20VC: How To Build True Human Relationships with VC Pre-Investment, Why Valuation Is Not The Only Term and When To Take Lower Offers & How To Approach Mental Health As A Founder with Jon Dishotsky, Founder & CEO @ Starcity

Jon Dishotsky is the Founder & CEO @ Starcity, the startup on a mission to make cities more affordable to everyone allowing you to live with great people in the city you love. To date, Jon has raised over $28m in funding for Starcity from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA and Kima Ventures in Paris, just to name a few. Prior to founding Starcity, Jon did over 3M square feet of commercial real estate transactions for clients including Optimizely, Cruise Automation, Weebly, Zenefits and many more. Before that he spent 8 years at the prestigious Cushman & Wakefield. Jon is also an active angel investor with investments in the likes of Remote, Fond and Savvy. In Today’s Episode You Will Learn: 1.) How Jon made his way from doing real estate transactions for clients including YC to being one of the hottest prop tech startups making cities affordable with Starcity? 2.) Why did it take so long for the venture ecosystem to get excited by the rise of proptech? What was the catalyst? When advising VCs, how do you advise them to get comfortable investing in these heavy asset, non-lean startup businesses? What are the biggest mistakes investors make when analysing proptech? 3.) What were some of Jon's biggest takeaways from his time at YC? How does Jon advise other founders looking to get into YC today? When it comes to investor selection, in what cases would Jon take a lower valuation against other offers? How does Jon advise founders on investor selection? What questions should they ask? Why is it like hiring? What are the common mistakes that Jon sees founders make when selecting investors? 4.) How does Jon advise founders when it comes to improving the quality of their mental health? Where do Jon struggle? How does Jon engage with social media knowing the psychological effects it has? What have been some major breakthroughs for him? Why does Jon believe having kids has made him a better founder? Why does Jon believe that older entrepreneurs are actually more successful than younger founders? 5.) What is Jon's biggest advice to founders when it comes to building relationships with VCs? Should founders "always be raising"? How transparent should founders be with VCs both in the relationship building process and the fundraise itself? As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is Founders Friday on the 20 Minute VC with me, Harry Stebbings. It would be awesome to welcome you behind the scenes on Instagram at HStebbings1996. Have to admit, it's largely an array of mojito and gym videos these days, but I would love to see you there. But to our episode today, and I'm delighted to welcome a friend and phenomenal founder in the form of John Dyschowski. Now, John is the founder and CEO of Star City, the startup on a mission to make cities more affordable for everyone, allowing you to live with great people in the city you love. And to date, John's raised over $28 million in funding for Star City from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA, and Chima Ventures in Paris, just to name a few. And prior to founding Star City, John did over 3 million square feet of commercial real estate transactions for clients including the likes of Optimizely, Cruise Automation,

• 0:45Harry Stebbings?

  Weebly, Zenefits, and many more. And before that, he spent eight years at the prestigious Cushman and Wakefield. And John's also an active angel investor with investments in the likes of Remote, Fond and Savvy, just to name a few. I do also want to say a huge thank you to two fantastic previous guests in the form of Austin at Lambda and Jesse at Lumi for the fantastic intro today. I really do so appreciate that, and mojito's on me for that. But before we dive into the episode today, I'm always focused on scaling my time, and I was always crap at travel booking and management. Well, not anymore. Why? Because I now use TravelPerk, the business travel management platform that even I love. It's just so super easy to book travel and actually quite fun. And my favorite, no back and forth with travel agents or your finance team, but it gives you the best of both worlds. Companies don't just get happy travelers, but also easier management

• 1:30Harry Stebbings?

  and as much as 20% in savings with 100% in compliance. Got to tick that compliance box these days. And even better, no one is going to chase people for receipts or worry about splurging on overly expensive penthouse suites. Finally, I have to say, the support is just number one rated. So you get 24/7 travel experts ready to deal with forgotten passports. Yep, I had that one before. Unexpected flight cancellations, oversized baggage requests, vegan meal options, whatever you can think of, they have you covered. And the 20 Minute VC listeners can score a free lounge pass to over 1,200 airports for a whole year. That's quite astonishing. I'm quite jealous. I quite like that. All you need to do is go to travelperk.com/20vc. That's travelperk.com.

