The unconnected

Been thinking about this – connectivity and literacy.

An estimated 37 per cent of the world’s population – or 2.9 billion people – have still never used the Internet.

New data from the International Telecommunication Union (ITU), the United Nations specialized agency for information and communication technologies (ICTs), also reveal strong global growth in Internet use, with the estimated number of people who have used the Internet surging to 4.9 billion in 2021, from an estimated 4.1 billion in 2019.

From International Telecommunication Union.

Yet, “71 per cent of the world’s population aged 15-24 is using the Internet, compared with 57 per cent of all other age groups.”

Why is this so?

95 per cent of people in the world could theoretically access a 3G or 4G mobile broadband network, billions of them do not connect. Affordability of devices and services remains a major barrier. The widely accepted target for affordable broadband connectivity in developing countries sets the cost of an entry-level mobile broadband package at 2 per cent of gross national income (GNI) per capita. Yet in some of the world’s poorest nations, getting online can cost a staggering 20 per cent or more of per capita GNI. 

Read more in the ITU report.

January 31st, 2023

Reading things that massage your brain

It can be hard to replicate consistently, but being able to read things, which massage your brain – and get you thinking is invaluable.

I notice it, I’ll take a deep breath, whatever I’ve been reading has made me pause for a second. And mentally feel refreshed after reading. It’s a great feeling. But one you can forget.

This post is about not forgetting that, and a reminder to continue to seek things that you enjoy reading and stimulate you.

October 14th, 2022

Travel Activity Packs

I’d mentioned my wife puts together these great activity packs when we travel to keep our kids engaged. Whether its at a restaurant (so we have peace and quiet), in a car, or a train but mostly on planes. I’ve tried to convince her to sell them – but to no avail.

The packs get adjusted based on the mode of transport, and if we’re on a bigger trip, she’ll keep activities back, to keep them fresh and engaged with new things. And everything is washable.

On our recent trip they included things like:

  • Lego dot bracelet, that they put together on the plane. Aldi/Lego.
  • Dinosaur figurine, which they constructed and put stickers on. From FlyingTigerCopenhagen.
  • Happy Meal toys, can source from eBay.
  • Water pen books, you fill a pen with water, and they can paint in the picture. Endless re-use. Or Magic Ink books, but they’re single use. Water Wow by Melissa and Doug. Or FlyingTiger has some.
  • Scratch & reveal books. From FlyingTigerCopenhagen.
  • A small pencil case, with a mini notebook and washable crayola crayons. And usually some stickers, to go in the book.
  • A new book to read.
  • Reusable sticker books.
  • Miniature soft toys, or small plastic animals (like insects, bugs). Matchbox car. A little toy to play with, that’s also quiet.
  • Magnetic dress up like Petite Collage.

When they were smaller:

  • Something can put stuff in/out of, zip ouch, with pom poms, in/out of. Or old wallet, with coffee cards for in/out. Old milk bottle, miniature pegs and colorful rainbow erasers in/out.
  • Threading games.
  • The plane itself yields a few activities, plastic cups, the flight safety manual, sick bags, blanket or headphones.
  • Busy books.

When they’re a bit bigger:

  • Mini pots of play dough.
  • Travel magnet games, like snakes & ladders.
  • Mini pick up sticks.

Initially she used oversized travel document holders (A4 size) that had buttons to close to store these in. Then once they were bigger, a drawstring bag each, with their names sewn on. And we also put their headphones in each of their bags.

Most of these items cost $1-$5 each, so are not terribly expensive. Some of the magnet/reusable stickers can be a bit more pricey but they last for years. Dollar stores are good places to look to fill out the bag – stickers & small toys. Ebay. And then Amazon. Aldi often has little toys as well in their weekly specials if one is nearby.

The bags will also have snacks or treats in them. Something they like and something new.

October 10th, 2022

Two months travel with two under five

Are we mad? That’s exactly what I asked my wife, the night before we were to fly out to Europe. Readers know that I love to travel, I get itchy feet at about six weeks from the last trip. The compounding problem is that she’s the same! Without kids, it was much more flexible. Although we’d always be up against the paid leave limits.

