[0:05] Smart people tend to overthink decisions and under-leverage intuition.

[0:11] Jeff Bezos is famously known for his hard-nosed drive for efficiency, but even he says, all of my best decisions in business and in life have been made with heart, intuition, and guts, not analysis. I'm Rusty Gaillard, and this is Do Something Different, a leadership podcast to help you achieve your career and life goals. Today, I'm very excited to have Samir Qureshi with me. Samir is the co-founder and the CEO of Knack, an edtech company that provides a platform for peer-to-peer tutoring for students. Samir immigrated to the U.S. as a child. He overcame challenges in his own academic struggles.

[0:50] And he went on to found and lead a startup that has raised over $20 million in venture funding. Over the past decade, he's navigated all of the expected startup challenges, co-founder transitions, lawsuits, layoffs, everything that comes with running a company and he has built a company that is both mission driven and scalable so we are talking today about decision making samir welcome super happy to have you with us thanks russie pleasure to be here i appreciate it awesome so let's jump in i mean you've built this company that helps thousands of students after navigating your own struggles in school and i'm curious for you what part of this journey most relied on intuition and instinct for you.

[1:34] Yeah, it's an interesting question. I think there are a lot of moments along the way in different chapters of the business where gut played a huge role in the decision-making process. Honestly, even just the founding of the company in and of itself, I was working a corporate job and enjoyed it, was doing well, was on a track to keep doing well and likely be promoted over time. Um but there were so many things that were somewhere between serendipity and just sort of like opportunity that was flashing in front of me um and as i would sit with that on a day-to-day basis or late at night before bed something kept tugging at me around you know this this being a mission fit around what i cared about in the world but then more than that the timing and sort of the the momentum that was building behind the model that we ended up employing which is really based on the sharing economy or gig economy as many folks call it the uber-like sort of model that that really you know took flight and um and became commonplace uh call it 2013 to 2015, you know all of a sudden became okay or cool to get in a car with a stranger or stay at a stranger's home um and i think you know my gut read on that was that this wasn't a fad this wasn't something that was just going to go away it was a fundamental shift in um the way businesses could be created and services could be delivered.

[3:00] So as you kind of like look at the more data-driven side, you could take like the approach of looking at the growth of these industries and the rapid scaling of these organizations. For me, there was also the whole gut feeling of like, man, this just feels more

[3:15] exciting than just a lot of people. Then sort of having a more um you know stable path to uh to my career growing and building um but that's not that's not for everyone and for many folks like their gut feeling is probably no that's like that doesn't feel right for me because it's too risky or there's too many unknowns um so I think everyone kind of has that that their own unique gut feeling right and that's what I'm excited to talk about here today with you yeah well I'm interested because I've actually had that exact same experience, which is I had 20 plus years in the corporate world, including 14 years at Apple when I made the decision to leave and start my business as a coach. And honestly, it freaked me out. I was scared because of exactly what you described of, hey, I've always operated with a boss as a part of a big company. And now I'm going to go start my own thing. And like, you know, all sorts of fears came up for me.

[4:11] And I'm wondering if you have any insight or any advice or thoughts around this, like, how do you distinguish between this, this kind of intuition, which is pulling you towards something and your comfort zone or, you know, what you're afraid of that is holding you back? How do you distinguish those things? Cause it's, it's a little hard to know sometimes totally and there's very much a leap of faith i i don't uh claim that knack has done what it's done just purely because you know my gut feeling was right all the time and we worked so hard a lot of it's luck and timing and you know that's the unknown at the same time i generally believe that like when you have those feelings you should invite them and understand that that likely is the place where the growth happens right like where that the fear the uncertainty is, that's like being in a room where you don't feel welcome in terms of like being the dumbest person in the room or whatever is often where the growth happens and so for me i i think i for a weird reason i had many butterflies and many like knots in my stomach around like getting up something stable at the same time.

[5:20] I just felt like it was almost like adrenaline junkies that like to jump out of planes and skydive and stuff like that. Some people have this weird thing where, of course, it's scarier, it's a little bit exhilarating, but they still want to do it and it's still pulling them and they end up doing it. That's not me on that front but with starting a company you know it was almost like it was just giving me so much energy and excitement to figure out the earliest days when we had like literally drawings of our logo on pieces of paper like that to me was exciting now had i known how difficult it would have been um i probably would have been more skittish and probably would have turned myself off um i think being young naive you know honestly being um having a higher appetite.

