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The Iterative Podcast

The Iterative Podcast

By Iterative

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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Sustainable Fashion, By Businesses For Businesses

The Iterative PodcastAug 03, 2021

00:00
52:59
Should You Continue Working On Your Startup? - Episode 01 of The Brian and Hsu Ken Show

Should You Continue Working On Your Startup? - Episode 01 of The Brian and Hsu Ken Show

"Should I continue working on my startup?" It's a persistent question founders ask themselves - and the most difficult to answer. In the first episode of the Brian and Hsu Ken show, the Managing Partners of Iterative break down how founders can tackle this question.


Chapters 0.00 - Introduction 0.27 - Why Is This A Hard Question? 3:57 - Should More Companies Be Sticking It Out? 6:38 - Design Experiments Around Your Runway 9:15 - It Takes A Longer Time to Figure Out Economics 10:00 - Are You Solving the Most Important Problem? 10:50 - Hsu Ken's Thread 11:12 - Are You Growing? 14:08 - You're Growing Fast When You Think Your Metrics Are Wrong 15:29 - Retention is Important 16:12 - Are You Learning? 16:28 - Founders Need Insights Per Minute 18:15 - Best Startups Tend to Be Built Around Secrets 19:00 - Do You Have Ideas for What to Do Next? 21:28 - Startups Need to Engineer Growth 23:04 - Are You Having Fun? 25:00 - Signs You Should Quit Your Startup 28:29 - Learnings → Bets → Growth 28:57 - Swipe to the table in the LinkedIn post 31:15 - How Much Time Founders Should Spend on Learnings, Bets and Growth 36:00 - Wrapping Up

Apr 11, 202336:44
Rejection Fatigue: Handling Rejections from Investors (With Le Yi Khor from Ottodot and Nirali Zaveri from Friz)

Rejection Fatigue: Handling Rejections from Investors (With Le Yi Khor from Ottodot and Nirali Zaveri from Friz)

This time around, we’re talking to Le Yi from Ottodot, and Nirali from Friz on rejection fatigue when fundraising. Ottodot is an educational games startup for children between 7 to 12, and Friz is building tools for freelancers and independents to get hired and paid - both are part of Iterative’s portfolio companies, and of course, part of our community. I invited them both to talk about the often unspoken emotional journey that comes with fundraising: rejections, and what their fundraising processes were like and how they handled rejections.  


Nirali Zaveri

Nirali is the cofounder and CEO of Friz where the team is building tools for freelancers and independents to get hired and paid. Her experiences at Mastercard in Commercial and Small Business Payments helped her realise the struggles freelancers face with their businesses.

Le Yi Khor

Le Yi is the CEO and co-founder of Ottodot, an educational games startup that aims to make learning fun for kids 7-12 years old. Ottodot builds games on Roblox and the games have reached thousands of players in less than 6 months. Her personal mission is empowering youths to realise their fullest potential through good design and technology.


Show Notes 

3:25 - How Nirali got into both YC and Iterative's cohort  

5:46 - “The most important thing is getting your metrics right” - Why Nirali believes it's important for founders to first be customer obsessed. “Fundraising is just a means to an end, and at the end of the day, you're serving your customers and the people you created the business for”  

9:08 - How Le Yi and her co-founder had to learn how to fundraise as first-time founders. “Fundraising is one of the toughest things to learn because it's a private conversation, and the feedback loop is much harder and makes it difficult to learn”  

12:08 - Ottodot's journey in fundraising in a ‘fundraising winter’  

15:25 - “Fundraising strategy is something I completely underestimated” - Why fundraising is a skill and how it can be learned by founders  

18:10 - Le Yi's experience with an investor that told her “this is not how you fundraise”  

19:21 - The most surprising thing about fundraising - it's not the silver bullet that fixes everything  

22:24 - The shift from having someone tell you what to do to figuring something out on your own - why fundraising is also highly subjective  

25:51 - How to discern the fine line between noise and good feedback. “Ÿou need to first emotionally let go” and focus on what your customers are telling you  28:05 - Nirali shares the multiple ways to test out feedback from investors  

33:43 - What rejections mean to both Nirali and Le Yi before, and what it means now  

39:24 - Fundraising isn't something you can switch on and off  

42:06 - Nirali's takeaway - having clarity is important   

43:13 - Le Yi's takeaway - the importance of selling cannot be underestimated

Dec 02, 202245:36
Recording of Livestream Event: "Tell Me Your Startup Idea, I'll Tell You How to Validate It" (With Hsu Ken Ooi)

Recording of Livestream Event: "Tell Me Your Startup Idea, I'll Tell You How to Validate It" (With Hsu Ken Ooi)

We hosted a livestream event where founders (and future founders!) told Hsu Ken their startup ideas, and he told them how to validate it. 

