Investing, #PropTech, and How quitting a job (or two) might be the best thing for your career: An interview with Nate Smoyer


Why do a podcast?

I started publishing Curious, this newsletter, about 6 weeks ago. 

I launched it with a few goals in mind: 

  1. I wanted to write more, and I knew that committing to a weekly schedule would help me be consistent. 

  2. I wanted to share interesting ideas and content, with a little content on why it’s interesting or why the ideas connect.

  3. I know some fascinating, inspiring people in my life and I want you to know them too.

That’s where this podcast comes in. Every once in a while I’ll record a conversation with someone I think you should know— someone with an interesting story, or an expert in a domain I find interesting. This who thing is a big experiment— let me know what you think!

Who is this guy?

My first guest is Nate Smoyer. 

In the last 10 years, Nate has led marketing and sales teams, built out an #adtech business, invested in real estate, met Mark Zuckerberg (you should ask him about it), built an ad agency, and landed PR placements at the NYSE.  

Like I mentioned before, today he’s the Director of Marketing and in his spare time he cuddles his Sheba Inu dog (Mr. Fox) and produces the Tech Nest Podcast for people interested in how technology is transforming real estate. 

But honestly, who cares about all that? Nate’s an incredible human and I count his as one of my closest friends and counselors. 

Nate’s had a wild career journey and in this conversation I ask him to walk us through the last 5 years of his life— the dude quit two great jobs, started a business, and landed his highest impact role yet. 

I hope you enjoy it. 


Detailed notes from HustleCon... AKA how to make $$$ building a brand people 😍

Here's what I learned this week about building companies that people love.

Hello there

Hi friends! Happy Friday. It’s great to be back in action after taking last week off to rest celebrate Thanksgiving.

I had a great time with my little fam… the highlight for me was cutting down a Christmas tree at a farm in the foothills of the Cascade Mountains.

Here’s what you can expect in this week’s issue of Curious:

  • Cool product I discovered

  • Raw, pretty detailed notes from my time at HustleCon (feel free to skim until you find something interesting

  • Link to a podcast where I discussed my bizarre career trajectory

Follow along!

I bought a cool razor

A few months ago I came across this podcast interview with Patrick Coddou where he talked about starting and growing a razor company. I was intrigued because I don’t know much about razors and I don’t know much about building an eccom business.

I learned that you can get a better shave and healthier skin by using a “single edge” razor.

I liked their company story and ended up checking out They had a holiday deal (pretty sure it’s still active) and so I pulled the trigger.

It came in the mail yesterday and I did my first shave.

Here’s what I liked:

  • Beautiful packaging that made me feel like I was buying a luxury good made to last

  • The razor itself felt… pretty badass. The whole handle is solid machined metal, and it felt heavy in the hand which communicates a great build quality.

  • It was easy to learn how to use it… with good tutorial videos on their site

If you hate getting nicks or are dissatisfied with cheap razors… I’d check em out!

Why and How I went to HustleCon

Several years ago, when I worked for my friend Nate Smoyer, he told me about a newsletter for growth marketers called The Hustle. It’s a daily email full of business and tech news, curated for product markers. Its founder, Sam Parr, is a sharp guy.

I think The Hustle is almost like the cool grand-daddy to Morning Brew, Money Stuff, and the countless other helpful newsletters that have launched in the last few years. I think they helped start this wave of great content and were a proof of concept for other players.

It was SUPER helpful, especially as I was starting out in tech and building my own mental framework for how to grow a company.

Flash forward a few years— last week I saw Sam share on Twitter that he had a couple of tickets to HustleCon (their big annual event) to give away to someone at random. I commented on the thread and… won two tickets!

I called up my friend Jeffrey Kranz (he runs Overthink Group) and invited him to join me. Neither of us had ever been to a tech conference like this in the Bay Area.

We didn’t really know what to expect, but we’re both always up to learn and meet interesting people.

The Lineup

The main reason why I decided to go was the lineup. It was… stacked! I was most excited to hear Michael Acton Smith (CEO of Calm) share. Calm is one of the highest grossing apps in the App Store— totally subscription based and focused on mental health/wellness.

