One of the biggest "startup rules" you always hear is that you should get your first customers organically, don't spend money on advertising at the beginning. We did the opposite. At Eprezto, we realized early on that when people needed car insurance, the first thing they did was search on Google. That was the moment of truth where they were most ready to buy. Instead of waiting to build traction through organic channels, we decided to invest in ads to capture that intent right away. A lot of people warned against it, but we knew our customer acquisition cost (CAC) was lower than our margin on each policy sold. That meant every dollar we spent on advertising was bringing in profitable customers. We reinvested that revenue back into ads, creating a flywheel that accelerated our growth far faster than we could have achieved by relying only on organic channels. The lesson: startup "rules" aren't laws. Question them. If you have a positive CAC, advertising isn't a waste, it's fuel for growth.
In the trades, there is one common "startup rule" that I saw broken, and it's the reason Achilles Roofing is successful. That rule is: you must always prioritize the lowest labor cost to win bids and scale fast. The local companies that succeeded broke that rule by paying top dollar and focusing only on local, master craftsmen. The flawed thinking is that a body is a body. We broke that rule by making a commitment to only hiring people who were committed to the craft. We pay our crews significantly more than the competition, and we give our best crew leaders a reliable salary even during the slow, rainy season. This is highly unconventional in an industry that relies on temporary, piecework labor. By breaking that rule, we eliminated the biggest financial risk in our business: mistakes and callbacks. A quality job is profitable because it doesn't leak and doesn't get bad reviews. Our dedication to higher labor costs means we only attract the best talent, and our quality control is practically self-managing because the crew takes pride in their higher pay and craftsmanship. The ultimate lesson is that the only sustainable growth engine for a service business is quality, not a low price. My advice is to break the rule that says you have to cut costs to succeed. Invest in your talent, stand by your prices, and let your superior craftsmanship be the reason you succeed.
Buffer succeeded by completely rejecting the conventional wisdom that salary information should be kept confidential - they published every employee's salary publicly online and built their entire culture around radical transparency. The traditional startup rule is to keep compensation private to avoid internal conflicts, competitive disadvantages, and awkward conversations with both employees and competitors. Most startups treat salary data as highly sensitive information that could damage morale or reveal strategic priorities to rivals. Buffer did the exact opposite. In 2013, they published a transparent salary formula showing exactly how they calculate every employee's compensation, then posted actual dollar amounts for each team member on their website. They also shared revenue numbers, user metrics, and internal decisions in real-time through their "Open" blog. This radical transparency became their competitive advantage rather than a liability. The approach attracted talent who valued authentic workplace culture over traditional corporate secrecy. Their openness generated massive media coverage and organic marketing that would have cost millions in traditional advertising. More importantly, transparency eliminated internal politics around compensation and created accountability that improved performance. When everyone knows what everyone else makes and why, it forces companies to develop fair, logical compensation systems rather than arbitrary decisions based on negotiation skills or favoritism. The strategic insight is that what feels risky or unconventional can become a differentiator when executed authentically. Buffer's transparency wasn't a marketing gimmick - it reflected genuine values that attracted like-minded employees and customers who trusted their commitment to openness. By breaking the secrecy rule, Buffer built a stronger culture, better talent acquisition, and more effective marketing than traditional approaches could have achieved, reaching $15M ARR without external investment.
Most startups are told to "move fast and break things." But one of the smartest founders I know did the opposite — he moved painfully slow. He spent a full year just talking to potential users before writing a single line of code. Everyone told him he was wasting time. But by the time he launched, he didn't need to pivot because his product fit like a glove. That company (Basecamp) ended up getting acquired within three years. While most startups chase hypergrowth, massive funding rounds, and "scale at all costs," Basecamp did the opposite: it stayed intentionally small, privately funded, and profitable from day one. Instead of building a bloated feature set or expanding into every possible market, they focused on doing one thing extremely well: helping teams communicate simply. By ignoring investor pressure and the Silicon Valley playbook, they built a company that valued autonomy, calm work, and long-term sustainability. In an era where "growth" often means burning through people and cash, Basecamp's restraint became its competitive edge.
