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The Iterative Podcast

The Iterative Podcast

By Hsu Ken Ooi
The Iterative podcast talks to founders, investors and operators from the startup community in Southeast Asia and occasionally Silicon Valley.

Iterative is a YC style accelerator focused exclusively on Southeast Asia. Iterative invests US$150K into startups, twice a year. After investing they work intensely with the founders to help their startups grow before culminating in a Demo Day.
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Startup 101: How to Deal with Burnout

The Iterative Podcast

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Startup 101: Finding the Right Co-Founder
The right co-founder can help your startup thrive, but it can be a complicated process. Hsu Ken Ooi and Brian Ma come together to simplify this process in today's podcast episode 'Startup 101: Finding the Right Co-Founder'. The following topics are discussed: 00:00 Introductions 00:24 Is a co-founder necessary? 07:46 Considerations when choosing a co-founder 16:22 How Brian and Hsu Ken met 19:10 Avenues to find co-founders 29:13 Maintaining co-founder relations 39:00 Dealing with co-founders not "pulling their weight" 44:45 Long-distance relationships 47:44 Concluding thoughts Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc About the Speakers Brian Ma | Founder and General Partner at Iterative | https://www.linkedin.com/in/zealoustiger Brian is a partner at Iterative Capital and three time founder turned investor. Brian was previously founder and CEO of Divvy Homes ($150M+ raised, backed by a16z, GIC, Tiger), Weave (YC S14, acquired), and Decide (Series C company, acquired by Ebay). Hsu Ken Ooi | Founder and General Partner at Iterative | https://www.linkedin.com/in/hsukenooi Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide, an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
49:57
September 13, 2021
Startup Ideas We Want to Fund
In 'Startup Ideas We Want to Fund', Hsu Ken talks about startup ideas and trends worth exploring in 2021. Hopefully, this will (1) encourage founders working on these ideas to apply to Iterative and (2) help people get started on ideas we think are interesting. Topics discussed in this episode: 00:00 Introductions 00:50 Inspiration behind Hsu Ken's "Request for Startups" 01:55 Anti-status quo as inspiration 02:55 1) Allow Anyone to Sell Anything 06:40 a) Easy logistics 10:09 b) AirBnB for food 15:08 2) The Financial System is Painfully Outdated 20:08 a) Crypto finance 28:35 3) Digitise Everything 30:10 a) Online pharmacies 34:24 4) Celebrity culture 41:23 Covid-19 as an accelerator 42:52 Covid-19 as a decelerator? 44:05 Irrelevant food section Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc About the Speaker Hsu Ken Ooi | Founder and General Partner at Iterative | https://www.linkedin.com/in/hsukenooi Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide, an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
42:54
August 30, 2021
Confronting Imposter Syndrome as a Startup Founder
Dear founders, have you ever felt like a fraud? You may be experiencing imposter syndrome. But you're not alone. Research suggests that an astounding 70 percent of people will experience this at some point in their lives. In this week's Iterative Podcast episode, Charles and Hsu Ken open up about their own experiences with imposter syndrome and offer advice on dealing with it. Topics discussed in this episode: 00:00 Introductions 00:48 Hsu Ken's experience with imposter syndrome 004:50 Charles' experience with imposter syndrome 08:31 Different types of imposter syndrome 10:35 Cases of disillusionment 13:55 The impact of (not) having a co-founder 15:00 Who doesn't have imposter syndrome? (entering the fictional realm) 19:20 Dealing with imposter syndrome: Goal-setting 20:30 How your objectives affect imposter syndrome 22:35 Dealing with imposter syndrome: acknowledging and identifying the root cause(s) 24:00 Having agency 25:50 Labels 29:40 Dealing with imposter syndrome: collective solidarity and feelings 38:20 Just doing it 39:42 Should anyone feel more imposter syndrome than they do? 40:50 Is imposter syndrome inevitable without experience? 