How Darrell Lerner scaled a startup to 120 million users
He grew a garage startup to $100 million in revenue.
I just sat down with Darrell Lerner.
He founded Snap Interactive and sold AllPaws to PetSmart.
In this episode you’ll learn
• Why he tested 30 different dog photos to validate a multi-million dollar exit.
• The “Mom Test” strategy for honest feedback (because your friends will lie to you).
• Why asking investors to sign an NDA immediately signals you are a rookie.
We dive into the details later in the conversation.
If you like the episode, please subscribe.
Timestamps
00:00 The journey to 120 million users
02:43 The art and science of pivoting
08:15 How to test everything (even 30 different dogs)
10:56 The “Mom Test” for valid feedback
21:51 Inventing the swipe before Tinder
38:55 Why execution eats ideas for breakfast
49:53 Unconventional advice for founders
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Here’s the full transcript:
Metwally — That One Time Podcast (00:00.142)
How did you and your brother grow a Garad startup into 120 million users and $100 million in revenue? A little brains and a lot of luck. Every founder, every successful founder has a bit of an ego, but you have to be willing to put your ego aside in the name of success. And if success follows path B, you have to be willing to scrap path A. It’s about winning. It’s not about being right. If you were to distill the strategies around viral customer acquisition, what would it look like? Test, learn, iterate, and then double down on what’s working. If you were to bootstrap
a startup now and aim to get to one hundred million dollars in revenue. What would you be focusing on?
Metwally — That One Time Podcast (00:43.214)
Welcome to that one time without a met while the podcast bridging the gap between health, hustle and happiness. We are at podcast for a while in Chelsea, New York City. And I’m with Darrell Lerner, a multi exit startup founder who grew his dating app to over a hundred million dollars in revenue and 120 million users over five years. And then went on to sell his pet adoption startup to PetSmart for high seven figures. He now advises for startups and founders and is the co-founder of New York City.
based elite influencer community and venture studio, Syndicate 11. What’s up, Dara? What’s up? I want you to take us back to the early days of your dating app startup, which was Snap Interactive. How did you and your brother grow a Garad startup into 120 million users and $100 million in revenue? A little brains and a lot of luck. So originally we set out to build a dating site. We launched a site called IamFreetonight.com, which was
essentially date by your schedule, who, what, when, why, and grew that over about a year and change. And we learned that growing a dating app is really freaking hard. a lot of the keys to startup success is kind of being willing to pivot and being willing to seize opportunities. And come 2007, Facebook opens up their app platform.
which at the time seemed revolutionary. The idea that you could tap into the data of a large social networking site and that didn’t really exist. And so we decided to see what that was about and built an app whose primary purpose was to drive traffic to imfreetonight.com. That was called Meet New People. And we saw incredible results and sensed that there was a potentially life-changing opportunity there. So pivoted on a dime, stop building imfreetonight.com.
In fact, we never touched it again to this day. Code is gathering dust somewhere. I went to work on a dating app exclusively for the Facebook platform that was called Are You Interested? Launched it, I think, August 14th, 2007, and started getting tens of thousands, hundreds of thousands of users by the day, by the week. And for the better part of the next three years, it was a top 10 app on the Facebook platform, ultimately website and
Metwally — That One Time Podcast (03:04.354)
iPhone app out of it too. It was really a case of if you understood how to go viral, especially in the early days of Facebook, which was the wild, west, you could do really well really quickly. And don’t get me wrong, we didn’t do anything shady, but just simple stuff like, Adam, you want to appear higher in search results, invite 20 friends. And in the early days of the platform, the ones who figured that out did really well. And then where I think, I’ll say a little bit of the brains came in, we were able to build a real business on top of that.
Yeah, that’s it. So how did you know when pivoting would be a good decision versus when it’s just ADHD? I think pivoting is part art and part science. I don’t know that there is an exact formula for it. I think a lot of times startup founders are so wedded to their idea, that and or its ego, that they’re not willing to pivot and not willing to give it up. And that’s a mistake.
So for us, sensed the dating site was growing, but not at the rate we hoped. And we saw that there was this what we believe to be life-changing opportunity on Facebook. We saw the ability to get thousands of users by the day, which for a dating site was unheard of. And we didn’t let ego get in the way. And we went after this opportunity. So I think you have to kind of ask yourself, have I gone as far as I can?
Do feel like I’m banging my head against the wall? there other opportunities elsewhere? What’s the opportunity cost? And like I said, it’s part art, part science, and just making sure ego’s not getting in the way. And if you go back to my startup framework of test often, test everything, it kind of lends itself to that. If you’re running enough tests, you’ll find opportunity. And then go where the wind’s at your back and run towards those opportunities and be willing to pivot.
So what percentage of say, let’s just say you make a hundred grand a year, a million dollars a year in a business, what percentage of your profit should you be reinvesting into testing? It’s an interesting question because I come largely from the tech world where profit is kind of an unheard of term, especially in the early days.
Metwally — That One Time Podcast (05:22.222)
Cash flow, baby. Free cash flow. You raise money from angels, from VCs, especially early days of a tech company or this day and age company. No comment. They want you investing all of that money back into the business. That’s why you see these companies raise every 18 months, every 24 months, because the goal is high growth. And they’re not focused on profits until later.
which is great when money is cheap and free, but when the market dries up, a lot of tech companies are screwed. So it’s a tough balance. certainly, an early stage tech company, I think you want to reinvest the majority into growth. OK, so how do you eat? Ramen, as they say. Yeah. Ramen. No, it’s interesting, because I’m a believer that founders should be paid a living wage.
