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  • Jason Calacanis 21:25:52 on 2021-03-23 Permalink

    Kevin Rose on his product philosophy, Reddit & Digg’s inverse journeys & Twitter’s recent product innovations | E1185 

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    Top Insights

    • Products must begin with only 2-3 key features. Once there is traction, you can prioritize what features to build next by asking users for feedback.
    • Fewer features allow you to launch quicker, at a lower cost, and actually determine if there is product-market fit.
    • Replacing a founder with “professional management” to commercialize a business often kills the product and company culture. (See Tobi’s Rule EP 1184)
    • Twitter’s new product roadmap offers an antidote to the chaos of text-based social media, a natural extension that compliments their core product.
    • NFT & blockchain technologies will revolutionize the ways we manage rights & ownership, despite most projects in the space likely being worthless.


    • Kevin Rose is a partner at True Ventures, a consumer-focused venture firm with early bets on Peloton, Fitbit, Blue Bottle, Ring and more. He hosts the “Kevin Rose Show” Previously, he founded the social news site Digg, the intermittent fasting app ZERO, and the meditation app OAK.
    • His most notable investment include: Twitter, Facebook, Zynga, Square, Medium, Foursquare, Nextdoor, Blue Bottle Coffee, Clever, Ripple, Oura.
    • Kevin’s past This Week in Startups appearances:

    Experience as a founder vs. investor

    “Nothing beats the rush when you launch a new product. The ultimate peak as a founder is to have people using something that you created.”

    Kevin Rose
    • Some downsides of being a founder include managing people, making hard initial engineering hires, fighting for talent, and having difficulty sleeping.
    • Kevin prefers building a product in the early stages over trying to scale a growth-stage startup.
    • A common mistake founders make is not asking for help when they don’t understand how to do something. Great founders seek out mentors and soak up information like a sponge.
      • For instance, when Mark Zuckerberg visited Digg in the early days of Facebook, Kevin was surprised at how unafraid Zuck was to ask questions and be vulnerable.
    • Investing is fun because you get to identify companies early on and try to imagine how it could become a multi-billion dollar business (and sometimes that happens!).
    • There will always been a randomness in investing:

    “Some investments, I really did a good job getting the deal done. I tracked down Jack [Dorsey], I had him on my podcast, I convinced him to be an Angel in Square. But the crazy thing is that I’ve had cryptocurrency investments outpace that return, just because somebody asked ‘hey, do you want to throw in some cash on this crazy new up-and-coming project?’ and I put a little bit of money in and it returned a boatload.”

    Kevin Rose

    Product philosophy

    “Pound for pound as product person [Kevin is] part of an elite top 10 alongside Elon, Steve Jobs, and Alex from Calm. When [Kevin] makes a product it just comes out great.”

    • Creative people are filled with ideas, but you need discipline to boil it down to the simplest version of your product vision.
      • Pick only two or three things that absolutely must exist and do them really well.
    • Building fewer features shortens the development timeline down to just a couple of months versus 6-8 months.

    Case study on Kevin building Zero Fasting

    • Problem: Kevin read promising research on intermittent fasting from Dr. Valter Longo at USC. There were human placebo, double-blinded, “gold standard” studies showing autophagy, improved glucose levels, and reduced chemotherapy side effects. In short, fasting was helping people live longer with less disease.
    • Market Research: There was nothing on the App Store dedicated to fasting. Using your phone’s timer was inadequate because it didn’t track historical fasting data.
    • The essential features: Timer + Calendar. Allowing for historical performance, average fast duration, streaks, etc.
    • Kevin’s subtle fingerprint on Zero: Showing the live number of simultaneous fasters on the platform in order to create a feeling of community, due to the difficulty of fasting – especially in the early stages. “570,345 people are fasting with Zero”
    The Zero app, note the “active faster” count at the top
    • Essentialism creates a clear user value proposition & lets you bring it to market quickly.
    • Once you have traction, there is an opportunity to add the other features you wanted to build. More importantly, your community is going to start telling you what they want.
    • Digg would survey 1 in 100 users, asking them to stack-rank the list of features the Digg team wanted to add. By combining the team’s product insight with the input from users, the community was engaged and excited.
    • Kevin invented the “Like” Button on Digg (called “diggs”).
    • Don’t get high on your own supply as a product person. Keep trying and keep iterating.

