Should I be a startup founder?

By Allen Yang

January 1, 1970

About this collection

Being a startup founder is appealing to some, but a hard path to go down. Tech culture today really celebrates and highlights founders, but is it right for everybody? Multiple founders describe the experience as "horrible," "chaotic," and mentally exhausting, with depression and suicide rates significantly higher among entrepreneurs. Yet the collection also illuminates why people persist: the unparalleled autonomy, creative fulfillment, and potential for massive impact. The most successful founders are driven not by wealth or prestige, but by a burning desire to solve a specific problem they deeply understand. Entrepreneurship isn't suitable for everybody - but could it be right for you? Ask away...

Curated Sources

7 Things No One Tells You About Being a Startup Founder - Ada Chen Rekhi

The article discusses the intense emotional challenges faced by startup founders, including the lack of structured days, feedback, and data to make decisions. Founders often experience impostor syndrome, intense highs and lows, and a deep tie between their identity and startup. The author shares personal experiences from founding Connected and highlights the difficulties of getting support due to the 'We are crushing it!' bravado in startup culture. The article also provides strategies to manage these challenges, such as expecting and normalizing the difficulties, building a support network, diversifying one's portfolio, focusing on the present, and celebrating wins.

Key Takeaways

Startup founders face unique emotional challenges that can be mitigated by expecting and normalizing these difficulties.
Building a genuine support network before needing it is crucial for founders to cope with the pressures of entrepreneurship.
Diversifying one's time and mental energy beyond the startup can help reduce the intensity of the challenges faced.
Focusing on daily accomplishments and celebrating small wins can help founders stay grounded and motivated.
The startup culture's emphasis on relentless optimism can make it difficult for founders to openly discuss their struggles and seek support.

What Startups Are Really Like

Paul Graham's essay analyzes responses from Y Combinator-funded startup founders about their surprising experiences. Founders highlighted key challenges such as carefully choosing cofounders, the all-consuming nature of startups, extreme emotional ups and downs, and the importance of persistence. Other surprises included the value of simplicity in initial product releases, engaging with users, being open to changing ideas, and the significant role of luck. The essay also touches on the difficulties of dealing with investors and the changing dynamics as startups grow.

Key Takeaways

The relationship between cofounders is crucial and can be likened to a marriage due to its intensity and the level of trust required.
Startups are all-consuming and require a different mindset than traditional employment, with persistence being a key determinant of success.
Engaging with users is vital, and being open to changing your initial idea based on user feedback is often necessary for success.
Dealing with investors can be challenging due to their lack of understanding of the startup's specifics and the significant role of luck in securing funding.
The startup journey changes significantly as the company grows, with founders needing to adapt from coding to managing and planning.

Good Product Manager, Bad Entrepreneur | by Emma Townley-Smith | Path to Product | Medium

The article discusses the challenges product managers face when transitioning to entrepreneurship, highlighting the need to shift from a product management mindset to an entrepreneurial one. It emphasizes the importance of user research, conviction in the process, and adopting a 'yes and' attitude to foster creativity. The author, Emma Townley-Smith, argues that product managers can make great entrepreneurs if they remember that the rules are the same for their product and others, they don't need to start with an idea, and they need to have conviction in the process and problem. The article is published in Path to Product, a publication offering insights for early and mid-career product managers.

Key Takeaways

Product managers need to overcome their tendency to fall in love with an idea and instead trust the product development process, starting with user research.
Conviction in the entrepreneurial process comes not just from having a great idea, but from working with a talented team or having deep knowledge of the user and problem space.
Effective product managers must shift from a hyper-critical mindset to a more open and creative 'yes and' attitude when developing new products.