42:40 Reacting to imposter syndrome 45:15 Reframing emotions and feelings 49:18 Dealing with imposter syndrome: gain a broader perspective, get more data points 52:42 Identifying over-confidence and under-selling 56:24 Dealing with imposter syndrome: ground it in reality 57:30 Dealing with imposter syndrome: make a plan Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc About the Speakers Charles Lee | Co-Founder and CEO at CoderSchool | https://www.linkedin.com/in/charleslee5/ Charles is the co-founder and CEO of CoderSchool. Charles started CoderSchool in 2015 to bring opportunity to everyone, everywhere, by developing the highest quality technical training programs in the world. Prior to Vietnam, Charles had 10+ years of industry experience working as a software engineer in Silicon Valley. His experience spanned across various industries, including gaming, e-commerce, and digital health. He was an early engineer at Luvocracy, acquired by Walmart; A Bit Lucky, acquired by Zynga; and GemShare, acquired by NextDoor. Charles holds a B.A. in Computer Science from the University of California, Berkeley. In his free time, he raises a poodle named Chuon Chuon, trains for Ironman Triathalons, and repairs antique typewriters. Hsu Ken Ooi | Founder and General Partner at Iterative | https://www.linkedin.com/in/hsukenooi Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide, an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
58:40
August 25, 2021
Startup 101: How to Master Fundraising
In 'Startup 101: How to Master Fundraising', Brian Ma presents us with a Fundraising Bootcamp. As the founder of various successful startups, Brian is no stranger to the process of fundraising. In this session, he will cover the fundamentals of fundraising and common mistakes founders are making. Topics discussed in this episode: 00:35 The importance of funding 01:05 Different funding paths 02:45 What matters when it comes towards funding: external factors, internal factors, and creating FOMO. 09:15 The breakdown of fundraising 09:49 Preparation: how much to raise, what investors to target, how to create a compelling pitch deck, and generating leads. 14:55 Process: how to manage investor interest, run a good process and get the first term sheet. 27:38 Closing: How to leverage the first term sheet to get other term sheets, negotiating and closing your round. 31:52 Common mistakes Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD Subscribe to The Iterative Podcast on Apple Podcast • RSS • Google • Overcast • Spotify • YouTube About IterativeIterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: Podcast • Newsletter • Blog • Website • Twitter About the Speaker Brian Ma | Founder and General Partner at Iterative | https://www.linkedin.com/in/zealoustiger/ Brian is a partner at Iterative Capital and three time founder turned investor. Brian was previously founder and CEO of Divvy Homes ($150M+ raised, backed by a16z, GIC, Tiger), Weave (YC S14, acquired), and Decide (Series C company, acquired by Ebay)."
36:05
August 18, 2021
Startup 101: How to Get Into an Accelerator
In 'Startup 101: How to Get Into an Accelerator'', Hsu Ken demystifies accelerators. Tune in to find out make makes accelerators unique, how they can help your startup grow, how to choose the "right" accelerator, what accelerators are looking for, and much more. Topics discussed in this episode:  0:00 Introductions 0:29 Overview of the startup ecosystem 3:38 What makes accelerators unique 6:46 Impact of Covid-19 9:51 How accelerators approach (a lack of) contextual-specificity 12:50 Finding the "right" accelerator and defining a "good" accelerator 22:05 Application approaches: Intentional vs Spray and Pray 23:13 When to apply 25:33 The application process and what accelerators look for 29:55 How startups can prepare 34:04 What happens in an accelerator and how to maximise the experience in one 40:40 Post-programme 43:20 Gaps in the accelerator ecosystem 46:21 Final thoughts Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc About the Speaker Hsu Ken Ooi | Founder and General Partner at Iterative | https://www.linkedin.com/in/hsukenooi Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide, an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
47:39
August 04, 2021
Sustainable Fashion, By Businesses For Businesses
Sustainable fashion matters. But instead of the everyday consumer, have you considered sustainable fashion for corporate clients? This episode features Keith, a rising senior at Yale-NUS College and the Chief Sustainability and Design Officer of Man's Best Friend (MBF), a Singapore-based startup producing sustainable and high-tech apparel for corporate clients by blending cutting edge nanotechnology with quality fabrics. We discuss sustainability in fashion, its shortcomings, what gap MBF is trying to fill, and more. Topics discussed in this episode: 00:00 Introduction 1:25 What is "sustainability" in fashion? 5:35 The Ecosystem of Sustainable/Fast Fashion 9:06 Problems afflicting sustainability in fashion 12:56 Man's Best Friend (MBF) and Sustainable fashion for businesses 13:36 Sustainable fashion for MBF and their three pillars 15:39 (1) Corporate sustainability 17:25 (2) Functional sustainability 21:35 (3) Progressive sustainability 23:04 Engaging with corporations and juggling a start-up with college 27:30 Demystifying the fashion industry's complex supply-chain 31:00 Impact calculations: How good is good enough? 