This Week in Startups - Ask Jason + LAUNCH founder interviews + OK Boomer with Andrew Yeung | E1551

Episode Date: September 2, 2022

Friday Variety Show! First up, Jason answers a bunch of listener questions. (1:16) Then, Molly interview two amazing LAUNCH portfolio founders building marketplace businesses! (21:09) To wrap the show, Producer Rachel is back with another edition of OK Boomer (42:04) (0:00) Jason tees up today's segments! (1:16) Ask Jason: How to vet startups when you're an employee looking to join one (5:55) Ask Jason: Keep building a specifically requested feature for a major customer OR focus on the core offering? (10:32) iTrust Capital - Visit https://itrust.capital/twist to create your Crypto IRA today (11:38) Ask Jason: A pro athlete asks Jason for his advice on transitioning into VC (14:42) Ask Jason: Two hypothetical questions about Uber's business (19:29) Grammarly - Sign up for a free and get 20% Grammarly Premium at https://grammarly.com/TWIST (21:09) Molly sits down with Giphting CEO Seth Brown to talk about his on-demand gift-giving marketplace (29:16) Neo.Tax - Get $500 off R&D tax credit fees at https://neo.tax/twist  (30:32) Molly interviews EnrichedHQ CEO Carleen Haylett about her business: a two-sided marketplace of life skills programs for kids! (42:04) OK Boomer: Producer Rachel interviews Andrew Yeung on tactics for throwing an amazing networking event/dinner Check out Giphting: https://www.giphting.com Check out EnrichedHQ: https://www.enrichedhq.com FOLLOW Seth: https://twitter.com/GiphtingSeth FOLLOW Carleen: https://twitter.com/carleenhaylett FOLLOW Andrew: https://twitter.com/andruyeung FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood Subscribe to our YouTube to watch all full episodes: https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1

Okay, everybody, we have a jam-packed Friday show for you. First up, I'm going to kick it off with a couple of great-ass chasing questions. Then Molly is going to sit down with two, not one, two amazing launch portfolio founders, and she's going to find out why we invested in those companies. And then we're going to wrap with another edition of OK Boomer. It's going to be a great show. So stick with us. This Week in Startups is brought to you by I Trust Capital.

Did you know that you can invest in crypto through your retirement account and still get the same tax advantages as a traditional IRA, visititrust.capital slash twist to start investing today. Grammarly is an all-in-one writing tool that helps you churn out clear and concise communication fast. Go to Grammarly.com slash twist to sign up for a free account and get 20% off when you sign up for premium. That's GRA, MMA, RLY, dot com slash twist. And neotax. Don't leave money on the table.

Claim your research and development tax credits with neotax and get $500 off any service fees related to neotax products. Learn more at neo.tax slash twist. All right, we have a couple of S-Jasons that have been backed up here. I wanted to get them. We had a great question from Gabe. Long story short, says Gabe. Got my first taste of the startup world as an early employee at a small B2B. SaaS company, a business to business software company.

Here in my local town, I left and want to join another startup. Do you have any advice or questions to ask to make sure I don't join a company that won't be around in one to two years? Okay, great question. If you want a company that you think is going to be around in one to two years, you're going to look for a company that has raised, let's say, over $10 million, over $20 million, and that has over 50 or over 100 employees. Now, why did I pick those numbers?

Well, venture capitalists are not going to put $20 million, $50 million into a company that they don't think is going to be around in two years, and that should give them enough runway to be around. The later you join a startup, the later in the startup's life cycle, the less responsibility you'll probably get because they have so many people. They might have five people doing one job or two people doing one job as opposed to one person doing five jobs, right? That's the benefit of going to a startup

that's in an accelerator or just seat funded and has under 10 employees. And the other benefit of this late stage company is you probably have a greater chance of your options being worth something, but you're going to get much less of them. So when a startup's worth 10 million, and they might give you as an employee

a quarter point, 10 basis points, a 10th of 1%. Okay, 1% of a $10 million company is going to be $100,000 in shares. So if you got 50 basis points or 25 basis points, a quarter point or a half point, you'll get at 25 to 50K in shares. Okay, that's kind of interesting. But it's not a lot of money, right?

If your salary was 75K and you got 50,000 in stock options, it's nice. But what you're actually betting is that $10 million company will become worth $100 and then a billion, right? You want to see it go $100x. So what you want to see, ideally, is that $50K become worth $500 and then $5 million. That would be a great startup journey for you. Now, if you join the company when it's worth $100 million, are they going to give you 50 basis points,

$500,000 in equity? No, they're still going to give you $50,000 in equity, which means instead of you, right, getting a half a point, right, one-two-hundredth of the company, you're going to get one-two-thousandth of the company, the same amount to make it worth $50,000. They're still going to give you $50,000 in equity. So you're going to have a much lower percentage, and you're going to be betting that your 50,000

will 10x to 500,000. And yeah, maybe if they've gotten to a $100 million valuation, there is a chance they could become worth $5 billion or $10 billion. So you're lowering your risk. You're lowering your percentage ownership. The chances of the actual equity being worth something go up dramatically the later you join, but your percentage ownership goes down and your chances of having like a true home run go down.

There are some exceptions here, which we call the rocket ship exception. If you know something's a rocket ship, and it becomes pretty obvious. You kind of knew Uber, you kind of knew Airbnb, you knew Facebook and Google long before they were worth billions of dollars. It was pretty clear to anybody in the industry that these were rocket ships. You got a chance to get on a rocket ship. You take the chance. You get the seat if you're looking to be a startup employee.

