How to Achieve Product-Market Fit and Empower Startups | Lindsay Tabas | Glasp Talk #27
This is the twenty-seventh session of Glasp Talk!
Glasp Talk delves deep into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today's guest is Lindsay Tabas, an Innovation Catalyst and digital storyteller, founder of LearnProductMarketFit.com, and host of the Make Sense podcast. With a rich background in engineering and technology from the University of Virginia and UC Berkeley, Lindsay has spent almost two decades working with pre-seed and seed startups, helping them achieve product-market fit. She has also mentored founders and evaluated startups on behalf of major VCs and accelerators, including Techstars.
In this interview, Lindsay discusses her journey from the early days of designing user interfaces to becoming a product-market fit expert. She explores how startups can identify valuable problems to solve, the importance of listening to customers, and how to iteratively build successful products. Lindsay also shares insights on the challenges of founding a startup, empowering founders to connect with their customers, and debunks common myths around visionary founders and product-market creation. Join us as Lindsay shares her expert advice on startup success, product innovation, and her unique approach to empowering entrepreneurs.
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Transcripts
Glasp: Welcome back to another episode of Glasp Talk. Today, we are excited to have Lindsay Tabas with us. Lindsay is an innovation catalyst and digital storyteller renowned for her work as a founder of LearnProductMarketFit.com and the host of the Make Sense Podcast. With a rich background in engineering and technology from the University of Virginia and UC Berkeley, she has spent over a decade in San Francisco and New York City. She has worn every hat, from understanding customer needs to guiding engineers in building the right products.
As a product-market expert, Lindsay has helped over 75 pre-seed and seed startups shape their visions into real products. She also mentors founders and evaluates startups on behalf of major VCs and accelerators like Techstars. Today, we will dive into her journey and insights on building successful startups, achieving product-market fit, and also the future of innovation. Thank you for joining us today!
Lindsay: Thank you so much for having me. That was a great introduction!
Glasp: Thank you! Yeah, so first of all, you've been learning and lecturing about product-market fit for over a decade. So, we want to know, what inspired you to start that, and also, was there any specific moment or event that triggered your decision to launch it?
Lindsay: No, interesting! Okay, so I want to start—I want to keep my journey simple. But, you know, I've been in tech. I designed my first user interface in 2002. It was human factors, human-computer interaction—everything about how technology enables humanity. That was what brought me into this industry and my career.
I spent the first 10 years working on teams at startups and enterprise software companies, wearing every hat between what the customers say and what the engineers build. I found that there were a lot of clashes when I insisted that we talk to our customers, that we talk to our users, that we design based on what they want—not based on what we want. There was a lot of friction and a lot of trouble for me to advocate on behalf of the human part of technology as a solution.
It was so bad and challenging that it actually made me feel like maybe I was wrong, and I was not cut out for the industry. Indeed, when I left San Francisco at the end of 2009, I had a tail between my legs, thinking I wasn't cut out for this industry.
The industry evolved a little more over the coming years. So, from 2005 to 2010, there wasn't a role for user experience designers. If you weren't a software developer, you weren't getting hired at a startup with 200 people or less. Like, you had to be a software developer. It evolved from 2010 to 2014. UX design became something people were looking for. I came back into the work world, excited, but the challenges were still there—the same challenges.
So, when I set out on my own, I was passionate about designing technology for people to support well-being and humanity. And that's not just lip service. That's not just marketing words. That's how I go about building and designing software and solutions. And I wanted to enable more founders to do that correctly, right? Most founders are all reading Lean Startup and Traction, and there are no step-by-step instructions in those books on how to talk to people and listen to what they say.
And there aren't step-by-step instructions in those books or any accelerator. You mentioned, like, I have experience with Techstars, both 2014 and 2022 and 2023. They don't have any content that is teaching founders how to say, "These are all the things I heard. These are the things that are worth paying attention to right now, and here's how we can go about designing features to meet those needs."
So, I set out to empower founders who want to solve real people's problems with the skills, tools, and resources to do that. And it just so happens that it's more lean and efficient and faster and cheaper if you listen to your customers rather than, you know, throw your ideas at the wall and build stuff, hoping something you put out there someone likes.
So, that's the origin story of Learn Product Market Fit—really just trying to help more founders orient towards their customers and their users.
Glasp: I see. And then you've helped, you know, I think around 100, you know, pre-seed and seed startups so far, right? And what is—you said, you know, the product—you know, you teach step-by-step product-market fit. What is the starting point? I mean, can you briefly share, you know, what you teach in the program or course?
