Evolve Podcast
A podcast about heroes solving the world's greatest challenges.
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Why You Must Take Back Your Learning

Featuring Guest -

Shireen Jaffer

Headshot of podcast host.
hosted by: Brandon Stover
November 24, 2020

Shireen Jaffer is the Co-Founder of EDVO & Founder of Skillify. She went from working multiple part time jobs since the age of 14, even being fired from a yogurt shop, to helping over 50,000 people in their careers over the last 10 years, from recent grads to executives. She is a Forbes 30 under 30, an active angel investor in several successfully growing startups, and a founder of 2 startups that have been aimed at building innovative educational tools to empower lifelong learning for billions around the world.

Changing how people are educated and see work in our society, she has supported 220 schools to equip students with real world skills and worked with hundreds of companies, from Fortune 500s to early stage startups, advising them on recruiting and hiring practices. This year she launched products to help people think think for themselves including the world’s first personal learning management system and a mental models app which was #1 on product hunt with over 15,000 users in the first two weeks.

She shares her wisdom for a life full of meaningful learning, critical thinking, and better results as host of the Edvolution Podcast, as a Ted-x speaker, and has been featured in numerous publications such as Business Insider, Fast Company, Forbes, and more.

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what you'll learn in this episode

  • Shireen's journey from Pakistan to Palo Alto and what it taught her about self worth.
  • What Shireen learned about work ethic starting to work at age 14.
  • Why Shireen was working dozens of part time jobs as a teenager.
  • The problem Shireen saw happening inside her high school that led to her first startup.
  • How Shireen started helping students learn skills to get jobs they ACTUALLY wanted.
  • The realization about education that made Shireen pivot her startup 4 times.
  • The amazing biological behavior that is taken out of us by the school system.
  • Why self agency in education is powerful and necessary for a healthy society.
  • What is a personal learning management system?
  • How to empower people to find knowledge for themselves.
  • What are mental models?
  • This simple mental model that changed the course of Shireen's life.
  • Why so many people are living on someone else's terms.
  • How to overcome self doubt as a founder
  • What the education system should look like today.

How Shireen Believes We Can Push The World To Evolve

I think we can understand each other better. I think we can ask more questions. I think that's what it is. I think when we go into conversation, instead of focusing on, okay, I need to be right. I need to clearly communicate. I need to make sure I'm saying the right things instead of keeping the focus on yourself and how right you want to be. Focus on just understanding and asking questions. Because I genuinely believe if you start asking questions and getting to know other people and their perspectives ,you're going to start empathizing more. And I think empathy will help us evolve. I think empathy will help us recognize what problems exist for people. A problem you might not feel might be such a detrimental problem for virally large population, and maybe you feel inspired to help solve it. I think evolution will be a natural result of people just wanting to genuinely empathize and understand each other and just gaining perspectives.

Selected Links & Resources From This Episode

Connect With Shireen Jaffer:

EDVO | LinkedIn | Instagram | Twitter

Want to hear another founder changing education? — Listen to my conversation with Ben Nelson, Founder of Minerva and education revolutionary going head to head with the ivy leagues to lead the transformation of global higher education for 21st century students.


Get the podcast show notes delivered directly to your inbox. Plus get inside access to Brandon's startup as he #BuildsinPublic!


Shireen Jaffer Interview

Shireen Jaffer: [00:00:00]  trying to have people, very large amount of people who don't know each other who see the world very differently, who all come from very different education lenses who don't have the tools to make sense of things they're expected to come together and find a common way of moving forward that serves everybody like how crazy does that sound? Right. So our education system like a really good one is meant to help people make sense of the world and then come together to have thoughtful discourse and reach a collective consensus.

Brandon Stover: [00:00:53] Hey everyone. Welcome to evolve.

Today's guests went from working multiple part-time jobs since the age of 14, even being fired from a yogurt shop to helping over 50,000 people in their careers over the last 10 years from recent grads to executives. She's a Forbe's 30 under 30, an active angel investor in several successfully growing startups and a founder of two startups that have been aimed at building innovative educational tools to empower lifelong learning for billions around the world.

Changing how people are educated and see work and our society, she has supported 220 schools to equip students with real-world skills and worked with hundreds of companies from fortune five hundreds to early stage startups, advising them on recruiting and hiring practices. This year, she launched products to help people think for themselves, including the world's first personal learning management system and a mental models app, which has been number one on product time with over 15,000 users in the first two weeks.

She shares her wisdom for a life full of meaningful learning, critical thinking, and better results as hosts of the evolution podcast. As a TEDx speaker and has been featured in numerous publications, such as business insider, fast company Forbes, and more.

I'm honored to welcome co-founder of edvo, founder of skillify and an entrepreneur who married her co-founder, Shireen Jaffer.

Shireen Jaffer: [00:02:10] Thank you so much for that kind introduction. I'm happy to be here, Brandon.

From Pakistan to Palo Alto

Brandon Stover: [00:02:15] Absolutely. Well, I'd like to start actually kind of at the beginning of your story and hear about, you know, your journey moving from Pakistan to Palo Alto, that's a very big change. and what you kind of learned from that transition.

Shireen Jaffer: [00:02:28] Yeah, that's a great place to start. So. My, parents always have valued education for my brother and I, and you know, they saw that in Pakistan, the quality of education we were getting, even though they enrolled us in some of the best schools, despite being a pretty middle-class family, you know, public education there isn't free, so they had to pay for it.

but they did everything they could to just get us access to quality education for them. They believe that. If you know how to navigate the world, if you know the skills, if you understand how the world works, you'll be able to create a life for yourself. So that was really their motivation. So long story short, you know, my mom got as a healthcare professional, she got.

Sponsored, in a very rare situation, actually, she got sponsored by this like nursing healthcare facility in Palo Alto. And it's so rare for immigrants, to move to a place like Palo Alto, unless, you know, they're in tech and they're getting sponsored by like companies. Right. And especially when I moved in the early two thousands, you know, I found myself.

