Even though I just joined the firm, I've been connectedto it for my whole career. At tumblr I had the privilege to join board meetings as a 22 year old where I watched and learned from Brad where he was a board director. That's when I learned that "good board members listen first, then talk." I have worked with Andy since 2010 when he became GroupMe's first lead investor at betaworks. For the past decade I've continued to learn from him on the board of Splice which was founded by my dear friend and longtime business partner, Steve Martocci, who is a two-time USV founder. So much of what I wrote about in this Helpful Boards post I picked up from working (and seeing Phish shows) with Andy for nearly 15 continuous years. Over the past year, I've been fortunate to spend time with Rebecca and Nick and see how they work with Founders - and I've listened to those Founders proudly sing their praises. I have also co-invested with USV in numerous startups and have been an LP since 2014. This is a special firm filled with remarkable people.
Earlier in my career I'd often look at people in the valley that I admired (ie Founders, CEOs and Investors) and wonder how they got where they were. What I've come to understand is that they were active participants in growing networks that constantly paid it forward and deeply invested in relationships over long periods of time. It's a very unique thing to come of age in a growing ecosystem. When I started at tumblr, most everyone in NYC tech could get together at the OG Shake Shack in Madison Square Park. The community was tight-knit and a lot of people who were actively engaged in it are still around today. I fondly remember how Steve and I would run around trying to meet smart people while carving out a space for ourselves as hungry entrepreneurs. A lot of the connections I made back then are some of the most special relationships I have now. In many ways, every opportunity I've had is a function of the relationships I've built along the way. And as this NYC (and now global) tech ecosystem has grown, so too has the surface area for fun and serendipitous things to happen.
I'm looking forward to this new chapter and continuing to invest in the relationships that make life fun and rewarding while building new ones with great people inside and outside this special ecosystem. Over the past year when I was prioritizing the things that were most important to me when considering what to do next, number one was making sure I was working with people I could continuously learn from and have a ton of fun with along the way. I'm lucky to make that a reality thanks to the entire team at USV and the important relationships in my life that have supported me on this journey.
Writing that feels weird, almost like confessing to a crime. AfterI left Fundera/Nerdwallet at the beginning of this year, I committed to taking 6-9 months of time with one rule: I couldn't make any decisions about what to do next. I had never taken an extended break before - I had always known what I was going to do next and let momentum carry me from one place to another. It generally has served me well, but I wanted to try something new in the hopes that a break would allow me to reset and give me more clarity and confidence.
Taking time off is most certainly a privilege. I did all the cliche things one does: travel, spend time with family, read, exercise, pickup old hobbies, spend time with friends, etc. All of that was absolutely wonderful. It was also genuinely shocking and borderline frightening how fast days would go by. But the downtime can also be extremely difficult. All I've known is forward motion and planning for what comes next, so this was unfamiliar territory (although, perhaps committing to clearing my head and making no decisions was preparing for what comes next).
I learned a lot about myself over the past year. I found that so much of my identity was tied up in what I did. Telling people "I'm taking a year off" was a really strange thing to do. It made me question who I was. My whole professional career I identified as a tech entrepreneur, and all of a sudden I was in between things.
One of the worst feelings in the world is having a sick child. Nothing eats at your heart and soul more than the feeling of helplessness that is watching your kid feel ill. Like all parents, I’ve had plenty of harrowing experiences with my children ranging from hospital stays with viral meningitis to a one year old turning into a blue balloon with serum sickness. Nothing makes me more sad and anxious than seeing one of my kid come down with a bug.
Another unfortunate thing about kids being sick is having to physically go to a doctor's office for just about everything. Some pediatricians do some form of telemedicine, many through Klara in my experience, but they'll seldom diagnose or prescribe anything without seeing the child in person. At first I thought it was understandable, but so many of these diagnoses are rather rote and can be done with a photo or video. The other downside of having to physically go into your pediatrician is that you can never see them when you want, which is always as close to Now as possible. The options are normally wait a couple days or make your way to urgent care. More often than not what a parent wants is to simply know that things are fine and that tylenol/ibuprofen are good for now.