Lindsay: Yeah! So, the first thing is that product-market fit is not an inflection point. It's often discussed as an inflection point like we will achieve product-market fit, and then we will do other things. Product-market fit, this idea that whatever you offer meets customer expectations, can be measured at every single stage of a startup's journey, okay?
At the earliest stages, you just have an idea. You have an idea for a solution. You have an idea of what that problem is. And we need to figure out what I call problem-value fit, right? What is the major problem you want to solve, and are there people willing to pay money to have that problem solved, okay?
So, the first two fits of my framework are founder-problems. So, why is this problem so exciting to you? And problem-value. Is there a real problem here, and are there people who will pay to have you solve it? And those two fits don't require any solutions or software or anything, because if there is a problem people want solved, and you tell them, "I'm thinking about solving this problem," they will talk to you. So, that's where you start.
Glasp: I see, yeah. I think for some developers, you know, that's—as a developer, you know, usually, you know, like, if the founders are developers, they dive into building a product and assume, having the assumption that, "Oh, maybe people want this." But, you know, it turns out, you know, later, like, three months later, they—it turns out, "Oh, this was wrong," and they spend a lot of time...
Lindsay: The number one reason startups fail is that they launched to no market need. That means that they built a product, and when they launched it, there were no customers for it, and they had to close because they ran out of money. So, they spent all their money building products based on their own ideas without validating the market before they launched. That's the number one reason startups fail—go to CB Insights, and they will tell you that.
And so, it's a natural human compulsion. Like, working on a solution is exciting. Sitting with a problem sucks. Like, there's so much anxiety around sitting with a problem. But there's this great quote from Albert Einstein: "It's not that I'm much smarter than you; I just spend more time with the problem," right?
So, if you sit with the problem that you're trying to solve, you often will find what I call the most valuable problem, the real MVP. It's this underlying problem that, if solved, will make all the little problems go away.
And then, you look for the customers that are so interested in solving that problem, feel the pain so much that they've tried all the other solutions, and they don't like all the other solutions out there. They're potentially trying to figure out a solution for themselves. They're hacking together something that works for them. That's who you find first, and that's kind of the first market that you need to find to match the problem to know that you're on the right track.
Glasp: Interesting! But how do you think or, like, how do you crystallize the problem so it's enough? So, yeah, to dive in, like, you know, how do you make the problem clear so that, you know, we can work on any framework or any techniques?
Lindsay: Yeah, sure. So, the best place to get started on a problem is probably Reddit. It's the most underrated market research tool. If you go to any of these subreddits that are focused on specific problem areas—there's plumbing, there's heating, there's pregnant women, there's so many different types of customer segments—you can explore. You can see it on Reddit. You can see it in Facebook groups. You see what people are talking about the most, right?
What are the problems people are asking about over and over and over again? Right? Then you look at what the solutions people are offering. And in the solutions, you see what's working for people and what's not working for people. If there are no—if there's no one on Reddit asking questions about this problem, this problem probably isn't that big of a deal, right?
So, that's the easiest place to start. But we don't want to just start there and then build a whole company off of that. We want to understand what these people are doing, thinking, and feeling when they experience the problem, and where they turn to first to find a solution. Because where they turn to first to find a solution is where we want to meet them when we eventually have a product to market to them.
There are so many things that we want to learn. So, we also want to pair that with interviews. So, the general structure that I advocate for and have resources for on LearnProductMarketFit.com is to do both the research of hanging out in these forums and then pair that with interviews so that you can validate your insights.
I think most founders jump to doing surveys, but surveys, while feeling easy, are far more complex and harder to do, and you're much more likely to get false positives and false negatives if you don't do the research—the qualitative research first—which is what I'm talking about in online forums and interviews.
Glasp: Yeah, yeah. That makes sense then. Yeah, yeah. As you mentioned, yeah, Reddit is, like, the most underrated, so, yeah, people tend to...
Lindsay: Yeah, it's the most underrated market research tool. I have an entire guide on how to use Reddit to do research observations.
Glasp: I see! And so, yeah, when you come up with, like, problems, so maybe you can find a solution, or, like, you know so if you have, like, you know, multiple solutions, like, how do you think, "So, this is the best solution to work on it"? Because, like, for one problem, there are many solutions, right?