And so that's really what you should be doing. If I was you, I would look at which companies have raised money from a quality VC. could be David Sacks at Kraft, could be Chimov, could be Bill Gurley, could be Rulhoff at Sequoia. One of those great legendary firms, I would try to find a legendary venture capital firm's investment portfolio and go to one of those companies, because then your signal is going to be really high that the equity could be worth something, right? Those companies tend to perform two or three times better than ones that are backed by no-name VCs. And that's not a dig to the no-name VCs, but the top VCs get better deal flow. therefore their companies on average are much better. And so that's my best advice to you, but you're doing it right by going to work in the

business to business sector and working at startups and really thinking about the risk level you want to take. Some people might want to take more risk and get more responsibility. I would rather you go to a company earlier when there's 10 employees so you can get more learnings and who cares if it goes out of business. Nobody's going to hold that against you. And you learn a lot when it goes out of business. So I would rather see you learn more.

but if you find a rocket ship, can't blame me for getting on a rocket ship. You're going to have a greater chance of getting rich. Okay, great question from Robert coming in. We have an enterprise customer in Pilot who really likes a feature on our platform. Equipment inspection, says Robert. It is used multiple times per day by multiple users six days per week. Okay, interesting. Should I try to sell this to other enterprise customers or continue building out with this one customer?

Currently, I can disagree with my co-founder on this. Okay. So let me explain what's going on here. When you're starting a company and you're trying to figure out product market fit, you will have sometimes a customer asks you to build what's called custom software, software just for them, a feature that they need. And sometimes these features are a complete and utter waste of time because they take you off of building a piece of software for everybody.

So you have a list of all the different features you can build. And then you also have to maintain and evolve those features. So technical debt does build up. In this case, it's equipment inspections. And so let's come up with an even better example. Let's say somebody is using Slack. And they say, you know what? For Slack, I would really like to have Slack do a chat room where everybody has to answer polls.

And we ask people a series of questions and we're a polling company and we poll people. We're a Pew Research and we want to have polling built in. And you're like, well, there's this other polling software over here. Why don't you use the polling stuff? We want it built into Slack. Okay. So now you're competing with not. not only chat and communication software, now you're competing with polling software and there's

like survey monkey out there and other polling software. Like, why do we have to build this is the question you're going to come to? And you're now splitting your resources between two different things. Only one customer wants this. That's a big problem. And so that's the second point that Robert makes it. Well, hey, listen, this is being used by multiple users six days a week. So maybe this polling software for pure research using Slack gets used all the time.

Okay, that's an interesting piece of data, but they ask you to build it. So obviously they're going to use it. Should I try to sell this to other enterprise companies? customers are continuing you building out with one customer. So this is really, you're answering your own question here. If you're going to be putting time into this, is it worth it to put it in to your product, make a Franken product where you're bolting stuff on for only one customer? Why would you do that? Well, you would do it if you thought the other, you know, if you had 100 people using this product, if you thought, I don't know, 25 of them or 50 of them would do it. And it's

really easy. You can make a little video and send it to your other users and say, we're trying to filing a feature, would you be interested in this? Yes, no, maybe. And just force them to answer the question, yes, no, maybe. Then you would get a pretty good idea. And this is like the product discovery process. There's a whole art to this, product discovery, talking to customers, teasing out of them what they want. There's listening labs, there's surveys, there's interviews, there's all different ways to do product discovery. And you can look that up online, the whole product discovery, listening lab concept to figure out what people want. And you can study people and say, how do you currently do this?

And that's how great products are made. Now, if you're in disagreement with your co-founder on it, one thing that you might find is that there's two businesses here. There might be two businesses. So if you're in your co-founder, find two businesses, what you could do is you could spin one off into a new company. And you could no longer be co-founders. I'm just saying if it really was a serious disagreement.

And that has happened historically, where one founder will stay with Justin TV and another group will go to Twitch. And they just, you know, one specializes in video games, one specializes in life casting, right? I think it was the situation there. And so you see that all the time when founders disagree. If you really feel strongly about it, well, you've got to pull the string and see where it leads you. And if it leads you to, hey, there's two companies inside of one, we're going to pursue those two different opportunities. Yeah, by all means, you know, spin out or maybe you pivot. And so this is one of the great things that comes from listening to your customers.

The thing that would become problematic is if this customer is paying you $50,000 for this equipment inspection software and you can't charge them anymore, they won't pay you 100. And you're spending $200,000, you know, investing and building this, then you're going to make the money back maybe if they get to their fifth year. So you have to do a little bit of ROI calculation. If the equipment inspections took you a week to build and it's going to take a week to maintain it and you put every week of developer time and product manager time at, let's say, 5,000 a week for two or three people to work on it. Okay, it's going to question $10,000 a year, one, $5,000 each year. They're paying $50,000 for it's profitable and they're a lighthouse customer so you can use

them to do other customers. Sometimes doing a little custom software is not the end of the world. But if you do that, make sure you do it with an API so that the next time you have to do another custom piece of software, you can build an app store and let somebody else build it with an API into your software. And then you can get on Zapier and have your API available for other people to do creative things with. Great question from Robert. A bunch of asset classes have been hit hard so far in 2022. But if you're a long term believer in crypto, you might be looking to invest. And if you're looking to invest in crypto, as a long-term play, check out ITrust Capital. I Trust lets you invest in crypto through your retirement account. It's basically a crypto IRA.

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legal investment or tax professional. Okay, we got a question from a professional authentic trying to transition into venture capital. In your opinion, what do you think is the best path for me to get my foot in the door in VC? Which furthering my education be the best way to do it. What about various venture capital strategy courses that are available on the web? There's no downside to taking some courses. I teach angel dot university. We give the money to charity.

We've given almost $200,000 to charity now. It's really a cool course. And that's a five-hour course. Venture Deals does an online course. People seem to love that one as well. and it's a great book as well. So, you know, there are courses out there that you can go take. There's nothing wrong with taking them.

If I saw them, I would be like, okay, that's a minor checkbox to me. What I think would be a more meaningful checkbox is investing in 10 companies, even if you found those companies on seed invest or Republic and you put but $500 into them and you have a portfolio worth $5,000 or you did the syndicate and angel list and other places for accredited investors and you got, you know, 10 investments of $2,000 each. And then you go to work for those founders. You help them find employees. You give them product feedback and you take them out to dinner or coffee and you'd be generally supportive.