    “If you try and fail as many times as I can, you will get some home runs from just the sheer number of times you’ve had the at-bat.”

    Kevin Rose

    Lessons from Digg & Mahalo

    • Jason saw Digg early in 2004 and was impressed with how quickly it became a top source of traffic for his company Weblogs, Inc
      • Jason got a verbal OK from Weblogs investor Mark Cuban to try to buy Digg for $1M.
    • Jason’s idea for Mahalo was 10 years too soon: “I knew that search would change from 10 blue links to what it is now. I even came up with that name, ‘comprehensive search.’ What if the images and the video and content were mixed with the search results? -Jason
    • Branding Mahalo: Jason considered which companies and products had the most beautiful logos. Thunderbird and Firefox came to mind, so Jason tracked down the designer Jon Hicks.
    Mozilla Firefox & Thunderbird Logo
    Mozilla Firefox & Thunderbird logos
    • There was a 6-month wait due to the demand for Jon’s design genius, so Jason made a series of aggressive offers to jump to the front of the line. Jon’s Mahalo logo was an instant hit amongst “product-people” like Kevin Rose.
    Mahalo Logo
    • Beware of relying on one source of organic traffic: Mahalo was making thousands of dollars per day from ad revenue. But when Google released the Panda update for search, 90% of Mahalo’s traffic went away overnight. Even with influential connections at Google, Jason was told search was a “black box” and nobody was able to help.
    • Professional management” can destroy a product and the culture around it: Digg’s 3.0 redesign made it more commercial, prioritizing publishers instead of the content the community loved. The goal was to become a bigger business, but it destroyed the core product value and eventually led to Kevin’s departure.

    Twitter Spaces and Clubhouse

    • Not needing to download a new app reduces friction and it’s easy to get “40 blue checkmarks in a room” on Twitter, since influential people are already there.
    • Twitter has been slow to add features or change the core product, which they have been lambasted for by power users. However, it’s also a secret sauce to success. Reddit is in a similar boat with their product history.
    • Twitter Spaces is a natural extension the platform. Audio has the power to create a meaningful dialogue to offset the “dunking” and tensions created from the current lack of tone/context on Twitter.
    • Social media founders didn’t set out to create chaos online, and these new features can help realize an idealistic vision of an at-scale social product. “I think that you’ll use text until you feel misunderstood or the conversation devolves significantly and someone says ‘you guys should talk it out in a Twitter Space.'” -Jason

    NFT & blockchain technologies hold promise & potential pitfalls

    “I’ve been tracking NFTs for a long time. I believe there’s going to be a lot of garbage in the space when every artist with Photoshop can become an ‘NFT Master’. But there’s a lot of really credible projects reimagining rights, distribution and ownership.”

    Kevin Rose
    • Tokenized ownership can allow the creator of an object to receive a portion of the proceeds every time the asset changes hands.
    • Some potential revolutionary use cases:
      • Unisocks has dynamically priced socks where the token can be exchanged for the physical product (it’s silly because these are socks but imagine them as Yeezy’s or other high-end collectibles). This allows for price speculation on objects without needing to hold physical inventory.
      • Backing early musicians, where the the owner of the token is entitled to residual music royalties.
      • Media licensing on the blockchain, where every artist/creator can set the price to license their creation.
  • jacquideegan 22:24:09 on 2021-03-18 Permalink

    Lessons from Shopify CEO Tobi Lütke: what he learned from scaling Shopify through the pandemic | This Week in Startups Blog 

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    Click to Tweet about the show

    Watch / Listen to the full episode:

    Top Insights

    • Removing friction creates new opportunities and increases market size.
    • Shared priorities of some of the best companies in the world:
      • Priority #1: Go build the best product you can possibly build
      • Priority #2: Make some revenue so that you can do more of Priority #1
      • Priority #3: Never do #2 at the expense of #1
    • Important technologies of the future look trivial today (like games or toys), just like the Internet did in the ’90s.
      • Examples: Crypto, NFTs, Biohacking sensors
    • Software innovation compounds.
    • Going forward, the best companies in the world will be built fully-remote, with in-person events deliberately distributed (all-hands gatherings, etc.)