But so, in 2018, we spent three weeks traveling around Europe, Germany, Sweden, Greece. And wanted to double down and do it again in 2019. But our second daughter arrived that year, then cue covid in 2020/21. Even this year, when planning through winter, it was kind of uncertain if this year could be the year.

I thought I’d share more of the – how did we actually do that. And maybe some trip highlights in another post. Yes we probably are a bit crazy. Hopefully you find it helpful for your own travels and maybe consider traveling with your kids more!

Initially we started out with a view of getting a place (i.e. house), or two places, and doing lots of little trips from there. This sounded good, but we felt like we’d be coming/going too much. Also, it was harder to find a place. Because if you have a good place to rent, why rent it for a month, when you can rent it for a week and charge a bit more. The ole slice it up and sell it for more trick. Or the other factor, if you were the type of person to go for a month, if it’s a good place, you would book it for the next year, to lock it in. Finally, all the travel from post covid was swamping supply.

When we left, we still had over half of it unbooked, but an uncanny thing is that you would see AirBNB supply adjust to suit, with new listings coming online. Either people themselves going away for a month and renting their place, or completely new listings.

But I’ve skipped ahead a little, so how did we plan this? We started off, over a drink and nibbles, just jotting down all the places we wanted to go. Nothing off the table, just places we’ve always wanted to go. That gave us a list to work from.

Then we would research and plan itineraries for each place, how do we get there. What’s going to be our best entry point from New York. We also wanted to minimize flying/trains for covid reasons (this turned out to be prescient, as we saw all the flight delays over summer and lost luggage). However in the end we did use trains. And ended up with a disjointed flight, New York to London and return via Milan. Often airlines will give you the same rate for this, as they would return from one destination. So am a big fan of this approach.

This let us plan accordingly. We wanted to visit friends and then have us time to explore. A couple of times, we spent too much time, trying to work in with friends, when we should have just kept it shorter, and whilst maybe not enough, have made full use of the time. i.e. come in for 2-3 nights, have a blast, then keep going.

A key part of our itinerary, meant using rental cars. Which is where prices were mental too. So what we did, is opt to look at local car sharing services, like a Turo. Through this, we found Share Now and Virtuo. Both offer cars for driving around the city but they also let you drive out of the city. And in Share Nows case, if you pay an extra fee, to other countries. And given with two kids, we can’t get the smallest car available, this meant these services were cheaper than a rental.

However, they were not without trade offs. Virtuo was especially nice, they drop a car off near you, you pick it up and go. Have to fill it up, and return, and notify that you’ve done that. They have a slight surcharge for miles, but it was reasonable. We got a little Mercedes A-Class, it was tight with luggage but did the trick and perfect for getting through the smaller lanes across the UK.

Share Now, you can pre-book the car, and then go pick it up. Share Now is primarily used in cities, to get around, or quick trips out. This means that they’re not always clean. A couple of times I had to reject a booking once got there because it was dirty. This introduces some uncertainty, where it may take a couple of tries to get a car. Which then means planning this into your itinerary. However that timeframe was usually still less than you spend at the car rental desk.

Both use an app to open the car. Virtuo, I believe has a key, but Share Now often didn’t. Which did mean, when the car wouldn’t unlock via app, we couldn’t unlock the car at all. Which ended in tears in France. More on that later.

But these were both great options, there was another option Hiyacar we considered in the UK, but it wasn’t available to tourists. Note, for Share Now, you had to sign up, pre authenticate with a license. Then send in your entry visa on landing, as they can only offer it for first 6 months of entry for tourists.

Time wise, we had thought three months, but that was with the idea of getting a place as a home base. With that not working out, and also, sandwiched by when our daughter would start school. We ended up at 2 months. It’s kind of nice, the US School Summer holiday is longer than NZ. And timing wise, it meant we started our trip before others had finished school, and then at the end, kids were back at school. So we got some quiet periods of travel.

Traveling with two kids, and also me doing some work late afternoon to evening, we planned our days like this. We would jump up, have breakfast in, or have something lite and have a bigger morning tea. And get to what we wanted to do for the day early, meaning we could be back by late morning/early afternoon. This meant we mostly avoided crowds, the heat wave was less of an issue and it gave the kids (and us) built in downtime each day. It actually was a brilliant way to travel. Sure sometimes we broke the schedule and did a couple of days all out, but this as a repetition worked well. We also tried to do more popular things during the week, and chill out in weekends.

