TWIST Episode 1251, China punishes Didi, Twitter’s new feature, UAE makes it rain + Do Kwon of Terraform Labs

I cover China’s increasing penalties for Didi , Twitter’s test of a downvote feature, and how the UAE was able to induce rain with electricity. Then Do Kwon, the founder of Terraform labs joins to discuss his stable coin project TerraUSD, the underlying cryptocurrency LUNA, and shed light on Tether as crypto insider.

00:00 Start
02:52 News – China increases the pressure on Didi for “data privacy”
10:33 Dell – Sign up for a free IT consultation and a 5% off coupon at
12:13 Twitter tests up/down voting tweets
17:32 UAE figures out how to make it rain with electricity
21:02 Notion – Go to and use promo code TWIST to get $250 off the annual team plan
22:38 Interview – Do Kwon of Terraform Labs
27:14 Why you can’t build decentralized finance with centralized stable coins
31:18 What is an algorithmic stable coin?
35:26 Vanta – Automate your SOC 2 report, get $1,000 off at
37:02 Why did Terra’s price fluctuate as a stable coin?
43:46 What Do thinks China’s strategy is re: crypto
59:56 What is going on with Tether?

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

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 among 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 do the All in Podcast weekly now, so that means I’m doing six podcasts most weeks. 

Now, for most humans, six podcasts a week seems like a lot, but for me, it’s like going to lunch or dinner six times a week with the most exciting people in the world — in other words, it’s nothing. 

That’s a lot of cognitive work.

My current plan is to take the rest of the year off Twitter and focus on the podcasts (TWIST & All In) and the book while growing my two startups, and the LAUNCH fund. 

The last time I took off six months, I got the book ANGEL done, traveled the world to support it, and that little niche book sold tens of thousands of copies and was translated into 10+ languages … and my angel investing club ( grew from 1,000 members to 8,000. 

So, it’s time to write the book. I’m not ready to talk about the details yet (and I haven’t even sold it), but it’s going to be a barn burner.

Candidly, I’m more excited with you reading the book in the spring of 2022 than I am getting using Twitter right now. So, I’m going to follow my heart.   

best Jason

Note: I did a short audio piece on this decision last night on

Rad Power Bike Review: it’s fun!

On 2021 startup valuations

Some folks in our angel investing club ( 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): ]

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 money during this frothy market.
  4. We are meeting with as many startups as possible and noting when we pass because of the valuation so that we can meet with them again in the future. Many times a startup will “catch up” to a high valuation, and the next round will allow us to engage at a more defensible valuation. 

We invested in Calm, Uber, and Thumbtack for ~$15m — combined. 

While the $5m Seed round may be over for now, we have seen several pre-launch startups command $15m to $50m valuations. If those startups are led by a serial founder, it’s justifiable, but most of the time, they are first-time founders. 

We are content to sit out these Seed rounds and wait to see if the startup gets to product-market fit. If a pre-launch startup raises at a $50m valuation, for example, and then gets product-market fit and hits $1m in yearly revenue, the valuation is likely to be $10-25m in a normal market. 

This “filling in the valuation” strategy is acceptable for founders who have discipline, but it does carry the obvious risks of a down round if they don’t. Most founders seem to understand this, with many telling me, “I know this valuation is crazy, but we are taking advantage of this moment.” I would do the same if I were them, so no judgments — just make sure that you have the runway to fill in that valuation. 

For investors, you don’t have to hit every winner to be a big winner. In fact, you only need to hit one. 

In a hot market like today’s, we encourage members of our investment club to evaluate their goals, pace themselves, consider making adjustments to their strategy, and always remain disciplined — by focusing on great founders, quality products, and delighted customers.

Great founders.

Quality products. 

Delighted customers. 

Those things don’t happen by accident. 

Best, Jason
PS – Join us next week for Meet Our Fund, where 25 venture funds are pitching thousands of founders

Lessons from Oura CEO Harpreet Rai on improving sleep, hardware, landing NBA partnerships & more | E1213

Subscribe on Apple Podcasts

Top Takeaways

  • Improving sleep is a massive market opportunity. It has fueled Oura’s growth as well as other companies like
  • “99.9% of Americans will try to sleep tonight, but only 10% will exercise per day.” – Harpreet Rai
  • For optimal health, you want a low resting heart rate (your heart is strong and you are relaxed when you sleep) and high heart rate variability (your body is adaptive).
  • Most hardware companies try to raise too much money early, which sets expectations too high. It’s better to test and iterate. Hardware development timelines are too long and risk of delay is too high to keep momentum when over-capitalized.
  • Employers have used Oura to keep their employees safe in COVID, sensor technology can often detect sickness before symptoms are felt.

