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Smart Startups: What Every Entrepreneur Needs to Know―Advice from 18 Harvard Business School Founders – Real-World Strategies and Insider Insights for Scaling Successful Ventures
Two startup company founders and angel investors go inside eighteen companies founded by Harvard Business School graduates, uncovering surprising lessons for success and unexpected pitfalls essential for aspiring entrepreneurs. Conventional “wisdom” holds that the most successful entrepreneurs in the world are born with a genius for starting companies, experience one lightning-bolt moment of inspiration after another, follow a tried-and-true process to scale to a billion dollars, and attract deep-pocketed investors at every turn. The real story is a bit more unconventional—and much more interesting. Would-be-entrepreneurs Catalina Daniels and James Sherman, hungry to study and apply the best practices of startups to their own ventures, studied the nuts-and-bolts of entrepreneurship as classmates at Harvard Business School. Years later, after successfully founding and exiting several companies, and as angel investors in start-ups, they were surprised to realize that their experiences greatly differed from what they had been taught in school. HBS provided a world-class education in the basics. But there was so much they learned the hard way—working in the trenches—that, looking back, they wished they’d known before starting up. Inspired, Daniels and Sherman interviewed eighteen HBS graduates and entrepreneurs about their experiences founding companies such as Blue Apron, Rent the Runway, Gilt, and AdoreMe, probing them about what they discovered along the way and what they wish they had known beforehand. The authors bring these insights to life by showcasing the founders in their own words and giving readers the experience of chatting with these remarkable entrepreneurs over a cup of coffee. No other book has unearthed advice from so many HBS entrepreneurs. The result is wisdom that challenges assumptions, destroys preconceived notions, crystalizes hunches, and articulates perceptions with a depth possessed by few people in the world. Starting a business is hard. Seventy percent of startups today fail after their seed round, and less than ten percent achieve success for founders and investors. Faced with such a daunting threshold, aspiring entrepreneurs need all the advice, wisdom, and inspiration they can get. Smart Startups is written for them—a timeless record of essential knowledge that can help them avoid failure and achieve success.
- GenresBusinessNonfiction
384 pages, Hardcover
Published October 10, 2023
31 people are currently reading
1551 people want to read
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Displaying 1 - 11 of 11 reviews
February 4, 2024
I enjoyed Smart Startups. While reading, I had a flurry of business ideas and that was a fun aspect of this book!
I do wish it were a little more linear, rather than sometimes feeling like just a spattering of quotes, but for all intents and purposes, I felt like this definitely peaked my curiosity on aspects of starting a business and recommend for anyone curious about doing the same!
I do wish it were a little more linear, rather than sometimes feeling like just a spattering of quotes, but for all intents and purposes, I felt like this definitely peaked my curiosity on aspects of starting a business and recommend for anyone curious about doing the same!
March 12, 2025
I’m not sure how to rate this book. It had some great parts and some parts that droned on.
The opening chapters were most relevant to me. The first chapter was so captivating that I read it all before I walked over to the cashier and bought the book! The authors talked about how entrepreneurs actually come up with their business ideas. Real, intentional brainstorming effort is often required.
Beyond those opening chapters, the authors chose many surface-level topics to cover. I felt that this breadth held the book back. They covered too many topics with insufficient depth. If you’re very new to entrepreneurship, this book will probably teach you a lot.
The authors follow 10 or so Harvard Business School startups, including quotations from interviews with the companies founders. Sometimes these quotations add a nice piece of real-world input, while other times they aren’t given with sufficient context, and seem to add no value.
If you want to read this, pick it up at a library. There is some good input, especially if you’re new to entrepreneurship.
The opening chapters were most relevant to me. The first chapter was so captivating that I read it all before I walked over to the cashier and bought the book! The authors talked about how entrepreneurs actually come up with their business ideas. Real, intentional brainstorming effort is often required.
Beyond those opening chapters, the authors chose many surface-level topics to cover. I felt that this breadth held the book back. They covered too many topics with insufficient depth. If you’re very new to entrepreneurship, this book will probably teach you a lot.
