7 Books & 3 Podcasts - That Helped Me Learn to Think Like a Founder

Over the past 18 months, I have undergone a gradual transformation from an education consultant to an EdTech founder. I used to see the issues I dealt with in terms of policy, programs, leadership or some combination of the three. We definitely need dedicated people working hard and thinking creatively in all of those fields, but I have come to feel that my own calling is in how to reimagine the power of technology to enhance education. The education system is constantly called on to do more with less and there is only so much policy and programs can do when resources are constrained. But doing more with less is exactly what technology is for. 

So I have immersed myself in the world of innovation and startup wisdom. 

I have not found any recipe or blueprint for becoming a founder or starting a technology company. Becoming a founder is not like learning a skill or set of processes. It’s more like learning a language. The only way to do it is through immersion. And while it’s important to study vocabulary, expressions, etc… learning a language only really becomes interesting when you’re able to combine these learnings in original ways and say something that is unique to who you are as an individual. 

My journey over these past 18 months has been incredibly rewarding. Each of the books and podcasts below has played a critical role in equipping me with the ideas and ways of thinking that have allowed me to speak and process the world through the lens of this new language. . 

7 Books 

Measure What Matters by John Doerr

This book is about Objectives & Key Results (OKRs). An objective is your big picture goal. Key Results are the measurable outcomes that, when achieved, will accomplish that objective. Using OKRs to organize the work of an organization helps to focus priorities, align work across team members, stretch the ambition of deliverables, and provide opportunities to track progress in a regular and systematic way. 

Seems pretty straightforward, right? I now use OKRs to organize the work of my business and even my personal life where I set KRs around things like playing music and traveling out of town to hit my objective of self-care. 

But maybe the biggest impact this book had on me is that I read it cover to cover, and it reminded me of the importance of actually reading a book all the way through. It’s easy to read the above paragraph and think ‘ok, I kind of get OKRs now’. But the book is almost 300 pages for a reason. There’s a lot of nuance in the application of these ideas. Because I had this realization with Measure What Matters I also read all of the books below start to finish. When you actually read a book (and not just a brief summary like I offer here) you not only get the big ideas, but also the limits of those ideas, which is ultimately much more interesting to think about when making actual decisions for a startup.

Lean Startup by Eric Ries 

Lean Startup is an incredibly practical book with concrete advice that essentially amounts to how and why we should use the scientific method to guide entrepreneurial ventures. When a startup is beginning we don’t actually know anything about how, or if, our ideas will work. All we have are hypotheses - hypotheses about a) the value of our product and b) about our strategies to scale our product. These hypotheses must be validated before they can be counted on. The implication here is that you should test and validate/invalidate as quickly as possible. This means giving people unfinished products just to test out assumptions about how they’ll be used and what value people will find in them. You then use these insights to inform future decisions. The quicker you learn, the better chance you have of being successful. 

I found these ideas liberating and in direct opposition to the systems I’d become used to in the public sector where it’s more about writing a grant to say exactly how you’ll do things for a year and then attach a logic model that looks like it’ll work. I now see that this approach is really just a bunch of hypotheses that were validated is some other context. If you’re working in the public sector, I highly suggest this book. You can even just flip to the part about ‘vanity metrics’ and then doing some deep soul searching. There’s also a bunch of super useful stuff in here about growth models and product development systems. Lean Startup really is an indispensable starting point for an aspiring entrepreneur. 

Zero to One by Peter Thiel 

This is a major intellectual work and a useful complement to Lean Startup. While Lean Startup kind of makes it sound like anyone can iterate themselves to a successful company just by responding to users, Zero to One reminds us that a founder actually needs to have a clearly defined vision of how the world will be better because of your product. 

Zero to One has also been fundamental in helping me appreciate the innovation imperative. As it points out early on, if everyone in India and China were to all of a sudden rise to the average American standard of living in today’s world, the result would be an environmental catastrophe. To create a more equitable and sustainable world for everyone, we need innovation in every sector of society. 

When I say that it’s also a major intellectual work I’m talking about how casually Karl Marx and John Rawls appear as foils for these kinds of arguments. There’s also how he goes out of his way to point out that capitalism and competitive markets are not nearly as closely related as most people think since, competitive markets slowly erase profit margins and capitalism depends on the accumulation of capital. 