Lindsay: Yeah, okay. So, this is—like, we're going to get kind of technical, but you have a ton of solutions to a single problem. At an early stage, a startup is like a Rubik's Cube because there’s the customer, there’s your skill set and your passions, there’s the problem, there’s whatever resources and money you have, and you’re twisting them in different directions to see what lines up, right?
So, the best idea for the first solution is to look at how people are solving the problem now and just make it a little bit better. So, an example that I like to use that’s pretty easy is let’s talk about people making beer in their garage in the ’90s. It was a very small community. People were DIY-ing their homebrew kits, looking at instructions from decades before to figure out how to build their own kit, right? And they were probably on different chat forums in the ’90s, trading with other hyper-obsessed, cult-like people on this issue.
Then it got really popular in the late ’90s and early 2000s, and there started to be a group of people that wanted to join this microbrew, homebrew community, but it was too much effort. It’s too much effort for them to figure it out on their own. So, someone says, "Oh, I’m going to take the best of the best of all of the DIY homebrew kits, and I’m going to package it in a way that makes it easier for the next group of people to join this movement, to join this circle," right?
So, if you find these early—what I call early evangelists—the ones that feel the problem so much, they’ve tried every solution, they’re building their solution because they haven’t found anything they like, but they’re willing to talk to you because maybe you can do it a little bit better. Your next step is to look at what they’re doing and make it a little bit better. That’s the easiest place to start on the solution set.
Glasp: I see! Does that make sense? That clears it up.
Lindsay: Makes sense, right? It’s different once the product evolves. Once the product evolves and you have clear customer personas, you’re going to have a primary persona and a secondary persona, and you’re going to look at what their actual needs are and then which features make both people happy, which features only make one user happy. But that’s once you really have a product that you can iterate on. To get to the first product, you just want to look at what people are doing for themselves and how you can make it a little bit better.
Glasp: Yeah, that totally makes sense. And then, at the same time, sometimes I see visionary founders build a market and create a market. Meaning I think, you know, such as, like, Snapchat or maybe, you know, B2C products like that. So, I think there are two kinds of approaches to product-market fit. One is, as you mentioned, the market gives you the product idea. Another is, like, a visionary founder’s vision creates the market, like Snapchat or, like, BD. Especially, we see these things in consumer products. What do you think about these two types of visionary founders? And also, as you mentioned, finding the product problem first, then looking for, you know, better solutions, iterating to find the better solution.
Lindsay: Yeah, so the visionary founder approach is not something that you can plan. You cannot follow a process. There’s no way to re-engineer how this person did the thing they did. They are not the norm, right? And it’s also kind of dangerous because it does fall under the creator entrepreneurial myth. People talk about Steve Jobs like this; people talk about Henry Ford like this. Neither of them just thought of an idea and built a market, okay?
The history books have it. Henry Ford was on the verge of closing after multiple times of prototypes not working, the runway running out, and not being able to get investors to fund him again—multiple times—before he had the Model T, right? Steve Jobs didn’t just, like, put his finger in the air and invent the iPod and the iPhone. These technologies existed at Xerox PARC. They existed in public and academic research. People were already listening to portable music; some MP3s already existed before the iPod, right?
So, it’s actually a myth, and I say it’s dangerous because our egos believe that we can be successful entrepreneurs—and we have to have egos; we have to be confident—but they also are scared to hear negative feedback and put their stuff out there. So, if we can come up with this really beautiful dream that I can be a visionary and change the way the world is going and make a market, my ego is going to buy into that, right? I’m going to buy into that, and instead of talking to any strangers, instead of doing any research or any validation at all, I’m going to sink $5,000, $10,000, $50,000, $150,000 into a prototype and put this out there.
And then, the number one reason startups fail is that there is no market need. So, that is why it is dangerous. You cannot re-engineer it. You cannot recreate it. It’s all based on luck. And this industry thrives on telling that story over and over and over again.
But take a step back—and now I’m going on a little detour because it’s something that makes me angry—virtual reality, metaverse. It’s all we talked about in 2022. We’re not talking about it anymore. Why? Because virtual reality still hasn’t found a major application for mass adoption, right? In 2004, I did a project on virtual reality. I coded in virtual reality modeling language, right? So, there are these stories that the industry tells that portray some person as a visionary for the metaverse, that they’re going to create some market. But this technology has been around for over 20 years, and it still hasn’t found mass adoption. You could say the same about blockchain and crypto—they still haven’t found mass adoption.