And because you want a founder to be in the right mental space to pursue their business. And that thinking has changed over the years in startup world and Silicon Valley, et cetera, where in the beginning was like founders should take no money. They should work their ass off. They should focus on nothing but the business. Now, I think thinking has come around to founders should at least be paid a living wage, probably not the highest paid person in the company or second highest, but founders should be paid enough where
money doesn’t stop them from going all in on the business and it’s not a major stressor in their life. Yeah. I mean, there’s been a lot of prominent entrepreneurs that have famously never taken a wage. you know, like Larry Page and Sergey Brin have dropped their salaries to a dollar, but that doesn’t really count when the business is already crushing. Elon Musk hasn’t taken a salary for a very long time.
He’s doing OK, though. I think he’ll be all right. Well, I mean, that’s the question I wonder is, does not taking a salary actually really drive the person to extremes? I think those are extreme examples. most successful founders, even not necessarily the most successful, but to launch a startup, for the most part,
Metwally — That One Time Podcast (07:39.918)
You have to be glutton for punishment, right? Because there are easier ways to make money. There are ways to make money with far less stress. And most startups fail. So usually people go into startups. And granted, the landscape is a little different. It’s a lot more sexy now than it used to be back in the day. But they’re doing it because they have a passion. They have a vision that they’re driven by. So I think for a lot of people, money is not the primary goal.
you don’t go into startups to make money. It’s an outcome of success. So if you’re an Elon or someone like that and you can afford not to take a salary, I think it’s gonna impact your motivation. But I think for especially younger founders, paying enough, it’s really just about removing stress. Like being a founder is stressful enough and is enough to think about. So if they can take enough to not have money be a stressor in their life, like I think that’s the main point.
Fair enough. So if you were to bootstrap a startup now and aim to get to $100 million in revenue in 2026, that was your goal for, five, 10 years down the line, what would you be focusing on? Clearly AI. I don’t think there’s any question that the majority of the multi-hundred million billion dollar companies are going to be AI in some capacity. I mean, there’s other stuff that I’m not an expert in, clearly a lot of health, longevity, things like that.
But for me as a tech guy, mean certainly AI, and I’m going to go back to, I’m going to be a broken record on this. For me, it’s all about testing. Just test, learn, iterate, double down on what’s working. And if you’re smart and make some bets in the right direction, think you’ll land on something that will get you, I don’t know if it’ll be 100 million or a billion, but some level of success. How do you test good ideas?
you know, can be really anything from A-B testing, an onboarding flow, a funnel, a landing page, to features, concepts. You know, when I say test everything, I mean everything. mean, you know, when I think back to All Paws, which was my pet adoption site, right, the hero image, the primary image on the homepage was a cute dog. I probably tested 30 dogs.
Metwally — That One Time Podcast (10:04.206)
different images, know, cute puppy, yellow lab, golden retriever, puppy with child, puppy with old woman. I never made it in, which is probably why the company succeeded. But, you know, I tested a cat, I tested a sad dog, a dog in a cage, all those things. And one thing I learned is you rarely know what’s going to work. So, you know, don’t have preconceived notions. Kind of go in, just outline
all the different aspects of the company or the business that you can test. can be emails, how often you send emails, what the email subjects are, there’s just so many variations of things. So if you give yourself enough runway and you have enough traffic coming through that you can get meaningful data by running all of these tests, to me, testing should be over the life cycle of a business, even a mature business.
And you see a lot of companies that are still known. Netflix, for instance, is known for Amazon also constantly running tests. And these are multi-billion, trillion dollar companies. And years, years into their maturation process, they’re still testing all the time. How long do you generally test for before knowing it’s a flop? It’s a bit of a loaded question because it really depends on
you know, how much traffic you have coming in. So in order to achieve a statistically significant result. Is there a minimum that you would, depending on traffic, like is there a number that you’ve worked off in the past? Are you like, okay, I know this isn’t working now. I mean, I’m, I’m impatient. So there are certainly times where I’ll cut a test before I know we’ve hit statistical significance because I can kind of feel in my gut that I realize I’m contradicting when I say you never know. But look, if you’re AB testing,
a red button and a blue button. And the red button is converting at 36%, and the blue button is converting at 3%. Unless you’re talking about a sample size of two or three, you probably have enough to declare a winner there, even prematurely. Yeah. How do you A-B test a website like that? So concept of A-B testing really means taking two different variations of the same element and sending traffic to one and then sending traffic to the other.
Metwally — That One Time Podcast (12:27.848)
and seeing how they do in comparison to each other. And A-B testing can apply to anything from text, you know, the headline on an app or a webpage, to the color of a button, to the copy of a button. Like when you enter a website or an app, the button could be start now, it could be get started, it could be start your journey, it could be find your perfect pet.
There are infinite amount of variations that you can test. And then it’s with features. It’s really anything can be tested. And if you’re someone like me, you can get to the point where you find yourself testing things that probably don’t need to be tested just because you love it. just look at your product, look at an app, look at a website, and look at everything and say, is there something different here that could be done in comparison? Again, whether it’s a color, a copy.
a button placement, a feature, a time of day the email is sent, almost anything. And when in doubt, ask AI for a bunch of things you could A-P test. I mean, what was it? Thomas Edison had 10,000 failed attempts before he hit the light bulb. Yep. Yeah. This is your light bulb. So.