• 2:10Harry Stebbings?

  Forward slash two zero VC, give them the name of the person who runs travel at your company and if they book a demo, the lounge pass is yours. And if TravelPerk allows me to scale my time, a lot of what we do on the 20 minute VC is discuss scaling businesses, talk to experts, pick the brains of founders and investors who tell us about the trends to watch out for, offer tips on fundraising and teaches how to excel at any company stage. But there's no playbook for building a great business, but we can certainly learn from people who've done it before. Beyond listening to this podcast and talking to mentors and advisors in your own network, it's important to have resources you can turn to when you're tackling a new challenge. And Stripe has built those resources for you, whether you'd like to learn how to run a pricing experiment or build a knockout landing page. Stripe gives you the information you need to start, run and scale a technology company.

• 2:54Harry Stebbings?

  And their guides are often written by or feature people like Elad Gil, experts in their space who you've probably heard on this very podcast. And you can read my favorite guide on scaling engineering organizations and many more on Stripe.com forward slash twenty VC, that's T W E N T Y VC. And last but by no means least, to scale, you need customers and Intercom offers a new and better way to acquire, engage and retain customers. They've built a suite of messaging first products from chatbots to a totally reimagined business messenger that modern internet businesses use to accelerate growth across the customer lifecycle from acquisition to engagement and support. And over the past eight years, they've totally reimagined what a business messenger can be, which is way more than simply live chat.

• 3:35Harry Stebbings?

  Today, Intercom is used by the world's most forward thinking companies, 84% of Y Combinator companies that use a messaging or live chat tool use Intercom, astonishing fact that one, and they have over 30,000 customers, including larger companies too, like New Relic, Atlassian and Shopify, and also smaller companies like Airtable and Coda. But you've heard quite enough from me, so now I'm very excited to hand over to the wonderful John Dishotsky, founder and CEO at Star City.

• 4:05Speaker 01

  You have now arrived at your destination.

• 4:08Harry Stebbings?

  John, I am so excited for this episode. A huge thank you to Austin at Lander and Jesse at Lumi for the intro, but thank you so much for joining me today, John.

• 4:16Speaker 02

  Oh, I'm so excited for this, Harry. I'm a huge fan of yours and you've just got this lovely, good old fashioned thing I call hustle. So, congrats on all your success and excited to be here today.

• 4:25Harry Stebbings?

  Oh, you are so kind and what a way to butter me up at the beginning, but I would love to kick off with a little bit on you. So tell me, did you always kind of dream of recreating how we think about living in our cities? And what was that real founding moment with Star City?

• 4:38Speaker 02

  Yeah, so my parents eloped from the East Coast in the 1960s to San Francisco, California. And this was like during the middle of the counterculture hippie movement. And so they did live on Communes, but eventually settled in Palo Alto. My dad was pursuing a medical degree at Stanford and they ran a little experiment on our small family, which was that they had Stanford students living with us. So this was kind of co-living Sid 0.1. And it was impactful for our family because the students got a cheap place to live. My parents got inexpensive childcare and my brother and sister and I had all of these people from around the world living with us. And we had Stanford engineers helping us win every science fair project. This was a hack of ours. But I really fell in love with, with sort of cities when we went back to visit family in Manhattan.

• 5:22Speaker 02

  And I remember just sort of staying up one night when I think I was like seven or eight, just looking at the city skyline. And I think every drawing I did after that at elementary school was of a building or of a city. I fell in love with sort of entrepreneurship when I graduated college and reconnected with a good old friend of mine, Triv Adler, who had started a company, Script. He was in the second batch of Y Combinator and called me, he's like, hey, John, I know you do real estate related stuff. Can you help me build out a new office? And I was like, sure. From there, you know, I met the Weebly guys, I met the Optimizely guys, I met Parker from Zenefits. And along the way, I really just sort of saw them be able to grow these companies from zero to these amazing things. And I knew I wanted to do that, but I didn't know what my thing was going to be.

