Startup pitch competition: Jason invests $25K | E1714

5 Apr 2023 · 59 min

Ask about this episode

Ask anything about it. ChatGPT or Claude reads this page and answers with the times it was said.

Connect VO and ask about every podcast you hear, including the moments you saved. Add to ChatGPT · Add to Claude

In short

Podcast Episode Summary: This Week in Startups - Startup Pitch Competition: Jason invests $25K | E1714

Episode Overview In this episode of *This Week in Startups*, host Jason Calacanis conducts a pitch competition featuring three startups from the Founder University program. Each startup has the opportunity to secure a $25,000 investment from Jason. The episode includes startup pitches, feedback from Jason, and a conclusion where he announces his investment decision.

Key Moments

  • Introduction to Founder University (1:07)
  • Jason explains the purpose of Founder University, a 12-week program designed to help aspiring entrepreneurs develop their ideas into viable products.
  • Pitch 01: Sticker by Xinyue Ma (7:14)
  • Sticker is an app designed for social accountability with goal-oriented challenges among friends.
  • Jason's Feedback (13:00): Praises the idea but emphasizes the need for high design standards to attract users.
  • Pitch 02: Outmost by Joseph Homsy (15:07)
  • Outmost is an online marketplace for buying and selling high-quality used outdoor gear.
  • Jason's Feedback (17:11): Comments on potential for community engagement and sustainability but expresses concerns about margins and returns.
  • Pitch 03: PaySquad by Cam Richardson (24:40)
  • PaySquad offers a group payments option at checkout for split purchases, targeting Gen Z consumers.
  • Jason's Feedback (26:55): Encourages finding a specific beachhead market to establish a strong presence.
  • Ranking of Pitches (29:45)
  • The three entrepreneurs receive insights about their pitches and Jason discusses the importance of product velocity and business models.
  • Final Thoughts on the Pitches (39:41 - 46:04)
  • Jason reflects on each startup's strengths and weaknesses, emphasizing the importance of execution.
  • Investment Decision (46:04)
  • Jason decides to invest $25,000 in all three startups: Sticker, Outmost, and PaySquad, citing their potential and the teams behind them.

Key Concepts

  • Founder University: A program for entrepreneurs to develop their business ideas, focusing on building minimum viable products (MVPs) and understanding customer needs.
  • Importance of Product Velocity: Quick iteration and execution are vital for startups to succeed. Faster-moving teams can adapt and learn from the market more effectively than slower ones.
  • Business Models: Discussions emphasize the significance of proven business models, such as marketplaces and fintech, along with the need for a strong product design.

Key Takeaways

  • Design Matters: The aesthetic appeal of a product is crucial, especially in consumer-facing apps. A good design can significantly impact user acquisition and retention.
  • Community Engagement: Building a strong community around a product can lead to better user engagement and customer loyalty.
  • Identifying Beachhead Markets: Startups should focus on specific target markets where they can establish a strong foothold before expanding.

Conclusion In this engaging episode, Jason Calacanis provides valuable insights into the startup pitching process and reinforces the importance of design, community engagement, and rapid execution in building successful startups. The decision to invest in all three companies highlights the potential he sees in diverse business ideas and the founders behind them.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Hear the part that matters, and keep it.Open this episode in VO. Double tap your headphones to save a moment as you listen.
Get VO free

Transcript

Automatic transcript. May contain errors.

0:00Today on This Week in Startups, three more founders from Founder University pitch their ideas for the chance to secure a$25 ,000 investment from Jason. It's going to be a great show. Stick with us. This Week in Startups is brought to you by Vanta. Compliance and security shouldn't be a deal breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. Twist listeners can get$1 ,000 off for a limited time at vanta.com slash twist. LinkedIn Jobs. A business is only as strong as its people and every hire matters. Post your first job for free at linkedin.com slash twist.

0:44And Mayfair helps venture-backed companies protect and grow their cash automatically. Diversify where you hold your cash, increase your FDIC insurance coverage, and earn up to 4.35 % yield on deposits. Go to getmayfair.com slash twist to get started today. All right, everybody, welcome back to the program. Y 'all had such a great response to our Founder University showcase where I told y 'all I would invest$25 ,000 in one of the four companies and in the last one, three companies, that I thought we'd make this a regular thing. So if you haven't seen the pitch shows we did previously, we did episode 1703 and episode 1709.

1:33We had four people pitch me in the first one. And then we had three people pitch me in episode 1709. I won't spoil it for you. You can see which one I picked for the$25 ,000 investment. And why are we doing this? Well, I started my career writing 25K checks to founders who had ideas. So I thought we'd bring that back, but we put a little more around it. And what we put around it is something called Founder University. This is a 12-week program that we run three times a year. Maybe we'll try for four. We have 200, 300 people who join it each time. And we pick the companies that have performed the best in terms of building an MVP, showing us they can actually build product and they can meet with customers and understand customer need.

2:17once we see those two things if they've got two or three founders hopefully too and they can actually build product uh we're inclined to make the first investment in the company the friends and family round of 25k now of course we invest more as a firm but that's just the starting point with me again today is kelly schricker she is i'm pronouncing your last name correctly right kelly schricker yep i you know you've worked we've worked together for five six seven years I realized I never say your last name. Nobody ever, we all just say, hey, Kelly and whatever. So, and I have dyslexia. So it really is like, your name is kind of tough.

2:54So Kelly worked with me on inside.com, did operations. And then she wanted to be a venture capitalist. She's been working with me here at launch for just over a year. A little over a year. That's right. A little over a year. And Foundry University needed somebody to run it. So Presh and Kelly have taken over Foundry University. We just completed our fourth cohort. and we're working on applications for the FIP, correct? Correct. Yes, we are. Okay. Explain to people what we're looking for today because we started, we let anybody sign up basically, but now we're being a little bit more refined since we have so much demand for the program.