Who was Darrell Lerner before Snap Interactive? Were you always entrepreneurial or how did you take the leap? Who was I before Snap? Yes, I was always entrepreneurial. I literally had the proverbial lemonade stand when I was a kid. When I was a young kid, I had other businesses. When I was a young kid, pretended to be a travel agent. When I was a kid, I did a little
bookmaking in high school. What do mean you pretended to be a travel agent when you were a kid? I would order brochures and have my parents friends, like I would book a flight for them. Or I did a little ticket brokering, which consisted of someone said they want to go to a concert, I would call a ticket broker, buy the ticket for them, sell it them for 10 bucks more. So I did things like that. Yeah, I think it was always in my blood. Come from a bit of an entrepreneurial family.
Metwally — That One Time Podcast (14:48.078)
certainly learned a ton over the years and became much more of, you know, tech. I went to law school, I had a finance degree, so I didn’t come from the traditional tech background. So it definitely took being in the space for a few years for me to become more relaxed and kind of get on board with the ping pong table in the office and that kind of vibe. But I think, you know, I was always an entrepreneur and especially as I look back at some of the things I did when I was younger.
You could see signs of that. So what was your craziest side hustle that you ever did? So I went to sleepaway camp when I was younger and we had these things called candy days twice a week and you had to turn in tickets for, well, this is a two parter because I guess this is multiple income streams. You had to turn in a ticket to get your candy each week and
So I remember during the school year, we had a carnival day and I noticed the tickets they were giving out were similar to the tickets we used to camp. So I found a way to pocket a ton of those and save them for the summer to bring them up for me to get extra candy. I also noticed I had my parents bring me up for visiting day. If you remember from the old days, those cup of soups, those ring noodles, which people love for some reason. So I had my parents bring me up a ton of those.
And I traded them for other people’s candy days. So by the time I was done, I was basically the candy king. had an unlimited amount of candy, which when you were 11 or 12 years old, made you pretty popular on campus. Nice, nice, nice. And then what did you do with all the candy? Got some You bought elections. A lot of sugar, a lot of cavities. But a lot of fun. A lot of fun, too. Yeah.
So when building a startup, from your experience, how important is it to make it easy as possible for the user versus actually making it difficult and getting better users? super important to make it easy for a user, especially in the beginning. When you think about signing up for a product, every element that you add to the onboarding flow creates friction and gives users a chance to disappear, get frustrated.
Metwally — That One Time Podcast (17:12.11)
My view on onboarding in general is you want to make it as quick and seamless as possible to get users to your aha moment and the moment that makes them fall in love with your product. So the more friction you add, the more people you’re going to lose. So is there any value in having high friction in a business? I’m sure there’s some interesting edge case here, but not that I can think of, at least in a traditional sense.
It seemed like virality was the most important piece to growing this business that turned into a hundred million dollar business. If you were to distill the strategies and frameworks around viral customer acquisition, what would it look like? So I always get this question essentially how to go viral. And my answer is really unsexy. And I feel like in a way it disappoints people because everyone’s looking for a quick fix. Right. And for me,
it still boils down to this playbook, this framework of test, learn, iterate, and then double down on what’s working. And I don’t know that you can engineer virality. You look at people who are content creators, they probably had a ton of videos they thought were gonna do super well and didn’t. They probably had videos that they’re shocked that blew up. And it’s easy to look back and figure out why, but it’s hard to do it going forward. So again, for me,
the more things you test, really the more swings at bat that you give yourself, as long as you’re open to seeing the signals, right? The better chance you have of success. That makes sense. So building the business off the back of the Facebook platform, what lessons did you take from that decision and how would you approach growth potentially differently if you were faced with similar decisions today? I think the biggest lesson we learned from building on top of Facebook
was just being open to pivoting, being open to scrapping an idea that you had thought about forever and worked for years, maybe not multiple years, but for a year and change on, put money. Again, you have to, like every founder, every successful founder has a bit of an ego, but you have to be willing to put your ego aside in the name of success. And if success follows path B, you have to be willing to scrap path A.
Metwally — That One Time Podcast (19:39.584)
At least to me, it’s about winning. It’s not about being right. winning means building a successful business in whatever way makes the most sense. I mean, obviously still in line with your personal values and ethos and all that. for us, we didn’t set out to build a business on top of Facebook. I don’t even remember if Facebook existed when we got started. It was just about identifying an opportunity.
and then sensing that there was something incredible there and be willing to scrap a year of hard work to go after this better opportunity. And that’s a lesson I’ve carried with me to this day. Taking that opportunity.
How do you avoid the sunk cost fallacy? It’s tough. And that’s what trips up a lot of people. And I’ll go back to what I said before, which is you have to be willing to put ego aside. Like I think about in our case, we literally took a year’s worth of work, a fully functioning website that had 200,000, 300,000 profiles on it, which for a data site is not nothing. But it’s also not enough, especially when there’s no,
no geographic density or anything like that. It’s not enough to be successful. You have to be willing to put your ego aside and do what it takes to achieve the ultimate outcome. Like ask yourself, what am I trying to accomplish? You’re trying to build a successful business, not prove that your original idea was right. Yeah, yeah, fair. So I heard that you guys created the swiping function before Tinder. What’s going on there?
That is true. Good job. And that is a little known fact. But when we launched the Are You Interested iPhone app, way back in the day, we had swiping. And Tinder didn’t exist back then. So do you think they copied your swiping functionality pound for pound? You’d have to ask them. Have you ever spoken to them? I haven’t. My brother has, who kind of remained in the industry after I left. I know he’s had conversations with them.
Metwally — That One Time Podcast (21:51.308)
I can’t speak to where that, you know, the genesis of where Tinder came from, but I do know that we had swiping before them and before anyone else. Did you know that it would be a useful product feature? I’d love to say yes. You know, I think we thought it was cool and I thought it was an interesting and unique idea, but this really is, I’m dating myself here, pun intended, you know, the early days of the app store, the early days of iPhone apps, and I think everyone was just trying to figure it out at the time.