• 6:04Speaker 02

  So in 2015, I resigned from my career and the headlines about cities being so unaffordable had just started to really grind on me. And I reconnected with that experience of being a kid in this sort of like multi-generational, multi-diversity group of people living in a, under one roof. And thought that that could be a thing that really helped make cities more affordable. For a whole subset of people. And so that was sort of the moment where the sort of light bulb where I said, okay, let's build a product that makes cities accessible to everyone versus it only being available to a select few.

• 6:41Harry Stebbings?

  I absolutely love that. And I have to say, one thing I always look forward to today when I invest is I found a market fit. And so hearing those kind of early days at Stanford with the different students is awesome to hear. But I do want to separate the show into two different parts, the tangible and the intangible. Does that sound okay to you?

• 6:57Speaker 02

  Sounds awesome.

• 6:57Harry Stebbings?

  Okay, so with the tangible in mind, I want to discuss funding. You know, the proptech space is, it's not had the most love from VCs over the past few years, but it's suddenly become a very hot space. Can I ask, why did it take so long for proptech to become hot with VCs?

• 7:12Speaker 02

  Yeah, it's a great question. I think it comes down to really like, will they be able to provide returns to their LPs? And you know this now, there's a fund manager. And so it was really kind of like, what are the established companies that have grown to be multi-billion, tens of billion dollars? And so it kind of took a while, like, you know, Airbnb can kind of be considered a proptech company, but it's more of a marketplace. And I think WeWork was the first one that really sort of set the stage. Before that, there was really only like LoopNet and Zillow and Redfin. And, you know, those were really taking a very, you know, web 2.0 approach to proptech of just being sort of like a website and things like that. But I think it was really WeWork that sort of set the tone for proptech to really get to where it is today.

• 7:54Speaker 02

  And also I think it's, you know, there's the two sides of the valley, right? There's the side of the valley that says, look, we're only going to do the traditional VC stuff. And then there's the other side of the valley that says like, look, building another social media app is just going to get blown up by Facebook or Instagram because they're going to launch a feature and that company will be dead. And so just because all the FAANG companies can knock companies out of their seat, more of the traditional VCs are sort of like, let's just continue to do stuff like that. Whereas there's another side of VC which is like, okay, all of those startup ideas are taken. Let's try other markets. Let's try transportation. Let's try logistics. Let's try real estate. Let's try construction. Let's try some more of the gritty, harder problems. And so I think that like

• 8:38Speaker 02

  More people are sort of warming up to that second side.

• 8:41Harry Stebbings?

  Now, can I be a super contrarian with you? And as a VC, at first glance, one could look at Star City, and obviously not me, because I'm incredibly open minded as a VC, but they could look at it and say, "Oh, it's really asset heavy. No, thanks." Why would I or that VC be wrong in this case to take that automatic view that asset heavy, counter lean startup offering? And why would that be a wrong view?

• 9:04Speaker 02

  Yeah, so we didn't really approach the problem from looking at what would VCs think from the outset. We sort of said like, "Let's build the best thing we possibly can and then see what part of the capital markets would actually be open to helping us scale." And so we started the company by talking to 750 people who were making 50 to 120,000 dollars a year, who had full time jobs and were living in cities 20 to 50 years old. And we said, "What do you hate about your apartment? What do you hate about the living experience?" And obviously, after that, going through that, we found that there was a real hair on fire situation for that demographic. So then we talked to the supply side, and these were like real estate developers and builders and things like that. And we found that nobody was really focused on this problem. And so then we said, "Okay, we now have to build our first Star City, right?

• 9:48Speaker 02

  This is co-living as we see it, so our MVP." And what I did is I went out and I raised friends and family money in order to do that. And I built my founding team. Along the way, I reconnected with Tripp. Tripp was the founder of Script, and he was like, "Look, I can introduce you to VCs." And I was like, "Well, I don't know that VCs will really be excited about this." And then I met with Jared, his co-founder, who is now a partner at YC. And so I pitched Jared in this cafe, and this is in 2016. And he was kind of quiet at first, and I was like, "He hates this. He hates this idea." And he sort of stood up in this coffee shop, and he's like, "You have to apply to Y Combinator. You have to apply to Y Combinator." And I was like, "Whoa, okay." And I asked him why. He's like, "Look, this is a huge problem.

