 till day 365 (or even till day 730) will be a honeymoon. It’ll be the first leg. You’re hacking away by yourself or with pals on something you feel strongly about. For many, your next leg is scoping out the competition and pacing yourself.

  • Should you launch with press releases on TC, NY Times, etc?
  • Should you stay in stealth?
  • Can you continue bootstrapping?
  • Do you need to hire more people to help you out?
  • Which distribution channels are the most effective? Overlooked by competitors, but you think there’s a lucky draw in it.

And then, there’s the third leg. The leg that will decide if your adoption curve forms a hockey stick or a pitcher’s mound. You have a vague idea of where you need to go, but you haven’t hit critical mass. You’re questioning your initial assumptions. You might even be questioning yourself. Did you make the right calls? Is there anything you missed? What went wrong? Should you have just taken the job your friend offered?

But if there’s anything we’ve learned from some of the best entrepreneurs out there. It’s the ones who weather the storm – the ones who have that grit – that often make it. Being able to weather that third leg doesn’t guarantee success. But not being able to weather it is close to a sure-fire for failure.

As a world…

We’re on the third leg now.

And what we do now will decide if we win or lose the race.

Photo by chuttersnap on Unsplash


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