3:32What are we looking for and why? Yeah, absolutely. So the first thing we're looking for is multiple builder founders in our ideal scenario. And the reason for that is we have got a lot of ideas in the world. And with ChatGPT and all these other tools, it's not hard to have ideas these days. And so we really want to see multiple folks who are all working on one problem. Maybe they have an idea. Maybe they haven't solidified that yet. That's totally fine with us. But as long as they're folks who have a skill set to bring that into the world, that's what we're looking for. from there as well we are looking for folks that have titles like developer designer ux ui sales and then ops kind of at the end of that list again folks that can actually bring the product into the market and get those early attractions taken care of yeah people um who can build product and if you're three idea people yeah we might accept you but we probably wouldn't be able to invest because we need people who can build product and ideas are easy execution is hard and people are probably overthinking um how hard it is to build an mvp in today's world with the tools that are out there bubble zapier and countless other tools you can build a product even if you're not a developer and if you can't find a developer to be your co-founder or a ux person or a designer well you might have failed the first test of being an entrepreneur which is convincing other people to come on the journey with you so founder university not for everybody if you're an idea person who can't uh get the resources together to build stuff you're going to be at a disadvantage so we're going to prioritize people who can build if we find developers specifically teams of two or more developers we're inclined to give them twenty five thousand dollars even at the early weeks of the program or at the start of the program if they have a great idea and they're just starting to build their mvp why developers have a greater chance of getting a product to market than non-developers so we have a massive bias towards developer founders and multiple founders that doesn't mean we won't invest in a solo founder there are great solo founders in the world but multiple founders means uh you're going to get more done and they have a greater chance of being successful all right so we have three different companies today they're going to pitch for two minutes i'll ask them a couple questions we'll talk about the merits of each of these companies and then we'll decide which one gets the 25 000 today um that will invest in the company.

5:57These are all from the fourth cohort or some of these from the first three? Correct. All from our fourth cohort of founder university. Fantastic. Now we are maintaining relationships with the first four cohorts. So we are emailing in a group way, the first cohort, the second cohort, the third cohort, cohort, and now the fourth and saying, hey, keep us updated on your business. If you make progress, we'd love to invest that 25k, maybe have you come to our accelerator where we put in a hundred thousand or even a direct investment from our fund which tends to be 250k and then we have the syndicate where we can expand an investment so you can apply at founder.university go to founder.university read more about the program there's a 12-week program there's a two-day program and there is a podcast and some blog posts to help you the tactical stuff but we're talking here about the 12-week program which is really the heart of what we do at founder university okay let's meet our first contestant on uh who's gonna get 25k from jacal sticker is the first company up yep sticker so shin you can come out yeah all right glad to be here i'll share my screen hey shin is here congratulations on graduating the program you have two minutes three to go my brother and i both used to play instruments but it was so hard for us to stay motivated to practice because they were such individual tasks.

7:23So we decided we wanted to hold each other accountable. And we said, let's send pictures to each other and send texts to each other to prove that we're making progress. And it was actually really motivating for a while until we started to forget to text each other. And we realized that it's really easy to get distracted from your goals. So that's why we're building Sticker, which is an app to create challenges with your friends so that we can actually accomplish our goals. So first you would create a challenge for any goal area. Then you would input how you want to measure the goal and how long you want the challenge to last.

7:56Then you'll add your friends as competitors and the challenge begins. When you log your progress, you'll also take a photo as evidence and these photos can be seen in a separate activity screen here. And when the challenge is over, the person who reached the most towards the metric that you selected is the winner. With Sticker, you have a dedicated place for social accountability. And we've also found through research that competition is conducive for motivation. And Sticker helps you do that very easily. And with Sticker, you can create any goals you want to have. So for example, your goal is to apply to jobs, you select job applications as your metric, and then you add your friends as your competitors.

8:35The duration of the challenge would be, of course, the recruitment season. So there's no other app out there or other platforms that can be the kind of natural challenges that can come up in natural conversations. And this is because they're either not engaging to remind you to complete your goals, such as docs or notes, and they're not competitive and you so you lose that kind of motivation aspect, or they're just not specific for your goal. So we're looking at affiliate marketing where challenges can when brands can create challenge templates and also a premium plan currently we're at mvp with 55 users on our wait list and this is our team with two developers and a designer and me as a product manager so at sticker we want to help each other become our best selves thank you all right incredibly well done i love this idea i use um the fitbit challenge with steps i was in another challenge where some friends and i who were trying to lose weight were all taking screenshots of our fasts inside of a fasting app called zero and i think they eventually brought those into the app.

9:50But not every app does this. And I started doing a push up challenge for myself. And I just created a Google sheet, but I would love to be able to create a push up challenge for my brother, or basically my two brothers and see if we could each do 10 push ups a day than 20. So I love the idea. I think it's great that it's an open ended platform. I love your idea of maybe putting in affiliate ideas, where I don't know, somebody like Gatorade could say you know hey start a challenge with your friends and whoever wins will send you some of this incredible uh you know liquid iv or element one of these uh those are our sponsors for our show better than gatorade i think um certainly much more healthy so tons of great ideas oh you could even you know do athletic greens hey drink your athletic greens every day these have really great potential so i love the creativity i've never seen anything like this in the field where it's an open platform for doing this and so there's a revenue model with the affiliates just if you could get critical mass and you throw in the athletic greens one in between two or three other ones where you throw in eight sleep for hey who can record their best sleep and then with apis you could build the eight sleep api into it or you could pull health data so what a wonderful great idea you said you had a couple of co-founders here tell me what do you do and And tell me about your co-founders.

11:11Yes, for sure. So I'm a co-founder as the product manager. So essentially, from the ideation phase, I was in charge of user research mainly. So talking to tons and tons of people, understanding exactly what the mental model is from wanting to have a goal all the way to pulling your friends in or family in, and then all the way to how you track those goals. So understanding this mental model is mainly my job and then directing the designers and the developers to work together. the designers of course mainly for the ui ux as well as the pitch decks as you've seen today and the developers are shipping the product and hopefully launching tomorrow great and how many co-founders is it right now there's two four co-founders fantastic listen it's 2023 the macro picture is a little shaky it's uneasy out there and tech is getting hit super hard.

12:03As such, you cannot afford to lose sales for silly stuff like not having your SOC 2 right now. If you are unsure about your SOC 2, you need to check out Vanta. Vanta makes it incredibly easy to get and renew your SOC 2. On average, Vanta customers are SOC 2 compliant in just two to four weeks. Compare that to three to five months without Vanta, huh? And they partner with over two dozen audit firms who have been trained to file SOC 2 reports directly within Vanta. This is a total no-brainer. A bunch of my portfolio founders have used Vanta, and they've had amazing experiences. And if you don't have SOC 2 compliance, you can't close major customers.

