This Week in Startups – Details, episodes & analysis

This Week in Startups is brought to you by…

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Todays show:

Jason and Alex kick off episode 2000! They reflect on TWiST’s origins and early episodes (1:48), highlighting notable guests and memorable moments (22:31). They also share fan messages, and insights from cohosts (46:05), and wrap up celebrating standout moments (1:04:14).

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Timestamps:

(0:00) Jason and Alex kick off the show

(1:48) The origins and early days of TWiST

(9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(11:03) Recollections of the first TWiST episodes

(20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups

(22:31) Highlighting notable guests and memorable early episodes

(30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24

(32:02) More on standout guests and the TWiST studio evolution

(38:37) David Sacks makes his first appearance on TWiST

(46:05) Messages from TWiST fans and cohosts

(1:05:14) Celebrating standout moments and key highlights on the show

(1:28:02) A special message from the Launch team

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Check out the TWIST500: https://www.twist500.com

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Mentioned on the show:

https://www.youtube.com/watch?v=yZX4fUYo6C0&list=PL24nOpPUQlbZcij2Jo-KNUpWFDSrrQKtH

https://www.youtube.com/watch?v=t3bmpMX2qQ4

https://www.youtube.com/watch?v=SP7B0oWTR3o

https://www.youtube.com/watch?v=2cdrCYrZIvI

https://youtu.be/wM0pVE_b1KU?si=NM1pK-pz9tUQFOqr&t=1366

https://www.youtube.com/watch?v=550X5OZVk7Y

https://www.youtube.com/watch?v=6VOQnK7O2To

https://www.youtube.com/watch?v=n1_z9oOdytA

https://www.youtube.com/watch?v=aM1DDVq3_vs

https://www.youtube.com/watch?v=TYA_vdHSD8w

https://www.youtube.com/watch?v=qwhP7K3bFRI

https://www.youtube.com/watch?v=3seTmyRbcHU

https://www.youtube.com/watch?v=ANGHOQ2Cqtc

https://www.youtube.com/watch?v=HL2wWE27CUI

https://www.youtube.com/watch?v=BXEO3oJKINA

https://www.youtube.com/watch?v=43MgbwQBDik

https://www.youtube.com/watch?v=SfJtIibCx78

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Follow Alex:

X: https://x.com/alex

LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm/

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Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Thank you to our partners:

(9:50) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://www.Squarespace.com/TWIST

(20:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at https://www.linkedin.com/thisweekinstartups

(30:33) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/twist24

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

This Week in Startups is brought to you by…

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Google Cloud. Accelerate your startup journey with the Google for Startups Cloud Program. Get up to $200K in Google Cloud credits – or up to $350K for AI startups – plus training and guidance. Apply at https://startups.google.com/twist

Runway. Looking to up-level your financial planning Runway is the modern and intuitive way to model, plan, and align your business for everyone on your team. Sign up at https://runway.com/twist to get your first 3 months free.

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Todays show:

Jason and Kelly kick off the Founder University startup pitch competition (00:00), then we hear from Eric Gilbert-Williams on The Public Bored (4:32), Matt Schwed on Speed AI (11:38), and Joe Tannorella on PodEngine (15:50). Finally, Jason awards a $25K investment, and details how to apply!

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Timestamps:

(0:00) Jason and Kelly kick off the show

(4:32) Eric Gilbert-Williams pitches The Public Bored

(10:24) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.

(11:38) Matt Schwed pitches Speed AI

(15:50) Joe Tannorella pitches PodEngine

(23:33) Google Cloud - Accelerate your startup journey with the Google for Startups Cloud Program. Apply at https://startups.google.com/twist

(25:03) Ranking the three companies

(29:12) Founders' experiences and learning outcomes at Founder University

(31:47) Runway - Sign up at https://runway.com/twist to get your first 3 months free.

