This Week in Startups

Latest Episodes:

Peloton's new CEO + Cake Ventures' Monique Woodard Angel S6 E5 | E1383 Feb 11, 2022

Show notes

In the opening news segment, Molly and Jason break down the news around Peloton's new CEO, Barry McCarthy, including the open letter he sent to the company, his background and principles for success (2:05).

Then, Monique Woodard of Cake Ventures joins for Episode 5 of Season 6 of Angel (32:50). Monique was a founder, startup community leader, VC scout, and VC partner before raising her first fund.

In this episode you will learn:

Her thesis on investing in demographic change
What fundraising is like as a founder vs. fundraising as an aspiring fund manager
Why she chose to have multiple closes for her fund
Why Monique focused her efforts on institutional LPs, even though they take longer to close than individual LPs
What it takes to operate as a solo GP

(0:00) Jason and Molly tee up today's topics: Breaking down Peloton's new CEO background and leadership style and an amazing interview with Monique Woodard (Cake Ventures)

(2:05 ) Understanding Peloton's new CEO and the value of its user base

(12:47) LinkedIn - Post your first job for free at https://linkedIn.com/angel

(14:15) Some more fun with numbers, plus breaking down Barry McCarthy's introduction email to all Peloton employees

(21:43) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist

(22:54) Finalizing McCarthy's "principles of success" list and reflecting on the difficulty of a turnaround

(31:32) Embroker - Get an extra 10% off insurance for your business at https://Embroker.com/twist

(32:50) Introducing Cake Ventures' Founder & Partner Monique Woodard: Understanding Cake's thesis on investing in demographic change

(42:20) Fundraising as a founder vs. fundraising as an aspiring fund manager, understanding how different types of LPs invest

(50:58) Check sizes differences from institutional LPs and individual LPs, understanding multiple fund closes

(1:07:18) Managing deal flow as a first-time fund manager, is the industry becoming more welcoming to underrepresented fund managers?

Check out Cake Ventures: https://cake.vc/

FOLLOW Monique: https://twitter.com/MoniqueWoodard

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

$3.6B crypto hack recovered + Segment co-founder Peter Reinhardt's next bet: Charm Industrial | E1382 Feb 10, 2022

Show notes

We have a great interview with a serial-founder today! But first, Molly and Jason cover one of the craziest stories of the year. A couple has been charged with conspiring to launder ~$3.6B worth of crypto from the 2016 Bitfinex hack. Ilya is a former YC founder and Heather part-time rapper.

Today's Guest is Peter Reinhardt, the co-founder of Segment, a customer data platform that sold to Twillio for $3.2B. Peter discusses his new company, Charm Industrial, which is focused on carbon capture and removal. You will learn:

1. How they turn agricultural waste and biomass into a high-carbon fuel

2. The carbon-removal benefits of injecting the bio-fuel into old oil wells

3. Why carbon capture is an important piece of getting to Net Zero

4. The potential impact of Charm Industrial if it succeeds (total CO2 tonnage)

5. Why this process differs from more passive ways of carbon offsets

6. How he landed customers like Shopify & Stripe (and why he thinks companies will continue to do this, even without government regulation)

0:00 Jason and Molly tee up today's topics: a MAJOR crypto scandal and an amazing interview! 2:14 Breaking down the $3.6B Bitcoin seizure federal investigators 13:39 Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout! 14:56 Explaining how the laundering happened mechanically 18:21 Jason's prior emails re: the YC founders' company, jumping to BAYC "doxxing" story 24:25 Vanta - Get get $1,000 off automating your SOC 2 at https://vanta.com/twist 25:44 The most amazing part of this story: Razzlekhan the rapper, and Ilya the s***poster; plus Jason and Molly cast the docu-series for this disaster 33:12 Fiverr - Sign up for https://Fiverr.com/Business free for the first year and save 10% on your purchase with promo code JASON 34:34 Crypto brigading, crypto's impact on the environment 42:00 Charm Industrial's Peter Reinhardt (formerly of Segment) speaks about Segment selling to Twilio for $3B+ 51:38 Charm Industrial's origin story, understanding industrial de-carbonization and carbon removal 1:05:11 1 TAM for carbon removal companies, breaking down the 4 quadrants of fighting climate change