12:42One major customer, that could be the difference between your startup thriving or going away. So get it done right now. Vanta's going to give you$1 ,000 off because you listened to this podcast. Think about it. $1 ,000 off vanta.com slash twist you got to write that down put it in your notes vanta.com slash twist for$1 ,000 off your sock tube well this is great why do you want to be an entrepreneur why not just go get the easy money why not go work at google or facebook i mean i know they're both firing people right now but theoretically why not just join a big company and get a huge check as a product manager of course so being an entrepreneur i think specifically for this company is really meaningful to me going back to the story that i told at the beginning of the pitch it's important just from a personal standpoint i want to bond with my brother better having this sort of app allows me to bond with my brother who's back home um many many miles away and so i think that this is a wonderful tool for people to connect um in a time where it might be harder to connect because of geographical um you know different places that you're living in so i think from a personal standpoint i just think that this is solving a problem i think this is helping people become more fulfilled in their social lives.

13:52Fantastic. This is incredibly well done. Did you have a good time in the founding university? Yes, of course. I learned a lot. Awesome. Did you sincerely learn stuff or was it just some people tell us like, oh, I knew a lot about entrepreneurship. I knew most of the stuff you were teaching. But it was the 12 weeks of like, having to commit and, you know, submit our progress every week and the accountability. So which which was more important for you, the accountability of the program, or the information program or equal? I think definitely the information helped. I think, you know, it set me in kind of like a product thinking perspective, but definitely emailing Kelly every week, understanding, you know, that we have to be shipping products, shipping kind of updates quickly.

14:34I think that really helped our team as a whole to continue working throughout the few months. Well, pace matters and speed is why little companies beat the big slow ones. So I think you'll learn some valuable lessons that are amazing. Let's meet our next contestant on who will win. Jake House 25 Dimes. Okay. He's our next contestant. Shin, you can turn your video off. We will have Joe from Outmost next. All right. Here we go. Big Joe, how you doing? Good. How are you doing? I'm excited to see your presentation. I've heard great things about you. Three, two, go. Hey, my name is Joe and I'm a co-founder of Outmost.

15:11Outmost is an online marketplace for securely buying and selling high quality used outdoor gear. It is a community of people who are passionate about human powered sports. Meet Emily. She's looking for a pair of used vans and few snowboarding boots. And like most adventure seekers, she's discerning about her purchases and cares about sustainability. Emily checks Facebook marketplace and Craigslist and the experience is horrible. Nothing of quality is available in her area. Scams are prevalent and it seems like no one knows what they're talking about. And then Emily discovered Outmost, and she found an incredible selection of high-quality outdoor gear sold by other adventure seekers.

15:46On Outmost, she found those vans she was looking for in her size and in like-new condition. Sellers post for free, and they're paid instantly once their gear sells. Users communicate directly with each other, and everyone is covered under the Outmost protection guarantee. There's a 10 % commission on every sale, and that's a key source of revenue for Outmost. The demand for resale services is evident in public markets, and consumers like Emily are increasingly turning to online platforms. Consumers are demanding sustainability, and influential outdoor brands have responded with buyback programs.

16:15Unlike them, Elmos offers a wide range of products from various brands. Elmos is currently available in over 10 cities across Canada and the United States, and the community is starting to sustain itself. Our go-to-market strategy has helped generate over 200 listings and 5 ,000 site visitors. our business has been validated and is showing early signs of product market fit. At our current velocity, we're projecting Elmos to earn a net revenue of$17 ,000 in 2023. By Q4 2025, we anticipate$60 million in gross merchandise value and$6.5 million in revenue. Based on feedback from our community, including you, Jason, we are pursuing these initiatives, which are going to help us reach our goals in 2023.

16:54We are still understanding the true bottom-up TAM, however, high-level statistics suggest there is potential for a unicorn company in this space, and it will be Outmost. The team behind Outmost is comprised of decades of experience in outdoor recreation, retail technology, and we have strong board of advisors committed to our success. Thank you. Great job. I had seen this idea from you a couple of weeks ago when I did a session with the founding university founders, and it looks like the product has gotten better. Maybe a little design refresh, or you've evolved it a bit? a little bit for sure i think also the um the last time i worked on this deck it was from uh the nicu on my phone so it wasn't as as polished but oh you had a baby i had a baby and so that's a graduation is every everybody good now or still in the nicu everybody's good yeah everyone's home mazel tov that's incredible um thank you so uh you have uh how many co-founders in this company two so we have uh there's myself two or you and your and your co-founder me and my co-founder got it yeah and you are one of you a developer or both of you uh both of us so the two of you um ones you're both developers did you work together previously no we actually met at yc's uh co-founder match oh fantastic great yeah yeah it's it worked out really well so he's he's taking over the technical lead it's been me up until now really this started off as a project and it's just really grown kind of out of control now to the point where i'm i have a business on my hands and it's demanding all of my attention but he's taking over the technical lead and he's been on board for the last couple of months and he's really actually has some pretty grand didn't get in but you got into founding university uh i actually didn't apply to yc because presh pulled me into this course so this is why well nobody listen our hope is you know with founder university is that a hundred percent of the graduates go on to make great products and apply to yc tech stars and our accelerator and uh we just want to see people be successful so i think actually now with uh what you've accomplished already you have a good chance of getting into a yc or tech stars or even our accelerator so tell us tell us a little bit about why you're so passionate about this space are you an outdoorsman oh yeah that's i think that's probably the uh a good place to start is this is you know i spent all of my time all my free time skiing and biking um i used to be a guide i've worked in uh outdoor retail like the canadian version of one of the challenges with gear so i'm an avid skier as you know today was my 32nd day of the season so i will hit hopefully knock on wood if i stay healthy my 40 day goal um but what are the what's the nature of skiing gear of other mountaineering gear climbing gear whatever it is that you're going to have on this site that makes it unique what unique insights do you have into this space that we wouldn't know what's the number one insight you have into the resale of this equipment and these people i think generally it comes down to knowledge and it comes down on comes down to who you're buying this from if you're going to go and buy used gear from somebody you could go to facebook marketplace you could go to craigslist and you might meet someone's aunt who's selling her, you know, her son's or her nephew's gear in their garage.