But we keep telling this story that we, can be visionaries who change the world. It’s dangerous. That’s—it’s dangerous. That’s how I feel about it.
Glasp: I see, yeah. Thank you for clarifying that. Yeah, yeah, really convincing. And by the way, I’m curious, how do you define product-market fit in that case? You know, you iterate ideas, and some people say retention models, or like Sean Ellis’ test says, you know, "If you ask 100 people and 40% say, ‘Oh, I’d be disappointed if I lost access to your product,’" or something like that. How is your program do you define product-market fit, and how do you teach it to people?
Lindsay: So, I go back again to product-market fit is not an inflection point, and it’s not something that we can wait to measure until the product is built and until customers are using it. So, retention models, and net promoter score—these are all things for products that already have customers, okay? We don’t have that at the early stages, and most companies who talk about product-market fit and are aiming for product-market fit don’t have that ability, right? They just don’t have the number of users to measure those scores.
So, my product-market framework, the innovation framework, has benchmarks for where you are in every stage—founder-problem, problem-value, value-prototype, prototype-pilot, pilot-growth, okay? So, at each stage and sophistication of your product, there is a different measure for what product-market fit means, okay?
So, if problem value is, "Hey, I have found these early evangelists that are so keen on me solving this problem that they’re willing to brainstorm with me, they’re willing to spend time with me, they’re not asking to get paid for a user interview because they are in—they want to solve this problem." So that’s your first kind of benchmark—problem value. Then value-prototype is your ability to provide value through whatever that first solution is. It might not be sticky, but you run it through user testing and usability testing, you’re able to talk about your value propositions, and people opt-in for your launch list or your newsletter because you’re able to connect with them emotionally about the problems they want to be solved and the aspirations they have for themselves.
You guys have a product out on the market. You know that understanding the emotions and aspirations and talking about problems—the marketing stuff that is so easy for engineers to dismiss—is probably the thing that will make or break your product’s success, right? So why not do it early before you sink tens of thousands of dollars into software development?
Can you launch—this is why a survey is important—By doing it later can you launch a survey? A survey is just like a landing page, right? You guys have a landing page; you want to get early opt-ins. You want to go to investors and say, "We have 2,000 people on our waitlist." What is a landing page? It’s a page full of value propositions convincing people to give you information, right? What is a survey? There are value propositions about a problem that needs to be solved, and you are collecting information for them.
So, if you can run a survey and hit—and I define this in the Labs program, Labs is the name of the program that’s up at LearnProductMarketFit.com—I define metrics of how many people you want to fit that early evangelist description versus how many people you want to take that survey so that you can have decent insights. But if you can’t convince more than 20% of your early evangelists, that tiny little group, to take your survey, then you’re still a little far off in conceptualizing what the problem and solution are, okay?
So, I’m not going to go through the entire framework. I do have a product-market fit ebook where I lay out the benchmarks for each of these innovation benchmarks, each of the kind of—how I define product-market fit at each of those stages. I’m happy to share that link. People can download the ebook. Everything is there. I want to share it. I do. I want to share this with everyone. So, go there to learn more about those different benchmarks.
Glasp: Thank you! By the way, I downloaded your ebook about Learn Product Market Fit, and it’s really helpful. And I think—we will put the link in the description.
Lindsay: You did like it?
Glasp: Yeah, I did like it, yeah.
Lindsay: Great! Thank you!
Glasp: Yeah, awesome! And I think you’ve seen many startups so far in your program and also outside the program. What is a trait or personality, or, you know, common things you find in people? I think, you know, some startups do well, some startups are not doing well. What have you found in successful teams or founders? What are the traits they have?
Lindsay: Yeah, there’s no, like, perfect makeup, right? There’s no perfect makeup. I think that certain things help someone be successful as an entrepreneur and founder. One, leaders are learners. So, just continuous learning and improvement. Like, if you just start every day admitting that you don’t know that much, and other people can tell you a lot more than you know, then that’s going to help you continue to look for opportunities to build your skills and not just your actual literal skills but your management skills.
I took workshops like that, and I have people who have worked for me for five or six years, never having been a manager full-time, because I opted into wanting to learn how to do it well. So, leaders are learners.