One startup that proved you don't always have to "start small and niche" to win is Chewy, the online pet retailer. Conventional startup wisdom says "focus on one small product line first, validate, then expand." Instead, Chewy went all-in from day one-full catalog, 24/7 human customer support, handwritten pet birthday cards, even condolence flowers when pets passed away. They broke the rule of "stay lean and automated," and doubled down on high-touch service at scale. Everyone thought it was unsustainable-until pet parents became fiercely loyal and their repeat purchase rate sky-rocketed. That emotional moat helped them sell to PetSmart for $3.35 billion. The lesson? Sometimes going against the startup playbook is exactly what creates a category leader. You just have to pick the rule you're breaking for the sake of deep customer love-not ego. - Skandashree Bali
One that comes to mind is In-N-Out Burger. Most startups are advised to scale quickly, expand nationally, and pursue investors early. In-N-Out did the opposite. They grew slowly, stayed family-owned, and focused on perfecting operations in their existing markets before moving into new ones. By ignoring the "grow or die" mindset, they built a brand known for consistency and quality that's almost impossible to replicate. That lesson really stuck with me when building Green Home Pest Control. We chose to stay local and refine our service here in Arizona instead of rushing into other states. That slower growth has helped us maintain our high standards and keep our customers loyal—something that fast-scaling competitors often struggle to achieve.
Buffer is a perfect example--they broke the startup rule of building a complete product before testing demand by launching with just a landing page and two pricing buttons to gauge interest. When people clicked to buy, they got a 'coming soon' message, but Buffer learned everything they needed about market demand without writing a single line of code. I've used this same approach in real estate by testing interest in specific neighborhoods through simple direct mail campaigns before actually securing properties there--it's saved me from costly mistakes and helped me focus on areas where homeowners genuinely want to sell.
One great example is Airbnb. When the founders launched, every startup guide insisted on building fast, automating everything, and scaling early. But Airbnb broke that rule by doing the exact opposite. They personally photographed each host's home in New York City because the listings looked unappealing and were not getting bookings. Instead of chasing rapid growth, they focused on improving the experience for a few users until it was exceptional. That manual, hands-on approach something most investors called inefficient became the turning point for the company. Once people saw beautiful, trustworthy photos, bookings skyrocketed, and the model proved scalable. The lesson is that breaking a rule for the sake of quality can redefine an entire industry. Airbnb showed that innovation sometimes means slowing down and caring more about human connection than algorithms. In my own legal practice, I often apply that same mindset. By giving every client personal attention instead of automating everything, I build relationships that drive long-term success. True disruption begins when you are brave enough to ignore standard advice and follow what genuinely improves the customer experience.
Instagram broke the cardinal rule of launching with a comprehensive feature set - they stripped out almost everything from their original app Burbn except photo sharing and launched with just that core function. I've applied this same principle in real estate by focusing solely on cash offers for distressed properties rather than trying to be a full-service brokerage; sometimes stripping away complexity and doing one thing exceptionally well is exactly what the market needs.
Spanx broke the classic rule of 'validate your market first with extensive research.' Sara Blakely literally cut the feet off pantyhose with scissors and wore her prototype to Neiman Marcus without any market validation or focus groups. I respect that approach because in my wholesale real estate business, I've learned that sometimes you just have to trust your gut and execute - I closed my first deal based on instinct rather than extensive market analysis, and that momentum carried me forward.
I always think of Patagonia when it comes to breaking rules; they intentionally told customers, "Don't Buy This Jacket" in an ad campaign, totally defying the conventional marketing wisdom of 'always promote consumption.' It's a similar ethos to my real estate work, where instead of always pushing for a quick sale, I often advise clients on long-term wealth building--even if it means a smaller, slower payout--because building trust and genuine value ultimately creates a stronger, more sustainable business.
I think about WhatsApp, which completely ignored the rule that you need multiple revenue streams to build a sustainable business. They charged just $1 per year and focused entirely on creating the best messaging experience possible, refusing ads or other monetization tactics. As someone who transitioned from engineering to real estate, I've applied this same principle - instead of chasing every possible revenue stream in property investment, I focus exclusively on providing fair cash offers for distressed properties, and that singular focus has built more trust and referrals than any diversified approach ever could.