[6:08] For risk because i didn't have a family or a wife or kids anything like that right i didn't have a mortgage so when i looked at it again like against my gut to the more like black and white dollars and cents of like how much risk can i really take at this stage it started to check out a lot yeah you know obviously so much of what you've done as an entrepreneur there's no playbook and even if there were a playbook every situation is unique you've never encountered it before you're having to navigate these things and i'm wondering if there's a time when you were navigating this where you ignored your gut and what you learned for that or if you wish came to wish that you hadn't totally um you know it's sometimes i think those moments hopefully folks can reflect on and then come back around and say now i can learn from that and not make that mistake again and for me that means like i i don't think there's a moment now where if my gut tells me something i'm not going to listen and ultimately follow it so a particular example was um you know we raised our series A round of funding kind of at the peak of the market. And there was so much emphasis and momentum on spending and hiring and just sort of like growing.

[7:29] And, you know, in some ways it made sense because money was cheaper and like things were inflated and like people were paying and using a lot of money. And so it kind of felt like it was part of the wave even the momentum.

[7:40] We raised our round right at sort of the tail end as that changed, as folks started to cut and the COVID sort of rosiness started to fall away in terms of what that meant for businesses and growth.

[7:53] And so from the moment when we signed a term sheet to when money was wired and diligence was all done, the market changed quite dramatically. And my gut along the way was like, we should probably change our plan and actually get conservative at this point because everyone kind of feels like a recession is now here or it's going to come and it's going to be heavy to deal with over the next few years. Um and so on our first board meeting i sort of uh you know postured this to the board to say look i think this is an opportunity to maybe learn from what's happening and we may need to actually make some changes to our plan and advisors and ultimately investors and board members around me were like this was the plan we sold uh and and the plan that we sort of like have postured up to this point this is why people bet on us we need to just kind of stick with it um so we ended up overhiring, we ended up overspending, we ended up, you know, taking shots on the goal that ultimately just didn't shouldn't have made sense to do. But we did because of that, or at least I did, as a leader of the company as as the pressure I felt, and I ignored my gut in that moment.

[8:59] Fast forward 18 months from there, you know, a lot of those bets didn't pay off. And I was sort of validating that feeling I had to change our plan more and more, to where at a certain point, We just had to pull the red cord and, you know, lay off almost 40% of the company. We had to right size a lot of our decisions on sales and marketing and pricing. And of course, that had a massive effect on the folks that we had to let go on the team at large. And of course, wasn't a fun thing to do from my perspective by any means. And so, you know, I made a decision and we made a decision after that as a company, as an executive team, that we'd be transparent with the team. Yeah. Going forward and that we were going to do everything we could to get profitable and not feel like we needed to be reliant on having external dollars and listening to really what we felt was best for the business not always going to get us more more funding to grow and so that was a pretty dramatic shift um i'll say almost every single person has stayed with us since um and my gut has never felt better and clearer about that decision and so that's sort of like, what we didn't do and ultimately what we're aiming to do now as we think about charting forward. Yeah, that's a great story. Thank you for sharing that.

[10:14] And yet it also highlights the challenge that you often face, which is there's disagreement. I mean, that board meeting you described is you were saying, hey, I think we should change direction. All your advisors, investors, everyone else was saying, no, stay the course.

[10:29] In the end, it seems like your gut was guiding you in the right way and you didn't listen to it. But it's challenging in an environment like that, especially when there's a power dynamic. You've got investors, you've got other people who are, you know, have more power than you, you know, guiding you in a certain direction. Um i know you you shared when we were chatting earlier a while ago you shared a story about pushing back on an investor more recently uh and i'm curious about like how you leaned into that uh you know because it takes some courage when you're when you're pushing back and resisting, someone who's in a more powerful position so i'd love to hear your thoughts on that yeah you know i think at the end of the day um, you know the operators know their business best and the best investors know that and therefore they try not to cross the line and and you know kind of the best phrase i've heard is their job is to be noses in fingers out and you know when fingers start to creep in uh or or sort of like you know advice is given that just doesn't feel relevant or sound to the degree that that's authentic from the founder to push back and that's done in a way that's respectful and can be direct, but it can also be respectful and not violating sort of the values of just being a good business person or being a good person more generally.

[11:52] You know, I tried my best to, you know, not let emotions get in the way and sort of tarnish or taint the way delivery was handled from my perspective.

