This Week in Startups

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.

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Episodes

E996: Clearbit CEO & Co-founder Alex MacCaw is creating god-mode for marketers with Clearbit X, gives insights on dynamic customer targeting, prioritizing profitability over valuation, GDPR’s adverse effect on Facebook & Google, value of aggregated data & benefits of CEO coaching

0:58 Jason intros Alex MacCaw 2:26 What is Clearbit? 8:53 What are some Clearbit use cases? 12:48 Benefits of cashflow positivity in terms of fundraising 15:39 How Jason felt about Alex Tew’s Calm investor updates 18:59 GDPRs effect on Clearbit and the industry as a whole 27:37 How did Alex go from anti-coaching to benefitting from a CEO coach? 32:49 Alex’s experience finding a CEO coach from Naval Ravikant 34:22 What did Alex learn about company building from his coach? 38:39 Clearbit’s therapy...

Nov 01, 2019•1 hr 2 min

E995: The Next Unicorns: NEXT Trucking CEO & Co-founder Lidia Yan brings trucking into the digital age with her two-sided marketplace, shares insights on finding & focusing on an untapped market, owning & innovating drayage, navigating the trucking industry as a woman & scaling the right team for su

0:55 Jason intros Lidia Yan 5:03 Lidia describes getting into the trucking industry and why NEXT focuses on "drayage" 13:29 How NEXT has revolutionized drayage shipping 18:22 What is a typical shipping broker's take rate 20:54 How does pricing work in the trucking industry? 27:28 How do trucking companies measure their driver's hours? 29:41 Issues within the trucking industry? 35:14 Did trucking lose employees to ride-sharing? 39:20 How NEXT compares to Uber Freight 44:50 Amazon's impact on the ...

Oct 30, 2019•1 hr 1 min

E994: All Turtles CEO Phil Libin shares his state machine that answers all growth questions; Future of Early-Stage VC w/Pete Flint (NFX), Rebecca Lynn (Canvas Ventures), Dave Samuel (Freestyle Capital); plus LAUNCH Scale Partner Talk w/Lever CTO Nate Smith

1:03 Jason intros Phil Libin from LAUNCH Scale 2019 1:51 Phil Libin on "The State Machine that Answers All Growth Questions" 32:40 Jason joins Phil on stage for Q&A 39:56 Jason intros Phil (NFX), Rebecca (Canvas Ventures) & Dave (Freestyle Capital) 41:34 Transitioning from founder to VC 44:08 How to let a founder know when they are headed down the wrong path 47:42 At what stage does a founder have to change their mindset? 49:49 Dave Samuel on Airtable CEO Howie Liu not taking his advice ...

Oct 29, 2019•1 hr 22 min

E993: Superhuman CEO Rahul Vohra shares the formula for his Product-Market Fit Engine; Future of Angel Investing w/Jeff Clavier (Uncork), Ben Ling (Bling), Clara Brenner (Urban Innovation Fund); plus LAUNCH Scale Partner Talk w/Help Scout VP of Sales Tim Thyne

0:48 Jason intros Rahul Vohra 3:21 Rahul gives a talk on building a "Product-Market Fit Engine" 29:42 Rahul takes questions from the LAUNCH Scale audience 37:28 Jason intros the "Future of Angel Investing" panelists: Ben Ling (Bling Capital), Clara Brenner (Urban Innovation Fund) & Jeff Clavier (Uncork Capital) 38:54 Has Silicon Valley reached peak entitlement? 41:44 Is "too much $ chasing too few companies" the new normal in VC 45:47 How important is price & valuation in decision making...

Oct 25, 2019•1 hr 17 min

E992: The Next Unicorns: Expanse CEO & Co-founder Tim Junio reduces exposure to online threats by providing “attack surface visibility”, shares insights into current threats from China & Russia, potential 2020 election tampering, reasons for cybersecurity optimism & more – E8 of 10-ep miniseries

0:50 Jason intros Tim Junio 1:44 Tim explains what Expanse does and how "attack surface inventory" is the first step in their cybersecurity platform 5:20 Tim explains the Dyn cyber attack 13:20 How many Fortune 500 companies have been blackmailed via cyber attack? 19:32 "White-hat" hackers impact on the cybersecurity industry 23:12 Human-made passwords are the weakest link 29:09 History of Russian interference 33:16 Why Gmail is good for cybersecurity 35:11 Tim's experience at the CIA 38:29 What...

Oct 23, 2019•1 hr 37 min

E991: #StartupTuneup with Urban-X: Waste-reducing marketplaces, traffic liability reduction, recreational sharing spaces, firefighter safety software & energy cost saving AI

0:41 Jason intros the #StartupTuneup with Urban-X companies 2:33 David Rodriguez pitches Food for All: food marketplace to reduce waste & help restaurants sell unused food 12:43 Jim Selevan pitches Pi-Lit: innovating transportation thru a wireless lamp system 26:33 Caroline Hansen pitches Hubbster: providing easy access to outdoor games & gear 41:24 Patrick O'Connor pitches 3AM Innovations: safety software for firefighters 50:52 Michael Lee pitches Evolve Energy: SaaS product that helps ...