And stuff that is so common now, like swiping, was just, you know, it was a test. It was a bet on a product feature at the time. Yeah. So digging into the idea of validate before you build, could you please explain this and the consequences behind it? Sure. You know, it’s never been faster, cheaper, easier to validate a startup idea. Back in the old days, you know, people would create a business plan and then raise money and then go to work and then
pray and hope that it worked. And you don’t have to do that anymore, which is one of the beautiful things. And it’s what made entrepreneurship and solopreneurship kind of available to the masses. So the idea of validating an idea is basically proving that there’s demand before you get started. And that can be done so many different ways. You can launch a website, a landing page, and run ads to it to see what kind of click-through rate you get, see how many people give you their email address.
You can launch an offer before you’re ready, let’s say, for a course or something and see how many people buy it before you actually build it. It’s about validating that demand. And another aspect of that is people don’t get user feedback. A lot of people. don’t want to paint everyone with a broad brush.
the right way and people don’t get enough user feedback and they often don’t know the right questions to ask. Like when someone thinks about validating an idea, they probably think to themselves, okay, I’m gonna share with my friends this idea I’ve been thinking of and ask them what they think. And friends are generally wired to, depending on your friends, but good friends are generally wired to tell you you wanna hear instead of give you critical feedback. And the correct way to go about that is not to say, hey, I have this idea for this thing.
Metwally — That One Time Podcast (24:09.998)
Do you think it’s a good idea? Is it going to say yes? Instead, and there’s a book on this I love called The Mom Test, which talks about how to properly get user feedback or customer feedback. And it’s about asking questions about people’s behavior and their patterns, their day-to-day life, and seeing what surfaces. And you’re really not pitching your idea, your app, your product at all. You’re just asking them about their lives and their behavior.
and you’ll learn if your idea has merit if you ask the right questions. Do you know the difference between when user feedback is useful and when people don’t actually know what they want? That’s a great question. Like the old Henry Ford quote, if I asked my users or my customers what they wanted, I would have built a faster horse. Yeah. Yeah. This is another one where I’ll say it’s part art and part science because
users want things that might not have any sincere impact on the product, or let me rephrase that, might not stop them from using the product, right? Like users might say, I want dark mode, I want dark mode. Like we had a social app and that was one of the biggest requests, but lack of dark mode didn’t stop them from using the product. At the same time, if you search through user feedback, you’ll find nuggets. And I’ll go back to something I said earlier.
To me, what you’re looking for is people using your product in ways you didn’t intend for them to use it or using it in a way where you wouldn’t expect them to because the product isn’t sophisticated enough yet. Like if they’re using features that require a large number of people or require network effects before you have that critical massive users, like start diving into why. If you launch a product and your friends start testing the product,
and you get past the first couple of weeks and your friends have fulfilled their obligations to play with your product, see who’s still playing with it and see what they’re doing on it now that they’re not obligated to. Like that’s the high signal, you know, and that’s what you should dive into. Yeah, makes sense. So I want to dive in a little bit more into pivot versus persevere because it’s a fine line to figure out. Yeah, it really is. It’s tough to give up on something that you’ve worked hard on.
Metwally — That One Time Podcast (26:33.644)
I think the best way, and again, I’ll say it’s as much art and science, there’s no right answers, no playbook. For me, I think it sort of sorts itself out if you’re following this culture of testing, of always running tests. Because if you’re always running tests, you’ll be gathering data, and hopefully you have a tight feedback cycle, and you have enough users to get that tight feedback cycle, and it’ll start to become.
are more apparent to you what’s working and what’s not. But you also have to make some bets. sometimes you might be convinced that it’s the fourth or fifth try on something that’s going to work. Yeah, I wish I could tell you that there was a neat format for it. But this is one of those things that determines the success or failure of a lot of companies. And there’s some element of chance.
I mean, there’s a fine line between being the type of person who has such a
big bet on themselves and pushing through the really difficult times and also being the same person who can go, actually, we’re going to change this whole thing because something externally is showing me that maybe I’ve made the wrong decision. Yeah. You know, and you bring up an interesting point, kind of, I think it’s important to distinguish between change for the sake of change. Like some people have ADD and some people have shiny object syndrome.
And they’re just always looking to move on to the next thing and the next thing. And it’s like, that seems cool. Let me go there. Let me go there. Let me go there. No, like I’m a firm believer in work your ass off on an idea and do everything you can to make it work. And when I say testing, for me, most of the testing is within that concept, right? Like you’re testing features, everything we talked about, you’re testing, you know, copy and buttons and whatever. And it’ll start to point you in a different direction. I think for me,
Metwally — That One Time Podcast (28:32.974)
When to pivot, first of all, you have to be open to opportunity. Like for us, the Facebook opportunity that I mentioned, that was a once in a lifetime opportunity and you have to be willing to go for it. Those opportunities generally don’t present themselves. It’s more about, do I feel like I have tried almost everything with this concept? Do I feel like I’ve hit a wall? With all pause, when I ultimately decided to sell it,
I was either going, if I didn’t sell it, I was going to pivot away from pet adoption. I thought I had kind of taken it about as far as I could take it. Does that mean that I couldn’t have run some more tests and gotten 10%, 20 % more traffic? No, of course not. Do I think I could have made the business 10 times bigger given the resources that we had at the time? No. And that was the realization that I felt like I was hitting a point of diminishing returns and I was starting to run out of great ideas to test.