To keep them entertained, we did take some toys, and at destinations (which we forewarned them on) we’ll get some more toys. Like the beach, or Munich. And they could add to it. This paired well with, we took gifts for friends, and as we unloaded those, we replaced with those! We didn’t do lots of shopping on things to take back, but did top up on clothes at various spots. Or nabbed some European brands we liked. Flying Tiger Copenhagen is ideal for activities and only a couple of euros each, if you can try stop at one on the way. Unfortunately through covid the New York ones closed down.

My wife is also the master of activity packs, they each had a little bag, filled with little activities, they could do on the plane, or in restaurants, so we could have some peace and quiet. This could be coloring books, stickers, little toys, scratch and reveal. This also meant no screen time activities.

In terms of screen time, we would save a few shows/movies offline so they could watch those. AudioBooks, Spotify Kids if you fav a book, it saves it offline. As well as Duolingo Kids, Duolingo itself (doing it with us) to practice the local language. And Khan Academy Kids.

We use Google Fi, which worked in most places, but occasionally you need to run off ‘automatic network’ detection and manually swap to another. In Italy, it would sometimes not connect, so we had to reset a few times, so the sim would register on the network. Otherwise it worked well.

On luggage, we did need to keep it light. We wanted it, so between us we could carry everything, for at least 500m, which was a good plan in the end. We swapped out our regular car seats, for lighter/travel ones. We have a Cybex travel pram. We stayed at places which could give us a travel crib. We used travel pods, just Amazon Basics ones, which worked brilliantly for packing, as we had a pod each type thing. Made it so so much easier. I even went – how can we take less charging cables etc, and ended up swapping for a Anker MacBook charger and they have a European adapter, with two USB plugs on it. And then one Apple iPhone USB charger, but we have the travel adapter kit. This combo covered us, for white noise machine, charging. And saved space/weight.

My personal list, was like two pairs of shorts, togs, jandals, three t shirts. Pair of sneakers. One sweater. Two pairs of pants (should have only taken one). Socks. Boxers. Three summer shirts (could have taken two). Hat. Running shoes, exercise bands, running singlet/shorts/boxers. I also never wore my sweater except for the flight!

It’s hard, as you sometimes need to look nice/smart casual for restaurants/activities. But then you need to be able to go up Garmisch with the kids. This combo worked well.

Our itinerary, took us through the UK first, with the first 3 days in London – specifically for jet lag recovery. For those without kids, they recover before you actually can. Which is why we planned it that way. And it worked well.

Basically we flew into London. Rented a car and drove about. Then flew to Milan, and used car/train to get around Germany/Hungary/Austria/Italy and France. A few mechanics here, I once took a train to Munich, to pick up a car and bring it back – as cross country drop off wasn’t going to work. So we had to build flex into the plan.

Currency wise, most things were in Euros. We use Wise (ex TransferWise), they have a travel debit card, which means you can pay all transactions in local currency. And they either convert it on the backend, or you can have loaded currency prior. And that’s what I did for the six months leading up to it, each week I’d buy some currency, just a little, but it was a nice build up, to think about the trip each time I did that. And it also meant we got a good price on the currency. You can also withdraw local cash, up to $150 free, then a small charge after that. We used this for most local purchases. Super handy.

Where did we do our planning? It would always be a mix, see if we can get some Monocle travel video for the town, TripAdvisor, just Google. And also, would follow a subreddit for the place for a few months, to see what common questions are – and the recommendations.

We do know, in each place, our kids want to see animals! My wife likes stationery shops. And I like a good cafe/restaurant – and if I can find a place to run. So we’d try work that in, so each of us was getting some of the things we know we enjoy.

Where we stayed, we leaned into AirBNBs, because they tend to have more family friendly accommodation around Europe. Hotels are good, but often small, or we’re all in one room. Whereas for the same price, we could get a couple of bedrooms, washing machine, and stay in a neighborhood. But we would mix it up and treat ourselves. For example staying in a hotel in Florence, with a rooftop pool.