Listen on Apple Podcasts

Guest: Harpreet Singh Rai | @harprizzle14

CEO Oura Ring (2018-Present)

  • Joined as President in May 2017 (4 years into Oura’s life)
  • Previously worked as a portfolio manager at Eminence Capital for 9 years
  • Began career in Investment Banking at Morgan Stanley
  • Majored in MEMS, Micro Electronic Mechanical Systems (sensor design) at University of Michigan

Oura’s sleep cornerstone

  • Sleep has been a major driver for customer adoption of the Oura ring.
  • There is a limit to productivity if you are not getting good sleep.
  • Poor sleep reduces your critical thinking ability. The quality of your decisions matters. For example, “if you’re a PM at a software app, making the right decisions on data analysis or UX flow can lead to dramatically different outcomes.”

“99.9% of Americans will try to sleep tonight, but only 10% will exercise per day, and only 15-20% will work out each week.” – Harpreet Rai

It’s hard to eat well when you have a bad sleep

  • Two hormones control your appetite. Ghrelin determines how hungry you feel. Leptin determines how full you feel after.
  • When you are sleep-deprived Ghrelin levels double and Leptin levels go down by half.
  • Evolutionarily, if you were not sleeping, it was likely because you were under stress from a predator (like a Cheetah), and your body wants to maximize calories to be ready to run.

How Oura verifies their scores

  • A subject wears the Oura ring at a sleep lab (like UC Berkeley), where they are hooked up to the state-of-the-art sensors.
  • 16 nodes read brain activity, and then data scientists tune the Oura ring’s algorithm to generate similar conclusions from its sensors.

Key Metrics used by Oura

Lowest resting heart rate

  • Reaching your lowest resting heart rate requires both physical and mental relaxation. When you are relaxed, it reduces stress on the autonomic nervous system (the vagus nerve that connects your brain and your body).
  • Research shows that when you get sleep that leaves you well recovered and well-rested, you’ll normally reach your lowest resting heart rate sort of midway through the night.

Heart rate variability

  • Heart rate variability (HRV) is the variation between every single heartbeat.
  • High HRV is a good signal; it means your body is more responsive and capable of adapting to situations. Low HRV is indicative of stress, smoking, and poor health.
  • Affordable, compact sensors precise enough to measure HRV are a recent advancement.

Sleep Score

  • Electrical signals, breathing, temperature, and movement can indicate which stage of sleep you are in (Light, Deep, Rapid Eye Movement (REM), Awake).

Oura’s business model

  • Oura designs hardware, develops software to analyze & display user’s health patterns, and markets their product direct to consumers & businesses.
  • 500K+ rings sold to date, ~350K in the last year.
  • Rings retail from $299-$399 with 2-year warranty, there is no additional fee to use the Oura app.
  • 100% online at, they have not yet used channels like Amazon.
  • Similar to Warby Parker, Oura designed a ring fitting kit that comes in a small box for customers to try on.

COVID Detection, Wellness Monitoring, and NBA & Enterprise Partnerships

  • Oura regularly monitors the temperature of the skin, HRV, respiratory rate, and other signs. Together these signals can typically detect stress and sickness before the wearer.
  • For frontline health care workers, Oura donated 2000 rings and had a sponsor donate another 1000 rings to hospitals across the US.
  • The team used early research and findings to create an algorithm rolled into an enterprise application, “Health Risk Management.”
  • Oura partnered with the NBA, UFC, NASCAR, Red Bull Racing, Las Vegas Sands, and others for COVID monitoring using their Health Risk Management platform.
  • Oura’s cost is low compared to shutting down the economy, daily testing, or high cost of human health.
  • Most organizations can’t afford a test every day (they weren’t even available), the Las Vegas Sands used Oura to monitor the health of their employees and then used Oura data to prioritize those who got tests.