Check out Charm Industrial: https://www.charmindustrial.com

FOLLOW Peter: https://twitter.com/reinpk FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Peter Thiel departs FB board, John Foley steps down at Peloton, Should Amazon spin off AWS? + Startup of the Day: Island | E1381 Feb 09, 2022

Show notes

Molly and Jason cover Peter Thiel stepping down from FB's board and look back at the board's evolution over time (2:07). Next, we cover Joe Lonsdale's op-ed in the Wall Street Journal, where he argues AWS should be split off from Amazon (27:41). We debate if valuations would increase if separated. Then, Peloton Founder & CEO John Foley is stepping down as the firm lays off 2800 people (40:30). We debate if they angling for an acquisition or making a turnaround attempt. To wrap, we discuss our startup of the day, Island, which is a browser for enterprise with a big valuation for a pre-product company (50:11). 00:00 Jason and Molly tee up today's topics 02:07 Peter Thiel is stepping down from Meta's board after almost 17 years of service 11:48 Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST 13:12 Thiel maximizing political influence, Marc Andreessen's shadow advice to Zuckerberg, other $FB board squabbles 24:32 Marlow - Get 15% off your individual or team memberships at https://getmarlow.com/twist. 25:47 Reed Hastings testy email to Peter Thiel in 2016 (while they were both $FB board members) 27:41 Joe Lonsdale's case for splitting AWS away from Amazon's retail business 39:08 Indochino - Get $50 off any purchase of $399 or more by using code TWIST at checkout https://indochino.com 40:30 Peloton CEO John Foley steps down as the company lays off ~2800 employees (20% of its corporate workforce) 50:11 Startup of the Day: Island.io — enterprise browsers in the cloud: valuation vs. traction, founder, market, and more

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Spotify's saga continues, $FB warns of EU exit, GoFundMe's protest refund, Peloton's suitors | E1380 Feb 08, 2022

Show notes

Molly and Jason catch up on the big news stories from the weekend. First, we talk about the Joe Rogan & Spotify saga (1:51) and size up the odds of Rogan finishing out his contract with Spotify (15:41). Then, we cover Facebook warning about pulling Instagram and Facebook out of Europe due to privacy regulations (29:54). Next, we cover GoFundMe's decision to pull funding for the "Freedom Convoy" protesters in Canada. We wrap with a discussion of the WSJ's reporting that Amazon is considering acquiring Peloton (57:26).

0:00 Jason and Molly intro today's topics! 1:51 Daniel Ek's comments on the newest Joe Rogan controversy: Is Spotify a publisher? Why or why not? 14:26 Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist 15:41 Jason predicts the endgame for Joe Rogan and Spotify, Molly and Jason break down the odds of Rogan finishing out his contract with Spotify 27:45 Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist 29:03 Wrapping on Rogan/Spotify 29:54 $FB warns the SEC and shareholders they could pull out of Europe pending new privacy laws, how Meta could win over public sentiment 39:29 Superside - Go to https://superside.com/twist to get $3000 or more in credits when you sign up for an annual subscription 40:51 Meta's need for a "coalition," does $FB need new leadership? Plus, Jason fixes Meta's PR mess 45:52 GoFundMe's controversial decision re: Canadian truckers "Freedom Convoy" 57:26 Amazon rumored to be looking at a potential Peloton acquisition, Jason takes credit for a hot take

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

John Doerr of Kleiner Perkins with Ryan Panchadsaram + VC Sunday School: cap table management | E1379 Feb 06, 2022

Show notes

John Doerr of Kleiner Perkins joins to discuss his lessons from a career of investing and his new book "Speed & Scale: An Action Plan for Solving Our Climate Crisis Now," alongside his co-author Ryan Panchadsaram.