20:18But if you're actually buying gear from somebody who knows what they're talking about, they've taken care of the gear, they can tell you all about the gear. If you're making an expensive investment, or if you're buying something that's, you know, well over$300 or$400, you want to make sure that it's in good condition and that the person you're buying from knows a little bit, knows a thing or two about the product itself so i think in short answer the community is and then is tied to the quality of gear that we have do you build a community of these like-minded folks and deal with reputation and people returning stuff etc what's your plan there so i guess i'll start with the returns first i think risk mitigation is probably one of the largest um potential expenses worked into this business model for example if we have to deal with fraud if we have to deal with returns if there is a dispute um we're going to handle that on a case by case basis and so far that's how it's been handled um pretty rare that it happens also we're you know we're still we're still scaling um so yeah i think it's it's really just a matter of case-by-case basis yeah all right well done and uh the program for you what did you get out of the program if uh you had to mention of you know one or number one and number two things you got out of the program i think honestly it helped filled in it helped to fill in cracks in my knowledge and my understanding i came into this with having worked at a few startups i've worked in tech I've listened to podcasts like yours for years.

21:59I feel like I have a pretty good grasp of things. And I guess the, um, the quality and the, and the quantity of content in the course, there was a lot of it that, you know, was, wasn't news to me, but there was a lot of it that had me checking myself. Um, I think I was, yeah. Can you think of a moment where you checked yourself specifically, like some piece of information or some thought bomb, you know, exploded in your lap?

22:26um i can't i can't say i can think of one specific thing but i think that's a pretty reoccurring narrative that happened throughout the whole course like every single day opening up the curriculum you might see a full page on a certain subject and you feel like you're the you're the expert or you know it or at least you have a pretty good sense but yeah filling in those cracks really really helped so everything from this i mean this entire pitch deck um you know that was based on the outline that was provided here. How do you, you know, prioritize the kinds of kind of information you put in the deck, what you're focusing on, how do you prioritize and your MVP, these sort of things.

23:04So prior, you know, customer feedback, that's actually probably one of the biggest things I took away. Awesome. Yeah. Getting customer feedback, super critical. The March to 1 billion users continues for our friends at LinkedIn. 875 million people are using that platform. them. Wow. Let's face it. It's been tough here in tech. There's been a recent surge in layoffs. And that means there are insanely qualified people out there on LinkedIn looking for work. And they're looking to work hard and even join startups like yours. So the stakes are high right now. You need to get great people into your startup.

23:38And all of this talent is flooding the market. So what I want you to do is go post your first job for free. That's right. LinkedIn knows what they're doing. They're going to show you how great this product is. Go to linkedin.com slash twist to post your first job for free. That's it, nothing to lose and everything to gain. What if you get that bar raiser, the person who knows more than you about the vertical they're working in, whether it's sales, UX, marketing communications, growth hacking, HR, accounting, whatever it is, now is the time to get that person and LinkedIn is where they're waiting to meet you.

24:10When I say LinkedIn jobs, I want you to just think better can today, it's faster. Let's do it right now. A little neuro-linguistic programming here. linkedin jobs better candidates faster better candidates comma faster a little pausing better candidates faster linkedin jobs linkedin jobs better candidates faster do what i do go to linkedin jobs and find qualified candidates faster post your job for free linkedin.com twist that's linkedin.com slash t-w-i-s-t to post your job for free terms and conditions of course apply because they're giving you something for free let's meet our next contestant on who's going to get 25 dimes from jacob next up we have cam with pay squad and cam we can see you excellent hi jason hey cam how are you nice to see you guys all right three two go kira i'm cam founder of pay squad we've created a group payments option at checkout so you can easily split the cost of your cart with others meet kelly she's shopping online for her best friend's 21st birthday kelly doesn't want to just buy something lame but she also doesn't have the money to buy the kayak she knows her friend really wants.

25:12Luckily, she sees the pay with PaySquad option is available at the checkout. He only answers a couple questions, makes her own contribution, then sends a simple link to other people who may be interested in contributing as well. When they click the link, they can immediately see where the item is being bought from, how close they are to the target, and who has already contributed. No app download required. In no time, the total is reached, PaySquad pays the merchant, and the item is shipped. Her friend will be stoked. 29 % of Gen Z split the cost in scenarios like these every day, and this is being accelerated by inflation.

25:42However, visual wallets and bill splitting apps fail to solve pain points in a way that's globally available and actually includes the merchant. By actively including merchants, PaySquad increases their cart sizes and helps extend reach. Rather than only seeing one customer in the transaction, they have the chance to connect with many, reducing CAC. It's like a firm, but for groups. You could call it a buy now pay together. Our business model is similar to buy now pay laters, where we charge a commission fee to merchants for every successful sale. We achieve better net transaction margins because we don't require lending credit.

26:13Since starting FounderU, we've launched our MVP selling over$2 ,000 of product to over 100 users, earning a 3 % margin, signed up three merchants with several more in the pipeline, and connected to a global integrations partner to speed up our go-to-market by helping onboard merchants in the five main e-commerce platforms setting up massive network effects. Our path to 100 million starts with retail checkouts, where we aim to capture 2 % of transactions in 100 retail merchants in the next 12 months before expanding to group ticketing and travel verticals, then moving to a fully hosted marketplace with card issuing.