4 Reasons Why Product Managers Make Good Entrepreneurs | by Jacob Burdis | Medium

The author, Jacob Burdis, shares his experience transitioning from a product manager at Pluralsight to founding Emmersion Learning, a bootstrapped startup. He highlights four key lessons learned as a product manager that have been invaluable in his entrepreneurial journey: (1) being open to being wrong and using user research to validate ideas, (2) deeply understanding the market through triangulation of qualitative and quantitative data, (3) embracing failure as a necessary step towards success, and (4) surrounding himself with people smarter than him to create a synergistic culture. These lessons have helped him navigate the challenges of entrepreneurship and find product/market fit.

Key Takeaways

The importance of humility and skepticism in entrepreneurship, recognizing that initial ideas may be wrong and require validation through customer research.
Triangulation of multiple data points is crucial for understanding the market and making informed decisions, rather than relying on a single data point or intuition.
Embracing failure as an inevitable and necessary step towards success, and striving to fail quickly and efficiently to iterate towards a better solution.
The value of interdependence and collaboration in entrepreneurship, recognizing that no single individual has all the necessary skills and expertise to succeed alone.

Do You Belong at a Start-Up?

The article 'Are You Suited for a Start-Up?' by Jeffrey Bussgang explores the key factors to consider when deciding to join a start-up. Bussgang, a venture capitalist with experience working for and investing in numerous start-ups, outlines the essential skills required to succeed in a start-up environment, including managing uncertainty, pushing limits, and thinking like an owner. He provides a framework for assessing one's fit for a start-up, choosing the right company, and positioning oneself for a successful application. The article emphasizes the importance of understanding the start-up's domain, stage, and potential for success, as well as the need to demonstrate value and a willingness to contribute to the company's growth.

Key Takeaways

To succeed in a start-up, one must be able to manage uncertainty, push limits, and think like an owner, requiring a unique blend of skills and mindset.
Choosing the right start-up involves considering factors such as domain, city, stage, and potential for success, with a focus on aligning personal passions and skills with the company's vision and needs.
Effective self-presentation is crucial when applying to a start-up, involving networking, demonstrating knowledge of the company, and showcasing one's ability to contribute to its growth and success.

Know the Costs of Being a Founder Before Taking the Plunge | Entrepreneur

The article discusses the challenges faced by startup founders beyond the well-known struggles such as fundraising and hiring. The author, Ryan Howard, shares his personal experiences as a founder of two companies that were successfully exited. He highlights the personal costs, isolation, and sacrifices that founders must make, including strained relationships and health issues. Howard also warns about people trying to take advantage of founders and provides strategies to mitigate these challenges, such as partnering with founder-centric investors and building a council of coaches and advisors.

Key Takeaways

Founders must be aware of the significant personal costs and sacrifices required to build a successful startup, including strained relationships and health issues.
The role of a founder can be incredibly isolating, with limited support systems and a high risk of depression and suicide.
To mitigate these challenges, founders should partner with founder-centric investors and build a council of experienced coaches and advisors to provide guidance and support.

I Asked 100 Founders, CEOs and VCs About Career Transitions — Here’s What I Learned

Sasha Orloff, former CEO of LendUp, shares his experiences and insights on career transitions, stepping down as a founder, and navigating post-startup life. After scaling LendUp for seven years, Orloff took a 100-day break and conducted 100 coffee chats with founders, CEOs, and investors to gain wisdom on career transitions. He discusses the challenges of transitioning from a founder to a CEO, the importance of self-scrutiny, and various pathways for founders after their first startup. The document also provides frameworks for thinking about future career opportunities and personal development.

Key Takeaways

Founders must assess their roles and responsibilities as their company grows, and consider stepping down if their skills no longer align with the company's needs.
Taking a break or sabbatical can be beneficial for founders to recharge and gain new perspectives.
Networking and seeking advice from others who have gone through similar transitions can provide valuable insights and support.
Founders have various career pathways to consider after their first startup, including becoming a repeat founder, investor, or executive at a large company or fast-growing startup.

