Today on The Startup Chat, Steli and Hiten talk about becoming cynical or jaded as a founder.

One of the beautiful things about being an entrepreneur for the first time is that you have this youthful and blissful mind. You feel like everything is possible and everything you learn is mind blowing to you. But, this state of bliss wears off as time goes by and you get more experienced.

In this week’s episode, Steli and Hiten share their thoughts on why new founders are less cynical than experienced founders, how to approach new ideas and much more.

Time Stamped Show Notes:

00:00 About today’s topic

00:36 The beautiful thing about being a first-time entrepreneur.

01:15 When new entrepreneurs typically start to become jaded.

01:55 How Hiten views cynicism in entrepreneurs.

02:16 How ideas can be fragile.

02:58 How Hiten reacts to new ideas.

04:20 Why you need to think through ideas versus shutting them down.

05:36 A quote from Jeff Bezos.

06:03 A hack that Steli has helped Steli in his entrepreneurial journey.

3 Key Points:

  • The more experienced the founder, the more cynical they are to new ideas.
  • People start leaning towards “why this CAN’T be done” versus “why this CAN be done”.
  • Ideas are fragile.


Steli Efti: Boom. Hey.



Hiten Shah: Cool.



Steli Efti: This is Steli Efti.



Hiten Shah: This is Hiten Shah.



Steli Efti: In today’s episode of The Startup Chat, here’s a quick episode I wanna … A topic I want to discuss with you Hiten and that is the topic of becoming cynical or jaded as a founder. Right? In the beginning, one of the most beautiful things about being a founder and entrepreneur, especially when it’s your first time is that you have this … The bliss of ignorance, right? You have this youthful beginner’s mind. Everything is possible. Everything you learn is like a mind blown new fact and it’s an exciting thing to start a company from scratch, you come up with a name, a logo, a landing page, the first birth of your product, you start talking to people. It’s super exciting. But if you’ve been doing startups and you’ve been a founder and entrepreneur for a minute, for years and you’ve done as many companies as you and I have done, right? As time goes by-



Hiten Shah: Yeah.



Steli Efti: We have more and more entrepreneurs that have been around the block and have done a few things already. It is hard not to become a little jaded, a little cynical. The more experienced the founders are that I talked to, the more I detect in them, and I’ve detected this in me as well, I’m not above this, a certain cynicism when new ideas are being discussed, new things are being discussed. People start leaning more towards why can’t this be done than on the why could this be done. I wanted to talk to you about this. How do you think about cynicism in startups and entrepreneurship and being jaded? Is this a good thing? Is this a problem? Is it not a problem? How do you think about it in general? What have you observed? Let’s just unpack this a little bit for the two of us.



Hiten Shah: I know you like quotes.



Steli Efti: Yes, I do.



Hiten Shah: I do too. It’s not necessarily a quote but it’s a line that somehow I picked up and apparently Steve Jobs said and it’s just this idea that ideas are fragile. I have this with some people around me. Not a lot, where their first impulse of an idea is to think through risk. I call it just thinking through risk. They’re not trying to shoot it down. They’re just like, why would this not work. Their, basically, way of processing the idea has to do with an immediate impulse of assessing risk of that idea instead of imagining what it could be. Those are two very different mental ways of thinking. I hear an idea and all I can think of is how do we make this work, how can it work. I imagine what it could be, what it can do for the business. All that is my first impulse. My last impulse is, “What’s the risk?” Which is not always a good thing and I think balance in this is really good. While I know other people who, I will mention an idea to, and immediately, the idea is taken into this systematic process of how’s it going to work, how are we going to do it, why can’t we do it, what about this other thing that we’re already doing and how does this relate to that and all these things that typically, when I have an idea, I didn’t even think about. I just had an idea. It’s just a damn idea. “Ideas are fragile,” is from Steve Jobs. He said that somewhere or Jonathan Ive, Jony Ive, basically, I think said that about him is I think really what it was. I think Jony Ive even said, often times, Steve Jobs would come in and say, “Hey Jony. I have this dopey idea.” He’s already coming in saying, “Yeah, I dunno.” That concept has been really helpful when I talk to certain people on my team in helping all of us think in more systematic and positive ways and more thoughtful about the idea. Not trying to beat it up at first and really thinking through, “Is this a good idea? Is it not a good idea? How do we evaluate whether it’s a good idea? Ideas are fragile. It’s just an idea. It’s like a thought. It doesn’t mean anything yet.” Right? It’s just something you need to communicate with someone else, especially when it comes to business ideas or new ideas and this idea that you get jaded over time is probably because you’ve heard a lot of ideas or you’ve tried a lot of things and they didn’t work. They just didn’t work.



