Jay’s Must-Listens: Want to Quit Your 9-5? 5 CEO’s Share the Exact Steps to Start Your Own Successful Business (No Business School Needed!)
In this episode of On Purpose with Jay Shetty, entrepreneurs discuss the steps to building a successful business. Shetty and his guests, including CEOs Emma Grede, Brian Chesky, and others, share insights on identifying market opportunities by solving real problems, building effective teams, and maintaining company values during growth phases.
The entrepreneurs explain how personal experiences can lead to business opportunities, as demonstrated by Suneera Madhani's discovery of gaps in payment processing and Good American's focus on underserved fashion demographics. They also address the evolution of leadership skills required for scaling companies, the role of perseverance in entrepreneurship, and the importance of learning from both successes and failures in business development.
This is a preview of the Shortform summary of the Jul 30, 2025 episode of the On Purpose with Jay Shetty
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1-Page Summary
Identifying and Solving Problems
Jay Shetty and Emma Grede emphasize that successful entrepreneurs focus on solving real problems rather than chasing viral success. Shetty advises finding a niche and building products that address genuine needs, while Grede suggests starting with problems you personally encounter. By targeting underserved audiences, like Good American's focus on women of color and plus-sized women, Grede demonstrates how addressing overlooked needs can build customer loyalty.
Both entrepreneurs stress the importance of diverse perspectives in problem-solving. Suneera Madhani shares how her family's problem-solving approach and her corporate experience led to identifying unique business opportunities, such as the payment processing gap she discovered between major firms.
Building the Right Team and Company Culture
Brian Chesky emphasizes the importance of founding a company with people you respect and trust, likening co-founders to parents who must maintain mutual respect above winning arguments. Emma Grede describes finding the right team members as "kissing a lot of frogs," highlighting the importance of shared values and vision.
Suneera Madhani discusses how establishing strong company DNA and core values helps navigate growth challenges. The speakers collectively emphasize creating a culture that encourages autonomy and collaborative decision-making rather than micromanagement.
Mindset, Skills, and Personal Growth For Entrepreneurs
Michael Rubin speaks about learning from near bankruptcies and failures, while Madhani discusses leaving comfort zones to pursue entrepreneurial ventures. Jay Shetty advocates for action over excessive preparation, encouraging entrepreneurs to create and evolve rather than waiting to feel ready.
Cody Sanchez advises learning from successful individuals in areas where you lack expertise, while Rubin recommends absorbing positive traits from respected figures. The entrepreneurs emphasize the importance of grit, with Sanchez referencing Angela Duckworth's research on perseverance as a key predictor of success.
Navigating the Entrepreneurial Journey From Start to Scale
When scaling from millions to billions in revenue, Madhani emphasizes the importance of adjusting strategies in terms of people, process, and profit. Cody Sanchez notes that leadership skills must evolve as companies grow, suggesting that not everyone can run a large-scale operation.
Emma Grede and Suneera Madhani stress maintaining core values during growth, while Brian Chesky describes how his focus has shifted from personal ambition to creating value for others. The speakers agree that while strategies and leadership must adapt during scaling, fundamental values should remain constant.
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Counterarguments
- While solving real problems is essential, some successful ventures have capitalized on trends or viral moments as a springboard for long-term success.
- Finding a niche is important, but entering larger markets with more competition can also lead to success if a company can differentiate itself and execute better than others.
- Personal experience is a great starting point, but entrepreneurs should also validate that their problems are shared by a large enough market to sustain a business.
- Targeting underserved audiences can indeed build loyalty, but it can also be challenging if the market size is too small or if the purchasing power is limited.
- Diverse perspectives enrich problem-solving, but they can also lead to conflict and indecision if not managed effectively.
- Relying on family problem-solving approaches may not always translate well to business contexts, which often require different strategies and expertise.
- Trust and respect are vital in co-founding teams, but some successful companies have been built by co-founders who had significant disagreements yet managed to work effectively together.
- While shared values and vision are important, too much homogeneity in a team can lead to groupthink, stifling innovation and critical thinking.
- Strong company DNA and core values are important, but they need to be flexible enough to adapt to changing market conditions and business phases.
- Encouraging autonomy and collaborative decision-making is beneficial, but there are situations where clear directives and strong leadership are necessary for efficiency and coherence.
- Learning from failures is important, but an overemphasis on past failures can lead to risk aversion and missed opportunities.
- Action is important, but insufficient preparation can lead to avoidable mistakes and business failures.
- Learning from others is useful, but over-reliance on external advice can prevent entrepreneurs from developing their own unique strategies and insights.