I think I had sort of maxed out on the initial concept. And that’s when I started testing other things on the side and started to see some interesting results there. Yeah, interesting. So with the Facebook opportunity, how did you actually find out about that opportunity? I actually don’t remember. My gut is either myself or my brother, my co-founder probably read an article in TechCrunch or something and decided to check it out.
I don’t remember the first moment of how we found out about it. there any common places that you go to find bleeding edge good ideas? These days, really it’s more about the people I’m surrounded by and the communities I’m in. And again, this goes back to kind of get yourself into rooms that other people can’t get into. I’m in a couple of great communities for entrepreneurs, for post exit founders.
whether it’s inside the group chats or the Discord or just networking with those people or going to meetups, that’s where I think a lot of my kind of leading edge and just staying on top of current trends. And the other thing I do, I’ve really made a conscious effort to work with, partner with, network with, keep in touch with really smart younger people.
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who are in the trenches on these things, whether it’s AI, personal branding, content creation, influencers, et cetera. That keeps me in the know and keeps me from becoming a dinosaur. Well, mean, Rick Rubin famously always works with people that are much younger than him. And he says it keeps him on the bleeding edge of ideas. So it’s definitely something that’s done. Absolutely. It keeps you youthful. Especially in a time like this,
where the pace of innovation when it comes to technology is so rapid and everything is changing. I the ground is literally shifting beneath our feet, least for those smart enough to realize what’s going on, whether it’s with AI, content creation, the overall implications on marketing. So yeah, I think it’s super important. Yeah, definitely. So how do you get into the right rooms where the right people are?
Number one, don’t be transactional. Transactional people suck. I hate transactional people. think, especially when you’re younger, it’s about being curious. It’s about giving. Give, give, give to get. But find ways to stand out. For anybody who’s on LinkedIn or Twitter or even Instagram who has big accounts,
There’s always people soliciting you with offers like, could do this. I’ll write you 100 tweets until you go viral or the next one’s free. And they never think about it from the perspective of someone like me, where, OK, if your tweets suck, then it’s work for me. So solve a problem in advance. Figure out if you’re trying to impress somebody, like you’re trying to get into someone’s orbit who’s a few steps ahead of you.
figure out a problem that they have and solve it for them. Be like, hey, you know, I saw your post and I saw you were trying to do X. I did this for you. If you like it, great, you know? But other than that, it’s also, it’s about being interesting, right? Be an interesting person. so many of these networking events are, what do you do? What do you do? Like...
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Learn how to stand out, learn how to juggle, learn how to do card tricks, learn a skill, learn how to story tell. mean, storytelling is a superpower. Find some way to be interesting, be someone that people want to be around, or just work your ass off to build something great and people are going to be drawn to you. Yeah, yeah, for sure. So how do you not be transactional in your relationships when you’re coming up? It’s tough.
I think you have to, if you’re not fortunate enough to be born or be in the right circles, yeah, you have to be willing to take some lumps. You have to be willing to do some stuff for free. You have to be willing to do some outreach where, let me say this, a lot of people when it comes to this stuff are lazy. The amount of messages that I get on a Twitter or a LinkedIn that are just, you
standard cold outreach. They’ve done no homework. They’ve done no anything. Especially in this day and age with AI and automation, it’s not hard to stand out. Like, example, you just mentioned the swiping feature, right? That’s not something that’s widely known. Spend a few minutes, do your homework, learn an interesting fact about somebody, do something that will capture their attention and go, you know, like,
I think in general people want to help, particularly people a few steps ahead of you. And the kind of people that want to help are the people who are ambitious and who are going to take your advice and where you’re going to feel a sense of reward for helping them, not people who sitting there with their hand out expecting help. Yeah, for sure. For sure. Just quickly though, I love doing this podcast. If it’s positively impacted you in some way and you would like to support us, please subscribe by subscribing.
It allows us to build a much bigger base of listeners, which results in better guests, better production, and a better show overall. Alternatively, please take a look at the affiliate links of the products that I use and love in the comments below and consider purchasing using those links. They’ll give you a discount and they’ll also provide the podcast a small kickback. These are two very easy ways for you to support us as we continue to grow the podcast.
Metwally — That One Time Podcast (35:34.68)
that we absolutely love doing. Thank you for your support. And now back to the episode. What’s been the most interesting outcome from networking that’s impacted your life positively recently? So Steve Jobs has a quote, you can only connect the dots looking backwards. You can’t connect them looking forward. And I think about almost every aspect of where my life is today. And I can trace it back to steps I took two, three years ago.
that started with breaking out of my comfort zone, writing on Twitter, which at the time I wasn’t comfortable with, but I forced myself to start doing it. Writing on Twitter led me to meet someone who put me into this group, PEF, Post Exit Founders, also into another group for entrepreneurs. In that group, I met Levi, who’s my co-founder in the face of Syndicate 11, which you just mentioned.
Syndicate 11 has led me into rooms with top creators, influencers, actresses, models. It’s opened up a whole new world in that sense. Me. You. mean, we would. The Chronic Plus One. But this is a perfect example, right? I would not have met you. I would not have been on this podcast if I didn’t start writing on Twitter.
Because one thing doing writing on Twitter did, it made me much more comfortable posting in these group chats. Whereas before I would have been like, ooh, there’s 1,000 people reading it, including the CEO of this. Instead, it just became reflex to just respond. And I responded to a post that Levi did in one of these chats, which led us to talking. So there was this domino effect of just putting myself out there and doing things outside my comfort zone, getting into the group chats, getting into PAF, and meeting this whole
new world of people that, you know, has largely changed my life. So how did you, what was your framework of thinking around the decision to consistently post on X? Cause that takes some time to build. Yeah. It took me about four months of being kind of panicked and terrified before starting. And, you know, another great lesson I’ve learned over the years, just like there’s never a perfect time, just start. At the time I wanted to do more advising.