But first, Jason gives a 10-minute crash course on how to navigate messy cap tables in our latest VC Sunday School segment (1:54).

Then John and Ryan join Molly and Jason for a conversation (15:11). In this episode, you will learn:

1. The six objectives and four accelerants to reach zero emissions by 2050

2. Why Nuclear power is an important part of the plan, but cannot be the only solution

3. The biggest blockers to rapid climate progress and why "the climate crisis is under-hyped"

4. Hard-won lessons from funding solar companies

5. How John assesses founders and develops conviction to invest

6. Indications John saw that Jeff Bezos was an exceptional entrepreneur

7. Where investors should focus to drive the biggest output

(0:00) Jason and Molly intro the show, John Doerr, saving the climate and cap tables (01:54) VC Sunday School - When is a Cap table too messy? (07:29) Why VCs want founders to maintain more than 50% equity in the seed round (10:02) Odoo - Get your first app free and a $1000 credit at https://odoo.com/twist (11:08) What are the metrics for a red flag? (15:11) Interview - John Doerr and Ryan Panchadsaram, on the path to zero emissions (20:44) Bubble. Get one month free of a no-code plan at https://bubble.io/twist (22:17) Six objectives to reach zero emissions (30:22) The four accelerants needed to cut emissions in half by 2030 and hit the target by 2050 (31:28) Revelo - Get 20% off the first 3 months by mentioning TWIST at https://revelo.io/twist (32:56) Where investors can focus to drive the biggest change, why the time for "individual action has passed" and we need collective action (35:22) Why Nuclear power is an important part of the plan, but will not be deployed in time (42:06) Identifying the biggest blockers to rapid progress (47:37) Lessons from funding solar companies, why they require more capital and more intellectual rigor (51:32) How Kleiner's early climate investment portfolio performed (54:40) How Jason came to own the Roadster that KP Partner Ray Lane had ordered (56:29) How Kleiner invests in Beyond Meat (58:16) How John assesses founders and develops conviction to invest (1:03:52) John spending time with Jeff Bezos, how Jeff actually knew how to pull his own revenue numbers with a UNIX grep command (1:07:49) Why John thinks the Climate Crisis is under-hyped (1:16:13) Where should investors focus?

Read Speed & Scale: https://speedandscale.com

FOLLOW John: https://twitter.com/johndoerr FOLLOW Ryan: https://twitter.com/rypan FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

NYC delivery wars, Cruise gives driverless rides in SF + Gopuff Co-CEO Rafael Ilishayev | E1378 Feb 04, 2022

Show notes

First Jason and Molly discuss reports from "The Information" that Jokr is looking to sell its NYC delivery business due to heightened competition (1:51). Next, they cover how Cruise is opening up its driverless vehicles to give rides in San Francisco (11:09).

Then, Gopuff Co-founder and Co-CEO Rafael Ilishayev joins to discuss his rapid delivery business (19:12).

Almost a decade ago, Raf and his co-founder Yakir Gola started one of the fastest-growing commerce businesses while in college. Most recently they raised $1B at a reported $15B valuation in July 2021. In this episode, you will learn:

1. The rationale behind operating a vertically-integrated model

2. How they operate hundreds of micro-fulfillment centers & manage deliveries in 20 minutes

3. Why they acquired BevMo and Liquor Barn to accelerate their alcohol delivery business instead of building it themselves

4. The challenges he sees going forward to operate the business well

5. Why Gopuff launched their own private label called "Basically" and hot food offering called "Gopuff Kitchens"

6. How influencers like Mr. Beast are choosing Gopuff as a key platform to distribute products

Check out Gopuff: https://www.gopuff.com

FOLLOW Raf: https://twitter.com/Rafaelilishayev FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

