Author: Jason Calacanis

Social Media Addiction: Why I’m taking a Twitter break.


This post is by Jason Calacanis from Jason Calacanis


For the second time in the past five years, I’ve decided to take a break from Twitter.

I’m a functional Twitter addict, getting all of my work done and maintaining important relationships while spending far too much time on the platform. 

When I wake up, I check Twitter before my email and SLACK.

Before I go to bed, I thrash between Twitter, podcasts, audiobooks, and playing chess.  

All day long, be it a workday, the weekend, or on vacation, I’m sucked into my replies, trending topics, and Twitter feed. 

I love it, but sometimes I love it too much. 

While I don’t regret the time spent there, it is a blocker to getting other things done, and while it’s worth it on so many levels, the truth is it can put even the most optimistic person in a foul mood. 

The amount of trolling and dunking, which can be entertaining, can sometimes become exhausting. 

So, I decided this week to focus on two media channels for the rest of the year: my podcasts and my next book. 

I’m still checking Twitter, and I will retweet things and like them, but I’m not going to reply to folks OR start new tweets. 

I will automate the sharing of podcast episodes and blog posts to Twitter, so folks know when new content lands, but for now, I’m going to clear my mind and focus on getting my passion–This Week in Startups–to consistently publishing 5x a week. 

Oh yeah, I also (Read more...)

On 2021 startup valuations


This post is by Jason Calacanis from Jason Calacanis


Some folks in our angel investing club (thesyndicate.com) have asked me for my thoughts on the surge in early-stage valuations.

The market is scorching hot, with startups across all growth stages getting funded faster and at higher valuations. 

[ Click to Tweet (can edit before sending): https://ctt.ac/GdU89 ]

The dollar amounts raised are often staggering, but so are the exits — which are driving this.

When there is a large number of meaningful exits — from Uber to Airbnb to Coinbase — investors get enthusiastic about investing in the next wave of unicorns.

This causes valuations to quickly double and triple, with investors reporting, “the valuation doesn’t matter if this becomes the next unicorn!”

Of course, it does matter since most companies go to zero, and you can invest in three startups at a $10m valuation for the same price you would pay for one at $30m. 

Three swings at bat dramatically increases your chances of hitting an outlier.

Now, if you could invest in Uber or Airbnb’s angel round, Series A, or Series B, you would certainly do it, but there is no way to know which startup is the next Uber or Airbnb (at least not with certainty). 

Our firm and investment club are adjusting to this moment to focus on four things:

  1. We are investing in high-quality startups at reasonable prices, as we have always done. 
  2. We are investing in select, very high-quality startups at these higher valuations. 
  3. We are helping existing portfolio companies raise (Read more...)

Republic CEO Ken Nguyen on making early-stage investing for everyone | E1199


This post is by Jason Calacanis from Jason Calacanis


Top Takeaways


  • Ken’s worldview: crowd investing is a powerful way to give people around the world access to high-growth opportunities and give companies a way to raise money while creating a deeper connection to their community.
  • Startups are staying private longer, so platforms like Republic are the only way for the average person to get access to private companies.
  • Ken’s goal is to make it easy for people to begin investing for as little as $10. Republic achieves this by streamlining everything related to organization, legal, & compliance.
  • Republic uses a Crowd SAFE, which essentially groups all investors together as one line item on the startup’s capitalization (cap) table. This makes it easy for the company raising money to manage.

Listen on Apple Podcasts

Intro


Ken Nguyen (also appeared on E856)

  • Ken & his parents emigrated from Vietnam to California when he was in elementary school, which partially influences his mission to allow people from all over the globe to invest in great startups.
  • Co-Founder & CEO of Republic (2016-Present)
    • Equity crowdfunding platform
    • Republic empowers everyone to invest in the future they believe in by providing access to startups, real estate, crypto, and video game investments.”
  • Previously:

Republic’s Funding (more than $70m to date)

  1. $2.1M Seed AngelList, Upventures & others (Dec 2017)
  2. $12M Early Stage VC led by Binance Labs & NGC Ventures (Jun 2018)
  3. $36M Series A at $137M Post led by Galaxy interactive (March (Read more...)