The authors follow 10 or so Harvard Business School startups, including quotations from interviews with the companies founders. Sometimes these quotations add a nice piece of real-world input, while other times they aren’t given with sufficient context, and seem to add no value.
If you want to read this, pick it up at a library. There is some good input, especially if you’re new to entrepreneurship.
November 30, 2023
"It's like a playbook guide for anyone wanting to start up. The book is basically divided into 6 chapters, each representing a different stage of the startup journey. Every chapter covers the learning and thought process of the founder or team. Readers get an opportunity to learn from the successes and failures of 18 startups from various domains. I highly recommend this book for people at any stage of their startup. Consider it as an external consultant providing an unbiased outlook."
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July 4, 2025Starting a successful company is often romanticized as a moment of genius followed by swift investor interest, but "Smart Startups" by Catalina Daniels and James H. Sherman challenges that myth through the stories of 18 Harvard Business School alumni who each built thriving ventures. The book argues that while education plays a role, success is more often the result of consistent effort, intentional strategies, and learning through doing. Across interviews with these founders, common threads emerged — structured ideation, validating with minimal resources, scaling through chaos, raising funds at the right time, and building companies that can last. This book takes readers from the initial spark of an idea all the way to sustaining a resilient, high-growth company.
The journey usually begins not with a sudden flash of insight but with purposeful searching. Founders like Josh Hix and Nick Taranto of Plated exemplify 'deliberate ideation' — they put in long hours vetting numerous ideas through spreadsheets, interviews, and market research before landing on their final business model. Others, like Morgan Hermand-Waiche of Adore Me, followed a similar path by listing dozens of potential ideas and narrowing them down based on data and opportunity. Deliberate ideation is structured and logical, based more on analysis than intuition.
In contrast, some founders come to their ideas organically. These entrepreneurs encounter problems in their own lives, repeatedly, until the pattern becomes impossible to ignore. Anthemos Georgiades, for instance, dealt with multiple apartment moves over several years and consistently ran into the same problems with leasing. This eventually led him to create Zumper, a more streamlined way to rent apartments. These 'organic ideators' often experience their business ideas as gradual revelations rather than strategic selections.
Regardless of how the idea arises, the next step is validation — making sure that real customers are willing to pay for the product or service. Josh and Nick of Plated didn’t wait for the perfect platform before launching. Instead, they created a simple website and used Facebook ads to draw in traffic, testing their assumptions through direct customer interactions. The point wasn’t to have a fully built product but to test willingness to pay with minimal resources. This lean validation method allowed them to understand demand quickly and cheaply.
Another compelling example is Gil Addo of RubiconMD, who validated his telemedicine concept with only a Google Form and manual email routing. He and his co-founder personally collected doctor queries and responses, often working on it during business school classes. Their validation process was hands-on, scrappy, and immensely informative, ultimately showing that their product could improve healthcare outcomes while cutting costs. The key lesson here is that founders themselves must be intimately involved in early-stage customer engagement; no employee or consultant can substitute the energy and commitment of the visionary behind the idea.
Once a concept is validated, scaling becomes the next challenge — and often the most dangerous one. Founders go from managing a small, flexible team to trying to fulfill thousands of orders while keeping systems running. Matt Salzberg of Blue Apron experienced this firsthand. Despite strong customer feedback, his company quickly became overwhelmed by logistics problems. They were still running inventory off spreadsheets, which resulted in missed deliveries and wrong shipments. Scaling required not just fixing operations but completely rebuilding them.
Similarly, Rent the Runway struggled with operational complexity as they expanded. Initially, they outsourced tech development, only to find their external partner couldn’t meet expectations. Dresses began disappearing, customers received incorrect items, and the company had to bring everything in-house. What followed was a transformation — building out their reverse logistics, dry-cleaning systems, and quality control so well that it became a competitive advantage. Founders must shift from creative ideators to execution-driven operators to survive this phase.
Team dynamics also change dramatically during growth. Anthony Soohoo of Dot & Bo had to make painful personnel decisions as the company expanded, replacing early employees with more experienced hires who were better equipped to handle scale. This process is often emotionally difficult but necessary to maintain momentum. Loyalty is admirable, but clinging to early team members who aren’t fit for the next stage of growth can bring a startup down.