Last year I learned of a service called Summer Health that enables you to text with a pediatrician 24/7. The communication is pretty much synchronous and I love it because it nearly instantly provides me peace of mind. Every time I text Summer I'm sent a link where I can view the credentials of the pediatrician I am speaking with, and I enter a real-time SMS conversation with them within minutes. I've talked to them at all hours of the day about things ranging from head bumps, questions about strep throat, how to remove excess silver nitrate on one of my kid's faces from a procedure at an ENT, whether you can administer antibiotics if they're expired but have lived in the refrigerator, what medications are okay to take with norovirus, how to know if your child is a carrier for strep, and many more things from the mundane to quite serious. They also call in prescriptions and frequently ask for photos or video to better understand a condition. All of my interactions have been pleasant. And while the doctors don't always nail the condition (eg maybe they think something is croup instead of another respiratory issue), I get an educated opinion quickly and know whether I can wait a day to take my kid in or if I should get a move on things. The service is roughly $20 per month which is an easy price for me to stomach paying for the peace of mind I get from it.
Even though I just joined the firm, I've been connectedto it for my whole career. At tumblr I had the privilege to join board meetings as a 22 year old where I watched and learned from Brad where he was a board director. That's when I learned that "good board members listen first, then talk." I have worked with Andy since 2010 when he became GroupMe's first lead investor at betaworks. For the past decade I've continued to learn from him on the board of Splice which was founded by my dear friend and longtime business partner, Steve Martocci, who is a two-time USV founder. So much of what I wrote about in this Helpful Boards post I picked up from working (and seeing Phish shows) with Andy for nearly 15 continuous years. Over the past year, I've been fortunate to spend time with Rebecca and Nick and see how they work with Founders - and I've listened to those Founders proudly sing their praises. I have also co-invested with USV in numerous startups and have been an LP since 2014. This is a special firm filled with remarkable people.
Earlier in my career I'd often look at people in the valley that I admired (ie Founders, CEOs and Investors) and wonder how they got where they were. What I've come to understand is that they were active participants in growing networks that constantly paid it forward and deeply invested in relationships over long periods of time. It's a very unique thing to come of age in a growing ecosystem. When I started at tumblr, most everyone in NYC tech could get together at the OG Shake Shack in Madison Square Park. The community was tight-knit and a lot of people who were actively engaged in it are still around today. I fondly remember how Steve and I would run around trying to meet smart people while carving out a space for ourselves as hungry entrepreneurs. A lot of the connections I made back then are some of the most special relationships I have now. In many ways, every opportunity I've had is a function of the relationships I've built along the way. And as this NYC (and now global) tech ecosystem has grown, so too has the surface area for fun and serendipitous things to happen.
I'm looking forward to this new chapter and continuing to invest in the relationships that make life fun and rewarding while building new ones with great people inside and outside this special ecosystem. Over the past year when I was prioritizing the things that were most important to me when considering what to do next, number one was making sure I was working with people I could continuously learn from and have a ton of fun with along the way. I'm lucky to make that a reality thanks to the entire team at USV and the important relationships in my life that have supported me on this journey.
Writing that feels weird, almost like confessing to a crime. AfterI left Fundera/Nerdwallet at the beginning of this year, I committed to taking 6-9 months of time with one rule: I couldn't make any decisions about what to do next. I had never taken an extended break before - I had always known what I was going to do next and let momentum carry me from one place to another. It generally has served me well, but I wanted to try something new in the hopes that a break would allow me to reset and give me more clarity and confidence.
Taking time off is most certainly a privilege. I did all the cliche things one does: travel, spend time with family, read, exercise, pickup old hobbies, spend time with friends, etc. All of that was absolutely wonderful. It was also genuinely shocking and borderline frightening how fast days would go by. But the downtime can also be extremely difficult. All I've known is forward motion and planning for what comes next, so this was unfamiliar territory (although, perhaps committing to clearing my head and making no decisions was preparing for what comes next).
I learned a lot about myself over the past year. I found that so much of my identity was tied up in what I did. Telling people "I'm taking a year off" was a really strange thing to do. It made me question who I was. My whole professional career I identified as a tech entrepreneur, and all of a sudden I was in between things.
One of the worst feelings in the world is having a sick child. Nothing eats at your heart and soul more than the feeling of helplessness that is watching your kid feel ill. Like all parents, I’ve had plenty of harrowing experiences with my children ranging from hospital stays with viral meningitis to a one year old turning into a blue balloon with serum sickness. Nothing makes me more sad and anxious than seeing one of my kid come down with a bug.
Another unfortunate thing about kids being sick is having to physically go to a doctor's office for just about everything. Some pediatricians do some form of telemedicine, many through Klara in my experience, but they'll seldom diagnose or prescribe anything without seeing the child in person. At first I thought it was understandable, but so many of these diagnoses are rather rote and can be done with a photo or video. The other downside of having to physically go into your pediatrician is that you can never see them when you want, which is always as close to Now as possible. The options are normally wait a couple days or make your way to urgent care. More often than not what a parent wants is to simply know that things are fine and that tylenol/ibuprofen are good for now.