Metwally — That One Time Podcast (37:54.488)
I thought the best way to do that is build an audience. thought, let me start writing about things I’ve learned over the years, some of these lessons, and just start putting them out there and seeing who it resonates with. And ironically, I realized I didn’t want to write only about things related to advising, but I kind of fell in love with the idea of building a personal brand and just recognizing how important it was to build an audience in this day and age. yeah, that.
That whole process, what’s actually funny is when I started, when I was starting, when I prepared to start writing on Twitter, I started making a list of all these different stories, lessons learned, anecdotes, whatever. And then one day I just started posting. And I realized nobody gives a shit. I figured I had this image in my mind that like everyone I’ve ever met in my life down to my third grade teacher was gonna be analyzing every tweet I made with a fine tooth comb.
And you soon realize nobody cares. Like just post, just post about what’s on your mind and go from there. And the funny thing is, two and a half, three years later, I’ve never gone back to that original list. I never had to. And it was an interesting lesson to just start. The ideas are easy, but the execution’s hard. Like I say, the secret sauce is always execution. Yeah. And I like this quote that I heard Alex Hermosy make where he was like,
it’s easy to push something in your to-do list, but it’s hard to actually do it. And that resonated with me because I’m chronically putting things into my to-do list and then I’m getting stressed about it. And that flipped the whole narrative of being like, okay, it’s very easy to just chuck something into to-do list. Doesn’t necessarily mean it needs to ever get done. Same. That also goes to a point you made before about what are lessons that you’ve learned from the startup world that you’ve taken to real life. And one of the key lessons I learned from startups and from building
products is ruthless prioritization. To this day, I probably have 500 ideas for All Paws that even years after it was sold, I never got to implement. And your to-do list and your idea list just keeps growing and growing. you kind of learn. And one of my frameworks for when I launch a startup or a product, and I have now applied this to my life as well, are what are the one, two, or three things that absolutely have to happen in the next three months, six months?
Metwally — That One Time Podcast (40:20.918)
to drive the business forward. And focus there. And if not, it’s a distraction. And as tough as it is, cross it off your list. And I apply that framework to my life as well these days. Or I try to. I’m not perfect. Yeah, I’ve noticed as I’ve begun to get on top of the, I think the fact that I have ADHD, and understand the way my brain actually wants to work and how distracted I can get, I’ve started doing things like blocking out
Right now, my priority is content. I think content is the core pillar that will make the rest of the pillars easier. And I’m focusing on Instagram, just for the moment. And so I’ve made it my priority almost every day, the first two hours of the day, I’m just editing a video. And that’s it. And I’m slow, and I’m shit, and the start of videos suck so much. But every now and again, they’re starting to...
But you’re putting in the right. OK, yeah. And now the second thing I’m noticing is there’s been a number of really important tasks that I have in my to do list that swirl around in my brain for months that aren’t quite deadlines, but just I know I need to get done. And very recently, only very recently, I’ve started once a week just putting one of those tasks
into a full time block for a day and nothing else. I’m like nothing whatsoever I’m going to do in that day and anything that comes in that isn’t that task I’m not going to do. And even if the world falls down I need to sit there and do this one thing. And I’m starting to knock down things that I’ve put on the back burner for six months plus because I have to do it and forcing myself to go to like
not working from home or not even working from an office, just going to a room in the building that’s empty and sitting there because I’m so bored and I have to just do the work. Change of environment is so key. And I think that’s when people are looking for change and looking for to break a pattern or break out of a rut, I think people underestimate the value of a change of environment. Definitely.
Metwally — That One Time Podcast (42:42.542)
So it was building an audience with the goal to advise actually the right thesis. I think the idea was right. I think what I realized afterwards is it’s much more important to have the right audience. Yeah. Now don’t get me wrong, because there’s also an element of social proof. Like if you have 300 followers, nobody’s going to take you seriously. I don’t know what that number is and it really depends kind of on.
to someone having a thousand followers means something to someone having 10,000, 100,000, million, 10 million. They’re all different levels, but there is social proof to having a lot of followers, but I got a lot of my followers. What I’ll say is the wrong way makes it sound like it was shady. It wasn’t shady, but I did it on things that would go viral, even click bait. My biggest thread in all my Twitter was
top business lessons learned from Breaking Bad. And it got a three and a half or close to four million views. Elon Musk commented on it and it was great. And it got me thousands of followers. Didn’t get me an advising client. You know, I got an advising client from a simple post about, I don’t even remember, but something, you know, niche business related. So the right strategy is probably a combination. It’s, you know,
kind of content that appeals to the masses to gain following, but then kind of hyper-targeted content around your niche or geared to your target audience. But I do think for social proof, you need to hit some amount that gives your account credibility. Lately, I’ve been hearing about this concept of making content, even if it’s niche, but for your ideal customer avatar. Yep. And only doing that. Yeah.
And I’ve been thinking about it lot because I don’t really know the direction I’m taking things over like three or four different directions that have three or four different pieces of content. But it’s been floating around in my brain quite a lot. Like what is the ideal customer per avatar and what do they need and want? And then you make the content for that and then you let the algorithm figure it out. Assuming that’s what you want to make. Right. Like when I was doing when I was growing on Twitter, one of the things that stopped me was
Metwally — That One Time Podcast (45:04.578)
Look, I love startups. love growing, scaling businesses. But it wasn’t the only thing I wanted to talk about. And I realized, when I was trying to write tweets or threads geared toward my ideal audience, the entrepreneur, the company that was going to hire me to advise, it started to feel like work. Because that wasn’t what I wanted to talk about 24-7. And I was enjoying some of the more fun, let’s call it mindset threads.