Steli Efti: Right.



Hiten Shah: But don’t let that stop you from having a brilliant idea. That’s my kind of throw down and I’ll say one other thing before I let you respond and also tell me what you’re thinking about here and where this comes from. But one other thing that I really love again is Steve Jobs’ thing is he focused … Whenever they launched something or whenever something was done, all he would think about and say, I think I’ve said this before is, “What’s next?” A good friend of mine that worked at Apple told me that that was the mantra and that’s pretty impressive. At their scale, at their size, they do great things but all Steve Jobs cares about is what’s next. I think that, that relates to this because you can’t come up with what’s next unless we have ideas.



Steli Efti: Beautiful. All right, so I here your quote and I bring my own quote, my friend. Right?



Hiten Shah: Yeah. Let’s do it.



Steli Efti: If this is a quote show down, I’m not empty-handed here.



Hiten Shah: No shit. Okay.



Steli Efti: My quote is from another Founder, CEO that I know we both admire, which is Jeff Bezos, which is the quote of like, “It’s good to ask why but it’s equally good to ask why not.” Right? I think that goes to this asking why should we do this, why is this a good idea, why is the competition not going to be doing it, why is this useful to our customers but at the flip side of it, which is why not? Taking an approach of, “Maybe this is cool and why should we do this.” I think that I’m weird in the sense that very early on in my entrepreneur career, one of the things that I’ve kind of, a hack that I’ve established in the very early days of my many, many ideas was that I found a guy, shout out to Ramin, who’s a mastermind of The Startup Chat and who’ve helped us with the podcast for a long time. Ramin, from a very early stage on become my sounding board for new ideas and the process that we had and still have to this day in some ways is that I would go to him first with an idea that was very fragile and very early, but I would go with the intent for him to crush it. Right? I would offer very little resistance. I’ll be like, “Oh, I think this is a brilliant idea. It could be this, this and that, what do you think?” Ramin would think about it and be like, “Ah.” I’m like, “But think about it. Da, da, da, da, da, these are all the benefits,” and then, he’d go, “Yeah, but why about … How do you do this and what do you do about that?” I’m like, “Ha, I don’t really know.” I would have a very nonchalant way about it, where I would go … Well, I would just let him shoot them down and not even fight it too much and then, I would just let this slide and just take a day or two and see if I can let the idea go. If I can’t let it go, most of the times, the next day or two days, I’d be like, “I actually don’t think it’s a good idea either.” In that moment, I felt strongly about it, but now, I think it’s dumb.” But some ideas, even two days later, I’d still feel strongly, so I would go and try again. I would just take a second attempt and a third attempt and him giving me pushback was not something that would really crush my morale or make me think that I’m stupid, I should have more ideas which is a way for me to go about it, but then, what I used to do is I used to be the Ramin for many other people and I, at some point, realized not everybody is thinking about their ideas being crushed the same way that I was thinking about this. This formula might work really well for me and Ramin but it doesn’t work for most people. I had to adjust and be a better sparring partner, a brainstorming partner for people in the early days, the way you said it. It’s funny, for many years, I think I was hypercritical in the very early stages of ideas that people brought to me, would share, probably made me somebody that people didn’t want to discuss ideas with very frequently. I love the question framework that you offer with first, let’s ask ourselves, “How can we make this happen? How could this become a success? How could this work?” Maybe later, we’ll ask ourselves, “How could it not work or what could work about it?” One thing that I’ll throw out there that I experienced recently which was really such a simple thing and still was surprising to me, I had a friend that visited me for a week in New York recently and he is in the process of thinking about starting something new. We spent a lot of time during that week just talking for hours and hours. Just brainstorming ideas, thinking through things, talking big themes, the future. It was a really fun week. I really loved the guy. There was one idea that he-



Hiten Shah: I-



Steli Efti: Oh, go ahead.