Creating frameworks to avoid Big-Brother

  • Everything needs to be opt-in from the employee side. Empower the individual, notify them first.
  • Oura will not tolerate companies using their rings to terminate employees. (Oura’s contracts give them the right to terminate their customer contract if enterprises misuse data.)
  • Admins can have pre-customized notifications to employees (For example: send a notification when someone may be sick).
  • Oura sees interest from a lot of corporations as they go back to the office to de-risk against new variants and Flu season risks.
  • “Oura-wellian.” – Jason
  • Companies want de-identified tracing tools and frameworks to avoid data risk on their part. They embrace Oura’s cautious and thoughtful approach.


  • Google and Apple have both said they want to own health. Apple has the Apple Watch, and Google has acquired FitBit.
  • Oura plays nicely with both of them; they distribute the apps on their app stores and integrate with both Apple Health and Google Fit.
  • Oura can remain neutral because of its focus on sleep and because it is seen as a complementary product, many Oura users (estimated ~1/3) also wear a smartwatch.

Why the finger is better for monitoring than the wrist

  • For accuracy, the pulse signal from your finger is about 100 times stronger than the wrist. This is because the skin is thin, and the arteries are close to the surface.
  • Oura samples at 250 hertz. This means their LEDs fire 250 times per second (LEDs are used to shine into the arteries to measure blood flow).
  • If bootlegged an Apple Watch or Fitbit to 250 hertz it would die in about an hour.

Oura roadmap & potential experiments

  • Oura’s current competitive advantage is the accuracy of its data. Improving its sleep staging algorithm to continue to be the market leader is important.
  • Jason asked about implants: Basic procedures for simple implantation still cost $5K in the US, so it’s not going to be a near-term solution.
  • Due to the size of the data set at Oura, they can improve their algorithms faster than the hardware sensors themselves. More data improves the fidelity of the insights.

Ring design

  • Oura will likely create both thinner rings and ones with more design.
  • They are thinking through the best way to do design partnerships and have already had inbound interest from brands like Tiffany and Gucci.

Advice for Hardware Founders

  • Test and iterate. Make sure you have product-market fit, then when you are more confident, raise more capital.
  • Many hardware companies aggressively raised capital, but with an aggressive raise comes high expectations. Physical products have a longer development cycle than software, so investors accustomed to software performance will be disappointed.
  • Companies like Jawbone fell victim to this dynamic.

Oura’s financial future, SPACs M&A

  • Apple is selling 15M+ Apple Watches, which is beginning to show the size of the market.
  • Oura has seen a lot of inbound interest from SPACs, but does not see it as strategically advantageous at this point.
  • Harpreets’ hedge fund background makes him appreciate the rigor of being a public company, but he knows Oura is still early in its distribution maturity (only DTC with some enterprise.
  • M&A in the wearables & health space will continue to heat up. Google closed Fitbit, Amazon launched a wearable, and rumors suggest Facebook will be trying to do this as well. is curated list of the most generous software discounts for startup founders by @jason, @launch & @twistartups

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

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


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 2021)

Republic Stats

  • 1 million investors on the platform
  • Avg. raise is ~$600k

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Why is crowd investing a new thing?

  • After the Great Depression, Congress enacted legislation that only allowed “accredited investors” (read: millionaires) to invest in private companies
  • All non-accredited investors were deemed unfit to invest in private companies and were banished to the public markets and index funds
  • Investing and financial services continue to be highly regulated.
  • In 2012, Barack Obama signed into effect the JOBS Act (Jumpstart Our Business Startups Act), The JOBS act went into effect in 2016 allowing for some equity crowdfunding
  • Republic focuses on Reg Crowd Funding (CF) and Reg A, these regulations were changed in March 15th, 2021 allowing for more investment:
    • CF: $5M max raise (previously $1.07M, set in 2016 Jobs Act)
    • A+: $75M max (previously $50M, set in 2016)
  • Republic is shaping laws – was referenced over 20 times in 2021 SEC ruling
    • The SEC is moving much faster than Ken though possible (still slower than private companies to protect investors).
    • Ken thinks President Biden’s SEC will move slower at loosening regulations than Trump’s because there is a different focus.