I Don't Want to be a Founder and I Don't Think You Do Either | kipply's blog

The author reflects on their experience with a startup and YC Cohort, deciding not to become a founder. They argue that being a founder is not for everyone, highlighting the intense commitment required to cofounders, the risks and stresses involved, and the potential negative impact on one's sense of self. The author also challenges common reasons people want to become founders, such as the desire to own something, get rich, or have freedom to work on what they want, suggesting alternative ways to achieve these goals without the risks associated with starting a startup. The post is oriented towards technical founders in the Silicon Valley startup world and questions the glorification of the founder lifestyle.

Key Takeaways

The founder experience can be more intense and risky than commonly perceived, with significant personal and professional implications.
Alternative paths can provide similar benefits to being a founder, such as working on meaningful projects within a large company or as a side project.
The desire to become a founder is often driven by factors like ambition, desire for fame, or enjoyment of risk, which can be achieved through other means.

So you want to be a founder? Here’s where to start. | by Lily Chen | Journeys in Tech | Medium

The article discusses the journey of becoming a founder, highlighting the challenges and sacrifices involved. The author, a senior software engineer at Datadog, shares insights from an interview with Emna, founder and CEO of Veamly. The conversation emphasizes understanding the difficulties of being a founder, finding a problem you're passionate about solving, and taking risks. The author reflects on their own background and the motivations behind wanting to become a founder, drawing parallels between the challenges faced in academia and entrepreneurship. Key points include the importance of emotional stability, the need to be driven by a strong 'why', and the value of programs like Founder Institute for validating ideas and building a team.

Key Takeaways

Aspiring founders must first internalize the reasons not to be a founder, understanding the hardships and sacrifices involved.
Finding a problem you're passionate about solving is crucial for perseverance through the challenges of entrepreneurship.
Taking a risk, such as leaving a secure job, is a necessary step towards dedicating oneself fully to a startup idea.

The Hells of Being a Founder. Being a founder is horrible. There, I… | by Hampus Jakobsson | Thinking about Startups

The article 'The Hells of Being a Founder' by Hampus Jakobsson discusses the challenges faced by startup founders, describing the process as more art than science. It highlights the frustration of explaining a vision and the pressure to achieve product-market fit. The author shares personal experiences of founding two companies and the agony associated with it. The article provides six key lessons for founders: being honest with oneself about ambitions, focusing on one thing, building a strong team, managing investor relations, understanding the ways to fail, and daring greatly. It emphasizes the importance of having a clear vision, trusting others, and being open with the team and investors. The author also discusses the four ways a founder can fail: economic, health, bitterness, and becoming an unpleasant person. The article concludes with a quote from Theodore Roosevelt, encouraging founders to be in the arena and strive valiantly.

Key Takeaways

Founders must be honest with themselves about their ambitions and not be swayed by external hype, focusing on a clear vision that gives them energy.
Building a strong team is crucial, with co-founders and team members who can share the burden and provide constructive feedback.
Managing investor relations effectively by being transparent and making them part-time colleagues can help in getting the necessary support.
Understanding that failure is a part of the journey and distinguishing between personal failure and company failure is vital for maintaining mental and physical health.
Daring greatly and being in the arena, despite the challenges and criticisms, is essential for achieving success as a founder.

What Does it Take to be an Entrepreneur | Antler Academy

The article discusses the current state of the startup ecosystem, what it means to be an entrepreneur, and the critical skills and traits required for success. It highlights the importance of leadership qualities, team building, and adaptability in entrepreneurs. The author, Erik Jonsson, a partner at Antler, shares insights on the good, bad, and ugly aspects of launching a business and what investors look for in startup founders. The article emphasizes that being an entrepreneur requires a unique blend of skills, traits, and mindset, and that it's not for everyone. It also touches on the importance of having a clear vision, being willing to take calculated risks, and being prepared for the challenges that come with building a startup.