Hiten Shah: I didn’t say anything.



Steli Efti: Oh. I don’t know. It was the ghost in the Skype universe. I thought I heard something. Anyways, to wrap this up, one of the ideas that he had, we kind of brainstormed and we both said, “Yeah, you should just work on this and you should do step one, two and three and gather a little bit more intel and a bit more data,” but there was one big glaring problem about how to execute this, how to scale this idea. The beginning of the week, we discussed that how could we solve the scalability issue, how could we address this. Eventually, he actually stopped me as I was ranting on different things and thinking really critically about it. He stopped me and he said, “You know what? Since we don’t have an obvious solution to this, who cares? I truly believe, if I start working on this and if we start seeing more data, more information, we’ll gather more insights that will then lead us to an answer to this problem. This scalability problem is not big enough for this idea not to be potentially, incredibly valuable, so let’s not worry about solving this now.” I was like, “Oh my God, he’s so right.” I wouldn’t have stopped though. I was in the framework of trying to solve this right now and I couldn’t, so I was stuck on that. Then, within four days of him doing some research, talking to some customers, interviewing some people and I was just observing this on the side while I was doing my own work, we had another discussion at a late dinner that then, boom, we instantly had a brilliant and simple solution to the scalability issue. I was like, “He was right.” Sometimes, you find the right solutions for the problem as you invest more and more time in it and as you learn more about it and you don’t have to solve all potential problems of an idea on day one or in the very early stages. That was kind of really beautiful for me to observe and be part of because I was kind of stuck on the different mind frame.



Hiten Shah: That’s pretty interesting. That’s very interesting. I think that this is just a super important topic for anybody listening because we’re either stuck because we don’t have any ideas and usually that’s because we’re stressed out and not great at feeling great or we’re ready to go and we have lots of ideas and when we communicate them to other people, I think there’s two important things here, we have to understand the person we’re communicating them to and we also have to understand ourselves to understand how should we be communicating this idea. Because often times, we can be really excited about a new idea and that excitement doesn’t always wear off on the other person to take it on by the other person and if you don’t know how that other person thinks, it’s much harder to communicate. For example, for me, I like communicating verbally. I think you do too.



Steli Efti: Yup.



Hiten Shah: With some people on my team, if I communicate the idea verbally, it’s not the most effective way to communicate the idea. The best way to communicate the idea is actually write it down or some kind of pictures of some kind of example. My worst fear is when I say an idea and someone asks me, “Who’s done it before? Show me.” The reason that’s my worst fear is I don’t know most of the time. These ideas aren’t something where I look somewhere else and came up with it. I was just thinking and I came up with an idea. I don’t know if someone else has done it.



Steli Efti: Yeah.



Hiten Shah: Quite frankly, I don’t care. Right? If it’s the right idea for us, it shouldn’t matter whether someone else has done it. In fact, if someone else has done it, it’s likely I might not want to do it anymore but that’s just my own impulse, right? I think it’s important to know how do you communicate, what’s your best way and also, what’s the best way to communicate an idea to the other person and force yourself to do it their way if you really need them to be onboard.



Steli Efti: Beautiful. All right. I think we’re going to wrap this episode up at this point. As always, if you want to get feedback from us, if you’re in the early days of ideas and you want to have two ears and eyes that are going to be friendly and brainstorm with you, just shoot us an email. If you’ve been super jaded and super cynical lately and you’ve kind of become a grumpy founder and want to talk about that, we always love to hear from you,, Until next time, we’ll hear you very soon.



Hiten Shah: See ya.