What it takes to raise on Republic

  • Diligence is required to list on Republic, but legal and accounting fees for new startups to raise is less than $15k (for most it is much less).
  • To use Republic to raise money, companies pay a fraction of the amount they are raising (on average):
    • 6% in cash
    • 2% in stake of the company (this gives Republic upside in the company and an incentive to make sure only good deals come on the platform)
  • Companies that have a large audience and bring investors to the Republic platform will pay a lower fee. You can think of them in two groups.
    • Those looking to find investors from the community that invests on Republic (Low fee)
    • Those with large following that will use this infrastructure to make it easy to raise (High fee)

Recent big raises on Republic

  • Sahil Lavingia (E1188 ) & Arlan Hamilton (E1080, Angel S2 E5, E772) both raised $5M rounds
    • Gumroad – Sahil Lavingia
      • Crowd SAFE: $5M raised at $100M valuation from 9346 investors
      • Co-investors: Naval, Jason Fried put in $1M as anchor investors
      • 8x price to earnings, over $10M ARR, growing 120% year over year, team of 10
    • Backstage Capital- Arlan Hamilton
      • Crowd IPA: $5M raised – for 10% of future earnings of Backstage capital (~10% carried interest & 10% management fees) from 6958 investors

“My question for VCs criticizing this model is: If your assessing a b2c business that has such a relationship with his customers that these customers would part ways with 500 bucks, not getting anything back [except equity], just on the belief that one day this company is going to succeed. Is it a good signal or is it a bad signal if a company can convince 10,000 customers?”

Ken Nguyen

How power is shifting to the crowd

  • When people are invested in a business they become evangelists for a product. This is especially helpful when a product becomes commodified (like Skyy Vodka Ken used to work for).
  • In 5 years of data from Republic there have not been instances of fraud (this doesn’t mean all investments worked out).
  • There are more reasons than purely financial why people invest on republic.

“Our tagline is aligning profit and passion. The smaller dollar amount that you enable someone to invest the passion bucket is going to be more and more important in their decision making process.”

Ken Nguyen
  • Republic’s social component:
    • People can write reviews on the platform, saying why they invested (it also shows amount invested if they check that box).
    • A co-investor is highlighted with their track record of investing.
    • There is a space for discussion on republic
    • See Review Screenshot & Co investors section

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We recently launched a curated list of the most generous software discounts for startup founders. View all deals at

Discord in talks to sell to Microsoft for over $10B | E1190

Top Insights

Discord and Slack have had strangely similar journeys

There is a correlation between gaming-focused founders and making great messaging products

  • Rahul Vohra (Runescape > Superhuman), Stewart Butterfield (Glitch > Slack), Jason Citron (OpenFeint > Discord)

Microsoft is paying a premium (likely over 75x price to sales), but Discord fits perfectly into their “Netflix for gaming” ambitions

$10B isn’t too steep considering their market cap is approaching $2T

Background on Discord

Recent history:

Discord is a voice and text-based messaging app that is largely used by gamers for in-game communication, and it was founded by Jason Citron in 2012

A “server” on Discord is the equivalent of a “workspace” on Slack: a dedicated space for people to communicate about a specific topic

In June 2020 after COVID hit, Discord capitalized on the stay-at-home orders and changed their tagline to “Your place to talk.” – targeting fan communities of books, music, art, tv shows, and more to expand beyond just gamers

In January of 2021, Discord ran into some controversy when they briefly banned the r/wallstreetbets server which now has around 600,000 members

  • Wall Street Bets is an infamous subreddit that set off the GameStop fiasco in January – and they use Discord to communicate in real-time via voice chat
  • WSB’s server was banned for one day, and after being reinstated, Discord offered to help WSB moderators due to the amount and intensity of their users
  • We covered the WSB/Robinhood fiasco on an emergency pod back in January

Discord user metrics:

Discord has 140M+ MAUs as of December 2020

  • Other MAU stats: (as of Feb. 2021 via Statista)
  • WhatsApp – 2B
  • FB messenger – 1.3B
  • We Chat – 1.2B
  • QQ – 617M
  • Telegram – 500M
  • Snap – 498M

How they make money:

  • Discord makes money by selling a $100/year premium subscription called Nitro and also by taking fees from games sold on its servers
  • Benefits of Nitro: larger file uploads, HD video screen share, extra server support, personal profiles on servers
  • The core app remains free, so users only pay when trying to access premium features
  • Discord was rumored to be up for sale in 2018 – but did not proceed with buyers due to CEO Jason Citron allegedly opposing an ad-based model proposed by the would-be buyers