• 10:30Speaker 02

  The affordability of cities is a massive problem, and the size of this market is enormous. And you're building a new product, and no better place in the world to build a new product than Silicon Valley. And you will get people to get on board with you as long as you have that sort of MVP startup mentality of iterating and building a great product." And so I think what we found was that the PropTech thing was happening, VCs were warming up to a little bit more of the asset-heavy type of companies. And there's no other way to solve this problem than to build buildings, right? So, you know, that's how we kind of looked at it.

• 11:02Harry Stebbings?

  Can I jump on the YC element there? Because it's super interesting for me in terms of kind of your learnings going through that process. So what did you learn from your time there that you'd really recommend to other founders who maybe are applying today or interviewing soon? That you could pass on the wise wisdom?

• 11:17Speaker 02

  Yeah, you know, I'm a huge, I drink the YC Kool-Aid. I had so much admiration along the way after having met so many YC founders. Just the level of care and concern that YC really has for founders. And so, you know, I think what I tell people who are applying and interviewing is, is really just be yourself. Do not try to build a company that you think other people will like. Because you'll get so out of sync with yourself and you won't be able to pitch it the right way. And it has to be something that you really deeply care about. And so when you're applying and interviewing, just do that and hopefully that will resonate. The other thing that I would really recommend is that, it kind of goes back to that first point, but you're going to get a ton of advice along the way. Do the sort of analogy of like being shoved off of a cliff and having airplane parts.

• 12:01Speaker 02

  And the advice is people with older planes flying by you and telling you what to do. And so you're like, well, I'm building a different version of the plane. And you have to build it before you hit the ground flat. And so YC can definitely be that way, right? Where you have all these partners who are trying to help and then you have, you know, part-time partners and then you have other YC founders and then you have your peers. And so really what it comes back to is saying like, okay, well, what is true for me and what is true for my customer? What is true for our co-founding team? And really try to not optimize on the average of all that advice, but really take in just the good and the bad, but take it and do it your way. And I think that's really, really important. Otherwise, you'll end up with a sum of a lot of mediocre advice.

• 12:42Harry Stebbings?

  I totally agree with you and you can get lost in pitching someone else's idea of what your product should be. Totally with you there. As an investor, a common cause of upset there amongst that community with YC companies is the valuations. And we chatted before about valuations and how to think about them. And I'd love to hear your thoughts on when it comes to valuation. And kind of investor selection. In what situation, John, would you maybe take a low evaluation against other offers?

• 13:05Speaker 02

  I think the valuation thing is really funny in the early days, right? Like, I think Gary Tan from Initialise actually had a tweet recently about this. It's like, if you're trying to value invest at the seed stage, it's kind of a silly exercise. So I think that optimizing between a six cap and a 12 cap is really, I just don't know that that's going to be the right way to invest. I think you're just kind of like, is this going to be an enormous company? Let's go or let's not go. What a lot of founders forget is that you put somebody on your board, you have an investor that you really want to have this really deep connection with and close conversation with all the time. Because they're going to be there through all the ups and downs. And especially as the CEO, you're really beholden to the board and you want to make sure that the investors have a lot of confidence in you.

• 13:46Speaker 02

  So if that relationship isn't really good, then you can run into a lot of pitfalls. And so what I see a lot of founders do is they'll end up taking a valuation that, you know, a partner just because of a name or whatever it is and not really doing a diligence. And so you want to kind of think of it as hiring. So in our case, there's multiple times in our fundraising process where we had some of the folks with the sort of big names come to us. And in one instance, actually had a guy, a partner yell at us on like a pitch call. And I was like, if you're going to be this way when we're pitching you, what would it be like to actually work with you? And so in the end, actually, we took on the folks from Eric Wazan from Bullpen Capital. And I'm just a huge fan of Bullpen Capital and what Paul has built over there.

