Swim Downstream | Raj Singh at Loop Team

In part one of my conversation with Raj Singh, the co-founder and CEO of Loop Team, he talked about his efforts to make remote work feel more connected and productive.

In this second part of our conversation, Raj discusses how his previous startup brought him to this remarkably prescient venture, and how his company has met the challenge of their product becoming so direly relevant, quite literally overnight.

More information:

Raj Singh is Co-Founder and CEO of Loop Team, a virtual office for distributed teams. Previously, Raj Co-Founded Tempo AI, a smart calendar acquired by Salesforce, Co-Founded AllTheCooks, the largest mobile recipe community-acquired by Cookpad, served as VP of Business Development for Skyfire, the first mobile browser that could play Flash acquired by Opera, Co-founded Veeker, NBC’s first mobile video citizen journalism service acquired by WMG and ToneThis, CNET’s top downloaded ringtone creation product.

Raj has also worked in product management, engineering, strategy, and consulting roles for numerous companies including Kodak Mobile, Dell Mobile, AOL, Blackberry, MobiTV, Tellme, Samsung, Turk Telekom, IGT, and others. Raj blogs at his LinkedIn and invests via AngelList. Raj received a B.S. in Computer Engineering from Cal Poly, SLO.

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Raj Singh 0:00
I have learned repeatedly from startup after startup that it takes two to three years. So if you have conviction around the hypothesis, don’t give up so soon, you know, keep keep working, keep iterating you’ll eventually figure it out.

Alexander Ferguson 0:21
In part one of my conversation with Raj Singh, the co founder and CEO of loop team, he talked about his efforts to make remote work feel more connected and productive. In the second part of our conversation, Raj discusses how his previous startup brought him to this remarkably prescient venture and how his company has met the challenge of the product becoming so direly relevant, quite literally overnight. Roger, I’m excited to continue our conversation and hear now more about the journey that you’ve been on in the last two to three years. Tell me first off, was it as simple as Oh, great, I got it. We’re launching now everything’s perfect. And now let’s, let’s go, or what? Can you tell me some of the some of those kind of stepping points that got you to where you are now, three years later?

Unknown Speaker 1:06
Yeah, absolutely. Not that simple. It never is. Loop team isn’t my first startup won’t be my last. But usually, what I tell people is find an area that they find interesting. And so for me, it was sort of, you know, this, this married two different things that I found really interesting. One is meeting productivity, which has been a passion area for me, for quite some time. My last company was a calendaring company called tempo that was part of Salesforce. But the second thing was this remote work phenomenon. We had a partially distributed team in my previous life. And I could see that this was going to be picking up I didn’t know it was going to accelerate this fast with COVID. And so this sort of married to areas that were of personal interest. So then really, the next step after that was like, Okay, what exactly do we want to build? Or what is this going to look like? And so we just started swimming, what I like to use the swimming analogy. And the reason I like to use that analogy is if you think of a river, you can either be going upstream or downstream. And so it’s much better to be going downstream. So go with the market trends instead of fighting the trends. And so you just start swimming in that direction. And then another sort of metaphor that I like to use is I really think of as like, like, we’re jello and then over time, it starts hardening. It’s, it’s like flying through the air, right, so like little bits fly off, and whatever. And he starts sort of taking shape. So we just started swimming in this direction, saying, hey, we need to build something to just allow more communication and transparency. And so we had built a, let’s call it at the time a web conferencing looking tool that was doing transcription. And it allowed you to share the meetings after the fact. And it was really about sort of creating more information transparency across your team. And then as we started diving in, we said, hey, part of this experience is just the speed of interaction, part of this experience is the presence. And it just started getting hardening started hardening further and further and further. And it’s an iterative process. You know, and and in every startup I’ve had, it’s never not taken two to three years before you sort of start figuring out if this is going to work or not, because that’s just the time it takes to just kind of go through that process. And there are some resets, and there’s a couple places where you may take two steps back one step forward, or one step, you know, whatever it is, but a one step back two steps forward, sorry. And, and in the meanwhile, you’re revising your messaging and positioning along the way. But it does ultimately harm. And you do get to a point where you can kind of say, you know, this is my positioning. And this is where we’re seeing people using it and how they’re using it. And it’s very sort of concrete, and people get it. And I think this is consistent across all all startups. I don’t think any journey is unlike what I’m describing

Alexander Ferguson 3:49
this being your second startup, what hurdles Do you see next, you’re going to have to overcome the that you are already able to do and another entrepreneur could learn from,