At this point in a startup’s journey, money becomes crucial. But the relationship between fundraising and execution isn’t linear. Many founders mistakenly believe they need large investments upfront. Instead, Daniels and Sherman show that strong execution often precedes funding. Investors want proof, not just passion. Blue Apron’s early struggles to raise money shifted once they demonstrated their operational capabilities. Only then did venture capitalists begin to take interest, eventually leading to a \$500 million valuation.
In some cases, founders bootstrap or take creative financial risks to get early traction. Justin Joffe of Henry the Dentist couldn’t secure funding from dozens of VCs, so he took out a personally guaranteed loan. That initial capital allowed him to prove the model, which later attracted serious investment. The lesson is that early proof points are more powerful than well-polished pitches. Once success is evident, founders can be more selective in choosing investors who offer both funding and strategic expertise — the so-called 'smart money.' Dave Parker of Yumble Kids chose investors at each stage who not only had capital but deep industry knowledge.
After funding, the final phase is building a company that can endure over time. That means learning to handle external shocks, cultivating a healthy internal culture, and establishing good governance practices. The book highlights Greg Geronemus of smarTours, who faced crises like Ebola and Covid-19 that dramatically affected his business. Instead of fighting losing battles, he learned to pivot and reallocate resources. Founders who adapt to change without panicking tend to build businesses that last.
Company culture, too, is set early and reflects the founder’s behavior more than their words. Leaders who work relentlessly without balance communicate unsustainable expectations, and those who tolerate toxic individuals implicitly endorse them. Culture becomes a feedback loop — if it’s broken, even strong operations can crumble under pressure.
Governance is often seen as a formality or an investor requirement, but the savviest founders use it as a strategic tool. Matt Salzberg, for example, used his board not just for oversight, but as a sounding board. A suggestion from a board member led to Blue Apron’s unique logistics model. Boards with relevant, diverse expertise can act as lifelines during crises and help founders make difficult but necessary decisions.
These final elements — resilience, culture, governance — all reinforce one another. During the Covid-19 pandemic, for instance, it was often the companies with strong internal cultures and wise external advisors that weathered the storm. Adversity exposed weaknesses in some startups, while pushing others to adapt and even strengthen their competitive positions.
"Smart Startups" makes a compelling case that startup success is less about luck and genius than it is about process, persistence, and adaptability. It lays out a replicable path — ideation (either deliberate or organic), lean validation, careful scaling, strategic fundraising, and a focus on long-term resilience. Through the stories of 18 Harvard Business School founders, Daniels and Sherman show that smart entrepreneurs don’t just dream — they build methodically, learn from failures, pivot quickly, and grow with purpose. This book doesn’t just celebrate success; it demystifies it, offering a practical guide for aspiring founders who are ready to work hard, think smart, and build something that lasts.
The journey usually begins not with a sudden flash of insight but with purposeful searching. Founders like Josh Hix and Nick Taranto of Plated exemplify 'deliberate ideation' — they put in long hours vetting numerous ideas through spreadsheets, interviews, and market research before landing on their final business model. Others, like Morgan Hermand-Waiche of Adore Me, followed a similar path by listing dozens of potential ideas and narrowing them down based on data and opportunity. Deliberate ideation is structured and logical, based more on analysis than intuition.
In contrast, some founders come to their ideas organically. These entrepreneurs encounter problems in their own lives, repeatedly, until the pattern becomes impossible to ignore. Anthemos Georgiades, for instance, dealt with multiple apartment moves over several years and consistently ran into the same problems with leasing. This eventually led him to create Zumper, a more streamlined way to rent apartments. These 'organic ideators' often experience their business ideas as gradual revelations rather than strategic selections.
Regardless of how the idea arises, the next step is validation — making sure that real customers are willing to pay for the product or service. Josh and Nick of Plated didn’t wait for the perfect platform before launching. Instead, they created a simple website and used Facebook ads to draw in traffic, testing their assumptions through direct customer interactions. The point wasn’t to have a fully built product but to test willingness to pay with minimal resources. This lean validation method allowed them to understand demand quickly and cheaply.