• 14:30Speaker 02

  Their offer was a little bit lower and they were sort of very transparent. But I said, like, look, I would love to be in the trenches with Eric for the next 10 years. He's just such a nice guy. He's so objective. And so in that instance, I think it's really important to think about, yes, you might get a higher valuation, but is this partner on the other side can really be there for you through the ups and downs? And how are they behaving in the fundraising process such that you can get a sense of what that relationship will look like?

• 14:54Harry Stebbings?

  No, I totally agree in terms of kind of getting a freemium model during the fundraising process. But the thing that concerns me honestly today, John, and it may be a VC perspective, but it's this kind of efficiency around fundraising processes where it's like, we'll do two weeks, we'll meet every investor in these two weeks, and then we will choose the term sheets. And it's like, so you're going to choose someone who you've met three days ago, who's given you a high valuation on a term sheet, and they're going to join your board and work with you for 10 years? And you're going to do that for efficiency's sake? That seems quite crazy to me. Am I wrong in thinking this? Am I too VC in thinking this?

• 15:27Speaker 02

  Look, I think you're tapping into something really interesting, which is just like before this, we were talking about relationships and love and Harry's in Harry's relationship world. And that was, that was very fun. We won't get into that now, but you know, you want to think of this exactly the same way. You may have love at first sight with an investor and that's okay, but you still want to do your diligence, right? And so I think that it's important to run a process and actually as a founder, you should know that you do have leverage in that process. And furthermore, those investors are professional investors and so they should be ready to participate in your process. So then you can get back to work and continue to work on your startup.

• 16:04Speaker 02

  A lot of the common pitfalls that I like to talk about are just preparedness, like not having your shit together as you're getting ready to fundraise. And what people often do is they just start fundraising before they've actually talked to partners. They haven't built any relationships with any partners. They just kind of say, look, it's time for me to raise. I'm gonna build a deck and I'm just gonna go out and do it. But without sort of soft pitching people throughout a series of meetings, you know, you really don't get a chance to build that relationship. And your chances of success are just so much lower. Whereas I think you should just always be building fundraising relationships and then you're in fundraising mode. And so the sort of traditional Silicon Valley approach is to say, I'm either in fundraising mode or not.

• 16:46Speaker 02

  But you know, I think that if you want to really build a relationship and look at that investor as your peer, you have to consider that they like, the more information they have, the more they get to know about you, the more they like you or don't like you, whatever it is. You'll get to a fast yes or a fast no in a way better fashion. I see a lot of founders just try, you know, avoid that totally.

• 17:05Harry Stebbings?

  And John, thank you for skimming over the atrocity that is my love life there.

• 17:11Harry Stebbings?

  But when we chatted before, we also had a discussion on less tangible elements and I would like to touch on some of those. One of them was mental health, an area that we often see more and more in the news today. So starting on that and maybe an element of causation, why do founders forget about this part during that journey as an entrepreneur, do you think?

• 17:29Speaker 02

  Yeah, so look, I have to say that I'm not a qualified therapist, but I was raised by a psychiatrist, my father. is something that our family really talks a lot about. He had a nickname, actually, his nickname was Warm Norm because he had this, just like he was such a warm guy and like, he is a warm guy and he had a hot tub that everybody would hang out in and just ask for advice. So anyways, all I want to say here is that like, I think that there's, and actually have to give kudos to the initialized guys for taking down the notion of sort of hustle porn, as I would say. There's this concept in the valley that like you should just grind to the limits of your existence and think about yourself secondarily and just really like focus on the product and build an awesome startup and all that kind of stuff.

