The Iterative Podcast

"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

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

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.

“I want every little girl who's told she's bossy to be told instead she has leadership skills.” - Sheryl Sandberg

Confidence is something everyone struggles with, but more so if you're the only woman in the room and everyone doesn't look or think like you. In this episode, we invited Yolanda Lee back to the Iterative Podcast to discuss exactly this: how to find confidence as a female leader. From sharing personal stories on losing (and gaining) confidence, to breaking down the way the workforce was designed specifically for men, it's an episode made for women leaders, by woman leaders.

About Yolanda Lee

Yolanda Lee is the founder and CEO of Uncommon, Asia's first private leadership network for the next generation of female leaders. Prior to this, she led the international consumer partnerships team across Asia Pacific and the Middle East at Deliveroo, building its corporate solutions offering as the Head for Business. She also worked in Africa as the Regional Partnerships Manager for Uber, as well as the Regional Managing Director at HelloFood under Rocket Internet.

About Uncommon

Uncommon is a community learning and development platform for female leaders. Uncommon uses behavioural science, coaching and a supportive community to bridge the gap between knowledge and action and ensure lasting, effective change where it matters most.

For show notes, visit the website here. 

In this episode, we've got Hsu Ken back in the roster - and we've also invited Kuo Yi from Monk's Hill Ventures to talk about the top mistakes founders often make when fundraising.

But instead of the usual Q&A format, we're shaking things up a bit. I got both Hsu Ken and Kuo Yi to stack rank the top three mistakes they often see founders make, so you'll get to hear what are the different priorities that are important for an investor. They also talk about how founders can fix those mistakes - and how the current economic downturn will impact fundraising.

For show notes, go here.

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…

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.

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

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.

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.

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.

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:

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.