Unknown Speaker 3:59
you know, I? So I get this question asked a lot. It’s like, Hey, Raj, you’ve been doing entrepreneurship for a long time, I dropped out a master’s to start my first company in 2000. I tell them, each startup had a different sort of primary learning experience, it’s really hard to, it’ll take a whole hour to go through each of them. But there are there are some patterns. One thing certainly is team. It’s really important to make sure, especially the early early folks that you bring on your team are people you think you can work well with. But people who also can push you in the right direction and be contentious when they need to be contentious, but not sort of get to a point where it’s like very hard to get any work done. And you’re just arguing all the time, whatever. Team is really, really sort of important. Your best friend may not be your best teammate, you know, and that’s very key. And that was a lesson out of my first startup, which was out of all college roommates. And then it just became a egotistical match just because of our age being 2021 years old and all of that right so, team is super important. I think too, I think a lot of people get stuck in analysis paralysis, which is sort of like, I want to do something. But I’m not sure. And I started, I look into it, and I spent three months and I kind of give up. And then I move into some other idea. And I have learned repeatedly from startup after startup that it takes two to three years. So if you have conviction around the hypothesis, don’t give up so soon, you know, keep keep working, keep iterating you’ll eventually figure it out. And number one reason startups fail is they run out of money. But number two reason is because the founders get tired. You know, and so if the team gets tired, you just sort of step back. But so if you persevere, you will figure it out. You’ll figure out an opportunity and niche is only niche until it’s not niche, right? And we see that all the time now. Little ideas that people like, yeah, maybe 1% of the population would be okay with renting out a room in their house for a vacation. And next thing you know, it’s Airbnb, right. So that’s how these things sort of start. I would say in and that was what I’m describing here, this analysis paralysis, definitely a lesson from my second startup. My third startup, I remember, indecision or not my third, my last startup was sort of something we hit indecision, kill startups, which is a really, it may not make a lot of sense. But it actually as your team grows, it’s really important to communicate a decision when you don’t make a decision, it actually creates anxiety for other people. So if you’re not sure, that natural tendency of companies is to, or sort of first time founders is to, on hard decisions to just delay. Like, I’m not sure if we should do this or not sure if we should do that or not, if we choose this or choose that. So we just delay, and then they delay and delay. And next thing, no, it’s kind of too late. It’s actually better to make the wrong decision. Just make a decision. If it’s wrong, it’s okay. But at least now you can say we tested it, or we did it. It didn’t work. And then we pivot, because it creates a lot more focus around the team.

Alexander Ferguson 7:01
Curious and as over the years, what are where have you learned these different insights? What books have you read podcasts you listen to that, to that kind of are your favorites, or you’ve really enjoyed?

Unknown Speaker 7:13
You know, I enjoyed the hard thing about hard things. I think that was from Ben Horowitz. There’s other there’s a variety of popular business books, I increasingly don’t read them, I read the Cliff Notes, because I found you know, he read a Malcolm Gladwell book on the blink moment. But really, the rest of the book is just reinforcing the first chapter, which is kind of really what it’s about. And so I do look at a lot of the cliff notes. But I will say, doesn’t matter how many books you read, you’re going to make the same mistakes. If you could go read a jack Walsh’s biography on managing, you know, high performing teams or whatnot, and what he did, and your team grows, and you’re gonna make the same mistakes, you’re going to create OKRs, do all that, whatever, but you’re going to make the same mistakes. And the reason is, you can’t, you just can’t, it’s hard to apply what you read. In real life, when you’re actually in that situation. emotions come into play. You know, what your gut comes into play and think things that you may not recognize or realize. And so you do need scar tissue is real, and you have to get some scar tissue. But one thing for sure, that happens with repeat entrepreneurs with your first startup, every time you have an upper down, it’s like super exciting, or it’s like, you know, you’re you’re you’re super depressed, you get a little bit better about managing that you get to get to a point where a few things make you really excited. You know, you’re happy, whatever things are growing, but few things make you really depressed because you’re so used to the ups and downs after a while. I hate to say you almost become sociopathic because you become sort of emotionally emotionally immune to the roller coaster. But but my best advice here is the books are great. You know, maybe read the Cliff Notes, you don’t need to read them in detail. But honestly, what’s even better is just to go start building.

Alexander Ferguson 9:07
Awesome. Last question I have for you what kind of tech innovations do you predict we will see overall tech innovations in the near term next year, so and long term like 510 years,

Unknown Speaker 9:18
over the last five to 10 years, they’ve been talking about AI? That’s a term obviously comes up a lot. And I feel like we’re hitting a point where it’s moving from a category to a layer. And I think that’s a that’s a big deal. And what I mean by that is, for a long while it was only XYZ engineers who could do AI. But now the tools and the frameworks have improved so much around the surrounding AI. That people out of college people in college high school kids can incorporate elements of AI into their experience. And I think this is going to have a signature If it can’t sort of productivity gain across the world, from from very simplistic things, you know, to, I don’t know, self driving cars, as we talked about, you can think of that simplistic to more more complicated things. But, you know, just the the thought experiment I like to tell people is envision a product in your house, anything you can think of your clock, whatever, how would that product become better if it had access to AI? Like, what would it do differently? What would it do differently if it had access to location or if it was connected online, and Amazon’s been doing a great job pushing our minds forward here. They’re taking all these devices and made them internet connected. But really, the next step is AI. You know, if I walked in my fridge, how could it do better? If it had AI? Well, certainly, it could reorganize everything in the fridge for me, to make it easier that the expired items come to the front or whatever it is, right. And so that’s always a good thought experiment to think of. And I think this trend is not a sort of next year. Next, it’s going to be going on for the next five or 10 years. But I think, you know, an analogy I used to use is in 2007, when the App Store came from Apple was 2009. But before before Apple, even the the carriers that app stores, they used to have a category called location. And these were applications that used location data. And today, it’s sort of hard pressed to even think of like what application wouldn’t benefit from knowing location, right? Everything uses location data. The same thing is happening now. And

Alexander Ferguson 11:38
that concludes the audio version of this episode. To see the original and more visit our UpTech Report YouTube channel. If you know a tech company, we should interview you can nominate them at UpTech Or if you just prefer to listen, make sure you subscribe to this series on Apple podcasts, Spotify or your favorite podcasting app.



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