In Palo Alto, pretty much like the only Brown kid growing up in this very affluent white city and something I learned very early on is that I'm different. And, I was so fortunate that Palo Alto is this like liberal community, very welcoming. you know, we got so much support. My mom got support.

People were so nice. I never really saw all my color. So I never thought I was different because I'm Brown at all. I never really saw my color. it wasn't commented on really from what I remember as a kid, but how I knew I was different was, what access I had to different opportunities. So I saw a lot of my friends, you know, going to summer camp and being enrolled in a million extracurriculars and always having something to do after school.

meanwhile I would, after school be in the library, like reading a million books because my mom had to, you know, finish her job in order to come pick me up. So I would just, you know, do whatever I could to keep myself busy. So that's probably the biggest thing I learned. In that move is I'm different.

And that means I'm exposed to a different set of things, which means that if I need to find success and I'm only able to verbalize this in hindsight, of course, but, even as like a middle schooler and early high schooler, I saw. You know, the way success was defined for us was going to college and going to a top college, right.

And get a degree, at an order to get to a college, you had to be this well-rounded student. So success was defined by being a well-rounded student and getting into college. Then I had to do things differently in order to get access to college. so that was kind of the start of my understanding of my self-worth and what I needed to be able to do.

That would be different from everybody else.

Brandon Stover: [00:05:21] Yeah. Can you talk about, sort of the idea of hard work and building a work ethic? You watched your mom worked several jobs, and then you started working at 14. How did that impact your journey to success?

Shireen Jaffer: [00:05:33] Yeah. So I think the reason why I started working at 14 was it was less about, Oh, I need to work hard, but it was more about, well, I need to pay for things because people tell me I need to go to college. And so if I need to go to college, and then the only way I can get in is to be this well-rounded student.

And that means I need to take curriculars and go to summer camps, you know, salt really silly, but then I need to be able to pay fees for summer camps and extracurriculars. And I can't go to my mom. Who's working three jobs. I can't tell her mom pay $10,000, right. For a semester's worth of activities. So I need to do that myself and.

That is probably why I started working. So seeing my mom work gave me an understanding of reality, not so much work ethic. Like of course my mom worked really hard and I feel like I know the importance of. You know, committing to things and following through on things and it does get easier and you just stick with it, you know, and you don't make, I learned a lot of that, that tenacity and endurance from her, for sure.

But I would say initially the biggest thing watching my mom work, the way she worked was understanding the reality can be very different for different people. The reality from my mom. Was very different. you know, as a single mother with two kids in Palo Alto, no family, is that's very different than the reality of my friend's parents.

And then the reality of my colleague at the Kmart, I worked hat who was teenage mother and had no parental support. Her reality was totally different. So that's what that exposure really did for me.

Teaching Students Real Skills

Brandon Stover: [00:07:16] Hmm. Can you talk about how, you know, you shifted from working all these different jobs, getting into college and then going into your first startup of skillify?

Shireen Jaffer: [00:07:27] Yeah, so totally unintentional. I think most things early on seem unintentional, and then you realize there was always an intention, but, so all the jobs I was doing part-time again, was to just. You know, get experience right. To make my college resume look good. Like literally that was why I was working so many part-time jobs.

and yeah, it was, you know, to make money as well, but really that wasn't the main motivation. So that got me into college. And then once I was in college, I realized I was like the only kid, I guess I wasn't really a kid. I was the only 18 year old, the only freshmen who understood. That my worth in the real world, isn't going to be defined by my grades and my test scores.

It's going to be defined by how I deal with my boss and how I communicate and how I stand up for myself and how I ask questions and how curious I am and how I'm able to find answers for myself, right? Because the four years of exposure to all these different part-time jobs in high school made me realize that.

You know, I, I think I got my first job in real estate after one conversation because I was able to communicate. Well, I was able to advocate for myself. Like no one asked me don't even think that person asked me my age, honestly. so, so that's what led me to start skillify. My first startup at 18, I started it because I realized my friends, even though they had amazing, you know, high grades and high test scores and they were all at USC, they were struggling with all this anxiety about.

Oh, shoot. How do I get my first internship? What even is an internship. What do you mean? I have to like talk to adults and interview, like, why can't they just look at my grades and give me an internship? Right? Like all of a sudden, you know, for so long, they were told, just get into a college and if it's a good enough college, you'll be fine.

And now they're in that good enough college and they're realizing they're not fine. So that's what actually inspired me to just start helping my friends, how to get internships because I'd had a resume since I was 14, I had done so many interviews by then. I just wanted to share my skillset now. That was kind of the intentional unintentional part, right.

I was intentionally helping, but I did not start out to start a company. It just evolved into me realizing, Oh, this isn't a problem that only my friends have. It's a problem that like pretty much every single person at USC has, Oh, this is a problem that pretty much every single person in any university has.

Oh my gosh, this problem starts in high school. And I just kept. Working and helping people. And one thing led to another, and now we have a company that's really what happens.

Brandon Stover: [00:10:18] and you've helped, you know, over 5,000 students, you know, in that initial first bit doing really successful with scale of five. When did you decide that edvo needed to come in the picture and, you know, move on to that?

Shireen Jaffer: [00:10:31] Yeah. correct something. So skill of, I actually ended up working with over 150,000. Beautiful. So in the five, four and a half years, but I bootstrapped it as a solo founder. We ended up, you know, helping students from over 220 high schools and universities. We were primarily in high school and, you know, through the programs that we built and through the curriculum we implemented in these schools, you know, tens of thousands.

And then ultimately up, if I had to take. I guess of like how many people have gone through the programs? It's a little over 150,000. how that led to advo because our students, right? Like our skill of my students, these are kids that I've been doing internships. Since they were like 14, right?

Because I was replicating my own experience for, for skillify. So they've been doing internships since they were 14. They've learned how to network, because skill, if I taught them how to network, they know how to advocate for themselves because skill, life skill. If I focused on that, right. So they have everything they're tooled to have to then get a job that they would actually like.