If you came to me and said, hey, listen, I've done a portfolio of 10 companies. I now want to break into VC. Here's what I did as an angel investor. Boom. That's a quick path in. Because what you're trying to do is take yourself out of the bucket of talkers and put yourself in the bucket of people who are doing it and are unstoppable. You know this as an athlete. So if you say, hey, if you give me a contract, I'll become a great basketball player.

And they're like, well, there's a basketball court right over there. Why don't you show me what you can do? And why don't you get out there every day for five hours a day and, you know, perfect whatever skill you think you are going to specialize in the NBA at. Yeah, you know, maybe, you know, think of it like an open tryout. Any venture capital as you can get to, you can email 100 venture capitalists today. What are you going to email them? Trust me, I'm going to be good at this? No.

You want to email them and say, hey, Jason. Hey, Ruloff. I'm a professional athlete. I am looking to break into VC. I've made seven angel investments over the past two years. Here's what I've learned from them. Here's a document. And here's a testimony from each one of them.

I'm looking to break in as an associate at a venture firm. And here are my seven references, seven CEOs of companies. And here's what they said about me. And here's their emails if you wanted to check in on me. Like, that would be a bold move. And if I saw that and I'd be like, audacious, bold. This person is doing the job with or without me.

And then I would maybe write blog post. about what you're doing and be active on social. That's a great way to build a brand, as we've seen. Many VCs, you don't need to have a podcast to be a venture capital. I know that I may have started a bit of a trend here where every venture capitalist thinks they need to have a podcast and now they about startups and investing. And now they need to have a podcast with three of their friends and do a roundtable. You don't have to just copy what I've done.

Podcasts are not the only vehicle. I used to do a blog. That got me on the map too. Social media can get you on the map. Hosting small events. Just anything to show that you're in the bucket of people who are doers, not talkers. You need to put numbers on the board. You need to show people that you really want it through your actions, not through your talking. All right, great question. I wish you the best.

All right, got a couple questions. I got a couple questions on Twitter recently. The question from Marin, could an Uber-like business have grown in the current environment of higher interest rates, potential recession, and how would it have impacted how they strategically approached growth? Great question. In fact, Uber was started right after the financial crisis. And people looked at Uber as a way to save money. So yes, absolutely, they could have, they could have, and not only could they have, they did. It was a really bummer of a time from 2008 to 2012. And people were not throwing tons of money. And the tons of money came in that 2012 to 2022 period, maybe 2015 to 2020 is, to 2020 is when it was kind of peaking. So you absolutely could do it. And people don't remember

that even Green Desk, to the precursor to We Work, another company you would say, hey, how could this company ever work in a higher interest rate environment, etc. Or in a capital constrained environment, well, you bootstrapped. And Uber was a very bootstrapped company. What people don't realize is it was only Uber Black. And the Uber Black service was highly profitable. Taking 25% of a $50 or $100 ride from the airport is a pretty great way to print money, as opposed to doing Uber Pool for $4 or UberX for $12.

Those $8 Ubers were the ones where they were maybe losing $2 a ride. The black cars, they were making $10 per ride. And that is why they got so well funded. Just like WeWork and Green Desk, the precursor to it, did really well because they bought ugly office spaces. They made them hipster with the lowest cost stuff. They were super cheap. They had high margins.

And they took, you know, $12 square foot space or 25, let's say, $25 a square foot per year space. $2 a month if you live in a city where they do it monthly versus yearly in New York. They always did it yearly. Out in California, they do it monthly. Probably paying $30 a square foot, but they were charging the equivalent of $125 a square foot. And they had that huge margin. People only remember when they went into hypergrowth and they were losing money.

Now, when you look at those businesses, yes, they did lose money. But if I say the word to you, get a cab ride, you say Uber. And I say, get a desk. you say we work. I say ride. You say Uber. I say desk, you know, shared office. You say we work. The amount of money that was put into these brands has paid off massively and it will continue to pay off. I believe that we work will continue to be like the gold standard in office sharing and I bet you all the money put in will be taken out at some point. And Uber clearly is there already. They've already started to hit free cash flow. And so yum yum for J-Cal. Question from How would the company be different today if Travis had stayed on a CEO?

He's talking about Uber. Man, that is a great alternative fiction story. You know, I think there would have still been a lot of heat on the company, right? Because it had become a target and, you know, people were unhappy with certain aspects of how the company was run. But I think the company would be worth 25% more today of Travis was on because I think he would have continued to have Bob as a CEO and he was getting better and better every day, every week, every month, every year. And I think he probably would have been rewarded by the markets for being audacious. But some people might say that the public markets wouldn't have wanted the company to go public,

so they might have had to hold the IPO. And that could have been a really dangerous thing to do. So we'll never know. I think at some point it would be absolutely fantastic when Dara's done doing his great work and Dara's been doing a great job. If at some point Dara wanted to move on for Uber and Cloud Kitchens to merge and for the king to return, the return of the king, and I would be there for it. That would be an absolutely glorious moment if it became Uber Cloud Kitchens and Travis

was CEO again in a couple of years. That would be absolutely fantastic as an outcome. He's just a great world-class CEO leader, visionary, and he's unstoppable. And people don't know what's going on at Cloud Kitchens. I know a lot. I say nothing. I say nothing. Travis is keeping everything on the DL, and he's just got his head down working.

And, you know, when he's ready, he will come on this pod and he will do an interview. I talked to him about it. You will hear him first here on this weekend startups, for sure, when he's ready to talk about it. But he's my friend. I don't put any pressure on him to talk about it. When he's ready to talk about the incredible work they're doing in Cloud Kitchens, he'll be ready. But for now, he's in the lab. He's doing the work, grinding.