AirBNBs don’t always work, but reviews help ease that, some places had like 500 reviews, which is nuts. But usually meant a smooth operation. Others we were some of the first guests, so you know they’re working out the kinks but that’s usually offset with a better price. So some give and take. Hotel Tonight was good for finding spots but the rates (at least more most of this trip) were as good as booking direct.

Gadgets -> we didn’t have a lot. iPad mini, kindles (for us to read on) and GoPro. The latter I am a big fan of, as you get nice footage and helps bring the family back to that moment in time. Also their GoPro Quik app, means you can quickly make little videos to share. Also a shout out to Apple Memories in Photos, this is so good and is getting better over time.

We like to use Google Photos to put together photo books (now that Apple doesn’t have it built in). But are finding this more cumbersome when you have lots of photos. So if anyone has tips – let us know!

Travel insurance isn’t used as much by US travelers we’ve noticed but kiwis definitely do. So yeah we got that again for this trip, it usually costs a few percent of your coverage. If needed, RentalCover is a good alternative to the rental car insurance, which we’d use where the economics made sense. We didn’t end up making claims for this trip – but a prior earlier this year – we have noticed delays in processing them.

That does bring me to, our car broke down in the South of France. Which I’m ambivalent about, if you travel enough, a car has to bread down somewhere – and as far as I can recall we’ve not had a break down on any trip. However, with two kids, it does complicate things. The car basically bricked itself, like an iPhone, we couldn’t unlock it with the digital key on our phones, and the rental car company couldn’t do remote unlock. So we had to get it towed, then make our own way back. Which was pretty challenging, last minute, with many of the trains around France booked out in a holiday weekend. But we figured it out and as a bonus got to see Nice. Our AirBNB host was very gracious and even gave us a ride to the next town, when taxis weren’t available – thank you.

Eating wise, we leaned into more eating dinner at home as a default, with planned special evenings here and there. And we’d eat out at lunch/morning tea. This worked well, food in Europe is quite cheap (and delicious). And it was kind of nice some days to know, oh we’re not going out again, so can recharge the batteries.

Fitness, I know people have a mixed bag on this. And I respect either way, when traveling its hard to keep up routines, the days can be long/physically draining anyway. But so, I tried to run in each place we stayed, see my post on the Foreign Run, am a big fan of this. And I keep them to 5km, so its not like I can’t do that and still have a busy day. And then I took exercise bands, and used those with a few different exercises, either where we stayed or at a park nearby. Usually trying to sneak out first thing in the morning, or in the afternoon when we were staying put.

I didn’t do anything before the trip to prepare but a few months before someone on Twitter had said to incorporate carryalls into my workouts, which I did, ironically two 20kg kettlebells. One day as we humped the luggage through an airport, I realized that was the perfect weight for this actual scenario ha. Also, with kids, you are going to carry them more, with more steps, they’re tired etc.

For keeping track of the itinerary and all the bookings etc, we use Evernote. With a shared notebook, so we have redundancy, and have synced that offline on both our phones. So we have cloud, and a version each. For each city, we would make an Evernote, then jot down the things we wanted to do, and then if we had any bookings. This worked well. And its something we’ve done for years anyway.

How do you rationalise all this? It’s a bit mental. And with young kids, its easy to go, there are other things that are easier. But they are only this age once, and we don’t know what the future holds, if we can do it now, why not know. I’ve never regretted any travel I’ve done. And it is a heck of a lot of fun, the payoff is worth it. When thinking about it, starting with your dream destinations, and then they things you want to do in each place, helps too. As you’re like, wow I’ve always wanted to do this. The alternative was another summer in the city with trips upstate/around. Which is idyllic, but an adventure like this every now and again is healthy. For us it was also very cathartic, to get out of the city for a sustained period of time, to try lots of new things. And to return mentally fresh – to tackle the new challenges.

I think that’s it for this post, so that’s some of the how, I’ll share more of the highlights in another post. It was a phenomenal trip. And so good for the whole family, to each have their own experiences, to meet new people, try new things and just work together through things. Not easy at times but I’d do it again in a heartbeat.

October 6th, 2022

Public Water

In line for the Medici art gallery, Capelle Medicee, Florence, Italy, there was a public tap, and I thought surely you can’t drink from that. But in the heat, a couple of people went up, filled their water bottles,  and it turns out, sure enough they do. In fact they have to be drinking level quality.