Discord generated $130m in revenue in 2020 and has raised $480M since inception

History of Discord and how it’s different but similar to Slack

Discord and Jason Citron had a very similar founding story to Slack and Stewart Butterfield’s

  1. 2002: Launches an MMO (Massively multiplayer online game) called “Game Neverending” which eventually shuts down due to inability to fundraise
  2. Stewart then creates Flickr from the well-received photo-sharing features of “Game Neverending”
  3. 2005: Stewart sells Flicker to Yahoo and starts working there running Flickr
  4. 2008: Stewart leaves and starts a new game called “Glitch”
  5. Glitch eventually fails, so Stewart focuses on the internal chat app they built, which eventually becomes Slack
  1. 2011: Jason Citron sells his social gaming startup OpenFeint to GREE for $100M
  2. While working on his next gaming project, Citron noticed how awful the current voice messaging software was, making it hard to strategize with teammates while playing online
  3. 2012: When his next project showed signs of failing, Citron pivoted to create Discord to meet the needs of its users

Interesting trend: Talented video game designers making amazing messaging products, for example:

  • Rahul Vohra worked on Runescape before Superhuman
  • Stewart Butterfield worked on Glitch before Slack
  • Jason Citron was a successful gaming entrepreneur before Discord
  • Theory: if you can make a game that engages users, you can make a product that engages customers

Deal breakdown: Discord at $10B compared to Slack at $27.7B?

  • Slack 2021: ~$900M in revenue (43% YoY growth), sold for $27.7B (~30x revenue)
  • Slack is geared towards enterprise customers, startups and SMBs
  • Discord 2021: ~$130M in revenue, in talks to sell for over $10B (~75x+ revenue)
  • Discord is geared towards communities, social and gaming

Microsoft is willing to pay a premium for Discord based on its revenue footprint… so what is their thesis?

Microsoft’s major consumer play

Every other FAANG company has a massive, industry-leading consumer business:

  • Facebook – social
  • Apple – hardware/app store
  • Amazon – marketplace
  • Netflix – streaming
  • Google – search

Microsoft’s big consumer bet appears to be in gaming (they own Xbox, Minecraft, and 30+ game studios)

  • With a ~$1.9T market cap, they have the capital to take big swings in M&A

Timeline for Microsoft’s recent gaming acquisition spree:

  • January 2019 – Microsoft CEO Satya Nadella explained his vision for their Xbox subscription:

“We describe it as, ‘Netflix for games'” – Satya Nadella

  • December 2020 – The latest Xbox console release helped Microsoft surpass $5B in gaming revenue during their most recent December quarter (Q2 2021 on their fiscal calendar), up 51% year-over-year (via GeekWire)
  • Xbox content and services revenue increased to $3.5B due to Xbox Game Pass subscriptions
  • Game Pass hit 18 million subscribers in Jan. 2021
  • Game Pass costs $10/month for standard and $15/month for the ultimate package (Ultimate includes XCloud, allowing gamers to play cross-platform)

In summary

Microsoft (~1.9T market cap) sees every other big tech company with a major consumer business and understands that gaming is the clearest path to building its own

$10B for Discord is a fair price to pay if Microsoft integrates Discord into their cloud-gaming subscription products ($10B is well under 0.05% of Microsoft’s market cap)

Microsoft is building a quasi vertical monopoly in gaming – they now own:

  • the hardware (Xbox, Surface, PCs)
  • the software (Bethesda, Minecraft, Xbox Game Studios, dozens of original titles exclusive to Xbox)
  • the communication platform (Discord)

We recently launched a curated list of the most generous software discounts for startup founders. View all deals at

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

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:
  • 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 their revenue ($1M ARR at peak)

“… do not build on the back of another platform, if they can kill you, they will, it’s not your money. That’s their money that you’re stealing.”