• 18:12Speaker 02

  And I think that like what we found is, or at least is what the founding community has found is that they end up, even if there's a great outcome, having really not enjoyed the experience along the way. And so what you have to do is actually reprioritize yourself as number one, right? And this is kind of hard to do because you have so many people asking for so much stuff. And as a founder, you're probably really deeply care about solving people's problems. And so what you do is you sort of forget about yourself. So what I like to do, the trick is to just sort of like start first with really caring about yourself. And why that's important is that if your mental health and your, even your physical health is in a great place, that permeates to your entire company. If you're in a good mood, if you come in and you show up to every meeting and you're in a good place, if you're prepared, if you've sort of exercised that day, if you're in a really good place,

• 18:57Speaker 02

  that then brings excitement to your team and they're sort of, you're in a good mood and all that kind of stuff. And that has a cascading effect to the rest of the company. If you don't, if you put yourself last, you're going to start to see the sort of opposite, where your mental health is a disability, where you're down on yourself, you're not taking care of your health, you're sort of eating crappy food, maybe you're drinking every night or whatever it is. And then you, you know, the first thing you do in the morning is have nine cups of coffee. So you're like very jittery. And that then permeates to your company. And so what you have to understand is that you can do it that way, but it's going to have cascading and unfortunate effects on your company. And I think that if I talk to younger founders now, I always talk about this. And, and I think it's something that we just don't spend enough time on and I think we should be talking more about it.

• 19:41Harry Stebbings?

  All right, John. Okay. I'm a young founder in many respects and I'm exactly the image that you gave there. Maybe a drink once or twice an hour. Coffee's in the morning. That absolutely is me. Like, what advice would you have for me? How can I, not gamify, but how could I achieve some balance and stabilization?

• 19:59Speaker 02

  Like, you've got to find your sort of mental health coaches. I think that, like, there's nothing wrong with actually going to therapy. I think it has this stigma, but it really is mental health exercise. And I think that there's nothing wrong with it. And you should also be physically exercising. The other thing you can do is look at other founders as your sort of support group that are in your stage at that given time. That's really, really helpful and important to be able to share with folks about that. And then the other thing is just to say, like, you know, starting with gratitude, and I know, you know, Justin Khan talks about this very publicly, and I really appreciate that, is saying that, like, you have a choice every day to be really grateful. You decided to start this company.

• 20:38Speaker 02

  You're taking everybody on this journey. So you sort of have to really be intentional. And I think the thing that I really love to do is this daily gratitude journal, and that's waking up every single morning and saying, like, look, we have so much cool stuff around us. We live in such a wonderful city here in San Francisco, despite what the headlines might say. And I have a lovely family and a daughter, and like, these are things that I'm very, very grateful for. And there's, it goes on and on and on. And so if I were you, I would really start with that journal as a step one, building that support group, investigating therapy on your own terms, and sort of building that sort of mental health support group, so that you can always be in that positive frame of mind. And don't forget to exercise. And also, you know, the other thing is, you should definitely find a romantic partner. That's very important.

• 21:23Harry Stebbings?

  That's awesome, John. I've just adopted you as my therapist. So, uh, welcome for that one. I'm interested, you said there about your lovely wife and your children, so I'd love to ask, in terms of founder age, and I wanted to posit this in as gracious and nicer way as possible, but we have quite a 20-year-old Stanford dropout, and then there's slightly more seasoned founders in their midst with wives and kids and husbands. So is it actually better to be the older entrepreneur, or do we have the stigma for a reason?

• 21:50Speaker 02

  Yeah, I'm glad you said seasoning, because food is terrible without seasoning. And so if you're calling old seasoning, I'm down for that. That's okay. Look, you know, we were talking about this before, but like I get home from a hard day and I put my phone down and my daughter jumps into my arms and my wife is done with her work day. The day just sort of slips into this sort of meditative, different experiences, alternative universe, I like to call it. Where your day kind of slips behind you and now you're in a whole different world and you're with family and you're just sort of having a lot different conversations. And I think that this actually provided me a lot of value as a founder and leader because otherwise, and you know this, Harry, you're on 24/7.

• 22:34Speaker 02

  And I just don't think that that's how we're wired. You can do it for a short period of time. It's certainly okay, but I just don't think that that's how we're wired. We need to reset, right? We need the chance to wash out what happened in our memory in that day and really get some distance on it. And so I think that once you have a family and kids, you actually get this wonderful opportunity to have that time. I think the other thing is that 20 year olds, you know, sort of post-college John, might have been a little bit more ego-driven, maybe a little bit less humble. And after having been through a lot of ups and downs, not saying that I had a ton of hardship, but I'm just saying I'm a little bit more humble than I otherwise would be and a little bit less emotionally reactionary. And so as a mid-30s founder, I look at problems in a sort of a less ego-driven way and more of a team approach.