26:44Our founding team has built and scaled banking, billing, payments, and financial education apps. I'm Cam from PaySquad. Let's get checkouts out of single-player mode. okay well done so tell me about the transaction you said you had a hundred folks do two thousand dollars i think uh worth the transactions what were the different scenarios and has that taught you something about maybe a beachhead market for you to go after first it was indeed and the majority of them were people that we didn't know at all um and that was kind of the beauty of it how did you acquire them uh the we had a couple news articles about us being involved in in founder you actually that went out um here in new zealand and uh and so people oh so press to pilot customers press the pilot i like it yeah yeah and so we had um groups that were splitting the cost for their kids coaches for end of year um gifts we had uh groups of co-workers who split the cost for end of year presents and we even had a a big 30th birthday thing where people split the cost for a big gift okay fantastic and so you're you're a new zealand based entrepreneur yeah yes what's the startup scene like there is is there a dynamic startup scene or do people look at entrepreneurs there as like weird mutants a bit of both we have our home runs like zero and push pay and bend and a few of these massive ones but it's it's scrappy you know there's a saying here called number eight wire where we can build something with very little resource and make it and scale it to the world so we're kind of a kind of view ourselves as underdogs with a bit of a chip on our shoulder what does this expression mean you said number eight wire yeah it's a type of wire that's used for like fencing and just tying things together and this is sort of the mentality that we have number eight okay so you'd be like saying duct tape and chewing gum here in the united states like we slap this thing together yes i like it okay very good um and for you what's your background what makes you super qualified to pursue this if it's um it's in growth marketing uh and in product management as well my team and i have built you did growth marketing before yes yeah what was the most successful thing you ever did as a growth marketer financial education app uh scaled it from 15 000 users well over 19 sorry 1500 users to well over 19 000 um inside eight months uh did that as a consultant or as a friend startup or you worked there uh first employee uh first employee yeah and um and that was that for two things the financial education aspect really gave me a passion for the financial space and helping people make better decisions so one of the things for pace squad is leveraging young people's connectedness rather than their than their impulsiveness all right well done all right kelly this is a difficult one i spoke to presh um and i'll just have you give your ranking of who if i could only uh give 25k to one uh who you would give it to two and three okay here we go uh pay squad was precious number three who's your number three kelly my number three is sticker okay your number three sticker pay squad is precious okay and uh you're number two kelly pay squad okay and precious sticker which means you both picked outmost as your number one why do you think a marketplace uh for sports gear is the best idea and what or why did you pick that company yeah absolutely i think specifically in looking at outmost and thinking about what's going to have the best return for us you know this is a space that is incredibly proven right consumer marketplaces focusing on secondhand items have just a ton of traction and doing a little bit of research i found that um poshmark for example has over 70 million users and a gmv of 4 billion which is just crazy uh and i think really that's unbelievable yeah really nuts and i think what is driving this you think when you look at that space uh i'm checking your analytic ability here as an investor now you're one of my mentor i'm one of your you're one of my mentees i want to say that you're one of my padawan here i'm teaching you trying to teach you how to be a jedi uh investor what is it about that space when you think of the mental model um or the factors the why nows why is poshmark and why are these marketplaces you know working now what is it about yeah i think there's two reasons that that i've been looking at one is the sustainability aspect has just become so relevant in pop culture.

31:34So I think that is playing a little bit to what's going on. But I think the more structured and the more intense why now specifically is around, you know, the fact that there's a lot of uncertainty in the market. And, you know, folks aren't sure if the next few years are going to look like the last few years in terms of how much money is in their bank. And so I think people have had this appetite for nicer quality products, you know having hobbies that maybe they couldn't afford previously and now with all of this uncertainty the layoffs unsure on on home prices and where that's going to go you know folks are becoming a little bit more uh tight on where they're spending and so i think there's a really incredible why now here i really like your analysis uh this is why you work for me you've really thought this through you did research and you came with a prepared mind today and that's one of the things i learned uh from michael moritz and doug leone and the sequoia squad was hey have a prepared mind the prepared mind would tell you yes people austerity measures are in people's minds and there's a couple of generations that really care about not wasting uh clothes or products and to them the idea of um being able to use a snowboard or a gopro that's previously been used um to them they think they're helping the planet by not buying it new and unboxing it again whereas maybe my generation gen xers we kind of really wanted to have disposable income and be able to afford stuff and we wanted to own a bmw or mercedes or whatever it was uh or you know and the whole yuppie movement was about being a young urban professional and having that disposable income now maybe people look at it a little differently and i think those are two really great observations uh when we look at these companies and the nature of the companies and the teams.

33:21Now you made your decision, I asked you always to make your decision, what's in the best interest of our LPs. So we're clear, we're a finance company. We are not a feel good startup, we're not a content company, we're a finance company. Our job is to get a maximum return for our limited partners. And I have to repeat that often, we're not picking companies to make ourselves feel good or give ourselves a participation trophy, or because of diversity, or any other reasons. We want to see diversity and all this kind of stuff. But what we need to do to be in business is get returns for LPs. No returns for LPs.

33:57There's no business here. So we have a very specific mission, return the maximum amount. What about each of these teams as we go through it has impressed you? Because you are running the program and you've met with them. So maybe you could just say a little bit about each team. Yeah, absolutely. What's impressed you about each of these teams and how do they fit into our mental model and framework of teams we like to back? Yeah, absolutely. So Sticker specifically has multiple co-founders and multiple builders on their team. They've had really great product velocity throughout the program and they are also within our core four as all of these.

34:33For anybody listening, our core four are the business models that we like to invest in here at launch. And so they fit nicely into that thesis that we look for. Moving over to Outmost, next up, we, you know, kind of similar. They have the builder on the team. They've had really great product velocity and they've got some early users on the platform and have been listening to those customers. And so during the program, that really jumped out at me as I got to know them. And then last up, PaySquad. Again, very similar in that core four model. I know he, the founder, Cam, is not a builder himself, but he does have that growth background.

35:08And I think you'll be the one that, you know, once it's built and is a usable tool, and it seems like it is, that he'll be able to scale it pretty quickly through the early days. When you're a founder, priority number one is hitting your payroll. This means you need fast access to cash, no matter what goes down. So startups need to hold their money in more than just one FDIC and short account. We all know that, right? Been pretty choppy out there of late. So let me tell you about Mayfair. Mayfair is a cash vault powered by Stripe, And it's built for startups looking to diversify and grow their funds automatically.

35:43It takes 10 minutes to set up. It works alongside your existing bank accounts and, most importantly, FDIC insured. Here's how it works. You sign up for a new Mayfair account. You keep operating cash at your existing bank and deposit the rest at Mayfair for safekeeping. Then move your money back whenever you need it or let Mayfair manage your balances automatically. Mayfair can help you earn yield with no investment risk or locked ups. Earn 4.35 % APY on daily balances paid for by the bank. Your cash stays in cash and is never invested into money market funds, bonds, or other instruments. Withdraw your funds at any time, just like a checking account, Mayfair is designed to keep your money safe.

