

This Week in Startups
Jason Calacanis
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Episodes
Mentioned books

Feb 28, 2023 • 58min
ANGEL: Canaan’s Maha Ibrahim on fund sizing, distribution strategies & early VC days | E1687
Maha Ibrahim of Canaan joins Molly to discuss her early days in VC (1:38), managing distributions and exiting at the right time (20:36), the clean tech bubble, being a generalist/specialist, diversity, and more (37:42).
(0:00) Molly kicks off the show
(1:38) Maha’s first years in venture
(11:18) LinkedIn Jobs - Go to https://linkedIn.com/angel and post your first job for free.
(12:43) Investing in the early 2000s and Canaan’s strategy
(19:12) Cast.ai - Get a free cloud cost audit with a personal consultation at https://cast.ai/twist
(20:36) Exiting at the right time and distributing earnings
(30:00) Learning from a downturn
(34:58) The mismatch between VCs to outlier startups
(36:11) Prenuvo - Get $300 off at http://prenuvo.com/twist
(37:42) The climate tech bubble
(40:14) Generalists vs. specialists
(42:16) Responding to cycles and signs of good timing
(48:53) Structuring a generational off-ramp
(51:39) All Raise
(55:30) What does the future hold?
FOLLOW Maha: https://twitter.com/mahaibrahim
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 27, 2023 • 57min
Neeva CEO Sridhar Ramaswamy on AI chatbots and the search revolution | E1686
Neeva CEO Sridhar Ramaswamy joins Molly to talk all things search and AI chatbots, including Neeva’s technology and the difficulty of building a search engine (1:41), Neeva’s consumer focus and business model (20:00), and the search-to-answer revolution (41:31).
(0:00) Molly kicks off the show
(1:41) Neeva’s Purpose
(5:06) The technological underpinning of Neeva
(8:00) The hurdles building Neeva
(10:26) Microsoft for Startups Founders Hub - Apply in 5 minutes for six figures in discounts at http://aka.ms/thisweekinstartups
(11:53) The problems search aims to solve
(18:31) LinkedIn Marketing - Get a $100 LinkedIn ad credit at https://linkedin.com/thisweekinstartups
(20:00) Why choose Neeva
(24:01) Neeva’s business model
(29:18) Moving from search to answers + citing sources
(35:53) The ad supported publishing ecosystem
(37:58) Pilot - Get 20% off the first 6 months at https://pilot.com/twist
(39:13) Leaving Google
(41:31) The search to answers revolution
(44:34) Compensating publishers and dealing with content moderation
(48:51) Open loop vs. Closed loop
(54:29) Neeva copycats
FOLLOW Sridhar: https://twitter.com/ramaswmysridhar
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 24, 2023 • 1h 26min
WallStreetBets founder on why he's suing Reddit; Andrew Hart of Hyper; and Ok Boomer | E1685
The Friday variety show is back! Jason kicks it off by interviewing WallStreetBets founder Jaime Rogozinski, who's currently suing Reddit (2:08). Then, Molly is joined by Hyper CEO Andrew Hart to discuss the augmented reality market and Hyper's store-mapping technology (30:16). Producer Rachel wraps the show with content creator Humphrey Yang breaking down his creative process, what he considers valuable metrics, and so much more (53:40).
(0:00) Molly kicks off the show
(2:08) WSB milestones and arbitrage
(12:07) Contra - Get $500 off your first hire at https://contra.com/twist
(13:36) How Reddit works + the WSB controversy
(23:42) Embroker - Use code TWIST to get an extra 10% off insurance at https://Embroker.com/twist
(24:45) Jaime’s ideal solution
(30:16) Andrew Hart of Hyper
(33:57) Creating the ultimate user experience
(39:19) Retreat - head to http://planretreat.com/twistto help you plan the offsite your team deserves!
(40:43) Mapping store and onboarding customers
(45:55) Hyper’s development and future opportunities
(53:40) Ok Boomer with Humphrey Yang
FOLLOW Jaime: https://twitter.com/wallstreetbets
FOLLOW Andrew: https://twitter.com/AndrewHartAR
FOLLOW Humphrey: https://twitter.com/Humphreytalks
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 23, 2023 • 1h 13min
Sophia Amoruso on branding, raising a fund, portfolio construction & more | E1684
Sophia Amoruso, Founder and GP at Trust Fund, joins Jason to discuss her angel investments (1:23), raising a fund publicly (5:54), and the creative process (12:14). Then, they discuss portfolio construction and putting past identities to bed (27:04).