- Grit and perseverance are important, but so is the ability to pivot or quit when evidence suggests that the current path is not viable.
- Adjusting strategies for scaling is crucial, but some businesses may succeed by maintaining a consistent strategy and focusing on incremental improvements.
- Evolving leadership skills are necessary, but some leaders may excel in both small and large-scale operations by leveraging their unique strengths and adapting their style.
- Maintaining core values is important, but sometimes values need to evolve as the company grows and the external environment changes.
- Shifting focus from personal ambition to creating value for others is noble, but personal ambition can also be a powerful motivator for innovation and business growth.
- Fundamental values should remain constant, but they may need to be reinterpreted or expanded upon to stay relevant as the company scales.
Actionables
- You can start a "problem journal" to identify everyday challenges and brainstorm solutions. Keep a small notebook or digital document where you jot down any inconvenience or problem you encounter throughout your day. At the end of each week, review your entries and think about simple, feasible solutions that could address these issues. For example, if you consistently forget to water your plants, you might think of setting up a low-tech reminder system using household items.
- Develop a "value-first" mindset by volunteering in a community that aligns with your interests. This will help you understand the needs of a specific group and how you can create value for them. For instance, if you're passionate about elderly care, volunteer at a senior center and observe the daily challenges they face. You might come up with a service idea like a mobile app that connects seniors with local volunteers for companionship and errands.
- Create a "grit grid" to track and develop your perseverance in the face of challenges. On a grid or spreadsheet, list down ongoing projects or goals in one column and the obstacles you face in another. Next to each obstacle, write down actionable steps you can take to overcome them and a deadline for when you'll tackle these steps. This could be as simple as dedicating 30 minutes each day to learning a new skill that's been difficult for you, like public speaking or coding basics.
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Identifying and Solving Problems
Entrepreneurs who focus on solving real, impactful problems tend to build successful businesses that inspire loyalty and deliver value.
Successful Entrepreneurs Solve Real Problems That Impact Lives
Jay Shetty and Emma Grede stress the importance of creating businesses based on real needs, emphasizing a shift away from the allure of viral success and towards tangible solutions.
Identify Problems Faced by You or Your Target Audience, Rather Than Solving Abstract Problems
Shetty advises aspiring entrepreneurs to avoid being preoccupied with growing an online presence or achieving fast scale. Instead, he suggests finding a niche and building products that address real, unmet needs. Starting with a problem one personally encounters offers a genuine starting point, an approach underscored by Emma Grede. She believes that if something is a problem for her, it's likely an issue for others like her, which is crucial in identifying new business opportunities.
Design For Diverse and Underserved Audiences to Build Loyalty
Underserved audiences are key to building business stability. Grede’s brand, Good American, targets women of color and plus-sized women, patrons often ignored by the fashion industry. By focusing on these groups and recognizing their value, Grede built her company and, in turn, cultivated a loyal customer base that feels acknowledged.
Include Diverse Voices for Better Solutions
Both Shetty and Grede emphasize the need for diversity in business problem-solving. Having varied perspectives at the decision-making table leads to better business outcomes and helps avoid insensitive mistakes, Grede highlights. It's crucial, she notes, to integrate inclusivity and diversity from the outset of product development, ensuring that an array of customer needs is reflected and addressed in company innovations.
Sanchez, discussing her observations in local businesses, sees potential for improvements a ...
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Identifying and Solving Problems
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Counterarguments
- While focusing on real problems can lead to successful businesses, some businesses thrive by creating demand for new products or services that consumers were not previously aware they needed.
- The emphasis on solving problems personally encountered may not always translate to a broader market need, potentially limiting the scope of the business.
- Rapid scaling and online presence are sometimes necessary for certain business models and can be beneficial if managed effectively alongside solving real problems.
- Targeting underserved audiences is valuable, but businesses must also ensure they have the resources and knowledge to serve these markets effectively without tokenism or stereotyping.
- Diversity in decision-making is crucial, but it must be accompanied by a culture that genuinely respects and acts on the input from diverse voices, rather than just including them as a formality.
- While inclusivity and diversity are important, they must be balanced with a clear vision and strategy to prevent a dilution of the brand or product focus.
- Established businesses may have space for problem-solving, but they also face challenges in agility and innovation due to existin ...
Actionables
- You can identify underserved markets by keeping a journal of your daily frustrations and the frustrations of those in your community. Note down any moments where you or someone you know expresses dissatisfaction with a product or service. After a month, review your entries to spot patterns and potential market gaps that align with the experiences of diverse groups.