34:30 Way of assessing sustainability: certifications and standards 37:17 Difficulties procuring certifications 39:28 Customisation and sustainability 44:12 Barriers to entry in being sustainable 47:52 MBF's goals 49:50 Future of sustainability in fashion Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About the Speaker Keith Wo | Chief Sustainability and Design Officer of Man's Best Friend (MBF) | https://www.linkedin.com/in/keith-wo/ Keith is the Chief Sustainability and Design Officer at MBF and is a rising senior at Yale-NUS College. His passion for marrying aesthetics into functional and practical forms has allowed him to open up the conversation on sustainable apparels About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc
52:59
August 03, 2021
Startup 101: How to Deal with Burnout
In 'Startup 101: How to Deal with Burnout', Hsu Ken Ooi and Brian Ma discuss an often untold story about running a startup: burnout. Topics discussed in this episode: 0:20 Brian and Hsu Ken introducing themselves 1:20 What is burnout? Brian and Hsu Ken share their own experiences with burnout. 6:25 How burning out affected Brian and Hsu Ken's wider network, including their startups. 9:50 The glamorisation of work and productivity. 13:16 Solutions to prevent and tackle burnout (e.g. hiring, creating a feedback loop, check-ins, setting boundaries, etc.). 31:20 What Brian and Hsu Ken would have done differently as first-time founders. 35:08 Final thoughts. Let us know what you think! We would really appreciate your feedback. https://airtable.com/shrO0s884vjdI1emD About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Find out more about Iterative: https://iterative.vc About the Speakers Brian Ma | Founder and General Partner at Iterative | https://www.linkedin.com/in/zealoustiger Brian is a partner at Iterative Capital and three time founder turned investor. Brian was previously founder and ceo of Divvy Homes ($150M+ raised, backed by a16z, GIC, Tiger), Weave (YC S14, acquired), and Decide (Series C company, acquired by Ebay). Hsu Ken Ooi | Founder and General Partner at Iterative | https://www.linkedin.com/in/hsukenooi Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide.com an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
38:17
July 06, 2021
Startup 101: How to Build a Recruiting Machine, Part 1
In Part 1 of How to Build a Recruiting Machine, Hsu Ken Ooi is joined by his Iterative Co-Founder, Brian Ma to talk about the following: 0:56 Why hiring is important 2:00 Why most founders underestimate the importance of hiring 5:07 How hiring changes as your startup grows 13:54 Accepting that you're going to hire for roles you're not familiar with 16:52 The types of qualities you want to look for in early hires 24:14 The types of roles you want to hire in early stage startups 29:24 Tips for writing effective job descriptions Let us know what you think! hsuken@iterative.vc Subscribe to The Iterative Podcast and find out more about Iterative Podcast Newsletter Blog Website Twitter Speakers Brian Ma, Founder and General Partner at Iterative Brian was previously the Co-Founder and CEO of Divvy Homes (a16z, GIC). In 2014, he and Elpizo Choi started Weave (YCS14). In 2009, he started Decide.com an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. In 2005, he was one of the first PMs at Zillow before they launched. Brian has a BS in Computer Science and Electrical Engineering from the University of Washington. Hsu Ken Ooi, Founder and General Partner at Iterative Hsu Ken was previously the Chief Product Officer of Workmate, an on-demand blue collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide.com an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington.
36:47
March 31, 2021
Founder Stories: Yolanda Lee on Finding Her Own Path and Building a Professional Community for Women
In this episode, we have Yolanda Lee, co-founder of Uncommon. Uncommon is a private leadership network for the next generation of female leaders in Southeast Asia. Uncommon provides a strong and uplifting network, a personalized development roadmap, tailored courses and workshops, and in reaching speaker series, all-in-one membership.  We talk about her early life in Canada (1:23). At 20, Yolanda rented an abandoned industrial warehouse in her home tenants, funk, and major Lazer to play there by messaging them on MySpace (24:15). She went on to intern at the European court for human rights, graduated top of her class at Oxford, and worked for Uber and Rocket Internet in Africa (32:53). We talk about what drove her to these different paths and how those experiences shape her. She opens up about her motivation for starting Uncommon, what her personal experience has been being in male-dominated industries, why Uncommon is so important, and what men can do to help (49:36).
