Traditional management techniques for scaling startups are fundamentally flawed and detrimental to founder-led success. This post highlights Brian Chesky's experience at Airbnb, where following conventional wisdom led to disastrous results, prompting him to develop a new approach. This new approach, "founder mode," is characterized by closer engagement with the company, even at the detail level, and a willingness to break conventional norms.

Ken Kocienda saw Steve Jobs and Brian Chesky work up close and found that they had few key similarities. They both had deep intuition, a tireless work ethic, an unwavering commitment to their vision, and a fantastic ability to effectively guide and empower their teams. At the same time, they had differences such as Steve Jobs advocating for leaving smart people alone, while Chesky believed that founders needed to be more in contact with the “lower levels” of the company.

Bureaucrat mode is what happens when companies get big, scaled, and successful. People purposely implement best practices with good intentions, but these processes can make it hard to get anything done. Startups have a huge advantage over large companies in that they can move incredibly fast and just focus on output. As startups start to gain success and get bigger, they start to get bogged down with bureaucracy. This allows for newer, more nimble startups to emerge - then the cycle continues.

Triplebyte, a technical recruiting company, failed due to three main factors: it never solved candidate acquisition at scale, it pivoted to a product that didn't meet market needs, and it tried to change user behavior instead of catering to it. These challenges were made worse by the catch-22 of venture capital, where the need for funding to achieve viability often leads to pressure for aggressive, unsustainable growth.

Airbnb's migration from a monolithic Ruby on Rails architecture to a service-oriented architecture (SOA) in 2018 was driven by the need for improved maintainability and reduced single points of failure. The company outlined four key lessons learned during this transition: invest in shared infrastructure early, simplify service dependencies, centralize data hydration, and separate UI logic from backend logic. This article discusses the transition and compares Airbnb's architectural choices with those of other tech giants like Meta, Google, and Uber.

This article shares a tech co-founder's struggle with anxiety and burnout, which stemmed from the intense work environment in the startup world. Neglecting mental health can take a heavy toll. To manage his anxiety better, the author set boundaries and prioritized self-care.

This article shares a tech co-founder's struggle with anxiety and burnout, which stemmed from the intense work environment in the startup world. Neglecting mental health can take a heavy toll. To manage his anxiety better, the author set boundaries and prioritized self-care.

Zach Wilson, an ex-Airbnb staff data engineer, goes through seven tech interviews he failed over the last decade. He shares learnings from his time. For example, job hopping early in your career is great for growth, but not as great after you hit your mid-career.

Founder marketing is a crucial no-budget strategy where founders share their expertise and updates on personal social media. Regular LinkedIn posts on product updates, company milestones, and industry trends can build brand awareness effectively. Creative ideas like "Stealth Demo Drops" and "Contrarian Hot Takes" make posts engaging. Active audience engagement is essential for success.

This engineering manager learned three things from his time at Amazon: solve problems through mechanisms, communicate with precision, and give teams full autonomy. He misses the deep technical talks at Amazon but doesn't miss the inconsistent management culture before Andy Jassy's leadership changes.

In order to build value propositions that really resonate with your target customer segments, you need to understand what they are doing today (and why that method sucks). Airbnb's series of 8 commercials explain when and why it's the better choice for a particular group of people, for a particular subset of trips. This post includes a brief teardown of positioning and messaging for each of the 8 Airbnb commercials.

Founders should be wary of the VC ponzi scheme, where venture capitalists pressure startups to raise massive rounds at premature valuations, only to show paper gains to attract more funds from limited partners, which they take fees on. To avoid misaligned incentives, some firms opt for internal capital structures instead of traditional VC funds, ensuring they only profit from genuine investment success.

Y Combinator (YC) has established itself as a leading early-stage venture capital fund and accelerator, but its trajectory may be shifting due to a fundamental misunderstanding of what contributed to its initial success. The organization, under the leadership of Sam Altman, has opted to prioritize growth over the prestige that once defined its brand. This decision stems from a belief that accepting a larger number of startups would increase the chances of finding successful companies, despite the inherent risks of more failures. The rationale is rooted in the power law dynamics of venture capital, where a single successful investment can outweigh numerous losses. However, this approach overlooks the critical importance of reputation and exclusivity. Institutions like Harvard maintain their status by limiting admissions, understanding that their value lies in being selective. The allure of being associated with a prestigious institution is a significant factor for founders seeking investment. They are not just looking for financial backing; they want the legitimacy and status that comes with being part of an elite group. As YC expands its acceptance rates, it risks diluting its brand, making it less appealing to high-quality startups that once sought its endorsement. The implications of this shift are already visible in the current batch of YC-funded companies. For example, PearAI, a recent investment, has been criticized for merely replicating an existing open-source project. This situation raises concerns about YC's due diligence and commitment to fostering innovative ideas. The perception that YC is willing to fund any project, regardless of its originality or potential, undermines the exclusivity that once made being part of YC a coveted achievement. As YC continues down this path, it risks transforming from a prestigious incubator into a broad index of tech startups, losing its appeal to the most innovative and ambitious founders. The decline in its brand prestige could lead to a cycle where fewer high-quality companies apply, further diminishing its reputation. Once a brand loses its cool factor, regaining it becomes a formidable challenge, and YC may find itself at a crossroads where its past successes no longer guarantee future relevance.