(0:00) Molly kicks off the show
(1:23) Previous angel investing experience
(5:54) Why Sophia is raising a public fund
(10:45) Linode - Apply to Linode's Rise program for up to six figures in discounts at https://linode.com/twist
(12:14) Branding and the creative process
(20:55) Lemon.io - Get 15% off your first 4 weeks of developer time at https://Lemon.io/twist
(22:25) What stage of investing is Sophia going after
(27:04) Portfolio construction
(37:16) Brilliant.org - Go to http://brilliant.org/twist to start your 30-day free trial today and get 20% off your annual premium plan
(38:44) Pro rata rights
(46:56) Putting past identities to bed
(1:01:18) Fund cycles
(1:05:17) Investing in founders or investing in ideas & more
FOLLOW Sophia: https://twitter.com/sophiaamoruso
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 22, 2023 • 1h 8min
ANGEL: Upfront’s Mark Suster on the power of alignment, setting reality, and raising capital | E1683
Jason is joined by Mark Suster of Upfront Ventures to cover raising capital in the early 2000s (1:22), aligning board members (21:19), the three variables VCs need to bet on (40:51), and so much more!
(0:00) Molly kicks off the show
(1:22) A recap of the previous 3 market cycles
(5:23) The hurdles founders will face starting a company in 2023
(6:55) Raising capital in the early 2000s
(9:15) LinkedIn Jobs - Go to https://linkedIn.com/angel and post your first job for free.
(10:37) Upfront’s strategy and changes to the market
(15:35) Misalignment of investors
(19:48) Prenuvo - Get $300 off a full-body MRI scan at https://prenuvo.com/twist
(21:19) Aligning of board members
(29:13) Setting reality as an investor/board member
(33:40) Cutting Burn & Mark’s decision framework
(39:23) Orgspace - Get $2000 of credits on pro plans with a 30-day free trial at https://orgspace.io/twist
(40:51) The 3 variables VCs need to bet on
(48:28) The power law and mission-aligned founders
(52:13) Feed the family money
(58:33) Company killers + Investing in lines not dots
FOLLOW Mark: https://twitter.com/msuster
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 21, 2023 • 54min
Brain-computer interfaces and the future of neural engineering with Dr. Benjamin Rapoport | E1682
Precision Neuroscience’s Co-Founder and Chief Science Officer joins Molly to discuss how the brain communicates with the body (7:08) and the breakthroughs that allowed companies like Precision to exist. (12:52) Then, they discuss Precision’s founding principles, the process of getting FDA approval for its neural interface, and much more. (28:55)
(0:00) Molly kicks off the show
(1:27) Dr. Rapoport’s origin story
(7:08) How the brain communicates with the body
(11:22) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST
(12:52) Breakthroughs in neuroscience
(22:37) Contra - a commission-free marketplace for freelancers and independent creators. Get $500 off your first hire at https://contra.com/twist
(24:06) The tension between public and private institutions
(28:55) The founding principles of Precision Neuroscience
(33:21) The Layer 7 interface and preparing for FDA approval
(40:39) LMNT - Get a free sample pack with any purchase at https://DrinkLMNT.com/TWIST
(42:07) Minimizing risk
(45:25) Interfacing with different areas of the brain
(47:06) Medical infrastructure and the business model of med-tech
CHECK OUT Precision Neuroscience: https://precisionneuro.io
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 21, 2023 • 1h 11min
Meta's paid tier, Bing's chatbot gone wild, Stripe's $4B bill | E1681
First up, J+M break down Meta taking a note from Twitter with a $12 paid tier and how it can have a material impact on revenue. (12:05) Then, they cover the problems with Bing's new chatbot (32:13) before wrapping on Stripe potentially missing its window (46:14) and Meta copying a Telegram feature! (1:00:30)
(0:00) J+M tee up today's topics!
(2:22) Proper PTO operating standards, what's in store for the next few weeks on TWiST!
