Confronting Imposter Syndrome as a Startup Founder

"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

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.

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.

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.