(33:18) Q&A

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Founder University: Apply here: ⁠https://www.founder.university⁠

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We are doing Founder Fridays meetups! Visit ⁠https://founderfridays.tech to learn more

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Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com

Check out the TWIST500: https://www.twist500.com

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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

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Follow Eric:

LinkedIn: https://www.linkedin.com/in/eric-gilbert-williams

Check out: https://www.publicbored.com

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Follow Matt:

LinkedIn: https://www.linkedin.com/in/mattshwed

Check out: https://getspeed.ai

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Follow Joe:

X: https://x.com/joetannorella

LinkedIn: https://www.linkedin.com/in/joetannorella

Check out: https://podengine.ai

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Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Thank you to our partners:

(10:24) Fidelity Private Shares℠ - Visit https://fidelityprivateshares.com! Mention our podcast and receive 20% off your first-year paid subscription.

(23:33) Google Cloud - Accelerate your startup journey with the Google for Startups Cloud Program. Apply at https://startups.google.com/twist

(31:47) Runway - Sign up at https://runway.com/twist to get your first 3 months free.

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

This Week in Startups is brought to you by…

Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist

.Tech Domains - Don’t miss our “Jam with JCal” contest! To apply and get more details go to https://jamwithjcal.tech brought to you by .tech domains.

OpenPhone. Create business phone numbers for you and your team that work through an app on your smartphone or desktop. TWiST listeners can get an extra 20% off any plan for your first 6 months at https://www.openphone.com/twist

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Todays show:

Jason and Kelly kick off the Founder University startup pitch competition (00:00). We hear from Pablo on Big Rentals (4:18), Brittany on Where2Wheel (12:28), Ardalan on MyLens (21:31), and Mariano on Prosperous AI (29:07). Finally, Jason awards a $25K investment (38:34), and details how to apply!

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Timestamps:

(0:00) Jason and Kelly kick off the show

(4:18) Pablo Fernandez pitches Big Rentals

(11:37) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist⁠

(12:28) Brittany Peregoff pitches Where2Wheel

(20:10) .Tech Domains - Apply for the Jam Session with JCal contest today at https://jamwithjcal.tech

(21:31) Ardalan Mirshani pitches MyLens

(29:07) Mariano Apodaca pitches Prosperous AI

(35:07) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist

(36:33) Review of the four startups

(40:44) Q&A

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Founder University: Apply here: ⁠https://www.founder.university⁠

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We are doing Founder Fridays meetups! Visit ⁠https://founderfridays.tech to learn more

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Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com/

Check out the TWIST500: https://twist500.com

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Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

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Follow Pablo:

X: https://x.com/directedbypablo

LinkedIn: https://www.linkedin.com/in/pablofernandezorg

Check out: https://BigRentals.com

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Follow Brittany:

X: https://x.com/bperegoff

LinkedIn: https://www.linkedin.com/in/brittany-peregoff-2134092b

Check out: https://where2wheel.com

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Follow Ardalan:

X: https://x.com/ardalanmirshani

LinkedIn: https://www.linkedin.com/in/mirshani

Check out: https://mylens.ai

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Follow Mariano:

LinkedIn: https://www.linkedin.com/in/mariano-apodaca-45b07a16a

Check out: https://prosperousprocess.ai

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Follow Jason:

X: https://twitter.com/Jason

LinkedIn: https://www.linkedin.com/in/jasoncalacanis

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Thank you to our partners:

(11:37) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist⁠

(20:10) .Tech Domains - Apply for the Jam Session with JCal contest today at https://jamwithjcal.tech

(35:07) OpenPhone - Get 20% off your first six months at https://www.openphone.com/twist

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Follow TWiST:

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

Substack: https://twistartups.substack.com

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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916

This Week in Startups is brought to you by…

Gusto is easy online payroll, benefits, and HR built for modern small businesses. Get three months free when you run your first payroll at http://www.gusto.com/twist

*Gusto pricing shown in ad is based on pricing prior to March 2025

LinkedIn Jobs. A business is only as strong as its people, and every hire matters. Go to https://www.linkedin.com/twist to post your first job for free. Terms and conditions apply.

Northwest Registered Agent. Visit - http://www.northwestregisteredagent.com/twist⁠ to get a 60% discount on your next LLC.