36:22They partner with Stripe to move your money securely, and your funds are held in the custody of Evolve Bank & Trust, which powers companies like Mercury & Wise. Your funds receive automatic pass-through FDIC insurance. So here's your call to action. twist listeners that sign up today earn 4.35 % yield on their daily balances that's more than 10 times the national average savings account go to get mayfair.com slash twist to start managing your cash like a fortune 500 company today that's get mayfair.com slash t-w-i-s-t okay this is once again well done kelly uh you continue to impress me as an investor um even in the early even though you're very early in your career only really starting your second year thinking about this We like product velocity.

37:05Product velocity, and it assumes some amount of quality, not spastic, like just throwing stuff against the wall that's ugly. But even throwing stuff against the wall that's ugly is better than not having product velocity. So product velocity is super important because the teams that move faster get to try things, they get to learn more. Then having multiple co-founders means you have redundancy inside the company and the founders don't pay themselves often in these early stages so the company doesn't go away when you have a solo idea founder and they have nobody around them who can build what happens they raise a little bit of money they give it to a dev shop and then it's over and then they need to constantly go back to the well to try to get some more money it's possible you you could be an idea person like i would say adam newman from we work is and now flow and you're just super charismatic you can get people to give you tons of money and hire hire that expertise but not everybody can do that so So in an early stage, it's important to have builders.

38:01And we like to back builders. We think they have a much higher degree of success. And then, you know, business model matters. So you have a marketplace here. You have sticker, which would be either consumers would pay or it would be affiliate slash advertising, marketing based. Got a social network aspect. Consumers might actually pay for that product. I think I would. And then you have pay swap, which is finance, right? So the major business models that work and scale and scale violently are subscription, people paying for software, either consumer subscription or enterprise. They have fintech and they have marketplaces.

38:39Those core four always seem to perform. Now, we don't limit ourselves to those. There could be other business models like data and affiliate and advertising. advertising but the big four we mentioned there tend to do really well um in terms of getting the flywheel going so now comes the hard part it's time for me to assess what i think of each of these i will be candid with each of the founders who can now turn on their cameras candid with each of them if they give me permission to be candid so as part of the program i always tell people i can sugarcoat it i have now learned how to sugarcoat it and throttle myself but i always want to be that partner you have in your company uh where i am brutally honest with each of you give me a thumbs up if you're cool with that i just want to make sure nobody's gonna get their feelings hurt here okay good that of course is a test if you can't take brutal feedback you're gonna fail as an entrepreneur so uh that was just the first test you all passed congratulations Congratulations.

Read the full transcript

39:41You know, for sticker, I think the product could look a lot better. I think design matters with consumers. And people judge books by their cover. I think you have a wonderful idea. I think you've got a sick team. And I think you've got the right passion for this. And your success will be determined in large part because it's a consumer product by how beautiful the design is. you know it's it's not bad now certainly not bad but it needs to be so good that apple app store will feature it how would you know uh if your product is good enough to be featured by apple's app store take a second to think about that how would you know if your product is good enough it's a bit of a trick obvious question but you know i'm a i do these kind of like dad obvious questions but how would you know what would be the quality of your product or the necessary design quality to make the apple design snobs feature it and they are design snobs they will not feature stuff that's jank what would it need to how would you need to how would you assess what they're looking for i think there's two aspects to it there's the sheer aesthetics of it so how well the colors how well um you know the size of the buttons and whatnot how well they look um and on the second aspect how well they work so does it feel good when you're using it and i think more often than not it strives for simplicity got it so how would you know what apple wants how could you figure it out i sorry yeah go ahead by analyzing the apps that are on the app store right now the ones that are featured you just reverse engineer it just go read the last 20 that have been featured and hear what app why apple loves them and try to take that list and sit with your team buy everybody a bunch of pizza burritos whatever everybody's into print those out sit in a room you all read it maybe you have chat gpt do a little bit of work on the side and you try to figure out what are the commonalities and then you reverse engineer it into your product and i think you know some of them the hooks the emotion i'll tell you another one don't tell anybody else um things that uh are unique to apple's apis also they kind of like that so apple watch uh being featured in the product so the apple watch gives you an alert uh or you know iMessage having some unique iMessage hook that only works with Apple's iMessage all of those things could be instructive so great job by the way and now when I look at Outmost I think again design could be a little bit better but it's a good start I do worry about margins and how to build that community and returns and all that stuff so I think studying how to get the flywheel going and doing real world events that make it a movement so my wish for you is can you make this into a movement because you heard kelly's analysis that she thought that this had to do with austerity measures was a good why now i like that but that also people really care about waste and i think figuring out how to make that a movement through live events where people come and swap stuff live and you host it live and you sign up at your website to come do it could be incredibly powerful and this is real world to digital signups and it can be incredibly powerful if you could figure out a way to do this there was real world virality to uber and lyft and sidecar before that what is real world virality that's when a person experiences your product in the real world and they tell the person next to him hey look at that and the example would be i order an uber i say get in i'll take you to the next party i'll take you to the next bar and they're like oh you have a driver and it's like yeah i have my own personal drivers called uber and they take out the app and they literally you download it in the uber and everybody's had that experience so real world virality could get you a customer acquisition cost of a dollar or five dollars whereas trying to do it online with facebook ads could wind up costing you 30 40 50 dollars um and that could be amazing just having an end of season or beginning of season swap meet uh you know at in tahoe and giving out flyers and then letting people sign up and giving people codes or whatever could be incredible so i just want you to think a little bit about how you make it into a movement in the real world nature of it and for pay squad you know i i like the fact that you're from new zealand i like the fact that you got a little chip on your shoulder like the fact that you're getting some press um but what i really want to see is i want you to own a beachhead market i don't feel like you figured that out yet and that's just going to take time but there is a beachhead market here of people sharing expenses And I don't know if it's bridal showers or a bachelorette party.