Other notables:

  • A guy who started a deodorant business and sold it in two years for 100 million to P&G

  • One of the founders of Method soap

  • One of the executives from Hims/Hers— the health brand I’m positive you’ve seen Instagram ads for

Full lineup here:

Detailed Speaker Notes

James Reinhart, ThredUP

-Take a manual, painful process and make it easy for the customer

-They had to build out a massive infra to process the used garnest

-ThredUp build the 3 largest garment-on-hanger facilities in the world

-Their company mission is to “inspire a new generation of consumers to think second-hand first.”

-Do only the things that you’re uniquely qualified to do

-Communicate your vision until you want to vomit

Michael Atcon Smith, Calm App

Daniel Di Bartolo 🙃@danieldibartolo
They offered the owner of 5% of their non-existent company. “He wisely turned us down, we were just two blokes without a business. But it would be worth about $50 million now.” #hustleconExperience CalmRelax with Calm, a simple mindfulness meditation app that brings clarity and peace of mind into your

Alex Mather, The Athletic

-Started the company with little runway, maybe 10k in the bank

-Found success reaching out to writers/journalists on Twitter, LinkedIn sucked

-His pitch to journalists was “come here to do your best work”

-Discovered repeatable processes/a playbook they could use to scale to other cities. They looked up to Uber in this regard.

Amy Errett, Madison Reed

-15 billion dollar market for hair color. THAT IS INSANE

-I don’t have to teach people how to color their hair, they do it themselves every 6 weeks

Eric Thomas Ryan, Method

Moiz Ali, Native

I have a lot of respect for Moiz, who had ZERO CPG experience before bootstrapping Native Deodorant.

Shaan Puri, Twitch

Shaan sold his company to Twitch for ~$25 million. He was either going to shut it down… or sell it. He sold it in a process that took a couple of months.

This was definitely my favorite talk because he went into tactical detail on how he sold his company. It was a window into a world I’d never seen… he’s an engaging guy and a good speaker. He also hosts a podcast.

The mental journey you go through when selling a company:

“This is going to work”

“This will be big if it works”

I’m able to do this

I want to do this more than anything else

When you should sell:

  1. You get a great offer

  2. You don’t believe in the business anymore 

  3. You don’t want to run the business anymore

Who you should tell in what order:

  1. Yourself

  2. Your Mentors

  3. Yourself

  4. Your spouse

  5. Yourself

  6. Your co-flounder

  7. Your investor*

  8. Your team** maybe

What you need to sell: 

  1. Executive champion within the purchasing ord

  2. Company Router (someone who can help you navigate the internal structure of the acquiring company)

  3. Deal doula (friends/coaches/advisors to keep you sharp and help you close the deal)

Why they will buy you

  1. Financial reasons

  2. Strategic Reason

Why Companies Will Buy

  1. CEO finds it interesting

  2. An exec needs to demonstrate big moves, save their skin

  3. Catchup to a competitor

  4. Synergy

  5. They are afraid of you

  6. Your team has unique talent 

Engage Physically


  • Execs

  • Corp Dev

  • Investors

  • Advisors

What do you say? 

  1. Discuss partnership

  2. Considering our next steps, either funding or acquisition 

  3. Paint a picture of what the preferred future looks like... with you or without you 

GOAL is to get to an in-person meeting.

Find their Pain, then offer a cure

  • What are the priorities for the company?

  • What initiative has the most internal momentum?

  • Are there any fires to put out? Anyone on the chopping block?

  • Focus on how your specific product is a cure for their pain. Talk about nothing else.

  • Do the work for them. He went as far as to write an internal memo for the executive explaining the strategic reasons they were buying

  • Technical lead/one-pager

  • Build a talent profile of the people on your team. FIGHT FOR A GREAT DEAL FOR THEM TOO

  • Cleanup the books, get your data room ready 

  • “Turn your company into a giant BUY BUTTON”

Neglect Emotionally

Use these tools to create a competitive market

  • Find another partner

  • Go cold

  • Leave a trail of bread-crumbs… he travelled to different cities where potential acquirers were, for for their CEOs to see. Don’t know if it worked but it created the mystique 

Inspire Hope

  • We have other options, but we want you

  • Can you make it happen?

  • Time sensitive, you can steal it from your competitors

Sell Entirely

  • Due diligence

  • Closing terms

  • Get a good lawyer

  • Get a good accountant

  • Don’t burn bridges


Shaan celebrated with the friends, investors, and advisors who helped him build the company. Took them out to dinner.