Krithika Muthukumar, the very first marketer at OpenAI and Stripe, discusses what it takes to found and scale a marketing operation to build an enduring brand. A great early marketer doesn't blindly follow a playbook, is genuinely curious about the product, has a T-shaped skill set, and isn't distracted by vanity metrics. In their first month, they should create a “state of the funnel” report and shadow customer calls. Building a brand is often a bottoms-up motion rather than a top-down decision, so Muthukumar recommends developing a razor-sharp POV about what the product is for, learning how your audience talks and wants to be spoken to, and overinvesting in marketing craft.

Hacker News commenters detail various reasons why their startups failed. Some were too ambitious with their MVPs, while others tried to compete on price in a market that wasn't as price-sensitive as expected. Other people built something that people didn't want, while others hired people too early.

This blog post offers advice for founders of developer tool startups. Finding product-market fit should be the first priority for founders over building a complex product. Marketing efforts should be scrappy, and founders should try to maintain a work-life balance if possible to get through the hard times successfully.

Y Combinator (YC) has established itself as a leading early-stage venture capital fund and accelerator, but its trajectory may be shifting due to a fundamental misunderstanding of what contributed to its initial success. The organization, under the leadership of Sam Altman, has opted for growth over maintaining its prestigious reputation. This decision stems from a belief that accepting more startups would lead to greater financial returns, as the venture capital landscape operates on a power law where a few successful companies can offset numerous failures. However, this approach overlooks the critical role that reputation and exclusivity play in the success of venture capital firms. For instance, elite institutions like Harvard maintain their status by limiting admissions, understanding that their value lies in being selective. The allure of being associated with a prestigious brand is a significant factor for founders seeking investment. They are not just looking for mentorship; they want the legitimacy and status that comes with being backed by a top-tier VC. As funding becomes more accessible, the signaling power of that association diminishes, potentially harming the brand's value. The current state of YC reflects this decline in prestige. Recent funding decisions, such as backing PearAI—a project criticized for being a mere clone of another funded startup—illustrate a troubling trend. This situation raises concerns about the due diligence process at YC and suggests a willingness to fund projects without a thorough evaluation of their originality or potential. Such actions indicate that YC is moving away from its roots as an exclusive club for innovative startups, instead becoming a more generalized index of tech ventures. As YC continues down this path, it risks losing its appeal to the most innovative and sought-after companies. If the perception of YC shifts from a prestigious incubator to just another funding source, it may struggle to attract high-quality applicants, further eroding its brand and influence in the startup ecosystem. The challenge lies in balancing growth with the preservation of reputation, a task that, if mishandled, could lead to a significant decline in YC's standing in the industry.

Airplane, an internal tooling startup, was acquired by Airtable, who plans to shut down the product. Despite a healthy runway and happy customers, the acquisition was likely driven by the CEO's desire for a less stressful role rather than any fundamental problems with the company. Employees were given strong but not outstanding offers at Airtable with short deadlines and no severance if they declined. Ultimately, the outcome was disappointing to its employees, since the product was abandoned and strong customer relationships were damaged in the process.

Building venture-scale AI infrastructure startups is extremely difficult because startups lack the differentiation and capital needed to compete with established players like GCP, AWS, Vercel, Databricks, and Datadog, who are all striving to create end-to-end AI platforms. The open-source community quickly replicates any promising innovations, further eroding the competitive advantage of startups. To survive, startups must either focus on a very narrow niche, raise substantial VC funding, or remain bootstrapped.

Zach Wilson rapidly climbed the engineering ladder from Junior to Staff in five years through strategic job hopping from Meta to Netflix to Airbnb. He would build a strong internal brand by building trust and would communicate his impact well to get promoted quickly.

This article challenges three common engineering leadership anti-patterns. First, it argues against always avoiding micromanagement, suggesting that leaders should engage in "conflict mining" to understand context and write down the details of company strategies. Second, it advocates for measuring imperfect but useful metrics over waiting for perfect ones. Lastly, it challenges the idea of managers as umbrellas, suggesting that exposing teams to the "gory details" and providing less buffered information is probably better in the long run.

Purely Internet-based startups are approaching a saturation point. A new breed of startups that are willing to take on a lot more tech risk are starting to supplant the currently dominant species. The new startup era coming up will be heavier on technology and have longer incubation periods and likely higher capital intensity to fund ultra-specialized research that won't be easily commoditized. Investors will need to be more comfortable with tech slides and do more scientific due diligence.