I was also fortunate to read this book before actually knowing anything about Thiel’s politics. While I appreciate the first principles he begins with in this book, I disagree with him profoundly on the implications they have for the role of government and public institutions, which he has discussed elsewhere. 

Crossing the Chasm by Geoffrey A. Moore 

This book really blew my mind and made me realize that how I was trying to get word out about my product was really all wrong. It turns out building a market for a new technology product is a lot like building a fire. First you start with kindling, then small sticks, large sticks, and finally the logs that will sustain it in the long term. And it’s important to go in order. 

The kindling are the technologists. These are the people who geek out about anything new and are happy to use a buggy product. There aren’t many of them, but their buy-in is critical because you need them to get the attention of the small sticks or ‘early adopters’. These are the people who will bring a new product to their team because they always want to be on the cutting edge and see the potential of new technologies. Then there is a ‘chasm’ between these early adopters and the pragmatists who would really rather not disrupt their team with every new innovation. After the pragmatists, there are conservatives who only adopt new tech when they have no other choice and the skeptics who think new tech is just the agent of the devil. 

It turns out that you need to talk to each of these groups differently and it helps to go in order - deliberately courting tech enthusiasts first and then moving on to early adopters. How do you cross the chasm? Simple: you assemble a complete solution by putting your product in a larger context through partnerships and other strategies so that it can be adopted with minimal disruption by the pragmatists. 

Crossing the chasm is an amazingly useful guide for how to navigate each step of this process. It’s mostly about B2B marketing but has an appendix about B2C. I personally jolted up in my chair when I read the very last sentence of the book where he describes how in the future a combination of B2B and B2C will work together, “in a kind of pincer movement where grassroots movements will generate waves of mass adoption, and institutional marketing will find ways to invest and capitalize upon them… This pattern seems most likely to emerge in areas where public and private interests and funding intersect, such as healthcare, education, and public services, where both user and institutional behavior play seminal roles.” -- That is exactly what I’m working to do with Canopy in the education sector. So that felt validating. 

Range by David Epstein 

This is probably the most fun to read of the books on this list and the only one that's not actually a book about business. Range is about the power of diverse experiences to inspire innovation. It contains lots of stories about leaders in various fields who found innovative ways to solve problems - not through new technology, but because their experience allowed them to see how existing technology could be applied in innovative ways.

If, like me, you’ve jumped around to lots of different roles in life, and sometimes wondered if you should have just settled into a classic career track like your doctor and lawyer friends then, this book will feel empowering. Diverse experience means bringing a perspective that other people don’t have. The lessons from this book have eased my mind and stabilized my confidence as I transition from consultant to founder. I know that my range of unique experiences bring a valuable and important perspective to the world of education technology. My company may not be at the cutting edge of artificial intelligence, but I know how to apply more basic tech to improve the lives of teachers, students, and administrators in ways that they actually value. 

Blitzscaling by Reid Hoffman & Chris Ye

This book expanded the horizons of my ambition. It’s ok to grow big and to grow fast. Very big and very fast. The book is full of companies that went from dozens of employees to thousands of employees in just a couple years and to tens of thousands of employees a few years after that. 

Blitzscaling also provides a lot of guidance around the types of innovations necessary to support this kind of growth. Innovative practices relating to business models, strategy, and management are each broken down into defined categories and there are specific suggestions for the kind thinking in each of these categories that can actually scale successfully and why. Interestingly, there’s much less about actual technological innovation like AI or blockchain. 

Complex topics are broken down in a clear way that actually highlights what’s important about them. The section on the importance of gross margins made a particular impact on me. I used to feel strange about charging a lot more for something than it cost to create. But now I better understand that, that’s the only way you have the resources to make future investments and actually provide more value in the long term. (of course some companies, notably big pharma, can take this too far). While Canopy is still in the ‘family stage’ as described in this book it was still incredibly useful to make sure my startup has a scalable foundation. 

Traction by Gabriel Weinberg & Justin Mares 

Traction challenged me to think more broadly and creatively about strategies for getting people to learn about our product. In a lot of ways it’s about applying the Lean Startup ideas to marketing strategies where you develop hypotheses and run tests to see which channels will work the best for your product before investing/wasting too much money on a flawed approach.  