Key Takeaways

Entrepreneurs need to be adaptable and willing to learn from failure, as highlighted by Jessica Herrin's quote, 'You have to see failure as the beginning and the middle, but never entertain it as an end.'
The ability to build the right team and leadership qualities are crucial skills for successful entrepreneurs, as supported by HBR research.
Entrepreneurs must be prepared to manage the high risk, high pressure, and mental exhaustion that come with launching a business, and still maintain the motivation and commitment to drive their vision forward.
Investors look for founders who are flexible, passionate, and willing to take calculated risks, as exemplified by the marshmallow spaghetti tower game analogy.

Not Everybody Should Be A Founder

The article 'Not Everybody Should Be A Founder' outlines seven necessary characteristics and conditions that increase a person's chances of success as a startup founder. These include having minimal personal baggage, being self-sufficient, possessing personal leadership qualities, having relevant credentials, being able to immerse oneself in the startup, having analytical skills, and unique thinking with a clear vision. The author emphasizes that being a successful founder requires a combination of these traits and a well-planned strategy. The article is written by Ben Dyer, an Entrepreneur in Residence at Morris, Manning & Martin, LLP, and a partner at TechSquare Labs, who draws from his experience as a serial entrepreneur and technology advisor.

Key Takeaways

Successful startup founders must possess a unique combination of personal qualities, skills, and circumstances, including minimal personal baggage, self-sufficiency, leadership abilities, relevant credentials, and analytical skills.
Having a clear vision and a well-planned strategy is crucial for startup success, and founders must be able to immerse themselves in their venture and adapt to changing circumstances.
The article highlights that being a founder is not suitable for everyone and that it's essential to thoughtfully consider one's decision to start a business, taking into account their individual strengths, weaknesses, and circumstances.

The 5 Reasons You Should Become a Startup Founder – Pitching Angels

The article discusses the five reasons why someone should become a startup founder, as well as one reason that is often mistakenly considered a motivation. The five valid reasons are: having a love for adventure, enjoying wearing many hats, being in control of one's own destiny, wanting to use one's time productively, and having a burning need to solve a specific problem. The article emphasizes that becoming a billionaire is not a reliable or recommended reason to start a startup, as the vast majority of startups fail. The author, a startup mentor and investor, draws from their experience speaking with early-stage startup founders from diverse backgrounds and ages. The article highlights the challenges and responsibilities that come with being a startup founder, including the need to be adaptable, take risks, and make difficult decisions.

Key Takeaways

Startup founders need to be adaptable and enjoy wearing many hats, as they will be responsible for various aspects of the business.
Having a burning need to solve a specific problem is the most important reason to build a startup, as it drives the founder's mission and decision-making.
Becoming a startup founder is not a reliable path to becoming rich, as the vast majority of startups fail, and there are easier and more reliable ways to achieve financial success.

Why I don’t want to be a founder – Zara Zhang

The author, Zara Zhang, expresses her reluctance to become a startup founder, contrary to the prevailing trend in Silicon Valley. She argues that most people start companies for the wrong reasons, such as not wanting to work for someone else or seeking fame and fortune. Zhang believes that starting a successful startup requires a deep understanding of a specific problem, a unique solution, and a strong network of talented individuals. She also highlights the immense challenges and sacrifices that founders face, including long working hours, financial risks, and personal strain. Zhang cites the example of Eric Yuan, founder of Zoom, who had decades of experience in the collaboration software space before starting his company. She also references a Harvard Business Review study that found the average age of successful startup founders is 45, emphasizing the importance of work experience and industry knowledge. Zhang concludes that she is not ready to start her own company and prefers to work for others and learn from them for the next 5-10 years.

Key Takeaways

The motivations behind starting a startup are often misguided, with many founders driven by a desire for independence or prestige rather than a genuine need to solve a significant problem.
Building a successful startup requires a deep understanding of the industry, a strong network of contacts, and significant resources, making it a challenging and potentially unrewarding endeavor for many.
The lifestyle of a startup founder is often romanticized, but in reality, it involves immense stress, long working hours, and significant personal sacrifices.
The average age of successful startup founders is 45, highlighting the importance of work experience and industry knowledge in achieving success.
Rather than rushing to start a company, it may be more prudent to gain experience and build a network before embarking on an entrepreneurial venture.