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Timestamps:

(0:00) Jason joins seven strong startup pitches from LAUNCH Accelerator.(1:11) Jacqui kicks off the demo day.(1:40) Introductions to the guest jugdes.(4:40) Justin pitches Melengo(10:18) Gusto - Get three months free when you run your first payroll at http://www.gusto.com/twist

(11:32) Edward ptiches PodcastAI(18:09) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist(19:04) Daniel pitches Tolt(24:55) Rae pitches River(27:49) Northwest Registered Agent - Get a 60% discount on your next LLC at - http://www.northwestregisteredagent.com/twist⁠(34:01) Kash pitches TaxGPT(40:56) George pitches Fanfare(46:31) Jam pitches Monic.ai(52:05) Our panel of judges pick their top three pitches.

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Apply to the LAUNCH Accelerator here: https://launchaccelerator.co/

Just getting started? Apply to Founder.University

Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp

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Follow these founders and their companies:

Justin Kwong & Melengo

https://www.melengo.com

https://www.linkedin.com/in/justinckwong/

[email protected]

Edward Brawer & PodcastAI

https://podcastai.com/

https://www.linkedin.com/in/edwardbrawer/

[email protected]

Daniel Gjokaj & Tolt

https://tolt.io/

https://www.linkedin.com/in/danielgj/

[email protected]

Rae Lambert & River

https://app.getriver.io

https://www.linkedin.com/in/raechel-lambert/

[email protected]

Kashif Ali & TaxGPT

https://www.taxgpt.com/

https://www.linkedin.com/in/chkashifali/

[email protected]

George Lam & Fanfarehttps://fanfare.app/

https://www.linkedin.com/in/georgewlam/

[email protected]  Jam Mirzakhalov & Monic.ai

http://monic.ai/

https://www.linkedin.com/in/mirzakhalov/

[email protected]

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Thank you to our judges:

Ben Narasin - Tenacity Venture Capital

https://twitter.com/bnarasin

Blaine Davis - Outlander

https://twitter.com/blainerdavis

Minnie Ingersoll - TenOneTen

https://twitter.com/himinnie

Nicole Seah - Costanoa

https://www.linkedin.com/in/nicole-seah1/

Stella Zhang - Conductive Ventures

https://www.linkedin.com/in/xinxin-stella-zhang/

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Follow Jason:

X: ⁠https://twitter.com/jason⁠

Instagram: ⁠https://www.instagram.com/jason⁠

LinkedIn: ⁠https://www.linkedin.com/in/jasoncalacanis

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Thank you to our partners:

(10:18) Gusto - Get three months free when you run your first payroll at http://www.gusto.com/twist

*Gusto pricing shown in ad is based on pricing prior to March 2025

(18:09) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist

(27:49) Northwest Registered Agent - Get a 60% discount on your next LLC at - http://www.northwestregisteredagent.com/twist⁠

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Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Check out Jason’s suite of newsletters: https://substack.com/@calacanis

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Follow TWiST:

Substack: https://twistartups.substack.com

Twitter: https://twitter.com/TWiStartups

YouTube: https://www.youtube.com/thisweekin

Instagram: https://www.instagram.com/thisweekinstartups

TikTok: https://www.tiktok.com/@thisweekinstartups

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Subscribe to the Founder University Podcast: https://www.founder.university/podcast