I like to go to something my dad always said to me, which was, "To be outstanding, you have to be willing to stand out." So, entrepreneurship, for sure, the fastest path to self-knowledge is being an entrepreneur because you have to continually do things that scare you. Standing out can be very scary. I find that a lot of founders have challenges with my framework about going to talk to users and putting surveys out there before they have a product because they want to hide behind their product, right? They’re too scared to put themselves out there and to do the marketing.
Again, marketing scares the crap out of most founders, so that’s why I challenge them to do it first because if they don’t have the guts to do it now, they’re not going to have the guts to do it later. And I’ve seen that.
And I think the other thing—and I have a video on YouTube where I talk about this—but the number one challenge for founders is focus. I actually have a little plate, and it says "Focus on Focus." I made it for my clients a couple of years ago for the holidays. It’s one of the New Year’s resolutions that changed things for me, like, in 2016: "Focus on Focus."
We hear so much feedback and insights from people, and we don’t know which ones to pay attention to. And then some of that feedback makes us feel very, very insecure, and then we think that maybe we’re wrong and need to change our entire plan. Then we start to take on too many projects and don’t have enough time to finish anything. We exasperate and exhaust all of our resources, and then the startup fails for something like the pivot gone bad, or they ran out of cash, or something like that.
So, I think the ability for someone to create a plan and as rigorously as possible stick to that plan is really helpful. To get there, you probably also need to have advisors, and they don’t have to be formal, but informal advisors that you can talk to and review your plans with will help you get past any confusion that’s leading you to not have any focus and be working on way too many things.
I worked for a startup once that raised, like, $30 million in a Series C round and then started closing down within six months because the CEO just had seven priorities that he wouldn’t make one more important than the other. And you can’t do that. You need to find your focus, and you need to prioritize.
Glasp: Yeah, focus and prioritization, that's key.
Lindsay: Yeah.
Glasp: Yeah, focus and prioritization—that’s key. Yeah. Thank you. I want that, like, you know, plaque or something. So, like, you give it for holidays to founders in your community, like “Focus on Focus.” It’s, like, you know—can I buy it? Can I get it?
Lindsay: You want one of these? Why not? Yeah! I love that suggestion. I’m putting more and more stuff on LearnProductMarketFit.com. What I’m doing right now is breaking up a lot of the guides and resources from Labs. So, Labs is the program on LearnProductMarketFit.com, in its original or latest form, it was a six-month program with 21 chapters, guides, templates, etc. For a whole other conversation, that program didn’t scale to growth. It kind of hit a point where it wasn’t, as a business, worth me running and scaling more.
But what I’m doing is breaking up all of the content into smaller bundles and putting them on the website so you can download just the resources around using Reddit for research, or just the resources around creating a really good survey to validate your problem and get feedback on your solutions, or just on onboarding new users—you know, the transition from when someone learns about your product to creating a user account. So, I have resources for each of those things, and I’m going to be putting them on the website. So, maybe I can put these on the website, too.
Glasp: Thank you! I hope—I wish it was a little cleaner so I could show it to you guys, but you can see, “Focus on Focus.”
Glasp: I can read it, yeah! Thank you, thank you. So yeah, by the way, you know a lot about product-market fit and have experienced so many things in product. So, I looked into your profile page, and it says you have experience being an entrepreneur or a founder. So, with so much information and knowledge you’ve gathered so far about product management, do you have any opportunity to start a startup again?
Lindsay: Are you asking me if I am going to start my startup?
Glasp: Yeah, why don’t you? Why don’t you start your startup again?
Lindsay: I love that! I love that question. It’s one of the things I learned about myself being an entrepreneur and self-employed for the last 11 years. So, I just said earlier that being an entrepreneur requires facing your fears and learning a lot about what you like and what you don’t like. I learned that I am not the type of person to run a product team.
So, I played every role: product manager, user researcher, UX designer. I’ve done some front-end engineering, and business analysis work—I’ve done all the roles on the product team. And I always was very stressed, like, once I was done with the designs, going through the sprint planning meetings and being there for software developers to support them, going through these iterations, and seeing some of my designs, like, morph and change—and not really for the better—and realize that, like, I don’t have the temperament for that. I don’t have the patience for that.
So, on a tactical level, my skill set—I’m an activator. I get people from zero to one. I’m probably the best person to think out the idea, do the research, and put the plans together, but I’m not the one who’s going to run with it. I’m going to give it to someone else to run with, right? So, one is temperament and skill set.