  • “Birds fly, fish swim, and deals fall through”

  • Deal momentum is everything 

“You pick the price, I’ll pick the terms”

  • The terms matter more than the price in many ways

  • They HAVE to present the terms in conjunction with the price in order for you to assess it. 

Whoever has more conviction can shape the deal size for “abstract assets” like a business with low revenues but strategic value.

Did you like my notes? If so please share


I was on a podcast

I have a BIZARRE background for a product manager in tech:

👉Non-profit intern



👉 Costco cashier

👉Educator in youth prison

👉Biz dev/partnerships

👉Product Manager

👉Group product manager

I was interviewed on the Start Fast Podcast where we discussed changing careers, pitching your boss, and how to break into product management.

Listen below:


Apple Podcasts

Thanks for reading… see you next week! :)

Trying the iPad Pro for ultralight one-bag travel

On the Road

Hi there! I’m writing this from Everett, Washington’s new Paine Field… an awesome, brand new, TINY airport just north of Seattle. They only do West Coast flights, but it’s great if you need to get to Portland, LA, or San Fransisco from Seattle.

With only two gates, even without pre-check you are looking at 10 min max from car to sitting in their awesome lounge-like gate area.

Here are a couple of pics that show a little bit of what the airport is like:

Where I’m headed

My grandfather broke his hip last weekend, so this is a quick trip down to PDX to visit and wish him well. He's doing great, and learning to use his new high-tech hip. 🤖

Trying out new remote work tech

One of the benefits of my day job is that we’re remote-friendly. Most of my team is remote, either in our Phoenix office or in Texas or the UK. I’ve been able to spend time working remotely from several countries, including Hong Kong, Italy, and the UK— along with lots of work from the road here in the US.

I typically travel with my 15in MacBook Pro, a charger, and sometimes an iPad (which I use for mobile development and testing).

For this weekend, I decided to ditch my MacBook and try working from my 10.5in iPad Pro. I have the Apple keyboard/cover, Apple Pencil 2.0, and the USB-C charger.

In the last year of so, I’ve tried to go “all in” on one-bag travel.

The Principle of One-Bag travel

It's pretty simple: perpetual travel from one bag. Carry everything you need in one bag. Clothing, toiletries, and tech all go in one bag.

There's a lot of writing and content out there on this philosophy of travel, but a great place to start is Chase Reeve's YouTube channel.

In May I spent over a month on the road with everything I need in my Tortuga Outbreaker. The heaviest item in my bag was definitely my MacBook Pro.

Moving to the much lighter iPad will save me lots of weight— weight that adds up when you are in and out of planes, trains, and cabs.

So here we are— I’m giving it a go.

Here’s a pic of my working from my train ride this morning:

What I’m learning about the iPad

I’m really impressed by this thing so far. I’m been putting it through it’s paces, with a few hours of Zoom calls, plus a full day of document review, email, writing, and testing various mobile apps related to work.

Here a list of some of the apps I’ve used today:

  • Outlook

  • Zoom

  • Google Docs

  • Google Sheets

  • Safari

  • PDF Expert

  • Todoist

  • Instapaper

I think it’s important to note that none of these apps are particularly “pro”, in the sense that they don’t require lots of resource usage like RAM, GPU, or processing power.

Aside from the tiny keyboard, this feels like using a MacBook. I think this is especially so because of iPad OS, which gives you things like “full” desktop Safari, multitasking, and better file management, which has always been lacking on iOS devices.

MKBHD has a great review of iPad OS that I found really helpful:

I use the new iPad Pencil for about 5% of my tasks, mainly for annotating PDF documents and taking the occasional handwritten note.

Overall, it’s been a great experience. I’d probably buy an iPad Pro over a MacBook for my next personal PC purchase.

Unexpected Surprises

  • File Management has been really useful, especially with Google Docs integration

  • The 10.5 inch Keyboard feels better than expected, I thought it would be too small. I’d probably prefer the larger one but this is working just fine

  • I like having all of my devices on USB-C, these new iPads are all running C and that means I can just carry one cord for ultra-light travel

What I don’t like

  • There’s a bit of a steep learning curve for the new window-management gestures and multi-tasking

  • This probably sounds super dumb and petty but there is STILL NO DEFAULT CALCULATOR APP on iPad. It’s 2019. Put a calc on that thing.

