Smart Startups by Catalina Daniels Tried and True Advice from 18 Harvard Business School Founders

What's it about?
Smart Startups (2023) uncovers the strategies used to build major companies, direct from 18 Harvard Business School founders. This guide puts to rest the myth of the instant genius and easy investor wins. Instead, you’ll see how practical, even if unconventional, wisdom is needed to turn a great idea into a company that lasts.


If you think that starting a hugely successful company is all about being a genius and easily landing big investors early on, think again. This myth couldn’t be further from the truth, as authors Catalina Daniels and James H. Sherman discovered when they interviewed 18 founders.

But it wasn’t only the fact they’d all attended Harvard Business School that drove their success. In fact, it turned out they’d all unknowingly followed similar routes to their startup stardom – and that these routes are to a degree replicable. What’s more is that these founders often learned while doing – it wasn’t only their Harvard education that helped them crack the startup code.

This lesson unpacks these surprising lessons. In the following five sections, we’ll distill some of the key findings from the authors’ interviews with the 18 founders. From the ideation phase all the way through to scaling, you’ll learn how to walk down the trodden path of entrepreneurial success. We’ll pair theory with practice, showing plenty of real-life examples of how founders trekked the treacherous path toward huge valuations – and the often unconventional ways they got there.
It’s early 2012 – and Josh Hix and Nick Taranto are clocking in upwards of 60 hours a week trying to identify their first big business idea. They spend long days and nights pouring over spreadsheets, interviewing potential customers, and analyzing market sizes. Finally, after rejecting more than twenty ideas, they decide to pursue Plated, a meal kit delivery service. Within three years, the company will hit $100 million in revenue.

Josh and Nick’s path is, according to the authors, the embodiment of how smart startups are formed. Over the past decade, the authors identified two distinct patterns that lead founders towards successful entrepreneurship. And it’s not what you might expect. In fact, neither involve sudden flashes of inspiration – that’s only how startups are depicted in Hollywood.

The first of these patterns involves deliberate ideation. This group makes up about half of the founders that Harvard identified, Josh and Nick included. In this group, potential founders start off with no idea in mind, instead embarking on deliberate, methodical searches and analysis. Throughout the process, they evaluate various concepts against specific criteria, and often set timelines for when they’ll decide on one idea.

Let’s now meet Morgan Hermand-Waiche – he personified deliberate ideation all the way back in 2010. Similar to Josh and Nick, he was also a Harvard graduate in search of an idea. But he went at it alone, and ended up creating a list of 100 potential ideas. But it was lingerie that he went with in the end. Lingerie had initially entered his list at number 37 after his girlfriend complained about the high prices of established brands like Victoria’s Secret. He decided to pursue it after realizing that the $15 billion US lingerie market wasn’t making progress at resolving inefficiencies in its retail model. So, in 2011, he launched Adore Me – and by 2016, the company was generating more than $100 million dollars in revenue every year.

So, that’s deliberate ideation. But what about the second pattern the authors encountered? Meet organic ideation. Organic ideation involves founders whose ideas grew out of their own experiences over longer periods of time. In most cases, the ideas start small – but then grow ever clearer as they repeatedly come across the same problem.

One such problem was felt over and over again by Anthemos Georgiades. Between 2006 and 2011, he moved apartments a whopping seven times. And the same pain points accompanied wherever he went. He slowly came to realize that while finding apartments online was easy, actually nailing down the lease itself was far from smooth, involving countless viewings, mountains of paper applications, and seemingly endless days of waiting for responses. These frustrations finally morphed into Zumper, a platform where renters can sign leases online, no paper required.

It’s probably clear that both of these entrepreneurial approaches can yield impressive results. But it doesn’t matter how good your idea is if no one is willing to pay for it. That’s where the work of validation begins, which we’ll explore next.
When Josh and Nick settled upon their idea of founding Plated, to say they were just “excited” would have been a massive understatement. But the idea itself – even if forged after six months of deliberate analysis – would be worth nothing if they didn’t have proof that potential customers would actually pay for it.

So, Josh went about building a website – the front-end looked snazzy, but lurking behind was a bare-bones functionality that simply forwarded messages to his personal email. To drive some initial traffic to the site, they signed up for $10 of daily Facebook ads. Josh even personally manned the live chat for weeks! Then, after hundreds of conversations, the moment finally happened – someone entered their credit card. It was a beautiful moment, and one they’d been working toward for over six months.

It’s this sort of MVP-like validation process that the authors observed in all the 18 founders interviewed. The secret lies in keeping operations as simple as possible – but not sacrificing the customer-facing experience. The goal? To learn whether your customers are willing to buy into your concept before you go all in.

