Office Hours: I'm the CEO and co-founder of Generally Intelligent and Sequoia Scout. I was previously a YC backed founder and Chief of Staff at Dropbox.Featured

ElphaStaff's profile thumbnail
Thanks so much for joining us @kanjun!Elphas – please ask @kanjun your questions before Friday, August 20th. @kanjun may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
madelynmay's profile thumbnail
Hi Kanjun! Thanks for being willing to answer questions on here :)I'm preparing to apply for the Winter 2022 cohort of YC. I've never applied to an accelerator or received any type of funding before - do you have any tips or advice for the YC application process in particular and/or promoting, funding, and building a startup in general? Grateful for any advice you might have as I enter this new territory!
kanjunqiu's profile thumbnail
For the YC app: be as concise and direct as possible! That's basically the number one piece of advice I give founders when I review their applications. Do not use flowery language or marketing-speak - explain your business like you're explaining to a 5th grader (except in rare occasions).Aside from that, there's plenty of general startup advice online - I'd recommend YC's How to Start a Startup series.
iynna's profile thumbnail
It's great to have you here! I'd love to hear about your journey raising your own fund (as much as you can and want to share) how big is the fund? how did you find your first commitment? how long did the process take for you to close the first fund? What has been the strategy to source founders? And totally aside, I love the Sequoia scout program, so I was wondering how did you get involved? :)
kanjunqiu's profile thumbnail
Iynna, thanks so much for the questions!For raising the fund, I mostly went to people I know and have worked with in the past, since they already know me and my work. It's much easier to raise from folks you have a trusted relationship with :). First commit and other commits have mostly come this way so far. It usually takes people a year or so to close a fund, and we are thinking about whether to keep raising or wrap it up.For founders - we have a strong network of friends and former colleagues who are also early-stage founders and who know others who are starting companies, even if they haven’t yet publicly launched. So, our deal flow primarily comes from in-network. We also look at the companies coming out of incubators (e.g. YC).For the Sequoia Scout program, I knew the team from my time at Dropbox. I actually considered becoming a full-time investor after I left Dropbox, but ended up starting my own company instead, so they asked me to come aboard as one of their early scouts. It’s been a great program!
iynna's profile thumbnail
Thank you so much for responding so candidly! I really appreciate it! I'd love to connect and talk more about Outset if you're open to it :-) Regarding your strategy to source founders it makes perfect sense - the network is really where you get started. As for the Sequoia scout program - so glad to hear it worked out well for you :)!
Hi Kanjun, how does your day-to-day life doing research differ from doing execution/building? How did you know that you would enjoy doing research without having done a PhD?
kanjunqiu's profile thumbnail
Hi there! My core drive has always been to try to understand the world and construct explanatory models for why things work the way they do. In another life, I probably would have been a theorist in some field! I'm also surrounded by researchers/scientists (friends, housemates, etc.), so I had a pretty good idea of what that life would be like.That said, my role in running a research company isn't purely just research - it's a lot of leadership, culture-building, hiring, company-building. So in that sense it's not hugely different than doing a startup.
jackieschafer's profile thumbnail
Hi! Would love to know, what was your core skill set that helped you the most in being successful in your chief of staff role? Considering hiring for that role and would love to learn what skills I should be looking for. Thanks!
kanjunqiu's profile thumbnail
Hey Jackie! Chief of Staff is a role that's basically entirely dependent on what the CEO and company need, so I would hesitate to recommend a particular skillset. I think what helped me most was being a very good communicator, and for some reason able to get things done cross-functionally, align people, get them on the same page, etc. - and that's what Dropbox and Drew/Arash (the cofounders) needed at that time. I think I was also probably reasonably strategic, though I was 23 at the time, so now me thinks that then me was embarrassingly unstrategic 🙈.When I hire for a Chief of Staff, I primarily look for someone who has excellent judgment (i.e. would I trust this person to make decisions on my behalf, and properly flag to me when they need my input?), is a great communicator + writer, and thinks like an owner with the company's best interests at heart.My former Chief of Staff, Ali Rohde, actually has some great resources for hiring one:- Her guide to hiring a Chief of Staff: https://docs.google.com/document/d/15alGXNmrzZ9xpYWFEaDLdBLVrf4kTymuhOLXvsXVKHQ/edit- Her jobs newsletter where she can post your job and get you candidates: https://alirohdejobs.substack.com/
tanmayisai's profile thumbnail
Thanks for doing this! Both your startups seem really interesting! The domain for both is pretty different and your experience at Dropbox seems like a different domain as well. How did you decide on these startup ideas? Were you interested in these domains? Found out or experienced these problems ? Or anything else?