• 23:19Speaker 02

  And I think that that's really important as a leader. And then also sort of sharing your humility and humbleness and knowing that that's not a weakness. That vulnerability actually helps with feedback and people in your company and things like that, be a little bit more honest and truthful. And so I think that if I had just sort of been a 20-year-old right out of college, I would have had those tools or known that that was okay. I would have just sort of been operating on this sort of like more of a youthful bent, you know, more ego-driven. And so I prefer having to start it now. And I actually think that the statistics are in our favor. The seasoned guys and gals are actually better performers in many cases, so.

• 23:56Harry Stebbings?

  No, they are. The stats do prove you right. And I totally agree. One big learning for me is exactly as you said there, kind of vulnerability. Actually just deepens relationships and makes them way more real. So no, I totally agree with you there. But I would love to move into a quick. My favourite, as you know, I essentially seep you for all your knowledge in sixty seconds per question. Are you ready to dive in?

• 24:15Speaker 02

  Let's do it.

• 24:16Harry Stebbings?

  Okay, so I'm flying to the west coast. What book should I be reading on the plane and why?

• 24:21Speaker 02

  I'm actually, I like the classics. Nineteen eighty-four George Orwell, that really did it for me. It was also the year I was born.

• 24:28Harry Stebbings?

  What would you most like to change about Silicon Valley and tech today, really being in the epicentre of it today in SF?

• 24:33Speaker 02

  Yeah, I think that more female founders, more female VCs, more diversity inclusion, and then also more conversations around mental health. I think it's not discussed and it should be top of mind for everybody.

• 24:47Harry Stebbings?

  What can founders do to build the best relationship with their investors?

• 24:51Speaker 02

  I think that people don't use their gut enough. You know, we have this really great tool. People sort of throw out the window. When I'm looking to hire people or investors or anything like that, I use sort of competency, culture fit, and that this thing called chemistry. Chemistry is extremely important and people just forget about it. And in the real world, if somebody made you feel icky or weird, you would just avoid that. But for whatever reason, we don't do that in the business world. And I think that that's an extremely important skill for us to all all learn. And so do that with your investors. If you feel good or bad with them, I think you should recognise that.

• 25:22Harry Stebbings?

  What keeps you up at night, John?

• 25:24Speaker 02

  Oh, well, we're sleep training my daughter again. And so that's a wild ride for any fathers and mothers out there. So my daughter, there's your answer.

• 25:33Harry Stebbings?

  Love it. What advice do you hear, given most often, that you maybe disagree with?

• 25:38Speaker 02

  Yeah, I think actually the thing about fundraising, being in fundraising mode or not, I just don't think that's how you build relationships. Like being transactional on the thing that you care most or second most about your startup, with the people that are going to give you the money to help you get along the way and give you the advice along the way. I just don't think that that can, like you said, happen in two or three weeks. I think it's building a long-term relationship. It's just fraught with so many disadvantages. So that's the thing that I really try to push back against.

• 26:06Harry Stebbings?

  So aligned with you on that. And then the final one, John. Next five years for you in Star City, like just how big could it get?

• 26:13Speaker 02

  Yeah, so we want to be the brand that is recognised for Making cities affordable and accessible to people again. And I think that the world is our oyster. Right now, there is so many cities that people really want to get their foot in the door to, whether it be San Francisco to start a startup, whether it be LA to produce a movie or whatever it is. But maybe they have to be a barista or a bartender first to get there. They can't uncrack those cities because it's just so far out of reach and they can't get close to those places of action. And so we would love to be the globally recognized brand for people getting that foot in the door in the best cities in the world. And so we're actually building the buildings, we're actually building the community,

• 26:56Speaker 02

  we build software to make that experience really great. And so taking a holistic view, soup to nuts of like, what is the customer experience of moving to a new city? We would love to just be known as that. And then that kind of fundamentally goes down to hope. So if you're in the middle of the country and you've always had this dream of moving to one of these great cities, well, if you're looking at the headlines today, you say, I can't do that. Fast forward five to seven years, that same person could say, I can now do that because of Star City. That's my dream.