Full time. And so we had all these skills by students like graduating over the years and then entering the full-time job market. And they were coming back to us and saying, Shreem why is finding a job that I actually want still so hard. If I have everything I'm told to have? why can't I still find it?

And so that kind of spurred the idea of. How do we actually help people get jobs they want and not just, you know, it wasn't just about just getting any job offer. Right? Our students were getting job offers, but they were from companies that they didn't want to work at. And, or they were just like schemey company, whatever it was.

And so EDVO started two and a half years ago as a recruiting company where we reversed the recruiting, incentive structure, where instead of working with companies to help them find people they wanted, we worked with people. To help them find companies that they wanted. and that's what initially started EDVO, but then in the last one, a half years, we had, you know, another world of realizations and recognitions of really what the root problem is, and that's why we pivoted.

but that's what brought me to EDVO.

Teaching People To Think For Themselves

Brandon Stover: [00:12:41] Yeah. So can you talk about what that root problem is and kind of like the, the conflict that you had of, you know, going down this one path with EDVO and then deciding to pivot?

Shireen Jaffer: [00:12:50] Yeah. So in the first, year and a half of EDVO, we probably pivoted like four times. So we pivoted from being a B2B SaaS company because, you know, B2B, SaaS as much easier than consumer. even though I love consumer, I think B to C is so much more fun, but B2B SAS is easier. It's more investor friendly.

So we started there and I had the realization that wait, we cannot be accompanied for companies. We have to be a company and a product for the people, right. Or the, or the actual consumer. So then we shifted to a B to C model, but then our business model was wrong because it was still incentivized to work for the companies, not the candidates.

So then we went completely consumer, even in our business model. Once we did that, we ended up helping, you know, over 5,000 people get jobs and we had like incredible retention rates. it was all working really well, however, in January of this year. So in January of 2020, I was doing an audit of how we were coaching people to get jobs that they found meaningful.

And I realized it. The first trigger was the people. We helped get jobs. They were still coming back to us even after they got the job and they were happy with it. They came back to us and said, okay EDVO. Now I trust you. You were able to get me to a goal that I didn't even think I could hit. Right. The, the, The realization of, Oh my gosh, I actually have a job.

My life that's so foreign to people, which is sad, but like, yeah, that's so foreign to people. So now they're like, Oh my gosh, I trust EDVO. But now EDVO tell me what to do when it comes to getting a promotion. Now, EDVO, tell me what to do when it comes to managing my team or dealing with my boss, right.

It was this constant. Tell me what to do and I'll do it. And I had this moment of like, Oh my gosh, everything I've done in my head career ever since the day, one of skillify. And even before, and you know, the, the volunteering I would do and the little side projects I would do everything I've always done has been to help people become self-sustainable right.

At skill. If I could have built an internship placement program or a mentor matcher program. And I didn't because I wanted school, if my students to have the skills so that no matter how old they got, they had. The skills and the awareness to find the opportunity. And here I was at EDVO. Turning into this glorified coaching agency that was teaching people how to gain the system.

We were literally telling them here's what to do. Here's how to think about it. here's what to say in the interview to get the job that you actually want, blah, blah, blah, blah, blah. We were teaching them how to game a system because it is a system that needs to be gained. It's not their fault, but that wasn't making them self-sufficient hence they were coming back to us and saying, okay, now what right now, what do I do?

And. In addition to one, I never really wanted to start a coaching agency. but two, I had the epiphany of, huh. Do people know how to think for themselves? Like you can Google and find so much content on how to manage a team and how to, deal with a boss and how to even get a job, right? Like how to really get a job.

There's so much content on there. Like there's so many people trying to fix this problem of this like job search and whatnot. So there's all this stuff out there. Then why can't people figure it out for themselves? Why do they keep wanting playbooks and step-by-step guides to tell them what to do? And so that took me down a rabbit hole early this year.

To just understand where this dependency and desire for playbooks comes from. And then I had that aha moment, Oh, our education system gives us textbooks and it tells us, this is your syllabus, and this is what you're going to learn. And this is when you're going to learn it. Right. You learn these things in ninth grade and then 10th grade and then 11th grade.

Right. It's so prescribed. And so of course, if. As people we grow up in a system that preaches prescription and preaches following the rules and following the latter. Right. If it preaches following the breadcrumbs, then that's what we default to. We want those breadcrumbs, we want that syllabus. We want to be told what to do and.

I S I thought about my experience working with like early childhood development programs. So I got exposed to all of these, like two-year-olds and three-year-olds and five-year-olds right. And I noticed, wait, as kids were so curious, and of course, there's so much research done on this, and people have talked about this, but you know, we're curious people, we are born curious.

We are born asking questions. We are born investigating and wanting to touch everything and try to figure out if it's a good thing to touch her or not. Right. And somewhere along the way, it's kind of taken out of us. And, and so we lose our ability to think for ourselves. And that's what I wanted to fix is I wanted to see a world where all of us feel free to think for ourselves because that's what we're built to do.

It just gets taken away. And then every day, frankly, we're constantly under attack by, you know, different advertisements and societal norms that this is how you should do things. And this is what it means to be successful when you're bombarded all the time. And then you aren't even equipped with the skillset to think for yourself and investigate and question these narratives.

Then of course, you're just kinda, you're gonna survive. You're just gonna do what it takes. And so now at edvo and the realizations we've had that has led to our current emphasis, which I think which I know, which I believe in my core is, you know, what, what we're going to build at EDVO is. Imagining a world where people can think for themselves and forge their own stories.

And so that means, you know, forge a life. They actually want to live on their terms that makes them feel fulfilled and productive and meaningful and whatnot. And so my answer, and there are many answers to this and all of those answers are needed. But my approach to contributing to solving for this problem is.

Change the way education, works, right. Change the way people are taught to learn. So if we can for adults, if we can introduce a new way of learning that encourages investigating and encourages questioning and encourages, you know, it's okay if. What you think today is wrong tomorrow. Like it's okay to change your mindset.