That's his superpower. That kid's a grinder. gets it done. All right, great questions, everybody. Being a concise communicator is so important, especially in a down market. You literally can't afford to have any breakdowns and communications, not with your team, not with your investors, not with your startup founders, not with your customers. But luckily, grammarly makes professional writing fast and simple. And I love this product so much. Everybody on both my teams, I pay for 50 plus licenses a year. That's why I was so delighted when I found out they wanted to support this week in startups.

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And when you're ready to upgrade to Gramerly Premium, which I know you will want to do, you're going to get 20% off just for being a Twist listener. That's 20% off at G-R-A-M-M-A-R-L-Y.com slash twist. Okay, next up, Molly's going to sit down with Seth Brown. He is the CEO and founder of a startup called Gifting. Seth went through our full launch cycle. He started with Founder University, our 12-week program, where you don't even need to have been incorporated. then he got into our accelerator, we put $100,000 into his business,

and you're going to hear all about his journey right now. Stick with us. So our launch accelerator just finished. It's 25th cohort. And as you probably know by now, I've been sitting down with some of the founders over the next few weeks to dig into their businesses. I've talked to Spring Eats, legal cues, swayed, and chatter.

This cohort just keeps on given. We're more than halfway done. And today I have Seth Brown, the founder and CEO of Gifting with a pH, Seth, welcome. And congrats, congrats on completing the accelerator. Thank you. Tell us what you're building.

Yeah, we're building an on-demand gift-giving marketplace. We want to change the way gift giving is done both on the buyer side and on the seller side as well. So how does that work? What we're doing is we're pulling inventory from our retail partners, both on a national level and a local level, pairing that with a curated list of items taking into consideration people's interests based off their geographical location, price point, what the occasion is,

and we're able to deliver those gifts in as little as two hours. Two hours. Tell me a little more about the specific problem that you're solving. Is it the speed? Is it the inability to pick out a gift? Like, what are we, how is this going to make everyone so much more considerate and loved. A combination of the two. I am guilty of forgetting my own anniversary, which is where the concept came from. So first and foremost, it is saving people like me that are either last-minute

shoppers, which majority of the population are, to be able to go ahead and provide a gift, also not knowing what to get. We've created a machine learning platform to take into consideration real real-time interests, constantly being updated, constantly being trained. And then, then there's also an even bigger piece of this, which is on the B-to-B side for retailers. One and four gifts are returned annually, and retailers are eating about 60% of those costs as it relates to liquidations, processing, discounting fees. And we've created a virtual gift exchange within the platform to essentially eliminate the return, ultimately saving on their major losses. So you could re-gift, you mean? You as the gift receiver have the ability to exchange the

gift out and say you want a different gift prior to it being delivered all within that two-hour window. Love that. And that's a good, that's actually, there's a good climate impact there because returns have a really big climate impact. A huge impact there. Six billion pounds of waste annually and 16 metric tons of CO2 released annually because of gift returns. Yeah, remarkable. Walk me through how this would work. Is it local retailers? Do you also have the benefit of bringing them online and allowing them to be part of this ecosystem? So we started with national retailers wanting to bring on to allow us to scale, but we view this as a huge benefit to local retailers.

It's their way of having instant real-time delivery. We want to give back to the community. We want to find those local favorites, whether it be your favorite music shop or bookstore, whatever the case may be. We want to be able to partner with local retail. to be able to allow them to see what it's like to have that speed and that on-demand environment. And then how do you handle the delivery? So we're currently using white label delivery providers.

We have one national deal in place currently, and we've also agreed to terms with delivery aggregator, which will allow us to open up with a bunch more providers starting in the near future. And how do you get paid? Two different ways on the B to C side, we get paid from personalizations that we create within our app. Each gift can be accompanied by a 30-second video message that arrives prior to the gift going to the gift recipient. We also allow for, we also receive as it relates to the delivery itself. And then on the B-to-B side, we are receiving commission based off of every order that's being purchased.

And we also have a really unique marketing and partnership opportunity where different retailers can control different categories or different items during a for a specific point of time and different period of time. So consumers can pay a little extra to personalize the gift giving and then presumably they pay some kind of a delivery fee. Exactly. Okay. And then retailers, of course, pay you a commission for the sales. But tell me a little bit more about this customization kind of option you're talking about on the retail side. On the retail side. So the retailers, they have the ability, we can work with a retailer to say, okay, you sell this product. We can ensure that you're getting the sale over the course of the next 10 days, two weeks, whatever the case may be. And it also benefits them because their competitors aren't

during that period of time. So we have the ability to choose where the item is coming from within a geographical location. Oh, I see. So you can, so if a consumer goes on and just says, I want this gift. You're saying you retailer can pay me a little extra to make sure that that gift comes from your store instead of the neighbor's store. Exactly. I see. Clever. All right. And then in our classic accelerator style, so let's talk about your traction, which is looking great.

7,200 downloads, 85 orders, a 300% increase in website traffic since launching just last month. Yes. We launched towards the end of last month. So we're about three, four weeks into it right now in our pilot market of, of, South Florida, and we're seeing great traction, great growth. We're seeing tons of engagement as it relates to people using all the other features within the app as well, such as our wish list, our calendar reminders so that others like me don't forget their anniversary or special occasion. And each day, we're getting more and more growth and traction, which is a really exciting time

for us. That's fantastic. And is it all organic? Like it's word of mouth growth for the most part? So prior to launching, we built a community of over 22,000 people. We really wanted to make sure that we had that solid foundation. And so we've been working on onboarding that community that signed up and joined our waitlist, as well as a few different marketing initiatives, primarily using search and some influencers and social media. Gotcha. And then what is your path to $10 million and $100 million? Yeah.