  • It can be tricky to take screenshots… and I take a ton of screenshots for my job

  • This is a problem on all iOS devices but Bluetooth management is bad. You can’t manage Bluetooth devices from the control panel, you have to drill down into settings.

People are Picky

As someone who builds products for a living, I can imagine how difficult it was for Apple to get this product overwhelmingly right. They have to balance power and flexibility and ease of use, and when you pitch yourself as a “pro” product you open yourself up to the scrutiny of people like me who use their computers for a living.

I’ve only been using this for a day— I have a whole weekend ahead of me— but I’m already a huge fan.

I think people’s opinions of the iPad Pro will be largely formed on the backs of the apps they use for work. I’m lucky in that the Apps I’ve used have been great, clearly designed for the iPad form-factor and associated workflows. I’m sure YMMV, so make sure to investigate the apps you intend to use— read reviews and give them a try before you pull the trigger.

I’ll make sure to update you next week with more thoughts on this remote setup.

Thanks for reading— and have a great week!



Disney+, Swedish baths, and a guy who wants to give you a thousand bucks

Hello there

Hi friends, I hope you’ve had a great week. This week’s issue of Curious will be a little short… but you can get caught up with with the last couple of weeks here:

How Kroger gets rich delivering your avocados: a primer on the unit economics

Bill Gates, sewage, and generosity

Here’s how this week breaks down:

  1. Some thoughts and links about Disney+

  2. Some thoughts and links about Andrew Yang, a 2020 Presidential candidate who supports UBI (universal basic income)

  3. A mini-recap of our weekend in Whistler, including pics and specific suggestions for what to do.

Disney+ Launch

On November 12, the Walt Disney Company launched their much-hyped streaming service, Disney+.

Disney is a powerhouse, owning many beloved movie properties and equipped with the theme-parks, merchandising, and marketing apparatus to squeeze billions from happy consumers like me.

Disney+ had an incredible launch, doing 10 million signups in < 24hrs.

The infrastructure, planning, and coordination across the Disney org was mind-blowing, with one exec calling it

“a synergy campaign of a magnitude that is unprecedented in the history of the Walt Disney Company.”

I’d like to dive more into Disney+ in future articles, but here are a few links to get you thinking:

Disney is New to Streaming, But it's Marketing is Unmatched

10 lessons for Disney, Apple, and all the new streaming companies trying to take down Netflix

Bob Iger Takes the Gloves Off for Disney’s Streaming Debut

Andrew Yang wants to give you a thousand bucks a month

Okay, so if you spend any sort of time around me… online or in person— you know that I’m not really a *politics* guy. I don’t often share political views for a variety of reasons.

I was telling a friend recently that I fell “politically homeless”, abandoned by the extremists on the left and the right.

This same friend recommended I look into Andrew Yang, a presidential candidate.

He shared this interview with me, which I proceeded to watch in full.

Yang is an intriguing candidate to me for several reasons:

  • He is the only candidate I’ve heard talk about the coming wave of automation… that robots are literally coming for our jobs. Millions of Americans will have their job automated away… and we’ll need to adapt as a society.

  • He proposes an old idea “Universal Basic Income”, which to limited understanding, is when you tax the value that automation creates— and then distribute that money across the whole society. It creates a universal safety-net which people can choose to use on whatever they want— education, starting a business, feeding their family. I don’t know much about this subject, but this interview has me interested in learning about the nuts and bolts of this idea. His current target is $1k a month for every America citizen.

  • He’s not a reality TV star. He’s not a career politician.

  • He seems to understand the dynamics of the free market, and he doesn’t hate capitalism, which I think is essential to human flourishing.

Here’s Yang’s website if you want to learn more.

PERSONAL UPDATE: We went to Whistler

Last week I mentioned we were headed to Whistler, BC for the weekend. Whistler is a beautiful town in the Canadian Rockies, about an hour and a half north of Vancouver.

Whistler is GORGEOUS!

It also looked nothing like this photo, because there was no snow on the ground and it rained the whole weekend.

BUT, we had a great time. In last week’s issue, I shared a pro-tip. Whistler has amazing hotel deals in the fall because the Winter weather hasn’t quite hit, which keeps away the snow sports crowd. We were able to snag a deal (~$200 for the Four Seasons, normally $800+).