(00:00) Molly and Jason intro the show (01:51) The Information reported that Jokr is shopping it's NYC delivery business (09:57) Masterworks - Skip the waitlist to invest in art using promo code TWIST at https://Masterworks.io (11:09) We Live in the Future - Cruise Robotaxis open up for SF public in limited quantities (17:56) Linode - Apply to their Rise program for founder-led, early-stage startups and get 3 years of discounts at https://linode.com/twist. (19:12) Interview Gopuff Co-CEO Rafael Ilishayev (31:41) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist (32:54) Gopuff's focus on the SKUs that matter for their customers (35:10) Can Gopuff operate profitably? (38:41) Managing Gopuff deliveries (43:34) Gopuff's pace of expansion (49:45) Will Gopuff enter the cannabis market? (50:51) What are Gopuff's potential headwinds? (53:27) Why Mr. Beast picked Gopuff as a distribution channel (59:24) How Gopuff picked up talent from the defunct Brandless team to launch their house brand, Basically (61:59) Gopuff's sustainability measures

Full $FB earnings breakdown, NFT company violates music IP + Behind Genius' Paige Finn: Angel S6 E4 | E1377 Feb 04, 2022

Show notes

In the opening news segment, Molly and Jason break down the numbers behind Facebook's colossal drop in market cap (2:42). Then, they cover a company that seems to be violating music copyrights to sell NFTS (38:14).

Then, Paige Finn of Behind Genius joins for Episode 4 of Season 6 of Angel (49:45). Paige became interested in venture capital during college, but within a year and a half of graduating in 2020 she already has a fund!

In this episode you will learn:

1. How she secured her first allocation before having a fund

2. The steps she took to set up an SPV while being a non-accredited investor

3. How she raised a $1.6m fund

4. Behind Genius' investing thesis and strategy

5. The books that have most influenced her work and writing style

6. Why she wrote a picture book (for adults) called "Seed to Harvest: A Simple Explanation of Venture Capital"

00:00 Jason & Molly introduce the show 02:42 Facebook's painful $220B market cap drawdown 07:32 Is blaming Apple 10:29 LinkedIn - Post your first job for free at https://linkedIn.com/twist 11:37 "This is one of the most hardcore hits I've ever seen in business" 14:11 Would Zuckerberg leaving hurt the company even more? 17:33 Do rebrand's ever really work? 20:08 Embroker - Get an extra 10% off insurance for your business at https://Embroker.com/twist 21:29 Could Facebook have been a successful hardware operator? 25:03 Breaking down the numbers around Meta's future business 30:32 Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist 31:51 Is there a solution for Zuckerberg? 36:28 How Jason's divorced friends use Instagram 38:12 NFT site "Hitpiece" accused of trying to sell songs without consulting original artists 49:44 Interview - Paige Finn of Behind Genius 52:02 How Paige learned about VC in 2018 55:28 Behind Genius' investing thesis and strategy 1:00:05 How Paige set up an SPV while being a non-accredited investor 1:10:11 How her book "Seed to Harvest: A Simple Explanation of Venture Capital" helped her gain credibility 1:13:51 Paige's most influential books 1:23:09 Paige's day to day life as an investor 1:33:55 Plugs from the TWIST team

Check out Behind Genius Ventures: https://www.behindgeniusventures.com

FOLLOW Packy: https://twitter.com/paigefinnn

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

All-In's hijacked feed, Google's earnings breakdown, Jason's legendary iPad troll | E1376 Feb 03, 2022

Show notes

First, Jason explains how someone copied the All-In podcast, put in ads, and then redirected Google's podcast player to display it as the real All-In feed (1:44). Then, we break down Google's Q4 and full year earnings for 2021 (18:25). Is Google the best business ever? Then, Jason tells the story of "The Great iPad Troll of 2010" (45:10).