So in terms of $10 million, we're looking at. at approximately 30,000 deliveries per month, looking at about 350 deliveries annually, and Path to 100 million is roughly 350,000 deliveries per month, which we look to do as we go ahead and we scale the uniqueness about our platform and gift giving is that even though we're only in our pilot market right now, anybody can go ahead within the country, you can go ahead and can actually order a gift for somebody in our pilot market, which is a lot different than a lot of other on-demand platforms where we really have this two-to-one impression engagement that's taking place because there's always a gift giver and a

gift receiver. So we're actually able to use and leverage the gift giver as a way to bring on board a gift recipient. Network effects. You got to love it. Yep. Seth Brown is the founder and CEO of Gifting at GIPH-T-I-N-G.com. Seth, thanks so much and congrats again. Thank you very much. Right now, it's so important for founders to save where they can. And one source of capital that's rarely used are R&D tax credits. According to Neo-Tax, 97% of U.S. R&D tax credits go and claimed every year. So Neo-Tax is going to help you get up to $250,000 if your business qualifies, and there is literally no downside to using Neo Tax. The application takes less than 30 minutes, and you'll know in the first couple of seconds if you qualify, plus you only pay if

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belong in your business. Okay, what a great interview with Seth, but we're not done yet Molly sits down with Carline Haylett. She is the CEO and founder of Enriched HQ. They're a marketplace with a really interesting business model. It's an amazing conversation about her startup. So stick with us. All right. So the launch accelerator just completed its 25th cohort.

I have been talking to all of the founders over the past few weeks and the next few weeks to dig into their businesses. You've already heard me talk to almost all of them. Next up, Carline Haylitt, CEO and founder of Enriched HQ. Carleen, welcome and tell us what you're building. Yeah, hi, Molly, big fan, so thanks for having me. Enriched HQ is a central hub, a marketplace of skills building and life skills, enrichment activities for kids, grades, four, and up.

We work with large corporations to bring this to working families, parents, to support their kids. Give me some more details. How does it, how do you do this? Is it an app? How do they pay for it? What does it help them do? Are we talking laundry here? I hope we're talking laundry here. Laundry, right. My kid needs to get his acting gear. Yeah, exactly. I'm desperately trying to get my kid to put his dishes in the dishwasher. So, um, probably not that though. Yeah. This, this comes really from my own experience as a single mother. wanting and needing to engage my son in enrichment activities that just weren't being addressed in school. So life skills, building things.

And as a technologist really knew that this could be solved with technology. So after 10 years of dealing with this problem, I finally got to the point where I said enough. And so we built a marketplace. that aggregates together best in class content from leading organizations around programs that extend learnings beyond what kids are learning in school. So think maybe master class, but for juniors. And so corporate organizations contract with us to bring this to their working families. And parents have access to this and distance.

to this and discounts and free and exclusive content through the platform. But we handle all of the logistics of building a complete program for the parents. Because quite frankly, as a parent, I know, it's a nightmare to go out into the internet and to find multiple vendors and times and schedules and all of those things. So we bring it together in one place and couple of companies pay us to do that. Yeah, I mean, I cannot tell you how many threads I have been on with fellow parents of like, what are you doing for summer camp?

Does anybody have a good tutor? Does anyone know where we can take a skateboarding class? What are, I'm so interested in this idea that you could partner with businesses and have it be something that's offered through work. Tell me about that insight, because that feels like a big unlock for you as a business and then also your parent customers. Yeah. Well, like I said, this is something that I've been dealing with for 10 years. So I don't have a nuclear family here around me in Boston. So it's always been this crazy labyrinth of care that I've had to piece together. And it's a nightmare. And so what I've decided to do with the company is go out in. to the world and find the best in-class providers for things that families have told me that

they want their kids to learn, things like, you know, budgeting skills or investing or language or things that are really beneficial when they can be beneficial when they're delivered in a virtual capacity. And so we go out and we find these companies. We partner with them. We make them available on the marketplace. And then our platform handles all of the transactional elements of building a comprehensive program for the parents across, you know, different vendors, multiple kids,

multiple schedules, multiple price points. We just, you know, our goal is, Again, I live this nightmare every day. And so how do I make this easier for parents to better balance managing their professional career as well as their home life? Tell me about the revenue streams. Because it sounds like there are three major ones. Yeah, multiple. Tell me how you get paid.

Yeah. So first and foremost is our engagement with corporations. and they enter into an annual contract. And I have sold to Fortune 1,000 companies for 15 plus years. And the more simple it is, the easier it is to get a deal done. So it's an unlimited contract for a flat fee. And it renews annually. And so that's the corporate piece.

Our activity providers, we are an exclusive ecosystem. So only companies that provide content where we invite them to join our ecosystem, they pay us a monthly subscription fee to get access to promotions, to our captive audience through our clients. And then the third piece is we take take rate on every activity that's booked. So it's essentially a revenue share with the partners. Right. So you get paid on both sides of your marketplace and on the transactions. Nice. How, and it looks like it's working in marketplace bookings are growing 36% month over

month. You're available to over 200,000 employees. What's the feedback that you've gotten from the partners? So far, it's awesome. I mean, I think a sigh of relief. from the parents, right, is a big one. We work really heavily with diversity and inclusion executives. So we have direct access to a lot of groups within these organizations that support working families, particularly mothers, a lot of high-profile programs around elevating women in leadership. And then, of course, there's the retention.

aspect of it and employees who would have chosen to leave because they're sick and tired of paying ridiculous amount of money for extracurricular activities for what feels like the right to have a job are staying with their companies, which is eliminating attrition cost for the organization. So it's really almost like an extra benefit. If you're two of your big customers, is Adobe or American Express, you're saying, are parents also getting a break on price then? Are you saying, like, listen, we're going to have these summer programs that, you know, are available to you and at a discount? Yeah.

And a lot of them are offered for free to the employees. So, you know, every corporate account essentially buys differently and they want a different thing. So we start with the baseline. And then we say, okay, do you want a subsidize? the rest of the cost for the employee. Some of them have said yes, so all activities are free. Some of them have buckets of money that they're pulling from learning and development that was only available to employees to upscale.