It's okay to evolve your perspective. and, and just equips people with the tools to do all of that. Cause that's hard. It's going against what they're taught to do for so long. If we can do that, then hopefully we can impact the way people think about their lives. Then maybe they'll start saying, well, why do I live this way?

Is this my choice or was I just told that this is the way to live. and, and hopefully that thinking that trickles down to their kids or the kids they mentor, because having worked with kids, kids have no problem being curious. Kids have no problem. Questioning kids have a problem. Being empowered and encouraged.

Keep that questioning going. So this isn't a kid problem. This is an adult problem. If I can help adults go back and rediscover their curiosity and for adults like me who are already curious, I've. I went through a painful process of having to rediscover my curiosity. But now that I'm already curious, having an environment where that curiosity is empowered, even more than that will trickle down to the kids I'm around and giving them environments to keep their curiosities going.

So that's what we're currently doing.

Brandon Stover: [00:20:19] Yeah, I think this idea of, you know, personal learning of basically seeing what education is for yourself, being curious, going out, finding those things. It gives a lot of confidence in yourself, a lot of self agency in your life. so that you don't have to say even. You know, you have a medical problem. A lot of times people just go to the doctors, say whatever the doctor says, right?

They, they get that prescription instead of looking it up themselves, researching and figuring out, going with the questions to an expert, but then making the decision for yourself, getting advice from an expert as a resource, but not just listening to them.

Shireen Jaffer: [00:20:55] Exactly. You nailed it. Brandon, it's getting advice as resources, right? Getting again, you know, get multiple perspectives and then learn how to. Really analyze those perspectives for yourself. And this is a tedious process, right? I mean, a lot of people have talked about sense-making and the war on sense-making and how do we make sense of the world?

And why is it so hard to even understand how this world works? Right? Like everyone has an opinion and fact checking things is almost impossible these days. So, absolutely it's it's about really giving people. Framework for sense-making that's individual so they can rely on themselves. Ray Dalio, for example, in his book principles, going back to your example of, you know, medical advice, you know, he had mentioned he had a medical scare and I don't know who, I don't remember the details.

I read principles a while back, so I'm not going to specify the story.

Brandon Stover: [00:21:48] I believe it was, a brain tumor or something along those lines.

Shireen Jaffer: [00:21:52] Thing. Right. And, he, you know, got some of the best medical doctors and physicians in the world on a call with each other. And he noticed how they, because they were so focused on being more agreeable and quote unquote respectful. They weren't really debating. On what is the right course of action. So if that's taking place in, in such a, more frankly neutral, possibly more of a welcoming environment that imagine what happens in the larger scale, more riskier environments where you're less likely to speak up.

Right. And so it is absolutely up to each of us to find the best answers for ourselves and both my husband and I went through this in our own personal lives, you know, the stress of the start of life took a toll on his body. He ended up developing gout, which is.

Which can manifest from high stress in the body. And he was put on all these prescription drugs that made him feel absolutely terrible. And so then he had to do his own investigating and go on his own quest to figure out how can you live a healthier lifestyle with gout that doesn't. Require prescription medication, because if they didn't work for him and he did find a solution and he's now two years free of any doubt flare up, I had a similar problem with things I was dealing with hormonally.

I was put on these prescription drugs. Didn't work, felt terrible, was told if I didn't go on them, that I would make my condition worse, but I went on my own quest and I found plant medicine. I found this like very specific route. That literally has reversed my diagnosis. So anyways, I wanted to say that because these are personal impacts of investigating and finding your own truth that, you know, I had to go on my own journey to then feel like, Oh my gosh, I feel like I discovered a secret and now I need to tell the world, but it's not a secret.

Many people have gotten here and realize, you know, we have to find the truth ourselves. We just haven't built tooling and software and just. Resources for people to be able to do that for themselves.

Introducing The World’s First Personal Learning Management System

Brandon Stover: [00:23:59] Yeah. And so you guys have basically started to undertake that building a personal learning management system. So could you share kind of what that is and a, it better helps to help people go through this personal learning journey?

Shireen Jaffer: [00:24:12] honestly, I have spent the last five years unlearning so much of what I was taught as a child and even as a young adult, right. And I've spent so much time questioning the narratives in my head, the narratives of society, I spend so much time being frustrated by my own inability in the time to like get deeper, you know, going down a rabbit hole was like, Oh gosh, I'm going to waste my time.

Oh my gosh. I'm just like sitting here on my computer, like getting lost in this endless, endless cave. Right. and I had like all of this resistance to learning the literally that's what I was resisting is learning for myself and. I started building, I started building reinforcers. I started build out understanding like best practices for retention and really understanding things and asking questions in ways that don't trigger biases.

I mean, everything's biased, but you know, that that athletes help you see things more objectively than not. And so I just started doing all this stuff for myself, my husband, you know, I'm, I'm, I'm an educator. So these things I actually get excited about. and so I created this framework and it took years.

For me to create a framework that actually mean my made me feel empowered when I learned and didn't make me feel resistant every time I was curious. and so I thought, okay, well, similar to what I did at skillify. I write, what worked for me, but I can possibly replicate and see if it works for other people kinda is the same thing at EDVO.

Okay. This worked for me. It's worked for my husband. It's worked for some of the most brilliant people in my life. So it can work for many people. Let me see if it does. And that's what made me build a personal learning management system. I realized LMS is, you know, they're an 8 billion plus dollar market, but they, they primarily focus on, they actually exclusively focus on schools and companies.

No, one's actually building an LMS for you as a person. Right? We, as people have task management systems, now we have knowledge management systems, but why don't we have learning management system? What is the point of. You know, hoarding, all the stuff you find online, all those information you find online in knowledge management system.

If you don't know how to take action on that knowledge, if you don't know how to make sense of it, if you don't know how to, evolve that knowledge, right. That's where learning management comes in. And I see a future where. Learning management systems and knowledge management systems, you know, partner together and integrate, but first a learning management system for the consumer needs to exist.