Another compelling example is Gil Addo of RubiconMD, who validated his telemedicine concept with only a Google Form and manual email routing. He and his co-founder personally collected doctor queries and responses, often working on it during business school classes. Their validation process was hands-on, scrappy, and immensely informative, ultimately showing that their product could improve healthcare outcomes while cutting costs. The key lesson here is that founders themselves must be intimately involved in early-stage customer engagement; no employee or consultant can substitute the energy and commitment of the visionary behind the idea.
Once a concept is validated, scaling becomes the next challenge — and often the most dangerous one. Founders go from managing a small, flexible team to trying to fulfill thousands of orders while keeping systems running. Matt Salzberg of Blue Apron experienced this firsthand. Despite strong customer feedback, his company quickly became overwhelmed by logistics problems. They were still running inventory off spreadsheets, which resulted in missed deliveries and wrong shipments. Scaling required not just fixing operations but completely rebuilding them.
Similarly, Rent the Runway struggled with operational complexity as they expanded. Initially, they outsourced tech development, only to find their external partner couldn’t meet expectations. Dresses began disappearing, customers received incorrect items, and the company had to bring everything in-house. What followed was a transformation — building out their reverse logistics, dry-cleaning systems, and quality control so well that it became a competitive advantage. Founders must shift from creative ideators to execution-driven operators to survive this phase.
Team dynamics also change dramatically during growth. Anthony Soohoo of Dot & Bo had to make painful personnel decisions as the company expanded, replacing early employees with more experienced hires who were better equipped to handle scale. This process is often emotionally difficult but necessary to maintain momentum. Loyalty is admirable, but clinging to early team members who aren’t fit for the next stage of growth can bring a startup down.
At this point in a startup’s journey, money becomes crucial. But the relationship between fundraising and execution isn’t linear. Many founders mistakenly believe they need large investments upfront. Instead, Daniels and Sherman show that strong execution often precedes funding. Investors want proof, not just passion. Blue Apron’s early struggles to raise money shifted once they demonstrated their operational capabilities. Only then did venture capitalists begin to take interest, eventually leading to a \$500 million valuation.
In some cases, founders bootstrap or take creative financial risks to get early traction. Justin Joffe of Henry the Dentist couldn’t secure funding from dozens of VCs, so he took out a personally guaranteed loan. That initial capital allowed him to prove the model, which later attracted serious investment. The lesson is that early proof points are more powerful than well-polished pitches. Once success is evident, founders can be more selective in choosing investors who offer both funding and strategic expertise — the so-called 'smart money.' Dave Parker of Yumble Kids chose investors at each stage who not only had capital but deep industry knowledge.
After funding, the final phase is building a company that can endure over time. That means learning to handle external shocks, cultivating a healthy internal culture, and establishing good governance practices. The book highlights Greg Geronemus of smarTours, who faced crises like Ebola and Covid-19 that dramatically affected his business. Instead of fighting losing battles, he learned to pivot and reallocate resources. Founders who adapt to change without panicking tend to build businesses that last.
Company culture, too, is set early and reflects the founder’s behavior more than their words. Leaders who work relentlessly without balance communicate unsustainable expectations, and those who tolerate toxic individuals implicitly endorse them. Culture becomes a feedback loop — if it’s broken, even strong operations can crumble under pressure.
Governance is often seen as a formality or an investor requirement, but the savviest founders use it as a strategic tool. Matt Salzberg, for example, used his board not just for oversight, but as a sounding board. A suggestion from a board member led to Blue Apron’s unique logistics model. Boards with relevant, diverse expertise can act as lifelines during crises and help founders make difficult but necessary decisions.
These final elements — resilience, culture, governance — all reinforce one another. During the Covid-19 pandemic, for instance, it was often the companies with strong internal cultures and wise external advisors that weathered the storm. Adversity exposed weaknesses in some startups, while pushing others to adapt and even strengthen their competitive positions.