Hank Leber

Giggster’s founding story

  • Hank and his Co-Founder Yuri Baranov were not from the film industry, they are tech entrepreneurs
  • How they discovered the market opportunity with Giggster:
    • Yuri is LA-based and lives in a nice house near the water
    • One day, a production scout knocked on his door and offered him $70K to shoot at his house over two days for CSI: Miami
    • The process included door knocking, clipboards, paper contracts and excel spreadsheets
      • this “business flow” was terrible for a $70K transaction, so Yuri told Hank about it and they started doing some research on the production location industry
      • After realizing the location industry had been run this way for decades, they started Giggster
  • Giggster is a two-sided marketplace for video production, meetings, weddings & events. Think Airbnb for production locations and events.
    • Larger clients would be Netflix, HBO, Hulu, large production companies, etc.
    • Smaller clients would be TikTokers, YouTubers, Vloggers, etc.
  • How Giggster differs from Airbnb and VRBO:
    • Short-term rental platforms do not allow production shoots because they require more overhead: insurance, more people per location then allowed, production parking, waivers, etc.
  • Giggster added a services element because some film production teams need higher-touch support (above $2500-$3000 a day) these services include:
    • Logistics
    • Permiting
    • Power
  • In California, you can rent your home for up to 14 days per year tax free
    • Giggster has some client who shut down their listing after being booked for 14 days for this reason

Creating the marketplace supply-side first

“What we’ve found is, chicken and the egg, locations matter first. As long as we have the supply we can generate the demand.”

Hank Leber on starting a marketplace

Giggster has almost 10,000 locations on the platform

  • In the early days, they filled the supply-side inventory by:
    • partnering with Hollywood agencies, who already had direct relationships with private property owners
    • they also knocked on doors for early customers
    • filling the supply-side first turned out to be a good decision, as it created an immediate flywheels with renters
  • Customers needed a lot of education, so Giggster built out detailed FAQs and comprehensive signup flows
  • Demand has been strong and scouts are now loading their locations onto Giggster
  • If a major client (Netflix, HBO, etc.) needs a location that does not exist on Giggster, they will hire location scouts to go find and matching location and on-board them
  • Giggster saw an opportunity to expand with cheap inventory from pandemic disruption (commercial real estate, restaurants, etc.)

Pitching at Remote Demo Day, raising via Jason’s Syndicate

” (Regarding Jason’s Syndicate), the money is actually secondary to the quality of the network.”

Hank Leber
  • Self-funded for 3.5 years while they figured out the business
    • Took ~3 years to build a solid base and infrastructure, and now they are seeing rapid growth
  • Yuri (Hank’s Co-Founder) told him to go try and land Jason Calacanis as an investor, so Hank started reaching out to mutual contacts and eventually got a slot in a Remote Demo Day session over the summer
  • Remote Demo Day format:
    • Seven founders pitch thousands of investors over Zoom
    • Pitches are three minutes each, with a two minute Q&A with judges after
    • After all pitches are finished, the judges vote on their top three and the audience members (accredited investors) vote for their #1 company in a poll
    • One day later, all 7000+ members of Jason’s Syndicate get an email with the recording and a sheet where they can pre-commit a dollar amount to invest
    • Any companies that receive over $200K in interest are syndicated!
  • Giggster was The Syndicate’s largest investment ever
    • According to Hank, the quality of the network of investors created additional value beyond the capital invested

Giggster’s use cases and emerging content business models

  • Giggster collects 15% from the final host payout as a service fee
  • Daily rates for a shoot range $2-30K per day depending on how high-end the location is
    • the average is around $8-10K
    • Larger long-term deals will hit 7 figures
      • example: ABC renting a mansion for The Bachelor for three months
  • Production came back online quickly during the pandemic, the film industry was really aggressive and inventive about their protocols
    • Even in an industry resistant to change, all of the money drying up overnight caused people to change their minds FAST
  • Giggster holds production companies accountable and cares a lot about reputation.
    • Location marketplaces need to maintain a good relationship with cities & neighborhoods so they can continue to operate
    • Typically the professional production companies have outstanding reputations for taking care of properties, however, a new potential business model is more uncertain…

TikTok content houses are a new media business model

  • Sway & Hypehouse are the most famous TikTok houses
    • These are new media operations that have very different needs and filming styles than traditional production.
    • They don’t have big camera crews but are also notoriously crazier than a film studio.
    • It’s not cut and dry how to service these creators yet, so that’s where Giggster is attacking the opportunity:
      • They are working to pick the right locations (areas with more space and fewer neighbors), and figuring out the insurance needs to service these new smaller-scale customers

Scaling Giggster

  • The importance of network relationships and trust is key for B2B. Cold emails work worse in this category.
  • Since Giggster has been operating successfully before raising money, they know their unit economics and are comfortable putting together an aggressive growth plan

” [once] you get dollars in the door and deliver real value with product-market fit, adding money to scale is a math equation instead of trying to paint a picture and tricking people into buying your vision of the future.”