00:00 Jason & Molly intro the show 01:44 How someone hijacked the All-In podcast feed and started serving ads on it 02:18 Funny story about Jason wanting to monetize All-In, and why it's not 03:07 We get sidetracked talking about private jets 07:31 What actually happened with the All-In feed 11:12 Vanta - Get get $1,000 off automating your SOC 2 at https://vanta.com/twist 12:31 Fair use and the growing culture of limited credit on the internet 16:28 Jason gets sidetracked talking about Book of Boba Fett 18:07 Thank you to the fans and Google who sorted it all out 18:25 Google's "Bonkers" earnings 20:18 Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout! 21:35 Google's net income was up 90% year over year 29:46 Gun.io - Get $250 off your first developer hire at https://Gun.io/twist! 31:04 Google's big problem, more money than they know what to do with 45:10 Jason's crazy iPad story from 2010 54:24 A note from the show

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Playstation's $3.2B Bungie acquisition, Metafy gaming tutoring, Shopify CEO joins Coinbase Board of Directors | E1375 Feb 02, 2022

Show notes

Another big news drop in the gaming space! Jason and Molly discuss Sony is acquiring Bungie for $3.6B (2:36). We break down what this means for Sony, Bungie's crazy history, and if other big tech giants should look for M&A targets in gaming. Then, we talk about our startup of the day called Metafy which allows pro gamers to do 1-on-1 teaching, online for hourly rates (29:38). Finally we wrap with Shopify CEO Tobi Lütke joining Coinbase's board (48:33). (00:00) Jason & Molly tee up the topics, Sony's big acquisition, Metafy (02:36) Sony is acquiring Bungie for $3.6B & Bungie history (10:41) Boast - Get your R&D tax credits without the hassle at https://boast.ai/twist (11:58) Other big tech giants should look for M&A targets in gaming (19:46) OpenPhone - Get an extra 20% off any plan for your first 6 months at https://openphone.com/twist (21:27) Current console pricing and Big Tech competition (29:38) Startup of the day - Metafy is company where pro gamers to do 1-on-1 teaching online for hourly rates (32:07) RealGoodFoods - Go to https://realgoodfoods.com and use code TWIST for $15 off! (33:39) Breaking down Metafy's raise and investment terms (42:11) Jason explains how Blayze is another example of pro-coaching for athletic training (48:33) Shopify CEO Tobi Lutke joining Coinbase's board (01:10:11) Learn what's going on at TWIST

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Breaking down Ryan Breslow's YC critique + Spotify's solution & Joe Rogan's response | E1374 Feb 01, 2022

Show notes

Over the weekend Bolt CEO Ryan Breslow wrote a big thread on why he thinks Y Combinator isn't worth it. We break it down point by point and assess the validity of the claims (7:07). Right before we started recording, news broke that Breslow was leaving the CEO role to assume the executive chairman position, so we cover that too (2:11). Then, we cover Joe Rogan's expla-nology (explanation/apology) video regarding his COVID-related interviews that have upset many. We react to his response, Spotify's new COVID policy and reflect on the risks to Spotify's business overall (44:32).

(0:00) Jason and Molly tee up today's topics: Bolt CEO steps down after another spicy thread, Rogan "apologizes" for COVID misinformation (2:11) Bolt CEO Ryan Breslow stepped down as CEO to executive chair: was it really his decision? (7:07) Jason and Molly break down Breslow's thread on YC not being worth it for founders (15:43) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist (17:00) Breslow's YC thread cont.: breaking down Breslow's five beliefs about YC (27:53) Ourcrowd - Check out the deal of the week at https://ourcrowd.com/twist (29:11) YC scaling fundraising and opening access to venture capital to more groups of founders; Breslow's advice on building a network and fundraising (36:03) Marlow - Get 15% off your individual or team memberships at https://getmarlow.com/twist. (37:18) YC alumni have started a blockchain-based DAO called Orange DAO to invest in crypto startups (44:32) Joe Rogan's "apology" video and Spotify's new COVID disclaimer: Molly nails the prediction, has Spotify done a bad job of content moderation so far? (53:42) Breaking down Joe Rogan's explanology (explanation/apology) piece by piece (1:13:17) Jason breaks down the math of Spotify acquiring Joe Rogan for ~$100M and Howard Stern's similar deal with Sirius XM

Ryan's Thread: https://twitter.com/theryanking/status/1487500943511932941

Joe Rogan's Video: https://www.instagram.com/p/CZYQ_nDJi6G/

FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

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