And so that's what we're building and personal learning is what it's called, personal learning by edvo. you know, we're in a closed beta. we've sent out about 700 in three days. We ended up getting like 1600 people on the waiting list, just organically. And I think that goes to show. People genuinely love learning.

They recognize learning feels hard. They recognize, you know, they're probably not doing the best job at actually truly learning, like truly retaining and understanding and relating it to other parts of their knowledge. And so they're demanding, you know, a better way to do better way to learn. and so we, we, gots 1600 plus people on the waiting list we've sent out about 700 invites so far.

And other people that have started using the product on a closed beta. I mean, we're getting such cool feedback and the biggest things we're learning is there are many different learning workflows. Right. People, you know, some people learn, very deeply, like they find something they're obsessed with and just go deep into a rabbit hole.

Other people choose to learn more widely. They want to learn a little bit about many things. what triggers. Someone's desire to learn. Something can be very different. And so we're understanding all these different learning workflows, and we're wanting to build a product that can elevate all of them.

Right. And of course, we're going to start with a few, but that can really work within your, natural learning workflow. That's really the power of a tool that works for you versus you having to fit it. so that's what we're doing so far. It's been three weeks. It's been three weeks since we've launched and it's going way better.

I shouldn't say it's going better than I expected because my expectations are always very high, but it's been going so well. And I'm pleasantly surprised.

Brandon Stover: [00:28:29] Hmm. I think the important thing was you mentioning that. You're basically empowering these people to, you know, find the knowledge for themselves, but then able to execute on that knowledge, do something within, not just, you know, there's tons of information out there. And what often people run into is like overwhelm of it all.  And then how am I supposed to do anything with it? So you guys are kind of helping to filter that.

Shireen Jaffer: [00:28:50] Well, I think the miss that's learning, right? Like, so I think the common misconception is you can learn without application, but you don't really learn something unless you know how to apply it. So if someone, you know, things that are learning right now, because again, they're just collecting a bunch of information.

That's that's, they're probably feeling the struggle of, Oh crap. I forgot what I learned, right. Or, Oh wait, how do I apply this to this specific context to, so, yes. what we're really doing is helping people learn, and that includes being able to apply their knowledge in multiple different contexts, because they understand the root of what they've learned and not just one use case for it.

The Power of Mental Models

Brandon Stover: [00:29:34] Hmm. The other thing I think it helps do is, build mental models for people, you know, their own mental models, which I know you're a huge advocate of. Can you explain what mental models are?

Shireen Jaffer: [00:29:45] Yeah, so, Oh my gosh, I love mental models. so mental models are just. Thinking frameworks, literally just how you think, how you approach thinking. So we all use mental models. We've used them since the day we learned at the thing, right? The day we started thinking and, the problem with mental models or not being aware of mental models is that if you're not aware that mental models plural exist, you're not aware that multiple ways of thinking exist.

And so if you're thinking in ways that don't actually serve you, that don't lead to productive, decision-making that doesn't lead to productive problem solving and people, I felt that anxiety right. Of knowing and my, the way I approach problems is all broken. Right? I'm making impulse decisions. I'm not being thoughtful enough.

Like I think all of us can verbalize those shortcomings in ourselves, but I think very few people recognize there's a solve for that. And the solve isn't. You got to get smarter because it's not like about being dumb or smart. It's about being aware or unaware. And unfortunately, mental models as a concept is not taught in school.

the way I got familiar with mental models. Actually came from my investing activities. When I became an investor, the more I started angel investing, the more I got involved with the investor community in the Valley, I started realizing, Oh, there's this thing called mental models. And people use it to make good investing decisions and Warren buffet and Charlie Munger.

They all talk about it. And then when I was going on my own journey of unlearning and reprogramming my mind, I started saying, well, why can't I just use mental models? To make good decisions about my life. So for example, circle of competence is a mental model that Warren Buffett talks a lot about that helps him make good investments, investments that are part of his competence.

Right. But that he knows enough about. and anything outside of his circle of competency, doesn't invest in well, I can apply circle of competence to my career. Right? How can I, what can I contribute to what skill sets do I have applying the circle of competence, mental model to your own skillset, to your own understanding of anything in life?

Well, that's, that's more than just investing. And so I started doing that and then I realized, wait, do other people think this way, do other people use mental models for their personal lives? And there weren't that many. And when I talk to people. Some of them had just polished their own thinking frameworks so much that they had actually implemented really good mental models, but they didn't realize that's what they had done.

And so that's where my desire to, again, just like I'm, you know, I'm the kind of person, if like, again, if something has changed my life, I want to introduce it to other people to see if it can help them. Right. It might not, but if there's even a 1% chance, it can, why would I keep it to myself? And so with mental models, same thing, I started just talking to people about it.

I put together. You know what three-day prototype where I said, okay. I think the problem with mental models today is, they're very complicated to understand there's a lot of content about it online, but that content is like long form articles that make you feel like you're too stupid because you don't even know these.

Samples that they're talking about. so how can I make this just really simple too, Dan, because mental models are actually really simple. And again, my educator side came out. I'm very good at curriculum. And so in three days I put together, you know, basic curriculum that could help people understand, based on what you desire.

So if you desire making better decisions, or if you desire more confidence in your choices, if you desire, you know, unleashing creativity, if you desire. Let's say you're remodeling a house and you want to know if you're getting a good deal. Like it could be something very big or something very specific.

It's usually a need. That then leads to discovering what mental models can help you think through that need. and then, you know, you figure it out. So that's the prototype that we created, it started with the need. And then it would tell you your mental models that can help. And here's a step-by-step guide on how you can apply those mental models.

again, as you know, I don't love step-by-step guides, and so we've evolved that, but at the time, just to test the idea, I put it out there and it was number one on product hunt. And people just started saying, wow, I've been craving mental models. If you actually go on product on pretty much anything related to mental models has become number one or number two or number three.

because people want to think better. They see that they need to think better because they want to feel happier. They want to feel more confident in their decision making, but there's not enough out there that makes it really easy to think better. Right. And so. That's. Yeah. Anyway, so that's mental models and, it goes hand in hand with how might we help people think better?