Let’s look at another example, one that really took “bare-bones” to the next level. Let’s meet HBS graduate Gil Addo, founder of RubiconMd. He’d spent years observing his grandmother’s healthcare struggles. But it was only after experiencing the power of telemedicine while in India that he began to connect the dots – could there be a better way to handle remote medical consultations in the US, too?

So, he went about validating his idea with a humble Google Form embedded in a website. The goal was to have American physicians submit questions that specialists could then answer remotely. This would eliminate time-consuming in-person referrals. The process at this point was quite manual. When doctors submitted their questions, Gil’s co-founder, Carlos Reines, would manually pass them on. As for the specialists, Carlos had found them by persistently visiting hospitals daily for six straight weeks, convincing doctors one by one to get on board. The funny thing is that most of this work was conducted from his laptop during HBS classes. It all worked out, though – their pilot proved that specialists could improve care plans more than 80 percent of the time and cut in-person referrals by nearly half.

While keeping operations simple is important, it’s perhaps equally important that founders themselves conduct all customer outreach at the initial stage. It’s their unique vision – and often sheer desperation – that can truly convince others to sign up to their idea. Delegating this process to employees is unlikely to carry the same weight. You’ve put in the time developing the idea. During validation, you need to stay the course. If you do so, you’ll be well-equipped to take your idea to the next level via growth. Let’s now turn to this stage.
Meet Matt Salzberg, founder of meal-kit service Blue Apron. In 2015, it achieved a valuation of more than $2 billion before its 2017 IPO. Back during its validation, Salzberg had a strong start – he was overwhelmed by user feedback, with people literally writing thousand-word emails describing how much his product changed their lives.

But he was soon overwhelmed by something far more serious. Six months into scaling, the company started missing deliveries. Suppliers began shipping the wrong ingredients. All the while, his team still managed their inventory with simple spreadsheets. The same simplicity that had enabled successful validation was now threatened to overwhelm the company entirely.

It’s here where the importance of mastering scaling becomes paramount. It’s a transition that can happen overnight – one minute you’re talking to early adopters, the next you’re getting thousands of orders and your systems crash. Indeed, it’s not an overstatement to say that this is probably the most treacherous part of the entrepreneurial journey. After all, the skill set needed for this phase is entirely different – where ideation and validation needed creativity, scaling requires operational excellence and facing tough decisions.

Take luxury fashion rental service Rent the Runway, for example. Nowadays, it exemplifies operational excellence, but it wasn’t always the case. Back when they started scaling, they initially tried keeping their operations lean by outsourcing tech to an external partner. They hadn’t done their homework, though – it turned out the partner was far from reliable. The result? Customers received the wrong products. Then, dresses started vanishing. It was only after their website crashed during their first big sale that they finally realized change was needed.

So, while placating angry customers, they started the difficult task of building an in-house operations platform. Their painful lesson was that anyone can rent out expensive dresses – but it takes a different sort of operation to form a competitive advantage. Theirs involved mastering reverse logistics as well as building up a huge dry-cleaning operation. On top of that came impeccable quality control – they even had employees smelling garments before shipping to ensure everything was just right. This comprehensive setup made it difficult for competitors to replicate their idea.

Together with strong operations comes the sometimes brutal process of scaling up your team itself, something many of the 18 founders struggled with. Anthony Soohoo of online furniture retailer Dot & Bo recounts the difficult decisions he faced while growing his team upwards of 50 people. This meant replacing early employees with more experienced ones who had a proven track record in handling scale. He even replaced his operations person who’d been with the company from the start. This is perhaps the hardest lesson when it comes to building a smart startup: loyalty to early team members can often destroy your company entirely.

There’s one thing you might be wondering at this point: how are all these experienced hires and fancy operational systems funded? It’s a great question – and one we’ll now explore in the next section.
It’s the classic question: what came first, the chicken or the egg? It’s a conundrum founders often face. After validation, do you go off in search of investors, or do you focus on acquiring capital? Surely the former necessitates the latter? Well, it turns out it’s a bit trickier than that.

Welcome to the interplay between scaling and fundraising. You might need funding to execute your offering, but investors often want to see results first. Indeed, the same investors who ignore you after validation might end up chasing you while you scale up – but only if you’ve proven your money-making capabilities. It’s precisely the operational victories we saw in the last section that make investors water at the mouth – they want to see that your idea can generate serious cash.