They're now making those funds available for programs like ours to support the children of their employees. Some of them we do, because of we're an ecosystem of exclusive providers, we do free curated activities for a particular client. Like, I'll give you an example. We've done, hosted a global hackathon for one of our clients where each region had a team of kids and they all competed for the global champion hacker.

you know, thing, which was really cool for the kids. And so, yeah, and that was, we offered that for free. It lets you, it lets your employees and us, the parents, stay at work, knowing that our kids are not just like, at home, latchkey kids in some, you know, unbedded program. Yeah, gamer videos, which is what goes down in my house. Same. Our classic, of course, accelerated question is what is your path to 10 million, and then $100 million in revenue. Yeah, we've been really, really successful with some really great flagship customers out of the gate. And so we anticipate we're on track for just shy of 500 grand in revenue this year.

And by securing three to five additional corporate clients and the activity. rate conservatively, we've estimated out that by 20, the end of 2020, we'll be at 2 to 3 million, which will take if that with the current clients will get us to about 87 million by 2025. So if our rate of 36% month over month continues to increase, we're well, exceed that by 2025. Carline Haylett of Enriched H.Q. I am rooting for you.

Thank you so much for the time. Take care. Have a great weekend. Single moms, taking care of each other. Damn it. That's right. We got to stick together.

Okay, next up, producer Rachel is going to wrap the show with another awesome edition of OK Boomer. This week, she's talking to Andrew Young. By day, Andrew Young is a strategy and ops leader at Meta. You may have heard of that company, but by night, And on the weekends, he writes about leadership growth and mindfulness. He hosts events, parties, and dinners in New York, seems like a really cool cat.

Enjoy the interview. OK Boomer. I understood the assignment. Today, I'm speaking to Andrew Young on another great segment of OK Boomer. He's a strategy and ops lead at Facebook, but that's actually not what we're going to be talking about today. I've mentioned him before on the podcast. So if you listen to other OK Boomers, you might have heard me talk about Andrew. So when I first moved to the city, I went to a bunch of free tech events.

And that's really how I made all my first friends, other than the friends that I already knew here that went to college with me. But I would just show up to these tech events a lot of times alone. And they were really awesome and were a huge pivotal reason why I ended up loving New York City, even though I moved in January, which kind of is not a super fun time to move in the city. And the big question that I got back from people after mentioning these events that I've previously seen, spoken about are how am I even finding these tech events? And that is where Andrew comes in. And by the way, if you have any questions, if you have any questions, please feel free to send them along to producers at this weekendstartups.com with the subject line, OK Boomer. And now back to these tech events. So there are a few people operating in this space, but none of them are as organized,

is professional and consistent as Andrew. If you follow his newsletter, musings, and perspectives, or his Twitter account, you totally know what I mean. Thank you so much for coming on today, Andrew. And I know I just spoke for quite a while, but do you have a little elevator pitch? Like, how do you describe yourself? Yeah. I mean, I give, and thanks for such a nice intro, I guess I have two intros and one's like, you know,

when I do it for work, which, you know, we don't have to talk about today. It's not terribly exciting. but I'd say what I do on the side is just get, you know, what I, what I sort of call the best, which is like the most open-minded, the kindest sort of people in tech, business, media, creative. All these people together are at really cool venues around the city. And so normally it's been like, you know, like a rooftop. Like we did something at VR World.

We do like bars and lounges around the city. We do dinners, that kind of thing. And it's just getting people together to chat in a business or friendship, anything related to sort of, you know, why you. you would want to go in the first place and meet other people in New York City? I think my first, like, big question is, how did you even get into events? Because it doesn't seem like that's a very natural progression from working at Facebook. Yeah, for sure.

So I think, like, so I moved here August 2020. So again, like, not a great time to move to New York City. I think, like, everything was closed. And I'd moved here for a reason. I moved to New York for the same reason that everyone else does. It's to meet people. is to sort of accelerate my career, my life, and just take part in that intensity and the energy

that we all call New York City. And I moved here in 2020, and I realized, like, all the restaurants and bars and all that kind of stuff was closed. There weren't any events, you know, when I used to visit, there used to be, you know, a bunch of stuff around the city. And so what I did was, you know,

reach out to people on all these online sort of networks. So, you know, the first ones I used were, like, Reddit. Actually, I was a very sort of late joiner to Twitter, where I had an account, but I didn't really learn how to use it until like much later down the line. But like Reddit and like Fishbowl and like LinkedIn, and I would just sort of message people and be like, hey, moved here. We've like chatted online before. Do you want to like meet up, grab a drink, grab dinner? And I did that at scale.

I did a lot of those one-on-ones. Eventually started meeting a ton of like cool people. And I was like, you know, I got to connect these people. So I started doing smaller dinners, like six day people. And that's really the sweet spot for like good conversation and that kind of thing. And it continued to sort of scale. So after that, it was like bars or like sections of bars, like 40 to 60 people and then started doing like, you know, entire sort of bars and lounges. And now we're at sort of like, you know, rooftops with like over 600 people.

And so it really started small, a lot of one-on-ones. And as I start to meet really cool people, I start to connect them together through like dinners. And those started to scale through like word and mouth and through my newsletter. Awesome. So a huge thing that I've noticed that people have issues with when trying to host events is actually trying to find that event space. So you mentioned, like you started off small now. I've even attended some of your rooftop events, which are in no way small. How are you securing these events?