How might we help people learn better so that they can think better? And then how might we envision a world where everyone can do for themselves? It's all interconnected.

Brandon Stover: [00:34:39] Yeah. Can you give an example of maybe a major life decision that you've made using a mental model?

Shireen Jaffer: [00:34:44] Absolutely. funny enough, I actually started, I put together a tent free totally free 10 day think better challenge. where if you subscribe to it every single day, I send you one mental model, how to use it and how it changed my life. and if anyone is interested, you can join the challenge at any time.

If you go to think for yourself dot sub stack.com, or you can go on my LinkedIn and it's listed there as well. you can join at any time and you can really understand mental models. So one that I talked about, in this challenge and it's like the first story I always say when I was 21 and I had graduated college and I had a career decision to make, I was either going to go full-time with skillify

which wasn't making that much money at the time. or I was going to accept a job offer that was really good, at a large corporation. And, at the time every single person said, take the job offer, right. make your 80 K salary, which is ridiculously high for especially a recent grad. so I had this like amazing job offer and.

everyone said, take that job, offer, you know, learn your skillset to like, learn how business works, because I don't come from a family of business people. So, you know, learn how the corporate world works and develop the skillset. And then when you have enough money and enough knowledge, then go start, you know, go back to skillify, like restart skillify.

And that wasn't sitting well with me at the time. And so I, you know, did an opportunity cost analysis. Now opportunity cost analysis is a mental model. Now when I was 21, I didn't know what mental models were. Right. But that's why I tell people you've probably used mental models, your entire life and not known it.

fortunately opportunity cost analysis. As a mental model, my husband was aware of who was my then my boyfriend. so at 21 he was like, Shireen, why don't we just do an opportunity, cost analysis? And he was a big advocate for me going full-time it's skillify. He's the entrepreneur. He's been like my biggest, you know, Fan and my biggest mentor.

so he was like, don't take that job, go full-time and skillify. Let her an opportunity, cost analysis. And so in an opportunity cost analysis, you've got two decisions or two options. You can have more than two options, but you look at. What are the games, if you were to take that option and then what are the costs?

So it's not a pros and cons list. It's a gains and cost list. If I move forward with this option, what do I give up? What's my cost of doing this right? And so. At the time I said, okay, well, if I move forward with skillify, I give up, you know, one year of stability, I give up an $80,000 paycheck. I give up what one year in corporate America, like kind of forgotten the right, like you're not gonna make a huge impact the first year in corporate America.

So that really wasn't a cost, but I wrote it down. Right. but really it was, I would give up stability and I didn't think I would learn something tremendously more in. My first year in corporate than I would in my first year in Skillify. So it wasn't a cost for me. Skill-wise so really the only cost was I would give us stability, a nice paycheck.

that's it. Okay, great. On the other side, if I choose, the one year in corporate America, what do I give up? I give up, The ability to actually make something I know I love, right? Because I'd been doing school. If I, since I was 18. So by 21, I knew I loved this word. I hadn't, you know, I was a full-time student.

I was doing internships. I was still like, you know, I hadn't gotten skillify, to a point where I knew it could make money, but I knew I loved it. So the cost was I could be giving up a chance to make money from something I genuinely love. I could be giving up the chance of being an entrepreneur. I could be giving up the chance to learn exponentially fast.

I could be giving up the chance of having autonomy and dictating my life on schedule and working for myself. Right. So that cost list was so much bigger. Then the other one that all I looked at was okay, then what this means is I have to do skillify, but stability and financial freedom is important to me.

So what that means is I'm going to give myself a year to do skillify, but I have to make. The salary I would have made after taxes at that corporate job. So I think it was like 60 K right. I had to make 60 K in my first year. It's still a fine net, right. Net profits. because that would be my nuts salary to feel like I've made the right decision. And that first year I made 120 K. And profit. Right. So I doubled and I haven't looked back since, I mean, I did skill if I feel like I bootstrapped as a solo founder, I didn't for up until I was 24. And then I started to add both so and skillify. They still exist today. And that mental model y'all changed my life.

Like I met former president Obama through it, former president Clinton through it. I was the topic, social ventures across multiple, like different competitions, like. It changed my world and it changed my understanding of myself just to simple, simple, like it took me a week to make that decision. You know, and if I didn't know how to think about it, if I had done what everyone else told me, you know, you prioritize stability.

You prioritize having enough money in your bank account to take a calculated risk and blah, blah, blah, blah, blah. All of that advice is right in its own accord, but it depends on the context and it depends on you and what you want. And so mental models help you make the best decision for yourself. And if you use a mental model and then make a decision that ends up being not great.

Well, cool. You'll learn from it because then it will be able to backtrack what led you to make that decision so that you can understand that mental model doesn't work for you, but that's where you've gotta be thoughtful. And if you make decisions because someone else told you to make a decision, you won't be able to backtrack in the same way.

Brandon Stover: [00:40:35] Hmm. Yeah, that that's a powerful story and a great example of how learning can empower your life. How thinking for yourself can completely change the direction, rather than thinking, you know, through somebody else's, advice or, you know, whatever direction they say you should go.

Shireen Jaffer: [00:40:51] Yeah. And the challenges, I think we've all been. Living life on someone else's terms like always, I mean, I had that realization, because I realized, Whoa, the way I saw the world and how society works and like, you know, who has more power and who dictates the truth and like, who's the authority, all of that changed once I started thinking for myself.