01:15:18
March 17, 2021
Founder Stories: Tim Grassin, Co-Founder of TendoPay
Tim Grassin is a Co-Founder of TendoPay (Iterative S20), the largest online installment provider in the Philippine. On this episode, I talk to Tim about his earlier influences, switching from finance to entrepreneurship, how he built a multi-million dollar design agency, why he gave that up to start a startup in the Philippines and how they tested their initial idea by building a fake website that sold fake products to see if people would try their fake financing product. Watch it on YouTube Listen to the podcast Topics 1:37 – How our childhood may or may not have shaped our future as entrepreneurs 9:37 – Early professional influences and business school 14:37 – Getting into startups after the financial crisis 22:50 – Quitting his job to start a presentation design company 24:57 – Getting the first few customers 29:48 – Scaling up customer growth 33:37 – The importance of learning how to learn 38:16 – Going from a multi-million dollar agency to building a tech product 43:55 – Coming to Southeast Asia and starting TendoPay 53:26 – TendoPay’s first MVP 1:01:18 – We reminiscence about growing up playing video games About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Connect with Iterative Sign up for the Iterative NEWSLETTER: https://iterative.substack.com Visit the Iterative PODCAST: https://anchor.fm/iterativevc Visit the Iterative BLOG: https://iterative.vc/blog Visit the Iterative WEBSITE: https://iterative.vc Follow Iterative on TWITTER: https://twitter.com/iterativevc
01:09:42
February 24, 2021
Founder Stories: Vibhas Jain on Growing Up in India, Not Going to Stanford and Starting Outside Voice
Vibhas Jain is the co-founder and CEO of Outside Voice (Iterative S20), a no-code app builder for WhatsApp. On this episode, we talk about Vibhas (Vibes) childhood growing up in India, getting into and moving to Stanford but never actually attending Stanford, how he met his co-founder and came up with the idea of Outside Voice. Discussion (1:00) – Vibe's childhood growing up in India (6:30) – Vibe's first product idea and trying to convince people to build it (12:40) – What the feeling of being in SF was like (19:15) – Where did Vibe's entrepreneurship DNA come from? (22:00) – Vibe's tries to build the same music app again, years later (29:37) – Vibes's music app gets on Techcrunch and they meet Sequoia (38:34) – How Vibes met his co-founder and how Outside Voice was started (48:35) – When and why should you join an accelerator? (51:00) – Vibes favorite place to get Indian food in Singapore (54:00) – Vibes talked himself into a DJing gig by telling them he was a big DJ in India About Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day. Connect with Iterative Sign up for the Iterative NEWSLETTER: https://iterative.substack.com Visit the Iterative PODCAST: https://anchor.fm/iterativevc Visit the Iterative BLOG: https://iterative.vc/blog Visit the Iterative WEBSITE: https://iterative.vc Follow Iterative on TWITTER: https://twitter.com/iterativevc
55:25
February 03, 2021
Founder Stories: Jeff Liu and Justin Louie from Jenfi on How They Got Started and Being 2nd Time Founders
Jeff Liu and Justin Louie are the co-founders of Jenfi (YC W20). Jenfi lends to small businesses in Southeast Asia based on revenue. Jenfi has raised US$2.1M in funding. Before Jenfi, Jeff was the co-founder and CEO of GuavaPass, and Justin was the CTO of Guavapass. GuavaPass raised US$5M before being acquired by ClassPass in 2019. In this episode, we talk about where they are from, how they got into startups, how they met, where their ideas come from, what it's like to be a 2nd-time founder and advice for 1st-time founders, and much more.
54:22
November 26, 2020
Startup 101: How to Find a Good Problem For Your Startup to Work On
In our first episode, Brian and Hsu Ken answering the following questions. Why is it important to focus on problems, not solutions? Why it's important to work on a good problem? How to tell if a problem is a good problem? Do you need to have the problem to solve it? How do you look for good problems? If you're thinking about starting a startup, this is where you should start. --- Brian Ma Brian is a General Partner at Iterative. Prior to Iterative, he was the Co-Founder and CEO of Divvy Homes (a16z, GIC). In 2014, he and Elpizo Choi started Weave (YCS14). In 2009, he started Decide.com an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. In 2005, he was one of the first PMs at Zillow before they launched. Brian has a BS in Computer Science and Electrical Engineering from the University of Washington. Hsu Ken Ooi Hsu Ken is a General Partner at Iterative. Prior to Iterative, he was the Chief Product Officer of Workmate, an on-demand blue-collar staffing platform in Southeast Asia. In 2014, he was VP of Product at Weave (YCS14). In 2009, he started Decide.com was an early machine learning company that predicted the future price of consumer goods. It was acquired by eBay in 2013. Hsu Ken has a BS in Mathematics and Statistics from the University of Washington. Iterative Iterative is a YC style accelerator focused exclusively on Southeast Asia by the founders of Divvy (a16z, GIC), Weave (YCS14), Decide (acquired by eBay) who have collectively raised $100M+ in VC. Iterative invests US $150K into early-stage startups twice a year then works with them intensely for 3 months culminating in a Demo Day.
46:40
October 25, 2020