The book astutely points out that lack of traction is a more common cause of death for startups than lack of technology and that successful disruptors usually find workable tractions strategies that are different than the current leaders in their market. It also lays out a useful 50-50 rule for dividing time between product and traction at the beginning of a company. But the bulk of the book is just stories of company after company and descriptions of the innovative ideas they came up with to get their products off the ground. The ideas here can’t be ‘copied’ but the sheer range of them sparks the imagination. 

3 Podcasts 

Just as the books above should be read cover to cover, the key to the podcasts below is to NOT skim the titles of episodes to only pick the ones that sound relevant. Many of the most important lessons I’ve taken from these podcasts have been from episodes about companies or topics that seem completely irrelevant to me. As I mentioned with Range above, breadth of experience can be more useful than going deep into stories like your own.

The Pitch 

This is like Shark Tank but for actual venture backable businesses. It’s an entertaining show that also actually follows up after the pitch/offers to see what happened. More than any specific lessons about raising money, the exposure to multiple investors over all the various seasons and episodes amounts to a more thorough understanding of what gets investors excited and what gives them pause. It’s also just a lot of fun to learn about how many different types of interesting businesses and founder stories there are out there. For someone who doesn’t live in a startup hub, it has helped me feel connected to something larger happening in the world. 

Masters of Scale with Reid Hoffman 

The production value for Masters of Scale is at a whole other level compared to most business podcasts. There are stories, original music, and since it’s hosted by Reid Hoffman, the guests include the founders of the most successful companies in the world. Each episode is also organized around a central theme which creates a throughline across the stories in each episode and makes it easier to remember and internalize the insights that come up through the conversations. Pretty much every episode of this show has some content that made a direct impact on a decision I’ve made for Canopy or how I have thought about some aspect of the future. Whether it’s lessons on gamification from the DuoLingo episode, how to think about user experience from AirBnB, or strategies to take on bigger name competitors like Dropbox, this podcast has given me a lot to reflect on while also humanizing the individuals who actually put in the work to grow massively valuable companies. 

Traction with Jay Acunzo

There hasn’t been a new episode of Traction since 2017. I don’t know why they stopped. The last episodes were some of the best. This podcast was enormously valuable to me because it dug into the nitty gritty of early stage traction. Unlike Masters of Scale, most of the founders and companies here I had never heard of but, they all succeeded in creating and scaling something that had never existed before. Hearing these stories narrowed down to just the product-market fit and early growth phase of the company gave me insight into what pivots look and feel like and, again, emphasized for me just how many different paths there are to success. There are common themes across successful startups, but each path is unique to the nuances of the product, market, timing, and previous experience of the founders. 

This idea of when does conventional wisdom fit and when doesn’t it is also a question that weaves throughout the episodes of Traction. I liked that aspect of it. 

_____

It’s been a wild ride immersing myself in all of the content above over the past year as I also managed consulting clients and product development for Canopy. Being able to immediately process what I was learning through the lens of actual systems and decisions I was making with Canopy was incredibly useful. 

I’ve gotten to the point now where I think I’m starting to speak this language more fluently. I’m realizing that I may even have original ideas to express that may be able to add value to how all of this applies to education technology specifically and the public sector more broadly. 

If you have books that have been important to you in a similar journey, I’d love to chat with you about them in the comments! 

__

Honorable Mention 

Books

Hooked by Nir Eyal 

Want to know how to hook, trigger and reward users with features in your product to keep them coming back? This book will help 

Inspired by Marty Cagan 

A comprehensive guide for product managers that provides detailed guidance on pretty much every aspect of the job. 

Loonshots by Safi Bahcall 

Entertaining stories about innovation that echo a lot of the ideas from other books discussed above. 

The Alliance by Reid Hoffman, Ben Casnocha, & Chris Yeh 

Explains useful frameworks to think about hiring and team building in the modern age. Turns out it’s best to do away with the ceremony of pretending an employee wants to stay at the same company for decades and instead frame hiring as a short-term and mutually beneficial alliance. 

Podcasts 

SaaStr 

Range of tech heavy discussions relevant to SaaS Companies 

a16z

Again, pretty technical guests but it’s helped me be more fluent with some of the more modern topics in technology