The Iterative Podcast Iterative

"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

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…


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