44:53You know, it could be something there. Or it could be there's just some place where people always split the cost. I don't know if it's whitewater rafting trips, whatever, travel comes to mind. But you're going to find one where you get market pull because it's such an arduous, painful process. Maybe it's golfing. I don't know. You know, people have to split the cost on golfing. So I really want you to find that beachhead market. and then i want you to pound that beachhead market into submission because when you find a beachhead market like that what people tend to do is they kind of drift around and they do 10 different markets and they do they spread the peanut butter really thin across like two pieces of toast and what you really want is a big spoonful of peanut butter you really want to have the thick deep you know real resonance so you can solve the problem for one group of people now there would be some criticism they're like uh you know oh you you've only works with one group of people don't worry about that people said that about airbnb and uber as well or coinbase or robinhood it's only for this type of person and then slowly other those zealots would explain it to other people and so you need to have those people who are just absolutely religious about your product once again i found myself loving all three companies but we can't sit here every week and give all three people 25k.

46:13Can we, Kelly? Of course we can. You're Jason. You make the decisions. Correct answer. I could do that. And today I will do that. All three of you get 25k. I love all of your companies. I love all of your progress. I love all of your team composure. I think you're all going to be super successful. So all I ask is that you put twice as much effort in in the next 12 weeks than you did in the last. Just keep up that high energy, that sense of urgency, because that is what entrepreneurship is about. I don't care if you succeed or fail. I just want you to put all your effort into it. And now is the time.

46:46Now is the time. There are so many people who want to invest in startups and they want to invest right at this moment in time, or I should say maybe in six months, when you figure out the product a little bit and you get that 50K a month in revenue, 25K a month in revenue. It's my honor to be able to be the first money into these three companies if I am in fact that. But if I'm not, I'm just happy to be early on the cap table. It just warms my heart that you're doing this and working so hard and have that product velocity. I just want to say thank you to Kelly and her team doing a great job finding these companies.

47:17Congratulations. Look under your desks. There's a brick, a couple of bricks of a hundred dollar bills. That'd be funny if we did it that way. If we put a package and you all open the package and we'd see if it was empty, you know, it just had a phone book in it or it had 25 large in cash. But okay. Any questions for me? Does anybody know what a phone book is these days? Exactly. anybody have any questions for me about entrepreneurship uh as we wrap up here i i got i have a specific question actually and well first of all thank you jason you are the first investor and uh after listening to your podcast for so many years it feels like you're a friend and getting to know you over over the course so um but yeah entrepreneur is a friend of mine i can tell you that the entrepreneurs are solving all the problems in the world as opposed to the people complaining but you had a question go ahead so i guess uh my question for So one idea I have is around actually sponsoring swap meets.

48:11So rather than that gets pretty cost intensive to set them up and there's already swap meets going on all over the world. So I guess my question is, if you see one in Lake Tahoe or if you hear of it, I'll do some research. We should make that the first one. And it's a great idea to do that. That would give you a jumpstart or you could make a playbook how to host a swap meet in person and online and you create the playbook for it and then you deputize people. We did a little experiment like this with This Week in Startups and fan meetups, and then all-in meetups happened. And it's kind of like a non-commercial validated thing where you find somebody who's running one already, you give them some support, and you say, Hey, we'd like you to do this maybe three times a year.

48:53If we paid you$1 ,000 to do them for each one, would that be helpful to you? And they'd be like, What? You'd pay me to do this? I'm doing this because I just wanted to help the community. so there might be something there where you can build a hybrid that's similar to tedx so anyway um one of the great things about having a good idea like the one you have is you'll have plenty of ideas and then you just have to prioritize and you know try the ones that you think have the best chart chance of success and then cancel the ones that don't found university in fact is one of those things that we did as a firm it was an experiment we did it for two days then we did it for 12 weeks we found the 12 week one led to much better outcomes so here we go and not that the two day didn't have great outcomes.

49:32It did, but this 12 week is having extraordinary outcomes. Anybody else have a question for me at the end here as we wrap up? Yes, I do. Thank you so much. This is crazy. Really appreciated your feedback on the design. I was just wondering in terms of like the team side, do you think that introducing more designers, more perspectives would help to hone the design? Or do you think that having one designer, perhaps like one perspective would help to create the cohesion on the design on the app? So great designers don't often want to work for one company because it's kind of boring for them. Let's be honest, right?

50:09They're not going to sink their teeth into it for five years. Now, sometimes a company will become transcendent and Uber or Airbnb again come to mind. And there's just, it's just so much fun to be the design head of that, that people will stick around for a couple of years and do it. So, and there are so many designers out there on a global basis that are so affordable for startups. So if you go to Dribbble or Behance or countless other places and you just say, hey, I'm looking for a designer to make five screens and you spec it out really well. And you say, give me two ideas that you think are reminiscent of these 20 and it could be the or 10 of the ones from your the Apple, you know, backing into the thing.

50:50Yeah. You say, hey, here are the 20 we've identified that are interesting to us. Pick, you know, be inspired by any number of these and then say, and give us one wild card. And you can get somebody to do that for just three screens, which is three design ideas for three screens. And you say, I'll give you a hundred bucks a screen. Now there are some designers who are going to be throwing up their hands like, oh my God, you're low balling us. Hey, startups, we'll give offers, low ball offers to designers and say, hey, I have 500 bucks. I have a thousand bucks. Would you do this for us? And you know what?