Hank Leber

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Joanne Wilson’s Top Insights | Angel S5 E10

Top Insights

  • Raising at a juiced valuation can have devastating downstream consequences for a startup.
  • Recent momentum in funding underestimated founders has helped firms realize the opportunity of having a diverse team of investors.
  • It is harder than ever to be a “generalist” investor. To succeed in today’s market you need a thesis.
  • Portfolio management near the peak is key to thriving in a down market.

Background / Intro

  • Joanne Wilson is a blogger, businesswoman and angel investor with 130+ investments.
    • She mostly invests in women and underestimated founders.
  • Back in the 1990’s, Joanne was Jason’s top sales executive at Silicon Alley Reporter and taught him a very important lesson: sales solves everything. “If you have a great person who can sell, everything goes in the right direction.” – Jason Calacanis

Spotting a bubble, impact of juiced valuations on startups

“… we’ve seen it so many times over the past 20 years. (Founders) end up with a down round even though (they’ve) done a good job.”

“(After raising a down round) that company is damaged. And then institutional investors have moved on into something new and something else and you’re f****d.”

Joanne Wilson
  • How raising during a bubble can create downstream issues:
    • Founders raise at an inflated valuation, and then have to put up crazy numbers to justify a higher valuation in their next round of funding
    • So, even really good companies can “get ahead of their skis” and fail to justify their mid-bubble valuations
    • If a company then raises a down round, that puts a black mark on their resume that is hard to erase, especially if VC money starts drying up
      • or, as Joanne puts it: “You’re f****d.”
  • There is a direct correlation between media sales and the strength of the overall economy
    • According to Joanne, you can check the thickness of each issue of her four decade Vogue collection to see how the economy was doing that year
  • Ad-based companies should bank as much revenue as possible (and even create new inventory if necessary), because high demand won’t last forever

Positive changes to diversity in venture capital over the past 15 years

“There is a whole group of amazing black founders that no one who is a white investor has ever seen. It was the same thing when I started investing in women, there were all these amazing women out there but no one wanted to meet them…” – Joanne Wilson

  • More women and people of color are starting companies and becoming venture capitalists, so the industry is being changed from both sides
  • It’s been 15 years in the making, but the venture industry is finally starting to see real change with funding dollars moving in the right direction
  • Seeing a team page with a bunch of white males on it is an immediate red flag for some investors
  • Investors are funding and hiring people of color for different reasons:
    • some are doing it because they care about making real change
    • others are ashamed at the lack of diversity in their portfolio and on their team
      • both reasons are helping drive change

Difficulty of being a “generalist” investor in 2021, portfolio management in a bubble

“…as an angel you need to take money off the table when it has gotten silly.”

Joanne Wilson
  • Being a generalist investor was great 15 years ago when there were fewer startups overall
  • To be a generalist investor in 2021 you need a team of people around you for market research, diligence, etc. since there are so many startups doing similar things
  • Portfolio management in a bubble:
    • Some greener VCs have never seen a down market
    • Selling a percentage of your winners at or near the peak is a great way to hedge against a rapid downturn
    • For example, Joanne’s husband Fred Wilson lived through this during the dot-com crash of 2000

Watch/Listen to the full episode:

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

Top Insights

“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 app to come in and usurp them. And I fundamentally believe that’s what Snack is doing with a video-first approach.” – Kimberly Kaplan

  • Snack was created to optimize a single dating platform for Gen Z
    • What was the problem?
      • Users, especially Gen Z, would match on Bumble or Tinder and immediately move the conversation & interaction to other apps like Snap & Instagram
      • On those platforms, users would reply to each others’ stories and casually flirt, rather than carrying on in a more high-pressure DM conversation on the dating apps
  • Learning different lessons from different properties:
    • Tinder: design-driven
    • Match: marketing-driven
    • Plenty of Fish: data-driven”Match has done a phenomenal job at working with different companies and acquiring different companies.” – Kimberly Kaplan
  • 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 startups’ success easier.