To everyone that participated, thank you! We'll be running more events (physical or virtual) in the future, follow us at iterative.substack.com to make sure you don't miss out.

Nov 17, 202201:02:08
#FutureisFemale: Yolanda Lee on Finding Confidence When You're The Only Woman in the Room
Nov 04, 202234:47
Top Fundraising Mistakes Founders Often Make (With Kuo-Yi Lim from Monk's Hill Ventures and Hsu Ken Ooi from Iterative)
Oct 14, 202242:58
Things to Look Out For When Fundraising (With Nikhil Kapur from STRIVE and Brian Ma from Iterative)

Things to Look Out For When Fundraising (With Nikhil Kapur from STRIVE and Brian Ma from Iterative)

What should founders look out for when they're fundraising? If you do a quick google, you can find loads of things investors should think about before investing in a founder… but not so much for the other side of the table. Founders who are new to fundraising don't have a playbook on fundraising - like what term sheet is right for them, how to carry out DD, what good value add looks like - and because they're new to all of this, some of them don't even realise they signed the short end of the stick.

To change this, we invited Nikhil Kapur from STRIVE and Brian Ma from Iterative, investors who were founders prior, to share more about the common things founders need to look out for when fundraising. In this episode, they talk about…

  • What founders should be asking investors
  • Horror stories on investors from Nikhil and Brian
  • When should convertible notes come in?
  • How founders can navigate through the current funding cycle
  • The green flags from investors - what good investors look like

Nikhil Kapur, Partner at STRIVE

After a decade spent in development and product at Microsoft Office (10M+ SaaS deployments), TommyJams (founder), Pie (SMB SaaS acquired by Google), Nikhil knows how to build scalable SaaS businesses. He's now currently applying these as a VC at STRIVE ($200M+ AUM) as he invests in SaaS and DevInfra being built out of Asia by exceptional founders with a product-led mindset.

Brian Ma, 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.

Show Notes

5:47 - How have the conversations between founders and fund managers shifted

10:42 - What are some of the interesting questions investors get (11:21: Founders aren't asking the right questions - what founders should be asking)

15:31 - Brian's personal story on how he was shortchanged by investors

18:04 - Term sheets signed, and not honoured, is extremely common

18:26 - Nikhil's personal horror story with another investor that "caused a ruckus” - how Nikhil had to personally jump on calls to convince investors to go ahead at 20:44

22:33 - At what stage should startups start considering notes being included into the term sheet

22:57 - Nikhil's blog post 'How convertible notes are killing you’ that went viral four years ago

29:02 - How should founders navigate through the current funding cycle

30:45 - Why Nikhil advises founders to take more active investors in the early stages

34:31 - Why Brian suggest for founders to figure out what your investors are really good at

36:07 - Investors' green flags - what good investors look like

37:41 - Brian's personal story of how his investor value-added for his company in the early days

39:51 - A VC's job is to predict problems that will crop up

41:14 - Nikhil's rule: Try to contribute to every one of his portfolio/founders and be there for them in the tough times and have no judgement policy

43:38 - Should founders spray and pray, or pitch only to specific investors?

46:41 - LP fundraising is very different - Brian spoke to 600 people for Iterative's first fund

47:59 - How to tap into an angel investors' or an accelerator's resources

Sep 16, 202254:40
"Survival is a Prerequisite for Success" - How to Fundraise in an Economic Downturn (With Shiyan Koh from The Hustle Fund and Hsu Ken Ooi from Iterative)

"Survival is a Prerequisite for Success" - How to Fundraise in an Economic Downturn (With Shiyan Koh from The Hustle Fund and Hsu Ken Ooi from Iterative)

This episode is about 'How to Fundraise in an Economic Downturn' - a topic that everybody is talking about. But most of what's happening is heavily centred on the States, and we wanted to provide more nuance for what it means for founders specifically in Southeast Asia. In this podcast, we got Shiyan Koh from the Hustle Fund, and Hsu Ken from Iterative, to shed light on the investors' POV on two things (1) what's happening in the economic landscape (2) how should founders approach fundraising.