51:19you could just take it and throw it away or you could learn from it and then move on to the next and then you have to ask yourself if i hired a 75 000 a year 100 000 a year designer which would be better to hire a couple of freelancers for a thousand dollars two or three times a year and try to do that and then you find one you love yeah then you could contract them for a five thousand dollar you know job for six weeks to do this and then they might just charge you 50 or 75 bucks an hour i think there's an unlimited supply today of 50 to 100 7 50 dollars to 75 an hour designers out there and again i know some people are going to be like really offended and think i'm low-balling them and there's design firms that will spec this out for forty thousand dollars for you but that's not where you're at right now now if you raise three million dollars in a seed round or ten million dollars by all means hire three people for fifty thousand dollars and get the results of it and then pick the one you want and you're 150k in it's no big deal so i would just i think your instinct is right that you may not unless you have somebody internally who's extraordinary at design you might be better off getting some outside ideas or maybe go through the top 20 ideas out there and say you know what i really love this notion design aesthetic maybe we should go with something similar to that or you know it seems like tiktok and snap have something here that we can learn from or the zero app or fit bit you know you can look at how they do challenges and you don't need to reinvent the wheel in design you it's completely allowed to be inspired by somebody else's design aesthetic um and then go from there in fact i'm obsessed with the notion design aesthetic and me too every time i type in notion design or notion illustrations if you just type in notion illustrations there are literally like 30 or 40 people out there who are making that notion design style of illustration so you could have your team's avatars designed to look like notion made them for you it's really weird um so yeah i think your instincts are right um and there's little to lose and just make sure your team buys in that you know hey there's a reason to do this we we we are going to get we are a consumer product we will be judged just like we judge and i think looking at com.com which was one of the great design successes robin hood and uber at uber looked really bad at the beginning i mean travis was infuriated at the design i i've seen travis mad about things i've never seen him as mad as design i would ask him like hey what's the story with the taxi cab going you know it's going down the street but it's going down the street sideways like it's spinning out he's like god i told my designer seven he was really upset that he hadn't made like three different designs and now when your uber is driving it'll turn around and look like it's going in the proper direction anyway if you're not embarrassed by your first couple of versions you're not pushing yourself hard enough robin hood incredible design calm incredible design uber eventually incredible design the guys from airbnb man they went to risdy they were designers like they understand design medium my friend ev williams he was a design snob twitter design snob man twitter would i one time i went to see ev williams at medium and he had like nine people in the design department for a blogging platform i'm like what are they doing all day i asked him he's like well it's kind of like apple you know they they build a bunch of stuff and we throw away 90 and i was like wow you want to know why medium succeeded and why like president obama used to use medium it looked the best aesthetically looked better than a lot of things look at squarespace why did they win aesthetically they look better than everybody else they look better than their contemporaries all right final question if anybody has sure um jason thanks so much um outstanding uh pros and cons of having a physical footprint in the u.s in an early stage i mean if you want to win san francisco the bay is not the city but the bay area is having a bit of a renaissance and if you you know bring your team members and you camp out there and you start meeting with people i think magic can happen it could happen to a lesser extent in you know new york miami la and austin but if you're serious about it and you want to meet a lot of investors in a short period of time i don't think there's anything wrong with doing three to six months stint if you can swing it uh you know in silicon valley um and i think for all of you you know getting after you work on your product in a couple of months applying to the top accelerators if you get into one great you know that's another stamp in your uh passport remember it's a milestone based at its best silicon valley is a milestone based funding system as best i can tell and my 25k it's a great signal right you got some press after being in founder university because it's so unique to be a founder in new zealand right maybe you don't get that same thing uh from the press here in the u.s because there's a lot of startups here um but over time you kind of get these stamps in your passport yc tech stars certain investors and then all of a sudden you're anointed and then people take you seriously um now the ultimate thing is the growth of your startup and how passionate your customers are so never forget that it really is about how much value those customers are getting and how much value you can provide them and basically having customers who won't shut up about how great your product is the great vcs are going to seat through social proof but social proof can get you in the door so i wouldn't discount it it's important i always tell people like and people are like oh i'll have people offer free shares in their company to me we'll give you five percent of the company for free we just want to say you're an investor put your picture of the deck i'm like no thank you i want to buy the shares but um you know it can help uh you know to be a yc company a tech stars company a launch company to have an angel investment from somebody notable but it only helps you get in the room then it's a hundred percent you and by a hundred percent you i mean your product and your customers the product and the customers some people might say a total addressable market but generally if you don't have the product and the customers in sync what difference does the total addressable market makes so anyway uh this is the start now y 'all will be every time we invest in a company we move them over to our slack so now you'll have access to my team and myself in the slack and we can chop this stuff up uh we make little bird of a feather groups so we have some marketplace folks i think kelly would be nice to have all the marketplace folks in a bird of a feather maybe we could start the marketplace bird of a feather um put everybody there and then maybe the consumer app bird of a feather group we're starting these bird of a feather groups because i have so many investments now we want the investments to talk to each other so we started with direct to consumer where we have like 10 of these ddc companies it's challenging to be a ddc company right now because vcs have you know they're not as uh enamored by the space as they were so anyway we could put all these together and uh you know you can meet some other founders who are at similar places in time because you are all like mutants you're unique in the world um but you got to kind of stay hidden right like it's like this is like the x-men your mutants and you we can take you to professor x's uh academy and you can meet the other mutants looking forward to working with you all and uh yeah checks in the mail more wires in the mail good luck to y 'all all right uh we'll see you all next time on this week's starvis bye bye

From the publisher

Jason hosts another pitch competition featuring three startups from our Founder University program! Apply for Founder University: https://course.founder.university

(0:00) Nick kicks off the show

(1:07) Introducing Founder University

(7:14) Pitch 01: Xinyue Ma of Sticker

(11:56) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist

(13:00) Jason’s feedback for Sticker

(15:07) Pitch 02: Joseph Homsy of Outmost

(17:11) Jason’s feedback for Outmost

(23:14) LinkedIn Jobs - Post your first job for free at https://linkedin.com/twist 

(24:40) Pitch 03: Cam Richardson of PaySquad

(26:55) Jason’s feedback for PaySquad

(29:45) Ranking the pitches

(35:20) Mayfair - Get 4% APY on your idle cash automatically at https://getmayfair.com/twist

(36:50) The importance of product velocity

(39:41) Final thoughts on Sticker

(42:23) Final thoughts on Outmost

(44:26) Final thoughts on PaySquad

(46:04) Jason invests $25k in…

(47:39) Q&A with Jason 

FOLLOW Kelly: https://twitter.com/KSchricks

FOLLOW Jason: https://linktr.ee/calacanis


Subscribe to our YouTube to watch all full episodes:

https://www.youtube.com/channel/UCkkhmBWfS7pILYIk0izkc3A?sub_confirmation=1

FOUNDERS! Subscribe to the Founder University podcast:

https://podcasts.apple.com/au/podcast/founder-university/id1648407190

More from This Week in Startups

All 653 episodes
Startup pitch competition: Jason invests $25KThis Week in Startups · 59 min
Listen in VO