The other thing is that my passion—the problem I want to solve, my founder-problem fit—is enabling and empowering other people to do better in connecting with the human part of the problem that they’re solving. Everyone—not just engineers and technical people—everyone avoids the subjective, people part of a problem. Everyone wants to be like, "I have a problem, here’s the technology to solve it."
But we’ve been doing that for well over 20 years, and we can see a lot of places where that is not working, particularly people at their jobs. If you think about enterprise software at work, your CFO adds one more solution, your CTO adds one more solution, and it’s like, “This isn’t the thing that’s going to solve the problem,” because we’re not looking at the people side. The people side—people are subjective. We can’t predict them. We can’t make assumptions that they’re all going to act the same way all the time. They’re going to figure out the 1% edge case scenario that ruins the entire solution an engineer designed, right?
But that’s the key to success. That’s the key to lasting change. That’s the key to figuring out whether virtual reality has been worth the past 20 years of investment or not, is understanding the people part.
And in 2006, when I lived in San Francisco and was still in graduate school, I went to a panel with Mark Zuckerberg of Facebook and Reid Hoffman of LinkedIn. There was one other guy—he might have been from Myspace—but I don’t remember who it was. But I asked Mark Zuckerberg, “Hey, when are you going to hire social scientists because you’re changing the way that we communicate and connect?” Okay? And he dodged my question. Facebook didn’t go on to hire any social scientists until 2010, and by that point, the DNA of that company was set.
And how many problems has that company had with the people part, with the human part, over the past 15 years, 20 years? Right? It’s brought a lot of cool things, but it’s also gone off the rails in a lot of other places, too. You know? So, my passion is helping other people figure out the human, subjective part of problem-solving so that we can design the human experience for the future. That’s why I’m not starting, you know, another app.
Glasp: Awesome. Yeah, beautiful. And, by the way, I’m curious—after startups join your program, after the six-month program where you teach them things step-by-step, what usually happens to the startups? Do they raise money? Do they find product-market fit? What’s the usual path for them, and do you keep in touch with them?
Lindsay: Oh yeah, I do keep in touch with them. I think once I start cheering for someone, I won’t stop cheering for them. It’s very unique and specific to each one of them. I have some stats on my LinkedIn profile about the ones that went on to raise money, but not everyone building a tech startup wants to raise money, right?
My program has a lot of components that you need to think through to survive due diligence with an investor, but it is not specifically geared toward exiting the program and raising money. My whole philosophy is that if you have customers, raising money is easy. But if you don’t have customers, raising money is hard. So, I teach you how to have customers, right?
Of the founders that have gone on to raise—one of them just exited a few months ago. Unfortunately, some of them closed. Some of them have—I think the total raise—I really don’t keep track honestly—six and a half, seven and a half million, or so, more.
A lot of my founders—the most proud thing is, that the first version of that program was in 2017, and all of my founders' businesses from 2017 are still alive. So, that’s the proudest stat because I put a lot of weight on my flexibility and freedom. Like, I don’t want to work for anyone else. I don’t want to have to get approval to go to a dentist appointment. Like, I want to work on things that I want to work on.
So, if I can enable people not just to connect with their customers but to build the skill sets that keep them in business for a long time, for themselves, like, that makes me feel amazing. So, it really depends on who the founder is that has come out of the program. They might raise, they might hire software developers, they might continue to iterate on their prototypes, build something sustainable. Some of them learn that they don’t need to build technology to make the business that they want to make.
Glasp: That's interesting. And so, yeah, so awesome. And so, this is a little bit different topic, but, you know, we want to know about how you get knowledge and experience. You mentioned your journey and wearing so many hats, but how do you keep the information or experience? Do you use any note-taking apps? Do you keep a diary? How do you organize your knowledge and experience?
Lindsay: Oh! There are so many ways I could go with this question. I do use Evernote. I never really upgraded to Notion or anything like that, so I’ve been using Evernote for 12 years. That’s one area where I keep notes. When it comes to Dropbox and Google Drive, I use both. In 2016, I told you I’m a big proponent of continuous learning and improvement. I took a one-day seminar on managing multiple projects and priorities, and with that came some tips on organizing systems, and I did spend the time to kind of set that up.
So, I have pretty rigorous organizing systems on Google Drive, Dropbox, and my desktop to easily find the information that I need. Knowledge, I use Evernote primarily. One of the ways I use it is for email templates. So, if you are doing enough networking, as I’m sure you reached out to me, there’s kind of a template that you want to use over and over again. I use those. I have an archive of all different types of email templates that I want to use so I don’t have to ever recreate the wheel.