You also have to feel passionate about it. And audiences, I mean, can pick up on passion and authenticity for sure. know, failure is inevitable as well. In all of this game, it is inevitable. But what someone does with the failures, what sets the winners from the losers apart? So what was the time where you had a massive failure and what lessons did you take from that experience that helped set the stage for the next success?
Yeah, that’s a great question. I couldn’t agree with you more about how your response to failure is a key determinant of success. And this game is humbling, this game being the startup game, right? of life. And life, yeah. Game of life is humbling. And how you respond to failure. I don’t know, especially when I think back over my business career, that I can point to kind of some movie-worthy moment of a crash. Exactly.
went down in flames and rose from the ashes. going back to the fact that I kind of come from this testing mentality, I feel like 99 % of my ideas fail. Yeah. Like whether it’s an idea for a feature that didn’t work, an idea for a dating site that didn’t work or didn’t work as well as we’d like to an investor that I thought was for sure going to invest and didn’t, to a fundraise that didn’t go the way we thought we were going
it was going to go to a partnership that we thought would work out that didn’t. Startup life is littered with failures on a daily basis, and especially if you’re doing it right. So I think just being comfortable with failure and being comfortable with knowing that, if I’m writing a tweet, 99 % of the ideas I’ve tried have failed. just knowing that’s part of the game. failure is only final if you fail to learn from it. Yeah, for sure.
Metwally — That One Time Podcast (47:31.214)
So co-founding two companies with your brother sounds like a recipe for disaster. So how did you keep the relationship intact while also maintaining the high quality outcomes in a company you were a part of? We just spent Thanksgiving together. we are intact. yeah, co-founding a company with a family member is incredibly difficult. Co-founder relationships in general.
are incredibly difficult. And I think people underestimate them because in a lot of ways, it’s similar to a marriage. It’s just you have to have shared values. It’s only worse with a family member because if things don’t work out, the ramifications can spill over into your family life, your interpersonal life, et cetera. I think whether, but my response is really the same, whether it’s a family member or just a co-founder relationship in general.
You have to be super clear on expectations. You also have to understand each other’s values, your moral compass, your appetite for risk. Almost kind of just go through different situations. somebody you asked before about reinvesting in the business. One co-founder might want to be conservative with money and not reinvest. The other might. Where is one person willing to push the envelope legally, morally, ethically?
and another one isn’t. I think you have to kind of run through those scenarios or just know the person well enough to understand that in advance. So as I said, for me, with a family member, it’s just the collateral damage is greater, but the approach and the premise is still the same, that you have to be aligned on expectations and all of those things I just mentioned. How do you know whether you’re aligned?
Talk through these scenarios with them, depending on- Before you stop. Before you start, or if you know somebody already, you have a feel for them. But even if you do, people are different in business. Like money, people are always weird when it comes to money, right? And money and business are largely synonymous. know, vet a co-founder the way you would vet somebody that you were going to date, right? Like get to know- Get a private investigator onto them. Of course. Follow them around for two weeks, right?
Metwally — That One Time Podcast (49:53.486)
without question, right? Run a background check. Only half kidding. you know, you, right? Like if you were going to date somebody, like you don’t marry them on date too. And a co-founder relationship, same thing. Like people can get excited over the idea of working together, but really just through a series of conversations of asking the tough questions. You know, there are coaches, there are therapists that specialize in this. And the beautiful thing is in this day and age,
AI or otherwise, there are so much free available resources out there. Just put in the time and understand that this is something that a lot of people take for granted or don’t do enough work on. And this is massive because businesses blow up over bad co-founder relationships. Yeah, definitely. So wrapping up on this component of the episode, you’ve advised startups on growth and digital strategy now, If you could pick one or two
unconventional pieces of advice that you give founders that come from your playbook, what are they? I’m going to give you something I think I feel very strongly about and I feel like a lot of founders don’t do it enough is spend a lot of time either responding to customer service emails or
doing customer service or being with your customer service people. Especially as companies grow, founders, executives tend to get away from customer service. I always kept a hand with Snap, with AllPause, in responding to customer service emails or at least overseeing what was going on. There’s no better way to get a pulse on what your users are thinking than to be interacting with them directly and seeing what
their frustrations are, what their pain points are, what are they writing in about? And I’ve actually said, I don’t envision where I would ever work for anybody, because I think I’m probably unemployable at this point. But if I ever did and someone said, wanted to hire me as a CEO or any executive level function, and said, what’s your day one or first week activity? The very first thing I would do is spend time with customer service.
Metwally — That One Time Podcast (52:15.854)
To me, I think that’s somewhat unconventional, but I think it’s integral for understanding the business and especially the clients or customers. Yeah. Nice. So wrapping up, I’d like to explore a few philosophy, well, philosophy of life questions. So what views do you have that make most people either scratch their head or potentially get angry? Rush is the best band on the planet. Rush. know who Rush are. See?
Are you angry scratching your head? I’m definitely scratching my head. Are you angry? No, I’m not. Yeah, because I will be. I guess one view that I have that makes a lot of people angry is that ideas are essentially worthless because it comes down to execution, as we’ve talked about. Execution is always a secret sauce. I think you can give 20 different people the same idea, and they’re all going to execute it differently. And the level of success comes down to the execution.