NEA's Ben Narasin takes questions from founders: most important content in a pitch deck, COVID's impact on dealmaking, traits he looks for in founders & more!
Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi
Follow Ben: https://twitter.com/bnarasin
1:13 Paul: Has the current crisis changed your investment thesis? If so, how?
2:40 Ash/Christopher: How to overcome the money raised vs revenue generated in enterprise SaaS that requires heavy product work to reach product-market fit?
4:13 Emberlynn/Srinivas: What is the most important content in a pitch deck?
7:26 Guilherme: What will the VC funding landscape look like after the crisis passes?
8:37 Mary: What is the best way to present a newly launched startup that has been severely impacted by COVID-19 to investors?
10:48 Daniel: What advice would you offer college students passionate about venture capital so that they can also become investors?
12:22 Mark: What immediate skepticism do you have when you look at early-stage startups?
15:54 Len: What factor(s) would most set an early-stage (i.e. seed funding, launch-ready, pre-revenue) company apart from others seeking similar funding?
18:15 Aneesh: My startup sells multiple SaaS products for restaurant digitization. We don’t have the bandwidth to handle sales and marketing of all products at once. What should be our strategy to prioritize?
19:49 Linards: At what level of product traction will investors start to be interested? How does it differ across verticals?
22:40 Avidan: What role (if any) will equity crowdfunding play in the venture capital ecosystem at large?
23:43 Adam: What are you seeing related to startup valuations and VC terms post-COVID?
25:18 Emin: What kind of marketplaces would you like to see in the next 5 years?
26:34 Tammy: Do you think people will need a college degree for the jobs of the future?
28:48 Ellie: Post-WeWork, how should a tech startup with profit margins on the smaller side think about building a scalable and ultimately profitable business model?
30:15 Wei: What sectors are you investing in? What are you most excited about nowadays?
31:40 Ope: What skill sets do you need to move into VC from a non-Investment Banking background?
33:09 Suruchi/Mireille: In a medium article you wrote you wrote: "winter is here, severely ....don't obsess about the downside, think about the opportunities.” What opportunities have arisen so far? What changes are permanent and what changes are temporary?
35:20 Nghia: What are some books that you recommend today?
39:30 Ben: Are there areas that are non-investable at the moment whether it be overcrowded, overpriced, or the prospects aren’t great due to COVID?
40:24 Charles: Do you have any instances where a founder's positive or negative traits/signals have influenced a deal decision? On reflection, has instinct proved a better indicator than hard numbers?
43:42 Dave: What was your biggest exit/best investment? How did you source the deal? Alternatively, could you tell your worst anti-portfolio story (most successful company you passed on)?
44:46 Barry: What are some interesting healthcare startups or spaces that you have a favorable outlook for?
45:51 Raman: What’s your take on the future of learning?

1:03 Jason intros Garry Tan and checks in on how his quarantine has been going
4:39 How does Garry look at Initialized's portfolio companies? What are his 3 groups of companies dealing with COVID?
8:04 How will VCs react to the crisis? Why does Initialized specifically focus on Seed-stage companies?
11:13 How does Initialized contact downstream investors about their companies, and how has that changed during COVID?
14:12 Thoughts on Posterous, data-storage singularity & more
18:04 Losing thousands of photos after getting banned from Flickr and how that plays into software as the new government, becoming a super-router
22:32 How Spotify's access to public capital gives them an acquisition advantage, collab concepts
24:51 How does Initialized size their follow-on investments?
29:11 For how long is Initialized planning on operating fully remote? Thoughts on going back to work
35:56 What skills has Garry had to improve during his investing career?
43:33 How downstream investors try and take advantage of early-stage investors
47:51 Thoughts on Clubhouse investment, how/if they can scale their exclusivity
56:27 Thoughts on founders selling secondary shares, and how Chris Sacca helped Garry Tan at Posterous
1:02:09 Structural inequality leading to rich-bashing, how Fiat currency impacts welfare inequality
1:07:09 Thoughts on UBI, Instacart, potential profitability of food-delivery companies
1:11:31 Perception of Tech in the Bay Area, commercial real-estate in SF, Facebook's game-theory remote pay scale
1:18:27 Could today's tech giants (Google, Facebook, Uber) have grown to the heights they did as fully remote companies? Can IPO-level companies be consistently built while remote?
1:24:49 Do the best founders appear ageless? New Twitter features: good or bad?

0:43 Jason intros TechStars CEO David Brown
4:47 TechStars leading the virtual accelerator trend
10:21 Will TechStars go with a hybrid model going forward and what key points should remote accelerators focus on?
15:27 How did TechStars settle on the number of 10 companies per cohort?
17:28 What has TechStars seen across their portfolio since COVID started?
21:21 Sustained changes vs. temporary changes due to COVID, will COVID lead to more entrepreneurs?
31:58 How to explain edge-case funding scenarios to founders who have real businesses that are having troubling raising capital, taking a long-term view on accelerator engagement, why B2B is easier than B2C
36:22 Why angels invest in one company over the other? Do metrics matter as much as personal relationships? What are ideal founder characteristics that David looks for?
40:25 How TechStars selects mentors by surveying their mentees, comparison against Y Combinator
51:45 Opportunity for going global, David's relationship with Co-Founder David Cohen
1:00:30 Would TechStars ever go public?

Slice CEO Ilir Sela answers questions from founders: tips on selling into scattered markets (like Mom & Pop shops), COVID's impact on the restaurant industry, scaling Slice's $43M Series C & more!