What stands out to me is Buc-ee's. It's not your typical "startup," but it completely broke the rule that convenience stores have to be small and fast. They built massive locations with spotless restrooms, a full kitchen, and an almost obsessive focus on customer experience. Most people thought it was overkill—why spend that much time and money on a gas station? That focus on quality over speed is what made them a Texas icon. It's a good reminder that breaking the "move fast and cut corners" rule can actually create long-term loyalty. In pest control, I've seen the same thing—slowing down to do the job right pays off way more than racing through appointments.
Warby Parker broke the conventional rule that eyewear had to be sold through traditional optical shops with high markups. They created a direct-to-consumer model with home try-on kits when everyone said people wouldn't buy glasses online. In my mobile home business, I've applied a similar principle by circumventing the traditional real estate model to work directly with manufactured homeowners--a segment largely ignored by mainstream agencies. Sometimes the biggest opportunities exist precisely where established players aren't looking.
I'd point to GoPro as a perfect example that broke the startup rule of 'don't enter hardware markets as a small player.' When Nick Woodman started making wearable cameras in his van, conventional wisdom said hardware startups needed massive capital and established supply chains to succeed. In my real estate business, I've applied this same contrarian thinking by purchasing properties that other investors avoid--like homes with major structural issues or complicated title situations. Going against the crowd has allowed me to find value where others see only problems, creating opportunities in segments of the market that traditional investors overlook.
I think about Slack--they broke the rule that a successful startup needs a brand-new idea by pivoting from a failed video game into a workplace chat tool. That pivot shows that listening to what people actually use and need can be more powerful than sticking to your original vision. I've applied that mindset in real estate by adjusting approaches when a traditional flip didn't make sense--sometimes turning a would-be flip into a rental or wholesale deal ends up being the smarter path forward.
One example that stands out to me is Ben & Jerry's, who broke the startup rule of 'focus narrowly' by embracing quirky, wild flavors and bold values from day one. Instead of playing it safe, they let personality and community lead their business--I've found a similar approach in real estate, where leaning into what genuinely matters to you, even if it bucks the norm, can connect you with clients in an authentic, lasting way.
Dollar Shave Club broke the rule that you needed a massive, expensive marketing campaign and retail presence to sell a commodity product. They built a brand on humor and a direct-to-consumer subscription model, focusing on convenience. That resonates with me because we also bypass the traditional, often inflated, marketing of real estate and focus on direct, honest communication to connect buyers and sellers efficiently.
A lot of aspiring founders think that success is a master of a single channel, like following rigid rules. But that's a huge mistake. A leader's job isn't to be a master of a single function. Their job is to be a master of the entire business. The startup that succeeded by breaking a common rule was a niche industrial supplier that broke the rule: "Thou Shalt Scale Marketing Channels First." The startup prioritized Operational Depth (Operations) over customer acquisition (Marketing). This taught me to learn the language of operations. The startup invested nearly all initial capital into building an iron-clad heavy duty quality control and fulfillment system, ensuring every OEM Cummins part delivered was perfect. They saw their quality system as their only marketing. Their slow initial acquisition was offset by unstoppable word-ofmouth. The success proved that the best pitch deck in the world is a failure if the operations team can't deliver on the promise. The best way to be a leader is to understand every part of the business. My advice is to stop thinking of a startup rule as a separate problem. You have to see it as a part of a larger, more complex system. The best leaders are the ones who can speak the language of operations and who can understand the entire business. That's a product that is positioned for success.
Airbnb succeeded by breaking the fundamental startup rule of 'create a scalable tech platform first.' When they struggled to gain traction, the founders literally went door-to-door in New York, taking professional photos of properties to replace amateur listings. I've seen similar success in my real estate business - sometimes you have to do the unglamorous, hands-on work before scaling. Their willingness to do things that don't scale created the foundation for what became a billion-dollar company.