kanjunqiu's profile thumbnail
Hi Tanmayi! I think over the years, I've worked on things that are more and more dear to me. When I joined Dropbox, I knew nothing about SaaS businesses or cloud or file syncing - and that was fine! I suppose I was an early adopter of Dropbox and had a good sense of how the product worked, so that helped a bit. When I started Sourceress, I knew a lot about how to do recruiting well from Dropbox - I think that was one of the key things Dropbox got right. I learned a ton at Dropbox about scaling recruiting processes so that you keep the bar high, and about the dynamics of hiring engineers. So I had a pretty good sense of what I was getting into, and I wanted to bring that knowledge to other startup teams (our customers).Generally Intelligent is totally different, in that it's a problem I've been thinking about my whole life. I've been obsessed with understanding how the human mind works, about why humans learn and grow, since as early as I can remember - maybe age 6. And I've been thinking about what it would look like to create truly human-like machine intelligence since maybe high school. The inflection point happened when a few papers came out in late 2019 that made me and my cofounder believe that we now had a viable path, and that's why we ended up founding this.
heidivogel's profile thumbnail
Why is it so important to get a warm introduction to VC’s, and how do you do this now without all the networking opportunities? And what are your favorite discoveries on your journey to success, what would you change today in the process of getting funded? I have a teenager at home saying that capitalism is the cause of all trouble, what would you say to them!
kanjunqiu's profile thumbnail
A lot of good questions, Heidi! I'll answer them in order:1. VCs rely on warm intros as a proxy to separate signal from noise. They get a lot of cold emails from founders who want to raise money, and it's very hard to tell over email if a founder is good or not. A warm intro means someone else they know is vouching for this founder, which is at least some signal that the founder might be reasonable. In a similar vein, VCs tend to take recommendations from their founders (e.g. people they backed and thus believe deeply in) much more seriously than recommendations from a random person in their network - again, for a similar reason: if you back a founder, you trust their judgment on hiring their team, so you should trust their judgment on people they recommend to you.2. The biggest discovery for me has been in learning how to work with my own mind through meditation, therapy/coaching, and a variety of other techniques. I've released a lot of the externally-driven norms that I was brought up with - desire to please other people, keep the peace, do what others want, be successful, be validated, etc. I think I'm a much stronger founder this time around because my convictions are derived internally from first principles, rather than from social norms, and therefore much much deeper.3. I'd ask your teenager to look at what the average person's life was like in 1600, before capitalism, and ask if they would prefer to live in that world or this one. In 1600, farming families in the countryside would hibernate in the winter (literally sleep all day and eat very little) in hopes of surviving with enough food until spring. In cities, people dumped sewage in basements or the river. Capitalism has given a huge percentage of the world's population access to food, sanitation, and resources that the richest kings could not imagine 1000 years ago. If they feel the world is falling apart, I might also send them this article: https://ourworldindata.org/a-history-of-global-living-conditions-in-5-chartsA view I hold dearly is that humanity is very much in progress. We've only had scientific thinking for 400 years, industrial societies for 200 years, instant global communication for 20 years - of course we should expect to have all the problems we have today. As we solve those problems, new problems will come up - problems are inevitable, but they are also soluble. I don't think capitalism in its current form is the economic system we'll have in 1,000 years, as there are clear issues with it and we're likely to have made significant improvements/changes by then. But I'd also be quite hesitant to throw out the baby with the bathwater - capitalism (and common law) has empowered more individuals to pursue their creative potential than ever before, and I hope that we continue to invent new ways to transform humanity and unleash people's creative potential.
heidivogel's profile thumbnail
Thank you for your honest perspective and it totally make sense. Your 2 answer show me how important it is to show our children some of the new norms of today. And showing them that women can be starting up companies , fund raise and accomplish impact is an important. Internal drive for me is everything. However I sometimes try to listen very well to my children and their view of the world. Since they grow up with all these platforms and the 24/7 connectivity to however and whatever they want. Anyway.... time will tell. And I hope I will soon report on these channels some success with my startup GuardianGamer.
janchoy's profile thumbnail
Curious to learn more about being a scout for Sequoia. How did you get into it and what is the arrangement like? TIA!
kanjunqiu's profile thumbnail
Hi Jan! Sequoia was on Dropbox's board when I was Chief of Staff, and after leaving Dropbox we talked about potentially working together while I was exploring what would then become Sourceress. But then, well, it became Sourceress, we started getting traction, and we decided to turn me into a Scout instead, since I of course could not work there full-time :).The arrangement is wonderful - I have a budget and a fair amount of freedom to make decisions on what to invest in, and how much to invest. I get a percentage of the carry. I don't think I can share more exact terms than that, unfortunately!
hi Kanjun you are amazing. I have a question about your investing process, how do you invest in companies, what is the process like, do you find the companies or does a company reach out to you, and in terms of making an investment, what do you look for re: companies you are looking to invest in? And also, what is the difference between the investments you make as an angel, and the ones you make as a scout? I am going to start looking for the 'first money in' and I would love to know what you look for in that case.
kanjunqiu's profile thumbnail
Thank you for the kind words! We’re particularly interested in founders building in enterprise / pro-sumer, fintech, AI, and deep tech. At the early stages, we look primarily at founders and market potential - in particular, does this have potential to be a $1B company, and do we believe this is the founder who will win this market? Feel free to email my partner Ali at ali@outsetcapital.com if you want us to take a look at your company!
xujenna's profile thumbnail
You're so cool, Kanjun! How did you go from math genius at NNHS to Chief of Staff at Dropbox? —a former neighbor ;)
kanjunqiu's profile thumbnail
Omg, hello Jenna!!! Long time no see :) I *love* the projects on your website ❤️❤️❤️
aliciachen's profile thumbnail
Would you recommend building and honing a skillset before starting a company, or just starting now and figuring it out as you go?
kanjunqiu's profile thumbnail
Hey Alicia! My general perspective on life is that if you want to do a thing, the best way to learn how to do it is to do it, or to work very closely with someone who is doing it. Being at Dropbox taught me some things about being a founder, and taught me a lot about how to think about businesses + what to expect when rapidly scaling a startup. But I learned way more about how to start a startup by actually starting one, and this time around I feel significantly more competent! One thing to note, if you're starting a startup for the first time, is that you want to make sure you're doing it in a high-growth way - that is, be embedded in communities (YC, YPO and other CEO groups, etc.) where you can easily learn about what the journey is like. With startups it is easy to spend years flailing on something without much progress/traction but also without much learning, and if that happens then the second time around you might not have much more to show for it.
tracy's profile thumbnail
What happened with Sourceress and how did you decide to move on from that?
kanjunqiu's profile thumbnail
Good to see you, Tracy!! :) With Sourceress, the primary thing that happened is that I eventually realized automated sourcing is a difficult business to be in, and I became unconvinced that we could build a very large venture-backable business in the space. This is because there's high endogenous churn in the recruiting market - people start and stop hiring roles all the time, and the more we succeed (i.e. a hire is made), the more churn there is (i.e. customer doesn't need our service anymore). On top of that, recruiters frequently change jobs. This made for a bad dynamic where we'd lose customers that we worked best for because they'd make hires, and we'd have to do a re-sale into the company when the recruiter churned. It took a while to figure this out because for years we kept blaming the churn on the product - perhaps if we improved the product, it'd go away. But it ended up being a result of the type of product we were (sourcing) in the market. We explored a bunch of potential pivots in recruiting, but ultimately I didn't believe any of them could make very large businesses because of the market dynamics.
tracy's profile thumbnail
Thanks for sharing your (hard-earned) insight!