• 27:24Harry Stebbings?

  I think that's incredible. And I have to say, John, seriously, one of the biggest joys for me of doing the show is meeting like awesome people who you have great conversations with, great fun with too. The chemistry comes into play. And really, episodes like this make me realize that. So thank you so much for joining me today and I just really appreciate it.

• 27:41Speaker 02

  Yeah, let's find you some love, man. Let's try to do that. All right, dude, I really appreciate it. Thank you so much.

• 27:49Harry Stebbings?

  I mean, that is a true friend, hey, a wingman. But I do want to say a huge thank you to John for giving up the time today to be on the show. If you'd like to see more from John, you can find him on Twitter at John Dishotsky. It would be great to see you behind the scenes here. You can do that on Instagram at H Stebbings 1996 with two Bs. But before we leave you today, I'm always focused on scaling my time and I was always crap at travel booking and management. Well, not anymore. Why? Because I now use TravelPerk, the business travel management platform that even I love. It's just so super easy to book travel and actually quite fun. And my favorite, no back and forth with travel agents or your finance team. But it gives you the best of both worlds. Companies don't just get happy travelers, but also easier management and as much as 20% In savings with a hundred percent in compliance. Gotta tick that compliance box these days.

• 28:33Harry Stebbings?

  And even better, no one is going to chase people for receipts or worry about splurging on overly expensive penthouse suites. Finally, I have to say the support is just number one rated. So you get twenty four seven travel experts ready to deal with forgotten passports. Yep, I had that one before. Unexpected flight cancellations, oversized baggage requests, vegan meal options, whatever you can think of, they have you covered. And the twenty minute VC listeners can score a free lounge pass to over twelve hundred airports for a whole year. That's quite astonishing. I'm quite jealous. I quite like that. All you need to do is go to travelperk.com forward slash twenty VC. That's travelperk.com forward slash two zero VC. Give them the name of the person who runs travel at your company.

• 29:11Harry Stebbings?

  And if they book a demo, the lounge pass is yours. And if travel perk allows me to scale my time, a lot of what we do on the twenty minute VC is discuss scaling businesses. Talk to experts, pick the brains of founders and investors who tell us about the trends to watch out for, offer tips on fundraising, and teach us how to excel at any company stage. But there's no playbook for building a great business. But we can certainly learn from people who've done it before. Beyond listening to this podcast and talking to mentors and advisors in your own network, it's important to have resources you can turn to when you're tackling a new challenge. And Stripe has built those resources for you, whether you'd like to learn how to run a pricing experiment or build a knockout landing page. Stripe gives you the information you need to start, run and scale a technology company.

• 29:51Harry Stebbings?

  And their guides are often written by or feature people like Elad Gil, experts in their space who you've probably heard on this very podcast. And you can read my favorite guide on scaling engineering organizations and many more on stripe.com forward slash twenty VC. That's T W E N T Y V C. And last but by no means least, to scale, you need customers. And Intercom offers a new and better way to acquire, engage and retain customers. They've built a suite of messaging first products from chatbots to a totally reimagined business messenger that modern internet businesses use to accelerate growth across the customer lifecycle from acquisition to engagement and support. And over the past eight years, they've totally reimagined what a business messenger can be, which is way more than simply live chat.

• 30:32Harry Stebbings?

  Today, Intercom is used by the world's most forward-thinking companies, eighty four percent of Y Combinator companies that use a messaging or live chat. That tool, use Intercom, astonishing fact that one. And they have over 30,000 customers, including larger companies too, like New Relic, Atlassian and Shopify, and also smaller companies like Airtable and Coda. As always, I cannot thank you enough for your support and I can't wait to bring you one of my favourite 20 VCs with a VC on Monday. It's a very special one, so stay tuned.