Last year I learned of a service called Summer Health that enables you to text with a pediatrician 24/7. The communication is pretty much synchronous and I love it because it nearly instantly provides me peace of mind. Every time I text Summer I'm sent a link where I can view the credentials of the pediatrician I am speaking with, and I enter a real-time SMS conversation with them within minutes. I've talked to them at all hours of the day about things ranging from head bumps, questions about strep throat, how to remove excess silver nitrate on one of my kid's faces from a procedure at an ENT, whether you can administer antibiotics if they're expired but have lived in the refrigerator, what medications are okay to take with norovirus, how to know if your child is a carrier for strep, and many more things from the mundane to quite serious. They also call in prescriptions and frequently ask for photos or video to better understand a condition. All of my interactions have been pleasant. And while the doctors don't always nail the condition (eg maybe they think something is croup instead of another respiratory issue), I get an educated opinion quickly and know whether I can wait a day to take my kid in or if I should get a move on things. The service is roughly $20 per month which is an easy price for me to stomach paying for the peace of mind I get from it.
Ride It to the Sky
Ride It to the Sky
I went deep on a series of ideas that could have easily turned into startups. One was around programmatically enabling any company to build a world-class SEO program, another was a"roll-up" of internet businessesthat hadindestructible product marketfit around people's various passions, and another was onpreventing heart disease (which I will publish some more thoughts on soon because I'd really like to help someone accomplish this). I came within inches of starting one of them, but it was within my "No Decisions" window and I'm glad I stuck to it. The easiest thing for me to do would have been to start another company. It's all I've really known, and it's the thing that I most identified with. Not starting something during this period was very difficult.
I did my best to go with the flow and embrace the idea of wu wei to see where it would take me. I'm very happy with the process and thrilled with where my journey concluded. Next month I'll be tackling something new for me with a group of people I've long admired and respected. I'm equal parts thrilled and nervous. It's an evolution of what I've been doing, and I am eager to step outside of my comfort zone and embark on a new adventure. I don't think this opportunity would have emerged had I not sat still for a bit. After ample time off exploring, I feel like I have boundless energy to deploy. I'm ready to go.
Reflecting on the experience, these are some of my most important takeaways:
Hobbies bring great joy. I rekindled my love with tennis, joined a club, and hit 1-2 days per week. I'm playing at a 4.5-5.0 level with ex-D1 players and I love being competitive again.
The world is big and beautiful and should be explored in a variety of different ways if you can. Traveling to new places by myself, with family, or with friends was wonderful. I'm committed to adventure.
There's nothing better than quality time with family. I got a lot of it over the past several years and had the opportunity to watch my kids grow.
While working from home had its benefits, I am very over it. I need to be in an office with people making things happen. There's no substitute for it for me. People have different styles. Mine is in person. I also find that being in the office during the day makes me more present when I am home.
It's easy to mentally atrophy if the break is too long. I recommend time off to anyone who can do it. But 12 months is too long for me. Somewhere between 3-6 likely would have done the trick.
I entered this hiatus with a great deal of uncertainty. And while there's more clarity about some things, there are still countless unknowns. I'm looking forward to continuing to explore them, whatever they may bring.
I'm really interested in this space for a whole host of reasons. First and foremost it's a personal problem I have - I'm a parent of two children and they sometimes get sick. I also appreciate that I can instantly communicate with a real pediatrician over text. It's like being able to text a family member that practices medicine - it's an invaluable resource. The channel of communication makes it special along with the fact that it's a real human being.
There are two things about its future that intrigue me most. The first is whether I'd be okay chatting with an AI. One of the things I've been doing recently is cross-referencing things I'm learning or recommendations from doctors with ChatGPT and I've found that ChatGPT nails most every question succinctly. I'll sometimes start a medical search on google and end up on a research paper and find my answer (eg how would you calculate the dosage of this specific drug?), then I'll go to ChatGPT and get a nearly identical answer. The results are pretty astounding, so for me I do think I'd be perfectly fine communicating with some chat-based AI, especially if I know there is a human in the loop somewhere and I can ripcord to them. The second thing I'd like to see happen is a suite of remote diagnostic tools more broadly utilized and made available to every household. One of the reasons why pediatricians want you to come into the office is because they physically want to see your child so they can evaluate them with a stethoscope and otoscope. There's enough hardware out there now that should enable remote visualization of ears and throat and listening to breathing. It'd be a lot easier to stream or send a video of an ear canal, see an ear infection, and have antibiotics delivered to your door within hours than waiting 24 hours to see your pediatrician or in a waiting room for hours at urgent care. It's obvious that this is where the future of care will end up, it's just a matter of time (and not just for pediatrics but for all care). It's also important that this trend will make healthcare meaningfully more accessible to people all around the globe, even in the most remote parts of the world.