[12:03] You know, and I would ask a lot of questions back to them to say, if you were in my shoes you know wouldn't you want to do this if not why not so try to invite them into a conversation but ultimately you know i i had to sort of say hey respectfully disagree and at the end of the day like we're the operators and you've trusted us to operate and we haven't led you astray in terms of the company still alive and growing uh and we see a you know a great opportunity ahead to continue um and they ended up saying hey you know fair point and um appreciate you kind of doing what you're doing and so there is a bit of an uncomfortability of course but at the end of the day um if it's again authentic and genuine and you're doing it in a way that upholds values you know i think you have to be able to go to bed at night knowing like i didn't do anything wrong i'm just sort of you know knowing what i know being in the trenches and trusting my gut ultimately so yeah it's not fun but it's necessary and how you handle it is ultimately everything yeah i think there's a lot about that is how you handle it makes such a difference to be able to walk out of a disagreement with someone with respect and you you can disagree and you say this is the direction we're going to go and they respect you for it i think there that's a uh that says a lot obviously for the way you interact with people um one of the things i think that's interesting is talking about this kind of um.

[13:28] This dynamic, I think a lot of people, not only in the startup world, but I know you've also worked in larger companies. You said early in your career, you did. And especially in those kinds of companies, there's a power dynamic, right? You have a boss, you're supposed to defer to your boss. Everyone has this mindset of like, well, my boss asked me to do this. I have to say yes. And so this whole idea of pushing back and so on, and even not only that, but data-driven, I think, especially in large companies, there's an expectation that you can justify your decision with data, with rationale.

[14:00] There's a little bit more understanding, perhaps, in the entrepreneurial world

[14:04] that you can trust your gut. But in a big company, that's all it's a lot about data. Do you agree with that? Is that consistent with your experience? Yeah you know i think a lot of that probably comes from when you have a large data set you know you don't need to be taking as many assumptive swings um and i think that can sometimes get in the way of large companies because they feel like well in the past all this data has validated what we've done and therefore we need to continue whereas startups are oftentimes like trying to find.

[14:32] You know finger in the wind to really like build that data set and understanding what direction they should go in and ultimately that starts by making assumptions um and so i think those assumptions come from intuition come from taste right like everything from design to um like even copy and the more creative side of things um and then there's of course like the more what have other companies done like how large is the market there's like the empirical side of it and i would definitely say that in startups there is more of that creative like leaning into what feels right and also having the the sort of mindset of rapid testing and evolving that quickly whereas larger companies i think naturally start to become set in their ways and start to feel entrenched and have these more um you know like prescriptive approaches that come from the top yeah how would you like if you're if you're talking to someone whether they're in a startup or in a larger company um and you.

[15:31] How would you advise them to tolerate risk a little bit more? Because, you know, part of this trusting your gut involves risk, because there is no right answer. You don't know how it's going to turn out.

[15:41] And I think that's probably what holds most people back. So how would you talk to someone about that managing risk?

[15:48] Yeah i mean i think it's um it's the best way for companies to innovate and grows to take risks and to test and ultimately you can test in small environments so you don't have to you know go and put your entire income or family or organization at risk up front you can de-risk it by starting small but still take a risk right and so you control that and therefore you don't feel like you've sort of uh you know just gone all in up front um at the same time like i thought about this in the in the context of knack and starting it because when i was when i was leaving uh uh gardner yeah one thought is like i could have just like been very quiet and moonlighted for a long time until i saw enough signal and left um but at the same time i also felt like jumping in the deep that and just like committing would almost force me to figure it out. And sometimes there's a dark side to that because, you know, you feel like you're into, you've like, oh, I took the leaps and now I have to figure it out. And you add so much pressure on yourself or your identity becomes that because that's what you are now. You're no longer an employee or a founder. And so it can definitely get out of sync and can be a little dangerous. But I do think had I like played a lower and slower approach. When things would have gotten hard, I probably would have rested on my laurels at a corporate job and been like, oh, I tried something as a side gig and couldn't really get it going. Whereas when I was all in on it.

[17:16] It did sort of feel like i had to figure it out and i couldn't figure it out because you know heat and pressure creates diamonds so it's sort of like maybe that was good and and i think when you're younger and when you're trying to formulate like what you want to do where you want to go taking bigger risks especially as a young person i i advise as much as possible to do so that could be taking a gap here that could be building while you're in middle or high school you know that could be uh graduating instead of taking the corporate gig offer like going to a younger company or starting something of your own i think the younger you are generally your risk is lower and and people should really really consider starting yeah i don't know from your experience or from talking to others what do you think blocks people from having that level of trust in themselves i think a lot of people have those desires that you just described but they.