    Background / Intro

    • Tobi created Shopify to solve his own problem: running his online snowboard store was really hard, and the only reason he could do it successfully was due to his background in software development.
    • Jason first interviewed Tobi on TWiST at Accelerate Ottawa in 2013
      • At the time, Shopify had ~200 employees with a “crazy” thesis: Amazon would not win it all, and some retailers would want to run their own online stores
      • Jason was originally in Canada to interview Chamath Palihapitiya
    • In their initial interview, Jason was struck by Tobi’s laser-like focus and thought Shopify had huge potential.
      • He remembered:

    “… in that interview [Jason made] some statements about the potential size of [Shopify] being hundreds of millions. I thought ‘I’m gonna roll with this but I’m not entirely sure if Jason is serious or not.'”


    Shopify’s growth & comparing ecosystems with Amazon

    “I have an unbroken track record of underestimating the potential of my own company, which I hope will continue.”

    • 85-90% of all the world’s money exists in databases. The world economy is almost fully digital.
      • The old concept of the e-commerce market is outdated and incorrect.
    • Shopify mainly differs from Amazon regarding direct-to-consumer brands
      • How? By giving them a “home base”, so they can own their storefront on the Internet, rather than “renting” shelf space from someone else.
    • Amazon has a very good sales channel for certain products, and people should use it if it’s appropriate.
    • Shopify’s App Store has helped fuel their growth “Commerce is complex, it’s very hard to build software that can address a lot of different use cases. The inspiration [for the app store] was operating systems.  An operating system that does a good job modeling the primitives can then be used for everything.” – Tobi

    “Commerce is complex, it’s very hard to build software that can address a lot of different use cases. The inspiration [for the app store] was operating systems.  An operating system that does a good job modeling the primitives can then be used for everything.”


    Removing friction creates new opportunities

    “Friction shapes the world a lot more than policy in most cases.”

    • There were roughly 40,000 online stores in the early 2000s. This was because it was so difficult to run an Internet business due to payment processing, order fulfillment, software development, etc.
    • When Tobi started fundraising, investors that said “no” would point to Shopify’s “low” Total Addressable Market (TAM) of 40,000 stores.
    • Shopify grew its TAM by greatly reducing the friction of setting up an online store, thus encouraging more and more people to either start new online businesses or to create a digital version of their physical store.
    • How’d they do it? Initially by building a payment gateway to make it easier to deal with merchants and collect payments.
      • The goal was to allow sellers to collect payments easily, and once they made sales, the entrepreneur could tell Shopify where to send the orders for fulfillment.
    • Like e-commerce, setting up a blog also used to be time-consuming and difficult, involving servers and coding. Now it’s been made nearly frictionless by companies like Squarespace or WordPress, and their markets have expanded as well.

    “Every time an entrepreneur makes it easier, more people participate.”


    Lessons learned during the pandemic

    “Almost every model and theory I had about how to work together [and] how to build things got either invalidated or got a significantly higher resolution. For instance, I believed that there was no way to replace proximity as a factor in building fantastic products, the proximity of a team is just so powerful, and so multi-dimensional… clearly that was incorrect.”

    • Early remote work pioneers like Matt Mullenweg (Angel S5 E7), and Jason Fried (E1099) were right. Business efficiency increasing while remote proved Jason and Tobi wrong.
    • The problem with pre-pandemic distributed work was that companies needed 100% remote participation, which was very hard to achieve before lockdowns were enforced.
    • High-quality product creation comes from high-fidelity teamwork, which proximity inherently creates.
      • However, this can also be created by great video conferencing software (Zoom), a solid setup (strong internet, good camera/microphone), and a way to mimic a whiteboard (productivity apps, screen sharing).
    • We are still in the early days of remote work, and the software will only become more seamless in the future.

    “This is the worst the software will ever be for remote work, it will only get better from here.”