While $200 isn’t an objectively cheap hotel, it was an amazing deal for a high-end hotel.

It ended up being an amazing weekend away with just our little fam (me, my wife Tori, and our ‘lil boo Quincy).

Here’s a list of our favorite Whistler things.

Whistler Pics


The hotel was gorgeous. It was like a if a lodge had baby with a Restoration Hardware store.


We ate an a great Italian restaurant called Pasta Lupina.

Whistler Escape Room

There’s one escape room in Whistler, called Escape! Whistler. They have four rooms of varying difficulty. We did the pinball room and it was amazing… AND we could take the baby. Everything in escape rooms is bolted down… so automatically baby-proof.

Swedish Spa

If you did one thing in Whistler… this should be it!!! There’s a Scandanavian style spa built into the mountain…. with epic views of snow-capped peaks and the forests as far as the eye can see. Here’s what I loved:

  • No kids allowed

  • Silence enforced

  • No electronics allowed

  • Wood burning sauna, steam-room, and multiple outdoor hot springs… all to be topped off with the COLD PLUNGE POOLS.

Thanks for reading all the way to the end. It’s been so much fun— and a bit of a challenge— to write these each week. It’s been great getting some reps in, I’m trying to focus on shipping something each week that you find interesting or helpful.

It’s really motivating when I hear from you. Let me know what you like, what you don’t like, and what you want to see more of. I’ll keep writing if you keep reading!

Until next week,


How Kroger gets rich delivering your avocados: a primer on the unit economics

Grocery delivery, McDonalds real estate, and how I got a deal at the Four Seasons

Friday Night Ideas and Eggnog

Hi friends. I hope you’ve had a great week. I’m tapping away here from my home office. The baby’s sleeping, my wife (a teacher) is grading papers, and here I am writing the 2nd issue of Curious while sipping some eggnog and whiskey. Read last week’s here.

It’s a good night— and I’m excited to share some interesting things I came across this week. Here’s a quick ToC if you want to skip down

  1. Quick personal updates

  2. Does Kroger make money when they deliver your groceries?

  3. Interesting Links

Personal Updates

I’m heading to Whistler, BC this weekend for a stay at The Four Seasons.

PRO TIP: It’s shoulder season in the Vancouver/Whistler BC area. Luxury hotels slash prices before the snow comes.

That, coupled with the weak Canadian dollar, means you can score really cheap hotel stays. I’m paying $250 a night, but stays in January go for over $800 a night. I’ll share about my experience next week!

We’ve never been to Whistler before. They held the Olympics there in 2009. Send me an email with your hot tips on what to see or do.

Let’s geek out about grocery delivery

As a product manager, I’m fascinated by RETAIL. Retail is the act of selling a thing, usually referring to selling something to the person who ends up using the thing.

This is different than “wholesale”, where you are making something to sell to other businesses (who then resell to the end user). A good example of this would be when Kellogg makes a box of Lucky Charms. They send that box to a retailer who then sells it to you ( with maybe a few more middlemen in between).

Buying food is something we all have to do. Learning about the business models and infrastructure that has to exist for us to eat is a fun journey. Every trip to the store becomes a chance to peep new strategies or merchandising techniques.

When you go to the grocery store to buy food, you’re typically buying from a retailer. Since WW2, retailers have been the primary way that Americans buy food.

And Americans buy a lot of food. We spent over $600 billion on groceries in 2018.

Take our little family for example. We have 4 people in our household, and on average we spend about $150 per week on groceries.

I typically shop at Fred Meyer, a PNW grocery chain that’s wholly owned by Kroger. We moved recently to a rural area, and I don’t have as much time to shop for our weekly groceries.

Kroger provides a grocery pickup service— for $5 you can have your groceries picked by employees and delivered to your car. Pretty cool, right?

Last week, while waiting for them to bring out my groceries, I decided to do a little math because I am weird:

My tweet-storm sparked some interesting conversations with friends.

Then I got real numbers…

A few days ago, I found myself at the grocery store again. I was standing in the soup aisle when I saw him. Who was he, you ask? He was a friendly-looking twenty something employee who was picking groceries for pickup. You can spot them from a mile away because they have these big bins and special carts.

“Hey man,” I started.