[18:06] Somehow something gets in their way and i'm curious like what you see that is yeah so i'm a huge fan of rick rubin um i'm like i play music and love music and rick rubin is like this enigma of a person if you know who he is he you know essentially produced some of the greatest artists of all time red hot chili peppers and others but he's not a musician um but he is a creative and he's a producer like he doesn't get behind a computer or he doesn't pick up a guitar or piano like he has this like magical aura about him and i think he wrote a book um called a creative way creative act um and he talks about how so many people don't create because they don't think they're a creative um and in the same way i think so many founders like oh i'm not a founder like you know because i didn't go to x y or z school or i don't have network or i don't know how to be a builder or whatever and especially now um rusty where you can literally vibe code your way to having an mvp out the door like.

[19:05] There's almost no excuse if you really have that drive the only thing i think you have to overcome is like your internal fear which you've talked about right as you left apple uh and ultimately taking that leap and you know a lot has to feel right ultimately going back to gut um and i think that's the biggest thing to validate is like does this feel right in all places and does it check out against the data with my gut and if so you know i i don't honestly don't think there's ever been a better time to be building and taking a risk yeah you know i am listening to you talk about that the thought that keeps coming to me to mind for me is that you're the story you tell yourself makes a big difference uh you know it's like if you're and i think this goes back to some of the foundational research around mindset is this fixed mindset versus growth mindset like what are you here to do if you're optimizing for short-term stability and success that's very different from optimizing for growth over the long term as a person. And, you know, you described starting NAC, and, you know, I had this experience when I left to be a coach. Like, I knew that was going to be a massive growth experience for me as a person, whether it was successful or not. I knew I would grow as a person, and I would come out better and stronger for it. And so part of this is the story you tell yourself.

[20:21] And I'm wondering if there's a particular way that you see yourself in this broader sense of you know your your journey of life and your career the whole trajectory of your career not just this phase but just the whole trajectory and if there's a way in which you're telling your story that you find it helps you navigate this this risk and trust yourself more yeah you know i think um as i think about um you know what i might do later on in life or what what would come next from here i think i'm sure i would hit that point again or it's almost like you know the the cycle has started again where i'm like what would i do and how would i do it and when would i do it and what should i do join something else or whatever and i think so much of it has to do with like what's important to me and ultimately uh if i have some of those real fears that i'm sure i'll have because once you've started one thing doesn't mean you have ultra confidence to do everything else like that comes back to kind of feel feel maybe that imposter syndrome or do i still have my mojo or whatever it is and i think um for me a lot of it has to do with.

[21:30] Just like looking back and reflecting to say well i did this before and how did i do it then and why did i do it then and like why can't i do it again and everyone has generally had to overcome something in their life right and that can vary in magnitude um but i think leaning on those past experiences is to say, like, I can do this. I've done it in the past. I'm here today for a reason.

[21:52] You know, I should take the leap. And I think one thing that, like, I'm a huge believer in, which sounds morbid, but I think is actually very... Very helpful at times from like a priority and like what's my next action standpoint is like simply asking if you run your deathbed and today was your last day like what are the 10 things you would write down you wish you could do and like you should just start doing them um and i think, ultimately no one knows how much time they have left and no one knows what happens after this and i think if you can get alignment on what's important to you and you can sort of make that bucket list the best thing you can do is try to check those things off and it's not easy it's not to happen overnight but if you can break it down into small steps and start making those actions every day um you can start to get there and so i try to look at things of like okay like if this really was my last day like how would i do it and and like how would i make this decision would i lean in or would i lean out and i think looking at things through that um sort of razor can be helpful um and so i lean on that at times too yeah well that's i love that perspective and i think it's a good place to wrap up because it's a nice holistic picture of what we've been talking about um samir this has been such a good conversation i appreciate you sharing the stories your experience um what you've learned and what works for you um if people want to check out knack or uh hear a little bit about your other thoughts what's what's a good way to do that.

[23:17] Yeah um our website's joinknack.com, on linkedin i tend to post a decent amount happy to engage with folks same with uh twitter x um so yeah would invite those conversations and uh really really appreciate you having me on today rusty was great awesome thanks so much samir all right thank you.