Should you Start a Startup? 🚀 - by Luca Rossi

The author, an ex-VC-backed founder turned bootstrapped creator, shares his insights on whether one should start a startup. He emphasizes the importance of having the right idea, being an expert in the problem, and knowing how to build a solution. The author also discusses the pros and cons of VC funding versus bootstrapping, highlighting that VCs can accelerate growth but may not be necessary for all startups. He stresses that being a founder is an intense experience that requires managing one's energy and being prepared for the highs and lows. The article provides guidance on evaluating startup ideas, navigating funding options, and understanding the personal implications of being a founder.

Key Takeaways

To succeed as a founder, it's crucial to be an expert in the problem you're trying to solve and have the skills to build a solution, thereby mitigating market and execution risks.
The decision to seek VC funding should be based on whether it addresses a specific bottleneck that is hindering the growth of your startup, and whether you can clearly articulate how the funding will be used to drive growth.
Being a founder is an intense, all-consuming experience that requires careful consideration of one's personal and professional circumstances, as well as the ability to manage energy and cope with stress.

What We Look for in Founders

The document discusses the key qualities that Y Combinator looks for in startup founders. The author, Paul Graham, identifies five essential traits: determination, flexibility, imagination, naughtiness, and friendship. Determination is considered the most important quality, as founders need to be resilient in the face of obstacles. Flexibility is also crucial, as the startup world is unpredictable and requires adapting to changing circumstances. Imagination is valued over traditional intelligence, as it enables founders to come up with innovative ideas. Naughtiness, or a willingness to break rules, is also seen as a desirable trait. Finally, having a strong friendship between co-founders is essential, as it helps them navigate the challenges of starting a startup. The author provides examples of successful founders who embody these qualities, such as Bill Clerico and Rich Aberman of WePay, Daniel Gross of Greplin, and Emmett Shear and Justin Kan of Justin.tv.

Key Takeaways

The most successful startup founders possess a combination of determination, flexibility, and imagination, allowing them to navigate the challenges of entrepreneurship and come up with innovative ideas.
Y Combinator's approach to evaluating founders prioritizes qualities that are not typically measured by traditional intelligence or academic achievement.
The importance of friendship between co-founders cannot be overstated, as it provides a foundation for weathering the stresses and uncertainties of starting a startup.
The 'naughtiness' trait, or willingness to break rules, is a desirable quality in founders, as it enables them to challenge conventional wisdom and innovate.
The qualities that Y Combinator looks for in founders are not necessarily innate, but can be developed and refined over time through experience and practice.

Frequently Asked Questions

How do the 'seven things no one tells you about being a startup founder' from Ada Chen Rekhi's experience compare with the 'four ways to fail' outlined by Hampus Jakobsson, and what do these overlapping challenges reveal about the universal aspects of founder experience?
What specific evidence do these documents provide about the relationship between product management skills and entrepreneurial success, particularly regarding Emma Townley-Smith's argument that PM skills can be 'completely wrong for creating something from scratch'?
How do the investor perspectives from 'What We Look for in Founders' (determination, flexibility, imagination, naughtiness, friendship) align with or contradict the self-reported founder experiences of emotional volatility, isolation, and identity fusion described throughout the collection?
What patterns emerge when comparing the 'good reasons' to become a founder (burning need to solve problems, enjoying risk, wanting control) with the documented personal costs (health impacts, relationship sacrifices, financial uncertainty) across multiple founder accounts?
How do the different approaches to founder readiness—from the HBR systematic framework (pick domain, city, stage, winner) versus the more intuitive 'burning need' approach—reflect different philosophies about entrepreneurial preparation and success?
What connections exist between the emphasis on 'impostor syndrome' and 'completely justified Impostor Syndrome' in founder experiences and the investor focus on 'naughtiness' and rule-breaking as desirable founder traits?