3:22 - Shiyan's fundraising experience at Nerdwallet, which was bootstrapped to $50m

8:00- Hsu Ken's fundraising experience for Decide.com - how they didn't need to think about macroeconomics

9:51 - Current perspective on what's happening in the fundraising market - and why it's important to talk about the stages because different stages are impacted differently

10:54 - There's a slow down in the early stages - fewer preemptive deals

12:44 - Why flight to quality matters now

13:57 - Why the Hustle Fund has not changed their approach to investing (despite the current downturn) - and why they're not slowing down at 16:45

16:22 - Why Iterative isn't slowing down either (FOMO in reverse)

17:52 - The name of the game is 'don't die' - if you have to take a flat round, that's better than dying six months from now. Don't tie valuations to your ego

19:08 - Getting first term sheet is significantly harder now - fundraising process will take longer (at least six months)

19:51 - "Survival is the prerequisite to success" - Shiyan Keep things moving, sign a wire, send the docs.

21:20 - The key to being successful in fundraising is to be organised

23:03 - Pitches have to be different now - show clear signs of revenue. Protect your runway because even investors don't know what's going to happen in the future

24:56 - How The Hustle Fund is helping their portfolio companies navigating fundraising

26:03 - There's only two ways to survive longer: get more money or spend less money

27:14 - Why Shiyan believes (philosophically) that companies should be run 10% away from full capacity

28:05 - What founders can learn from Shopify when they made an expensive bet on hiring more to capitalise on growing (Covid-19) demand

29:10 - What can founders do if they, for some reason, just can't fundraise?

29:32 - Why the founder mentality makes or breaks a company

31:15 - How to go cockroach mode to survive long enough

33:07 - Unhelpful conventions that Shiyan thinks Southeast Asian founders should take note of

34:15 - We're seeing more predatory deal terms

35:06 - Why overly structured deals at early stages are a no go for Shiyan

36:52 - Should founders take lower deals?

38:36 - How should founders keep their mentality and health in check?

39:45 - Reality: You're more than your startup

41.20 - “We've been through this before - and we're all still here”


Shiyan Koh, The Hustle Fund

Shiyan Koh is the Managing Partner of The Hustle Fund, a venture capital fund that invests in pre-seed startups in the US, Canada and Southeast Asia. She joined Nerdwallet as employee #10, and ran business operations and corporate development, helping the company grow from US$1M to US$150M in revenue.


Hsu Ken Ooi, Iterative

Hsu Ken is the Managing Partner at Iterative. He 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.

Sep 07, 202243:42
Startup 101: Finding the Right Co-Founder

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.

Sep 13, 202149:57
Startup Ideas We Want to Fund

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.

Aug 30, 202142:54
Confronting Imposter Syndrome as a Startup Founder

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.

Aug 25, 202158:40
Startup 101: How to Master Fundraising

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

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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: PodcastNewsletterBlogWebsiteTwitter

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)."

Aug 18, 202136:05
Startup 101: How to Get Into an Accelerator

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.

Aug 04, 202147:39
Sustainable Fashion, By Businesses For Businesses

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

Aug 03, 202152:59
Startup 101: How to Deal with Burnout

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.

Jul 06, 202138:17
Startup 101: How to Build a Recruiting Machine, Part 1

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

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.

Mar 31, 202136:47
Founder Stories: Yolanda Lee on Finding Her Own Path and Building a Professional Community for Women

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).

Mar 17, 202101:15:18
Founder Stories: Tim Grassin, Co-Founder of TendoPay

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.

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
Feb 24, 202101:09:42
Founder Stories: Vibhas Jain on Growing Up in India, Not Going to Stanford and Starting Outside Voice

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
Feb 03, 202155:25
Founder Stories: Jeff Liu and Justin Louie from Jenfi on How They Got Started and Being 2nd Time Founders

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.

Nov 26, 202054:22
Startup 101: How to Find a Good Problem For Your Startup to Work On

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.

  1. Why is it important to focus on problems, not solutions?
  2. Why it's important to work on a good problem?
  3. How to tell if a problem is a good problem?
  4. Do you need to have the problem to solve it?
  5. How do you look for good problems?

If you're thinking about starting a startup, this is where you should start.

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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.

Oct 25, 202046:40