Later that day, I discovered that in the Piazza della Signoria, not only is there more water on tap. But sparkling water! Now that is civilization. 

The public water service is provided by the local water provider in Florence, Publicaqua. Whom are held to quality standards set by legislation. 

There are 61 parameters, divided into the following categories: microbiology, chemical, indicators and accessories; the quality of the water distributed by Publiacqua continuously and fully satisfies the requirements set forth by the law.

What a wonderful public good, and in the heat wave of this summer, a necessity. I wish more cities did this.

September 27th, 2022

The Foreign Run

Colin recently put together, the Foreign Morning Run. Something I am a big fan of.

When traveling, I like to plan a run whilst I’m there, it does help with jet lag – but it’s also nice to just get out, to see where you’re staying, before everyones up. You come back feeling great and can start your day.

We spent two months over summer traveling and a few of the highlighted runs were, running through nature in Tuscany, up over a small hill in the Peak District, quiet Milan streets, getting lost in the Englisch Garden in Munich, the sweltering heat of Florence and taking a wrong turn in Provence.

No photos unfortunately, I should really start taking my phone.

You can run where you’re going to visit that day to scope it out, for a view of the city, or round a park. Often I see things that we may go and do later, or find that cafe near where we’re staying, or just get a feel for a place. Seeing the square before everything open. Oh and it has the added benefit of keeping you fit, coming back ready to start the day.

Getting lost is particularly good because then you need to find your way back. This is how I ended up doing a couple of circuits of the Englisch Garden in Munich. One run in Cologne, I’d got some local tips and they estimated the run at 5km, as I got half way through it, it was more like 12km. But still enjoyable.

I’ve started feeling like you can’t get to know a place till you’ve done a run, to see it, as it is. Not through the sheen of tourist sites, language barriers, a plan set for the day.

Of course they don’t always happen, you oversleep, the kids are awake early or you just run out of time. That’s all good too, there’s always next time.

September 13th, 2022

Unplanned routes

I’ve been exploring with the family through Europe this summer. Mix of work and play.

But one thing we’ve done, is to have unplanned blocks of time. Which is, where if there’s something we want to do, or change our minds, or want to revisit. We have the time to do that.

It’s neat, and allowed us to revisit some places we really liked. Or to adjust the plan and do more of beach time.

A bit daunting not having it all planned upfront – but you figure it out. And that’s part of the fun, what’s good, where can we go. Oh maybe we do this now instead.

August 4th, 2022

Andy Jassy’s first letter as CEO of Amazon

It is a tremendous read. Very Bezos. Very Buffett too. Here’s a few highlights,

On innovation:

One of the lesser known facts about innovative companies like Amazon is that they are relentlessly debating, re-defining, tinkering, iterating, and experimenting to take the seed of a big idea and make it into something that resonates with customers and meaningfully changes their customer experience over a long period of time.

On building products:

1/ Hire the Right Builders: We disproportionately index in hiring builders. We think of builders as people who like to invent, who look at customer experiences, dissect what doesn’t work well about them, and seek to reinvent them. We want people who keep asking why can’t it be done? We want people who like to experiment and tinker, and who realize launch is the starting line, not the finish line.

2/ Organize Builders into Teams That Are as Separable and Autonomous as Possible: It’s hard for teams to be deep in what customers care about in multiple areas. It’s also hard to spend enough time on the new initiatives when there’s resource contention with the more mature businesses; the surer bets usually win out. Single-threaded teams will know their customers’ needs better, spend all their waking work hours inventing for them, and develop context and tempo to keep iterating quickly.

3/ Give Teams the Right Tools and Permission to Move Fast: Speed is not pre-ordained. It’s a leadership choice. It has trade-offs, but you can’t wake up one day and start moving fast. It requires having the right tools to experiment and build fast (a major part of why we started AWS), allowing teams to make two-way door decisions themselves, and setting an expectation that speed matters. And, it does. Speed is disproportionally important to every business at every stage of its evolution. Those that move slower than their competitive peers fall away over time.