Let’s go back to Matt Salzberg of Blue Apron to see this play out in real time. Yes, he’d received raving reviews from customers during validation, but all VCs saw was an unproven meal-kit paired with rather complicated logistics. It was only two years later that they came back to him. In the meantime, he’d proved he could handle thousands of weekly deliveries, as well as learning from operational chaos along the way. The result? A $500 million valuation. Years later, it went public to the tune of $2 billion.

The HBS entrepreneurs discovered that timing mattered more than most founders realize. But that still begs the question: how do you go about breaking this seemingly circular dependency? It turns out the answer lies in finding creative ways to prove your execution capability without stocking up on huge amounts of venture funding.

Take Justin Joffe of Henry the Dentist. His idea initially failed to attract any funding for his mobile dental clinic, even after meeting with 75 VCs. So, he decided to take things into his own hands – and took out a personally-guaranteed SBA loan. Sure, it wasn’t much – but all he needed was to prove his idea could actually work. When he then approached Trail Mix Ventures, he finally had the numbers to back up his idea. They were all ears, and ended up as his first seed investor.

Once you have the proof of your idea's money-making capabilities, it’s important to not just accept money from any investor. The authors recommend locating smart money – investors who bring both capital and expertise to your venture. Dave Parker, for instance, paired the smartest funding sources with each stage of growth for Yumble Kids, his meal-kit company. While friends and family provided initial capital, it was a VC who had expansive knowledge of the food industry who he brought in for seed funding. And then, once he’d scaled sufficiently, he paired with Sonoma Brands to Series A – they brought in vital direct-to-consumer expertise.

So, to recap, we’ve gone through the three phases of ideation, validation, and scaling. Taken together, they probably seem like a surefire way to grow your company. But there are still a few other important things to remember that are less talked about. Let’s look at these next.
Before we wrap up, a quick word on three key qualities successful startups often embody. These are navigating external shocks, building an enviable company culture, and understanding good governance. As you’ll see, these all work together to create companies that can weather even the strongest storms.

Let’s start with external shocks, the bane of every founder. Greg Geronemus of smarTours wisely calls them “a constant stream,” and he’s not wrong. They’re a fact of life every founder inevitably faces. YouTube changes its algorithm. A key supplier goes bankrupt. Oh, and a once-in-a-century pandemic strikes. These are events you simply cannot control – and they all couldn’t care less about your business plan.

For many entrepreneurs, their gut instinct is to face these threats head-on, guns blazing. That’s what Geronemus did during the Ebola Pandemic, where he worked day and night to convince customers that South African safaris were still safe. After all, thousands of miles separated West and South Africa, but his American consumers weren’t buying it. Years later, he realized it would’ve been wiser to redirect his energy and pick winnable battles. Promoting safaris on other continents, for example.

It’s precisely this art of turning such "uncontrollables" into advantages that the 18 founders interviewed often mastered when the proverbial you-know-what hit the fan. For example, when Facebook decided to change their algorithm overnight, Planted’s Josh Hix decided to build internal paid media systems instead. This eventually became a core competitive advantage.

Moving on now to culture, the keystone of any successful company, startup or otherwise. And it’s precisely you as a founder who sets the cultural tone from day one. If you’re sending emails at midnight, you’re communicating unrealistic expectations. And if you promote jerks, your priorities are laid bare for everyone. Motivational posters may look nice, but it’s actions, not words, that set the cultural agenda at a company.

Finally, we reach the third quality – good governance. Think boards of directors, something most founders view as necessary evils imposed on them from investors above. But it’s the wisest founders who see boards for their true value – as sources of wisdom they can consult when times get tough. Matt Salzberg of Blue Apron appreciated this early on, and structured his board strategically. This involved maintaining control while also adding experts from diverse backgrounds. Turns out, it was on a board member’s recommendation that Matt set up the company’s unique logistics infrastructure, something that later became a key competitive advantage.

So, when you put these three qualities together, it probably comes as no surprise that they deeply interconnect. Think back to the Covid-19 pandemic – it was the companies with strong cultures that were able to adapt rather than panic. And good boards are always there to provide guidance when disaster strikes. Together, these three qualities embody the resilience that will help your venture stay the course when times get tough. And who knows – maybe that next disaster will lead you to developing that competitive advantage you so crave. Bon chance!
In this lesson to Smart Startups by Catalina Daniels and James H. Sherman, you’ve learned that smart founders follow replicable strategies of ideation, validation, scaling, funding, and finally, building true company resilience.

You've seen how smart entrepreneurs find their footing, whether through deliberate searching for an idea like the founders of Plated, or organically from personal experiences like Zumper. The next step? Validating that concept, this is often done with surprisingly lean methods, as demonstrated by RubiconMD.

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