    • Jason’s remote management checklist (SOD > EOD > EOW)
      • Start of Day (SOD): At the start of the day put in Slack what you’re working on in 1-3 bullet points
      • End of Day (EOD): At the end of the day when you’re done working, reply to that same post with what you got done and what you need help with
      • End of Week (EOW): On Friday, taking no more than five minutes, share the most important things you got done during the week

    “It’s a contest to see who can inform everybody and how in sync we can be with the least amount of meetings.”


    According to Tobi, the best companies in the world going forward will be fully remote:

    “I think I think the best companies in the world will be built completely remotely, at least with no stated headquarters. Being together in person is still going to be very important, but more deliberate.”


    Forced focus of lockdowns

    • Shopify zero-budgeted at the start of the pandemic and realized how unfocused they were.
      • Zero-based budgeting entails redoing an entire budget from scratch, rather than just modifying the previous year’s numbers
    • Due to the initial pandemic scare, Tobi became focused on building an “antifragile” business
      • An antifragile business is one that performs better under duress or in times of uncertainty
      • Antifragile is a book by Nassim Nicholas Taleb
      • Examples:
        • Uber – When people went into lockdown and stopped ordering rides, the demand for UberEats went up. When people come out of lockdown, demand for rides will rise.
        • Disney – When parks shut down, they centered their business around Disney Plus. They surpassed 100M subscribers in the first 16 months after launching in Nov. 2019.
    • Antifragility in practice: Many businesses will take the e-commerce lessons they learned during the pandemic and apply more software when running their physical locations.

    Compounding nature of software innovation

    “The narrative around programming is more interesting than people realize.  Since blacksmithing, we haven’t had a craft where the craftsmen actually make their own tools.

    • Humans are genetically the same as we were 75,000 years ago. The main difference between then and now are the tools we have available that and the stories we tell each other.
    • Innovation compounds when creators build on the innovations of others Hardware example: Battery revolution
      1. Billions of smartphones are produced, competition leads to fast-charging and long-lasting battery technology
      2. Tesla uses batteries in their cars and makes them cheaper and more effective
      3. Battery-driven Vertical Takeoff and Landing (VTOL) aircrafts are now made possible due to the advancements in battery technology
    • Software is the ultimate play of leverage for innovation because it combines zero marginal cost with infrastructure that everyone on Earth can add to and constantly improve.

    1,000 True Fans

    “We want to make entrepreneurship trivial on the Internet.”

    • Spending money on creators via the Internet can now be seen as voting for something to exist.
      • Everyone can now be a “Digital Medici” and sponsor the art/artists/products they want to see exist.
    • The promise of Kevin Kelly’s 1,000 True Fans essay becomes more attainable for a broader set of people with each new technological commerce innovation.

    “…there is a home for creatives in between poverty and stardom. Somewhere lower than stratospheric bestsellerdom, but higher than the obscurity of the long tail. I don’t know the actual true number, but I think a dedicated artist could cultivate 1,000 True Fans, and by their direct support using new technology, make an honest living.”

    Kevin Kelly
    • Shopify’s Fulfillment Network abstracts logistics away from the seller (just like the Payments Network did before it).
      • they reduce complexity by removing unnecessary information/hassle/steps
    • Jason claims to have seen a 100x increase in high-quality direct-to-consumer companies in the past few years, largely due to Shopify making it easier to run an e-commerce business by handling the technical and fulfillment aspects and allowing entrepreneurs to focus on the product.
    • Example: One founder is selling ~$60K worth of hoodies per month with minimal effort on the fulfillment side. Here’s how she does it:
      • Uses influencer partnerships to market the product
      • Takes orders through a Shopify storefront, which handles payments processing
      • Orders hoodies from a contract manufacturer and routes them to a Shopify fulfillment centerBecause the logistical side of the business was automated, the founder was able to focus on perfecting the product, and is now building her own version of “1,000 True Fans”.
    • Most of the modern Internet has been condensed into 3-5 major players. According to Tobi, it’s important to preserve the opportunity space so that achieving “1,000 True Fans” can still be possible.

    Click to Tweet about the show

    Watch / Listen to the full episode:

    The post Lessons from Shopify CEO Tobi Lütke: what he learned from scaling Shopify through the pandemic | This Week in Startups Blog appeared first on Jason Calacanis.