And so I think all of us, all of us, there's not a single person in this world that did not. For a very long time live life on someone else's terms. And the majority of people today still live life on someone else's terms. And it's not as someone it's just like a, something it's some narrative, you know, some cultural norm that they were grown up in.

and that's where I think we're doing ourselves. The most injustice is. I'm not saying you got to change your life, man. Just, just start questioning. And if you love your life and the, the answers you come to feel good grades keep going. Like, I hope that for you, but for most people, that's not going to happen for most people like me.

It required a dramatic change, a drastic change. And by the way, when I made the change, I didn't even have to really see the results of the change to feel this way. But once I just started making the changes and started realizing how much more thoughtful I can be. I felt liberated in a really cool way.

And I was able to do more than I had dreamt for myself. I had non drempt, the life that I live right now, never in my dreams was this the life. Right. And seemed to me like, it's insane that I just achieved something that I didn't even dream. so it's, anyways, it's super cool. And I, and I wish that for everybody.

How To Overcome Self Doubt As A Founder

Brandon Stover: [00:42:31] You've talked about, you know, rewiring your brain having to come over beliefs. Can you talk about how you overcome self doubt as a founder and, you know, working with money and all of that?

Shireen Jaffer: [00:42:43] Oh, my gosh. Okay. So the reason why I react this way is that's all recent. Like, I think a lot of people listen to entrepreneurs, right? And listen to people who found quote, unquote, societal success. And they look at their accolades and they say, Oh man, this person probably figured it out so much earlier.

I did not overcome self doubt. And I can proudly say, I have overcome the majority of self-doubt now, but I did not overcome self-doubt until six weeks ago. Six weeks ago and the reason what's so as an entrepreneur for me and every entrepreneur has a different journey as a woman, a person of color. Does not come from entrepreneurial family. you know, went through traditional education. Someone like me, I was told that being an entrepreneur was like dreaming big, you know, it's like, it's something you just don't do. Right? Like, all my friends, you know, growing up like. It was just not a thing in our reality. And so my self doubt came from more like imposter syndrome.

I always knew that I'm very good at learning. I knew that I can figure things out. I know that I have confidence. Like, you know, I've got a good personality, blah, blah, blah. Right? Like I knew those things because I worked really hard to develop those things, but I always felt like, well, am I smart enough to build a business that impacts every single person on this planet, because that's my ambition. My ambition is not to build, you know, Like my ambition is to build something that actually creates impact at the highest level, which is it needs to touch every single person on this planet. So am I smart enough to do that?

Am I well-resourced to do that? Am I, you know, do I know how to talk to the right people and like scheme, like, you know, all this BS that you're taught as a business person, like, am I, can I do all those things? And so a lot of my self doubt came from. Frankly me not resonating with the way things were being done, but feeling like I had to do it that way to get to my end destination.

So this summer on my 27th birthday, I remember on July 9th, I set a goal. My said, I've recognized that in times of adversity, when you know my business pivots, when things aren't working, when there's massive change, I default to self doubt. I default to, I'm not smart enough to do this. I default to, I need someone else's help.

I default to all this, like just negative, you know, beliefs. Right? And so I said, I no longer want my default to be that. I want my default to be okay, cool. We'll figure it out. Okay, cool. Like I know I have what it takes to figure it out. I might not have the exact skillset to just do it, but I know I have the skillset to figure it out.

I've done this enough. I know. I want that to me, my default. And so I got a coach, I got a mindset coach and I found one that I resonated with. And I committed to myself that I was going to not make impulse decisions. I was going to be very thoughtful and that coach helped me put in, you know, daily practices for myself to reinforce, positive beliefs to help me reverse limiting beliefs.

I now talk about this in my newsletter every single week. but that's. How I started. It was the commitment of, I don't want my default to be self-doubt. it was actually the awareness of knowing self doubt was my default. Then the commitment that it shouldn't be, then actually investing money, which there's a whole conversation around money, but investing money to then get help. With reversing, this limiting beliefs that I had to them having the discipline to actually every single day practicing the things that would help me reverse it. And I kid you not six weeks later, I've documented this in my journal. I'm not someone who used to journal. I didn't start journaling until like July 9th.

and ever since I've started journaling, I can tell you in six weeks, Was probably when I had my breakthrough, I started realizing, Oh my gosh, I'm not defaulting to self-doubt anymore. I default to more productive thoughts and more productive actions. And then that changed pretty much everything. For me, it changed how I saw money.

It changed how I saw, what it, what it really changed is it helped me realize everything. Every belief I held that was limiting. So, for example, with money, I was taught to see money as bad that wanting money is greedy. So I was condemning money all the time. I was thinking, and that made, you know, raising money for EDVO. For example, when we were raising our seed, it was really awkward. Right. Cause I'm like asking for money. So it wasn't until I broke through my own self doubt that I opened up space to then question every single belief I had and look at it, not as a me problem just as I, okay. This is a belief. Where does it come from?

Does it serve me? No, it doesn't. How do I reverse it? What my relationship needs to be with it. And then that just kicked started a ton of reversal of that, and then beliefs since that. So very recent. Very pivotal moment of my life. and that just goes to show that there are phases to this, you know, there's like peeling the onion, right?

There's multiple layers. You have to unlearn and get to know. and that's, I mean, I think being an entrepreneur has, for me, it has accelerated that it has accelerated the self-discovery. Because I am responsible for the work I do. I'm responsible and accountable for what I bring into the world. And what I bring into the world for me must be beneficial.

It can't be harmful. So I'm always thinking through second, third, fourth, fifth order consequences of my work. So now I've got to be thoughtful. I've got to even learn what it means to have second order thinking as a mental model. So I hope that answers your question.

What An Education System Should Look Like

Brandon Stover: [00:48:32] yes. Based on all of your, your experience you've worked in and out of the education system, based on all your experience of learning and overcoming beliefs. If you had a magic wand today, what would an education system look like for you?

Shireen Jaffer: [00:48:49] Oh, my gosh. That's very And education system, I believe the role of education. is to help people make sense of the world. And so this is an education system that first and foremost is. Of the highest quality, which means that it cares about the educators, right? It has a proper incentive alignment. So people that are doing the, I wouldn't say teaching, right.