Ask Jason

From TWiST Slack member Alan from (

Aside from a PR news wire or DIY PR methods, how else can a company with over $1M in revenue let people in VC know about us?

Jason’s Answer:

  • Celebrate your wins, write a short blog post when you hit milestones (300-500 words).
  • Content Marketing on Twitter, LinkedIn (social media), start following VCs and engage with them. Host conversations where you can share your expertise.
  • Run targeted promotions of your best blog posts to VCs and like-minded individuals.
  • Send monthly updates to non-investors.

From Jacob:

As a new investor – what key metric would you look for in these 3 different types of startups: consumer subscriptions, marketplaces, b2b saas?

  • Consumer Subscriptions (Calm, Netflix, Spotify)
    • What is the user profile of your top users, and what is the retention and churn like for those top-tier users?
    • Customer acquisition cost
  • Marketplaces (UberEats, Doordash, Zillow)
    • Frequency of use (transactions per customer)
  • Bottom-up Enterprise SaaS
    • Land-and-expand, or net dollar retention (NDR)
    • NDR measures impact on revenue generation from existing customers
    • If your net dollar retention is over 100%…
      • It means your startup will grow revenue only from its existing customer base, without needing to acquire any new customers
      • It also means you have achieved net negative churn:
        • which is when revenue gained from existing accounts exceeds revenue lost from churned accounts – (see David Sacks on churn)
        • an example would be: more existing Slack customers expand from free to paid accounts then churn or downgrade from paid to free
        • According to David Sacks, the master of bottom-up SaaS, this is a great signal for your B2B company

Kimberly Kaplan

  • CEO & Co-Founder, The Snack App (Nov 2019-Present), launched in 2021
  • Website:
  • Funding
  • Formerly worked at Plenty of Fish (2009-2018)
    • Started as VP Marketing & Advertising (3rd person at company)
    • Became VP Product Management, Revenue Optimization & Marketing
    • Grew Daily Active Users (DAUs) from 1M to over 4M and Annual Recurring Revenue (ARR) from $10M to over $100M
    • sold to Match Group for $575M in 2015

The Snack App

“You shouldn’t have to date across two platforms. That’s why we built Snack to pull the best of the two together.” -Kim Kaplan

  • A video-first dating app that asks users to create a video and post it to a feed.
  • Users can scroll through a feed (like Instagram) and when someone likes a video, it opens up the ability to comment.
  • Once two users have liked each others’ videos, DMs are open.
  • She reached out to a Gen Z focus group to name the app and come up with the logo. Snack is a Gen Z term for cute/attractive.
  • Snack is not a static app where you update 5 photos. Snack has more dynamic profiles to show off and interact.

How Kim got the idea

  • Saw that people were trying to date on TikTok (making a video with bio about themselves), 13B views of #single on TikTok
  • Users, especially Gen Z, would match on Bumble or Tinder and immediately move the conversation & interaction to other social media like Snap & Instagram
  • On social, users would reply to each others’ stories and more casually flirt, rather than carrying on in a more high-pressure DM conversation on the dating apps

Dynamics of modern Dating Apps

  • Snack app is breaking out the gender categories to better reflect society.
  • Snack is looking more toward social media instead of what the legacy dating apps are doing.
  • Most dating apps are now using a freemium model where people can pay more to get more features or matches.
  • is the dominant company in the dating apps space:
    • 10.9M average subscribers
    • $2.4B in revenue
    • Brands include: Tinder, Hinge, Match, Meetic, Pairs, BLK, Plenty of Fish, OurTime, Upward, and Chispa
  • Bumble has been a strong competitor and allowed more investor confidence for dating apps challenging Match’s dominance.
  • Kim learned from each different portfolio company in
    • Tinder: design-driven
    • Match: marketing-driven
    • Plenty of Fish: data-driven
  • Facebook is a massive channel for dating app acquisition
  • Apple is stingy about dating app approvals, Kim had to pull strings to get it approved. Apple has a high quality bar for these apps.

Startup vs. Large company

  • In the early days of Plenty of Fish “we could sit around a table and drink wine in the afternoon because there were only 6 of us.”
  • There are clear changes in how an organization feels at 30, 60 and 90 employees.

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