I think a lot of entrepreneurs get frustrated with that. Similar to that, I believe that asking people to sign an NDA to hear an idea is absurd. I was guilty of that in my early days of being so protective over an idea and not realizing that it just makes you sound like a rookie. You should share your idea with masses. You don’t have to share some of your proprietary data or business methods, but in general, if you can’t talk about your idea,
Or you’re worried that someone’s going to steal it because you say, I’m going to do video dating, or I’m going to do a pet adoption platform. There’s basically no idea that hasn’t been thought of. Paul Graham was famous for saying, if you think your idea is so great, go ahead and try to sell it. The fact that there is no marketplace for buying or selling ideas tells you that ideas in and of themselves are inherently worthless.
What’s one of the biggest things over the last couple of years you’ve changed your mind on? Okay. One of the biggest things I’ve changed my mind on, I think is building an audience. We talked about me starting on Twitter and quickly growing at 20,000 and realizing that I didn’t have the audience that I was looking for if I wanted to advise. And then when I realized that I didn’t necessarily want to advise as a full-time thing,
Metwally — That One Time Podcast (54:39.064)
There’s not a lot of value. I didn’t want to post content just for the sake of posting content. And for me, I always thought like building a brand, a personal brand would kind of future proof myself. And I still believe that. But I think there has to be vision, passion, and authenticity behind it, not just posting for the sake of posting. anybody can go to AI, even in this day and age with video quality, and have AI spit out
whether it’s a tweet, a thread, a viral LinkedIn post, an Instagram video, people are smart. So if there’s nothing behind it, just having followers as a vanity metric is not going to get you what you need. Followers does not equal monetization. Yeah, definitely. You’ve seen that very clearly with Syndicate as well. Some of the big followers, not so much impact.
What’s one of the most beautiful things you’ve created? That’s a great question. Beautiful things I’ve created. Snap, Are You Interested was 100 plus million users. All plus was millions of users. And to me, most of business is business, right? Whether it was an online dating site or a pet adoption platform or whatever, I’m still looking at the same charts, the same stats.
dashboards, same Google Analytics back in the day. And what I often lost sight of, but every once in a while was reminded of, was the fact that we were responsible for creating probably hundreds of thousands, if not millions of marriages. And I’m responsible, you know, as a pet lover, this really rings true for me. I’m responsible for tens of thousands or hundreds of thousands of pets, you know, dogs, finding a home, getting adopted. And
You know, and I think about kind of my contribution to the earth, to the world, my life, my legacy. I know that I impacted a lot of people’s lives, even in a bit of, you know, a small way and maybe not in a small way, but obviously that’s a big way, but in an impersonal way. And none of those people who dated or got married through our app or who adopted a dog, a cat, a ferret, you know, through all paws.
Metwally — That One Time Podcast (57:00.942)
They didn’t know me, I didn’t know them, we didn’t interact personally, but I know that I impacted life, lives on a grand scale of millions of people. it’s really, you know, it’s kind of cool to think about. Yeah, it is. I mean, if you’re do something, you as well do something that’s gonna help others. Yeah. Yeah, makes it lot more fun. Wrapping up, is there anything you’re excited about at the moment you want to let our listeners in on? I’m excited about...
the state of technology. I’m excited about all the innovation in AI and what this is going to mean for the world. Also scared by it. We’re in a dynamic time and a really interesting time. And I think a lot of people outside this world don’t realize just how quickly the ground is shifting. Also very excited about what we’re building with Syndicate 11 and the
I think we’re going to really meaningfully change lives. I talked about how we change lives with Are You Interested and with All Paws. I think we’re changing lives and we’ll continue to change lives with Syndicate 11. And that’s, to me, a big part of what life is about and what your legacy is when you look back on your life. Yeah, nice. And where can people find you if they’re interested? Twitter, at Daryl Lerner.
linkedin at Darrell Lerner, D-A-R-R-E-L-L, L-E-R-N-E-R. And Instagram is D Lerner, L-E-R-N-E-R, 2112. Cool. And wrapping up, my last question for you is, what do you think the meaning of all this is? Why are we here? You know, that’s a really interesting question. And it’s one my view changed on after my dad passed away unexpectedly about 10 years ago.
I don’t know that I have the answer, but it made me, I don’t know that anyone has the answer, right? But it made me think about kind of after you’re gone and everyone who’s listening, everyone out on this planet right now, in all likelihood, will one day die. Maybe they’ll live forever with the longevity movement, but assuming we’re all gonna die, I think it’s about experiences, making a difference and
Metwally — That One Time Podcast (59:18.412)
just doing what gives you joy and satisfaction in life. You know, realizing we have a finite amount of time on this planet, you know, just try to make the most of it. Right. And for me, when I think about my life, all pause, having an exit with all pause, having an exit with snap, I know that I got to do something, experience something that most people will never experience. Right. You know, all pause started as I was sitting in a room, writing ideas on paper.
two and a half, three years later, PetSmart, nationally known multi-billion dollar company handed me a large check. Most people will never get to experience that. And just for me in my life, like just knowing that I got to experience something that very few people ever experience, you know, that’s really cool and it’s a great feeling. And it’s something I want to keep doing. I want to keep experiencing things that other people won’t get to experience or nothing stopping them other than just, you know,
going after things that they want to go after, working hard. Beyond that, we’ll go back to Rush. Why are we here? Because we’re here. Roll the bones. Why does it happen? Because it happens. Roll the bones. That’s right. Thank you for your time. My pleasure. Great to be here. Appreciate it. And if you enjoyed this episode, please go to YouTube. Search That One Time with Adam Metwally. Click Subscribe, and I’ll see you next week. Cool, man.