4/ You Need Blind Faith, But No False Hope: This is a lyric from one of my favorite Foo Fighters songs (“Congregation”). When you invent, you come up with new ideas that people will reject because they haven’t been done before (that’s where the blind faith comes in), but it’s also important to step back and make sure you have a viable plan that’ll resonate with customers (avoid false hope). We’re lucky that we have builders who challenge each other, feedback loops that give us access to customer feedback, and a product development process of working backwards from the customer where having to write a Press Release (to flesh out the customer benefits) and a Frequently Asked Questions document (to detail how we’d build it) helps us have blind faith without false hope (at least usually).

5/ Define a Minimum Loveable Product (MLP), and Be Willing to Iterate Fast: Figuring out where to draw the line for launch is one of the most difficult decisions teams must make. Often, teams wait too long, and insist on too many bells and whistles, before launching. And, they miss the first mover advantage or opportunity to build mindshare in fast-moving market segments before well-executing peers get too far ahead. The launch product must be good enough that you believe it’ll be loved from the get-go (why we call it a “Minimum Loveable Product” vs. a “Minimum Viable Product”), but in newer market segments, teams are often better off getting this MLP to customers and iterating quickly thereafter.

6/ Adopt a Long-term Orientation: We’re sometimes criticized at Amazon for not shutting much down. It’s true that we have a longer tolerance for our investments than most companies. But, we know that transformational invention takes multiple years, and if you’re making big bets that you believe could substantially change customer experience (and your company), you have to be in it for the long-haul or you’ll give up too quickly.

7/ Brace Yourself for Failure: If you invent a lot, you will fail more often than you wish. Nobody likes this part, but it comes with the territory. When it’s clear that we’ve launched something that won’t work, we make sure we’ve learned from what didn’t go well, and secure great landing places for team members who delivered well—or your best people will hesitate to work on new initiatives.

April 15th, 2022

It’s time to upskill

New year, new you, right? Well it is a fresh start, to lay a foundation for a big step up in the year ahead. And a couple of thoughts I wanted to share were around upskilling and data.

We are now seeing the culmination of covids acceleration in the evolution of the internet. And that has brought a lot of new lingo, new tools and culture. But so many of us are having a challenge catching up on this new world. We do have two choices, to get in there and learn, or to sit this one out.

That means its time to upskill, to tinker with these new tools, to spend a few hours just trying to make something work. To find time in the calendar, not for anything specific other than to play and learn.

The year also brings a fresh start on data, what data are you using as feedback? Daily, weekly, monthly? Data nudges you along on any journey. And now don’t be so limiting to think all data is a dashboard, data can be a journal or log you keep of activity, it can be your Apple watch, it can be actual measurement. Data comes in many forms.

The power of data is often in that it just exists, it acts as a feedback loop, which keeps focus on what you’re trying to achieve. And that itself, without the substance of what the data is telling you, is very valuable.

So as you think about the year ahead, think on upskilling and what data can nudge you on the things you want to achieve.

January 7th, 2022

Exercise bands and distillation

I’ve been enjoying exercise bands, $20 from Amazon. They’re the ones with grips and depending where you are there’s a million knock offs.

Initially the bands were to to round out others I was doing outside. But now that I am able to go back to the gym, I’ve made them part of my gym protocol. For biceps, chest, back.

(If you grab them, they come with a manual showing a bunch of exercises to try).

And I really like this as an analogy, the bands were made to help distill a gym workout in to something that was portable. And then reversing that, it has a great role in a gym based workout.

It’s like adding chicken stock to a chicken soup. The distillation, re-added to what was aiming to distill improves the end product. Funny thought but kind of makes sense.

December 1st, 2021


There is an immense satisfaction in tinkering. Just playing about, exploring, seeing what something does.

It’s being curious without an agenda.

The same as pursuing boredom is a worthy goal, so is tinkering. Treat this post as permission to tinker, I sure am.

September 15th, 2021

Late stage secondaries

This is the third in my recent posts about investing (100 Companies, Investment lens, what I’ve been up to). More about the discoveries I’ve made the past 18 months or so. This post is on secondaries, that is buying shares in later stage startups. This is an area that has been getting more and more democratized. Examples might be a SpaceX or a Stripe.

The present market state, is such, that for institutional investors who want exposure to future IPO companies there are a lot of options. For individual investors the options drop off compared to that but are still available.

Who can do this?