“I know this is probably a little weird,” I rambled

“But can I ask you a few questions about what you do here in the grocery store? I’m super impressed by how many orders you guys seem to do. It’s an awesome service and I want to know how the sausage is made.”

I really did use the phrase “how the sausage is made”.

What followed was a treasure trove of probably proprietary info. He was super nice… and just kept talking.

I felt like a spy recruiting a deep state source in modern retail. I furiously scribbled down notes on my phone.

I now know for sure… my estimates from above were WAY off.

Here’s what I learned:

  • Average order value for their store is $150. I was waaaaaay off with my original estimate of $75.

  • The average employee can pick 7-8 orders per hour.

  • Their computer system chooses the most efficient routing for order pickup. Orders are often spread out across multiple employees and then combined in the front of the store before pickup.

  • Customers who use the grocery delivery use it a lot and tend to become repeat customers

After that soup-aisle convo, I went home to do some more research. Kroger is a publicly traded company so I was able to find info on their gross profit margin across all departments. Last quarter their margins were ~22%.

Their gross margins were MUCH higher than I originally through and so the equation has changed quite a bit. Jump down below to check out the final (rough!) numbers:

Running the final numbers

  • $150 (ARPU) x 250 (orders) is $37,500 in gross product sales per day

  • $5 (fee) x 250 (orders) is $1,250 in service fees

  • 250 (orders) would take about 3.5 FTEs over 12 hours to fill, which would cost $840 in fully loaded labor costs.

So does Kroger make money delivering my groceries?

Yes, they do!!!

This store makes $8,250 in profit from the product sales, $410 in delivery fees (less labor costs), for a grand total of $8,660 in net profit per day.

These numbers were actually much bigger than I thought!

I predict their margins will get better over time. No doubt they will use UX tricks (like Amazon) to push you to buy house brands and higher-profit items. #tricky

Why all of this matters

Grocery Stores Are Scared

Since Amazon acquired Whole Foods, there has been an explosion of activity in the grocery business. They fear Amazon, with it’s supply chain dominance, user obsession, and “everything store” ambition. Amazon is really good at delivery, and the grocery chains know it.

Almost immediately major chains started strategic partnerships with vendors like Instacart or rolled out their own grocery delivery services.

Maturing the delivery business is a hedge against Amazon.

It’s hard to make money in the grocery business. There are a few major reasons for that:

  • Consumers are price sensitive. People want to pay bottom dollar for the food they put on their table. There’s a not-small amount of people who will drive across down to save $0.50 on a gallon of milk.

  • Food goes bad. Food has a shelf life. It’s a ticking time bomb. If it goes bad before you sell it, you have to eat the cost. (Pun definitely intended)

  • Quality is hard. Grocery is a world where can have one SKU, but the quality of the product can vary massively. Take avocados for example:

If you’re like me, you’ll spend time and effort to choose the perfect avocado. Avocados that are too firm get a pass. Soft avocados get a pass. Only the perfectly ripe avocado will do for me. Imagine that kind of picky-ness, but scaled out over millions of people and hundreds of thousands of products.

Delivery or pickup is a way for retailers to hedge against their sales leaking to Amazon, and it lets them strengthen a direct relationship with the consumer (because you need to sign in with an account and credit card).

Everybody knows you win when you own the relationship to the customer.

Interesting Links

  1. McDonalds is a real estate company. I don’t eat fast food very often, but when I do I worship at the Temple of Golden Arches. I’d heard that McDonald’s makes most money through RE deals, but this Twitter thread breaks it down with real number. Tap the tweet to see the whole thread.

  1. Money Farmers: How Oligarchs and Populists Milk the EU for Millions. A remarkable investigation by the New York Times has uncovered massive abuse of a subsidy program design to help stabilize the food supply in Europe. The EU pays people to farm land. If you own land, you get paid. It’s free money. What could go wrong?

  2. Inside the Rising Costs of Making Scripted TV. Here’s a quick read on why it’s more expensive than ever to make TV.

  3. Bill Gates Speaks at the Dealbook Conference. People went NUTS this week when Bill Gates was asked about his view on taxes. Fun timing after I wrote my own piece on how the world needs more generous billionaires like Bill.

Okay friends, bye for now! Let me know what you like about these newsletters— I’m having a blast but want to make sure you like them too. 😉



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