Oct 22, 2019•1 hr 27 min

E990: SurveyMonkey CEO Zander Lurie on driving growth by listening to customers & employees, importance of a strong & diverse board, direct listings v. IPOs, lessons learned from WeWork; plus LAUNCH Scale Partner Talk featuring Yosiat Gimbernard from Odoo

1:45 Zander’s take on the recent volatility in the public markets 3:38 What are the lessons learned from the WeWork disaster in terms of corporate governance? 6:09 Importance of diversity on BoD 10:18 Where does WeWork go from here, and how will the situation resolve? 12:35 Why Venture investing is so skewed towards growth, and why the best investors focus on gross profitability 14:41 What is SurveyMonkey’s current business, and why did they go into Enterprise SaaS? 19:20 How listening to custom...

Oct 18, 2019•45 min

E989: The Next Unicorns: Culture Amp CEO & Co-founder Didier Elzinga is building an employee analytics platform that keeps workers satisfied & motivated, shares insights on the changing role of culture, what modern employees value & maintaining culture while scaling – E7 of 10-ep miniseries

0:52 Jason intros Culture Amp's Didier Elzinga 2:44 How Didier's prior career in Visual Effects led him to start Culture Amp 8:24 Issues with yearly performance evaluations 14:15 Did Silicon Valley take culture too far? 17:35 What defines good culture? 24:24 Generational differences in workplace culture 28:30 How should companies view the gig economy in terms of culture and compensation? 37:12 How should compensation work in this era? 43:20 Didier demos Culture Amp 58:45 Jason gives Sir Charles ...

Oct 16, 2019•1 hr 19 min

E988: Aileen Lee, Founder & Managing Partner of Cowboy Ventures, pioneered actionable change to diversify tech & VC, shares early days innovating in e-commerce, insights on current funding landscape, dangers of prioritized growth over sustainability, & lessons learned from backing winners like Dolla

0:51 Jason intros Aileen Lee 1:36 Aileen on her time at MIT, early bias against women in math 5:56 What brought Aileen to San Francisco & working at GAP in the early days of the Internet 9:40 Aileen on working for Mary Meeker & what makes her special 10:25 “All companies that leverage technology are not the same.” 13:10 What made WeWork attractive to investors in the early days? 17:54 How the market is skewed to reward growth 22:35 Thoughts on SoftBank increasing valuations 28:24 How Ail...

Oct 15, 2019•54 min

E987: The Next Unicorns: Upgrade CEO & Co-founder Renaud Laplanche is empowering users to better understand credit through his consumer credit platform, announces the Upgrade Card, shares insights on taking LendingClub public & how startups have changed since he started his first company in 2000 – E

0:51 Jason intros Upgrade CEO Renaud Laplanche 2:07 Renaud goes over the idea of his previous startup, LendingClub, and taking it public 9:57 What happened at LendingClub after the IPO? 11:18 What is Upgrade? How did it grow out of LendingClub? 12:40 Are credit scores an outdated metric? 14:11 What is the Upgrade Card? 15:30 Are modern credit card companies sinister in their approach? 24:54 Renaud's thoughts on Crypto 27:40 Where does Upgrade's lending capital come from? 31:22 Are we approaching...

Oct 12, 2019•56 min

E986: StockX Co-founder Josh Luber is building a stock market for things, shares insights on the two cultural shifts that brought sneaker culture mainstream, attracting Mark Wahlberg, Eminem & Steve Aoki to invest along with Google Ventures & Marc Benioff & growing a unicorn out of a sneaker-data si

1:00 Want to work at LAUNCH? gettheseat.com 2:28 Jason intros StockX's Josh Luber 3:14 When did the sneaker crazy start? 6:37 What is StockX? 9:19 What should Jason wear courtside? And why not Kawhi's? 14:13 Most $ Josh has spent on pair of sneakers? What were they? 18:15 What is StockX's take on a standard transaction? 18:44 Meeting Co-founder & Cavaliers owner Dan Gilbert 19:58 Attracting Mark Wahlberg, Eminem, etc. as investors 22:55 Attracting SV firms vs. attracting famous investors? 29...

Oct 11, 2019•1 hr 2 min

E985: #AskJason! Recognizing great founders as an investor, dealing with a lack of updates, raising capital through crowdfunding, the ideal makeup of today’s founder, how Angel Investing has changed since the release of “Angel”, standing out in slow-to-adapt markets

1:00 Jason intros #AskJason and today's questions 1:47 How to differentiate a great founder from an okay one? - Darius 7:40 Dealing with the lack of updates as a syndicate Angel Investor? - Said 15:54 Bomani calls in and asks Jason about raising through crowdfunding 22:20 What will the new ideal makeup of a founder be after recent events (WeWork, JUUL, etc.)? - Patty 28:29 Peter calls in and asks Jason how Angel Investing changed since "Angel" was released 44:43 Alexandra calls in and asks Jason...