Like are you finding sponsors or restaurants now like asking you to come at this point and just bring in people? Yeah. Initially I would just sort of build a relationship with the, you know, with, some of the owners of the venues that I really liked. So the hotel, you know, the Williamsburg Hotel, I've done like four, four events there now, going to do another one in September. I love that venue. I love their pool, their rooftop, you know, their hotel. And so it started going there a lot and building a relationship with the people that work there. And once they started to find out about, you know, what I do, it was just like a natural next step to sort of work together and

put on events. But there are a bunch of bars around the city, bars and restaurants that sort of, they they rent their spaces out for free and some of them even have like no minimum. Wow. So those are great spots. They tend to be like on the smaller side like under 200. And then the larger ones,

you know, the reason I do my events on like a Monday to Wednesday is because like the Thursday, Friday, Saturday, it's just their minimums are too high. And you know, most of the time, if you've sort of proven

that you can bring people to their venue and make people spend, they don't even charge you a minimum at some point. So at this point I sort of have just like people at the different venues around the city that, you know, sort of have an open conversation and open thread with them and, you know, they're very open-minded. Gotcha. And why do you think it's important for people to attend events, even people maybe that are native to New York and have lived here for a while? Yeah. I think the incredible thing about New York is that, you know, when I moved here, I met so many

people who had very established friend groups and they've lived here their whole lives, you know, yet they're still going out there, putting themselves out there and like meeting. new people, which I think is really amazing. So I think, you know, to answer your question, go on events, you know, you hear all the time when people talk about sort of like networking, and I don't really like that word as much, but people are always like, I got to go in coffee chats. Like I got to go to at least one networking event a month. And I sort of hate that, that concept of like, I have to do this. And so one of the ideas behind, at least my events is like, I want to make it more fun, either through like the people or the venue or some kind of, some kind of

context within the event. But I think, you know, by my meeting people and like really exponentially branching out and building out your network, that's going to give you what's going to make you happier. You're going to have more friends. And it's also going to just help you accelerate your career. Yeah. I totally agree with you. I've kind of had a experience similar to the one that you're talking about where when I first moved to the city, I was really thankful to have some college friends that were here. But I went to a massive university. I went to Penn. state, so absolutely loved it. But it is kind of hard to branch out, honestly, from that small group that felt like my Penn State friends or my college friends. And by going to different events,

even if it was showing up to some alone, which felt a little scary at the time, but now, now that I've been to yours, I know that's pretty, pretty common. It has definitely made the city feel a lot more accessible, which is awesome. And I guess on the other end to that question, why do you think people should be hosting events? Because I don't want to say that you were like the catalyst for people hosting events, but I do think that there is a huge shift in people having dinners where people just had little set down situations to these full-blown, like walking around talking to other people and maybe free-flowing conversations that you really specialize in. Like, why should we or people be hosting those? Yeah, it makes me really happy when I see other people

hosting, especially like, you know, I think a few of the community builders in New York have like really creative and special events. Like Mike McCombie, he does really cool events, like New York Field Day, that kind of thing, like Rachel Cantor. So I think everyone sort of has, I mean, everyone's network is different. And I think everyone has the ability to sort of curate the people that they think would get along based on their goals, you know, their vibe, their energy, that sort of thing. And so I think it's important for everyone to sort of have a point of view on who they think should sort of get together. And as a result, you get sort of very, very diverse events, very creative events

that spans sort of all the industries in all types of roles and that kind of thing. Yeah. It's funny you mentioned Rachel Cantor. So she actually came on the podcast before episode 1436. Rachel is awesome. It's definitely another incredible community builder. Another person you introduced to me that I have to give a shout out to is I think David goes by the brunch guy on on Twitter, but another just absolutely phenomenal, really cool

community builder. And I feel like, so now you have this, it almost feels like the more I see content on your page, the more I actually am exposed to other community builders. So you've literally built a community of community builders. What advice do you have to people who want to break into the event space or maybe host an event of their own. Yeah, that's a really good question. So I think when you think about events, right, you need a couple of things.

So you need a venue. You need sort of what I call it, distribution or you need a community or people that would actually attend the event. Sometimes you need a partner, but I think if you do an event from Monday to Wednesday, you could probably get by without spending much. And then you need some sort of context or like an anchor in terms of like why people would go to the event. So I think I've seen some cases when people were like, oh, I really want to host an event.

I love the idea of bringing people together. But they're missing like one of these elements. And these are really like the four sort of building blocks you need to throw like a decent event. So for anyone who wants to host event, just keep those four things in mind. The first one you host, you're like going to be nervous. And I've talked to a few folks who first event, very nervous. And, you know, it's hard for them to have a good time because they're so tense and they're coordinating. and it's like in their moment sort of thing.

But after you do, I'd say like three to four, it's going to feel more natural. And you'll get to a point where you actually have a lot of fun of these events. And there's not much planning and coordination required. So my tips, just to sum up, keep those four things in mind. And it really just takes repetition for you to get comfortable enough to have fun and to make it sort of like a, you know, make it more automatic for you.

Gotcha. I do have a question. Was that a article? Or a written piece in your newsletter, the four pillars here? No, not yet. Maybe I should write something about that. I was about to say that honestly, that sounds like really good, tangible advice that people should have down in writing.

I think that's super, super great. And do you have any advice maybe? So say I want to do like an OK boomer event. I want to try to find everybody that I listen to. I think I've mentioned this before on the pod, but I think it's really difficult to kind of see like my podcast and community, like one time when Nate O'Brien. was on the podcast who is one of my favorite podcast guests to have on. I said, like, hey, if anybody's listening, like, shoot me a message on Twitter.

And I got so many people messaging me that it absolutely made my day. But besides that one time, it's kind of difficult to know who's listening. So if I wanted to do an OK boomer event, but I did not know, like, I don't know how many people have listened to this segment, what are the first steps that I would do? or somebody that's never planned an event before. Yeah. Yeah. I mean,

you can like sort of like, what's called? You could sort of like test, test like the demand you have. And so sometimes, or a lot of the times what I'll do is I'll like post a tweet. I'll be like, who's like interested?

Right. If you're interested, like comment. And I don't, I think a lot of people think I do that for like engagement sort of hacking. But the fact is like I have this tool which I can share, I can share with you after, which like automates like Twitter DMs to anyone who commented.

And so if anyone, if anyone like DMs me, that's actually more work for me to go in that DM in my inbox and reply and post a link. And so if it's like, I think the first time I did that, I had like maybe like 150 comments and I just automated all that stuff in like two days. A lot of easier. How did you do that? That's so set. It's a tool called, it's called twift.xy Z. It's a really cool tool. Okay.