I'm very excited by these trends. It's incredible that something as simple as on-demand text based communications can change healthcare access and the healthcare experience. It's a great building block and entryway to a much broader world of healthcare, and I hope it advances quickly because it's going to help a lot of people and provide them much needed peace of mind when they need it most.
I went deep on a series of ideas that could have easily turned into startups. One was around programmatically enabling any company to build a world-class SEO program, another was a"roll-up" of internet businessesthat hadindestructible product marketfit around people's various passions, and another was onpreventing heart disease (which I will publish some more thoughts on soon because I'd really like to help someone accomplish this). I came within inches of starting one of them, but it was within my "No Decisions" window and I'm glad I stuck to it. The easiest thing for me to do would have been to start another company. It's all I've really known, and it's the thing that I most identified with. Not starting something during this period was very difficult.
I did my best to go with the flow and embrace the idea of wu wei to see where it would take me. I'm very happy with the process and thrilled with where my journey concluded. Next month I'll be tackling something new for me with a group of people I've long admired and respected. I'm equal parts thrilled and nervous. It's an evolution of what I've been doing, and I am eager to step outside of my comfort zone and embark on a new adventure. I don't think this opportunity would have emerged had I not sat still for a bit. After ample time off exploring, I feel like I have boundless energy to deploy. I'm ready to go.
Reflecting on the experience, these are some of my most important takeaways:
Hobbies bring great joy. I rekindled my love with tennis, joined a club, and hit 1-2 days per week. I'm playing at a 4.5-5.0 level with ex-D1 players and I love being competitive again.
The world is big and beautiful and should be explored in a variety of different ways if you can. Traveling to new places by myself, with family, or with friends was wonderful. I'm committed to adventure.
There's nothing better than quality time with family. I got a lot of it over the past several years and had the opportunity to watch my kids grow.
While working from home had its benefits, I am very over it. I need to be in an office with people making things happen. There's no substitute for it for me. People have different styles. Mine is in person. I also find that being in the office during the day makes me more present when I am home.
It's easy to mentally atrophy if the break is too long. I recommend time off to anyone who can do it. But 12 months is too long for me. Somewhere between 3-6 likely would have done the trick.
I entered this hiatus with a great deal of uncertainty. And while there's more clarity about some things, there are still countless unknowns. I'm looking forward to continuing to explore them, whatever they may bring.
I'm really interested in this space for a whole host of reasons. First and foremost it's a personal problem I have - I'm a parent of two children and they sometimes get sick. I also appreciate that I can instantly communicate with a real pediatrician over text. It's like being able to text a family member that practices medicine - it's an invaluable resource. The channel of communication makes it special along with the fact that it's a real human being.
There are two things about its future that intrigue me most. The first is whether I'd be okay chatting with an AI. One of the things I've been doing recently is cross-referencing things I'm learning or recommendations from doctors with ChatGPT and I've found that ChatGPT nails most every question succinctly. I'll sometimes start a medical search on google and end up on a research paper and find my answer (eg how would you calculate the dosage of this specific drug?), then I'll go to ChatGPT and get a nearly identical answer. The results are pretty astounding, so for me I do think I'd be perfectly fine communicating with some chat-based AI, especially if I know there is a human in the loop somewhere and I can ripcord to them. The second thing I'd like to see happen is a suite of remote diagnostic tools more broadly utilized and made available to every household. One of the reasons why pediatricians want you to come into the office is because they physically want to see your child so they can evaluate them with a stethoscope and otoscope. There's enough hardware out there now that should enable remote visualization of ears and throat and listening to breathing. It'd be a lot easier to stream or send a video of an ear canal, see an ear infection, and have antibiotics delivered to your door within hours than waiting 24 hours to see your pediatrician or in a waiting room for hours at urgent care. It's obvious that this is where the future of care will end up, it's just a matter of time (and not just for pediatrics but for all care). It's also important that this trend will make healthcare meaningfully more accessible to people all around the globe, even in the most remote parts of the world.
I'm very excited by these trends. It's incredible that something as simple as on-demand text based communications can change healthcare access and the healthcare experience. It's a great building block and entryway to a much broader world of healthcare, and I hope it advances quickly because it's going to help a lot of people and provide them much needed peace of mind when they need it most.