Typically the minimum is $50k, however some platforms come down to $10k depending on the deal. So these are sizable investments. Which hold a lot of risk, an IPO or acquisition isn’t certain. However you can buy in to quality companies that you want to own.

You also need to be a qualified individual under US law.

How are they structured?

Typically the firm creates a SPV to hold the secondary shares and you are buying units in that entity. You can hold the units directly or you can hold through your own entity.

Can you buy a ‘fund’ of secondaries?

Yes, most providers either offer these in batches over time or continual funds.

Where do they get the shares from? Why are those people selling?

Typically these are early employees selling their shares, it can also be funds from early investors selling a portion of their stock. You might think they’re crazy to sell stock in such a hot company. But these holdings might represent most of their gains or all of their net worth. A smart individual would sell some, to at least pay off the mortgage, diversify.

The other thing is, life happens. The employees may have left or are leaving. Tax bills arise.

But you are right to be skeptical, maybe they are selling as bad things are on the horizon. Be attentive if you’re seeing a lot of sales or a depressed price. That is where your own due diligence needs to come in, a long term outlook and to listen to the market.

The final way is some firms offer financing for startup employees to exercise their option or to buy their options if they are leaving. If they finance the exercising of the options, they typically take some upside. So in each case they are on-selling their asset.

Right now, you also have to question why aren’t they going public now? Typically they have access to capital and a good plan to keep growing in the private markets. Or they have more work to do to get the business ready.

Information issues, rights & lock ups

Because these are secondaries, you are going to get imperfect information. Prior financing may have additional warrants or the total amount of issued shares may be inaccurate. Typically they are close but don’t go in to this expecting to lift the kimono and see everything.

The next thing is rights, you likely will not get information rights to receive updates from the company. And also will not get a vote etc. You just get the exposure to the upside.

As these are employee shares, you will likely be held to the same employee lock ups. Meaning you may have public stock for 3 or 6 months. Further for tax compliance, you will receive K1s each year.

How do the firms offering these make money?

The firm offering it will charge a placement fee and take some carry. Carry will be calculated on the IPO price, or an average of the last 30 days of trading if a lock up period is in place. There may be a management fee as well to maintain the entity and compliance.

Imperfect pricing

To set expectations, because this is a secondary and limited supply available, you are typically going to get imperfect pricing. You may be buying at a discount, or a premium to the last round.


  • Be fast, hot companies can get allocated very rapidly. As fast as 8 minutes I’ve found.
  • Friday, I tend to see the offerings coming on a Friday. I’m not sure why, my guess is that they’ve spent all week finalizing the details and now need to get it out.
  • Complete your KYC details early. KYC is know your customer and requires validation of who you are, or your entity, and your role in acting on its behalf.
  • Insidery, hot companies are going to go fast so often *may* be provided to their top or most frequent investors first. I haven’t seen this as a strict policy but observed it happening. So do put the highest allocation you could make when you indicate interest and let your account manager know your interest or flexibility.

Who are some of the firms that offer these?

  • MicroVentures, from my observation they appear to have the best deal flow for ‘retail’ like investors. They provide companies, small funds with a collection of companies.
  • Forge, they merged with SharesPost to offer a broader array. They also have a good volume of deals.
  • EquityZen, a generalization but they tend to have more media/NY offerings. Lower minimums.
  • EquityBee, is similar to EquityZen, they also tend to have a mix of different types of companies. Lower minimums too.

Those are the main ones. The Forge founders are also working on a new company, which may yield new options in the future.

Here are some offerings that *may* in the future offer more options for retail but offer options for those with larger commitments:

CartaX is more for institutional right now, but may have more retail like options in the future.

SecondMarket, acquired by Nasdaq also is on the same path. Providing offerings in private companies.

SecFi, they fund employee options and take a portion of the upside, and will sell some of that exposure.

GSquared, they also offer options for family funds.

What about Crypto?

There have been coins been sold against soon to be public companies, like Coinbase & RobinHood. The coin represents, converting the initial capital at the first day of trading. So this gives you synthetic exposure without underlying stock ownership. This is a space I would expect more to happen over time.

August 28th, 2021

The challenge across investment classes

I missed out on investing in Instacart, relatively early on. A buddy of mine did not. Another buddy also passed. If you fast forward to today, Instacart (even prior to covid) was valued at $7.9b and now $39b in the last round. That is an insane multiple.