And then, I know you had a kind of similar question about ideas. Where I keep ideas is a separate conversation if you want to have that. There’s knowledge, and then there’s ideas. Knowledge—I just explained where I hold all of that.
Glasp: How about ideas? How about ideas?
Lindsay: So, one of my core strengths is ideation. My friends have called me a power generator of ideas. I am always thinking of ideas. I think of more ideas than I can keep up with. I cannot write them all down. And the challenge is, if I write some of them down, I start to look at them as items on my to-do list and not items that are just ideas to consider.
So, what I like to say is that if it’s a good idea, it will come up over and over and over again. And I’ll translate this to any entrepreneurs, any founders, any product managers. If you hear a user say something, and you’re like, “Oh, that’s a good idea,” one—you should wait until at least three other people say that idea before taking any action. So, it’s one person’s opinion. Two people say it, it’s a coincidence. Three people say it, it’s a theme.
Yeah, so if that idea is really that great, it will come up over and over again.
Recently, I launched a series of reaction videos to Silicon Valley (HBO). I’ve had that idea for, like, a decade. You know? I’ve had that idea for a long time and never knew where it fit in. But it kept coming up over and over again, and then this summer, someone brought something up and gave me some advice, and I was like, “Oh, now it’s time for that idea.”
All that being said is that I do have a folder on my desktop called "Ideas" that some things are in. Sometimes I realize I’m working on a project, and it’s not important, so I drag it into the "Ideas" folder. And sometimes, in companion to my active to-do list, I have a section that just says "Ideas." I rarely look at it. I really rarely look at it because I generate so many ideas all the time, I can’t keep up, and it becomes quite overwhelming to look at all my ideas.
Glasp: I see, yeah, that’s an interesting way to organize ideas, and yeah, and all your knowledge. And then, how about AI tools? Do you use any AI tools for, let’s say, brainstorming, ideation, or, as you mentioned, like, templates? You know, because nowadays, many people are using ChatGPT or other AI tools.
Lindsay: Oh, sure, sure, sure. So, like I said, I’m a big proponent of templates. I had a past intern ask me to write him a recommendation for graduate school. I just go to ChatGPT and ask for a template of what a recommendation letter looks like. I would never let ChatGPT write something for me, but it gives me a starting point. It’s the same as how I learn new things and how I figure out how to do new things. I usually go to the internet, I might go to ChatGPT now, but sometimes I also want to browse. But I look for people who have spelled out how they’ve gone about things so that I can create a process that I can follow for myself.
And so, I will go to ChatGPT and be like, “What are all the components of a great creative brief?” You know, and it will spit that out for me. I use ChatGPT and Google Gemini differently. I find Google Gemini gives a lot better feedback on writing. So, if I’m looking for suggestions on how to improve a LinkedIn post or article, or improve an email or bio, Gemini will reproduce and make it better, but it will also give you bullet points on what it did and why it did that so that you can improve as a writer. And I like that over ChatGPT because sometimes ChatGPT takes a lot more liberty with rewriting what I’ve said, and then the tone of voice is very different than my intentions.
I also use Grammarly, but I haven’t really gotten into AI image generation. I’ve found that every time I’ve gone to different tools to try to create stuff, it’s a lot harder. Like, the prompting is a lot harder than you would think it has to be to make it happen, or at least for what I’m looking for.
And then, I think, you know, AI is embedded in so many places. We can’t get away from it. So, I’m probably using it in a lot of other places that I have no idea that it’s even AI at that point.
Glasp: Yeah, so many—you know, AI is, like, you know, upcoming. And so, I’m just curious, like, how AI will change product management, product flows, or, like, finding or reaching product-market fit. Do you have any ideas on this?
Lindsay: Well, I just recently heard a good idea in terms of brainstorming problems and understanding problems. You can prompt ChatGPT to play the role of your target customer and then have a conversation with it. I think that’s really interesting because there are so many processes and frameworks within a startup’s journey—not just defining the original problem, but figuring out what the solution is, in marketing, in the voice of the customer, in all types of activities—you need to start with, “What is your customer’s problem?”
And every activity doesn’t require five months of research or even more than a day of research, right? And so, I like the idea of maybe being able to use an AI tool to talk to your customer and to create hypotheses about your customer that you go out and prove.