- Develop a habit of asking five "why" questions whenever you encounter a problem to uncover its root cause. This technique, known as the "5 Whys," helps you dig deeper into issues you face personally, which could be indicative of broader market needs. For instance, if you're frustrated with a piece of kitchen equipment, ask "why" repeatedly to understand the underlying issue, which might lead to an innovative product idea.
- Create a feedback circle with ...
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Building the Right Team and Company Culture
Recognizing the crucial role of team composition and culture, speakers Brian Chesky, Rubin, and Suneera Madhani explore how to cultivate the right environment for a company's success.
Build a Team With Complementary Skills and Shared Values For Success
The importance of assembling a team that shares a company's core values and complements each other's skills is echoed by the speakers.
Prioritize Respect and Trust Over Skills When Choosing Co-founders and Employees
Brian Chesky and Rubin emphasize the profound impact of fostering relationships founded on respect and trust within a company's leadership and workforce. Chesky believes starting a company with friends—or at least with people one can envision as friends—is invaluable due to the deep respect and love necessary for the extensive time co-founders spend together. Similarly, Rubin highlights the need to surround oneself with people who are not only talented but also passionate about improving their work.
Grede also touches upon the essential nature of finding individuals who understand and share her vision, likening the recruitment process to "kissing a lot of frogs" in search of the right fit. This analogy underscores the necessity of compatibility and shared values when building a team or seeking partners.
Foster a Collaborative Culture Based On Core Values to Navigate Challenges and Maintain Momentum
Chesky uses the analogy of founders being like parents of a child, suggesting that mutual love and respect among founders set a positive tone for the entire company culture. He recounts a decision made with his co-founders to place their relationship above any single decision within the company, valuing mutual respect over winning arguments.
Likewise, Madhani reflects on the establishment of ...
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Building the Right Team and Company Culture
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Counterarguments
- While complementary skills and shared values are important, too much homogeneity can lead to groupthink, stifling innovation and critical thinking.
- Respect and trust are vital, but they should not completely overshadow skills and expertise; a balance is necessary to ensure the team is competent and capable.
- A collaborative culture is beneficial, but there must also be clear leadership and decision-making authority to av ...
Actionables
- Create a personal values statement to guide your interactions and decisions. Write down your core values and use them as a benchmark when collaborating with others. For example, if one of your values is transparency, actively practice open communication in group settings and encourage others to share their thoughts and concerns.
- Start a 'no-blame' feedback session with your peers or colleagues. During these sessions, focus on discussing challenges and solutions without pointing fingers. This can be done in a casual setting, like a coffee meet-up, where everyone is encouraged to share their insights on how to improve collaboration and trust within the team.
- Implement a 'decision day' where you and your team dedicate time to coll ...
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Mindset, Skills, and Personal Growth For Entrepreneurs
Michael Rubin, Jay Shetty, Suneera Madhani, and others contribute their insights on the essential mindset, skills, and approaches necessary for entrepreneurs’ personal growth and success in a rapidly evolving business landscape.
Cultivate a Learning, Risk-Taking, Perseverant Entrepreneurial Mindset
Experts in the entrepreneurial field emphasize the importance of continuously learning, embracing failure, and demonstrating grit and passion as key components of entrepreneurial success.
Embrace Failure to Learn and Improve
Embracing failure is a significant theme among entrepreneurs, as highlighted by their own experiences and perspectives on risk-taking. Rubin speaks from personal experience, underscoring his own near bankruptcies and failures that ultimately led to his success. Madhani speaks to the necessity of sometimes leaving comfort and security for the sake of pursuing entrepreneurial ventures, referencing the risks she took when building her billion-dollar fintech company. Shetty mentions that entrepreneurs don't wait to feel ready but rather create, evolve, and show up, demonstrating an acceptance of the potential for failure and the need to act despite it. Grede hints at embracing failure as part of the journey, viewing setbacks not as failures but as opportunities to refine her vision and find the right collaborators.
Shetty also stresses the importance of action and learning fast over excessive preparation, promoting the idea of diving into entrepreneurship rather than over-planning. Chesky shares a nuanced view, discussing the highs and lows of his entrepreneurial journey and how the process has led to self-discovery and an understanding of what truly matters to him, which might come from experiencing and learning from failures.
Continuously Learn From Successful Entrepreneurs in Your Industry
Cody Sanchez advises finding people who are skilled in areas you're not, such as taxes, and learning from them. Rubin recommends being a sponge and absorbing the good traits of people you respect while discarding their bad qualities. Grede has reached a point in her career where the roles have reversed, and she evaluates pitches from others, signifying that she has learned enough to become an expert in her field. Chesky's realization that the journey doesn't end with achieving traditional success but continues by defyin ...