Join the TWiST Slack: https://launchevents.typeform.com/to/kLq5Bi

Check out Slice: https://slicelife.com/

Follow Ilir: https://twitter.com/IlirSela

1:05 Knyck: You mentioned Slice being a platform to provide the technology and buying power of scaled companies to small pizza businesses. Do you think that mom and pop stores in other industries like retail or services could use a similar platform, or is this type of structure specifically fitted for the economics of the pizza industry?

3:32 Michael: How do you see the restaurant industry changing in NYC post-COVID, and where do you see the growth opportunities to create a new type of offering?

5:17 Chris: I’m building a loyalty program startup for restaurants. We’re specifically targeting non-chain ethnic restaurants and customers who may have ethnic nostalgia for cultural foods. What do you think the opportunity looks like nationwide for this demographic? Are most restaurants using mainstream food ordering apps already, or is there a large segment of ethnic restaurants who are off-grid?

9:01 Graham: Mom & pops are such a scattered customer base. Can you shed some light on how you started to get momentum in the early days as a small business yourself? Did early customers have any trust issues with something as important as payment?

14:22 Laura: What is the biggest point of friction you have with adding new pizzerias to Slice? Do you experience many/any pizzerias that don't see the benefit of joining the Slice community? If so, how do you handle these?

18:50 Henry: Have you thought of doing the same for other ethnic food restaurants like Chinese, Indian, Thai etc. and what challenges do you foresee? What would be your approach to tackle?

22:04 Matt: With all the vacant retail that's about to become available, have you thought about helping pizza brands expand into ghost kitchens or helping existing pizzerias launch virtual brands (a la Chuck E Cheese)?

24:33 Ian/Andrew (similar questions): What is this funding round helping your business and platform do for the Pizza shops and their customers? How do you plan on scaling your $43M Series C? How have your plans changed since Slice has gone mostly remote?

31:10 Charles: Please expand on the apparent disparity in pricing across platforms/instore. How can food often be cheaper through a middleman? Our family often finds the most frictionless experience for our regular pizza place is to call in as it's often a single dish. How can this be simplified further? One push pizza?

37:58 Matt: Can you speak to "why pizza” and not Chinese food? At the end of the day, are you limiting yourself by picking one category?

40:32 Mahreen: Curious to know more about Slice's marketing. What marketing channels have been most effective for your platform (in acquiring both customers/new businesses)?

42:14 Ian: What response did you get from companies to sign up, was the take up easy? Or did you have to convince them in a specific sales pitch, how did you frame it?

43:51 Presh: You seem to have a curated following list on Twitter, curious to know your favorite accounts to follow that have impacted your business thinking.. top 5 accounts you recommend following?

45:31 Presh: Where does Slice need to be in order to see an IPO?

47:31 Ian: What are your plans to develop your branding and web/mobile app

0:51 Jason intros Zach Coelius & Sam Parr
2:28 Barstool Sports vs. Call Her Daddy
6:49 Penn National Gaming stock soaring, Dave Portnoy winning this controversy
13:17 SoftBank reports $17.7B annual loss, worst figures in 39-year history
17:19 Does SoftBank's involvement typically include a loss of focus for the founder?
21:43 TikTok’s parent co. Bytedance trades at a $140B valuation, poaches Disney’s former Head of Streaming as new CEO of TikTok
25:08 Was Kevin Mayer wrong to take this role? Are TikTok's recommendation algorithms the best in the world?
28:52 How do Chinese companies grow so rapidly?
32:06 Facebook launches Shops, is Zuck trying to kill e-commerce giants? Zach on his experience with Facebook slowly killing his business
40:06 How does Facebook's product organization work?
47:13 Jason on the future of social networks
49:56 Amazon potentially acquiring AMC Theatres, could this be an Amazon Prime upsell?
53:52 Everyone gives their best idea for Amazon's first move after buying AMC
59:59 Zach on his quarantine deal flow

Angel investor Jason Calacanis (Uber, Calm, Robinhood) interviews the world’s greatest founders, operators, investors and innovators. Get an insider’s look into venture capital, learn how to start and scale your own startup, and ride the cutting edge of technology in today's headlines and beyond.