I have concerns because, as I said, plenty of people will cut corners when it comes to talking to actual people, and I am afraid that by doing that, they’ll think they’re doing research. But founders and innovators are already really bad at talking to customers and listening to other opinions, so to advise them to use ChatGPT as a way to avoid talking to real people, I feel is not in our best interest—not in the future’s best interest.
I have thoughts on AI in general. I call myself a pragmatic futurist because just because the technology exists doesn’t mean that it’s going to have mass adoption, doesn’t mean it’s going to have mass impact. Again, we’re still figuring out what to do with blockchain, still figuring out what to do with autonomous vehicles—they’re not quite safe just yet. Like, still figuring out what to do with virtual reality. We love—this industry loves to project all the crazy cool things that could happen, but the reality is that human behavior and adoption are the real defining elements of whether technology has an impact or not.
Specifically with AI, I think one of the biggest challenges in having an impact is the fact that in most places in our world—think healthcare, financial systems, government systems—the data is terrible. Like, the data is bad. So AI might help with small problems and small solutions, but there’s not enough electricity and power grids in the world to help a Fortune 500 company figure out what that 1970s COBOL system is doing that is supporting their entire business.
So, I think when it comes to solving really big problems, I don’t know that AI is going to have the massive impact that visionaries are predicting.
Glasp: That’s interesting, yeah.
Lindsay: Is that controversial?
Glasp: I like it! Yeah, thank you! So, yeah, and so this is kind of the second-last question. But, you know, thank you for sharing all the insights and knowledge with us. Do you have some advice for startup founders in pre-seed or seed rounds? You already shared so much advice, but is there something you’d like to leave us with?
Lindsay: Oh, I have so much, right? I have hundreds of videos on my YouTube channel. You can search playlists by market and customer research, product management, design, fundraising, or anything you want to know about startup founders. On the tactical, practical side, if you want to learn anything, I will point you in the right direction on YouTube.
I think what I said about leaders being learners, and “if you want to be outstanding, you have to be willing to stand out,” is huge. Having advisors so that you get out of your head. The other thing I mentioned I think is really important: A lot of founders think that fundraising will solve their problems, but it often creates more problems than they had originally. If you chase your customers and get customers, fundraising will be easier. But if you think that you can’t do any of that until you fundraise, you are going to create more problems for yourself.
And there are plenty of stories out there for you to learn about the problems that are created by fundraising when you’re not ready or when you don’t have a business that’s worth fundraising. All of it.
Glasp: I’m glad I got you laughing!
Lindsay: 100%! I find it really interesting—a tweet by Mike Michalowicz recently too—and he posted, "Our company has a problem: no product-market fit. So the only solution for us is to raise more money." In case we see some startups...
Glasp: Exactly. We see the same thing, yeah.
Lindsay: Right? Yeah, I mean, venture capital works for certain types of businesses, but I see a lot of—you know, I don’t think CB Insights will ever put on the top 20 reasons startups fail this reason, but like, prioritizing fundraising when they absolutely shouldn’t have—like, that’s how you run out of money!
Glasp: Yes. I think we should be watching this video again and again—like, 100 times!
Lindsay: I love that!
Glasp: With a plaque saying “Focus on Focus!”
Lindsay: For sure!
Glasp: Yeah, thank you for that. So, okay, this is the last question. And since Glasp is a platform where people can share what they’re reading and learning with others as their digital legacy, we want to ask you, what legacy or impact do you want to leave behind for future generations?
Lindsay: Yeah, so there are two things. One is going to be the fundamental orientation toward people and designing the human experience for the future. So, the more awareness and problem-solving—and I want to say, I say, like, elevate the way we innovate. Like, the way we solve problems in corporate America and in startups is still failing us. So, if I can help more people, particularly non-technical professionals, understand the landscape and empower them to thrive in our technical world, that’s a big thing.
The other thing, which is secondary, is just, like, I’d love to redefine what an engineer looks like. My passion isn’t specifically "women in STEM," but I don’t think that more women will go into STEM until there are more women like me who are willing to be visible, create content, and put their opinions out there.
So, that’s kind of the secondary legacy—taking up that avatar or persona in pop culture of what a woman engineer can be like. It doesn’t have to be nerdy or geeky or awkward. Hopefully, she can be a good conversationalist, make people laugh, and still share really important information.
Glasp: I see. That’s beautiful, yeah. Thank you. Thank you so much for all your insights and knowledge, sharing with us.
Lindsay: Of course. This was great! Thank you so much for having me.