(10:31) MasterClass - Get 15% off an annual membership at https://masterclass.com/startups
(12:05) Zuck announces Meta Verified, a $12/month paid service for Facebook/Instagram and WhatsApp
(18:56) How Meta's new product can have a material impact on revenue
(21:49) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist
(22:47) What enticing features major social platforms can add to get more paid users
(30:42) Contra - Get $500 off your first hire at https://contra.com/twist
(32:13) Bing's new chatbot has already been toned down by Microsoft for responding with a style the company did not intend
(46:14) Stripe's $4B tax bill and further valuation cuts: did the highest-flying startup fumble the bag?
(1:00:30) Meta also copied Telegram's broadcast channels feature, which Zuck used to announce Meta's new paid tier!
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
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Feb 17, 2023 • 1h 24min
US crypto crackdown with Vinny Lingham & Sunny Madra + OK Boomer | E1680
Vinny and Sunny join Jason and Molly for another crypto roundtable discussing the federal government’s crackdown on crypto. (1:39) They define what staking is (10:13), and Jason addresses his Twitter Exchange with Coinbase founder and CEO Brian Armstrong. (32:20) Then Producer Rachel is joined by Prince Ghosh of Factored Quality for another edition of Ok Boomer. (1:06:45)
(0:00) Molly kicks off the show
(1:39) Crypto crackdown + the roles of the SEC and CFTC
(8:46) Microsoft for Startups Founders Hub - Apply in 5 minutes for six figures in discounts at http://aka.ms/thisweekinstartups
(10:13) Definitions of “staking”
(21:30) Merge - Integrate up to 5 customers for free today at https://merge.dev/twist
(23:00) Using Web 3.0 for crowdsource capital
(32:20) Brian Armstrong and Jason’s exchange + Challenges of crypto exchanges
(40:25) Pilot.com. - Go to https://pilot.com/twist for 20% off your first 6 months of Pilot Core.
(41:54) Regulating stablecoins
(57:41)$100M New Jersey Deli + Jason’s grand plan for TikTok
(1:06:45) Ok Boomer with Prince Ghosh of Factored Quality
FOLLOW Vinny: https://twitter.com/vinnylingham
FOLLOW Sunny: https://twitter.com/sundeep
FOLLOW Prince: https://twitter.com/princeghosh97
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 15, 2023 • 1h 1min
ANGEL: Insight's Deven Parekh on venture tourists, cleaning cap tables & winning investments | E1679
Deven Parekh of Insight Partners joins Jason to discuss navigating markets during the dot com era and the pandemic. (1:50) Then they discuss "venture tourists" and cleaning up cap tables before wrapping up with a look back at some of Deven's winning investments. (20:04)
(0:00) Jason kicks off the show
(1:50) Experiencing the dot com burst
(10:14) LinkedIn Jobs - Go to https://linkedIn.com/angel and post your first job for free.
(11:36) Comparing Web 3.0 and the dot com era + navigating the markets during the pandemic
(18:40) Cast.ai - Get a free cloud cost audit with a personal consultation at https://cast.ai/twist
(20:04) Venture Tourists
(29:30) Unfavorable preference stacks
(37:07) Acquire.com - Sign up for FREE at https://try.acquire.com/twist
(38:32) Cleaning a cap table
(47:57) Looking back at Deven’s investments
FOLLOW Deven: https://twitter.com/djparekh
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood

Feb 14, 2023 • 1h 14min
Bing dodges $100B bullet & IVP's Tom Loverro on the looming startup collapse | E1678
Molly is joined by Rachel as they discuss the news that some companies are selling data about their mental health patients. (1:33) Then they discuss how Bing’s AI chatbot was presenting false information during its reveal last week. (11:57) To wrap, Tom Loverro joins Jason to talk about his viral tweet thread about a “mass extinction event coming for early & mid-stage companies”. (24:36)
(0:00) Molly and Rachel kick off the show
(1:33) America’s mental health data is being sold
(10:28) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST
(11:57) Bing dodges $100B bullet
(20:23) House of Macadamias - Get 20% off at https://houseofmacadamias.com/twist by using code TWIST20
(21:51) Molly and Rachel’s AI predictions
(24:36) IVP’s Tom Loverro joins Jason
(39:32) Fitbod - Get 25% off at https://fitbod.me/twist
(40:42) Tom’s prescriptions for founders
FOLLOW Tom: https://twitter.com/tomloverro
FOLLOW Rachel: https://twitter.com/_rachelbraun
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood


