The Exchanges

Q So what book would you most recommend for me? Tell me.

A I love The Wright Brothers, which was written by David McCullough a couple years ago. Just this past week was the anniversary of that first controlled flight that the Wright Brothers did back in 19 oh three. And I think what's so fascinating about them is In just over four years from the time they first started researching how to create an airplane, they had an airplane up in the air having worked through multiple groundbreaking inventions in order to accomplish that. It's just a really remarkable story, even in this age where we have what seemed like overnight success technology companies. For them to have accomplished what they did in just over four years, I think, is such an inspiring story, and David McCullough is a fascinating writer, so it's a really great read.

AI assessment note: “I love The Wright Brothers, which was written by David McCullough”

Q know you're a runner. I do want to touch on the element, though, that you suggested there being kind of the distributed workforce and almost kind of the future of work. You've been in the industry now for a couple of decades, so I'd love to ask, in terms of kind of the operational elements, how is managing a startup today easier than maybe 10 years ago, do you think?

A Well, one thing I would say is there's just so much more information available even than there were 10 years ago. You can Read online about nearly every problem or issue or facet of your business that you need to tackle, and sometimes that's through discussion boards, and sometimes that's through private groups you can join, and sometimes that's through blogs from operators and from venture capitalists, so there's so many great resources, and then there are so many systems in place to help you launch and run a startup with, frankly, less dependency than before on hiring specialists or team members or consultants who are just dedicated to some admin or operational tasks. The biggest, I'd say, element of that is, of course, AWS, or the similar services from Google and Microsoft, cloud services, but also the rise of more online services for managing a company. We probably use, I'd say, 20 online or SaaS services to run our company, and I'm not even talking about other online services related to building our product like Jira and GitHub, but these are services for operating our company like managing our company benefits, or easier ways to manage our company's finances, or online services like eShares, For managing our company's cap table and hiring services like hired.com and handshake. Our last two hires each came from those two services that previously we would have had to work t…

AI assessment note: “there's just so much more information available even than there were 10 years ago.”

Q beginning, and I hope my interview style has changed significantly because Guy was fantastic, but I was less than brilliant. I would love to start today on a little bit about you. You have one of the most interesting careers in the business from startups to wineries in Chile to large incumbents. So how did you make your way into tech and startups and then really come to found Astro?

A Well, after university, I spent a few years in the 19 nineties working for a nonprofit organization that was helping support the process of democratization that many countries in Southern Africa were taking at that time. So as part of that, I lived and worked about two years in Cape Town, South Africa, which was in the period shortly after the end of apartheid and when Nelson Mandela had been elected president in South Africa. But what I learned very quickly is that in a country where 80% of the population, primarily the black South Africans, were suddenly now free to vote and in theory to participate in all aspects of the country's development, the economy, politics, education system, in reality there were still huge barriers for most of the people to participate in a meaningful way. And at the time I didn't know anything about how economies or businesses worked, so I came back to the U.S. to go to grad school at Stanford. And after that, I joined a startup here in the Valley called OneBox as the first business person on the team. And the first person I met when I was interviewing was the engineering lead, Satish Darmaraj. Today is now our, our investor in my current company, Astro.

AI assessment note: “joined a startup here in the Valley called OneBox as the first business person”

Q know you're a runner. I do want to touch on the element, though, that you suggested there being kind of the distributed workforce and almost kind of the future of work. You've been in the industry now for a couple of decades, so I'd love to ask, in terms of kind of the operational elements, how is managing a startup today easier than maybe 10 years ago, do you think?

A Well, one thing I would say is there's just so much more information available even than there were 10 years ago. You can Read online about nearly every problem or issue or facet of your business that you need to tackle, and sometimes that's through discussion boards, and sometimes that's through private groups you can join, and sometimes that's through blogs from operators and from venture capitalists, so there's so many great resources, and then there are so many systems in place to help you launch and run a startup with, frankly, less dependency than before on hiring specialists or team members or consultants who are just dedicated to some admin or operational tasks. The biggest, I'd say, element of that is, of course, AWS, or the similar services from Google and Microsoft, cloud services, but also the rise of more online services for managing a company. We probably use, I'd say, 20 online or SaaS services to run our company, and I'm not even talking about other online services related to building our product like Jira and GitHub, but these are services for operating our company like managing our company benefits, or easier ways to manage our company's finances, or online services like eShares, For managing our company's cap table and hiring services like hired.com and handshake. Our last two hires each came from those two services that previously we would have had to work t…

AI assessment note: “It doesn't take us the same number of people or the same amount of spend”

Q So what book would you most recommend for me? Tell me.

A I love The Wright Brothers, which was written by David McCullough a couple years ago. Just this past week was the anniversary of that first controlled flight that the Wright Brothers did back in 19 oh three. And I think what's so fascinating about them is In just over four years from the time they first started researching how to create an airplane, they had an airplane up in the air having worked through multiple groundbreaking inventions in order to accomplish that. It's just a really remarkable story, even in this age where we have what seemed like overnight success technology companies. For them to have accomplished what they did in just over four years, I think, is such an inspiring story, and David McCullough is a fascinating writer, so it's a really great read.

AI assessment note: “I love The Wright Brothers, which was written by David McCullough a couple years ago.”

Q So two questions, one stringing from that kind of all-in mentality, and the other with regards to the distributed workforce, starting on the all-in mentality, do you think then that that kind of concept of the side hustle really doesn't work today, and that you do have to be all-in 24 hours a day?

A Generally, yes. I certainly like people who have, you know, a creative side that flex their muscles beyond just what the day-to-day of the job entails, and so sometimes that's a positive signal, but I'd be a little bit wary about somebody who's got Too much of their time devoted to outside pursuits. I'll give you one example. We found and recruited an excellent contractor to work with our team based outside of the Bay Area, and he worked with us as a consultant for a while until we hired him on full time, but we made sure when we hired him on full time that we were compensating him sufficiently more than he'd ever been compensated so that we could, as part of that deal, say, could you take down your moonlighting business? We want you to be all in. Any extra hours and effort you can be giving, we'd love you to give to what we're doing here. So I think that's a bit of an issue, and when you're joining a startup, I do think you have to devote yourself to the long run. You can't build hoping for some quick win in the marketplace or quick outcome, and I think it was Patrick Collison I recently heard saying he was surprised how long it takes to build a successful startup, and he's leading Stripe, which is clearly as, it's an immensely successful startup in a relatively short period of time, but even he says, hey, this takes a long time of dedicated work, and I think we have to have t…

AI assessment note: “Generally, yes. I certainly like people who have, you know, a creative side”

Q So I always love to be optimistic, but there's always two sides to every equation. On the flip side, what's maybe increased in difficulty over the last decade?

A Well, I'd say a few things. One is ironically, some of the factors I just mentioned about having all these services kind of do it yourself to start and launch a company through its early stages. It actually, I think then puts a lot more dependency on a few team members in running that company where some of that was handled by other people in the past. So maybe you don't have an on staff bookkeeper or an accounting consultant as early in the company, but now you've got the CEO handling reimbursements or you don't have a retained recruiter, but now you've got the VP of engineering managing the company profile on a hiring web Site or things like that, And so there's some time and distraction that you have to consider. It's a bit of a drain sometimes now with that, but a major one is just the overall challenge in hiring for technical talent. It's just become more competitive. And one of the negative real challenges being here in the Bay area is the overall cost of hiring here. And that has been driven by that competition with the big tech companies, as we mentioned, as well as just the overall cost of living here in the Bay area. The last factor I'll say is that I think you had on recently, uh, James Currier talking about the shift in distribution to some more dependency on paid growth. And that's a, that can be a real challenge for startups if they're dependent on paid growth. We'…

AI assessment note: “Well, I'd say a few things. One is ironically, some of the factors”

Q And in terms of kind of turning on the jets, often in those kind of scaling cases, considerable funding is needed from the wonderful VCs of the world. You have the likes of Redpoint in Astro. I'd love to hear your thought process around taking multi-stage fund funds at such an early age. What are your thoughts on this? And for founders maybe contemplating it, what would your advice be?

A Well, there were two factors for us in that. One is that we believed what we were getting into in workplace communications was going to be a long play, that there are big players in this space that we partner with, as well as, you could say, kind of compete alongside, and those are Google and Microsoft, to name a couple, but there are many others as well that are also formidable and have great product offerings, and so we knew this was not going to be something Market in a year's time, and so we were going to need to put our heads down and work for quite a while, and having the funding to back that was important. We also had an existing strong relationship with Redpoint and Satish Dharmaraj at Redpoint, and we had a comfort in knowing that this is a firm that we very likely could grow with into the future, and that if we met our goals, that they would be interested to work with us as we went from seed to A round, and Hopefully well beyond that, and so those two factors caused us to say we'd like to go in deep and go ahead and commit ourselves to a long term, and this red point is an example of a firm's great to do that with.

AI assessment note: “there were two factors for us in that. One is that we believed”

Q beginning, and I hope my interview style has changed significantly because Guy was fantastic, but I was less than brilliant. I would love to start today on a little bit about you. You have one of the most interesting careers in the business from startups to wineries in Chile to large incumbents. So how did you make your way into tech and startups and then really come to found Astro?

A Well, after university, I spent a few years in the 19 nineties working for a nonprofit organization that was helping support the process of democratization that many countries in Southern Africa were taking at that time. So as part of that, I lived and worked about two years in Cape Town, South Africa, which was in the period shortly after the end of apartheid and when Nelson Mandela had been elected president in South Africa. But what I learned very quickly is that in a country where 80% of the population, primarily the black South Africans, were suddenly now free to vote and in theory to participate in all aspects of the country's development, the economy, politics, education system, in reality there were still huge barriers for most of the people to participate in a meaningful way. And at the time I didn't know anything about how economies or businesses worked, so I came back to the U.S. to go to grad school at Stanford. And after that, I joined a startup here in the Valley called OneBox as the first business person on the team. And the first person I met when I was interviewing was the engineering lead, Satish Darmaraj. Today is now our, our investor in my current company, Astro.

AI assessment note: “after that, I joined a startup here in the Valley called OneBox”

Q But I do quickly, I'm too intrigued in terms of that paid to organic. How do you think about that as a kind of a relationship and an equation and what signifies healthy versus unhealthy?

A Well, we try to do paid in a couple of ways. We try to never let it go beyond a certain portion, a very kind of low fraction of our overall attainment of new users. If it goes too high, uh, For any brief period of time, then that suggests that we're out of balance and we're not kind of focused on the right areas of our product growth and the product features and the appeal of the product itself. But we do use paid growth as well to try to test different messages and test different channels because there are going to be periods in our life that we really want to pour on the gas and where we feel like we've really got the product nailed and we've got the proposition and we simply need to get the word out. And so we do a lot of sampling and testing right now, Again, at a pretty modest spend, but it's important that we do that testing now so that we're really ready when we want to turn on the jets.

AI assessment note: “If it goes too high, uh, For any brief period of time, then that suggests”

Q that kind of element of distributed teams, can I just jump on one element there? What would you say is the biggest challenge that the incumbents pose? Is it kind of salary differentials, Is it career trajectory in terms of kind of having a very defined career trajectory? What do you think it is that they put? Is it data incumbency? What is it fundamentally that you think they pose?

A Well, I do think they have some interesting work to do. They're working on interesting projects, and you can tackle interesting things, although you do tend to work on it in a pretty minute way, so you're often working on one narrow aspect when you're in a big company of an interesting project, so I think that's a big difference versus a startup, and they have put more compensation toward team members in the Something they've done with their big reserves of cash. So that's a strong competing factor, but I don't think those are insuperable. We can't, not as though we can't overcome those as startups. It just makes for a bit stronger challenge than there was maybe 10 years ago.

AI assessment note: “So that's a strong competing factor, but I don't think those are insuperable.”

Q So two questions, one stringing from that kind of all-in mentality, and the other with regards to the distributed workforce, starting on the all-in mentality, do you think then that that kind of concept of the side hustle really doesn't work today, and that you do have to be all-in 24 hours a day?

A Generally, yes. I certainly like people who have, you know, a creative side that flex their muscles beyond just what the day-to-day of the job entails, and so sometimes that's a positive signal, but I'd be a little bit wary about somebody who's got Too much of their time devoted to outside pursuits. I'll give you one example. We found and recruited an excellent contractor to work with our team based outside of the Bay Area, and he worked with us as a consultant for a while until we hired him on full time, but we made sure when we hired him on full time that we were compensating him sufficiently more than he'd ever been compensated so that we could, as part of that deal, say, could you take down your moonlighting business? We want you to be all in. Any extra hours and effort you can be giving, we'd love you to give to what we're doing here. So I think that's a bit of an issue, and when you're joining a startup, I do think you have to devote yourself to the long run. You can't build hoping for some quick win in the marketplace or quick outcome, and I think it was Patrick Collison I recently heard saying he was surprised how long it takes to build a successful startup, and he's leading Stripe, which is clearly as, it's an immensely successful startup in a relatively short period of time, but even he says, hey, this takes a long time of dedicated work, and I think we have to have t…

AI assessment note: “Generally, yes. I certainly like people who have, you know, a creative side”

Q So I always love to be optimistic, but there's always two sides to every equation. On the flip side, what's maybe increased in difficulty over the last decade?

A Well, I'd say a few things. One is ironically, some of the factors I just mentioned about having all these services kind of do it yourself to start and launch a company through its early stages. It actually, I think then puts a lot more dependency on a few team members in running that company where some of that was handled by other people in the past. So maybe you don't have an on staff bookkeeper or an accounting consultant as early in the company, but now you've got the CEO handling reimbursements or you don't have a retained recruiter, but now you've got the VP of engineering managing the company profile on a hiring web Site or things like that, And so there's some time and distraction that you have to consider. It's a bit of a drain sometimes now with that, but a major one is just the overall challenge in hiring for technical talent. It's just become more competitive. And one of the negative real challenges being here in the Bay area is the overall cost of hiring here. And that has been driven by that competition with the big tech companies, as we mentioned, as well as just the overall cost of living here in the Bay area. The last factor I'll say is that I think you had on recently, uh, James Currier talking about the shift in distribution to some more dependency on paid growth. And that's a, that can be a real challenge for startups if they're dependent on paid growth. We'…

AI assessment note: “a major one is just the overall challenge in hiring for technical talent.”

Q kind of incumbents like VMware and Yahoo, and now founding companies. For someone entering the workforce who really wants to optimize for learning, which would you say is the most beneficial? Is it founding a company and learning by having to learn? Is it by kind of having a hand slightly held at a startup, or is it by learning from kind of true seasoned greats at big tech titans?

A You know, I think my answer on that has probably shifted in the past few years. I would have almost hands down before said, go ahead, get in that startup, or go to that medium-sized growth I think there's merits to all of them, but I would now lean more toward go to that medium-sized growth company. You know, if you can get in today at a company like Stripe or Slack, for example, I think you get incredible growth opportunities, and if you, you know, merit it, you'll get great opportunities to grow in your own career very quickly as well, and there's a lot to be said for some of the larger companies because they're increasingly well-managed. In some sense, I may be speaking against myself because, of course, we want to continue to recruit great people into startups like our own, But I think for the person just coming out, there are unparalleled opportunities now to learn in those growth environments and even some of the bigger companies.

AI assessment note: “I would now lean more toward go to that medium-sized growth company.”

Q And in terms of kind of turning on the jets, often in those kind of scaling cases, considerable funding is needed from the wonderful VCs of the world. You have the likes of Redpoint in Astro. I'd love to hear your thought process around taking multi-stage fund funds at such an early age. What are your thoughts on this? And for founders maybe contemplating it, what would your advice be?

A Well, there were two factors for us in that. One is that we believed what we were getting into in workplace communications was going to be a long play, that there are big players in this space that we partner with, as well as, you could say, kind of compete alongside, and those are Google and Microsoft, to name a couple, but there are many others as well that are also formidable and have great product offerings, and so we knew this was not going to be something Market in a year's time, and so we were going to need to put our heads down and work for quite a while, and having the funding to back that was important. We also had an existing strong relationship with Redpoint and Satish Dharmaraj at Redpoint, and we had a comfort in knowing that this is a firm that we very likely could grow with into the future, and that if we met our goals, that they would be interested to work with us as we went from seed to A round, and Hopefully well beyond that, and so those two factors caused us to say we'd like to go in deep and go ahead and commit ourselves to a long term, and this red point is an example of a firm's great to do that with.

AI assessment note: “there were two factors for us in that. One is that we believed”

Q kind of incumbents like VMware and Yahoo, and now founding companies. For someone entering the workforce who really wants to optimize for learning, which would you say is the most beneficial? Is it founding a company and learning by having to learn? Is it by kind of having a hand slightly held at a startup, or is it by learning from kind of true seasoned greats at big tech titans?

A You know, I think my answer on that has probably shifted in the past few years. I would have almost hands down before said, go ahead, get in that startup, or go to that medium-sized growth I think there's merits to all of them, but I would now lean more toward go to that medium-sized growth company. You know, if you can get in today at a company like Stripe or Slack, for example, I think you get incredible growth opportunities, and if you, you know, merit it, you'll get great opportunities to grow in your own career very quickly as well, and there's a lot to be said for some of the larger companies because they're increasingly well-managed. In some sense, I may be speaking against myself because, of course, we want to continue to recruit great people into startups like our own, But I think for the person just coming out, there are unparalleled opportunities now to learn in those growth environments and even some of the bigger companies.

AI assessment note: “I would now lean more toward go to that medium-sized growth company.”

Q But I do quickly, I'm too intrigued in terms of that paid to organic. How do you think about that as a kind of a relationship and an equation and what signifies healthy versus unhealthy?

A Well, we try to do paid in a couple of ways. We try to never let it go beyond a certain portion, a very kind of low fraction of our overall attainment of new users. If it goes too high, uh, For any brief period of time, then that suggests that we're out of balance and we're not kind of focused on the right areas of our product growth and the product features and the appeal of the product itself. But we do use paid growth as well to try to test different messages and test different channels because there are going to be periods in our life that we really want to pour on the gas and where we feel like we've really got the product nailed and we've got the proposition and we simply need to get the word out. And so we do a lot of sampling and testing right now, Again, at a pretty modest spend, but it's important that we do that testing now so that we're really ready when we want to turn on the jets.

AI assessment note: “We try to never let it go beyond a certain portion, a very kind of low fraction”

Q What did you not do well that you had changed in the way you presented the vision, in the way that you presented The team and the way that you kind of orchestrated the actual fundraise itself timeline-wise, is there anything you'd change?

A I think that the primary thing that we would change is consistent with how you want to run your business, which is the more narrow you can have of a focus on what your proposition is, the better that people can understand it and give you feedback on it, and the better that you can start to build your business. Having a relatively narrow focus You can almost always expand your scope from there. You can almost always expand the range of discussions that you have with investors, and you can almost always expand what you're building as well in the business. But if you go too broad, it can be hard for investors to understand. It can be hard for you and your team to actually get a focused product into market. So that's one thing I think is always important in a fundraising process. And there's another element which comes to how do you spend your money and how do you spend your time? And Michael Deering is a great quote that I've Really appreciated, which is he said a little while back that when you have a tissue box, it's full. You typically take one tissue for each blow. And then when your tissue box is getting empty, you start to get a lot more careful with the tissues. And the same thing happens with your time, with your energy and your finances as a company. You have to be thinking as if the tissue box is almost full for many of the decisions you make throughout the life of the c…

AI assessment note: “the primary thing that we would change is consistent with how you want to run”

Q that kind of element of distributed teams, can I just jump on one element there? What would you say is the biggest challenge that the incumbents pose? Is it kind of salary differentials, Is it career trajectory in terms of kind of having a very defined career trajectory? What do you think it is that they put? Is it data incumbency? What is it fundamentally that you think they pose?

A Well, I do think they have some interesting work to do. They're working on interesting projects, and you can tackle interesting things, although you do tend to work on it in a pretty minute way, so you're often working on one narrow aspect when you're in a big company of an interesting project, so I think that's a big difference versus a startup, and they have put more compensation toward team members in the Something they've done with their big reserves of cash. So that's a strong competing factor, but I don't think those are insuperable. We can't, not as though we can't overcome those as startups. It just makes for a bit stronger challenge than there was maybe 10 years ago.

AI assessment note: “they have put more compensation toward team members in the Something they've done”

Q If you reflect on your fundraising process, we mentioned that a number of the investors that you have involved in the journey. If you were to reflect, with the benefit of hindsight, what do you think you did well in the fundraising, and were there any elements that you'd maybe change for earlier rounds of Astro, or the next startup?

A Well, I think that one of the most important things that we were able to do was to focus early on on who were the Investors who are going to be able to give us the best insights and the best feedback. Ideally, these are investors, as we have, who have some knowledge of our domain and some expertise around it, and are willing to share their views, but then also recognize that they're no longer quite the experts that they might have been, or that we are on a day-to-day basis, and that there's so much evolution going on in any one space that the operating team of the company is Is going to need to be the real experts, and we can get that advice, and get that input, and we want them to have that domain expertise, so that's very valuable to us, but then they also know where to sort of stop and say, okay, we trust what we're hearing from you, we have given you feedback, and we can see it being incorporated, but we won't go beyond a certain point, because we know that you're the specialist in that, so that's been very helpful to us, to figuring that out from the beginning.

AI assessment note: “one of the most important things that we were able to do was to focus early”

Q What did you not do well that you had changed in the way you presented the vision, in the way that you presented The team and the way that you kind of orchestrated the actual fundraise itself timeline-wise, is there anything you'd change?

A I think that the primary thing that we would change is consistent with how you want to run your business, which is the more narrow you can have of a focus on what your proposition is, the better that people can understand it and give you feedback on it, and the better that you can start to build your business. Having a relatively narrow focus You can almost always expand your scope from there. You can almost always expand the range of discussions that you have with investors, and you can almost always expand what you're building as well in the business. But if you go too broad, it can be hard for investors to understand. It can be hard for you and your team to actually get a focused product into market. So that's one thing I think is always important in a fundraising process. And there's another element which comes to how do you spend your money and how do you spend your time? And Michael Deering is a great quote that I've Really appreciated, which is he said a little while back that when you have a tissue box, it's full. You typically take one tissue for each blow. And then when your tissue box is getting empty, you start to get a lot more careful with the tissues. And the same thing happens with your time, with your energy and your finances as a company. You have to be thinking as if the tissue box is almost full for many of the decisions you make throughout the life of the c…

AI assessment note: “the primary thing that we would change is... the more narrow you can have of a focus”

Q If you reflect on your fundraising process, we mentioned that a number of the investors that you have involved in the journey. If you were to reflect, with the benefit of hindsight, what do you think you did well in the fundraising, and were there any elements that you'd maybe change for earlier rounds of Astro, or the next startup?

A Well, I think that one of the most important things that we were able to do was to focus early on on who were the Investors who are going to be able to give us the best insights and the best feedback. Ideally, these are investors, as we have, who have some knowledge of our domain and some expertise around it, and are willing to share their views, but then also recognize that they're no longer quite the experts that they might have been, or that we are on a day-to-day basis, and that there's so much evolution going on in any one space that the operating team of the company is Is going to need to be the real experts, and we can get that advice, and get that input, and we want them to have that domain expertise, so that's very valuable to us, but then they also know where to sort of stop and say, okay, we trust what we're hearing from you, we have given you feedback, and we can see it being incorporated, but we won't go beyond a certain point, because we know that you're the specialist in that, so that's been very helpful to us, to figuring that out from the beginning.

AI assessment note: “one of the most important things that we were able to do was to focus early”