"Smart Startups" makes a compelling case that startup success is less about luck and genius than it is about process, persistence, and adaptability. It lays out a replicable path — ideation (either deliberate or organic), lean validation, careful scaling, strategic fundraising, and a focus on long-term resilience. Through the stories of 18 Harvard Business School founders, Daniels and Sherman show that smart entrepreneurs don’t just dream — they build methodically, learn from failures, pivot quickly, and grow with purpose. This book doesn’t just celebrate success; it demystifies it, offering a practical guide for aspiring founders who are ready to work hard, think smart, and build something that lasts.
December 16, 2023
The authors took forever to get to the point. It's like they just wanted to put words on a page to distract readers (entrepreneurs) and waste their limited and valuable time. I read two chapters and still didn't get a single piece of advice. Wish they would have restructured it to share valuable insights first and then explain their source material.
February 6, 2024
Thanks to the authors and publisher for the giveaway.
This book is heavy on anecdotal stories. Some better, some worse. It all depends on where you are in the start up process on whether this book will be helpful. I did find some information that was helpful. Especially about MVPs. It makes sense in hindsight. Other information conflicted with other stories. What do you believe?
What I really learned from this book: it is not what you know but who you know. Just go to HBS and join the “fraternity” and have a long list of people to reach out to. This list is much much longer than the college or university you went to.
A more interesting concept would have been to cut half of the stories provided contrasted with HSB alumni who failed with the authors telling us why one succeeded over the other. My guess is some of the ones that failed took the same paths and did the same things that the successful did but with a different outcome. I think the end result is two fold: who had better connections and who just got lucky at the right place and the right time.
This book is heavy on anecdotal stories. Some better, some worse. It all depends on where you are in the start up process on whether this book will be helpful. I did find some information that was helpful. Especially about MVPs. It makes sense in hindsight. Other information conflicted with other stories. What do you believe?
What I really learned from this book: it is not what you know but who you know. Just go to HBS and join the “fraternity” and have a long list of people to reach out to. This list is much much longer than the college or university you went to.
A more interesting concept would have been to cut half of the stories provided contrasted with HSB alumni who failed with the authors telling us why one succeeded over the other. My guess is some of the ones that failed took the same paths and did the same things that the successful did but with a different outcome. I think the end result is two fold: who had better connections and who just got lucky at the right place and the right time.
December 28, 2023
Really well done startup book. Concise yet thorough, with first hand accounts and takes from 18 founders. For someone who loves podcasts, this was like an entire startup founder series crammed into 300 pages with commentary and synthesis. For fans of How I Built This, This Week in Startups, Masters of Scale et al this is right up your alley. It is also quite accessible for those new to learning about startups as it hits each part of the journey. It won't read as smoothly as just one founding story, but you'll get a lot more out of it, especially if you've already done a few of those.
The only downside, which is acknowledged by the authors as purposeful, is that the focus is on business model innovation vs tech innovation. Most of the lessons still apply to any startup, but it's worth noting as you go into this is you are a deep tech or hardware or some other more technical founder. The other noteworthy consideration is that many of the success stories have since been significantly repriced since going public (or broadly ended up exiting well below their peak). There is an element of the last cycle of venture capital (with 0% interest rates) at play that helped them grow that may not be available in the same capacity to the next generation of founders. This is addressed in part in the fundraising section, but again worth new founders considering what is possible today.
The only downside, which is acknowledged by the authors as purposeful, is that the focus is on business model innovation vs tech innovation. Most of the lessons still apply to any startup, but it's worth noting as you go into this is you are a deep tech or hardware or some other more technical founder. The other noteworthy consideration is that many of the success stories have since been significantly repriced since going public (or broadly ended up exiting well below their peak). There is an element of the last cycle of venture capital (with 0% interest rates) at play that helped them grow that may not be available in the same capacity to the next generation of founders. This is addressed in part in the fundraising section, but again worth new founders considering what is possible today.
January 9, 2024
Not groundbreaking but fun to read and a lot to learn!
July 29, 2024
Solid read for those interested in the startup space. The variety of outside voices from founders and ceo-types was the backbone of this book.
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October 19, 2025Blinkist
November 18, 2025
Packed with good fundamentals
Displaying 1 - 11 of 11 reviews