I don't think teachers jobs are to teach us to facilitate is to ensure that the learners have support. So it's first even redefining what a teacher is and then ensuring those. Those educators are invested in that they, have the tools to be the highest quality. but the environments are set up for people they're blended.

So I believe in remote and in-person instruction, I don't believe in one or the other. so the environments are set up to be, empowering for both the educators and the learners and the focus. So focus is not. I have an agenda and I need to teach people this skill set so they can be a good employee, or I need people to learn, you know, the civil war from this perspective.

So they can be more empathetic to this type of people instead of this type of like, none of that needs to exist. It needs to be very objective. This is what historically happened. these were the impacts of it. Let's go analyze the impacts. Like let's go see it from different perspectives. Let's go investigate, you know, will someone else have a different understanding of what happened?

Let's see it from all sides and come to our own decisions. Let's, let's give people proper sense-making frameworks because once they can make sense of things, then they're prepared to have. Conversations where they can collectively come to a consensus of how this world operates. Once they can have a collective consensus that again, or originates from thoughtfulness and perspectives and empirical, you know, frameworks of, of investigation, right.

Once we can do that, then we can have a democracy and have a Republic that actually functions with. the tools and the understanding of how the world really works today, we live in a world where we don't know how to make sense of things. And so literally everything, the propositions, you know, that, that we're trying to get approved.

Other than the elections, the everything it's like a 50, 50 split, right. Everything gets passed at like 51 49 or 60 40. That means at any given time, half of our population doesn't agree. And here we are as a democracy. Trying to like have people, very large amount of people who don't know each other who see the world very differently, who all come from very different education lenses who don't have the tools to make sense of things they're expected to come together and find a common way of moving forward that serves everybody like how crazy does that sound?

Right. So our education system is meant like a really good one is meant to help people make sense of the world and then come together to have thoughtful discourse and reach a collective consensus. That is not how it is today. Instead today it's a game. It's a, I can graduate more people than you can.

Right? I can. You know, incentivize them to make more money than you can. I can build better partnerships. So my graduates get better jobs. And even if they're miserable, who really cares. And even if they can build lives that they find fulfilling, who cares because Hey, more Harvard grads get, you know, better paying jobs, right?

Like it's the incentive structures are so misaligned across the board. and so we're so anyways, yeah. So if I had a magic wand, I can't even imagine, like using a WAM and this just happens because it's such a large. Global problem. So if I had a magic wand, you know, I would, I would want, like, I wish that aha moment went into people's heads and everyone just became more aware.

I think that's what I would do with a magic wand. Everyone just became more aware and wanted to then use that awareness to actually move forward collectively and not rebel, but actually move forward collectively and say, Oh crap. Okay. This is what's. Really happening, how can I individually make better sense of things?

How can I help other people make better sense of things? How can I participate more and let my voice be heard, any constructive, thoughtful, productive way? How can I recognize that, you know, what are the tools available to me? You know, is social media actually a tool that helps me or hurts me or can it be both?

And I need to understand how to balance it. Right? If I had a magic wand, I would probably do that. And then I think that. Will result in many changes in our society, including our education system that helps people really make sense of the world so that they can build a life for themselves that feels good and feels productive and feels meaningful.

Brandon Stover: [00:53:41] Hmm. I love that. before I get to my final question, where can everybody find you in the tools that you're putting out in the world?

Shireen Jaffer: [00:53:47] Yeah. So the best way to reach out to me is probably on LinkedIn. so Shereen Jaffer, if you Google Shareen, Jaffer, Edvo, you will see me. everything I do is like in my about summary. So my podcast is there, been product. We just launched personal learning again in closed beta, but please, if you. One access to it.

If anything, I said vibes with you, get in touch, use the product, sign up for it. all those links are on my LinkedIn and my email is on my LinkedIn. I love hearing from people. Literally my Q4 goal is to hear from as many people that resonate with what I'm seeing, what I'm saying. Talk to me, share your perspectives.

If you disagree, please reach out. Tell me because honestly, my only goal in life is to build a product that can actually help every single person think for themselves and build a life they want. So get in touch. That's the best way to reach me.

How Shireen Believes We Can Push The World To Evolve

Brandon Stover: [00:54:36] wonderful. Well, my last question is how can we push the world to evolve?

Shireen Jaffer: [00:54:40] So I think, evolution comes from multiple things, but I think we can help. I think we can understand each other better. I think we can ask more questions. I think that's what it is. I think we, you know, when we go into conversation, instead of focusing on, okay, I need to be right.

I need to clearly communicate. I need to make sure, you know, I'm saying the right things instead of keeping the focus on yourself and how right you want to be under focus on just understanding and asking questions. Because I genuinely believe if you start asking questions and getting to know other people and their perspectives.

You're going to start empathizing more. And I think empathy will help us evolve. I think empathy will help us recognize what problems exist for people. A problem you might not feel might be such a detrimental problem for virally large population, and maybe you feel inspired to help solve it. Right. I think evolution will be a natural result of people just wanting to genuinely empathize and understand each other and just gaining perspectives.

Brandon Stover: [00:55:46] going back to that curiosity that we lost a long time ago.

Shireen Jaffer: [00:55:49] Yeah, curiosity, and just like giving a shit about each other, you know? And I think it's hard to do when you're in a survival mode because like your life isn't going on your terms, which a lot of us feel, especially in COVID. So I get it, my empathize too, like I do, I really, really do. but I think more people will find. Comfort when they started being able to relate to other people and you can relate to other people by first showing interest in them, right. Genuine interest. And hopefully that's reciprocated. And then hopefully that leads to meaningful conversation that then leads to meaningful opportunities and that leads to a meaningful life.

So, yes.

Brandon Stover: [00:56:27] awesome. Well, thank you so much Shireen for coming on the show and sharing your perspective, sharing about your tools. I really appreciate it.

Shireen Jaffer: [00:56:34] of course. Thanks for having me.