That's so awesome. Yeah. Yeah. Super, super efficient. And I'll send it to you after. I know the guy that created it, and he's, you know, he's sort of, he built some really cool products. But I would say, you know, sort of test or demand a little bit, whether that it's through a newsletter, a survey, or like Twitter.

And then from there, you can sort of gauge what kind of venue size you need. And I would say, you know, like if I have like a thousand RSVPs, normally 40 to 50% will show up if it's a free event. Yeah. So use that as sort of your rule of thumb. Yeah. I think that's really awesome that you were able to. to use a plugin like that to help.

I think that's one of the most difficult things I've seen in the event space is the RSVP versus like the show up because especially in New York, and I'm sure this goes for other cities, but the actual venue itself, like the cap on the amount of people you can have. If you have like 60 people in event space, you meant to have 200, it is very evident.

And then vice versa, it is not comfortable. So maybe New York more than most cities due to the nature of they're not just being very much space. I feel like knowing the number of your audience is something that's super important, at least as somebody that attends events, it's something I definitely notice. Are there any other things that you find that are super important besides the amount of people just show up?

Like, the fact that there's food there, the fact that there's like, I don't know, a bar, like, is there any key aspect in an event that you think people should really be paying attention to? Yeah. So I used to think, you know, we need an open bar. And I was like, we have to do the open bar thing. But in fact is, like, on a Wednesday, nobody really wants open bar on a Wednesday. It's probably like 120 bucks per person per head.

And no one's going to drink that amount of money or eat that amount of food. So I don't really do the open bar thing. I did an event with Nick Gray a while back for like Sahil, Bloom and Sam Parr. And Nick is like the master of like events. And I think he's mostly done sort of like smaller curated events. And he does like icebreakers. And he wrote a book on how to like throw a party like a two hour cocktail party. He wrote a book on events.

What was it called? Let me pull it up right now. Is it literally? Yeah, I think it's two-hour cocktail party, something like that. I love that. Yeah, I saw that. Unfortunately, I was out of town for the event, but that Sampar show out seemed to be really cool,

some of that absolutely blasted all over social media. And I actually got to speak with Danny Miranda, who is another wonderful podcast host, speak with PAR, I believe, around the same time. So I got a lot of, a lot of his content in one swift weekend, which was really awesome. Yeah, it was really cool event. And what Nick did there was he introduced the idea of volunteers.

And he had about, so let's say we had about, I think like 500 people came out to that event. He had about 30 volunteers come out where yellow hats and their job was to go around and do a couple of things. One, if anyone came alone, just like talk to them, make them feel comfortable. and second of all, to sort of connect different groups and different pockets with each other, so people were sort of like mingling with each other, not just the people that came up with. And I did that at the rooftop event I threw last Wednesday.

We had about 70 volunteers come out, and I thought it was a success story because I got some DMs after and people were like, I loved this volunteer. They were awesome, introduced me to someone who was exactly who I wanted to meet. And so that, you know, the ice breakers is something like I never used to think about,

and I think most people don't. Definitely, definitely a good idea to try out. Very awesome. That's awesome. I feel like I keep saying awesome, but it's like there's no other word to put this. And unless you've been to like one of Andrew's events, like it's really difficult to put in awards.

And especially as somebody who's moved around a lot. So I'm an army brat for people who don't know. So I've moved like for high school, for example. I actually had four schools and four years. So being able to go to events like this, I feel like I wish had more of it. impact on me, even younger in my high school career. Do you have any tangible advice, I guess, for people maybe that want to start doing events even before they get in this corporate setting,

like when they're in college? Yeah, I think, you know, that's another good question. Like, the act of like not only the coordination of events, but like the facilitation of the conversation and like how you run the programming during the event, I think that's a muscle that most people can start working on. And it's like, if you're in like, college, you can like throw like smaller parties, like dinners, you know, happy hours. You can still do a lot of that stuff and find creative ways to connect people. You know, I think the sort of the baseline thing you do is you find a venue and you put people in it.

And if you want to take that one notch up, you know, you start to do icebreakers. And then even like one level higher than that, it's like, how do you pre-program things into the event so that people will like definitely sort of meet others and you facilitate sort of the idea of serendipitous connections and that kind of thing. definitely a lot of things you can do in college. Awesome. My last question, what has been your favorite event that you have put up so far? That's a really tough one.

I love the hotel. I really love the hotel. So any other rooftop events I've done there have been really cool. I'd say the last one with the volunteers, you know, that one I thought went really well and it didn't rain, so it was perfect. But I'd say while I do love the really massive events, I also do. this sort of under the radar happy hour every month. It's about 16 to 20 people.

Those are really fun because those are a lot more curated. The conversation is a lot more intentional. And I actually get to talk to everyone who goes. And I think everyone sort of gets to talk with everyone. So those are ones. I'm going to start sort of sharing on Twitter a little bit more. Those are probably my favorite ones. Awesome.

It's so funny. Actually, I've never seen you at one of your own events. I've never seen you. Yeah, I've never seen you except for the one where it's kind of of like a happy hour where we all went out for dim sum one time. I've actually never seen at one of your events. So next time I'll have to hunt you down. Yeah, I was thinking about that. I was like, you know what? I don't think I've talked with you at one of those. Well, thank you so much for taking the time to come on. If I ever do a OK Boomer meetup of sorts, I'm going to

have to contact you again and have you show up because you seem to be rallying the troops over here. Absolutely. But I'm happy to help. Thank you so much, Andrew. Yeah, thanks for having me. And where can people find you? My Twitter. My Twitter is Andrew Young, Andrew, A-N-D-R-U-Y-E-U-N-G. Stellar, awesome. Thanks. Okay, everybody, thanks for tuning in.

What a great week, Monday through Friday. So much news, so much content for you as a founder or a capital allocator. We're going to be back on Sunday with another edition of VC Sunday School and this week in climate startups. We'll see you, Sunday. Enjoy the long weekend, everybody.