Insights from Giggster Co-founder Hank Leber on building a location marketplace for creators & content production | E1196


This post is by Jason Calacanis from Jason Calacanis


Top Insights


  • Building a business on top of another platform is risky, as revenue can go to $0 overnight by no fault of your own
  • Adding simple and easy solutions to archaic industries and business processes can result in rapid adoption
  • Giggster filled their marketplace supply-side first: once there was a large volume of high-quality supply, demand generation was much faster and mostly organic
  • When all sources of revenue are on the line, even archaic industries like film production can adapt quickly
  • Since Giggster has been operating successfully before raising money, they know their unit economics and are comfortable putting together an aggressive growth plan

Intro / Problems with building on other platforms


Guest: Hank Leber | @hankleber

  • Co-Founder & Head of Growth, Giggster (April 2019-Present)
  • Website: https://giggster.com
  • Hank previously was CEO of GonnaBE a planning social media app (they presented at LAUNCH Festival). The concept of planning socially wasn’t embraced by users.
    • Lesson learned: if you put out your plans publicly and no one comes you look like a loser. “You have an idea that everybody thinks sounds great, then there’s an ugly cultural truth somewhere that makes it not a real thing.” – Hank Leber
  • Hank also had a company called Vytmn which was a “growth as a service” tool built on top of Twitter
  • Twitter shut down one of their key features, the ability for to automate actions like DMs, which killed (Read more...)

Snack’s Kim Kaplan PLUS 3 key metrics for consumer, enterprise SaaS & marketplace startups | E1195


This post is by Jason Calacanis from Jason Calacanis


Top Insights


  • “Match has done a phenomenal job at working with different companies, acquiring different companies.”
  • It has been significantly easier to raise capital for Snack post-Bumble’s IPO. A sector can become stale to investors, especially after being burned repeatedly. Proof of a publicly traded challenger company makes picturing a success easier.
  • “Every 8 to 10 years there’s a new dating app that kind of enters into the space and Tinder’s now nine years old. So it is the right time for that next dating out to come in and usurp them. And I fundamentally believe that’s what Snack is doing with a video-first approach.”

The post Snack’s Kim Kaplan PLUS 3 key metrics for consumer, enterprise SaaS & marketplace startups | E1195 appeared first on Jason Calacanis.

Paul Judge on helping lead SoftBank’s $100M Opportunity Fund, the future of VC & more | This Week in Startups Blog


This post is by Jason Calacanis from Jason Calacanis


Top Insights


  • Investing over zoom expands the top of the funnel and lowers the barrier to entry for all founders
    • Investors can take 2-5x more meetings with founders from anywhere in the world
  • Paul’s thesis: Investing in overlooked founders will likely generate outsized returns
    • The American Southeast and Midwest include 44% of the US population but only receive 14% of VC funding
    • Despite this, 36% of last year’s Inc. 5000 reside in these regions with a median growth rate of 161% year-over-year
  • The “either-or” debate between making existing firms invest in underrepresented founders from their main funds OR raising “opportunity” funds that are specifically focused on underrepresented founders isn’t helpful, both are necessary to make VC funding more equitable
  • Jay-Z had the best Q1 2021 of any entrepreneur or investor
    • Tidal was acquired by Square for $297M, he sold 50% of Ace of Spades to LVMH for ~$300M, launched $10M cannabis-focused fund to back black founders, Oatly filed for IPO

Intro


  • Paul Judge, Ph.D. is Managing Partner of Panoramic Ventures, a VC fund that invests in “underserved geographies and overlooked founders” prioritizing the American Southeast and Midwest. Paul is also Co-Founder & Executive Chairman of Pindrop, an information security company that provides risk scoring for phone calls to detect fraud and authenticate callers). Pindrop’s most recent valuation was $900m in 2018.
  • Paul also serves on the investment committee for SoftBank’s $100m+ Opportunity Growth Fund to invest in (Read more...)

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


This post is by Jason Calacanis from Jason Calacanis


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.

Intro


  • 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.”

Jason
  • 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.

The All In Podcast and Syndicate


This post is by Jason Calacanis from Jason Calacanis


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 (Read more...)

A fourth option: how #microschools will save our children


This post is by Jason Calacanis from Jason Calacanis


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): https://ctt.ac/daT56 ]

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 (Read more...)