So what went wrong?

At the time, when I saw it, I liked the idea and the convenience. Very early the proposition was about getting a red bull or a couple of items to you fast. Then in New York it enabled delivery at supermarkets which was less common at the time. We even used the service a bit.

What I didn’t like, is I couldn’t see a long term sustainable business model. The discounted delivery fee wouldn’t pass on, consumers wouldn’t pay for an increased margin on products.

The knowledge, that yes they could improve the operation as they scaled, they could find new ways of generating revenue (like advertising) and their team could execute brilliantly – was in the back of my mind. However, not enough to press go.

In evaluating I was thinking like a value investor, not a growth investor. It was clear from a growth perspective they could grow significantly and ideally solve some of the challenges with scale. A growth investor would have gone yup lets do it.

That’s not to pass judgement on my investment lens. It’s just for that investment, at that time, with the type of capital it was the wrong one.

It’s also a lens that has limited my opportunities with Crypto, I’ve mostly struggled with seeing the big picture and where the real tangible value would be created, or created through exchange.

And for me personally, I invest resources through Nudge, board positions, early stage investment, late stage and then income, retirement and a fun account. This is a primary function, resource allocator.

Swapping investment lens in each scenario has taken some work, to sit and define how I should be thinking about investment allocation in each scenario. What is the most appropriate way to evaluate each of these. But a fruitful exercise. It’d be insane to take a crypto investment lens and apply that to retirement investing. The defining of that has been immensely helpful, to hone my own thinking and to help in swapping context.

The mental short cut is to entrust your funds to experts who will make those judgements. Find an expert in Crypto investment, evaluate them, their lens, knowledge of the space. And back them. That’s why index funds are so valuable to investors, for the same reason. You can always change at a later date when or if you want to get more involved.

Extrapolating that out to other areas, it’s the same as hiring a personal trainer, rather than figuring everything out, get someone who knows the road and makes the calls based on your own results or progress.

August 26th, 2021

100 Companies

One of my emergent post-covid goals is to invest in 100 companies over the next three years. The key aim is to learn, to have fun and a bit of adventure. And of course make some money along the way.

Now the problem with that sort of number of companies (and ambition) is that that is a monumental undertaking. I don’t have the capacity to find, sort, filter and do that many deals. However the way I am addressing it, is by finding a few funds or syndicates, that enable me to do that.

The first is FundersClub, FundersClub shares direct investments and fund investments throughout the year. Of note is they do a Y Combinator round each year, going in to a selection of Y Combinator companies.

The second is, Angel Syndicates, finding a few managers who I think will sniff out great deals. You join their syndicate and those deals are shared with you. You can either back every deal they do or back individual deals as they come through.

The third will be a mix of private direct deals, either sourced by myself or from my networks. I haven’t used either Assure or RUV yet for structuring a deal. The former lets you put together a SPV for a direct deal, RUV also offers the same sort of service. Letting you and a few friends invest together.

Separately, I will continue to explore the secondary markets, follow on into prior investments. The secondary space has a bunch of innovation. Maybe I’ll do a follow up post on that and the opportunities it presents.

The benefit of the approach above is, low cognitive load but also gets me in to companies I might not have because of my own selection bias, with this approach I tap in to a bunch of different thinkers who would tackle opportunities I wouldn’t take a second look at.

For me a big driver of this is learning, taking a small stake typically means there is no real engagement with the firms but you do get access to updates. However some of the private deals will mean more involvement. But so, by getting such an expanse of companies and an understanding of where they’re investing, challenges they’re facing, seeing the public view vs behind the scenes view and how their journey evolves. That is a bunch of learning!

As we navigate the emergent economy, what better way than to get a broad view from a bunch of companies.

August 3rd, 2021

A lot of good business ideas come down to

The ability for the end user to identify new capital opportunities or to reallocate capital efficiently.

Whether it is adjusting their own purchasing, disrupting current spending from old to new, or justifying new investment. It’s when those dollars start trading hands and moving that the market really starting paying attention.

July 22nd, 2021

What are you doing all the way down here? You could:
- View my about page
- Or for first timers the New Here? page
- Or maybe email this to a friend
- Or subscribe to get blog updates