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Mindset, Skills, and Personal Growth For Entrepreneurs
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Counterarguments
- While embracing failure can be beneficial, it's also important to recognize that not all failures provide valuable lessons and some can be detrimental if not managed properly.
- Taking action without sufficient preparation can sometimes lead to avoidable mistakes and resource wastage.
- The idea that entrepreneurs should not wait to feel ready might lead to impulsive decisions without proper due diligence.
- Viewing every failure as an opportunity might lead to a romanticized view of entrepreneurship that underestimates the real hardships and consequences of failure.
- Continuous learning is important, but it should be balanced with action; too much learning without application can lead to analysis paralysis.
- Learning from successful entrepreneurs is valuable, but it's also important to critically assess whether their advice and strategies are applicable to one's unique context.
- Work ethic, grit, and passion are important, but so is work-life balance; excessive focus on work can lead to burnout and other health issues.
- Determi ...
Actionables
- Start a "Failure Resume" to document and analyze your setbacks, turning them into learning experiences. Write down each failure, what led to it, what you learned, and how you can apply that knowledge in the future. This practice helps you embrace failure as a part of the learning process and can guide you in making better decisions.
- Create a "Skill Swap" network with peers where you exchange expertise and experiences. For example, if you're good at marketing and another entrepreneur excels in finance, offer to share your knowledge with each other. This mutual exchange fosters continuous learning and helps you develop a well-rounded skill set.
- Implement a "One Action a Day" rule where you commit to taking at least one ...
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Navigating the Entrepreneurial Journey From Start to Scale
Entrepreneurs like Rubin, Sanchez, and Madhani share insights on how to navigate the intricate process of growing a business from a startup to a scale-up, underlining the importance of innovating strategies, adjusting leadership, and remaining true to core values.
Adapt Strategies & Leadership as Your Company Evolves
The entrepreneurial journey demands a flexible approach to strategy and leadership as a company expands.
Skills and Processes for $1M Vs. $100m/$1b Businesses
Madhani's approach to acquiring small businesses and shifting to an enterprise strategy underscored the need for considering scale in people, process, and profit when aiming to grow from millions to billions in revenue. Sanchez also acknowledges that the skills necessary to run a company increase substantially as the business expands. However, there is a clear consensus that only general insights into the contrasting processes and skills for businesses at different scales are provided.
Enable Scaling With Leadership Changes
Sanchez hints at adapting leadership to enable scaling, emphasizing that not everyone has the capability to run a large company like Amazon. Meanwhile, Madhani talks about the importance of bringing in new leadership and making adjustments suited to a company's growth phase, especially when aiming for the hundred-million-dollar mark or progressing towards a billion-dollar valuation.
Stay Grounded In Values and Culture During Growth and Change
Emma Grede emphasizes the importance of growth without compromising core principl ...
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Navigating the Entrepreneurial Journey From Start to Scale
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Counterarguments
- While adapting strategies and leadership is crucial, it's also important to recognize that too much change can lead to instability and confusion within the organization.
- The skills necessary to run a company may not always increase with size; in some cases, the core skills required remain the same, but the complexity and the scale of operations that those skills must manage increase.
- Not all companies aim to grow from millions to billions in revenue, and for some, such growth may not be sustainable or in line with their business goals.
- The idea that new leadership is always required for scaling may not account for the potential of existing leaders to grow and adapt alongside the company.
- Preserving core values and culture is important, but it's also necessary to allow for the evolution of culture as the company grows and the team diversifies.
- Hiring people whose values align with the company is ideal, but it's also beneficial to bring in diverse perspectives that can challenge the status quo and drive innovation.
- Being relent ...
Actionables
- You can reflect on your personal values by writing a "values manifesto" to guide your decisions. Start by listing the principles that are most important to you, then create a document that outlines how these values should influence your actions and choices. For example, if one of your core values is integrity, your manifesto might include commitments to always speak truthfully and to make decisions that align with your sense of right and wrong, regardless of external pressures.
- Develop a personal growth plan that includes learning new skills and adapting your leadership style. Identify areas where you want to improve, such as public speaking or strategic thinking, and set specific, measurable goals for developing these skills. You might, for instance, commit to reading one leadership book per month or attending a local workshop on communication skills.
- Create a "culture fit" checklist for evaluating new relationships and opportunities. Whether you're considering a new job, ...
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