Oct 09, 2019•52 min

E984: Vice Ventures Founding Partner Catharine Dockery raised $25M to invest in vices: marijuana, sextech, gambling, alcohol, vaping; shares insights on hacking her way into VC through cold emails & a strong investment thesis, capitalizing on early markets hungry for investment

0:47 Jason intros Catharine Dockery 4:29 How Catharine came up with Vice Ventures 7:00 What was the response when Catharine began raising her first fund? 7:19 What does harm-reduction mean for Vice Ventures? 9:21 Getting Marc Andreessen to invest in her fund 13:32 Strangest emails Catharine has received since starting Vice Ventures 16:01 Investing in cannabis 20:15 Investing in psychedelics 26:33 Investing in gambling 31:16 Who are Catharine's typical LPs? 32:15 Investing in alcohol 39:33 Invest...

Oct 04, 2019•57 min

E983: The Next Unicorns: Zola CEO & Co-founder Shan-Lyn Ma shares insights on growing her all-in-one wedding platform in a $100bn market, adapting to changes in wedding demographics, balancing growth and profitability while keeping her team focused, raising moral standards in tech – E5 of 10-ep mini

0:51 Jason intros Shan-Lyn Ma 3:17 Starting Zola and competing in a crowded space 5:14 Jason and Shan go through LAUNCH President Sam's Wedding Registry live on air 6:30 How Zola's registry and business model work 9:10 How does Zola look at Amazon's wedding lists 14:29 What has changed in wedding demographics, and how does Zola keep up? 21:26 Jason and Shan share thoughts on romantic proposal locations 25:37 How working for Kevin Ryan at Gilt impacted Shan 33:27 Shan's insights on keeping employ...

Oct 04, 2019•1 hr 1 min

E982: Karmic Bikes Founder Hong Quan on creating the “Tesla of E-Bikes” with OSLO, bootstrapping through Kickstarter, lowering costs as a strategy, insights on U.S. resistance to widespread E-Bike adoption, & why this vehicle is the future of transportation, plus Office Hours with Jason!

1:10 Jason intros Hong Quan from Karmic Bikes 2:55 What is the OSLO bike? 4:10 Why are there separate classifications for e-bike laws? 9:15 What does OSLO cost? 12:35 How Karmic bikes are different 14:55 Why e-bikes haven't taken off in the US? 16:52 Is Palo Alto the most bike-friendly city in America? 17:28 Hong shows the OSLO Kickstarter Video 21:45 Why not go the scooter route? 27:34 Hong raps for Jason (yes, really) 33:06 Open Office Hours with Jason 33:18 Jason intros Mark from ZenSports, a...

Oct 01, 2019•45 min

E981: Roy Bahat, Head of Bloomberg Beta, shares the myths of venture capital, the great value of founders turned investors, why VCs reject startups, searing insights on fundraising & valuations, and predictions on the future of enterprise, AI, work & automation @ LAUNCH Accelerator

1:00 Jason Demant intros Roy Bahat 3:14 Roy's thoughts on raising venture capital 4:14 Debunking the myth of pitching VCs 9:24 Two questions VCs ask themselves after hearing a pitch, and how founders can apply them 15:33 The startup paradox 18:04 Does Bloomberg Beta keep up with companies they passed on? 19:51 Selection bias in Silicon Valley 25:32 Why Angel $ from venture-backed founders is so valuable 28:30 Top reasons Roy rejects companies 31:38 Importance of trust founder-investor relationsh...

Sep 27, 2019•1 hr 12 min

E980: The Next Unicorns: Alto Pharmacy CEO & Co-founder Mattieu Gamache-Asselin is working to fix the broken US pharmacy system by removing friction & aligning incentives among patients, doctors & insurers, shares insights on trading short-term profits for long-term success, combating the opioid cri

0:51 Jason intros Mattieu Gamache-Asselin 2:52 Changing from ScriptDash to Alto Pharmacy 4:19 Meeting and working with Twitch founder Justin Kan in the early days of Alto 6:51 Message to HBO’s Silicon Valley writing room 7:26 Working out of Justin Kan’s house 8:15 Why are pharmacies broken? How is Alto fixing them? 14:25 How did Alto’s team architect a 1.0 version of their pharmacy? 21:44 US Healthcare is broken due to bad incentive structures 28:23 Does Alto compare to Hims and Roman? 32:24 Wha...

Sep 25, 2019•1 hr 19 min

FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221

This Week In Startups is made possible by: Goldbelly - Goldbelly.com Every.io - http://every.io/ Zite - zite.com/twist Today’s show: Today, Zapier’s a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started! In a 2016 chat, founder Wade Foster walked JCal through their 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool ...

Jan 01, 1970•1 hr 17 min•Ep. 2221

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