  • Jason Calacanis 01:35:39 on 2020-12-07 Permalink
    Tags: besties, calacanis, chamath, david friedberg, , podcast, podcasting,   

    The All In Podcast and Syndicate 

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    A couple of months ago my pal Chamath texted me and said “I want to do a podcast with me and you.”

    We discussed some names and landed on “All In,” as a tribute to our mutual friendship over poker. This was during the pandemic and in an election year, so there was plenty to talk about above and beyond technology, finance, and entrepreneurship, so we had a full docket of issues to work from.

    We invited two other poker buddies to come on the pod, David Sacks and David Friedberg, and got into a quick rhythm given the massive brainpower of the two Davids.

    We’ve now done 14 episodes and the podcast quickly went from the top 50 to 25 and then top three technology podcasts on Apple’s quirky podcast rankings.

    People have responded in a deep and meaningful way to the podcast, tell us that it’s their favorite listen when we drop an episode every couple of weeks. People say they love the friendship and comradery they feel as we laugh it up while discussing and debating the most important issues of our time.

    Fans tell me they wish the rest of the media world was more like the All In podcast, where folks listen and appreciate each other–even when they disagree. In fact, I think we appreciate each other MORE when we disagree, because it feels like we’re learning, evolving or simply getting to some central truths.

    Anyway, I’m not sure if many of you come to the blog any more, but I thought I would post this to give a little background on how this whole thing got started and let you know how to find the podcast.

    This linktree will take you to all the places to listen:

    and you can see us on Zoom if you subscribe on youtube

    For fun Chamath suggested we launch an angel syndicate, so we put up a form for accredited investor to sign up at here:

    At the time of me posting this, 3,000 of you signed up to invest with us–which is nuts! It took me six years to build my angel syndicate to 5,500 members (!!!). Note: if you signup for the All In syndicate you’ll also seem my deal flow, but not the other way around. So if you’re a member of my syndicate at you need to signup again for the All In syndicate.

    The post The All In Podcast and Syndicate appeared first on Jason Calacanis.

  • Jason Calacanis 23:43:50 on 2020-08-08 Permalink

    A fourth option: how #microschools will save our children 

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    It became clear to me during July, when coronavirus cases spiked at precisely the time they told us it would take a break, that school would not start in September. 

    Realizing this, I started floating the idea of creating a “microschool,” a concept that sits between two of the most polarizing points on the education spectrum: private school and homeschooling.

    Many consider the flight of the rich to private school, combined with the recently uncovered hacking and corruption at elite colleges, as a fundamental breakdown of the fellowship of the American public education system. 

    [Click to Tweet (can edit before sending):

    Every conversation I’ve ever witnessed about homeschooling went to the same place: with people marginalizing it as a wacky, hippie-dippie pursuit that created smart but socially weird kids. 

    A “microschool” sits between these two options, because in the model — as defined by me — you have a teacher at your home with multiple students. 

    A microschool, by my definition, achieves the following:

    1. You remove the social isolation concern of homeschooling.
    2. You drop the class size dramatically, from the standard 20-30 students down to four to 10.
    3. During a pandemic like coronavirus, I would guess that every logical person of science would state that smaller is safer (you can research this yourself online).
    4. You drop the cost of a private school from $30-50k a year to $5-10k.

    As an investor in highly disruptive companies, that last point is the one that got me in hot water with the hysterical Twitter mob this past week. 

    In my blunt, capitalist fashion, I tweeted that I was looking for the best teacher for my microschool. I would beat their current compensation and give anyone who referred me this person a $2,000 gift card to UberEats.

    As an early investor in Uber, this last part was considered extra elitist to the salty, radical left on Twitter. That contingent doesn’t give anyone the benefit of the doubt, instead, immediately they make everything about class, wealth, politics, identity politics, and generally dunking on anyone who is easy to hate (which, I’m self-aware enough to know, I am). 

    So, I wound up on TMZ, the New Republic, and the DailyMail, which is something I never expected in this lifetime, as well as talking with an ABC news reporter. 

    Dr. Phil’s producer has asked me to come on (debating that one), and essentially I went viral for 48 hours.

    It was a level of attention, for what is a super pragmatic idea, that I didn’t expect, but in reality this flareup feels akin to about 20 minutes and 20 seconds in the life of Kanye West and Trump, respectively. 

    The punch line of all of this is that the concerns folks had, that I was “stealing” a teacher from other students, and that this was another example of the growing chasm between the rich and poor, flies in the face of, well, math!

    First, 95% of the people applying for the position were out of work. Making this $60-70k position with benefits a net new job created in the world. 

    Second, we elected to give 50%+ of the slots in the school to folks who wouldn’t be able to afford private school.

    Third, we are currently in public school. Everyone just assumed because I had some success in the second half of my life that I was an elitist in some $50,000 private school — wrong! 

    Fourth, and most stunningly, microschools are the opposite of elitist — they are socialist and capitalist at the same time. 

    Basic Math:

    1. Ten students
    2. $50,000-$75,000 teacher (all-in cost with benefits, based on the average salary — do some Google searches, teachers are underpaid)
    3. That’s $5,000 to $7,500 per student, which over 40 weeks (200 days) of school is $25 to $37.50 per student, per day

    This model assumes the 10 parents manage the teacher, live in a reasonable distance of the school, and at least one of the 10 families has a backyard or extra space for the students. Even if you add $12-$24,000 to the total cost, say if you wanted to rent a space, you are still at 10% to 20% the cost of a private school.

    So, today parents have three options:

    1. free public school
    2. homeschooling
    3. $35,000 to $50,000 a year private school 

    This changes the competitive landscape for education into four options:

    1. free public school
    2. homeschooling
    3. $5,000 to $7,500 for a microschool
    4. $35,000 to $50,000 a year private school 

    Does anyone believe that inserting a 4th option to schooling options is a bad thing?

    Only one group seems to think this is a horrible idea, and it’s not parents or students, it’s the teacher’s unions and the administrators at public schools. 

    Consider the big picture: 

    1. U.S. outspends every other country in the world on education.
    2. U.S. trails countries that spend less than us.
    3. The average American gets paid ~$25 an hour. 
    4. Based on our average hourly wage in America, sending a child to private school is ~2,000 hours of work.  In this model, sending one child to a private school would eat up a parent’s entire salary.
    5. In the microschool model, a parent would have to work — paradoxically — one hour for every day their child went to school (on average). If you made $10 an hour, obviously you would need to work about three hours.

    I’m not an expert on education, but I am an expert at identifying and investing in disruptive models — and microschools feel really, really disruptive in the best of ways.

    We all want what is best for all of our kids, and we all know that school ain’t starting in September. 

    Given these universal truths, I suggest we all start thinking creatively and share our learnings while ignoring the crazy, vocal minority of virtue-signaling communists who hate innovation and want their lives run by our dysfunctional government … you know, the same government that has us spending more and getting less from education today, and which is performing in last place when it comes to dealing with the crisis. 

    Our politicians and institutions are failing us right now, so while we slowly work to fix our broken system my best advice is to be as radically self-reliant as you can — and that’s what #microschools are.

    Best, Jason 

    PS – There is a pandemic pod hack that drops these numbers down even further, which I will write about tomorrow. 

    For now, if you could hit reply (or comment) and give me your most deeply considered feedback on:

    1. How to make a microschool more available to more students. 
    2. How to run a microschool better. 
    3. How you are addressing the 2020/2021 educational year. 

    I started a Slack room called #microschools in my podcast’s Slack, which you can join at:

    The post A fourth option: how #microschools will save our children appeared first on Jason Calacanis.

  • Jason Calacanis 22:07:50 on 2020-07-09 Permalink

    Microschools are the future–how do we start one? 

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    vacant white painted classroom with chairs, tables , and map on the wall

    It’s becoming very clear to me that school isn’t going to be the starting, or be the same, this September, as many of us hoped it would.

    As nimble as educators were to move to remote education, something is lost when we put our kids in front of a webcam as opposed to a group of their peers.

    Given this, our family has decided to start a microschool in the Bay Area starting this fall. We expect somewhere between one to five students, and we are starting the search for an teacher who wants to be apart of the microschool revolution/evolution.

    If you’re teachers with five years of experience or more and you want to come on this adventure, we set up a quick application form.

    The post Microschools are the future–how do we start one? appeared first on Jason Calacanis.

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